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VANILLA

www.PerfumerFlavorist.com

Ethics, genomics,
flavor profiles
and more
November 2011 vol. 36 no.11

plus
Fragrance and Transparency
Dimethyl Sulfide
Piperine in F&F
FRUITIER–JUICIER–SWEETER
ETHYL DECADIENOATE NAT.

C12H20O2; CAS# 3025-30-7: This is the formula


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As a special flavor ingredient, Ethyl Decadienoate Nat.
by Symrise, naturally an essential component of apples,
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NATURAL INTENSITY
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fruit notes and the beautifully balanced taste of ripe
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by Firmenich

The Magic Inside Sclareolate ®

Frank Völkl Pierre Alain Blanc Catherine Selig


Perfumer Master Perfumer Perfumer

Nature is an endless flowing wellspring of ideas. With the creativity and enhancing the fluid movement of your creation.
most sophisticated techniques, our scientists are busy exploring No boundaries, you can really go for it!”
the structure of nature’s own molecules, reproducing their
purity in the laboratory. Perfumer Frank Völkl defines Sclare-
olate® as an exceptionally modern
Introducing the latest innovative Natural freshness, clean, material. “What I like about this note
solution from Firmenich – Sclareolate , ®
is that it’s brilliantly undefined in its
a beautifully clean white floral, clary versatile, safe – these are shape. It’s a harmonizer, able to take
sage note that brings volumes of natural
freshness to perfume creations without
the words perfumers use many forms within a creation…so that
any one single note does not stick out.
allergen restrictions. to describe Sclareolate . ®
I find it blends in very well with citrusy,
fresh aromatic top notes.” Perfumer
Master Perfumer Pierre Alain Blanc Catherine Selig agrees. “In men’s
explains, “The key for success is to find a molecule that complies fragrances, Sclareolate® achieves an aromatic note, but
with every modern safety factor – as well as being highly transforms itself in women’s fragrances, enhancing natural
performant and interesting in its olfactive facets.” Sclareolate® effects, simultaneously warm and cold. This molecule empowers
delivers. “It’s a definitive building block”, lauds Perfumer the fragrance.”
Etienne Bouckaert. “Sclareolate® is unrestricted and it out-
performs traditional linalylacetate notes. From the perfumer A molecule with such transformative powers…this is where
point of view, it allows for high volume usage, liberating your the magic begins.
WWW.FIRMENICH.COM
VOL. 36 NOVEMBER 2011
IN THIS MONTH’S ISSUE
This month P&F magazine looks at vanilla, including
genomics and vanillin biosynthesis in Vanilla planifolia
(Page 34), vanilla flavor profiles and customer trends
(Page 36), and the crossroads of ethics and market drivers
in vanilla production (Page 64).

FLAVOr
8 New Flavor Research Center Focuses on Industry Collaboration, 26 Protecting Intellectual Property in the Age of Transparency
Raw Data Needs John H. Cox
Why the defense of fragrance industry trade secrets is so
9 New Additions to the FEMA GRAS Interim List
important, both politically and legally
12 Enhancement of Retronasal Odors by Taste
34 Vanilla Enters the World of Genomics
18 Flavor Bites: Dimethyl Sulfide Daphna Havkin-Frenkel, Faith Belanger, Sharman O’Neill
and Christopher Town
John Wright
Use in vegetable, fruit, dairy, brown, fermented, and seafood A progress report
and meat flavors
36 Vanilla: Anything but Plain
46 The Universal Hotness, Part 2: Piperine Mike Fasano outlines the complexities and nuances of vanilla
extracts
Michael Zviely
Chemistry and application in flavor and fragrance
38 Davana Oil
50 Organoleptic Characteristics of Flavor Materials Pierre-Jean Hellivan
Source, chemistry, and application in flavors and fragrances
Judith Michalski
Aniseed oil, bergamot oil, bitter orange oil, black pepper oil
and more
52 Progress in Essential Oils
Brian M. Lawrence
Alaska yellow cedar leaf oil, Ceylon citronella oil and Spanish
FrAGrAnCE oregano oil
64 Last Word: Scott May on Vanilla, Ethics, and Market Drivers
9 WPC 2012 Conference, Exhibition and Sponsorship Details
Announced
Industry
11 Making a Fragrance Connection through Color

20 Fragrance and Communication 6 Editor’s Note: Imagination + Innovation: the Formula for Global
Kate Williams and Anne Gough Growth—World Perfumery Congress (WPC) 2012
How scent can help multisensory impaired children and be
applied to products of the future
8 Industry: News, Analysis and Events

14 Sensory Inspiration
28 Fragrance and Transparency Highlights from the Women in Flavor & Fragrance
Steve Herman Commerce (WFFC) New York trend excursion
Outlining stakeholder positions regarding intellectual property
protections 15 Events

44 Workplace Safety
InGrEdIEnts Patrick McNamara
Making safety policies part of the workplace culture
16 Raw Material Bulletin
60 Worldwide Sources
Triisobutyldihydro dithiazine, natural p-cymene, patchouli oil,
nutmeg Aceh oil and more 63 Ad Index

online this month www.PerfumerFlavorist.com

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EDITORIAL
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MARKETING & AUDIENCE DEVELOPMENT
Linda Knott, Director of Marketing • 1-630-344-6051/lknott@allured.com
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Imagination + Innovation: the Formula
editor’s note

for Global Growth—World Perfumery


Congress (WPC) 2012

A
s additional details of WPC 2012
continue to be revealed (see our story
on Page 9), I am pleased to announce
a new addition to next year’s program. The
Fragrance Foundation has announced that,
beginning in 2012, the FiFi Technological
Breakthrough Awards will be presented
during the WPC’s closing session, to be held
6 this coming year on June 14, 2012.
“The WPC is attended by the industry members most closely
associated with this FiFi category,” says Fragrance Foundation
president, Rochelle Bloom. “So it’s a natural move to present
the award at this venue where the recognition of the winners
will be most meaningful.”
llured at the The three subcategories for the award have been restructured
(Berjé) and Jeb Gleason-A
INSIDE: Vincent Handon tos and hig hlig hts on Page 10. as follows:
York; pho
Elements Showcase in New
• Fragrance Creation & Formulation including innovations in production or formulation;
sustainability efforts as they relate to fragrance creations and formulation; and basic
research (fragrance-centric)
VOL. 36 NOVEMBER 2011

• Fragrance Ingredients including methods of extraction; new ingredients (synthetic or


natural); and sustainability innovations
• Digital Initiatives including smartphone apps; computer programs that provide data to
assist companies with fragrance development and creation; and interactive information
technologies geared to educate and assist consumers in selecting fragrances

As always, regardless of category, all entries must be original concepts that have the potential
to move the industry ahead as a whole. Going forward, FiFi Technological Breakthrough Awards
will be presented every two years to coincide with the WPC rather than on an annual basis.
As always, companies with entries for the FiFi Technological Breakthrough Awards will
be required to make a presentation of their technological breakthrough to a panel of expert
judges. The deadline for submission of entries is Tuesday, February 1, 2012. Entry
information and forms can be found at www.fragrance.org. Inquiries regarding this award
should be directed to Terry Molnar; tmolnar@fragrance.org.
Occurring every two years, WPC is an educational and networking forum uniting fragrance
industry professionals, their suppliers and marketers to address and discuss solutions to the
industry’s latest challenges. The WPC is presented by the American Society of Perfumers and
produced by Perfumer & Flavorist magazine.
See you next month.
PERFUMER & FLAVORIST

Jeb Gleason-Allured, Editor


jallured@allured.com

WPC 2012 at a Glance


When: June 12-14, 2012
Where: MGM Grand in Mashantucket, Connecticut, USA
Learn more at http://wpc.perfumerflavorist.com, and stay connected with colleagues and
WPC attendees on LinkedIn (www.linkedin.com; group name: World Perfumery Congress).
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New Flavor Research Center Focuses on Industry
Collaboration, Raw Data Needs
industry
Celebrating the launch of its new Flavor and Research
Education Center (FREC), the University of Minnesota
held a grand opening event at the Radisson University
Hotel in Minneapolis on August 4–5, hosting attendees
from a range of flavor and food companies.“We’ve been
really happily surprised at the popularity and support
we’ve garnered so far,” commented Devin Peterson,
associate professor in the university’s food science and
nutrition department and co-director of FREC. “We have
just launched the program, and the support has been
exceptional, involving many of the largest companies in
the space.”
Kicking off the grand opening event, attendees from Gary Reineccius (University of Minnesota) and Susan Weddington
companies such as Robertet, General Mills, Firmenich, (Smucker’s).
Smucker’s, Heinz, Golden Frog, Kraft, Land O’Lakes,
8 McCormick, Kellogg’s, Hormel, Cargill, PepsiCo, Nestle,
ConAgra, DSM and more mingled at a networking social,
where graduate students from the school’s food science
and nutrition department showcased poster presenta-
tions on their flavor research and discussed the posters
with event attendees. Next, attendees chatted over din-
ner before listening to a presentation from Gregory Yip,
senior vice president of long-term R&D for PepsiCo.
Focusing on the continued need for innovation and
consumer research in the development of food and
flavored products, Yep said, “There is a recognition of a
need for more data, and we are often working on proj-
VOL. 36 NOVEMBER 2011

ects that are two to five years ahead, meaning we require


more data as time continues and things update. We are
Katie Kolpin-Gustafson (Land O’Lakes), Ken Kierzek (Land O’Lakes) and
also consistently trying to translate the difficult science to
Amy Bennett (Cargill).
the marketing end of the company.” Yep commented that
it would be via partnerships with organizations such as
FREC that this data would be cultivated.
Covering topics such as innovation in fields including
biodiversity in ingredient hunting, improving the flavor of
natural extractions, discovering new molecules developed
by nature, and work in nutrinomics, metabolomics, genom-
ics and the development of flavors that can be tailored and
personalized, Yep emphasized the need for collaboration
and the benefits of raw data. “We can build lots of different
ideas and products off such data,” he commented, urging
that such work didn’t always need to be proprietary. He
concluded his presentation with a Q&A session, discussing
future food trends and where these trends are currently
cultivating, as well as thoughts on global demographic
PERFUMER & FLAVORIST

shifts, sustainability and resource constraints, and continu-


Gregory Yep, Rashimi Tiwari and John St. Peter (all PepsiCo).
ing government interaction and involvement.
The event reconvened the next morning with a
welcome from Al Levine, dean of the University of Peterson then presented on more of the specifics of
Minnesota’s College of Food, Agricultural and Natural becoming a member of FREC—including benefiting from
Resource Sciences. Then university vice president of ongoing research and knowledge accumulated from a
research Tim Mulcahy discussed the school’s desire to global community—noting that the center would be able
maintain a position as a go-to resource for the flavor and to focus and offer a comprehensive look at flavor solu-
food industries for research and service agreements: “We tions for the food industry, as well as ways to translate that
want to provide those intellectual capital needs and build research into industry applications.
those strong working relationships with corporate spon- Next, Gary Reineccius, co-director of FREC and head
sors through programs such as the new Flavor Research of the university’s department of food science and nutri-
Education Center.” tion, discussed continuing education at FREC, including
the work the school’s graduate students would be involved on, with Peterson leading the discussion. Suggested proj-
in, as well as learning opportunities that would be avail- ects included a study of the impact of sugar and salt on
able for FREC members and non-members alike. “We are the flavor profile of extruded cereal products, advancing
continually seeking industry input on what these classes the understanding of off-flavor development and achiev-
should cover,” he commented, collecting suggestions from ing extended shelf life of omega-3 oils, and work on the
those in attendance and taking note of the possible need encapsulation and controlled release of flavorings.
for customized workshops. The event concluded with a tour of the FREC facili-
Zata Vickers, a university professor of food science and ties, located on the University of Minnesota’s St. Paul
nutrition, highlighted the sensory center in the depart- campus, and a talk about the center’s capabilities, includ-
ment of food science and nutrition, which offers sensory ing aroma isolation and analysis, taste compound isolation
testing services and support for research projects, as well and analysis, taste-aroma interactions and flavor modula-
as the ability to act as a consulting laboratory. She also tion, flavor and food processing, flavor synthesis, flavor
discussed potential projects that the sensory center could release, and flavor dynamics. “We’re very excited to get
undertake that would benefit the companies of those this work started, and can’t wait to begin collaborating
attending the grand opening event. on some big projects with our new members,” Peterson
Attendees then had the opportunity to review and concluded.
discuss new research projects FREC could begin to take
9

New Additions to the FEMA GRAS Interim List


The Flavor and Extract Manufacturers Association 1,5-Octadien-3-ol (FEMA# 4732, CAS# 83861-74-9)
(FEMA) has released its latest interim Generally Recog- is a new material that imparts earthy, mushroomlike and
nized As Safe (GRAS) list. The interim list includes four strong geranium leaf notes.
materials: (4Z,7Z)-Trideca-4,7-dienal (FEMA# 4735) is a fatty
O-ethyl S-1-methoxyhexan-3-yl carbonothioate flavor aldehyde that Lever discovered was useful in fatty
(FEMA# 4730) is a new compound from Givaudan. The flavors, and then Naarden found to be useful in fragrance
description for the material characterizes it as having formulations.
a sulfuric, blackcurrant, tropical, roasted coffee flavor, N1-(2,3-Dimethoxybenzyl)-N2-(2-(pyridin-2-yl)ethyl)
and the odor description describes it as mushroomy oxalamide (FEMA# 4741), from Senomyx, is a compound
and herbaceous with a slightly cacao connotation. It has that offers enhancement for savory and umami flavors.
been noted to be particularly effective in imparting deep Special thanks to Leffingwell & Associates for the
roasted coffee notes. ingredient information.

WPC 2012 Conference, Exhibition and Sponsorship Details Announced


Conference program, networking event, exhibition, WPC 2012, the fragrance
venue and sponsorship details for the World Perfumery industry’s premier business and
Congress 2012—taking place June 12-14, 2012 at the technical event. We look for-
MGM Grand in Mashantucket, Connecticut—have just ward to fostering a value-driven
been announced at www.wpc.perfumerflavorist.com. Pre- program for ongoing innovation
sented by the American Society of Perfumers (ASP) and and success.”
produced by Perfumer & Flavorist magazine (P&F), the Dennis Maroney, president
event’s new structure will include: of the ASP, concludes, “The
• Solution-focused discussions of industry issues cooperation between our orga-
• An emphasis on creative fragrance design nizations harnesses a combined
• Separate conference and expo hall hours 170 years of unique dedication to the fragrance industry
• And more and refocuses WPC on the ingredients, formulation, busi-
ness and consumer of perfume and fragranced products
“The World Perfumery Congress is coming,” around the world.”
announced Marvel Fields, chairperson of the ASP. “If you Keep up with the latest news by subscribing to the
are a perfumer, evaluator, marketer or safety officer, this WPC 2012 mailing list (http://wpc.perfumerflavorist.com).
meeting’s focus—creativity and innovation—is for you.” And stay connected with colleagues and WPC attendees
Jeb Gleason-Allured, editor of P&F and program on LinkedIn (www.linkedin.com) and Facebook
director of WPC 2012, adds, “It’s our pleasure to relaunch (www.facebook.com). Mark your calendar today!
Industry Snapshot: Elements Showcase
industry

10

The Elements Showcase, held August 15–16 at Skylight West in


Manhattan, offered a forum for niche and independent fragrance brands
and industry insiders.

Exhibitors launching new fragrances and fragranced products included


Etat Libre d’Orange, Bond No. 9, Lafco, Royal Apothic, D.L. & Co.,
Intertrade Europe, EM Distribution, MCMC Fragrances, Anthousa and
Ursa Major.
VOL. 36 NOVEMBER 2011

Tyann Jackson and Rocky Li (both Six Scents Parfums).

Highlighting its ingredient palette, Berjé collaborated with the Fashion


Institute of Technology (FIT) on fragrances based on student concept
displays, which were shown at the Elements event. Scents included
Riddle for Her, which included “light fruits combined with a decaying
PERFUMER & FLAVORIST

fruit accord”; Deep Sea Cret, which featured “lemon, mandarin,


bergamot, a salt accord, patchouli, rock rose, and white musk”;
Dark Matter, a masculine chypre featuring “black musk, cedar, myrrh,
coumarin and tobacco absolute”; Rust, which included notes of “rust,
blood and chrome” and featured cassis and aldehydes; and Toxic,
described as “edgy, effervescent, and slightly tainted,” with notes of
“vetiver, patchouli, leather and black pepper … beneath a sparkling
ginger accord.”

The Berjé-FIT scents also included the marine-themed Aequorea, which


featured aldehydes, Bulgarian and Moroccan rose, Egyptian geranium,
and jasmine absolute.
Making a Fragrance Connection through Color apples, herbals
When building a new product, both color and fragrance being associated
are integral parts of the development process, with the color
representing two significant sensory aspects green. If you think
that connect with consumers—sight and about it, many colors
smell, respectively. However, when name a color and an object.
these two aspects can be brought Lilac, lavender—both colors, but
cohesively together to represent also names of flowers. When we
the product, it makes the item that speak about color and want to
much stronger and more appealing describe the shade clearly, we
to potential purchasers. use fruit names or floral names
A new study from Arylessence for clarification. For example,
indicates how closely linked people’s lemon yellow, candy apple red,
senses of sight and smell are and how lime green. Fruit or floral scents
often these are significant factors in paired with their associated colors
consumers’ buying decisions. definitely make the strongest color-
Arylessence’s director of marketing scent connections.”
Lori Miller Burns explains, “Our perfum- Additionally, Arylessence found 11
ers, evaluators and marketers know that the through its deep trend market research
stronger the connection between color, name that the colors and intensities consumers
and fragrance, the more likely the consumer will be to show a preference for help shape their motiva-
purchase a product. This is the underlying principle that tions in what products they buy, how they dress and how
prompted our research. We set out to examine maxi- they decorate their homes. Therefore, it is logical that
mizing product success by looking at the harmonious these color factors should shape fragrance design. “It
relationship between color, fragrance name, fragrance is important to think about the emotional cues of color,
expectation, emotional response and even designated particularly when a product’s name is more fantasy in
room placement.” positioning. What colors depict single word concepts, like:
According to the company’s study, which surveyed caress, embrace, or kiss? With these types of concepts
female consumers in the Atlanta area, the colors of a a marketer should carefully connect the right color and
product and its packaging set an expectation about how fragrance emotional ties in the finished product,” Miller
a product should smell. “Our research shows that color Burns comments.
works even more effectively to shape consumer expecta- “The intensity and color of a fragrance influence each
tions, and that the colors of a product and its packaging other and also set an expectation with the user,” Harper
translate into winning fragrances that reflect the power of says of designing fragrance to match color. “If you were
the whole brand,” comments Arylessence president doing subtle spa aromas, you want to pair them with
Steve Tanner. muted shades that are calming and tranquil, in order to
Miller Burns also notes, “We recognized the need to reinforce and support the intensity of the fragrances.
validate the importance of the concept-color-fragrance Similarly, a vibrant yellow shade would be best sup-
connection because we were recognizing an abundance of ported by the fragrance of fresh effervescent lemon zest
disconnects in the marketplace and even with some of our or succulent tropical pineapple to clearly deliver on the
own client’s color choices. If you ever see a watermelon- consumer’s expectation. Matching color intensity with
scented candle in blue, you’ll know what we mean by a fragrance intensity is yet another way to deliver a cohesive
disconnect.” The study demonstrated consumers are often product message.”
able to describe the “scent” of selected colors, and many Miller Burns concludes, “Our perfumers create
will use the same words to describe the scent’s emotional fragrances that reflect the whole brand, have the power
effect. “It’s really all about what is natural and logical,” to attract consumers, and ultimately, become part of the
explains Michelle Harper, director of fragrance evalua- consumer’s life. Among all the components of a brand,
tion with Arylessence. “Cues from nature are the most fragrance is the one that makes the strongest emotional
obvious, such as the color red being most associated with connection. Color helps make that connection happen.”
Enhancement of Retronasal Odors by Taste
In a study published online in July in the journal Chemical notes Green, explaining that in the second experiment,
industry
Senses, authors Barry Green, Danielle Nachtigal, Samuel the researchers used a flavored beverage and a dry-mix
Hammond and Juyun Lim discussed the interaction vanilla custard dessert for real-world application testing.
between retronasal olfaction and taste.a The authors noted The results of this research found that adding sucrose sig-
that previously much of flavor enhancement was attributed nificantly enhanced the intensity of “cherry” and “vanilla”
to the effect of odors on tastes, but in their research the flavors, whereas adding vanillin did not significantly
authors found that the opposite was more often true: enhance the sweetness of the beverage or custard.
retronasal odors could be enhanced by taste. “When we didn’t add sucrose, people barely
“We are trying to understand what inter- reported the vanilla taste, and this showed
actions occur between odors and tastes up even more dramatically than it did in
to gain insights into the mechanisms of the model solution experiment,” Green
flavor perception,” says Green, who is explains. “We think the brain inter-
also director and a fellow at the John prets the whole pattern of taste and
B. Pierce Laboratory and a profes- retronasal odor stimulation, and in
sor of surgery (otolaryngology) at this case recognized vanilla pud-
the Yale School of Medicine. “In the ding as a very clear and discernable
12 past, people had studied the effect flavor object, or food.”
of odors on taste and believed that Further explaining the impor-
the main effect of an odor that was, tance of congruency, Green says,
for example, fruity was to enhance the “Just adding salt to vanilla doesn’t
sweetness of a mixture of sucrose and the work, for example. It actually suppresses
odor. But preliminary work in our labora- the taste because they clash. The impor-
tory led us to believe the more consistent effect tance of congruence of the taste with the odor
was for the taste to enhance the odor.” indicates there is a large learning component in
To test this hypothesis, the authors set up two experi- flavor and food perception.”
ments. In the first, they had student subjects rate the For the application on this research into flavor
intensity of “sweet,” “sour,” “salty,” “bitter” and “other” development, Green notes the industry has a working
sensations perceived in model solutions with three knowledge of this concept, but little knowledge of the
VOL. 36 NOVEMBER 2011

tastants—sucrose, salt and citric acid—and three odor- underlying perceptual mechanisms. “The food industry
ants—vanillin, citral and furaneol. These were sampled and flavor chemists have been more or less demonstrating
both alone and in taste-odor mixtures. Green explains, “In this concept in their preparations and research for quite
most cases, the odor, reflected in the other rating, was sig- awhile, but knowing, for example, the importance of taste-
nificantly enhanced when sucrose was the taste stimulus. odor congruence may help flavor chemists to enhance
What that implies is that the taste stimulus has to be con- particular flavors in foods by strategically choosing to
gruent with the odor—that is, normally appear in foods increase a certain taste component,” he explains.
with it—for enhancement to occur. The enhancement of “Also, with the aging population continuing to grow,
tastes by odors was inconsistent and generally weaker than and because aging often results in a weakening of the
the enhancement of odors by sucrose.” sense of smell, this research can have applications for
“In the second experiment, we followed up to address enhancing the flavorfulness of foods,” he continues.
the question, ‘Is this same effect really happening in food?’” “Intensifying the taste of foods may be at least as effec-
tive as only boosting the odor components. The downside
aBG Green, D Nachtigal, S Hammond and Juyun Lim, Chem Senses (2011); is that this may be part of the reason that foods with high
doi: 10.1093/chemse/bjr068 saccharide and salt content are so desirable.”
PERFUMER & FLAVORIST

Industry Snapshot: Betsey Johnson


Too Too Fragrance Launch Party
The early morning crowd at New York’s
Milk Studios sang Happy Birthday to
designer Betsey Johnson as she hosted
the launch party for the Firmenich-
formulated Too Too. The scent includes
notes of mandarin, ginger, Bulgarian rose,
patchouli, sandalwood and vanilla.
Theo Spilka (Firmenich) and Andy Clarke Designer Betsey Johnson holding her
(Inter Parfums). new fragrance, Too Too.
Natural Advantage is Ripe with the
Natural Sweetness of Life
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FROM THE NAME
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(very clean sweet without brown notes)
Luo Han Powder, Natural, FEMA 4711
(very clean sweet without negatives)
Anisyl Formate, Natural, FEMA 2101
(Sweet Vanilla and Berry taste)
Heliotropine, Natural, FEMA 2911
(Sweet Cherry Vanilla taste)
5-Methylfurfural, Natural, FEMA 2702
(Sweet Almond Cherry taste)
Acetophenone, Natural, FEMA 2009
(Sweet Cherry, Marzipan, Coumarinic taste)
Phenylacetaldehyde, Natural, FEMA 2874
(Sweet Almond Cherry Chocolate taste)
Linalool Oxide Prime, Natural, FEMA 3746
(Intensely Sweet Fruity Ripe taste)

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Sensory Inspiration
industry

Highlights from the Women in Flavor &


Fragrance Commerce (WFFC) New York
trend excursion
Harney & Sons offered teas with novel flavor blends and unflavored
varieties with unique sensory attributes.

A
my Marks-McGee (Trendincite) and Jeanine
Pedersen (Takasago) recently led the WFFC’s
(www.wffc.org) walking tour through New
14 York’s Soho neighborhood to introduce a range of
flavor and fragrance professionals to unique and
inspiring ingredients and textures. The first stop was
Harney & Sons tea company, which sells ~320 flavors
of tea—both flavored and unflavored—including
those for private label customers, such as Barnes &
Noble and Caribou Coffee, and hotels. Those teas
with added flavors are blended by the company at an
upstate facility. Harney & Sons also creates some RTD Valerie Belmont, Melis Cakirer, Jaime Call, Deborah O’Sullivan and
teas flavored by honey and cane sugar, and has turned Jeanine Pedersen (all Takasago).
a cinnamon tea into a soda used in an ice cream float.
During the visit, the most notable tea was the unflavored
VOL. 36 NOVEMBER 2011

Lapsang Souchong, which had a strong natural smoky


and leathery flavor and was described by one attendee
as: “like drinking bacon.” A green tea was flavored with
lemongrass, vanilla, coconut and ginger; a “Soho blend”
had notes of chocolate, vanilla and coconut; the store
also provides a jasmine and pomegranate oolong, and is
considering a lavender flavor. The company tests blends
in-store and occasionally “retires” flavors.
Next, the Pearl River Mart featured a vast array of
Asian foods and goods. Spotted during an extended
browse were: custard-stuffed Ritz crackers; soursop Art Maloney (Apple Flavors and Fragrances), Helen Feygin
candy; salted tangerine with licorice; dried shrimp (Intuiscent LLC), Jennifer Powderly (Robertet) and Amy Marks-
McGee (Trendincite LLC) at lunch at Kittichai.
snacks; peanut cakes sweetened with cane sugar; haw
slices; dried and sugared potato slices; absinthe dental
floss; and candles scented by themes such as confidence,
power, harmony and joy.
Next, retailer Space NK featured a “hand-picked”
selection of brands that allow sales staff to “prescribe”
the best skin care solutions, regardless of brand. Life
PERFUMER & FLAVORIST

NK is the store’s private label brand, which incorpo-


rates natural fragrances. The store’s top brand is Eve
Lom, an oil-based cleanser with eucalyptus and clove.
Space NK also carries unique fragrances, including
the diptyque line.
The tour wrapped up with lunch at Kittichai, featur-
ing fish cakes with cucumber and red onion chutney;
pan-seared Arctic char with dtom yum broth; pad Thai Pictured during the last stop at Rice to Riches: Valerie Belmont (Takasago),
with cashews, garlic chive and Shanghai shoots; and Joshua Engel (Ontology Works), Amy Marks-McGee (Trendincite), Dyann
banana spring rolls with burnt honey ice cream. Coratti (Intarome Fragrances), Christina Neuner (Limited Brands), Jeanine
Pedersen (Takasago), Kara Gerardi-Piacenza (International Aromatics),
This was followed by a visit to rice pudding boutique, Krishna Kundu (International Aromatics), Helen Feygin (Intuiscent LLC),
Rice to Riches. Melis Cakirer (Takasago), Italina Schifino (IFF) and Sharon Pepe (IFF).
Events
More events posted at www.perfumerflavorist.com/events. Filter events by topic and region; submit event announcements;
access exclusive event coverage and photo albums.
October 31–November 2—IFSCC Conference; Bangkok; Nord Villepinte, Paris; fieurope.ingredientsnetwork.com
contact: International Federation of Cosmetic Chemists;
December 4–8—98th Annual Consumer Specialty
tel: 44-0-1582-726661; enquiries@ifscc.org; www.ifscc.org
Products Association (CSPA) Meeting; Fort Lauderdale,
November 1–3—2011 Chem Show: 54th Chemical Process Florida; contact: Consumer Specialty Products
Industries (CPI) Exposition and Educational Conference; Association;
Jacob K. Javits Convention Center, New York; tel: 1-203- www.cspa.org
221-9232; www.chemshow.com
December 8—Society of Flavor Chemists Meeting;
November 3—Art de Vivre—Le Parfum: The Power of Sheraton Hotel, Newark, New Jersey;
Fragrance, A Scent of History; French Institute Alliance www.flavorchemist.org
Française (FIAF) Le Skyroom, New York; www.fiaf.org
January 29–February 4— 2012 American Cleaning
November 3—RIFM’s 2011 Annual Meeting; contact: The
Research Institute for Fragrance Materials; www.rifm.org
Institute (ACI) Annual Meeting & Industry Convention;
Grande Lakes Orlando, Florida; contact: ACI; www.
15
November 6–10—IFEAT 2011; Barcelona, Spain; contact: cleaninginstitute.org
International Federation of Essential Oils and Aroma February 16—Society of Flavor Chemists Meeting;
Trades; www.ifeat.org Sheraton Hotel, Newark, New Jersey;
November 9–10—Vanilla 2011; Monroe, New Jersey; www.flavorchemist.org
contact: Daphna Havkin-Frenkel; tel: 1-732-991-3462; February 19–22—Ingredients Middle East; Dubai;
daphna@aesop.rutgets.edu; www.vanilla2011.com www.gulfood.com
November 10—Art de Vivre—Le Parfum: The Power of March 7—12th Annual West Coast Flavor Industry Forum;
Fragrance, Panel Discussion; French Institute Alliance Anaheim, California; www.flavorchemist.org
Française (FIAF) Le Skyroom, New York; www.fiaf.org
April 18—Midwest Meeting of the Society of Flavor
November 9–11—World Food India; NSIC Exhibition Chemists; Cincinnati; www.flavorchemist.org
Complex, New Delhi, India; www.worldfood-india.com
May 6–7—103rd Annual FEMA Convention; The Westin
November 13–15—PLMA’s 2011 Private Label Trade
Diplomat, Hollywood, Florida; www.femaflavor.org
Show; Rosemont Convention Center, Chicago; contact:
Private Label Manufacturers Association; tel: 1-212-972- May 17—Annual Meeting of the Society of Flavor
3131; info@plma.org; www.plma.org Chemists; Sheraton Hotel, Newark, New Jersey;
www.flavorchemist.org
November 16—Art de Vivre—Le Parfum: The Power of
Fragrance, Speed Smelling; French Institute Alliance June 12–14—World Perfumery Congress 2012; MGM
Française (FIAF) Le Skyroom, New York; www.fiaf.org Grand at Foxwoods Resort, Mashantucket, Connecticut,
USA; http://wpc.perfumerflavorist.com
November 17—The Fragrance Foundation’s State of
the Industry; The Harvard Club, New York; contact: June 25–28—IFT 2012; Las Vegas; contact: Institute of
The Fragrance Foundation; arubin@fragrance.org; Food Technologists (IFT); tel: 1-312-782-8424; info@ift.org;
www.fragrance.org www.ift.org
November 29–December 1—Fi Europe & Ni 2011; Paris
ingredients Raw Material Bulletin
Naturally occurring in yeast, Symrise’s triisobutyldihydro Taste Advantage offers natural 2-isopropyl-5-methyl-
dithiazine (4H-1,3,5-dithiazine,dihydro-2,4,6-tris(2- 2-hexanal (FEMA# 3406, CAS# 35158-25-9). Useful in
methylpropyl)-; C15H31NS2; FEMA# 4017, CAS# chocolate, tea, nut, cocoa,
74595-94-1) provides a crispy bacon character when H3C CH3 tobacco and fruit flavors with
added to roasted flavors, and particularly those of onion its sweet, fruity, cocoalike
and meat. However, it can also be H 3C O flavor and aroma, it occurs
used in flavoring cereal and naturally in cocoa and is rec-
cocoa, and is recommended CH3 H ommended for use at 5 ppm.
for use at levels of 1 ppb to www.tasteadvantage.com
10 ppm.
www.symrise.com From its Terima Kasih project in Indonesia, Payan Ber-
trand offers Vetyver Process e (CAS# 8016-96-4), an
essential oil distilled under low pressure from a specific
Natural p-cymene (FEMA# 2356, CAS# 99-87-6) from
Java vetiver. This distillation process helps result in a
Axxence Aromatic is naturally found in a variety of
pure product free of the typical earthy and smoky notes.
spices and fruits and has applications for both fragrance
Instead, the material, which is useful in fine fragrance,
16 and flavor. It offers woody, citrus, berry and spicy notes
that can be used as an element in profiles of lime, herb,
offers a dense woody note with dry and powdery orris
nuances with a grapefruit accent.
mango, other exotic fruit and more. It is recommended
The company also offers nutmeg Aceh oil low BAPs
for use at 5–250 ppm.
(FEMA# 2793, CAS# 8008-45-5) as a product from its
Natural 2-methyltetrahydrofuran-3-thiol (FEMA#
nutmeg distillation and processing in Indonesia’s Aceh
3787, CAS# 57124-87-5) can be used in beef, chicken,
region. This essential oil of Myristica fragrans under-
liver sausage, cooked dairy and tropical fruit flavors to
goes rectification to reduce levels of safrole and methyl
provide fatty, roasted, cooked meat notes. Naturally
eugenol to less than 100 ppm and can be used in bever-
occurring in heated beef and pork, it is recommended for
ages and spicy flavors to add a warm, diffusive note.
use at a level of 0.1–5.0 ppm.
www.payanbertrand.com
www.axxence.com
VOL. 36 NOVEMBER 2011

Wild Flavors, Inc. has released a line of taste modifiers


Useful in baked goods, chewing gum, nonalcoholic bever-
and sweetness enhancers for use with stevia extracts.
ages, candy and more, patchouli oil (FEMA# 2838,
Along with the ability to label these modifiers and enhanc-
CAS# 8014-09-3) from Ultra International is a botanical
ers as “natural flavors,” they can be utilized to round
derivative that offers a warm, woody odor.
out the sweetness profile of a product while eliminating
Nutmeg oil (FEMA# 2793, CAS# 8008-45-5) provides
off-notes. The line was specifically developed with a sweet
nutmeg flavor and fragrance notes in applications includ-
taste modifier that works well with Reb A 60, a stevia
ing condiments, candy, chewing gum, beverages, baked
extract containing 95% stevia glycocides.
goods and more.
www.wildflavors.com
www.ultrainternational.com

Fontarôme Chemical Inc.’s 5-methyl-2-phenyl-2-


Natural Advantage has introduced natural ethyl
hexenal (cocoa hexenal, 5-methyl-2-phenylhex-2-enal;
3-methylthiopropionate (FEMA# 3343, CAS# 13327-
FEMA# 3199, CAS# 21834-92-4) occurs naturally in
56-5), a main organoleptic component in pineapple. Also
roasted peanuts and hazelnuts, cocoa, coffee and filberts,
found in passion fruit, brandy, whiskey and wine, it has
and can impart characteristics of nutty, green, cocoa,
a strong sulfurous odor at high levels, but at 10 ppb, it
chocolate fragrance notes and bitter cocoa, coffee, nutty
offers a sweet smell
O and honey notes to applications such as bread, caramel,
and tropical taste.
marshmallow and molasses.
It also adds a sweet,
PERFUMER & FLAVORIST

CH3 The company also offers T2,C6-nonadienal (trans-


ripe characteristic H C O S 2,cis-6-nonadienal, (2E,6Z)-nona-2,6-dienal; FEMA#
to flavors such as
3
3377, CAS# 557-48-2), a flavor and fragrance ingredient
berry, grape and pineapple, and is recommended for use
added to help achieve a strong cucumber and violet leaf
at levels of 0.01–1.00 ppm.
odor. It can also include fragrance notes of meat fat,
www.natural-advantage.net
spice and melon, and the taste features green, cucumber,
melon, fatty and vegetative characteristics. It is useful
Treatt offers jalapeño Treattarome, a natural FTNF in green pepper, tropical fruit, cucumber and mango
flavoring that naturally occurs in Capsicum annuum. With flavorings, and in fragrance, apple, cherry, cucumber,
characteristics of freshness, green and earthy notes with cranberry, green, floral, guava, huckleberry, mango,
paprika undertones, the material can be useful in sauces, melon and pear scents.
salsas, salad dressings, dips and other savory applications. www.fontarome.com
www.treatt.com
Dimethyl Sulfide
flavors

Use in vegetable, fruit, dairy, brown, fermented, and seafood


and meat flavors

John Wright; johnwrightflavorist@gmail.com

D
imethyl sulfide (FEMA# the ingredient that can
2746, CAS# 75-18-3) (F-1) be used without the
18 smells of boiled cabbage.a cabbage note becom-
Now, I quite like boiled cabbage but ing offensive, and
even I have to admit that such an this problem is even
odor description hints at a relatively more pronounced in
restricted range of uses. However, in applications involving
practice the exact opposite is true. heat, where the effect
Dimethyl sulfide is potentially one of dimethyl disulfide
of the most useful raw materials becomes even more
available to flavorists. It has a unique pronounced. The solution
character and is extraordinarily is to carefully redistill com-
difficult to replace. The closest mercial dimethyl sulfide and
alternative is dimethyl disulfide then store the purified chemical
VOL. 36 NOVEMBER 2011

(FEMA# 3536, CAS# 624-92-0), under refrigeration.


which is less volatile but adds a rather All the levels given in this article
dirty note to the cabbage character assume that pure repurified dimethyl
and has a much more restricted range sulfide is used and refer to concen-
of useful applications. trations of the material in flavors that Mushroom: Subtle levels, around
Dimethyl sulfide does suffer from are used at 0.05% in a ready-to-drink 100 ppm, can be helpful in cooked
two drawbacks. The first is its relative beverage or bouillon. mushroom flavors and work particu-
volatility, which means the use level larly well in flavors that recreate the
has to be adjusted carefully in flavors Vegetable Flavors character of Italian dried porcini
intended for applications involving Sweet corn: Most sweet corn flavors mushrooms. Higher levels can work
heat. The second, more serious, draw- are essentially based around dim- well to soften very sulfurous truffle
back is the fact that it tends to oxidize ethyl sulfide and very high levels, flavors.
on storage into dimethyl disulfide. even up to 10,000 ppm, can be used. Olive: Olive flavors can be quite
Even small quantities of dimethyl Popcorn flavors also utilize this difficult to formulate and similarly
disulfide severely restrict the levels of ingredient, although the effect is less low levels of this ingredient are quite
pronounced. effective, adding realism and depth.
aFind suppliers of this and other ingredients in
Cabbage: Similarly high levels
Allured’s Flavor and Fragrance Materials database; work in cooked cabbage and sauer- Fruit Flavors
PERFUMER & FLAVORIST

www.perfumerflavorist.com/ffm.
kraut type flavors. Five thousand ppm Blackcurrant: The range of use levels
is a good starting level. in blackcurrant flavors is unusually
Tomato: Dimethyl sulfide is also wide, from 200–5,000 ppm. Higher
Dimethyl sulfide F-1 an essential component of all tomato
flavors, being particularly prominent
levels, which demand an absolutely
pure quality of dimethyl sulfide, add
in flavors with the character of cooked significantly to the juicy character but
tomatoes. Levels of use vary from tend to push the flavor more in the
H 3C S 1,000–5,000 ppm. direction of blackcurrant preserve.
Onion: The chemical is much Raspberry: Typical levels in rasp-
less obvious in cooked onion flavors, berry flavors range from 200–1,000
CH3 where the effect tends to be boiled ppm and also demand good quality
rather than fried. Five hundred to raw material. The effect is to add
1,000 ppm is the optimum range. depth and juicy character.
Mango: A wide range of levels Cherry: Cherry flavors also gain chocolate flavors, and higher levels
can create different effects in mango juicy notes from levels of dimethyl are sometimes used in milk chocolate
flavors. Levels around 50 ppm add sulfide in the range of 10–50 ppm. flavors.
realism and juicy notes but much Blueberry: Quite low levels, Coffee: Similarly, around 50 ppm
higher levels, up to 1,000 ppm, can below 10 ppm, can be helpful to add of dimethyl sulfide adds complexity to
depth, realism and juicy notes to this the sulfur notes in coffee flavors and
push the character more in the direc-
difficult flavor category. increases the impression of realism.
tion of dried mangoes. Black tea: Approximately 20 ppm
Lychee: Dimethyl sulfide is an
Dairy Flavors can give black tea flavors a similar
essential component of lychee flavors, Butter: High levels of this ingredi- boost to the depth and realism of the
adding juicy notes and depth to a ent are often added to butter flavors, character.
flavor category than can tend to be especially those giving the impression
too light and floral. Five hundred of heated or cooked butter. Levels Fermented Flavors
ppm is a useful starting level in range from 500–3,000 ppm. Beer: Dimethyl sulfide is an especially
flavors. Cheese: Cheese flavors, depend- important component of all types of
Apple: This ingredient is ing on the type, can also contain high beer flavors. Levels vary, but 200 ppm 19
not commonly used in fresh levels, again up to 3,000 ppm. is typical.
Milk and cream: Lower levels are Wine: Levels in red wine flavors
apple flavors but it can be
used in these dairy flavors, often in tend to be higher, around 200 ppm,
very helpful where a slightly
the range from 10–80 ppm. than those used in white wine flavors,
cooked note is required at around 20 ppm.
levels up to 200 ppm. Brown Flavors
Apricot: Levels of use here Malt: Dimethyl sulfide is not the Seafood and Meat Flavors
vary from 10–100 ppm, higher dominant sulfur note in malt flavors Crab: This ingredient is especially
levels being more characteristic but it plays a very important role. useful in crab flavors and levels
of dried apricots than the fresh fruit. Typical levels of use range from well above 1,000 ppm can be used
Peach: The levels of use in peach 200–2,000 ppm. successfully.
flavors are a little lower than those in Molasses: Levels ranging 200–500 Shrimp: Dimethyl sulfide at levels
ppm are effective in molasses flavors, of 200 ppm and higher can be effective
apricot flavors, ranging from 10–50
while lower levels work in brown in shrimp, scampi and lobster flavors.
ppm.
sugar flavors. Chicken: The effect in chicken fla-
Strawberry: Similar levels, from Caramel: Quite low levels, 20–100 vors is less pronounced but additions
10–50 ppm, are used to impart a ppm, serve to add depth and warmth in the region of 100 ppm are useful.
juiciness to strawberry flavors, while to caramel and butterscotch flavors.
higher levels give a more cooked or Chocolate: Again, levels rang- To purchase a copy of this article or others, visit
jammy effect. ing 20–100 ppm are very helpful in www.PerfumerFlavorist.com/magazine.
Fragrance and Communication
fragrance

How scent can help multisensory impaired children and be applied to products
of the future

Kate Williams, Seven Scent; and Anne Gough, Seashell Trust

T
he sense of smell has a powerful influence
over our emotions, memories and reactions.
For children with profound learning and
20 communication difficulties, smell can help them
identify people, places and objects. So, given that
olfactory information has a direct path to our limbic
system, can it be positively harnessed in an educational
environment? A new study aims to explore not only
how multisensory impaired (MSI) children use their
sense of smell, but also whether olfactory cues can
improve their understanding, communication and
ability to make choices. Here, the authors review the
approach, considerations and initial findings of the
study—as well as the potential long-term implications Kate Williams (Seven Sce
nt) and Anne Gough (Seash
for fragranced products of the future. ell Trust).
VOL. 36 NOVEMBER 2011

A Creative Partnership
The Seashell Trust (www.seashelltrust.org.uk) is a UK- • Odor/scent can be used to add to information received
based school which offers specialist provision for children through other senses.2
and young people up to the age of 25 with sensory • Experiments using scents with students with MSI need
impairments, severe or profound learning difficulties and to be carefully planned and based on smell and func-
significant communication difficulties. Working closely with tion being linked.5
Seven Scent, the fragrance subsidiary of PZ Cussons, the
Seashell Trust aims to understand more about the ways that When working with children with profound learning
scent can be used effectively as part of the learning process difficulties, therefore, it may seem logical to assume that
with students. The recent study was devised in order to the use of smell—as well as touch and residual vision
put a formal structure behind anecdotal and observational and hearing—is likely to be helpful. There are, however,
evidence of the students using their sense of smell to better a number of hazards which need to be addressed when
understand their environment. isolating the influence of olfaction. 3, 5
A growing body of research into olfaction and its role
in enhancing human cognition provides a valuable basis • Smells can’t be “put away” or “turned off.”
for the study and can be summarized into a number of • Fragrances that are not integral to the activity may
PERFUMER & FLAVORIST

suggestions: confuse students.


• Some students may be hypersensitive to specific smells.
• The sense of smell has a direct link to memory and
• Odors tend to be unpredictable (e.g., affected by air
emotions.1
currents) and transient.
• The sense of smell underpins much of humans’ social
• Some students with MSI have an impaired sense of
interaction and awareness of others.2,3
smell. This is particularly likely in students with the
• People with visual impairments and blindness
genetic condition CHARGE syndrome.a
may develop more acute responses to olfactory
• All of these concerns were addressed in the planning
information.4
and implementation of the Seven Scent-led study.
• The sense of smell tends to work as a background sense
rather than foreground sense, and information gained aCHARGE syndrome comprises coloboma of the eye, heart defects, atresia
through smell can be overridden by information from of the nasal choanae, retardation of growth and/or development, genital and/
other senses.2 or urinary abnormalities, and ear abnormalities and deafness.

Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2011 Allured Business Media.
Axxence Aromatic GmbH
Tackenweide 28 · D -46446 Emmerich · Germany · Telephone +49 2822 68561 0 · service@axxence.com
Axxence SARL
ZAC Sainte Marguerite · 107, Route du Plan · F-06130 Grasse · France · Telephone +33 493 408890 · info-france@axxence.com
Axxence Slovakia s.r.o.
Poštová 1 · SK-81106 Bratislava · Slovak Republic · Telephone +421 2 54 41 44 46 · service@axxence.com

www.axxence.com Warehousing also in USA


fragrance
The experiment, conducted by Seven Scent
and the Seashell Trust developed a number
of fragrances for use in daily routines to help
children make the connection between pictures
and what they represented—the fragrances
appeared to bridge a gap in understanding.

22
VOL. 36 NOVEMBER 2011

Familiar staff worked with the children and


introduced familiar objects of reference (OR)
during their everyday routine; the only change
was that certain OR now had a fragrance added.

First Stage Observations to photographs and Jason began to make the connec-
As a first step, time was spent observing 12 children and tion between the picture and what it represented. The
recording how they made use of smell in the context of fragrances appeared to bridge a gap in his understanding.
their multisensory modes of learning. One student was As Jason began to understand what the pictures stood
chosen to work on a one-to-one basis with researchers, with for, some written words were introduced with a fragrance
the aim of gaining valuable learnings for the development attached. Using the food and drink fragrance was highly
of a research program for the wider group of students. motivating and Jason gradually learned to recognize writ-
Jason had a multisensory impairment affecting his ten words of some of his favorite food and drinks.
vision, hearing and communication. He had a bilateral The results of this two-year study are extremely
sensorineural hearing loss compounded by auditory pro- encouraging; Jason now:
cessing difficulties. His vision was significantly impaired
• No longer requires pictures to be fragranced to recog-
PERFUMER & FLAVORIST

through the condition called Peter’s Anomaly; he also had


nystagmus and a diagnosis of glaucoma. He was highly nize them
motivated by visual stimuli, such as lights, spinning toys • Uses pictures and words to communicate his wants and
and movement, but his initial reaction to everything was needs in different contexts
to smell it. Jason’s communication was limited to the here • Recognizes some words without fragrance
and now. He had no interest or recognition of pictures • Can follow handwritten shopping lists independently
and signs and made very few responses to sound. Close
observation showed that Jason identified people through Fragranced Objects of Reference
their odor and reinforced his understanding of objects, Whilst Jason was recognized as exceptional, the research-
food and drinks using his sense of smell. ers felt that his responses supported the idea that other
Seven Scent developed a number of fragrances that students with MSI could benefit from using smell. This
Jason could use in his daily routine to make choices led to further research designed to explore how it could
between his favorite drinks. The fragrances were applied be used effectively.
It should be noted that the next stage of the study
was carried out in the context of a number of important
considerations. Firstly, children with MSI are difficult
to study systematically due to the interactive effects of
different impairments, inconsistencies of behavior and
difficulties of knowing what information a child is receiv-
ing.6 It is also important to protect children who cannot
anticipate or understand novel experiences from potential
distress. The fragrances used in the study were specifically
created with the involvement of a toxicologist to ensure
they would be safe for students when they came into
contact with the skin, were licked or accidentally ingested.
The approach was carefully thought out and child-
centered to guarantee the safety and care of the students
throughout.
Eight students were chosen for formal observation
and a simple study schedule developed. Video filming
was used to observe and record the ways in which the 23
group of children made use of smell in the context of their
learning timetable and in particular in association with
locating a room where that smell would be functional.
The study period took place over 18 months and each
child was observed and filmed daily—with the exception
of absences due to holidays or illness.b
Familiar staff worked with the children and introduced
familiar objects of reference (OR) during their everyday
routine. The only change was that certain OR now had
a fragrance added. The same fragrance was added to
the room destination for the activity represented on the
OR. Film was used to record the OR being presented
and the student’s response each time. The film was then
analyzed for possible factors affecting response. Hazards
described in previous olfaction research were minimized
or avoided:5

• Fragrance pens were used to add the scent to the OR


to minimize leakage of smell.
• The fragrance in the room was functional and was part
of the activity in the room, such as massage.
• Students were carefully observed so that any hypersen-
sitivity or unhappiness would be picked up. None was
noted and the evidence suggested that the students
enjoyed the scent.

Sensory Theater
A second approach used scent in the creation of a mul-
tisensory theater environment where a specialist room
housed a computer that linked video images with sur-
round sound and lighting effects to create the overall
atmosphere. Although less rigorous in its analysis of
results, the project provided valuable initial learnings
on how multisensory experiences can be beneficial in
allowing students to revisit real life experiences and
encourage them to recall events, resulting in communica-
tion enabling them to express to others what they did and
how they felt.
Three strong themes were chosen with each room
designed and fragranced appropriately.

bFind footage of the authors’ research at www.perfumerflavorist.com.


• Seaside: Students who had visited the seaside recently easily available through other channels. The work will
used the theater to recall the experience. How did the concentrate on the students’ ability to anticipate and com-
fragrance
students respond? When the door was opened for the municate choice, taking that learning and generalizing it
first time, the smell of the beach was so strong that two to the wider world.
of the children who had bare feet on their trip to the The study not only demonstrates the beneficial results
sea removed their shoes before entering. of fragrance in certain therapeutic treatments, it also has
• Bonfire Night: This theater housed a party with the broader implications for the industry where fragrance may
smell of fireworks and bonfire. The result: a visually be used to create products which generate quantifiable
impaired student recognized the smell and sounds emotion, for example, or a mood-altered state. Further
upon opening the door and so sat on the floor with his research into this complex area may lead to exciting new
hands over his ears waiting for the fireworks. product developments which fully exploit the power of
• Christmas: A pine fragrance was used to enhance the fragrance.
smell of Christmas trees, together with a spicy orange
and clove fragrance to create a festive atmosphere. Address correspondence to Kate Williams, Seven Scent, Lamplight Way,
Some of the children really noticed the scents when Agecroft Commerce Park, Manchester M27 8UJ, England.
they were enhanced in this way and showed more
interest in the stimuli, often becoming still while smell- References

24 ing and then smiling. 1. J Willander and M Larsson, Olfaction and emotion: the case of
autobiographical memory. Memory and Cognition, 35(7), 1659–1663
Initial Findings (2007).
While this work so far is exploratory, initial observa- 2. SM Aglioti and M Pazzaglia, Sounds and scents in (social) action.
tions and analysis suggest that scents may be able to help Trends in Cognitive Sciences, 15(2), 47–55 (2011).
students engage and maintain interest in an activity. They 3. U Stockhorst and R Pietrowsky, Olfactory perception, communication
may also evoke an emotional response from the student. and the nose-to-brain pathway. Physiology and Behaviour, 83, 3–11
The work to date has provided important learnings on (2004).
how to use scents to provide additional information 4. M Beaulieu-Lefebvre, FC Schneider, R Kupers and M Ptito, Odor
as part of each child’s development as communicative perception and odor awareness in congenital blindness. Brain Research
individuals. Bulletin, 84(3), 206–209 (2011).
Observations suggest that using scent can help some 5. D Brown, The sense of smell—the olfactory sense. DbI Review, 4–8
VOL. 36 NOVEMBER 2011

students to engage with experiences. For some, it has (2007).


been possible to begin to use olfactory information in con- 6. H Murdoch, Early intervention for children who are deaf and blind.
junction with other sources to support locational learning. Educational and Child Psychology, 21(2), 67–79 (2004).
For many, it appears to add to enjoyment in a range of
situations and in recalling experiences.
The aim is to build on the students’ experiences, To purchase a copy of this article or others,
focusing on using scents in choice-making, which is not visit www.PerfumerFlavorist.com/magazine.
PERFUMER & FLAVORIST
Protecting Intellectual Property in the
fragrance

Age of Transparency
Why the defense of fragrance industry trade secrets is so important,
both politically and legally

John H. Cox, General Counsel, IFRA North America; Managing Director, Verto Solutions

T
wo years ago the International Fragrance and environmental advocates. Some of the groups most
Association (IFRA) took the unprecedented step vocal about fragrances include Campaign for Safe Cos-
26 of publishing a list of all fragrance ingredients used
around the world. This list of just over 3,000 ingredients
metics, Environmental Working Group, Women Voices
for the Earth, Breast Cancer Fund and potentially The
was compiled and updated last year and is available at PEW Charitable Trusts. In this context, the fragrance
www.ifraorg.org. industry’s North American branch, IFRA North America
The list publication is just the most recent innovation (IFRA NA), is actively building alliances with key stake-
in what IFRA chairman Michel Bongi recently referred holders and policymakers to advocate for preserving the
to as the “industry’s continuous approach to building trust ability of the industry to protect its intellectual property.
in the safety of the materials we use.” Publishing this list The main elements of IFRA NA’s political message are:
was an enormous step toward increased transparency and
• Fragrances are valuable intellectual property represent-
is helping the industry learn more about the ingredients
ing enormous investment in research and development.
used to make fragrances. However, disclosure of ingre-
A requirement to disclose the individual ingredients
dients in individual fragrance compounds is at the heart
used in fragranced products would cause irreparable
VOL. 36 NOVEMBER 2011

of the fragrance industry’s concerns with protecting its


harm to the industry.
intellectual property.
• Fragrance industry safety testing and use restrictions
Serious questions face the fragrance industry. Will a
are robust. More money is spent every year and there
legislature, perhaps in California or another US state,
is constant pressure to be more thorough, innovative
or even in the US Congress, require the disclosure of
and current in the testing program.
individual fragrance ingredients used in a particular con-
• There is an increasing willingness to share additional
sumer product? The impact of such a requirement on the
information about fragrance ingredients in use and that
fragrance industry would be significant. This is why the
is precisely why IFRA published a list of ingredients.
defense of fragrance industry trade secrets is so impor-
tant, both politically and legally.
The Legal Issues
Like any manufacturer, fragrance companies have all clas-
The Political Landscape sifications of confidential business information: customer
More information on just about every subject is available lists, ingredient suppliers, new product development
on the Internet. Consumer access to this information ideas and proprietary financial data. It can be argued
has become a way of life, inevitably leading to calls for that fragrance formulas are the most valuable intellectual
consumer product companies and fragrance suppli- property owned by the fragrance houses.
ers to disclose what ingredients are used in individual Between the fragrance houses and their consumer
fragrances. In response, the fragrance industry published product customers, ownership of the fragrance formula
PERFUMER & FLAVORIST

the IFRA list. However, it is not prepared to disclose the is a contractual matter; this is not covered by this article.
ingredients or concentrations used in individual prod- This article addresses what’s at stake as the government
ucts because doing so would mean that the compositions considers requiring disclosure of the ingredients used in
would no longer be proprietary, in which case they would individual fragrances in consumer products.
lose their value. The entire business model of the industry Intellectual property is protected in several ways under
would be nullified. US law. There are copyrights, which protect original
Public opinion polls show that the typical consumer works of authorship including literary, dramatic, musical
does not want to see the names of chemicals in their prod-
ucts; they just want to know that their favorite products
are safe. This data suggests a lack of grassroots interest in Join the discussion of these and other issues on
knowing what ingredients are used in individual fragrance LinkedIn (www.linkedin.com); group name: Perfumer &
compounds. Yet public pressure on fragrance houses for Flavorist (P&F) Magazine.
disclosure is being created by a small cadre of consumer
Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2011 Allured Business Media.
and artistic works such as poetry, novels, movies or songs. their market position. The key to many successful con-
Trademarks protect words, names, symbols or designs sumer products is the fragrance. If the fragrance formula
used in commerce. Patents are granted by the govern- for a popular body wash, shampoo or air freshener were
ment to protect inventions or discoveries of new and to be disclosed, it would facilitate replication, making it
useful processes. Although patents are sometimes used much easier and inexpensive to copy popular fragrances.
to protect individual fragrance molecules or fragrance After years of research and development, including exper-
delivery technologies, they are not practical for protecting imenting with different ingredients and combinations of
compounded fragrance blends. ingredients, and market testing with consumers, would it
There are many tens of thousands, and perhaps hun- be fair to make a company disclose this information?
dreds of thousands, of unique fragrance mixtures, with Protecting fragrance trade secrets isn’t easy, but it is
each representing an olfactory point of difference from critical to the long-term survival of the industry. Current
the others. To a consumer each of these mixtures smells law, the Uniform Trade Secrets Act, common law cases,
different from the others; however, this fact is insufficient agency regulations, the Freedom of Information Act
for the uniqueness required to receive a patent. After all, (FOIA), even the Federal Food, Drug & Cosmetic Act,
it can be claimed that these mixtures repeatedly comprise all contain trade secret protections. The Congress or a
many of the same materials, only in different combina- state legislature shouldn’t just run past this long history of
tions. Use in commerce for a certain amount of time is
another patent requirement. This, combined with the
protection. 27
Want to get involved and keep up with the latest devel-
application requirement, means that the formula must be opments in fragrance intellectual property protections?
revealed before the patent is awarded. Taken together, all Join IFRA NA and/or IFRA. More information is avail-
of these requirements make patents ill-suited for protect- able at www.ifrana.org and www.ifraorg.org.
ing fragrances.
Under existing law, the most appropriate way to protect Address correspondence to John Cox, Verto Solutions, 1620 I St. NW Suite
fragrance formulas is to keep them as trade secrets. By 925, Washington, DC 20006; jcox@vertosolutions.net.
definition, what makes it a trade secret is the secrecy.
Secrecy is not a popular concept in these days of ubiq- To purchase a copy of this article or others,
uitous and instant information, which is why protecting visit www.PerfumerFlavorist.com/magazine.
fragrance formulas is so challenging.
From a legal standpoint, what would happen if the
US Congress or a state legislature mandated disclosure
of trade secret ingredient information such as fragrance
formulas? The negative commercial impact of such a
requirement would be so significant that litigation chal-
lenging the law would almost certainly result.
A legal challenge from individual companies or an
industry association would require a court to weigh the
public benefit of disclosure compared to the harm to
companies set to lose their trade secrets. Such a challenge
might involve the “takings clause” of the US Constitution.
The 5th Amendment clause requires “just compensa-
tion” when private property is taken for public use. If
there were a legal challenge the legislative record would
probably include justifications for the disclosure require-
ments, i.e. public health, consumer awareness, protection
for special populations, etc., and the court would have
to decide what’s more important, the consumer’s right to
know or the industry’s valuable intellectual property. For
now this issue remains in the political arena.

Next Steps
Any legislative ingredient disclosure requirement must
thoughtfully address this legitimate trade secret issue,
otherwise the battle is likely to shift to the courts. Main-
stream politicians of both major US political parties
know that business interests matter and that a sudden
and dramatic move in this area might affect US jobs and
innovation. Forcing companies to reveal their fragrance
formulas would make it impossible for companies to hold
Fragrance and Transparency
fragrance

Outlining stakeholder positions regarding intellectual


property protections

Steve Herman, Diffusion LLC

T
ransparency was the unexpected ingless, since fragrance companies have been efficiently
centerpiece of Sustainable Fragrances 2011 copying each other’s formulas since the GC/MS became
(www.sustainablefragrances.com), held last omnipresent in the 1970s. Individuals or whole depart-
June in Washington, DC. During the preconference ments devote their time to duplication. The argument
28 seminar, Paul Anastas of the US Environmental
Protection Agency, and father of green chemistry, said
continues that consumers, given ingredient disclosure,
are not going to make their own fragrances any more than
“disclosure is coming.” It is not coming because of any they now make a Dr. Perricone cream using the ingredi-
pending legislation, but rather because of a desire from ent label.
consumers and some consumer goods companies to lift The International Fragrance Association (IFRA; www.
the veil of secrecy from fragrance ingredients. Anastas ifraorg.org/en-us/Ingredients_2) has published a list of all
is not a perfume industry insider, but rather a highly fragrance materials used worldwide, and one approach to
regarded scientist with a passion for the environment, fragrance disclosure already available is to simply refer to
and his comment represents a deep undercurrent that list. That, one might argue, is equivalent to having an
pushing for meaningful ingredient disclosure. Yet not all interest in Shakespeare and being pointed to the Oxford
stakeholders—fragrance manufacturers and consumer English Dictionary for further information. This argument
products companies in particular—are on the same page. continues that the IFRA list provides insufficient help
VOL. 36 NOVEMBER 2011

Cosmetics have been labeled for 40 years and the for a consumer having a reaction to a specific product
world hasn’t come to an end. Is there something so fun- containing a specific fragrance material. The complete list
damentally unique about a fragrance in a shampoo that is as far as IFRA can take the matter; further disclosure
puts it into a different dimension than a L’Oréal anti-aging would require information at the individual product level
cream? Many say yes. (See Page 26.) Two common argu- from the consumer companies.
ments against listing fragrance materials are intellectual From a logistics standpoint, the length of formulas is
property (IP) concerns and the length of most fragrance an issue, if placed on packaging, but not if placed on a
formulas. The IP issue, some argue, is essentially mean- company website. The cumbersome appearance of many

Examples of Seventh Generation Fragrance Ingredient Disclosure


Natural 4x Laundry Detergent (peppermint)) for Lemongrass & Clementine Zest:
(Citrus nobilis (clementine), Citrus aurantium bergamia
Essential oils and botanical extracts* in Geranium Blossoms
(bergamot), Cymbopogon citratus (lemongrass), Canarium
& Vanilla only: (Prunus amygdalus dulcis (sweet almond)
luzonicum nonvolatiles (elemi), Citrus aurantium dulcis
oil, Citrus aurantium dulcis (orange) peel oil, Citrus limon
(orange)) for Fresh Citrus & Ginger: (cedrol, Canarium
(lemon) peel oil, Pogostemon cablin (patchouli) oil, cedrol,
luzonicum gum nonvolatiles (elemi oil), Cinnamomum
Litsea cubeba fruit oil, Cananga odorata flower (ylang
zeylanicum bark extract (cinnamon leaf oil), Citrus
PERFUMER & FLAVORIST

ylang) oil, Citrus aurantium bergamia (bergamot) fruit oil,


aurantifolia (lime) oil, Citrus aurantium amara (bitter
citronellol, vanillin, Coriandrum sativum (coriander) fruit
orange) oil, Citrus aurantium bergamia (bergamot) fruit
oil, -caryophyllene, Eugenia caryophyllus (clove) leaf oil,
oil, Citrus aurantium dulcis (orange) oil, Citrus limon
Pelargonium graveolens flower (geranium) oil). 
(lemon) peel oil, Coriandrum sativum (coriander) fruit
*Citral and d-Limonene are components of these essential oils. oil, Elettaria cardamomum (cardamon) seed oil, Eugenia
caryophyllus (clove) leaf oil, Myristica fragrans (nutmeg)
Natural Dish Liquid kernel oil, Pelargonium graveolens (geranium) flower oil,
Essential oils and botanical extracts* for scented varieties Zingiber officinale (ginger) root oil).
only: for Lavender Floral & Mint: (Citrus aurantifolia (lime), *d-Limonene is a component of these essential oils.
Cananga odorata (ylang ylang), Lavandula angustifolia Source: www.seventhgeneration.com/ingredients
(lavender), Mentha spicata (spearmint), Mentha piperita

Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2011 Allured Business Media.
fragrance ingredients—for instance (3a,4,5,6,7,7a-hexa- interested in viewing the list of fragrance ingre-
hydro-4,7-methano-1H-inden-6-yl)oxy]-acetaldehyde—is dients used in consumer goods worldwide, visit
not user friendly, but the cosmetic industry does manage the International Fragrance Association’s (IFRA)
with ingredient names such as undecylamidopropyltri- website.
monium methosulfate. Presentations by the Michelle
Radecki of the American Cleaning Institute and D. Doug- The Clorox approach is the IFRA concept on a smaller
las Fratz of the Consumer Specialty Products Association scale, and does not represent disclosure linked to specific
grappled with labeling and nomenclature issues. Since the products. Clorox probably had all the necessary informa-
fragrance industry already has a list online, some stake- tion in house to compile the list posted on its site without
holders believe it is reasonable to use it for disclosure, cooperation from their suppliers, except for the confiden-
even if some of the ingredient names are formidable. tiality agreement that is routinely signed when the initial
Some companies have tackled the ingredient issue with disclosure is made.
limited success. Seventh Generation, for example, has Amidst these disclosure moves, groups such as the
listed its fragrance ingredients (www.seventhgeneration. Campaign for Safe Cosmetics are spreading misin-
com/ingredients), but these are
simple blends of essential oils, not
the complex (and often long) com-
bination of naturals and synthetics 29
of a typical formula. Some exam-
ples are shown in Examples of
Seventh Generation Fragrance
Ingredient Disclosure. Seventh
Generation is the most socially
conscious and well intentioned
company possible, but its fra-
grances do not reflect the industry
norm and thus it does not provide a
useful template for a wider applica-
tion of disclosure.
SC Johnson’s “What’s Inside”
program (www.whatsinsidesc-
johnson.com) will soon include
fragrance, according to the com-
pany. That has been the message
for many months, highlighting the
challenges facing a mainstream
company in dealing with the major
fragrance suppliers. Meanwhile,
Clorox’s disclosure site (www.clo-
roxcsr.com/fragrances/) states:

Below, we’ve listed all the


common names of fragrance
ingredients we use in our
consumer and professional
cleaning and laundry products
in alphabetical and numerical
order. If you’re interested in
identifying the CAS Registry
Numbers (the unique numeri-
cal identifiers assigned by the
Chemical Abstracts Service to
every chemical available in open
scientific literature) or scien-
tific names (provided by the
International Union of Pure and
Applied Chemistry [IUPAC])
of our fragrance ingredients,
please download the more
extensive PDF file. If you’re
formation disguised as facts. The Campaign’s “Not So a fundamental psychological reason. According to a CNN
Sexy” publication (http://safecosmetics.org/downloads/ story, “People can be extremely resistant to unwelcome
fragrance
NotSoSexy_report_May2010.pdf ) is emblematic of this factual information. They tend to resist or reject informa-
problem. One section claims, “Laboratory tests commis- tion, including scientific evidence that contradicts their
sioned by the Campaign for Safe Cosmetics revealed 38 pre-existing views. In some cases, corrections even made
secret chemicals in 17 name-brand fragrance products, misperceptions worse—a result called a ‘backfire effect.’
compounds detected in tests but not listed on labels.” It The defensive response is driven by the threat that con-
is the avoidance of transparency, in this author’s opinion, tradictory information poses to people’s self-concept.”b
that has made such irresponsible and misleading attacks Scientific sites aren’t comforting for the industry either.
possible. The Society of Toxicology (SOT; www.toxicology.org/pr/
Toxicology is a difficult science. The Research Institute ToxTopics/TT1_Asthma.pdf) cautions, “In order to prevent
for Fragrance Materials’ (RIFM; www.rifm.org) science, asthma attacks, avoidance of triggers is important … use
as published in peer review journals, is not intended for fragrance free products.” The consumer looking for infor-
the general public, and the Design for the Environment mation on fragrance safety is not likely to go to IFRA for
guidelines push that technical difficulty to the extreme. the authoritative answer when so much unqualified noise
Even if the science was simple, there would still be prob- litters the Internet.
lems arising from a lack of scientific literacy in the general
30 public. As Jon Miller noted in an editorial, “We should
The industry needs a response at a seventh grade level
to defend fragrance safety in the face of all the online
take no pride in a finding that 70 percent of Americans
attacks and bad science that is so easy to disseminate. The
cannot read and understand the science section of the
seventh grade level comment is not intended as mean
New York Times.”a There is a major disconnect between
spirited but rather represents a reality that even govern-
the science generated by RIFM and the emotional
ment agencies like US Environmental Protection Agency
response the general public elicits every time negative
are facing.
report on the dangers of fragrance appears.
The difference between data and criteria is particu-
Lack of transparency also opens the door to conspiracy
theories concerning fragrance ingredients. Trying to larly challenging to communicate. RIFM and IFRA are
counteract negative messages with facts may not work for based on risk rather than hazard, and criteria are set by
an Expert Panel that applies a combination of extensive
awww.sciencedaily.com/releases/2007/02/070218134322.htm technical knowledge with nuance of interpretation to
VOL. 36 NOVEMBER 2011

arrive at the guidelines used by industry. This is a process


that is intellectually challenging even for most industry
professionals, much less the general consumer. Fragrance
companies are fighting a rear action to maintain the
mystique of fragrances, but the fact is that they are mix-
tures of chemicals subject to all the safety and regulatory
requirements of chemicals in general. The public wants
disclosure. Some companies are trying to post ingredi-
ents on their websites and are obviously finding intense
resistance from suppliers. Someday a government agency
or new law may make this discussion irrelevant, but pro-
actively taking the initiative is always the best approach,
and it has served the cosmetic industry well for 40 years.
Would full ingredient disclosure in a Web-based, uniform
format change that? With some accompanying easy to
understand explanations of safety and toxicology (admit-
tedly a tall order), could perfumes cease to be demonized
for “secret ingredients,” endocrine disruptors, phthalates
PERFUMER & FLAVORIST

and all the other “evil” materials? Ultimately, would a fra-


grance with ingredient transparency smell as sweet, and
be less threat to the industry than the current distrust and
confusion? The industry must form its own answers.
b www.cnn.com/2011/OPINION/04/28/nyhan.birther.truth/index.

html?hpt=Sbin

Address correspondence to Steve Herman, Diffusion LLC;


steve@stephen-herman.com.

To purchase a copy of this article or others,


visit www.PerfumerFlavorist.com/magazine.
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Vanilla Enters the World of Genomics
ingredients

A progress report

Daphna Havkin-Frenkel and Faith Belanger, Plant Biology and Pathology Department, Rutgers University;
Sharman O’Neill, Department of Plant Biology, University of California at Davis; and
Christopher Town, The J. Craig Venter Institute

T F-2
he shape, size and properties of any organism— Scanning electron micrograph of the hair cells
animal, plant or microbe—are determined by the of a developing Vanilla pod
34 information encoded in its genome (DNA) and
how the readout of this information is modulated by its
interactions with the environment. The last decade has
provided numerous examples of how genomic information
has guided and informed our understanding of human,
animal and plant health and disease. However, because of
the costs involved, application of genomic approaches was
previously limited to humans and the major agricultural
plants and animals. Within the last few years, the
development of new DNA sequencing technologies has
revolutionized the study of crop plants. New technologies
are now available that provide high-throughput DNA
VOL. 36 NOVEMBER 2011

sequence coverage at low cost, making their application to


smaller crops possible. Two research groups are currently
applying these new technologies to Vanilla planifolia to
study some of the important issues with Vanilla, such as
disease susceptibility and vanillin biosynthesis.
At Rutgers, Daphna Havkin-Frenkel and Faith
Belanger are currently pursuing characterization of the
and characterization of the enzymes involved. One of the
vanillin biosynthetic pathway. Although vanillin is one
reasons that the biosynthetic pathway for a molecule as
of the most important flavor compounds in the world,
simple as vanillin is not yet known is the difficulty and
its biosynthetic pathway is still not known. Understand-
expense in obtaining appropriate biological material for
ing the vanillin biosynthetic pathway will be important
research. Vanillin is synthesized in abundance only in
in future efforts to improve vanilla flavor. Based on the
some species of Vanilla, and only in specific tissues at
vanillin structure, several possible pathways have been
a specific developmental stage of the developing pods.
proposed, but none have been confirmed experimentally.1
The specialized hair cells near the center of developing
One of the proposed pathways is shown in F-1. Confir-
Vanilla pods have been proposed as the site of vanil-
mation of any biosynthetic pathway requires purification
lin biosynthesis (F-2).2 The limited tissue availability
of these specialized cells makes standard biochemical
approaches to characterization of the vanillin biosynthetic
F-1
PERFUMER & FLAVORIST

A proposed biosynthetic pathway for vanillin pathway impossible.


As an alternative to direct enzyme purification from
the tissue of interest, DNA sequencing of expressed genes
in the target tissue followed by characterization of likely
genes has become a successful approach. In this approach,
RNA (which represents the genes being expressed in that
tissue) is isolated from the tissue of interest and converted
to DNA, which is then sequenced. Pathway genes identi-
fied through DNA sequencing can be then be cloned
into bacteria and the bacteria will produce the enzyme
encoded by the cloned gene. The pathway enzymes can
then be purified from the bacteria instead of from the
original tissue, in this case the Vanilla hair cells.

Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2011 Allured Business Media.
The DNA sequencing approach can be used to provide relatedness. By combining this information with their
clues as to what genes are important in a particular path- varietal characteristics, it should be possible to home in
way by analyzing the abundance and tissue location of a on those varieties that are the best candidates for crop
particular sequence. For example, since vanillin is synthe- improvement, be it flavor, disease resistance or stress
sized only in specialized cells in the developing pod, genes tolerance.
that are expressed exclusively in those specialized cells are The next few years will be very exciting for Vanilla
likely to be involved in the biosynthetic pathway. Using research. DNA sequencing often results in unexpected
standard sequencing technology, researchers obtained insights into an organism’s physiology and evolution and
some sequence data from genes expressed in the pod hair the authors expect the same for Vanilla.
cells, the likely location of vanillin biosynthesis, and char-
acterized two candidate O-methyltransferase genes. One Address correspondence to Faith Belanger, Plant Biology and Pathology
of these was highly expressed in the hair cell tissue and is Dept., Cook College, Rutgers University, 59 Dudley Road, New Brunswick,
New Jersey 08901; belanger@AESOP.Rutgers.edu.
likely to be involved in the vanillin biosynthetic pathway.3
The relatively low cost of next-generation sequencing
technologies makes it feasible to obtain massive sequenc- References
ing datasets of expressed genes from different tissues and
1. RA Dixon, Vanillin biosynthesis—not as simple as it seems? In:
developmental stages of Vanilla pods. Comparisons of
abundance of expressed genes at the different develop-
Handbook of Vanilla science and technology. Edits, D Havkin-Frenkel
and FC Belanger, pp 292–298, Wiley-Blackwell, Oxford, (2011). 35
mental stages can be used to identify the genes involved
2. DM Joel, JC French, N Graft, G Kourteva, RA Dixon and D Havkin-
in the biosynthetic pathway. Havkin-Frenkel and Belanger Frenkel, A hairy tissue produces vanillin. Israel Journal of Plant Science,
are collaborating with Richard Dixon from the Noble 51, 157–159 (2003).
Foundation to obtain sequence data from different pod 3. T Widiez, TG Hartman, N Dudai, Q Yan, M Lawton, D Havkin-Frenkel
tissues harvested at different times of pod development. and FC Belanger, Functional characterization of two new members of
Those genes whose expression is correlated with the tim- the caffeoyl CoA O-methyltransferase-like gene family from Vanilla
planifolia reveals a new class of plastid-localized O-methyltransferases.
ing of synthesis of vanillin and that are mainly expressed Plant Molecular Biology, 76, 475–488 (2011).
in the hair cells will identify the pathway genes, which will
be further characterized by enzyme purification from bac-
To purchase a copy of this article or others,
teria. The researchers expect that this massive sequencing
visit www.PerfumerFlavorist.com/magazine.
approach will allow them to finalize the vanillin biosyn-
thetic pathway.
Sharman O’Neill and Christopher Town are using
new sequencing technologies to better understand fruit
development and pod shattering and to identify genes that
are important for disease resistance. Through the Vanilla
Sustainability Project, funded by General Mills, they are
embarking on a first exploration of the Vanilla genome.
The Vanilla genome is quite large, comparable in size to
the human genome. To reduce the scope of the project,
their first effort is directed at generating sequence of just
the Vanilla genes, which represent just a small fraction of
the entire Vanilla DNA complement. From this informa-
tion, it will be possible to make a catalog of the entire
Vanilla gene repertoire including those involved in fruit
development and flavor generation as well as those that
might condition disease resistance. During the course of
this work, they will also explore the genetic repertoire of
Vanilla bahiana, which shows greater Fusarium resistance
and might provide impetus for introgression of resistance
traits into V. planifolia.
Vanilla has been vegetatively propagated for the past
300 years; thus many plantings of this crop are very
closely related. A critical aspect of the future of Vanilla is
to introduce new germplasm and traits into the crop. In
addition to developing the gene catalogs described above
and monitoring how their expression changes during fruit
(pod) formation, O’Neill and Town will also survey the
diversity of extant Vanilla cultivars. Using a technology
known as genotyping-by-sequencing that can cost-effec-
tively sequence just a fraction of each genome, they will
survey cultivars from around the world to determine their
Vanilla: Anything but Plain
ingredients

Mike Fasano outlines the complexities and nuances of vanilla extracts

“V
anillin, on its own,
is one-dimensional,
but vanilla flavor
36 is highly complex,” said Mike
Fasano (David Michael & Co.)
during a presentation at the
recent joint meeting of the
Chemical Sources Association
and Society of Flavor Attendees smelled a variety of vanilla extracts, including Bourbon and
Chemists.a The complexity Tahitian, in addition to high and low pressure extracts.
of vanilla is derived from
the ~400 components identified in the extract to date,
including sulfur compounds. While advanced analytical
work continues to decode the components of vanilla,
its standard of identity in the United States remains
VOL. 36 NOVEMBER 2011

unchanged. This standard, Title 21—Food and Drugs,


Section 169.175, states in part:

[V]anilla extract is the solution in aqueous ethyl


alcohol of the sapid and odorous principles
extractable from vanilla beans. In vanilla extract
the content of ethyl alcohol is not less than 35
percent by volume and the content of vanilla
constituent, as defined in 169.3(c), is not less
than one unit per gallon. The vanilla constitu-
Mike Fasano (David Mi
ent may be extracted directly from vanilla beans chael & Co.) presenting
during the fall meetin
of the Chemical Sourc g
or it may be added in the form of concentrated es Association in Ne
wark.
vanilla extract or concentrated vanilla flavoring
or vanilla flavoring concentrated to the semi- customer requests Bourbon vanilla, they really mean they
solid form called vanilla oleo-resin. want vanilla from Madagascar, Reunion and the Comoros.
Fasano went on to post annual vanilla production esti-
Interestingly, Fasano noted, under this standard of
mates (not all could be confirmed, he noted):
identity vanilla is not a flavor, but rather a food. Under
this standard, only two species are recognized: Vanilla • Madagascar: 13,000 metric tons
PERFUMER & FLAVORIST

planifolia and Vanilla tahitensis. (There are 100-plus non- • Uganda: 180 metric tons
commercialized varieties.) Vanilla tahitensis “is a hard sell • India: 150 metric tons
in America,” said Fasano, who noted that it is tenacious • Indonesia: 120 metric tons
and particularly good in yogurts. • Papua New Guinea: 50 metric tons
Vanilla growing regions include Uganda, Indonesia, • Comoros: 50 metric tons
India, Mexico and, predominantly, Madagascar. One of • Tahiti: unreliable data; some estimates claim
the dominant methods of cure, Bourbon, is popularly ~10 metric tons
identified with Madagascar, Reunion and the Comoros, • Mexico: unreliable data; some estimates claim
but Fasano noted the method is employed in many of the ~10 metric tons
other growing regions. However, he cautioned, when a
Vanilla extracts can be produced using hydroalcoholic
aLook for more photos and coverage in the December issue of Perfumer & maceration, hydroalcoholic percolation and, for higher
Flavorist magazine; www.perfumerflavorist.com/subscribe. folds, vacuum distillation. Producers may use ethyl
Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2011 Allured Business Media.
alcohol as a solvent, or hexane, though the latter material
has fallen out of favor due to what Fasano characterized
as “chemophobia.” Extracts can also be produced using
critical and supercritical CO2 processes. Ethyl alcohol and
CO2 extracts can have solubility issues, Fasano noted.
Next, Fasano outlined the flavor characteristics of vari-
ous vanilla types. Bourbon was described as:
• Balsamic
• Beany
• Brown
• Creamy
• Phenolic
• Pruney
• Resinous
• Rummy

Fasano pointed out that terms like beany and phenolic 37


are difficult to interpret and define, making communica-
tion with customers a complicated process.
Indonesian vanilla was described as:
• Astringent
• Clove
• Phenolic
• Resinous
• Smoky
• Spicy
• Woody

Tahitian vanilla was described as:


• Almond
• Anisyl
• Cherry
• Fruity
• Tobacco

Mexican vanilla was described as similar to Bourbon,


though perhaps woodier. Any differences could be attrib-
uted to differing soil chemistries.
Today’s customer, Fasano noted, is looking for new and
novel flavor types and “signature flavors” (“I don’t know
what it is, but I know it when I see it”). Paradoxically, he
added, customers are reluctant to move too far away from
products already on the market. In addition, tight product
development timelines can result in under-researched
concepts that don’t clearly define consumer preference.
At the same time, product research is very expensive and
R&D bears a disproportionate share of funding cutbacks
in tough times.
Yet vanilla is versatile, and a “feel-good” flavor. Not
all of its possibilities have been fully explored. Fasano
explained that vanilla is a sweetness enhancer and a heat
modifier that continues to find use in sweet, dairy and
other categories, while making inroads in savory and spice
flavor profiles. Vanilla is anything but plain.

To purchase a copy of this article or others,


visit www.PerfumerFlavorist.com/magazine.
Davana Oil
ingredients

Source, chemistry, and application in flavors and fragrances

Pierre-Jean Hellivan, Vigon International

Pierre-Jean Hellivan,
Vigon International

M
uch has been written about the great classic 6 in between seedlings is found to be optimal. Tighter
ingredients that dot the palettes of perfumers spacing will result in essential oil content reductions.
and flavorists. Surprisingly, however, there are Wider spacing will result in taller plants with less herb-
38 few references to an extraordinary essential oil, davana age and less oil. The plant is rather sensitive to weather;
(Artemisia pallens). Its history in the industry is short; a moderate sun-filled winter condition with no frost and
first distillations were reportedly conducted in India in moderate showers fosters the most favorable conditions
the first half of the 20th century, yet it was not until 1970 for the growth of davana. On the other hand, higher tem-
that exports from India started intensifying, and not until peratures and excessive rains will inhibit its development
1985 did davana become a household name marketed and impact its essential oil content.
to fragrance consumers with the launch of Davana by Four months are required to allow davana to fully
Franka M. Berger.1 Today, davana remains a small- mature. Harvesting is done by hand, cutting the plant at
volume essential oil; the 2010–2011 crop period yielded its base with a sickle, at a rate of 10–12 tons/ha. Pre-
production of 4,000 kg, according to estimates by Kancor cisely 110 to 115 days after sowing, davana is in bloom,
Ingredients. Despite this, the essential oil
has earned a special place in perfumers’ and
VOL. 36 NOVEMBER 2011

flavorists’ palettes, particularly in the United


States and Japan, where it is a flavor ingredient
for bakery, tobacco and beverage applications.2

Cultivation
Davana (A. pallens) is an annual branched
herb. The plant grows knee-high and looks
much like a small fern. It is most fragrant at
maturity, when it produces tiny flowers that
are rich in essential oils. India is the sole
source of A. pallens. The crop occurs in its
southern tier, Tamil Nadu and Karnataka,
with the outskirts of Bangalore producing the
largest volumes. Davana does grow well in
various types of soil, but does best in the sandy
or red loamy soils of south India. It thrives in
nutrient-rich black loam with good drainage. Cultivation of davana in southern India; photo courtesy of Sreekala Nair, Kancor Ingredients.
Even though davana can grow year-round,
PERFUMER & FLAVORIST

optimal essential oil content is reached only when the the telltale sign that the crop has reached its optimal
plant is allowed to grow through the winter. In the fall, essential oil yield. It is indeed the flower heads of davana
nurseries are busy growing seedlings; usually 1.5 kg of that hold the largest amounts of oil. Harvest is precisely
the prior crop’s seed will yield enough seedlings to trans- timed with the bloom, usually starting in late February,
plant 1 ha. Within six to eight weeks, in early November, reaching its peak through March and early April. Best
seedlings are transplanted from nursery to field. At that yields and quality of oil are obtained from plants cut just
stage they are 10 cm tall. Fields are meticulously pre- before the flowers open completely. Laboratory tests
pared, with bunds and channels for optimal irrigation confirm that the major portion of the essential oil is held
and intercultural operations, as is so common in India. in the flowers: twice as much oil is held in the flower
Manure is the preferred fertilizer. Upon transplanting, heads alone, compared to leaves and stems. One often
irrigation is fine-tuned based on weather conditions. The witnesses early pre-bloom harvest, but this early crop is
art of correctly spacing rows and seedlings within each destined for the Indian flower markets for garlands and
row is perfected here: spacing of 1 ft between rows and bouquets.
Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2011 Allured Business Media.
Distillation and Chemistry
Steam distillation is the preferred extraction process for
davana. The raw material is the freshly harvested herb,
processed whole, but allowed to dry somewhat before dis-
tillation. The drying period ranges from two days to one
week, depending on weather conditions, plant moisture
upon delivery to the distillery and the processor’s specific
habits. Kancor Ingredients reports that, under labora-
tory conditions, the oil content of the whole plant is as
high as 0.29%. Large scale distillation normally achieves a
recovery rate of 0.2%, translating into 12–13 kg of oil/ha.
R.N. Kulkarni of the Central Institute of Medicinal and
Aromatic Plants in Bangalore reports, “The oil is distilled
at a pressure of 1.0–2.0 kg/cm2 for 10–15 hours; the bulk
of the oil is, however, distilled in about 8 h. The recovery Davana seedlings; photo courtesy of Sreekala Nair, Kancor Ingredients.
of the oil from the semi-dried herbage is generally 0.2%.”1
In terms of processors, rudimentary farm-level stills share
the annual output with much larger scale distillation oper- Davanone
F-1 39
ations. To help separate the oil from the distillate water,
a saturated solution of sodium chloride (salt) is often used.
Davanone, a sesquiterpene ketone, is the major
component and quality driving factor of davana oil (F-1). H3C O
High-quality material usually boasts a davanone content at
or above 50%. Grades around 45% will usually be offered CH3
at a discount. Nerol is present at 10%, while geraniol is H3C
found at 5%. Surprisingly, its largest component, cis- H O
davanone, has been shown to be odorless.3 Davana’s
H3C
H 2C
signature aroma actually comes from davana ether, davana-
furans, dihydrofurans, dihydrorosefurans, trans-hydroxy
I NGREDIENTS

CAPTURING THE
E S S E N C E O F N AT U R E

w w w. m a n e .c o m
davanone, hydroxy dihydroxorosefuran and furano-nor- appreciate its rich blackcurrant top complementing wood
ingredients
diterpenoid blended with cinnnamyl cinnamates—even and hay notes, drying down fruity winey with the depth
though they are all found at less than 2% in the oil. of tobacco.
Lawrence reported that in 1991 Misra et al. identified the Davana is first and foremost a flavor ingredient. Chief
following compounds in lab-distilled dried davana (T-1).4 flavorist Chris Williams (WILD Flavors) describes a
The risk of adulteration of the oil grows as market prices blotter as “floral woody fruity and seedy with dark under-
rise. Quality control procedures should include testing for tones.” When questioned on the cognaclike character,
undesirable additives such as vegetable or fixative oils. Williams replies, “Yes, it comes from that woody character
of cedar wood and oak, reminding indeed of oak alcohols
Sensory Characteristics such as bourbon and whiskey.” Upon tasting the oil in
Davana’s reddish brown essential oil boasts a potent, solution, Williams notes “the pleasant fruity taste of grape
exquisite scent. Its character is shockingly reminiscent of and apple.” A davana sensory chart is depicted in F-2.
old spirits like cognac, with sharp, dry fruit notes, and a
full body with thick honey herbaceous notes. Perfumers Fragrance Application
Fine fragrance perfumer Ilias Ermenidis (Firmenich)
began using davana with Givenchy Pour Homme and

40
Compounds found in a lab-distilled dried
davana5 T-1 Givenchy Pour Homme Blue Label. Since that time,
it became one of his favorite ingredients in men’s fra-
grances. “Every single of one of my men’s formulas
Components % contains davana,” says Ermenidis. “At low levels, it adds
cis-davanone 38.0% an impressionist finishing touch.” Ermenidis describes
trans-davanone 5.0% davana as reminiscent of champaca, fruity herbaceous,
isodavanone 3.0% aromatic, almost woody, with a penetrating alcohol side
cis-hydroxy-davanone 2.0% like whiskey. “Davana marries well with ozone notes, and
trans-hydroxy-davanone 2.0% provides warmth to aquatic fragrances,” he says. “It adds
nerol 10.0% dimension and tames the sharp edge of woody notes.”
geraniol 5.0% Senior perfumer Shere Rolo (Trilogy Fragrances)
dihydro rosefurane 2.5% pours her creativity mainly in the niche markets of
dihydrofurans 2.5% natural fragrances for personal care and air care. “For
VOL. 36 NOVEMBER 2011

davanic acid 2.5% me, davana is almost plum, a very deep plum, with a
furano-nor-terpenoids 2.0% rosy preservelike character,” she says. “Considering the
a-nor-diterpenoid furan 2.0% sky-high cost of natural rose ingredients such as rose oil
cinnamyl cinnamate 2.0% or phenyl ethyl alcohol natural, I find davana very useful
dihydroneolidol 2.0% as a rose replacement type when blended with geranium
artemone 1.5% oil. It will greatly deepen the rosy character of geranium,
nor-davanone 1.5% and yield a natural poor man’s rose oil.” In rose formula-
davana ether 1.5% tions, davana is used to round the fragrance, to tame the
a sesquiterpene alcohol furan 1.5% minty metallic edge of geranium; it is used more for its
hydroxy nerolidol 1.2% low-dosage effect than for its character itself. To deliver
trans-davanafuran 1.0%
davana esters 1.0%
davanol
p-cymene
0.8%
0.8%
Davana sensory chart5 F-2
g-cadinene 0.8%
ethyl davanate 0.7%
cis-davanafuran 0.5%
hydoxy dihydrorosefuran 0.5%
Sensory Chart
PERFUMER & FLAVORIST

linalool 0.5% Herbal


borneol 0.5% Spicy Harsh
lilac aldehyde 0.5%
linalool oxide 0.5% Terpene-like Ethanolic
lilac alcohol 0.5%
hydroxydihydrose furan 0.5% Floral Woody
farnesol 0.5%
8-oxoerolidol 0.5% Green Resiny
camphene t
sabinene t Fruity Medicinal
nor-davana ether t Pungent

t = trace (<0.05%)
natural plum notes, Rolo also relies on davana. It
is a useful tool to imitate the effect of synthetic
dimethyl benzyl carbinyl butyrate, and the former
bases Mirabelle 2000 or Prunella. Rolo cautions,
however, that “in natural perfumery one never
speaks of natural duplications for the synthetics;
instead we talk of natural renditions.”

Flavor Application
Senior flavorist Brigitte Pellen (Firmenich) relies
on davana for a wide range of fruity notes. “The
main tonalities where it contributes the best are
red fruits, berries like strawberry or raspberry,” she
says. In addition, she reports interesting applica-
tions in beverage flavors. “Due to its herbal, dry
notes, it fits also fantasy compositions like cola,
enhancing cola for confectionary orientation,
41
Harvesting of davana; photo courtesy of Michael Dube.
giving a dry, somewhat herbal note,” says Pellen.
“Another suitable fantasy tonality, typical of Europe, is oil through dilution poses both a challenge and a sense of
grenadine.” She has also noticed davana’s performance accomplishment.
in dried fruit flavors such as fig, prune or date: “When Senior flavorist Jack Rothenhoefer (Tobacco Technol-
davana is used at a low level it gives roundness and con- ogy) likes to use davana oil to boost tea and fresh tobacco
tributes to the typical dried fruit character.” notes. “There are no aroma chemicals like it, no substi-
Williams recommends careful dosage to remain below tutes” he says. “A little will go a long way. Beyond tobacco
astringency thresholds and prevent the davana character notes, davana also has the functional benefit of a salivating
from becoming overwhelming or too prevalent. “I use effect. It will not cover off-notes, but it does blend very
davana in all types of fruit flavors, mostly for berries like well. It is a great taste/flavor modifier and tobacco booster.
strawberry, raspberry, for cassis (blackcurrant), but also I successfully used davana to complement damascenone,
for white grape,” he says. “Also, davana adds seediness or as an ingredient to replace damascenone.” Interest-
and helps me round out the flavor.” ingly, when questioned about trendy spirits flavors in the
In the art of flavoring tobacco, essential oils are key cigar industry, Jack stressed that davana’s cognac charac-
building blocks in the development of unique aroma ter is not useful here; rather, synthetic esters are a more
systems and product differentiation. Tobacco flavorists cost-effective option. He adds, “Unlike similar ingredients
incorporate davana oil in their flavor systems to enhance like boronia or osmanthus absolutes, I never experienced
the natural flavor characteristics of tobacco in their availability issues with davana oil.”
development of what
the US Food and Drug
Administration calls
“non-characterizing”
Davana pricing trends F-3
flavor systems. The aro-
matic essence of davana
oil is multifaceted, with
a unique composition of Davana Price factor
furanoid sesquiterpenes.
For tobacco flavorists, 6.00
documenting its tena- 5.00
cious aroma and flavor
4.00
contribution is an ever-
changing experience 3.00
with each dilution. In 2.00
higher concentrations Price factor
1.00
davana exudes sweet-
balsamic-woody-winey 0.00
2006 Beg
2006 End
2007 Beg
2007 End
2008 Beg
2008 End
2009 Beg
2009 End
2010 Beg
2010 End
2011 Beg
2011 End

notes reminiscent of
flue-cured tobacco. In
dilution, more subtle
essences of fermented
dried fruit emerge.
Learning to control the Data provided by Kancor Ingredients
tenacity of this essential
Market Dynamics
ingredients
After a decade of relative stability,
the market dynamics of davana
oil went out of balance (F-3). The
fragile equilibrium of supply and
demand—always challenged by poor
crops, high demand and inventory
positions—rocked davana mar-
ket prices. In 2008, demand was
reported to have nearly doubled, just
when difficult weather conditions
yielded the poorest crop in years.
Prices increased sixfold, with many
buyers settling for poor-quality,
low-davanone oil. Interestingly,
Kancor Ingredients reports that it
was during the highest priced season
42 of 2009 that exports doubled from
4,000 kg to 8,000 kg. Motivated
by a perceived growing demand Davana harvested pre-bloom is destined for the Indian flower markets for garlands and bouquets;
and sky-high prices, local farmers photo courtesy of Michael Dube.
and major processors increased
acreage. Subsequent crops delivered ample supply in a is under davana cultivation, but accurate data is not avail-
depressed economy, yielding much carryover stock. In able as to the historic acreages.”
2011, in which weather conditions have been less than Shedding the sustainability spotlight on davana reveals
ideal and crop output much below expectation, carryover interesting facts. While areas of improvements will always
inventories helped keep market prices in check. Kancor be found under the economic and social pillar, it is the
Ingredients reports: “Currently, about 1,500 acres of land ecological pillar that deserves the most attention. On the
positive side, the crop is cultivated, not wild. Fertilization
VOL. 36 NOVEMBER 2011

is from poultry manure, not chemicals. The crop is mostly


free from pests, and usually does not require pesticides.
Some farms have fallen victim to leaf-eating caterpillars
and termites and may employ systemic or contact insec-
ticide.6 However, one concern stands out: water (F-4).
Davana is a thirsty plant. Proof is in the accounting;
watering accounts for nearly 20% of the cost of its essen-
tial oil.8 Furthermore, its growing region is experiencing
declining water levels, and no major irrigation projects
are underway. Sourcers sensitive to sustainability should
therefore zero-in on this specific risk, and bring aggressive
water conservation programs to these farms. Some farms
do take advantage of the nearly 10 mm of monsoon rains
by collecting rain water, and thereby greatly reduce their
ground water consumption.

Conclusion
Opportunities for continuous improvement of davana
PERFUMER & FLAVORIST

management are wide open: better botanical selections


for increased extraction yields, better understanding of
supply demand acreage and carryover inventories for
calmer market dynamics, and creation of clear physico-
chemical standards to define and promote higher quality.
Nature creates an endless bounty of tools for perfumers
and flavorists. Nothing smells like davana. Is it not time
for our creators to give it more justice?

Acknowledgements
The author wishes to thank Chris Williams, Jack Rothen-
hoefer, Ilias Ermenidis, Shere Rolo, Brigitte Pellen and
F-4
Address correspondence to Pierre Hellivan, Vigon International Inc.,
Davana farming costs RR2 Box 2093, Airport Road, East Stroudsburg, PA 18301-9629;
phellivan@vigoninternational.com.

References
Farming cost Share of total cost 1. RN Kulkarni, Artemisia pallens. In: Artemisia. Edit, CW Wright, Taylor
Seed and nursery 15% & Francis, London (2002).

Labor 54% 2. DH Panda, Aromatic Plants Cultivation, Processing and Uses. p 372,
National Institute of Industrial Research (2009).
Plant protection 0%
3. AF Thomas, G Pitton, Helv Chim Acta, 54, 1890 (1971); AF Thomas
Watering 18% and R Dubini, Helv Chim Acta, 57, 2076 (1974).
Manure and fertilizer 12% 4. LN Misra, A Chandra and RS Thkaur, Fragrant components of oil
from Artemisia pallens. Phytochemsitry, 30, 549–552 (1991); originally
cited in Brian Lawrence’s Perfumer & Flavorist review, Davana Oil.

5. A Kamath, MR Asha, S Narasimha, D Rajalakshmi, Comparative study


of odour and GC-olfactometric profiles of selected essentials oils. Flav
those who asked to remain unnamed for their comments.
Fragr J, 16(6), 401–407 (2001).
43
Special thanks to Kancor Ingredients CEO Gemon Korah 6. DH Panda, Aromatic Plants Cultivation, Processing and Uses. p 377,
National Institute of Industrial Research (2009).
and key accounts manager Sreekala Nair for contribut-
ing very detailed agricultural and market dynamics data. 7. R Hedge, SC Ramesh Kumar, KS Anil Kumar, V Ramamurthy, Soil site
suitability and economics of cultivation of Davana (Artemisia pallens).
Access to the Firmenich library at its Grasse-based J Agric Sci, 21(4), 565–567 (2008).
naturals business unit was arranged by marketing manager
Virginie Gervason. Finally, thanks to Stephen Somers Sr.,
president of Vigon, for supporting the time efforts and To purchase a copy of this article or others,
resources required for this article. visit www.PerfumerFlavorist.com/magazine.
Workplace Safetya
industry

Making safety policies part of the workplace culture

Patrick McNamara, Scarinci Hollenbeck

I
n recent years the controversy surrounding the use and safety program. Workers need to be informed and
of chemicals like diacetyl has brought a heightened updated about materials that may contain flavoring
scrutiny to workplace safety practices in the flavor agents and any potential hazards. Employees need to
industry. One result was the publication of various be given general information and specific hazard warn-
guidance documents to address the subject from ings for workplace postings, proper container labeling,
organizations such as National Institute for Occupational access to and availability of material safety data sheets,
44 Safety and Health (NIOSH; www.cdc.gov/NIOSH/) and and updated training. It is incumbent upon employers
governmental agencies such as the Occupational Safety to make sure that this information is updated regularly
and Health Administration (OSHA; www.osha.gov). and that access to it is made, and in fact encouraged.
Numerous trade associations, Workers need to be trained
such as the Flavor and Extract about the various means avail-
Manufacturers Association able in the workplace to limit
(FEMA; www.femaflavor.org) or eliminate exposure, not
and International Fragrance only for themselves but for
Association (IFRA; www. their follow workers.
ifraorg.org), have also issued 3. Administrative controls:
guidance documents about These come down to the basics
workplace safety. Many of these at any workplace. It extends
recommendations apply across beyond just making sure that
VOL. 36 NOEMBER 2011

the board and not just to the material safety data sheets are
use and handling of a specific openly and easily available to
chemical. However, once these employees. It includes enforc-
policies are implemented, it ing safe work practices to
is equally important that they limit the release of chemicals
be followed on a daily basis. In and dust into the workplace,
effect, these policies have to maintaining appropriate seals
become part of the workplace on containers with unused
culture. Otherwise, failing to or residual amounts of ingre-
ensure these processes and procedures are adhered to dients, good housekeeping practices, establishing and
on a day to day basis will unfortunately defeat the very following all standard protocols for cleaning the work-
purpose for which they were created. The following are a place, mixing tanks and other containers, and restricting
series of general recommendations that should be part of access to areas where ingredients are openly handled
any workplace safety program: so that only essential workers who are wearing the
appropriate level of personal protective equipment are
1. Engineering controls: Engineering controls are entering or working in these areas.
considered one of the primary means to minimize 4. Substitution: NIOSH defines this as substituting a
PERFUMER & FLAVORIST

workplace exposure to potentially hazardous chemicals. less hazardous material in order to reduce a potential
This includes the use of a closed production system, workplace hazard. However, substitution does not
improvements to ventilation, isolating areas where always represent a feasible approach in manufacturing
chemicals and other ingredients are openly handled, a certain product or could actually result in the substi-
personal ventilation and respiratory equipment, and tution of a more hazardous material. Accordingly, this
temperature controls. requires careful evaluation by a manufacturer before
2. Employee and worker education: Maintaining electing to pursue this route.
employee awareness of hazardous exposures in the 5. Personal protective equipment: The use of proper
production process is a vital element of any health respiratory protection, as well as skin and eye pro-
tection, is an essential part of workplace safety. It is
aThe contents of this article are not meant to provide specific legal advice
important for companies to enforce the use of chemical
with respect to any specific matter and should not be acted upon without resistant gloves and proper fitting eyewear and respira-
professional counsel; discuss these and other safety issues on the Perfumer
& Flavorist (P&F) Magazine LinkedIn forum: www.linkedin.com. tory gear for workers with potential exposure in the

Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2011 Allured Business Media.
workplace. It is also crucial to establish and enforce of respiratory safety issues. This is in addition to making
specific guidelines about when to use such equip- sure that employees have quick and easy access to certain
ment for each job, based upon the knowledge of the material safety data sheet information. It includes mak-
tasks that need to be performed, the substances that ing sure that labeling of bulk products, especially those
are being used, and a full assessment of the potential that are considered to pose a hazard in the workplace, are
exposures. OSHA provides detailed requirements for strictly adhered to throughout the manufacturing pro-
respiratory protection standards under existing federal cess. Labeling information is critical in instances where
regulations. OSHA regulations require that companies manufacturers and suppliers are not advised by their cus-
provide personal protective equipment whenever nec- tomers as to how the product is going to be utilized. This
essary to address hazards which are “capable of causing often arises because a customer is keeping information
injury or impairment” to any body function; this confidential to protect valuable trade secret information
includes whether the exposure is by absorption, inhala- related to their product. There is also no guarantee that a
tion or physical contact. Respirators that are selected customer may communicate to a supplier how they plan
for use should be certified by NIOSH in accordance to use a certain product, but then modify their plans for
with federal regulations. Respiratory equipment should the given product. The appropriate warning statements
be serviced on a regular basis, and employees fully and labeling can provide a means for manufacturers to
trained in the proper use of this equipment. OSHA give additional information to customers to attempt to
also has regulations concerning fit testing protocol for insure the safe handling and use of their product. It may
be appropriate for suppliers and customers to enter into
45
certain types of respiratory protection equipment.
confidentiality agreements to address trade secret con-
Beyond these recommendations, employers also need cerns so that the appropriate information can continue to
to ensure their facility complies with the regulatory be provided but yet done so in a manner that honors the
requirements at the state level. It is not uncommon for need for the customers to protect proprietary information.
some states to have workplace safety regulations that dif-
fer from or are even more stringent than those issued by Address correspondence to Patcick McNamara, Scarinci Hollenbeck, 1100
Valley Brook Ave., P.O. Box 790, Lyndhurst, NJ 07071-0790; pmcnamara@
the federal government. scarincihollenbeck.com.
One of the more difficult issues that employers have
to wrestle with is the monitoring of worker health. This
always raises a concern as to potential liability expo- To purchase a copy of this article or others,
sure for a company that does this type of monitoring. visit www.PerfumerFlavorist.com/magazine.
However, before any company engages in such prac-
tice, it should carefully evaluate not only what type of
monitoring program will be instituted, but how it will
be maintained, as well as an evaluation of potential
availability of coverage under health plans for routine
physicals and other types of medical monitoring. This is
separate and apart from any type of exposure monitor-
ing that is done through regular air sampling performed
in the workplace to insure the continuing effectiveness
of the various types of controls aforementioned. As
for workplace air monitoring, it is important that any
company that is brought in is fully familiar with OSHA
and NIOSH standards, is certified in air sampling, and
is in a position to assess and recommend any type of
additional engineering or other appropriate control
measures to improve workplace safety.
Should a facility find that employees are experienc-
ing symptoms of respiratory illness such as prolonged
or work-related difficultly in breathing, shortness of
breath on exertion, pursuant coughing, wheezing or
chest tightness, or who are demonstrating symptoms
consistent with skin rashes, nasal irritation or irritated
eyes, these are all clear signals that there is a need for
immediate response on the part of the facility operator.
With regard to management and employee aware-
ness through education, it is critical that companies do
more than promote a general awareness of OSHA or
other applicable requirements. Formal and mandatory
hazard communication and training sessions that are
done on a routine basis are strongly recommended to
insure that employees have the appropriate awareness
The Universal Hotness,
Part 2: Piperinea
flavor

Chemistry and application in flavor and fragrance

Michael Zviely, CIC; mzviely@cathay-israel-chemistry.com

P
iperine (FEMA#2909, CAS# 94-62-2) (F-1) occurs
in pepper, has a pungent, aromatic, tasty flavor, and
is applied in spicy formulations.b It has a value of
46 200,000 Scoville units (SU) in comparison to capsaicinc
(CAS# 404-86-4), which has 30,000,000 SU. It has been
established that the isomers of piperine have almost no
pungency and that the slow photoisomerization observed
in solutions of piperine explain the observed reduction
in the pungency of pepper products under certain
conditions. It is suggested that old samples of pepper
may contain relatively large amounts of the almost non-
pungent isomer isochavicine.1
Piperine (5-benzo[1,3]dioxol-5-yl-1-piperidin-1-yl-
penta-2E,4E-dien-1-one) has two double bonds within its
C5 section, which can have four different stereoisomers,
VOL. 36 november 2011

including 2E,4E, 2Z,4Z (isopiperine), 2Z,4Z (chavicin)


and 2E,4Z (isochavicin) (F-2). Physical Data for Piperine
The pungency caused by piperine is caused by activa- Appearance: White to yellow crystalline powder
tion of the heat- and acidity-sensing transient receptor
potential channel vanilloid (TRPV) ion channel type 1 Molecular weight: 285.34
(TRPV1) on nociceptors, or the pain-sensing nerve cells. Molecular formula: C17H19NO3
The effects of piperine were characterized on the human Melting point: 131–135oC
vanilloid receptor TRPV1 using whole-cell patch-clamp
Log P: 2.66 (estd.)
electrophysiology. Piperine produced a clear agonist
activity at the human TRPV1 receptor, yielding rapidly
activating whole-cell currents that were antagonized by
the competitive TRPV1 antagonist capsazepine (CAS# Piperine can be prepared synthetically from a piperi-
138977-28-3) (F-3).2 dine (FEMA# 4244, CAS# 109-05-7) and bromoacetyl
It has been shown that TRPV1 is able to sense a vast bromide reaction with 3-benzo[1,3]dioxol-5-yl-acrylic acid
range of stimuli and exerts multiple functions under ethyl ester (CAS# 81581-27-3). The latter is prepared by
physiological or pathophysiological conditions. TRPV1 not reacting piperonal and ethoxy acetyl bromide (F-4).5
only plays a fundamental role in pain signaling but is also
involved in many other physiological or pathophysiological
PERFUMER & FLAVORIST

functions, including beneficial effects on cardiovascular


and gastrointestinal function.3
Piperine F-1
Piperine can also stimulate pigmentation in the skin
together with exposure to UVB light.4

a Part1 of this series, which ran in the October 2011 issue of Perfumer &
Flavorist magazine, dealt with allyl isothiocyanate (The Universal Hotness,
Part 1: Allyl Isothiocyanate, pp. 66–69). Part 3 will deal with capsicum,
ginger and curcumin hotness, and with Sichuan peppercorn’s special
characteristics.
b Some information on organoleptic properties and uses are taken from e.g.

FRM 2001 Database of Perfumery Materials & Performance, Boelens Aroma (E,E)-1-Piperoylpiperidine
Chemicals Information Services, The Netherlands.
c Capsaicin will be discussed in the next installment of this series.

Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2011 Allured Business Media.
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www.bontoux.comȱ
Piperine’s four stereoisomers F-2
flavor

Molecule, chemical name Name, FEMA# (if applicable), CAS#

Piperine, FEMA# 94-62-2,


CAS# 94-62-2

48

Isopiperine, CAS# 30511-76-3


VOL. 36 november 2011

Chavicin, CAS# 495-91-0

Isochavicin, CAS# 30511-77-4


PERFUMER & FLAVORIST

Piperine has a burning feeling. It is used in flavors at Additionally, pepper is not only among the most
0.01 ppm, and in fragrances at 0.01%.d important spices of international trade for foods, but its
Black pepper oil (FEMA# 2845, CAS# 8006-82-4) has essential oil has also become increasingly fashionable
an aromatic, spicy, slightly woody-balsamic, warm, ter- in perfumery. One prominent example is Parfum Sacré
peny, herbaceous odor and flavor. It is used in aromatic, (Caron, 1990), which features a combination of corian-
spicy formulations such as meat preparations. The essen- der (6%), nutmeg (2%), cardamom (0.5%), clove (0.7%),
tial oil is distilled from the berries of Piper nigrum. cinnamon bark (0.5%) and black pepper oil (1%). In Les
Belles: Delices d’Épices (Nina Ricci, 1999), cardamom,
dData from The Good Scents Company. cinnamon, clove and pepper were also combined.6
Caron’s Poivre (1954) included a spicy, peppery char-
acter, a floral heart note, and woody base notes. Also, in
1957, Caron launched Coup De Fouet – Eau de Cologne
Capsazepine F-3
Poivrée, a fragrance with a base of rose and peppery
undertones.
In the spicy-aromatic-musky male fragrance Extreme
Polo Sport (Ralph Lauren, 1998) ~6% black pepper oil
dominates the fragrance. The use of black pepper oil in
Contradiction (Calvin Klein, 1997) at 0.2% provides more
of a sparkling and piquant effect than a peppery note.
Black pepper oil has an intense, spicy and peppery
odor, reminiscent of cubebs (the dried unripe berry of an
Indonesian pepper shrub), but a milder taste that lacks
the pungency of the spice. An oil of pink pepper berries 3. J Peng and YJ Li, European J Pharmacology, 627(1–3), 1–7 (2010).
(Shinus molle), has been used in Pleasures (Estée Lauder, 4. L Faas, R Venkatasamy, RC Hider, AR Young and A Soumyanath,
British J Dermatology, 158(5), 941–950 (2008).
1995). It brings diffusivity, adds a creamy aspect, and
blends well with musks.6 5. PSW Leung, et al, Organic Letters, 12(21), 4996–4999 (2010).
6. P Kraft, JA Bajgrowicz, C Denis and G Frater, Angew Chem Int Ed, 49
References 39, 2980 (2000).
1. HB Heath, Source Book of Flavors, Van Nostrands Reinhold, New York
(1981).
2. FN McNamara, A Randall and MJ Gunthorpe, British J Pharmacology, To purchase a copy of this article or others,
144(6), 781–790 (2005). visit www.PerfumerFlavorist.com/magazine.

A reaction of piperonal and ethoxy acetyl bromide to create 3-benzo[1,3]dioxol-5-yl-acrylic acid ethyl ester F-4
flavor

Organoleptic Characteristics
of Flavor Materials
Judith Michalski, Senior Flavorist, Bell Flavors & Fragrances; judithmichalskillc@gmail.com

50 Taste: @ 10 ppm. Citrus, lemon, black peppery, slightly


Organoleptic Evaluation Panel terpeney and floral.
Possible applications: This is a very nice product for add-
• Judith Michalski
ing a twist to all citrus flavors and “blue” flavors such
• Tom Gibson, creative director, Silesia Flavors
as blueberry, Concord grape and plum. Tropicals will
• Carl Holmgren, consulting flavor chemist also benefit, especially rambutan, kiwi and lychee. Of
• Cyndie Lipka, flavor chemist, Sethness Greenleaf course, this is also a must for tea flavors of the Earl
• Gerard Mosciano, consulting flavor chemist Grey type.
• Robert Pan, senior flavorist, Bell Flavors & Fragrances Bontoux, Inc.; www.bontoux.com
• Susie Sadural, consulting flavorist
Natural occurrence information is from Leffingwell &
Bitter Orange Oil, Italian EE-54464
Source: Bontoux, Inc.
VOL. 36 NOVEMBER 2011

Associates. Suppliers of most materials found in this


FEMA#2823, CAS# 68916-04-1
report can be located in Allured’s Flavor & Fragrance
Natural
Materials, published in print and online
Odor: @ 100%. Fresh, peely, citrus/orange, slightly juicy
by Allured Business Media. Learn more at and aldehydic.
www.perfumerflavorist.com/ffm. Taste: @ 10 ppm. Sweet, fruity, juicy, peely, citrus/orange
Suppliers: Suggest materials for evaluation to and waxy.
Judith Michalski; judithmichalskillc@gmail.com. Taste: @ 20 ppm. Fresh, citrus/orange, peely, juicy and
waxy.
Possible applications: This material will enhance all citrus
Aniseed Oil, Andalousie EE-13214 flavors, especially orange, tangerine and grapefruit. It
Source: Bontoux, Inc. will also add an interesting twist to bubblegum flavors
FEMA# 2094, CAS# 8007-70-3 and other fruit blends.
Odor: @ 100%. Black licoricelike, rich, sweet, herbal, Bontoux, Inc.; www.bontoux.com
earthy and brown.
Taste: @ 5 ppm. Sweet, black licoricelike, rich, aniselike Black Pepper Oil, Madagascar EE-8799
and herbal with a molasses nuance. Source: Bontoux, Inc.
Taste: @ 10 ppm. Sweet, rich, black licoricelike, aniselike FEMA #2845, CAS# 8006-82-4
and herbal. Natural
Possible applications: This material presents a full-bodied Odor: @ 100%. Sweet with a cooling lift, spicy, fresh,
PERFUMER & FLAVORIST

profile, which will glorify the obvious anise, licorice and terpeney, woody, herbal and green.
sweet spice blends. At lower levels it can add interest Taste: @ 5 ppm. Sweet, green, black pepper bite, terpeney
to chocolate, brown sugar, root beer and mint types of and warm.
flavors. Taste: @ 10 ppm. Sweet, fresh, green, black pepper bite,
Bontoux, Inc.; www.bontoux.com terpeney, spicy, woody and warm.
Possible applications: The complex profile of this oil will
Bergamot Oil, Italian FCC B-11124 fit very nicely into a myriad of contrasting flavors.
Source: Bontoux, Inc. Savory spice mixtures for meats, vegetable, sauces and
FEMA# 2153, CAS# 8007-75-8 soups are the usual applications and a good fit for this
Odor: @ 100%. Sweet, green, black peppery, citrus, material. Other very good considerations lie on the
slightly floral and waxy. sweet side and include citrus complexes, mango, sweet
Taste: @ 5 ppm. Citrus, lemon, black peppery, green and spice blends, root beer, licorice, mints and anise.
floral. Bontoux, Inc.; www.bontoux.com
Ginger Oil Fresh, Madagascar EE-8578 Possible applications: Not only will mandarin and orange
Source: Bontoux, Inc. and other citrus flavors benefit from this material, but
FEMA# 2522, CAS# 8007-08-7 other anthranilate-containing flavors will as well,
Natural notably grape, blueberry and sweet wines.
Odor: @ 100%. Earthy, woody, freshly cut ginger note, Bontoux, Inc.; www.bontoux.com
citrus, sweet, spicy, terpeney and warm.
Taste: @ 5 ppm. Ginger, slightly citrus, warm spicy, slight Mandarin Oil, Red Italian EE-17775
bite with a hint of mustiness. Source: Bontoux, Inc.
Taste: @ 10 ppm. Ginger, warm spicy, slightly citrus, slight FEMA# 2657, CAS# 8008-31-9
bite and earthy. Natural
Possible applications: This is another lovely product for Odor: @ 100%. Aminelike, musty, peely, mandarin/orange
spice flavors and complexes that will also complement and slightly floral with a hint of grape.
other flavors such as citrus, mints, Sen-Sen, licorice, Taste: @ 10 ppm. Sweet, delicately citrus, mandarin/
root beer, cola and, of course, ginger ale. orange, peely and grapelike.
Bontoux, Inc.; www.bontoux.com Taste: @ 20 ppm. Sweet, fresh, juicy, peely and aldehydic.
Possible applications: Once the amine note dissipates, the
Lavender Oil, French EE-8563 deep, rich notes of this mandarin oil will enhance all
Source: Bontoux, Inc. citrus flavors, especially the top notes in orange juice. 51
FEMA# 2622, CAS# 8000-28-0 Like its green sibling it will also find good use in grape,
Natural blueberry and sweet wine flavors, as well as citrus
Odor: @ 100%. Sweet, floral, green, soapy, cooling and blends and fruit punches.
slightly citruslike. Bontoux, Inc.; www.bontoux.com
Taste: @ 2 ppm. Sweet, haylike, floral, tealike and slightly
citruslike. Peppermint Oil Fresh Absolute EE-10488
Taste: @ 5 ppm. Cooling, sweet, earthy, herbal, floral and Source: Bontoux, Inc.
slightly citruslike. GRAS, CAS# 84082-70-2
Possible applications: Although this material is primarily Natural
used in fragrance compositions, it will certainly bring Odor: @ 100%. Sweet, minty, cooling, candylike and
interesting depth to peach, apricot, blueberry, Concord green.
grape, plum, mint, honey and citrus flavors, especially Taste: @ 5 ppm. Green, leafy, sweet and fresh with just a
lemon and lime. It can also enhance tropical flavors like slight hint of cooling.
lychee, rambutan and longan. Taste: @ 10 ppm. Fresh, green, leafy, sweet and slightly
Bontoux, Inc.; www.bontoux.com cooling.
Possible applications: The expectation for peppermint
Mandarin Oil, Green Italian EE-13211 products is that cooling sensation, which is not present
Source: Bontoux, Inc. in this material at the concentrations at which it was
FEMA# 2657, CAS# 8008-31-9 evaluated. What is left is a product that is very fresh
Natural and refreshing that will add these notes to fruit,
Odor: @ 100%. Sweet, citrus/mandarin, candylike, peely, vegetable, bottled tea flavors and more without
slightly floral and grapelike. screaming mint.
Taste: @ 10 ppm. Sweet, citrus/mandarin/orange, candy- Bontoux, Inc.; www.bontoux.com
like and slightly grapelike.
Taste: @ 20 ppm. Citrus/mandarin/orange, slightly green, To purchase a copy of this article or others,
slightly floral, waxy and slightly grapelike. visit www.PerfumerFlavorist.com/magazine.
Progress in Essential Oils
Brian M. Lawrence, Consultant

52 Alaska Yellow Cedar Leaf Oil oil were -copaene, -ylangene, sabinene (0.1%)
longifolene, -cadinene, -cadinene, -pinene (1.3%)
On rare occasions, an oil of Alaskan
myrcene (2.2%)
cedar leaf (Chamaecyparis nootkaten- ar-curcumene, -curcumene, -cur-
-3-carene (30.8%)
sis (D. Don) Spach.) is produced cumene, -bisabolene, a-alaskene -terpinene (0.1%)
in North America and offered for (syn. acora-4,7-(11)-diene, -alaskene p-cymene (0.2%)
sale commercially. A survey of the (syn. acora-3,7(11)-diene) and limonene + -phellandrene (23.6%)
early literature reveals that the oil isomers of calamenene, -farnesene -terpinene (0.2%)
was thought to contain a-pinene, and nerolidol. He also characterized terpinolene (3.8%)
-pinene, sabinene, limonene and 10aH-muurola-4,6-diene that was nonanal (0.1%)
later (Andersen et al., 1973) given the camphor (0.6%)
p-cymene (Gildemeister and Hoffmann,
borneol (0.1%)
1956). trivial name 10-epi-zonarene.
terpinen-4-ol (0.5%)
Cheng and von Rudloff (1970) Andersen and Syrdal (1970)
VOL. 36 NOVEMBER 2011

-terpineol (0.2%)
compared the composition of Alas- reported the structure of - and citronellol (0.1%)
kan cedar leaf oil produced from -alaskene and determined that the piperitone (0.4%)
the leaves of young trees grown in a nerolidol found as a constituent of the (E)-anethole + U (0.1%)
greenhouse with oils produced from needle oil of C. nootkatensis was (E)- epi-cubebol + U (0.1%)
a 50–55-year-old tree and that of a nerolidol. (E)-nerolidol (0.2%)
1-epi-cubenol (0.1%)
commercial oil. All oils were pro- Andersen et al. (1972) determined
a-cadinol (0.5%)
duced by steam distillation, although the absolute stereochemistry cis- and
abietatriene (1.1%)
the distillation times were not given. trans-calamenene and found that they
U = unknown
The results of this comparative study were both components of Alaskan
are shown in T-1. Trace amounts cedar needle oil.
Trace amounts (<0.05%) of tri-
(<0.1%) of a-cubebene; a-copaene; The sesquiterpene fraction of the
cyclene, a-thujene, -phellandrene,
p-cymen-8-ol; isoprenyl senecoate; foliage oil of C. nootkatensis was de-
1,8-cineole, (E)- -ocimene, octanol,
pentadecane; prenyl tiglate or ange- termined (Banthorpe et al., 1977) to
-fenchol, trans-p-menth-2-en-1-ol,
late; nonadecane, tetradecanal, cedrol, contain the following components:
p-cymen-8-ol, methyl thymol, methyl
heneicosane, abieta-7,13-diene, dehy- longifolene (0.8%) carvacrol, -muurolene, a-muurolene
droabietadiene, pentacosane, 8,13-di- -copaene (2.1%) and -muurolol were also found in
epi-manoyl oxide and docosanal were -ylangene (2.5%) this oil.
also characterized in one or all of -cubebene (4.0%)
PERFUMER & FLAVORIST

these oils. ar-curcumene + -curcumene (24.6%) E. Gildmeister and Fr. Hoffmann, Die Ätherischen
Andersen and Syrdal (1970) and -bisabolol (3.8%) Öle. Vol. 4, p. 271, Akademie Verlag, Berlin,
Germany (1956).
Syrdal (1971) determined that a lab- -bisabolene (1.6%)
distilled needle oil of C. nootkatensis (E)-nerolidol (3.2%) Y-S. Cheng and E. von Rudloff, Gas-liquid
thujopsene (0.8%) chromatography of terpenes. XIX. Volatile oil
contained: of the leaves of Chamaecyparis nootkatensis.
Phytochemistry, 9, 2517–2527 (1970).
-pinene (34.0–36.7%) A needle oil of yellow cedar was N.H. Andersen and D.D. Syrdal, The alaskenes—
-pinene (2.0–2.3%) the subject of analysis by Lopes and Precursors of tricyclic sesquiterpenes.
myrcene (4.0%) Tetrahedron Lett., (26), 2277–2280
Kolodziejczyk (2003). The oil was
-3-carene (42.5–44.4%) (1970).
found to possess the following compo-
limonene (12.2–12.8%)
sition: N.H. Andersen and D.D. Syrdal, Terpenes
and sesquiterpenes of Chamaecyparis
In addition, the sesquiterpenes -pinene (13.9%) nootkatensis leaf oil. Phytochemistry, 9,
that were also characterized in this -fenchene + camphene (1.3%) 1325–1340 (1970).
D.D. Syrdal, Sesquiterpenes of Chamaecyparis behenic (C22) acid*** (0.1%) A sample of Ceylon citronella oil
nootkatensis. Isolation and structure bis-(2-ethylhexyl)-phthalate**** (2.0%)
determination. Absolute stereochemistry.
was reported (Anon., 2005) to possess
phthalate**** (1.7%) the following composition:
Chemical simulation of biogenesis. Ph.D.
thesis, Univ. Washington, Seattle, WA *does not occur naturally
(1971). **correct isomer not identified bornylene (0.05%)
***incorrect identification based on GC elution order tricyclene (1.34%)
N.H. Andersen, D.D. Syrdal and C. Graham, The
****plasticizer does not occur naturally -pinene (2.45%)
absolute stereochemistry of the calamenenes.
Tetrahedron Lett., (10), 905–908 (1972).

T-1
N.H. Andersen, D.D. Syrdal, B.M. Lawrence,
S.J. Terhune and J.W. Hogg, Widespread Comparative percentage composition of the leaf oils of
occurrence of two heteroannular dienes of Chamaecyparis nootkatensis
the cadalane skeleton. Phytochemistry, 12,
827–833 (1973).
Compound 1 2 3
D.V. Banthorpe, R.J. H. Duprey, J.F. Janes and
C.M. Voller, Distribution of Longibornane -pinene 33.8 33.0 38.8
sesquiterpenes 1. Re-examination of some camphene 0.3 0.2 0.5
reported sources. Planta Med., 31, 278–285 -pinene 2.4 2.6 2.0
(1977).
-3-carene 36.5 25.3 30.8
54
D. Lopes and P. Kolodziejczyk, Essential oils from myrcene 2.5 4.2 2.3
Western Canada. Poster presented at 34th
International Symposium of Essential Oils, limonene 12.1 23.5 9.2
Univ. Würzburg, Germany (2003). -phellandrene 1.3 2.8 2.9
p-cymene t 0.1 0.3
Ceylon Citronella Oil terpinolene 3.8 2.5 2.0
The so-called Ceylon citronella oil isoprenyl isovaleratea 0.2 0.3 0.4
(known as lenabata in Sinhalese) is nonanal 0.1 0.2 0.2
obtained by the steam distillation of prenyl isovalerateb 0.1 0.1 0.2
Cymbopogon nardus (L.) Rendle (syn. 3-methyl-3-butenyl tiglate or angelate* t 0.w3 0.2
Andropogon nardus L. var. nardus). bornyl acetate 0.2 0.2 0.2
Mahalwal and Ali (2003) analyzed terpinen-4-ol 0.1 0.7 0.2
an oil of C. nardus produced from thujopsene t t 0.1
VOL. 36 NOVEMBER 2011

dried grass collected in the Nilgiris -terpineol 0.5 0.1 0.5


Hills near Ootakamond (Tamil Nadu, -terpinyl acetate 0.9 0.3 1.2
India). The constituents characterized piperitone 0.1 0.2 0.1
in this oil were as follows: heptadecane t 0.1 t
-cadinene + -cadinene 0.1 0.1 0.1
-pinene (0.5%) citronellol t 0.1 0.1
-pinene (1.5%)
ar-curcumene - 0.1 t
myrcene (2.9%)
limonene (0.2%)
calamenene* t 0.1 0.1
cis-sabinene hydrate (3.8%) benzyl isovalerate 0.1 t 0.1
linalool (0.7%) 2-phenethyl isovalerate t - 0.1
citronellal (29.7%) nerolidol* 0.3 0.1 0.4
borneol (2.5%) benzyl tiglate, or angelate 0.1 t 0.1
isoborneol (1.1%) nonanoic acid - - 0.1
lavandulol (0.7%)
bisabolol* 0.3 0.3 0.7
-terpineol (0.5%)
-cadinol 0.1 t 0.3
-terpineol* (9.2%)
nerol (1.5%) isopimara-8(9),15-diene 0.1 0.1 0.1
geraniol (24.2%) 2-phenethyl tiglate, or angelate* 0.1 t 0.2
geranial (0.3%) isohibaene 0.1 0.3 0.1
eugenol (0.5%) sandarapimaradiene + isophyllocladene t 0.1 0.1
PERFUMER & FLAVORIST

-elemene (0.2%) isopimaradiene t 0.1 0.1


-caryophyllene (2.2%) tricosane t 0.1 t
-humulene (0.3%)
manoyl oxide + 13-epi-manoyl oxide 0.6 0.5 0.3
spathulenol (0.2%)
-selinene (0.8%)
phyllocladene 0.1 0.1 0.1
valencene isomer** (0.2%) 8-epi-manoyl oxide 0.5 0.5 1.1
valencene (0.5%) phyllocladan-16-ol 0.1 0.3 0.1
-selinene (1.0%) 1 = foliage oil from trees grown in greenhouse
selinene ** (0.3%) 2 = foliage oil from 50–55 year-old trees
3,3,5-trimethyl-1,5-heptadiene*** (0.7%) 3 = commercial sample of foliage oil
germacrene D-4-ol (1.5%) *correct isomer not identified
(E)-nerolidol (4.8%) t = trace (<0.1%)
aalso known as 3-methyl-3-butenyl isovalerate
hexadecanol (0.5%) balso known as 3-methyl-2-butenyl tiglate or angelate
arachidic (C21) acid*** (0.1%)
camphene (8.87%) spathulenol (0.01%) neral (0.3%)
sabinene (0.25%) 1-epi-cubenol (0.01%) geraniol (17.7%)
-pinene (0.25%) -eudesmol (0.06%) geranial (0.4%)
myrcene (1.21%) isoelemicin* (0.05%) bornyl acetate (0.5%)
-2-carene (0.19%) -cadinol (0.56%) citronellyl acetate (0.9%)
-phellandrene (0.29%) -eudesmol (0.14%) geranyl acetate (3.1%)
-terpinene (0.18%) farnesol* (0.02%) methyl eugenol (1.1%)
p-cymene (0.20%) geranyl hexanoate (0.13%) -elemene (1.0%)
limonene (9.68%) neophytadiene (0.02%) -caryophyllene (1.9%)
-phellandrene (0.65%) hexahydrofarnesyl acetone (0.01%) trans-a-bergamotene (0.9%)
1,8-cineole (0.20%) (E)-methyl isoeugenol (8.8%)
*correct isomer not identified
(E)- -ocimene (1.79%) germacrene D (1.6%)
2,6-dimethyl-5-heptenal (0.09%) -farnesene* (4.2%)
-terpinene (0.15%) Ranade (2008) reported that the -cadinene (1.1%)
octanol (0.05%) main constituents of Ceylon citronella elemol (1.6%)
terpinolene (0.95%) oil range in composition as follows: geranyl butyrate (1.1%)
camphenilone (0.09%)
*correct isomer not identified
linalool (0.65%) camphene (7–10%)
(E,E)-allo-ocimene (0.12%)
cis-p-menth-2-en-1-ol (0.06%)
limonene (7–11%)
citronellal (3–6%) V.S. Mahalwal and M. Ali, Volatile constituents of 55
a-campholenal (0.02%) Cymbopogon nardus (Linn.) Rendle. Flav.
borneol (4–7%) Fragr. J., 18, 73–76 (2003).
trans-p-menth-2-en-1-ol (0.06%) citronellol (3–8.5%)
citronellal (2.23%) geraniol (15–23%) Anon., GC-MS Analysis of Citronella Oil (Ceylon).
isopulegol (0.07%) Indian Perfum., 162 (2005).
methyl isoeugenol* (7–11%)
exo-methyl camphenilol (0.30%) G.S. Ranade, Profile: Essential Oils. Citronella
isoborneol (0.07%) *correct isomer not identified
Ceylon. FAFAI (Oct/Nov), 70 (2008).
borneol (5.49%)
terpinen-4-ol (0.54%) R.S. Verma, Laiq-Ur-Rahman, R.K. Verma, A.
Verma et al. (2009) compared Chauhan, A. Singh, A.K. Kukreja and S.P.S.
-terpineol (1.06%) the composition of oils produced in Khanuja, Qualitative performance of Java
myrtenol (0.09%) citronella (Cymbopogon winterianus Jowitt)
the laboratory by hydrodistillation
decanal (0.11%) cultivars in Kumaon Himalaya. J. Med.
from cultivars of C. winterianus over Arom. Plant Sci., 31, 321–325 (2009).
cis-piperitol (0.02%)
citronellol (1.89%) three seasonal times in the vicinity
M. Milchard, R. Clery, R. Esdale, L. Gates, F.
neral (0.38%) of Bageshwar (Uttarakhand, India). Judge, N. Moss, D.A. Moyler, A. Sherlock, B.
geraniol (27.85%) Examination of the data obtained Starr, J. Webb and E.J. Newman, Application
geranial (0.66%) revealed that the oil yield was highest of Gas-Liquid Chromatography to the
Analysis of Essential Oils. GLC Fingerprint
bornyl acetate (1.07%) (1.8%) during the summer harvest Chromatograms of Six Essential Oils.
geranyl formate (0.05%) (May) compared to 1.3% for plants Perfum. Flavor., 35(6), 34–40 (2010).
myrtenyl acetate (0.02%) harvested in December (winter) and
citronellyl acetate (1.08%) August (during monsoon season). A
-terpinyl acetate (0.04%) summary of the composite results of Spanish Oregano Oil
neryl acetate (0.03%) The oil of Spanish oregano is obtained
this study can be seen in T-2.
geranyl acetate (11.59%) from Thymus capitatus (L.) Hoffm.
A commercial oil of citronella
-bourbonene (0.02%)
produced in Sri Lanka from C. nardus et Link [syn. Coridothymus capitatus
-elemene (0.28%)
(L.) Rendle was the subject of analysis (L.) Reichenb. f.]. It has been valued
methyl eugenol (0.15%)
-caryophyllene (1.35%) by Milchard et al. (2010). The compo- for its richness in carvacrol, a com-
cis-a-bergamotene (0.18%) nents characterized in this oil were: pound whose antimicrobial activity
-sesquiphellandrene (0.01%) has created a renewed interest in all
(Z)- -farnesene (0.04%) tricyclene (1.3%) carvacrol-rich oils. In addition to the
(Z)-methyl isoeugenol (0.03%) -pinene (2.3%) fact that carvacrol is the main com-
-cubebene (0.02%) camphene (8.8%) ponent of the desired chemotype of
-humulene (0.18%) myrcene (0.9%) T. capitatus (oils rich in thymol are
-cubebene (0.02%) limonene (9.3%) also known), it also contains minor
germacrene D (0.03%) 1,8-cineole (0.5%) amounts of other phenols. The other
-amorphene (0.18%) (Z)- -ocimene (1.8%)
phenols were isolated by Kandil et
(Z,E)-a-farnesene (2.88%) (E)- -ocimene (1.1%)
al. (1994). In this study the author
(E)-methyl isoeugenol (0.94%) terpinolene (0.8%)
-farnesene* (0.41%) linalool (0.7%)
subfractioned an oil of T. capitatus of
-cadinene (0.38%) citronellal (4.5%) Egyptian origin. The phenols found
-cadinene (0.78%) neoisopulegol (1.2%) were 2-methyl-5-isopropyl-phenol
cadina-1,4-diene (0.01%) borneol (5.9%) (carvacrol), 5-methyl-5-isopropylphe-
a-cadinene (0.01%) terpinen-4-ol (1.3%) nol, 3-methyl-2,4-di-isopropylphenol,
elemicin (0.02%) -terpineol (1.3%) 5-methyl-2,3-di-isopropyl-phenol,
geranyl butyrate (0.79%) citronellol (3.5%) 3-methyl-2,3-di-isopropylphenol,
Comparative percentage composition of oils from five cultivars of Cymbopogon winterianus
produced at three separate times of the year in Uttarakhand T-2
Compound ‘Manjusha’ oil ‘Mandakini’ oil ‘Jalpallavi’ oil ‘Bio-13’ oil ‘Medini’ oil
myrcene 0.0–0.5 0.0–0.2 0.0–t 0.0–t -
limonene 4.1–5.6 1.8–3.6 3.3–5.7 3.2–4.3 -
(Z)-b-ocimene 0.0–t 0.0–t 0.0–t 0.0–t 0.0–t
p-cymene 0.0–t 0.0–t 0.0–t 0.0–t 0.0–t
6-methyl-5-hepten-2-one 0.0–t 0.0–t t–0.4 0.0–t 0.0–t
citronellal 28.3–37.3 27.7–34.8 34.9–40.0 35.4–42.5 11.0–18.9
linalool 0.6–0.8 0.6–0.8 0.6–0.8 0.6–0.8 0.7–0.8
linalyl acetate 0.1–0.2 t–0.3 0.1–0.3 t–0.2 t–0.2
b-elemene 0.3–0.4 0.3–0.5 0.3–0.7 0.4–0.6 0.5–1.3
b-caryophyllene 0.2–0.6 0.4–1.3 t–0.2 0.1–0.3 0.0–0.1
citronellyl formate 0.0–0.1 - - - 0.0–0.2
citronellyl acetate 3.1–5.9 2.4–4.6 2.8–4.3 2.9–3.8 1.4–1.8
56 neral 0.0–t 0.0–t 0.0–t 0.0–t 5.8–8.1
a-terpineol 0.4–0.6 0.4–0.6 0.4–0.6 0.6–0.7 -
geranyl formate 0.6–1.5 0.8–1.8 0.5–1.0 0.5–1.0 0.2–0.4
borneol t 0.0–t t–0.2 t–0.1 0.0–t
geranial 0.4–0.8 0.5–1.0 0.5–0.8 t–0.8 8.5–11.8
g-cadinene 1.0–1.5 1.2–2.2 0.9–1.4 0.9–1.6 t–0.2
geranyl acetate 4.4–9.3 4.1–5.3 5.3–5.9 4.6–6.4 4.9–6.0
citronellol 8.1–12.9 9.8–12.4 7.8–10.3 6.9–11.4 6.3–7.4
nerol 0.2–0.3 0.3–0.4 0.2–0.3 0.3–0.5 0.3–0.4
geraniol 20.9–23.5 18.8–23.2 18.6–23.4 18.4–24.7 41.6–45.7
caryophyllene oxide 0.0–2.2 0.0–2.0 0.0–1.9 0.0–1.8 0.0–0.5
elemol 5.5–9.6 5.6–8.1 3.7–7.1 3.3–7.6 1.8–5.2
VOL. 36 NOVEMBER 2011

a-cadinol - - - - -
t = trace (<0.1%)

5-methyl-2-isopropyl-phenol (thymol), In February, the plants are going ledene (0.1%)


3-methyl-2,5-di-isopropylphenol, through a dormancy period, whereas cadina-1(10),4-diene (0.1%)
2,5-di-isopropylphenol, 4-methyl-2,5- in August it is dry and hot and at the -caryophyllene (7.6%)
-humulene (0.2%)
di-isopropylphenol and 5-methyl-2,4- end of the flowering period.
-bisabolene (0.3%)
di-isopropylphenol. The authors also analyzed an
Hedhili et al. (2002) harvested oil that was produced from plants *correct isomer not identified
plants of T. capitatus plants growing harvested in June at the commence-
wild in the vicinity of Korba (Tunisia) ment of the flowering period. This oil, In addition, trace (<0.01%) amounts
monthly throughout the year. Oils which as analyzed by GC-FID and of -3-carene, limonene, a dihydrocar-
isolated from each harvest time were GC/MS, was determined to contain vone isomer, carvone and caryophyl-
examined for their main constituents. the following constituents: lene oxide were also found in this same
Over the year the oil yield ranged oil. The headspace volatiles obtained
from a low of 0.13% in February to a -pinene (0.3%)
from T. capitatus collected from
camphene (0.3%)
high of 2.0% in August. The content plants growing in their natural habitat
PERFUMER & FLAVORIST

sabinene (2.7%)
of the four major constituents of the in southern Italy was the subject of
-pinene (0.3%)
oil in February were found to be: examination by D’Auria et al. (2005).
myrcene (1.7%)
-terpinene (7.1%) -phellandrene (0.3%) Using SPME as their method of head-
p-cymene (24.0%) -terpinene (2.2%) space trapping followed by GC/MS,
carvacrol (38.3%) p-cymene (8.7%) the headspace was found to possess the
-caryophyllene (9.0%) -terpinene (16.4%) following composition:
-ocimene* (0.1%)
linalool (1.7%) -thujene (5.1%)
In contrast, the August oil contained:
terpinen-4-ol (0.9%) -pinene (2.4%)
-terpinene (5.7%) carvacryl acetate (0.1%) camphene (0.5%)
p-cymene (8.1%) thymol (0.2%) sabinene (1.1%)
carvacrol (71.8%) carvacrol (53.8%) 3-octanone (5.4%)
-caryophyllene (5.0%) aromadendrene (0.1%) ethyl hexanoate (1.3%)
-3-carene (0.5%) isobornyl acetate (0.1%) analyses the oil compositions can be
-terpinene (5.5%) thymol (0.4%) seen summarized as follows:
p-cymene (12.5%) carvacrol (62.6%)
1,8-cineole (2.1%) -caryophyllene (1.2%) -thujene (t–1.8%)
(Z)- -ocimene (0.1%) ffuranoid form -pinene (t–0.8%)
(E)- -ocimene (0.5%)
camphene (t–1.0%)
-terpinene (15.3%)
1-octen-3-ol (t–0.2%)
trans-sabinene hydrate (2.8%) Skoula and Grayer (2005) also -pinene (t–0.3%)
terpinolene (0.4%) analyzed the oil produced from plants myrcene (0.3–2.5%)
linalool (2.6%)
collected at a second site in Crete. -phellandrene (t–0.7%)
borneol (0.9%)
-terpineol (0.8%)
This oil, which was produced in -3-carene (t–0.2%)
2.79% yield, was found to be rich in -terpinene (0.1–2.7%)
cis-dihydrocarvone (0.2%)
p-cymene (3.0–17.0%)
cis-sabinene hydrate acetate* (0.1%) p-cymene (19.6%), -terpinene
-phellandrene (t–0.3%)
neral* (0.2%) (13.7%) and thymol (34.0%). limonene (0.1–0.5%)
geranial* (0.3%) An oil produced from Tunisian (Z)- -ocimene (t–0.1%)
thymol (20.3%) T. capitatus collected at the end of (E)- -ocimene (t–0.1%)
carvacrol (0.1%)
the flowering stage in August was -terpinene (0.7–16.5%)
eugenol (0.1%)
analyzed by Hedhili et al. (2005) using trans-sabinene hydrate (t–0.6%)
carvacryl acetate (0.1%)
-caryophyllene (8.0%) a combination of GC techniques. terpinolene (t–0.2%) 57
cis-sabinene hydrate (t–0.2%)
-humulene (0.4%) The components identified in this
linalool (0.3–1.9%)
allo-aromadendrene (17.0%) oil were: borneol (0.2–1.7%)
-elemene (0.1%)
terpinen-4-ol (0.3–0.8%)
-bisabolene (0.2%) -thujene (1.7%) thymol (0.3–12.7%)
(Z)- -bisabolene (0.1%) -pinene (0.9%) carvacrol (57.7–82.5%)
caryophyllene oxide (0.2%) camphene (0.4%) eugenol (t–0.3%)
-pinene (0.2%) carvacryl acetate (t–2.3%)
*incorrect identification based on GC elution order
myrcene (1.9%) -caryophyllene (0.9–4.4%)
-phellandrene (0.4%) aromadendrene (t–0.3%)
Trace amounts (<0.05%) of -terpinene (1.6%) -humulene (t–0.4%)
p-cymene (10.0%)
2-methylpentane, (E)-2-hexenal, viridiflorene (t–0.3%)
(E)- -ocimene (1.2%) -bisabolene (t–0.4%)
thuja-2,4(10)-diene, methyl carvacrol, -terpinene (11.7%) spathulenol (t–0.2%)
thymyl acetate, a-gurjunene, (E)- linalool (2.6%) caryophyllene oxide (0.1–1.2%)
-farnesene and d-cadinene were also carvacrol (53.7%)
found in the headspace. isocaryophyllene (0.5%)
Skoula and Grayer (2005) col- -caryophyllene (9.1%) Cultivated samples of T. capitatus
lected T. capitatus plants from Theriso aromadendrene (0.3%) were harvested from an experimental
germacrene D (0.4%) garden in Medenine (Tunisia) at two
(Crete, Greeece). Once dried they
-bisabolene (0.4%)
were hydrodistilled and the oil, which developmental stages by Zouari et al.
-cadinene (0.1%)
was produced in 4.6% yield, was -cadinene (0.3%)
(2007). Oils produced by hydrodistil-
analyzed by GC and GC/MS. The caryophyllene oxide (0.5%) lation were analyzed by GC and GC/
composition of this oil was found to be MS. The range in composition of the
as follows: oils produced from all harvest times
Bounatirou et al. (2006) collected can be seen as follows:
-thujene (1.3%)
aerial parts of T. capitatus plants dur-
-pinene (1.0%) ing the season at vegetative, flower- -thujene (0.4–1.9%)
camphene (0.5%) ing and post-flowering development -pinene (0.0–0.8%)
-pinene (0.2%) stages from three different locations, myrcene (0.9–2.2%)
3-octanone (0.1%) including Jendouba (interior north), -terpinene (1.0–3.0%)
myrcene (2.1%) Haouaria (littoral north) and Aintou- p-cymene (8.3–14.9%)
-phellandrene (0.1%) -terpinene (3.3–14.6%)
rine (littoral south) in Tunisia. Once
cis-dehydroxy linalool oxidef (0.1%) linalool (0.9–1.9%)
-terpinene (1.8%)
the plant materials were air-dried they borneol (0.0–0.6%)
p-cymene (13.5%) were hydrodistilled and the oils were terpinen-4-ol (0.7–1.0%)
limonene (0.4%) analyzed by GC-FID and GC/MS. thymol (0.3–0.5%)
-phellandrene (0.2%) The authors found that oils produced carvacrol (47.4–66.3%)
-terpinene (7.4%) from plants collected at different -caryophyllene (1.8–4.7%)
cis-sabinene hydrate (0.1%) developmental stages showed chemi- carvacryl acetate (0.0–2.4%)
terpinolene (0.2%) caryophyllene oxide (1.3–2.2%)
cal homogeneity regardless of the
linalool (0.1%)
trans-sabinene hydrate (0.4%)
influence of extrinsic conditions such
borneol (0.7%) as collection site location, altitude, cli- Thymus capitatus plants collected
terpinen-4-ol (3.5%) mate including temperature, humid- in the vicinity of Tetouan (northern
-terpineol (0.2%) ity and rainfall. Examination of all of Morocco) were hydrodistilled in the
thymoquinone (0.1%) the data presented for the numerous laboratory by El Ajjouri et al. (2008).
Analysis of the oil by GC-FID and cis-a-terpineol** (0.1%) L. Hedhili, M. Romdhane, H. Planche and M.
-caryophyllene (1.3%) Abderrabba, Towards gas chromatography-
GC/MS revealed that it contained the mass spectrometry coupling protocols for
thymol (0.2%)
following components: both identifying and quantification essential
carvacrol (78.0%)
oils of Thymus capitatus Hoff. et Link. J.
-thujene (1.9%) *does not exist naturally Chromatogr., 1064 A, 129–134 (2005).
-pinene (0.8%) ** compound cannot exist
S.B. Bounatirou, S. Zouari, A.C.S. Figueiredo,
camphene (0.1%) J.G. Barroso, L.G. Pedro, M. Neffati, M.N.
-pinene (2.5%) Marongiu et al. (2010) screened a Rejeb and S. Smiti, Chemical homogeneity of
-phellandrene (0.3%) supercritical CO2 extract of T. capi- Thymus capitatus Hoff. et Link. essential oils
from Tunisia. Rev. Regions Arides (Numero
-3-carene (1.4%) tatus plants that were collected from Speciale) Acetes Seminaire Internat. Plant.
p-cymene (6.3%) their natural habitat in the vicinity of Parfum, Aromat. Medicin., (SIPAM), pp
-terpinene (4.9%) Sadali (Sardinia, Italy). The extract, 679–686 (2006).
terpinolene (0.1%) which was analyzed using both GC- S. Zouari, R. El Ferjani, Z. Ghrabi and M. Neffati,
linalool (3.9%) FID and GC/MS, was found to con- Effet de la mise en cultare du stade de
borneol (0.9%) developpement et du mode d’exploitation
tain the following major components:
thymol (0.4%) sur la teneur et la composition chimique
carvacrol (70.9%) p-cymene (2.2%) de l’huile essentielle du thym en capitule
(Coridothymus capitatus (L.) Reichenb.). J.
-caryophyllene (3.6%) -terpinene (0.7%)
58
Soc. Chim. Turk., 9, 9–16 (2007).
linalool (1.0%)
M. El Ajjouri, B. Satrani, M. Ghanmi, A. Aafi,
borneol (0.5%)
Galego et al. (2008) analyzed an oil carvacrol (87.8%) A. Farah, M. Rahouti, F. Amarti and M.
produced from T. capitata [syn. T. capi- Aberchane, Activité antifongique des huiles
-caryophyllene (2.3%) essentielles de Thymus bleicherianus Pomel
tatus, Thymbra capitata (L.) Griseb.] et Thymus capitatus (L.) Hoffm. and Link
produced from plants obtained from an Trace amounts (<0.1%) of contre les champignons de poursiture du bois
experimental garden in Algarve (Portu- -pinene, camphene and -pinene d’oeuvre. Biotechnol. Agron. Soc. Environ.,
12, 345–351 (2008).
gal). Using GC-FID and GC/MS as the were also characterized in this extract.
method of analysis, the composition of L. Galego, V. Almeida, V. Goncalves, M. Costa,
the oils was found to be: O. Kandil, N.M. Radwan, A.B. Hassan, A.M.M. I. Monteiro, F. Matos and G. Miguel,
Amer, H. A. El-Banna and W.M.M. Antioxidant activity of the essential oils
-thujene (1.5%) Amer, Extract and fractions of Thymus of Thymbra capitata, Origanum vulgare,
capitatus exhibit antimicrobial activities. J. Thymus mastichina and Calamintha baetica.
-pinene (0.6%)
Ethnopharmacol., 44, 19–24 (1994). Acta Hort., 765, 325–333 (2008).
VOL. 36 NOVEMBER 2011

camphene (0.1%)
-pinene + sabinene (0.2%) L. Hedhili, M. Romdhane, A. Abderrabba, H. B. Marongiu, A. Piras, S. Porcedda, D. Falconieri,
myrcene (1.7%) Planche and I. Cherif, Variability in essential A. Maxia, M.A. Frau, P. Molicotti and
oil composition of Tunisian Thymus capitatus S. Zanetti, Composition and biological
-terpinene* (1.2%)
(L.) Hoffmanns et Link. Flav. Fragr. J., 17, activity of supercritical CO2 extract of some
limonene (2.6%) 26–28 (2002). Lamiaceae growing wild in Sardinia (Italy).
cis-sabinene** (0.2%) J. Essent. Oil Bear. Plants, 13, 625–632
(E)- -ocimene (4.8%) M. D’Auria, G. Mauriello, R. Marino and R. (2010).
Racioppi, Composition of volatile fractions
1,8-cineole (0.3%)
from Thymus, Origanum, Lavandula and
g-terpinene (5.4%) Acinos species. J. Essent. Oil Bear. Plants,
terpinolene (0.1%) 8, 36–51 (2005).
trans-sabinene hydrate (0.6%)
linalool (0.7%) M. Skoula and R.J. Grayer, Volatile oils of
Coridothymus capitatus, Satureja thymbra,
cis-sabinene hydrate (0.2%) Satureja spinosa and Thymbra calostachya
terpinen-4-ol (0.6%) (Lamiaceae) from Crete. Flav. Fragr. J., 20, To purchase a copy of this article or others,
borneol (0.2%) 573–576 (2005). visit www.PerfumerFlavorist.com/magazine.
PERFUMER & FLAVORIST
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Our readers seek out P&F magazine’s
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pcrist@allured.com or 1-630-344-6060.
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62
VOL. 36 NOVEMBER 2011
PERFUMER & FLAVORIST

To reserve space in this section, contact Paige Crist at pcrist@allured.com or call 1-630-344-6060.
Advertiser Web site Page
Alluredbooks www.Alluredbooks.com 15, 30, 35, 37, 51, 58
Axxence Aromatic GmbH www.axxence.com 21

ad index
Bedoukian Research, Inc. www.bedoukian.com 29
Berje, Inc. www.berjeinc.com 7
Bontoux Inc www.bontoux.com 47
Citrus & Allied Essences Ltd. www.citrusandallied.com 5
Creative Flavours Fragrances www.vka.com 59
Firmenich, Inc. www.firmenich.com 1
Flavodor Flavors & Fragrances BV www.flavodor.nl 27
Flavor & Fragrance Materials www.PerfumerFlavorist.com/FFM 62
Fleurchem, Inc. www.fleurchem.com 19
Givaudan www.givaudan.com 3
Hangzhou Grascent Co., Ltd. www.grascent.com 43
Indukern www.indukern-ffingredients.com 32-33
Lansdowne Chemicals Plc www.lansdownechemicals.com 31
Mane USA www.mane.com 39
Mitsubishi Gas Chemical America, Inc. www.aromaticchemicals.com 37 63
Moellhausen SpA www.moellhausen.com 53
Natural Advantage www.natural-advantage.net 13
Penta Manufacturing Co. www.pentamfg.com Cover 4
Som Extracts Limited www.somextracts.com 45
Sonarome Pvt. Ltd. www.sonarome.com 25
Symrise www.symrise.com Cover 2
Treatt PLC/Treatt USA www.treatt.com 17
Vigon International, Inc. www.vigoninternational.com Cover 3
Wanxiang International www.wxintl.com 23

VOL. 36 NOVEMBER 2011


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1. Publication title: Perfumer & Flavorist
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the last word...
Last Word: Vanilla, Ethics, and Market Drivers
A conversation with Scott May, VP, global sweet goods, Givaudan

“D
espite that most natural “We’ve taken a holistic approach with
material prices have gone everything going on in Madagascar [grow-
through the roof in the last ing communities], because it’s such a big
several years, vanilla has remained quite chunk of the overall global supply,” says
stable,” says Scott May, VP of sweet goods May, adding that other traditional growing
at Givaudan. This stability has resulted from regions such as India and Indonesia have
a recent oversupply of natural product, and fallen away due to competition from more
a recent lack of natural disasters in growing lucrative crops. The goal is to help local
regions. As a result, says May, vanilla supply communities thrive while making vanilla
has equaled or exceeded market demand. cultivation and production a sustainable
64 “There’s a lot of inventory out there that
people are carrying; I don’t think prices are
business. “We’ve got to invest in Mada-
gascar to ensure that they’re going to be
going to [escalate significantly] unless there’s around for a very long time,” says May.
some sort of natural disaster.” Of course May “One of the things we found early on was
and his colleagues are knocking on wood. the fact that the [local] government really
May explains that vanilla prices have doesn’t have the ability to fund an educa-
benefited from steady, but manageable tion program in Madagascar. The schools
growth in demand, in addition to regional preferences for in the villages where vanilla is grown were in disrepair. We
non-natural vanilla flavors. “Vanilla flavors using vanilla wanted to make sure [locals] had school facilities that were
extract are only [common] in Western Europe, the United adequate so they could have the children in the villages
States, the developed markets of Asia-Pacific such as Japan, going to school, being educated, so they could continue
and Australasia,” he says. “If you look at developing coun- growing as a [community].”
tries, those flavors are all typically artificial and don’t [tend Next came a focus on food crops. “We wanted to improve
VOL. 36 NOVEMBER 2011

to] rely on vanilla extract. There is growth for vanilla in the not only how [locals] grow the vanilla, which is their only
developing markets, but it’s not really pulling on the extract cash crop, but also rice, which is what they use to sustain
side. Consumers in the developing markets are so used to themselves,” May explains. “Growing rice is not an easy
the vanillin- and ethyl vanillin-type of profiles that I don’t thing to do—they spend the majority of their time [culti-
believe we’ll see consumers move in the same direction as vating it]. So we put together a program that helped them
the United States and Western Europe.” While May doesn’t improve their yield in their existing rice paddies by as much
preclude the possibility that developed market-type natural as 50%, without cutting down any more forest.”
vanilla flavors in products such as ice cream could spur new Having reinforced the infrastructure of growing commu-
demands in developing markets, pricing constraints will still nities, the company then focused on traceability, the keystone
reign in demand. of any ethical sourcing program. “If a customer is looking to
“The [annual vanilla flavor] growth we’re seeing in Western have full traceability from their extract all the way to where
Europe and the United States is [but a few] percent, which the beans were grown and the farmer who grew them, we
is about what the flavor market in total is growing,” May can actually provide that,” says May. “Our customers have
continues. “I don’t see a huge increase in the use of vanilla been asking for the ability to have complete traceability for
extracts at this point. Where you do see growth is a move the supply chain of vanilla. They’re looking to make it part of
from more traditional extracts to ethically sourced, traceable, a requirement of supply. If you’re familiar with the Madagas-
high quality [options].” car supply chain, you know it’s not easy. You may have 1,000
Givaudan’s ethical sourcing program for vanilla—part vanilla farmers in one growing region. Each one has a very
of a larger sustainability initiative that has focused on key small plot. You can imagine that as they start collecting these
PERFUMER & FLAVORIST

materials such as sandalwood from Australia, tonka beans beans and during the curing process you lose that traceability
from Venezuela, benzoin from Laos, and ylang ylang from if you don’t have some type of program [set up]. You have to
Mohéli—pushes beyond facets of traceability and sustain- have a program that includes the farmers, the collectors, the
ability, focusing on support for local growing communities. exporters—the net program has to encompass all of those.”
In addition to traceability, quality is crucial. And so
Givaudan has experts working with the local supply chain
This conversation brought to you by: to optimize planting, Fusarium root rot treatment and
curing. “The right procedure for curing the vanilla bean is
important for delivering the right quality of vanilla,” says
May. “We’re working on a controlled curing process that
will enable us to take it to the next level. We’re going to be
working with the farmers and collectors on implementing
that in the coming years.”
We make it happen . . . together.