FLAVORS AND

FRAGRANCES
Chapter 7.1
benjaminlukas@yahoo.com

Definition
Fragrance & flavors substances
Strong smelling organic compound with
pleasant odor
Uses in : perfume & perfumed product
Food flavoring
beverages
Fragrance & flavor are chemical
messengers with the receptor are
olfactory cells in the nose and in the
tongue

Physiological importance
Chemical signals are very important for
organisms for the following:
to hunt for and inspect food
to detect enemies and harmful object
to find members of the opposite sex
to find the way
For human the important of flavor and
fragrance substances are not as
drastic as for other mammals
The use of fragrance for human is for
invoking pleasurable sensation
For flavor example added for food is
enhancing the enjoyment of food

Natural, Nature Identical,

Artificial Product
Natural Products are obtained
from plant or animal.

Nature Identical Products are

produced synthetically but are
chemically identical to their
natural counterparts
Artificial Products are
compounds that have not been
identified in plant or animal
product

Problems of Using Natural

Flavors

1) Many natural flavor have low intensity,

and hence it is
used at a high dosage which results in an
unsatisfactory texture and poor stability.

2) Concentration of natural flavors is usually

accompanied by significant changes in the
flavor
profile.

3) Natural flavors exhibit variations in

strength and quality.

Problems of using Natural

Flavors

4)The supply of natural materials is becoming

uncertain.

5) Most natural flavors are unstable and undergo

changes during postharvest handling, processing
or
storage.

6) Many natural products contain enzyme systems

which may result in the formation of off-notes.

7) The toxicity of many natural products has yet

to be
established.

Disadvantage using Imitation

Flavors
1) Original natural flavor more subtle,
imitation flavor maybe described as
he i al

2) Diffi ulties i

la eli g

3) Many natural flavors have a built in reservoir

of flavor precursors which can result in the
generation of additional flavor, imitation
flavors are not.
4) Imitation flavor generally require the use of
either a
solvent or a carrier

5) Restriction by legislation
6) Problems with texture in the end product

Advantage of Imitation
Flavor
1) Cheaper than natural flavor
2) Stable

3) Can be designed to withstand

severe processing condition
4) Can be produced in a variety of
forms (e.g., alcoholbased, oil-based, or encapsulated
powders )
5) Generally readily available
6) Consistency of quality

Aromatics Sources
Plants have long been used in
perfumery as a source of
essential oils and aroma
compounds. A plant can offer
more than one source of
aromatics, for instance the aerial
portions and seeds of coriander
have remarkably different odors
from each other. Orange leaves,
blossoms, and fruit zest are the
respective sources of petitgrain,
neroli, and orange oils.

Plant Source

Bark: eg cinnamon,
cascarilla, sassafras , safrole.
Leaves and twigs: lavender ,
patchouli, sage, violets,
rosemary, and citrus, hay
and tomato leaf.

Plant Source
Flowers and blossoms:

rose, jasmine, as well as

osmanthus, plumeria,
mimosa, tuberose,
narcissus, scented
geranium, cassie, ambrette
as well as the blossoms of
citrus and ylang-ylang, clove
, vanilla.

Plant Source
Fruits:

Fresh fruits such as apples,

strawberries, cherries,
litsea cubeba, vanilla, and
juniper berry. The most
commonly used fruits yield
their aromatics from the
rind; they include citrus
such as oranges, lemons,
and limes, grapefruit.

Plant Source
Resins:
Valued since antiquity, resins
have been widely used in
incense and perfumery.
Commonly used resins in
perfumery include labdanum,
frankincense/olibanum,
myrrh, Peru balsam, gum
benzoin. Pine and fir resins
and fossil conifers.

Plant Source
Roots, rhizomes and bulbs: Commonly
used terrestrial portions in perfumery
include iris rhizomes, vetiver roots,
various rhizomes of the ginger family.
Seeds: Commonly used seeds include
tonka bean, carrot seed, coriander,
caraway, cocoa, nutmeg, mace,
cardamom, and anise.
Woods: Commonly used woods include
sandalwood, rosewood, agarwood,
birch, cedar, juniper, and pine.

Different Oils from different

Parts of plant
SOURCES OF ESSENTIAL OILS
BITTER ORANGE TREE
FLOWER

FRUIT

LEAVES AND
TWIGS

DISTILLATION
NEROLI OIL

EXPRESSIONBITTER ORANGE OIL

DISTILLATIONPETIGRAIN OIL

EXTRACTIONORANGE FLOWER
ABSOLUTE

EXTRACTIONPETITGRAIN
ABSOLUTE

Clove Oil Derivatives

O

CH3

O
H
H 3C

O
HO

CH2

CH3

O
O
H3C

O
O

HO

O
H
H 3C

HO

CH2

CH3

Distillation
HO

Fractionation
Acetylation
Isomerisation
Methylation
Hydrogenation
Oxidation
Mild Acid Reaction
Benzylation

Animal Sources
Civet: Also called Civet Musk,
this is obtained from the
odorous sacs of the civets,
animals in the family
Viverridae, related to the
mongoose.
Hyraceum: Commonly known
as "Africa Stone", is the
petrified excrement of the Rock
Hyrax. [13]

Animal Source
Honeycomb: From the honeycomb of the
honeybee. Both beeswax and honey can be
solvent extracted to produce an absolute.
Beeswax is extracted with ethanol and the
ethanol evaporated to produce beeswax
absolute.

Deer musk: Originally derived from the

musk sacs from the Asian musk deer, it has
now been replaced by the use of synthetic
musks sometimes known as "white musk".

Animal Source
Ambergris: Lumps of oxidized fatty
compounds, whose precursors were
secreted and expelled by the sperm
whale. Ambergris should not be
confused with yellow amber.

Castoreum: Obtained from the

odorous sacs of the North American
beaver.

Synthetic Sources
Many modern perfumes
contain synthesized
odorants.

Synthetics can provide

fragrances which are not
found in nature. For
instance, Calone, linalool
and coumarin

Methods in synthetic
Flavor/Fragrance Reconstitution
Isolation of flavor concentrate

Separation of components
Identification
Synthesis
Scientifically reconstituted formulation
(match with GC)
Organoleptically adjusted formulation
Process and product development
Manufacture and end use in consumer
product

Limitations
a. Some compounds
decompose or do
not come out of GC
b. Wide variety of
flavor threshold
(Some compounds
can not be
identified.

ODOR AND STRUCTURE

Different
compound may
have similar odor
But small changes
in structure may
change the
intensity of an
odor by several
order of
magnitude

Volatility
Fragrances must be volatile, so
therefore the molecular mass
of the fragrance molecule is an
important factor.
Perfume consists of mixture of
fragrance compounds which
are different in volatility
Perfume is devided into the
Top note, Middle note and the
End note.
Sometime substances are
added to perfume to prevent
the more volatile component
for evaporating too rapidly

FRAGRANCE NOTES

Top notes:
The scents that are perceived
immediately on application of a
perfume. Top notes consist of
small, light molecules that
evaporate quickly. They form a
person's initial impression of a
perfume and thus are very
important in the selling of a
perfume. Also called the head
notes.

FRAGRANCE NOTES
Middle notes or Heart Notes :
The scent of a perfume that emerges just prior to when the top
notes dissipate. The middle note compounds form the "heart" or
main body of a perfume and act to mask the often unpleasant
initial impression of base notes, which become more pleasant with
time. They are also called the heart notes.

FRAGRANCE NOTES
Base notes:
The scent of a perfume that
appears close to the departure
of the middle notes. The base
and middle notes together are
the main theme of a perfume.
Base notes bring depth and
solidity to a perfume.
Compounds of this class of
scents are typically rich and
"deep" and are usually not
perceived until 30 minutes after
application.

FRAGRANCE NOTES

The scents in the top and

middle notes are influenced by
the base notes, as well the
scents of the base notes will be
altered by the type of fragrance
materials used as middle notes.

Manufacturers of perfumes
usually publish perfume notes
and typically they present it as
fragrance pyramid, with the
components listed in
imaginative and abstract terms.

Odor description
An odor can be described by adjectives which relate them
to other products with similar odor
woody

General for odor or food e.g sandalwood

waxy

Smell like candle wax

spicy

General for odor of spices

resinou
s

Aromatic odor of tree exudate

powder Smell associated with talcum

y
mossy

Smell of forest and seaweed

minty

Peppermint / like odor

metallic Smell like metal surface

herbac
eous

Smell like green herbs

green

Typical odor of freshly cutgrass and leaf

Odor Description
fruity

General for odor of food

floral

General for odor of flowers

fatty

Odor resemble animal fat

and tallow

citrus

Fresh odor of citrus fruits

balsamic

Heavy sweet odor e.g

cocoa, vanilla, cinnamon

earthty

Humus like, of humid earth

Isolation of natural fragrance

and
flavor concentrate

Three main methods use to obtain concentrates

of plan flavor and fragrance substances :
1.Distillation
2.Mechanical separation (pressing)
3.Solvent extraction

DISTILLATION

Distillation:
A common technique for obtaining aromatic
compounds from plants, such as orange blossoms
and roses. The raw material is heated and the
fragrant compounds are re-collected through
condensation of the distilled vapour.

Steam distillation:
Steam from boiling water is passed through the raw
material, which drives out their volatile fragrant
compounds. The water collected from the
condensate, which retains some of the fragrant
compounds and oils from the raw material is called
hydrosol and sometimes sold. This is most
commonly used for fresh plant materials such as
flowers, leaves, and stems.

DISTILLATION
Dry/destructive distillation:
The raw materials are directly
heated in a still. Fragrant
compounds that are released
from the raw material by the
high heat often undergo
anhydrous pyrolysis, which
results in the formation of
different fragrant compounds.
This method is used to obtain
fragrant compounds from
fossil amber and fragrant
woods.

DISTILLATION
Fractionation:

Through the use of a

fractionation column,
different fractions can be
selectively excluded to
modify the scent of the
final product. This is
sometimes performed to
remove unpleasant
scents of a material with
certain purpose.

EXTRACTION

Maceration/Solvent extraction:
The most used and economically
important technique with raw materials
are submerged in a solvent. Maceration
lasts anywhere from hours to months.
Fragrant compounds for woody and
fibrous plant materials are often
obtained in this manner as are all
aromatics from animal sources. The
technique can also be used to extract
odorants that are too volatile for
distillation or easily denatured by heat.
Commonly used solvents for
maceration/solvent extraction include
hexane, and dimethyl ether.
The product of this process is called a
"concrete".

EXTRACTION
Supercritical fluid extraction:
A technique for extracting fragrant
compounds from a raw material,
which often employs Supercritical
CO2 with low heat of process and the
relatively nonreactive solvent used in
the extraction.
Ethanol extraction:
Used to extract fragrant compounds
directly from dry raw materials, as
well as the impure oily compounds
materials resulting enfleurage.
Not used to extract fragrance from
fresh plant materials .

EXTRACTION

Enfleurage:
Absorption of aroma materials into
solid fat or wax and then extracting the
odorous oil with ethyl alcohol.
Extraction by enfleurage was
commonly used when distillation was
not possible because some fragrant
compounds denature through high
heat. This technique is not commonly
used in the present day industry due to
its prohibitive cost and the existence of
more efficient and effective extraction
methods. [9]

Expression

Expression:
Raw material is
compressed to obtain
the oil.
The only fragrant oil
from the peels of fruits
is in the citrus family
extracted in this
manner .

FLAVORS AND
FRAGRANCES
Chapter 7.2
benjaminlukas@yahoo
.com

Extracts
According to the method of preparation, the extracts of
fragrance & flavor substances obtained from plants can
be classified as essential oils, pomades, concretes,
absolutes, resinoids, oleoresins and tinctures
Of these extracts only essential oils, absolutes and
tincture are used directly to formulate perfumes

Steam distillation unit

Essential Oil
Essential oil:
Fragrant materials that have been extracted from a source
material directly through distillation or expression and
obtained in the form of an oily liquid. Oils extracted
through expression are sometimes called expression oils.

Essential oils
Raw materials : various parts of plants

Production : essential oils are obtained from plant materials by distillation. After condensation the oil separate
from the aqueous phase is removed. The yield ranges from point 1 % to a few %

Essential oil consists of volatile compounds which are mainly hydrocarbons or mono functional compounds

Essential oils do not leave a grease stain

Individual compound can be isolated from essential oil containing 1 or few major components

Essential oil can be converted as a whole into derivatives

Pomades
Fats that contains fragrances
substances which are produced by
hot or cold enfleurage of flowers.
Hot enfleurage - in this method
flowers or other parts of a plant
are directly immersed in liquid or
molten wax
Cold enfleurage the volatile
components are released by the
flowers into surrounding are
absorbed with fat over along
period of time
This method is to produce high
grade flower concentrate

Concretes
These are prepared by
extracting fresh plant
materials with non polar
solvents which are then
evaporated.
Concretes contains not only
volatile fragrance materials,
but also a large proportion of
not volatile substances and
are therefore not completely
soluble in alcohol.

Absolutes
These are prepared by mixing concrete with ethanol followed by
cooling.
The precipitated formed are removed and then ethanol is
evaporated to produce an absolute.
Absolutes are complete to soluble in ethanol
The yield is about 50% of the concrete use.

Resinoids
These are prepared by
extracting plant exudates
with solvent such as ethanol,
methanol or toluene.
The yield range from 50% to
95% with the product highly
viscous.
Resinoids consist of non
volatile compounds
Uses : as fixative

Tinctures and Oleoresins

Alcoholic solutions which are prepared
by treating plant materials with ethanol
or ethanol water mixtures.
Tinctures also called infusions
Oleoresins : these are concentrates
prepared from spices ( e.g. pepper,
ginger and vanilla) by solvent extraction
Pepper and ginger oleoresins contain
not only volatile aroma compounds but
also substances responsible for
pungency.
Very often oleoresins are obtained by
extraction with carbon dioxide

Banned Essential Oils

Oil

Action

Oil

Action

Cade Oil
Crude

Carcinoge Styrex
Gum
nic

Sensitizer

Calamus

Carcinoge Verbena
nic
Oil

Sensitizer

Sassafras

Carcinoge Tea
nic
Absolute

Sensitizer

Costus
Root

Sensitizer Peru
Balsam

Sensitizer

Elecampa Sensitizer Horseradi Toxic and

ne
sh Oil
Iritant
Fig Leaf
Absolute

Sensitizer Mustard
Oil

Toxic and
Iritant

Therapeutic Uses of Ess. Oils

Oil

Action

Basil

Depression, headache and migraine

Bergamot

Skin Stress

Black Pepper

Muscular ache and pains

Citronella

Insect repellant

Clove

Antispasmodic, antiseptic

Lavender

To calm and relax , to soothe headache

and migraine

Jasmin, Rose, Sandalwood, Ylang-ylang

Aphrodisiacs

Tea Tree, Eucalyptus, Sandalwood &

Thyme

Antiseptic, antimicrobial and disinfectant

Yarrow

Joint inflammation

Physiological Effects of Ess. Oils

Oil

Action

Bergamot

Lack of confidence and courage, depression, wory,

nervous tension, anxiety and grief

Benzoin

Nervous anxiety, depression, worry, grief and loneliness

Cypress

Bereavement, confusion, regret, emotional instability,

impatience, mood swing, sorrow , irritability and
withdrawal

Eucalyptus

Bitterness, Guilt, loneliness, moodiness and resentment

Peppermint

Depression and mental fatigue

Geranium

Anxiety, confusion, depression, mental lethargy,

moodiness, sadness and tearfullness

Essential oil
Essential oil

Plants

Method of prep

Main component

Garlic oil

Garlic bulb

Steam distillation

Diallyl disulfide

Onion oil

Onion bulb

Steam distillation

Cis and trans-propenyl

propyl disulfide

Ambrette seed oil Abelmoschus

moschatus seed

Steam distillation

5-tetradicen-14olide,farnesol and
farnesyl acetate very
expensive e.oil

Amyris oil ( mild

wood odor)

Amyris balsamifera
wood

Steam distillation

Sesquiterpenoids, used as
fixative

Angelica oil (
green herbasious
pepperymusklike
odor)

Angelica arc
angelica

Steam distillation of
root or seed

Sesquiterpenoids and
terpenenoids

Anise oil (sweet

Pimpinella
odor of anethole) anisum

Steam distillation

Transanethole,used for
flavoring food, beverages
and oral hygene product

Artemisia oil (
light herbacius
odor)

Artemisia asso

Steam distillation

ketone camphor and

thujone, used in fine
fragrance

Basil oil

Basil

Steam distillation of
ocimum bacilicum to
produce reunian basil oil
and steam distillation of
european basil species to
produce european basil
oil

Estragole in reunion basil

oil ( > 80%).Linalool (35%50%) and estragole ( 15%
25%)

Bay Oil

Pimenta race
mosa leaves (
strong spicy
clove like
odor)

Steam distillation

Eugenol,chavicol,myrcene
used for perfuming after
shave lotion

Benzoe Sumatra
resinoids (sweet
balsamic odor)

Styrax
benzoin
dryand

Solvent extraction

Vanillin, benzoic &

cinnamic acids

Essential oil

Plants

Method of prep

Main component

Bitter almond oil (

almond like cherry
aroma)

Prunus
amygdalus seed

Steam distillation

Benzaldehyde

Blackcurrant absolute

Blackcurrant

Solvent extraction
from the bud

4-methoxy2methyl2butenethiol

Buchu leaf oil ( minty

fruit odor )

Barosma betulina Steam distillation of

leaf

p-menthane-8thiol-3-one used in
the colonge

Calamus oil ( spicy

aromatic odor)

Acorus calamus

Steam distillation of
roots

b-asarone

Camphor oil / eucaliptus Cinnamomum

oil
camphora

Steam distillation of
the wood

ciniole

Caraway oil ( mild spicy

caraway odor)

Steam distillation of
seed

Lemonene &
cavone,used for
flavoring food &
alcohol beverages

Carvum carvi

Cardamon oil (strong

aromatic camphoraceus
odor)

Elettaria
cardamomum

Steam distillation
of the seed

1,8-ciniole and
terpenyl acetate
used for flavoring
food

Carrot seed oil (pleasant

aromatic odor)

Daucus carrota

Steam distillatin of
seed

Carrotol, used as
food flavor and in
alcoholic beverages

Atlascedar oil (sweet

woody aromatic odor)

Cedrus atlantica

Steam distillation of atlantone

wood

Essential oil

Plants

Method of prep

Main component

Celery seed oil ( spicy

odor)

celery

Steam distillation of
seed

Limonene &
selinene used for
flavoring food

Chamomile oil ( Bitter

aromatic taste)

Chamomilla recucita Steam distillation of

the flower and
stocks

Chamazulene and
bisabobol

Cinnamon leaf oil

(spicy odor )

cinnamon

Steam distillation of
leaf

Eugenol

cinnamon bug oil

(spicy taste of
cinnamon)

Cinnamon

Steam distillation of
bug

cinnamaldehyde

ceylon citronella oil

(grassy odor)

cimbopogonnardus

Steam distillation of
leaf and stem

citronelal

Java citronella oil (

sweet flavory rose
like odor)

cimbopogon winter Steam distillation of

leaf & stem
ianus

Citronelal,
citronelol, geraniol

Citrus oil :bergamot

oil (sweet fruity odor)

Citrus aurantium

Pressing pill from

fruit

Linalool,citral &
linalil acetate

Great fruit oil( sweet

orange oil)

Citrus paradisy

Cold pressing pills of

the fruit

Limonene octanal &

decanal

lemon oil ( lemon

pear odor)

Citrus lemonspicy
taste of cinnamon

Pressing pills of the

fruit

Limonene b-pinene
& terpenene, used
in colonge

Essential oil

Plants

Method of prep

Main component

Lime oil

Citrus orantifolia

Cold pressing

Ciniole,citral

Mandarin oil

Mandarin orange

Cold pressing of the

pills

Lemonene &
terpenene

Orange oil bitter

Citrus aurantium

Cold pressing of the

pills

Various aldehydes

Orange oil sweet

Citrus sinensis

Cold pressing of the

pills

Lemonene and
decanal

Clove bud oil

Clove tree

Steam distillation of
bud

Eugenol
,caryophylene,
eugenol acetate

Clove leaf oil

Clove tree

Steam distillation of
leaf

Eugenol acetate

Corriander oil

Coriandrum
satifum

Steam distillation of
fruit

Linalool & fatty

aldehyde

cypress oil( wood

like odor)

Cupressus
sempervirens

Steam distillation of
france

3-carene and apynene

Dill oil

Anetum
graveolens

Steam distillation

Lymonene &
carphonene

Essential oil

Plants

Method of prep

Main component

Fennel oil

Common fennel

Steam distillation of Trans-anethole, used

seed
in flavor and
perfumery

Galbanum oil

Ferula galbaniflua

Steam distillation of Monoterpene &

sesquiterpene,used in
root
perfume

Geranium oil

Pelargonium
graveolens

Steam distillation

Ginger oil

Zingiber oficynale

Steam distillation of Zingiberene &

the root
sesquiphelandrene

Ginger oleoresin

Zingiber oficynale

Extracting with
alcohol or acetone

Guaiacwood oil

Bulnesia sarminty

Steam distillation of Guaiol &

showdas
bulnesol,used in
perfumery

Citronellol,
isomenthone &
formate

Gingerole & shogaol

Jasmine absolute

Jasminum
grandyflorum

Solvent extraction
of the flowers

Benzyl acetate,
indole, cis-jasmone
& methyl
jasmonate

Juniper berry oil

Juniperus comunis

Steam distillation of 1-terpynen-4-ol,afruit

pynenmonoterpene,used
in alcoholic
beverages

Labdanum oil

Sistus ladaniferus

Steam distillation of Monoterpene, used

the gum
widely in perfumery

Laurer leaf oil

Laurus nobilis

Steam distillation of 1,8ciniole,eugenol,li

leaf
nalool, used for
seasoning meat
product & soup

Essential oil

Plants

Method of prep

Main component

Lavender oil

Lavandula anggus
tyfolia

Steam distillation of
flowering top

Cis & transocimene,

ciniole, linalool,
linalil acetate,
lavadulil acetate &
camphor

Litseacubeba oil

litseacubeba

Steam distillation of
fruit

Citral, used for

perfuming
household product

Lovage oil

Levisticum oficinale

Steam distillation of
fruit & leaf

Terpynel acetate &

ligustilide, used for
flavoring to tobacco

Marjoram oil

Origanum majorana

Steam distillation of
hert

1-terpynen-4ol &
cis-sarbinene
hydrate, used in
men perfume

Corn mint oil

Menta alvensis

Steam distillation of
hert

Menthyl acetate,
menthol, menthone

Peppermint oil

Menta pepperita

Steam distillation of Menthol,

hert
menthone, menthyl
acetate &
menthofuran

Spearmint oil

Menta spicarta

Steam distillation of
hert

Menthone,
lymonene,
dehydrocarfone,
sarbinenehydrade,
dehydrocarfil
acetate & carfil
acetate

Mentacitrata oil

mentacitrata

Steam distillation of
her

Linalool & linalil

acetate, used in
perfuming soup

Pennyroyal oil

Menta pulegium

Steam distillation of
flowering top

Pulegone, used for

soup & oral product

Myrrh oil

Commiphora myrrh

Steam distrillation

lindestrene

Essential oil

Plants

Method of prep

Main component

Neroli oil

Citrus aorantium

Steam distillation of
the blossom

Terpenehydrocarbon
, used in fine
fragrances

Nutmeg oil

nutmeg

Steam distillation of
the kernel

Terpinene
hydrocarbon, 1terpene-4-ol, used
for food flavoring

Oak moss absolute

Evernia prunastree

Solvent extraction

Orchinol, methyl3methyl orselinate,

used in perfumery

Olibanum oil

Boswellia cartery

Steam distillation

Used for perfume

Orris root oil

irishfallida

Steam distillation of
the root

Cis alpha irone & cis

gamma irone, very
expensive oil, used in
perfumery & flavor

Patchuoli oil

Phogostemon cablin

Steam distillation of
leaf

Patchualol nor
patchulenol

Pepper oil

Black pepper

Steam distillation of
fruit

Monoterpene hydro
carbon, sarbinene &
pepperine

Peru balsam oil

Meroxylon pereira

Steam distillation

Benzyl benzoate,
benzylcinamate,
nerollidol & vanillin,
used in perfume &
soup

Petite graine oil

Citrus tree

Steam distillation of
leaves

Linalool, linalyl
acetate

Petroselinum
crispum

Steam distillation

Mono terpene
hydrocarbon,
myristicin,apiol,
used in food
seasoning

Parsley oil

Essential oil

Plants

Method of prep

Main component

Pimento oil

Pimenta dioica

Steam distillation of 1,8ciniole, eugenol &

fruit
caryophylene, used
mainly in food industry

Rose oil

Rosa ex damassina

Steam distillation of Citronelo, geraniol, nerol,

blossom
phenethyl alcohol

Rosemary oil

rosemarinusoficinali
s

Steam distillation of 1,8ciniole,

twigs
gammaphinene and
camphor, used in
perfuming shampo
bathfoam & hairtonic

Rosewood oil

Aniba rosae odora

Steam distillation of Linalool acetate, used in

wood
perfume for soap

Clarysage oil

Salvia sclarea

Steam distillation of Linalil acetate. Linalol,

flowering top
terpene alcohol, terpene
acetate

Sandal wood oil

Santalum album

Steam distillation of
wood

Alpha & beta

santalol very
valuable use in
perfumery

Safrass oil

Ocotea pretiosa

Steam distillation of
fruit, branches and
trunk

safrole

Savory oil

Satureja hortensis

Steam distillation of
the hert

Carvacrole, used for

flavoring sausages
and soups

Stranise oil

Illiciumverum hook

Steam distillation of
fruit

Trans anithole, used

for flavoring food &
toothpaste

Tagetes oil

Tagetes minuta

Steam distillation of
flowering plants

Cis ocimene, cis &

trans ocimenone &
tagetone
&dihydrotagetone,
used in flowery
fragances

Essential oil

Plants

Method of prep

Main component

Tarragon oil

Artemisia
drakunculus

Steam distillation for

leaves ,stems &
flowers

Estragole, used in
perfumery

Tea tree oil

Melaleuca
alternifolia

steam distillation of
leaves and twigs

1-terpynen-4-ol, used
in perfumery for
earthy notes

Thyme oil

Thymus fulgaris

Steam distillation of
flowering plants

Thymol & carfacrol,

used in perfumery for
spicy leathery notes

Tolu balsam resinoid

Myroxylon
balsamum

Solvent extraction

Benzyl & cinnamyl

esters of benzoic and
cinnamic acid, used in
perfumery of balsamic
note

Tonkabean absolute

Dipteryx odorata

Solvent extraction of
tonkabean

Coumarin, used in men

fragrances

FLAVORS AND
FRAGRANCES
Chapter 7.3

Vanilla extract

Vanilla planifolia

Solvent extraction
of the pod

Vanillin, used
extensifly in
chocolate,ice cream
and bake product

Verbena oil

Aloysia triphylla

Steam distillation of
leaves

Citral, geraniol &

nerol, used in fine
fragrances

Vetiver oil

Vetiveria zizanioides

Steam distillation of
the root

Sesquiterpene,
alpha & beta
vetinone &
khusimol, vetiverol,
used in fine
fragrances for long
lasting precious
wood notes

Violet leaf absolute

Viola odorata

Solvent extraction of
the leaves

Violet leaves
aldehyde, used in
perfumery in very
low concentration

Essential oil

Plants

Method of prep

Main component

ylang-ylang oils

Cananga odorata

Steam distillation of Methyl benzoate,

blossom
linalool, benzyl
acetate,geranyl
acetate,p-cresol, eugenol
& isoeugenol, used in
fine fragrances

Cananga oils

Cananga odorata

Steam distillation of Same contain as ylang

the flowers
ylang oil plus
caryophyllene

Valerian oil

Velerian ofisinalis Steam distillation of Bornyl acetate, terpene

root
& sesquiterpene
hydrocarbon & iso valeric
acid, used in flavor
&fragrance &
farmacytical

Essential oil

Method of prepn

Main components

Bees wax

Alcohol extraction

Exclusively used in
fine fragrances

Civet cat

Fresh secretion is
taken from the
pouches at intervals

Civet tone and

cyclohexadecanone ,
used in fine
fragrances

The pouches is dried

so the secresation
solidifies to form a
brittle brown, very very expensive, used
in fine fragrances

Muscone and
related macrocyclic
ketone

Materials

Animal secretions:
bees wax
absolute(honey like
odor)

civet

musk

moschusmoschife
rus

Single Fragrance &

flavor compounds

Some Aliphatic & Aromatic compounds

Alcohol
Name of
compounds

preparation

properties

3-octanol

By hydrogenation of 3-octanone

Mushroomy-earthtyodorliquid,
used in lavender composition

2,6dimethyl-2heptanol

By reaction of methylmagnesium
Floweryodorliquid used in
chloride with 2-methyl2-hepten6-one flowery perfume
follow by hydrogenation

Trans-2-hexen-1ol

Fruity greenodorliquid, used in

aroma perfumery

Cis 3- hexen-1ol

Reaction of butyne with ethylene

oxide followed by hydrogenation by
Pd cat

Freshly cut grass odor liquid,

used in green top notes in
perfume

1-octen-3ol

Reaction of hexanal with vynil

magnesium bromide

Mushroomearthy odor liquid,

used in mushroom aroma

Rose odor liquid, used as soap

perfume

9-decen-1ol

Dehydration of1,10-decane diol

10-undecen-1ol

Synthesize from 10-undesyllenic-acid Citrus odor liquid, used in

flower perfume

Nonaden-1ol

Reaction of Grignard reagent with

acrolein

Green violet odor liquid, used

in fresh green perfumery

Aldehyde & Acetal

Name of
compounds

preparation

properties

Hexanal

Fatty aldehydesane generally

produced by dehydrogenation of
suitable alcohol in the presence
of catalyst

Colorless liquid with fatty green

odor

Octanal

Colorless liquid with pungent odor

which becomes citrus like on
dilution

Nonanal

Colorless liquid with fatty rose like

odor and is used in floral
composition

Decanal

Colorless liquid with strong odor,

reminiscent of orange peel but on
dilution becomes fresh citrus odor

Undecanal

Colorless liquid with a fresh

flowerly waxy odor

Dodecanal

Colorless liquid with a fresh

flowerly waxy odor but on
dilution becomes
reminiscent of violets

Tridecanal

Colorless liquid with fatty

waxy citrus odor

2-methyldecanal

By product in the manufacture of 2methylundecanal by hydroformylation

of 1-decene

Colorless liquid with citrus

peel like waxy green odor

2methylundecanal

Hydroformylation of 1- decene to give

undecanal and 2methyldecanal.reaction of undecanal
with formaldehydegues this product

Colorless liquid with incense

and ambergris notes

Ketone
Name of compounds

preparation

properties

3-hydroxy-2-butanone

Partial oxidation of 2,3

butandiol

A pleasant buttery odor

used for flavoring
margarine

2,3-butanedione

Dehydrogenation of 2,3butandiol with copper

chromite as catalyst

Acid & Ester

Name of compounds

preparation

properties

Ethyl formate

Esterification of formic and

with ethanol

Liquid with a pungent fruity

ethered odor

Ethyl Acetate

Esterification of formic acetic Liquid has a green fruity

acid with ethanol
odor

Butyl Acetate

Esterification with butanol

Liquid with a strong fruity

apple odor

Isoamyl Acetate

Esterification with isoamyl

alchohol

Liquid with a strong fruity

banana aroma

Hexyl acetate

Esterification with hexanol

Liquid has a sweet fruity

pear like odor

Isononyl Acetate

From diisobutene by
oxosynthesis followed by
hydrogenation to alcohol
and acetylation

Colorless liquid has a strong

woody fruity odor

Fresh fruity green smelling

liquid

Trans2-2-hexenyl Acetate

Cis-3-hexenyl Acetate

Found in many fruit aromas

Fruity green smelling liquid

Ethyl propionate

Found in many fruit &

alcoholic drinks

Fruity odor reminiscent of

rum

Acyclic Terpene
Hydrocarbon
Name of compounds

preparation

properties

Myrcene

Found in many fruits and

essential oils but little use in
flavor & fragrances

Acyclic terpene ( C10) and

zesquiterpene (C15)
hydrocarbons are unstable
and have aggressive odor due
to their highly unsaturated
structure

Ocimene
B-varnesene

ACYCLIC TERPENE ALCOHOL

Name of compounds preparation

properties

Geraniol

Isolation from essential oil of

java citronella oil

A colourless liquid with a rose like

odor

Nerol

Synthesis from linalool with

orthovandatesas catalyst

A colourless liquid with a rose like

odor but with a freshly green note

Citronelol

Hydrogenation of citronellal
isolated from java citronella oil

A colourless liquid with a sweet

rose like odor

Linalool

Isolation from brazillia

rosewood oil, shiu oil and
corriander oil

A colourless liquid with a flowery

fresh odor reminiscent of the lily
of the valley

Myrcenol

Treating mycene with

dialkylamine followed by
hydrogenation and deamination

A colourless liquid with a

fresh flowery a slight
lime like odor

varnesol

Isolation of many blossom

essential oils

A colourless liquid with a

linden blossom odor
which intensily when
evaporated

Acyclic Terpenes
Aldehyde & Acetal
Name of compounds

preparation

properties

Citronelal

Isolation from essential oil,

java citronella oil

A colorless liquid with a

refreshing odor
reminiscent of balm mint

Hydroxycitronelal

Hydration of citronellol
followed by
dehydrogenation in the
presence of Zn Cu catalyst

Viscous liquid with a

flowery odor reminiscent
of Linden Blossom and Lily
of the valley

2,6,10-trimethyl-9-undcnal

Yellowish liquid with

intense aldehydewaxy
slighthy flowery odor

3,7 dimethyl-7hydroxyoctan-1-al dimethyl

acetal

A colorless liquid with

warm woody citrus odor

Methoxydihydrocitronelal

Liquid with a fresh green

blossom odor

Acyclic Terpenes
Ketones

Name of compounds

preparation

properties

Geranylacetone

A colorless liquid with a

fresh green rose like odor

Tagetone

A major component of
tagettes oil

Acyclic Terpenes Ester

Name of compounds

preparation

properties

Geranyl formate

Esterification

Liquid with a fresh herbal fruity rose odor

Geranyl Acetate

Same as above

Liquid with a fruity, rose note reminiscent

of pear and lavender

Geranyl Propionate

Liquid with a fruity rose odor

Same

Geranyl Isobutyrate

Liquid with a fruity rose odor

Same

Geranyl Isovalerate

Liquid with a strong fruity rose odor

Same

Linalyl, lavandulyl,
citronelyl,ester

Same

Liquid with a fresh herbal rose odor

Cyclic Terpene
Hydrocarbon
Name of compounds

preparation

Limonene

properties
Liquid with lemon odor

Terpinene

Isomerization of limonene

Liquid with a herbaceous

citrus odor

d- Pinene

Distillation of turpentine oil Starting material for synthesis

of borned, camphor and
terpineol

- Pinene

Distillation of turpentine oil Starting material for synthesis

of myrcene

Cyclic Terpene alcohol

Name of compounds

preparation

properties

Menthol

Isolation from Peppermint

oil

Crystal with a peppermint

odor with cooling effect

Terpineol

Acid catalyzed hydration of

pinenes

Liquid with a strong Lilac

odor

Borneol

Isolation from camphor oil,

Lavender, rosemary oils

Crystal with
camphoraceous odor

Cyclic Terpene
Aldehyde & ketone
Name of compounds

preparation

properties

Menthone

Distillation of
dementholized cornmint
oil

Colorless liquid with minty

odor

Carvone

Isolation from caraway oil

and spearmint oil

Colorless liquid with

herbaceous odor
reminiscent of caraway and
oil seeds

Camphor

Distillation & crystallization

of camphor oil

Crystal with cooling effect

Aromatic Alcohol & Ethers

Name of compounds

preparation

properties

Benzyl alcohol

Hydrolysis of Benzyl chloride

by NaOH /Na 2 CO3

Colorless liquid with weak

sweet odor

Phenyl ethyl alcohol

Hydrogenation of styrene
Oxide with Raney Ni

Colorless liquid with mildrose

odor

Cinnamic alcohol

Reduction of Cinnamaldehyde

Colorless crystalline solid with

hyacinth like balsamic odor

Phenylethyl Isoamyl
ether

Colorless liquid with green

sweet flowery odor of
chammomile blossom

Phenylmethyl ether

Colorless liquid with sharp, rosy

green odor

Aldehyde
Name of compounds preparation

properties

Benzaldehyde

Hydrolysis of benzyl chloride

Colorless liquid with a butter

almond odor

Phenylacetaldehyde

Isomerization of styrene Oxide

Colorless liquid with sweet green

odor reminiscent of hyacinth

Cyclamenaldehyde

Alkaline condensation of deriv.

of benzaldehyde with heptanal

Yellow liquid with a intense

flowery odor reminiscent of
cyclamen

Cinnamaldehyde

Alkaline condensation of
benzaldehyde and
acetaldehyde

Yellow liquid with spicy odor

reminiscent of cinnamon

Amylcinnamaldehyd
e

From benzaldehyde and

heptanal

Yellow liquid with a flowery fatty

odor and jasmin when diluted

Hexylcinnamaldehyd
e

Alkaline condensation of
benzaldehyde with octanal

Yellow liquid with a flowery

herbal and jasmin odor

Ketone
Name of compounds

preparation

properties

Acetophenone

By product in the Hock

phenol synthesis

Colorless liquid with a

penetrating sweet odor
reminiscent of orange
blossom

4-Methylacetophenone

From toluene with acetic

anhydride

Colorless crystals with a

flowery sweet odor

Benzylacetone

Hydrogenation of
benzylidene

Sweet flowery smelling

liquid

Benzophenone

Friedel crafts reaction of

benzene, benzoyl chloride
with aluminium chloride

Colorless crystalline solid

with a rosy geranium odor

Ester
Name of compounds

preparation

properties

Methyl Benzoate

Esterification of benzoic
acid with methanol

Colorless liquid with a

strong fruity slighty
pnemolic odor

Benzyl benzoate

Transesterification of
methyl benzoate with
benzyl alcohol

Viscous liquid with weak

balsamic odor

Methyl Cinnamate

Isolation from Alpinia

essential oils

Colorless crystalline solid

with a fruity sweet
balsamic odor

Benzyl Cinnamate

Found in balsam oils

Sweet balsamic smelling

crystals used as fixative

Phenol & derivatives

Name of compounds

preparation

properties

Thymol

Reaction of m.cresol with

propylene with Al2 O3 cat

Colorless crystals with

spicy herbal reminiscent of
thyme

Anethole

Isolation from essential oils

Colorless crystals with an

anise like odor and sweet
taste

Eugenol

Isolation from clove oils

liquid with clove odor

Isoeugenol

Isomerization of eugenol

Viscous liquid with

fineclove odor

Eugenol methyl ether

Methylation of eugenol

Colorless liquid with a mild

spicy odor

Isoeugenol methyl ether

Isomerization &
Methylation of eugenol

Yellow liquid with a

sweetmild clove odor,
carnation

Eugenol acetat

Acetylation of eugenol with

acetic anhydride

Yellowish liquid with fruity

clove odor

Isosafrole

Alkali catalysed of safrole

Viscous liquid with a sweet

anise like odor

P cresyl phenyl acetate

Esterification of p-cresol with Crystal with a narcisjus odor

phenylacetic acid
and honey note

P, openylguethol

Reaction of p-cresol with

phenylacetic acid

Crystal with a sweet vanilla

odor

Phenol Aldehyde
Name of compounds

preparation

properties

Anisaldehyde

Oxidation of p cresyl
methyl ether peroxy
sulfates, with Ag+ as
catalyst

Yellowish liquid with a

sweet, mimosa hawthorn
odor

Vanillin

From waste sulfite liquors

(previously from Iso
eugenol)

Colorless crystalline solid

with odor of vanilla

Veratraldehyde

Methylation of vanillin

Crystals with woody vanilla

odor

Ethylvanillin

Similar like vanillin but

using guethol

Crystall with vanillin odor

3x stronger

Piperonal

Oxidation of Isosafrole

White crystals with a sweet

flowery slighty spicy odor

Phenol ketone
Name of compounds

preparation

properties

Acetanisole

Acetylation of anisole

White crystals with sweet

odor reminiscent of
hawthorn

Raspberry ketone

Alkaline condensation of 4- Colorless crystals with a

hydroxy benzaldehyde with sweet fruity odor
acetone
reminiscent of raspberry

Phenol Carboxylates
Name of compounds

preparation

properties

Methyl salicilate

esterification

Main component of
wintergreen oil as liquid with a
sweet phenolic odor

Iso amyl salicylate

Same

Colorless liquid with a sweet,

clover like odor

Phenylethyl salicylate

Same

Crystalline solid with a weak

but long lasting babamic,
blossom odor, reminiscent of
rose & hyacinth

Cyclic ether
Name of compounds

preparation

properties

Cineole

Isolation from eucalyptus

oil

Colorless liquid reminiscent

of camphor

Rose Oxide

From citronellol

Colorless liquid with a

strong odor reminscent of
geranium oil

Ethyl maltol

Ethylfurfuryl alcohol is
reacted with halogen
followed by hydrolysis

White crystalls with a very

sweet caramel like odor 6x
stronger than maltol

Lactone
Name of compounds

preparation

properties

- undecalactone

Intramolecular cyclization
Colorless liquid with a
of 10-undecalynic acid with peach like odor
H2SO4

- decalactone

Peracid oxidation of 2pentyl cyclopentanone

Colorless,viscous liquid
with a creamy coconut
peach like odor

FLAVORS AND
FRAGRANCES
Chapter 7.4
benjaminlukas@yahoo.com

QUALITY CONTROL
Quality control of flavor & fragrance
compounds are is obtained by
comparing the analytical and
sensory data with standard &
specification
The analytical data usually consist
of the physical constant such as
density, refractive index, optical
rotation, melting point & boiling
point as well as the purity
The purity and the chemical of in
purity can be obtained using GC ,
HPLC, GCMS ,NMR techniques
Sensory data can be obtained by
trained person as well as
electronic nose

Effects of Packaging Materials on

Flavor Quality of Foods eg Oats and
Orange Juice

Packaging is a critical component of food products.

Widespread and continuously increasing usage of plastics is due to the

development of various barrier products.

Migration of compounds from packages into foods and absorption of flavor

compounds of foods by packaging materials can alter the flavor profiles of
foods.

Packaging Components

Polymers
Monomers
Plasticizers
Catalysts
Antioxidants
Blocking agent
Antislipping agent

Coatings
Ink
Solvents
Adhesives

Gas Chromatogram of compounds in

Polystyrene cups

Compounds in Polystyrene Cup

Peak

Compound

Content

Odor

N-Butene

Ethyl benzene

1069

Sweet solvent

Isopropyl Benzene

106

Pungent

Propyl benzene

14

Plastic, unpleasant

Solvent

Compounds in Polystyrene Cup

Peak

Compound

Content

Odor

Ethyl toluene

21

Toluene, plastic

Styrene

404

Strong chemical

Methyl styrene

14

Chemical, plastic

Oats and Grits in Polystyrene Cups

GCMS data cannot be uploaded but

it shows the presence of
ethylbenzene and styrene
which are the precussors
of polystyrene.

Residual Compounds Migration from

Polystyrene Cup to Oats and Grits

Compounds

Oats

Grits

Ethylbenzene

13%

1.4%

Styrene

18%

2.0%

Residual Compounds in Oats and

Grits
Compounds

Oats

Grits

Ethylbenzene

25.0 ppm

2.7 ppm

Styrene

13.0 ppm

1.4 ppm

Absorption of Orange Juice

Flavor Compounds by Packaging
Materials

Packaging Materials

Low Density Polyethylene (LDPE)

Polyethylene Terephthalate (PET)

Polyvinylidene Chloride (PVdC)

Ethyl-Vinyl Alcohol Copolymers (EVOH)

Gas Chromatogram of Orange Juice

Flavor Compounds

GCMS data cannot be uploaded but it shows

the presence of many compounds including dlimonene, alpha pinene, octanal and ethyl
butyrate.

Orange Juice Flavor Compounds

D-Limonene
Alpha Pinene
Octanal
Ethyl butyrate

Effects of Packaging Materials on Limonene

Absorption During Storage

D-Limonene is absorbed strongly

by first LDPE followed by PET
then EVOH and lastly PVdC

Effects of Packaging Materials on

ethyl butyrate Absorption During
Storage

Ethyl butyrate is
absorbed strongly
by first LDPE followed
by PET
then EVOH and lastly
PVdC

Effects of Packaging Materials on

Octanal Absorption During Storage

Octanol is absorbed strongly

by first LDPE followed by PET
then EVOH and lastly PVdC

CH3-CH2-(CH2)5-CH2-OH

Conclusion on packaging

Migration of polystyrene cups compounds to oats and grits

Absorption of orange juice flavor compounds by packaging
materials

Conclusion
Organic chemists may need to know how to prepare Essential Oils as well
as the Single Flavor & Fragrance Molecules preferably using natural
products as the raw materials eg eugenol, isoeugenol, caryophyllene,
methyl eugenol, methyl isoeugenol, eugenyl acetate, isoeugenyl acetate,
caryophyllene oxide, caryophyllene alcohol and otherderivatives made
from clove oil, while citronellol, geraniol, cironellal, citronellyl acetate,
geraniol aceyate and others from Java citronella oil etc

The End