Molecul!

of
Baking
A Magazine for the Culinary Chemist

Traditional vs.
vs. Avant-garde: A
Cupcake Recipe Comparison Cut the fat
and save the taste:
Healthy Baking 101

Molecules of a
cupcake!
It’
It’s all inside this special edition!

Cupcakes:
Naughty or Nice?
The Cupcake Craze
By Willa Zhou

Across the country, people are

flocking to cupcake boutiques to sample
these miniature cakes in all sorts of
creative shapes and flavors. Recently,
cupcakes have been featured in the New
York Times and Martha Stewart Living as
well as in popular TV shows such as Sex
and the City. Moreover, an entire
generation of cupcake bloggers, cupcake
critics, and plain old cupcake lovers has
emerged. The cupcake craze has hit the
United States at full throttle, but there is
one thing standing in the way of total
cupcake domination: the health factor.
“Cupcakeblog.com is about - you guessed
it - cupcakes. More specifically each post
features a unique cupcake recipe created
by Cheryl Porro and accompanied by her
own photography.” - cupcakeblog.com
Health concerns have given rise to
an intense scrutiny of food that puts the
paparazzi coverage of even the most
notorious pop stars to shame. Modern
technology has enabled chemists to pick
apart and analyze edible commodities
down to the atom for their nutritional
value. This information has heavily
influenced the perception of food in the
US. In fear of fat, more and more
Americans are becoming wary of high-
cholesterol ingredients and oily goods. So
cupcakes might look and taste amazing,
but they are still subject to the health
concerns of the public.
“The Latest Entrepreneurial Fantasy Is
Actress Sarah Jessica Parker chows down on a
cupcake as her character, Carrie Bradshaw, in the
popular TV series Sex and the City.
Being a sweet dessert, cupcakes
must be horrible for one’s health, right?
Not necessarily. While the traditional
cupcake recipe does contain a slew of
molecules that are hazardous for your
health, an avant-garde approach to the
cupcake recipe is able to maintain a
delicious taste while knocking out some
of those unhealthy contents. This special
edition of Molecules of Baking: A
Magazine for the Culinary Chemist will
tell you all you need to know about the
molecules of a traditional cupcake, and
he impact of these molecules on health
and baking. A few simple and affordable
baking tips on how to produce a healthier
cupcake will be reported throughout this
issue as we compare and contrast two
vanilla cupcake recipes. If you love
cookies and chocolate cake, these tips
can be generalized to baking all sorts of
different pastries! Let’s begin by looking
at the recipes (next page).
Right: T-shirts for
cupcake lovers
Selling Cupcakes” - 11/25/2009

1
 A
Recipe
Comparison
The Traditional
Traditional Vanilla Cupcake
From Country Living
Ingredients:
1 1/2 cup(s) all-purpose flour
1 1/2 teaspoon(s) baking powder
1/4 teaspoon(s) salt
1/2 cup(s) (1 stick) unsalted butter, softened
1 cup(s) sugar
2 large eggs, room temperature
1/2 teaspoon(s) vanilla extract
1/2 cup(s) whole milk
Directions:
Heat the oven to 400 degrees F. Lightly
coat an 8-inch cake pan with butter and
dust with all-purpose flour. Sift the cake
flour, baking powder, and salt into a
large mixing bowl.
# Beat in the butter one heaping 1/4
teaspoonful at a time, using an electric
mixer set on low speed, until the mixture
resembles coarse sand. Beat in the sugar a
tablespoon at a time, until the mixture
resembles fine damp sand. Beat in the
eggs one at a time. Add the vanilla and
milk, and beat on medium-high, just until
blended. Do not overbeat.
# Pour into the prepared pan and bake
until a wooden skewer inserted in the
center comes out clean — 30 to 35
minutes. Cool cake in the pan on a wire
rack for 5 minutes.
Vs. The Avant!garde
Avant!garde Vanilla Cupcake
Adapted from Carrier
Ingredients:
"#$ cup plus all!purpose %our
" teaspoon baking powder
"#& teaspoon salt
"#' cup canola or vegetable oil
'#& cup sugar
"#$ cup vanilla soy yogurt
" tablespoon vanilla
$#' cup soymilk
"#$ cup plus " tablespoon whole!wheat %our
$ tablespoons cornstarch
"#$ teaspoon baking soda
Directions:
•Preheat oven to '() degrees F* Line a
mu+n pan with "$ cupcake liners*
•In a large mixing bowl, whisk
together the yogurt, soy milk, oil,
sugar, and rosewater* Si- in %our,
cornstarch, baking soda, baking
powder, and salt* Mix until large
clumps disappear* Fill liners three!
quarters of the way*
•Bake $) to $$ minutes* Transfer to a
cooling rack and let cool completely
before frosting*
2
 Flour: The Substance Spiral structure formed by the
HMW subunits of glutenin
Flour can be derived from a
variety of plants (oats, barley, corn,
etc). In the US, wheat flour is the
most commonly used for baking
because it contains high levels of
gluten, a composite of the proteins
glutenin and gliadin (shown at right
and left, respectively). When baked,
these proteins form a network of
strands that define the texture of
baked goods.

The wheat kernel has three parts:
the endosperm, the bran and the germ
(Vaclavik 81). Chart 1 below illustrates
the unique combination of nutrients
found in each part of the kernel (82).
White wheat flour uses only the
endosperm, while 100% whole-wheat
flour uses all three parts of the wheat
kernel (that’s why it’s called a “whole”
wheat flour). As seen from Chart 1, the
bran and germ carry significant amounts
of nutrients such as B-vitamins, iron,
dietary fiber and protein. A majority of
these essential nutrients are lost in refined
(white) flour, which is why whole-wheat
flour is preferable from a health
standpoint. Chart 1: Origin of Wheat Kernel Nutrients
Ironically, some flour companies try
Wheat
Kernel
to compensate for the nutrients lost in
the milling process of white flour by
adding a few vitamins and minerals,
which are then marketed on the product
label. But even this enriched white flour
is no match for plethora of nutrients in
whole-wheat flour.
While keeping the germ in whole-
wheat flour does slightly increase its fat
content, this is a nominal fee for for the
nutrients gained from the germ. Further,
white flour and whole-wheat flour
contain the same number of calories per
serving!
Wheat Kernel

Endosperm Bran Germ

primarily starch protein and b-vitamins most of the kernel's thiamin

high in protein some fat hightest content of fat (of the 3 parts)
low in fat and soluble fiber trace minerals b-vitamins and trace minerals
some b-vitamins and iron insoluble fiber some protein

In addition to its energy and nutrients, whole wheat flour also has the bonus of a lower Glycemic Index
(GI) than white flour. The GI is the rate at which a food raises your blood sugar (BS) level in comparison to
the rate at which glucose raises your BS level. Because a correlation between a high-GI diet and health
problems such as diabetes and heart disease has been discovered, it is recommended that one try to limit
one’s consumption of high-GI goods (Liu L15S50). In general, simple sugars and refined carbohydrates
require less metabolism and therefore enter the bloodstream faster, causing a spike in blood sugar (Vaclavik
65). Accordingly, whole-wheat flour has a lower GI than white flour because it is less refined. 3
 More on Flour
A few other notable differences between whole-wheat flour and white flour can be
observed in their nutrition labels. Note that for a 1/4 cup serving, whole-wheat flour
has 33% more protein, three times the potassium, and four times the dietary fiber!
Also, please see Table 1 for details regarding the vitamins and minerals found in
whole-wheat flour as opposed to white flour. Here are a couple of the many ways
these nutrients can help you:

Get rid of that constipation! Dietary

fiber helps your digestive system to
operate smoothly, AND it has been
linked with a lower risk of heart
disease, diverticular disease (inflamed
intestines), and type 2 diabetes. Even
though humans are unable to break
down the cellulose in dietary fiber, we
still have much to gain from this
carbohydrate (Fiber, Liu L15S46).
Recommended intake: 20 grams/day. Above: The nutrition labels for King Arthur’s all-purpose
flour (left), and 100% whole-wheat flour (right).
Reduce your risk of high
blood pressure and muscle Table 1: Vitamin, Mineral, and Fiber Content of Wheat Flours (per 100g)
cramps. It is recommended that
Thiamin B1 Riboflavin B2 Niacin B3
people consume 4.7 grams Flour (mg) (mg) (mg) Iron (mg) Fiber (g)
(potentially more for athletes) R1: Whole Wheat
of potassium per day because Flour (whole grain) 0.66 0.14 5.2 4.3 2.8
R2: White Flour
this mineral works with sodium (refined) 0.07 0.06 1 0.9 0.3
to prevent muscle cramps and Difference (R1-R2) 0.59 0.08 4.2 3.4 2.5
hypertension (Anderson).

Cupcake Connection:
Now that we have learned about the benefits of whole wheat flour, let’s look at how this ingredient can
impact a cupcake recipe. Recall that the traditional recipe calls for 1 ! cups of all-purpose white flour,
while the avant-garde recipe calls for one third that amount, only ! cup. The latter then calls for ! cup
plus two tablespoons of whole-wheat flour. This will deliver larger quantities of dietary fibers, vitamins,
minerals, proteins, and nutrients to every delicious bite of your cupcake!

Healthy Baking Tip #1:

Replace half of the white flour with whole wheat flour. You can
replace all of the white flour if you don’t mind a grainier texture.
Just be sure to add a tablespoon of milk/liquid for every cup
substituted as whole-wheat flour absorbs more moisture than
regular flour.

4
 To Egg or Not to Egg?
Chicken eggs are used to enhance the
structure and texture of cupcakes. The
globular proteins found in egg whites can
leaven a batter by being whisked to three
times their original volume, and the
lecithin in egg yolks are wonderful
emulsifiers (Vaclavik 369).
Cupcake Connection
Healthy Baking Tip #2
The avant-garde recipe uses 2/3 cup of
vanilla soy yogurt along with a combination
of baking soda and baking powder in place
of the two eggs in the traditional recipe.
While eggs are a rich source of nutrients,
this substitution can be useful for those
who must limit their intake of cholesterol,
and for those who choose not to consume
eggs. In terms of nutrition, using soy yogurt
instead of eggs will yield 20-40 less calories,
minimizes the sodium level, halves the fat
content, and eliminates saturated fat and
cholesterol. However, this is a trade-off for
all the nutrients found in eggs. Keeping the
whites and replacing the yolks with 2 tbsp of
soy yogurt each would be one way to keep
some nutrients and lost the cholesterol.
Above: Cholesterol Molecule;
Right: Albumin globular
proteins found in eggs.
The C-word:
CHOLESTEROL
Between 2002 and 2006, US egg sales
declined by 8.6% (Weise). This could be due
to a variety of reasons, but I would guess that
the fear of cholesterol played a role in this
decline. To be clear, cholesterol is a steroid
molecule that your body uses for cell
membranes, producing Vitamin D, and
synthesizing important hormones such as
testosterone, progesterone, and estradiol
(Clardy L6S48, Schafer 1). Even though there
is only one cholesterol molecule, it is generally
referred to in two dimensions as a high-
density lipid (HDL), and as a low-density lipid
(LDL). The former tends to be deposited in
your liver while the latter tends to be
deposited in your arteries and has been
associated with coronary heart disease (Schafer
2). For this reason, it has been recommended
that people limit their intake of cholesterol to
no more than 300mg per day. One egg yolk
has about 212mg of cholesterol, which has led
many people to cut eggs out of their diet.
Unfortunately, many people say goodbye
to eggs without realizing that they are one of
the most nutrient-rich foods available. Eggs
are a complete protein, and are packed with
an impressive combination of vitamins,
minerals, and fats that are essential for your
body (Vaclavik 229, Nutrient). Furthermore,
many eggs yolks are now enhanced with
omega-3 fatty acids by feeding chickens a flax
seed diet (Nutrient). These fatty acids play a
major role in brain function, but cannot be
manufactured by the body. Thus, if your
health permits the ingestion of cholesterol, it
may be beneficial to use eggs in moderation.
5
 Fats
Another difference between these two recipes
comes in the fat. The traditional recipe calls for
! cup of unsalted butter, while the avant-garde
recipe calls for 1/3 cup of oil. While all fats
provide about 9kcal of energy per gram, there are
major discrepancies between these two fats in
their levels of cholesterol, the types of fat
molecules they contain, and the presence of
vitamin A.
Butter actually has about 20 less fat calories per
tablespoon than canola oil does, but this is a
deceiving number because not all fats are created
equal. Fats are molecules made up of a glycerol
molecule attached to two or three long
hydrocarbon chains (Liu L15S30). These chains
of carbon and hydrogen can take up different
shapes, and it is these shapes that differentiate
fats into the following four categories:
Saturated Fats. So called because all of its
carbons are saturated with hydrogen molecules.
These fats are able to stack together tightly and
have a high melting temperature because there
are no C=C double bonds. Saturated fats increase
cholesterol levels (HDL and LDL), and have
been correlated with increased risk for heart
disease (Liu L15S32). For these reasons, people
are advised to avoid saturated fats.
Monounsaturated Fats. Fats that have one
carbon double bond. Monounsaturated fats have
been known to “selectively elevate” HDL, which
has led it to be recommended over
polyunsaturated fats for certain individuals
(Edwards 43, 45). These fats have a lower
melting point than saturated fats because the
C=C bond creates a kink that prevents them from
stacking together as tightly as they could.
Polyunsaturated Fats. Fats that have
multiple carbon double bonds, and thus more
knks in their structure. These fats have the
lowest melting point and tend to be liquid at
room temperature. They appear to lower
overall cholesterol levels, and are
recommended as part of a healthy diet.
Trans Fatty Acids. Fats that contain a trans
C=C double bond, which creates a kink that
allows these fats to pack together even
tighter than saturated fats. Evidence linking
these fats to increased risks of heart disease
is so strong that a few states have banned
trans-fat in one form or another (Edwards
43).
Cupcake Connection
Healthy Baking Tip #3
Looking closer, you’ll find that butter carries
7g of saturated fat per tbsp. compared to 1g
per tbsp. for canola oil. Moreover, canola oil
has 9g of monounsaturated fat and 4g of
polyunsaturated fat compared to butter’s 3g
and 0.4 g, respectively. Thus, using canola
oil gives 1/7 the amount of saturated fat of
butter, and way more “good fats,” which
provide energy, have no cholesterol, and
have molecules that are easier to disband.
Butter does have some vitamin A, but it also
has 31mg of cholesterol of which canola oil
has none. Though butter holds a special place
in the American diet, substituting canola or
vegetable oil when possible will produce
healthier cupcakes.
Nutritional labels of canola oil (left) and
unsalted butter (right).
6
 Milk: the Liquid

While most animals are unable to digest the milk of other species, many people have developed
the special ability to digest cow’s milk. This liquid has become a key ingredient in cake recipes
because it provides molecules - such as water, protein, the lactose sugar and fat – that work to
enhance the texture and taste of a cake (Vaclavik 369). Unfortunately, milk has been victim to
harsh criticisms of late because of its unfriendly levels of cholesterol and saturated fat. Luckily,
soymilk is a perfect substitute that carries out the baking duties of milk without the unwanted
molecules!
Healthy Baking Tip #4:
Table Two: Effects of Milk and Soymilk on Recipes
Use soymilk in place of
Traditional Avant-garde whole milk to maintain
Whole Milk Soy Milk a moist texture while
Recipe Amount 1/2 cup 2/3 cup
Calories per recipe reducing both
amount 75 67 cholesterol content
Fat 4g 2.3 g and fat calories!
Saturated Fat 2.5g .3g
Cholesterol 17mg 0
Vitamin C 5% dv 0
Cupcake Connection
Going back to the recipes, the
Hydrophobic and Hydrophilic Molecules in traditional calls for ! cup of whole milk
Cupcakes: The Emulsion while the avant-garde requires 2/3 cup of
Milk plays a substantial role in the emulsion of soy milk. Table 2 shows that even a
cake batter. “An emulsion is formed when oil, larger portion of soymilk yields less
water, and an emulsifier are mixed together” calories, eliminates the cholesterol, and
(Vaclavik 314). Oil and water do not combine on greatly reduces the amount of fat and
their own because their molecules follow the “like saturated fat than those found in whole
attracts like” rule. The long, hydrophobic, milk. While the latter does offer a small
hydrocarbon chains of fats like to stick to amount of vitamin C, which soymilk
themselves and similarly hydrophobic molecules; does not, there are comparable levels of
likewise, water prefers to be near hydrophilic carbohydrates, protein, sodium, calcium
molecules (Clardy). Like many baked products, and other vitamins in these two liquids.
cake batters combine oil and water with the Thus, soymilk appears to be a very
assistance of an emulsifier. The casein proteins in economical substitute for milk in terms
homogenized milk are great emulsifying agents of nutritive value.
because they help to separate milk fats into small
droplets, and to spread those droplets out amidst
the water molecules of milk. As milk is mixed into
the batter, these hydrophobic droplets attract fat
from other ingredients to disperse themselves
among the batter, creating a smooth and even cake
texture! It may be a concern that replacing milk
will prevent a proper emulsion from taking place.
This is not an issue because the lecithin molecule
found in soy milk is a fine emulsifier as well! Casein protein found in milk that disperses among the
interfaces of fat cells to emulsify ingredients
7
While this special issue of Molecules of Baking
focused on the differences between the traditional
and the avant-garde cupcake, there are also …And the rest
some interesting things to note about the
ingredients they have in common.
Flavor Facts:
• The vanillin molecule responsible for the trademark
vanilla flavor of cupcakes and cake ironically comprises
very miniscule portion of the batter.
• Natural vanilla extract is a combination of hundreds of
different compounds whereas imitation vanilla extract
contains only the vanillin molecule. Oddly, this molecule
has been synthesized from a bi-product of wood pulp
processing (Harrison).
• There are about 10 calories per tablespoon of vanilla.

Sodium bicarbonate, more commonly known as baking

soda is a molecule that releases CO2 when heated
according the chemical equation provided below. This
creates air bubbles that rise the batter (Czernohorsky 1).
Sodium bicarbonate is often used with an acid to
maximize the CO2 produced. Baking powder is just
sodium bicarbonate combined with an acidic compound
such as cream of tartar (4).
Above: A sodium bicarbonate molecule. Below:
The chemical reaction that sodium bicarbonate
undergoes when heated to produce CO2.
Further below: The chemical reaction that
occurs when sodium bicarbonate has an acid to
react with. Note that this is a more economical
production of CO2.

The avant-garde recipe also uses 2 tablespoons of cornstarch,

which is a carbohydrate made of the amylose and amylopecin
molecules (both use glucose as a building block) (Vaclavik 50). It
provides about 4kcal of energy per gram (or 30kcal/tbsp), and
beyond that has nominal nutritional value (65). In cupcakes, it’s
used as a thickening agent, which helps to compensate for the
liquid nature of oil used in the recipe.

Sodium chloride, or table salt, is used for flavoring and texture in

cupcakes. 1/4 teaspoon of iodized salt provides your body with
45% of the recommended daily intake of iodine! This element is
essential for the production of the thyroid hormone, which is
responsible for many important biological functions (Clardy L9).

8
Dear Reader,
!di"#$% No&
I hope that this special Cupcake Edition of Molecules of Baking has provided you with
some useful information. I love cupcakes, and have often wondered about the science behind their
ingredients and nutritious value. After researching the traditional cupcake recipe, I found that it
would be easy to reduce the calorie count and fat content with a few simple substitutions. Being
aware of current concerns about food, I thought it would be nice to share some healthy baking
tips based on the molecules within a cupcake. To close out this issue, the table below illustrates
the differences in the overall fat and calorie content of the two recipes discussed. You will find
that the avant-garde recipe has 23% less calories, and 24% less fat than the traditional recipe!
These add to the avant-garde benefits already discussed in terms of vitamins, minerals, dietary
fiber, types of fat, the Gylcemic Index, and cholesterol. Best of all, the former still delivers a
delicious dessert. If you don’t believe me, just try out the recipes from p.2 the next time you bake.
This concludes our molecular investigation of the cupcake. Now, on to the sugar and frosting...

'incerely,
(i)a Zho*
'LS 11 Fa) 2009

Table 3: Recipe Comparison: Calories and Fat Content

Traditional Calories Calories from Fat Calories Avant-garde
1 1/2 cup(s) all-purpose flour 660 0 10 245 1/2 cup plus 1 tbsp all-purpose flour
1 1/2 teaspoon(s) baking powder 0 0 0 0 1 teaspoon baking powder
1/4 teaspoon(s) salt 0 0 0 0 1/4 teaspoon salt
1/2 cup(s) unsalted butter 800 800 640 640 1/3 cup canola or vegetable oil
1 cup(s) sugar 720 0 0 540 3/4 cup sugar
2 large eggs, room temperature 130 70 17 100 1/2 cup vanilla soy yogurt
1 teaspoon(s) vanilla extract 10 0 0 30 1 tablespoon vanilla
1/2 cup(s) whole milk 75 35 20 67 2/3 cup soymilk
225 1/2 cup plus 1 tbsp whole-wheat flour

Total for recipe 2395 905 687 1847 23% less calories
Total per serving 200 75 57 154 24% less fat
 +cknowledgment,
“Basic Vanilla Cake.”
Cake.” Country Living. (9 Dec 2009).
http://www.countryliving
http://www.countryliving.com/recipefinder/basic-vanilla-cake-69
.com/recipefinder/basic-vanilla-cake-69
“Fiber: Start Roughing It!” It!” Harvard School of Public Health. (9 Dec 2009).
http://www.hsph
http://www. hsph. . harvard.
harvard.edu/nutritionsource/what-should-you-
eat/fiber-full-story/index.html
eat/fiber-full-story/index.html
“Nutrient Value of Eggs.”
Eggs.” Egg Nutrition Center.
Center. (10 Dec 2009).
Anderson, J., L. Young and E. Long.Long. “Potassium and Health.
Health.” Colorado
State Universtiy Extension. Revised 8/08.
http://www.ext.colostate
http://www.ext.colostate.edu/PUBS/foodnut/09355.html
.edu/PUBS/foodnut/09355.html
Carrier, Alicia Lynn. “Rosewater cupcakes.”
cupcakes.” Bread and Honey Food Blog.
Blog.
(9 Dec 2009). http://bread-and-
honey.blogspot
honey.blogspot.com/2008/06/rosewater-cupcakes.html
.com/2008/06/rosewater-cupcakes.html
Clardy,
Clardy, Jon. SLS Lectures. Fall 2009.
Edwards, W.P. The Science of Bakery Products.
Products. Cambridge: The Royal
Society of Chemistry, 2007.
Ghirmai,
Ghirmai, Eva. Computer Advice. Dec 2009.
Harrison, Karl. “Vanilla.”
Vanilla.” 3Dchem. (March 2007) (10 Dec
2009).http://www.3dchem.
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com/moremolecules.asp?ID=307&
.asp?ID=307&otherna
otherna
me=Vanilla
http://www.enc-online.org/health_issues/eggnutr
http://www.enc-online.org/health_issues/eggnutr..htm
Liu, David. SLS Lectures. Fall 2009.
Nutrition Facts. The Daily Plate. (9 (9 Dec 2009.)
http://www.thedailyplate
http://www.thedailyplate.com/nutrition-calories/food/generic/whole-
.com/nutrition-calories/food/generic/whole-
milk
Schafer, Elisabeth and Diane Nelson. “Cholesterol In Your Body.” Body.” Iowa
State University. (10 Dec 2009).
www.extension.iastate
www.extension.iastate.edu/publications/ncr332.
.edu/publications/ncr332.pdfpdf
Vaclavik,
Vaclavik, Vcikie A. and Elizabeth W. Christian. Essentials of Food Science.
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3rd Ed. New York: Springer, 2008.
Weise,
Weise, Elizabeth. “Cage-free hens pushed to rule roost.”
roost.” USA Today
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.com/news/health/2006-
04-10-eggs-cage_x.htm
04-10-eggs-cage_x.htm
 (i)a Zho*
'LS 11 Fa) 2009