Chemistry of Fats, Oils,

and Waxes
Centeno, Kathryn

Decem brano, Katrin Mae

Ram iscal, Michael Gabriel

Villalba, Shaira Phel

Lipids
Lipids are a class of biological molecules
defined by low solubility in water and high
solubility in nonpolar solvents.

Role of Lipids
1. They store energy and protect and insulate internal
organs. In human bodies they are stored as fat
cells and in animal bodies as starch.
2. They are found in nerve fibers and hormones as
steroids, which act as chemical messengers.
3. Because they are not soluble in water, a major
function of lipids is to build the cell membranes that
separate the internal contents of cells from the
surrounding aqueous environment.

Classification of Lipids
1. Triglycerides
- derived from glycerol and three fatty acids
2. Phospholipids
- contains glycerol and two fatty acids
3. Steroid
- composed of four fused rings of carbon where
functional groups are attached
4. Waxes
-organic compounds that characteristically
consist of long alkyl chains.

Fatty Acids
A fatty acid contains a long chain
attached to carboxylic acid
group at one end.
Normally, fatty acid contains an
even number of carbon atoms,
usually between 12 and 20.
They are insoluble in water
because the size of the
nonpolar portion is bigger than
the size of polar portion
(carboxyl group). They form
micelle in water.

Types of Fatty Acids

1. Saturated Fatty Acids
no C=C bonds
2. Unsaturated Fatty Acids
a. Monounsaturated
one C=C bond
b. Polyunsaturated
two or more C=C bond
c. Cis/Trans

Saturated Fatty Acids

Generally found in animal, palm, cocoa and coconut
and the foods made from them.
Single carbon-carbon bonds.
General formula CnH2n+1 COOH
Certain fatty acids are already 'naturally saturated' in
that they cannot be made 'harder' than they are in
nature.
Saturated fatty acids are extremely stable i.e. they do
not easily become rancid, meaning they have good
keeping properties (shelf life).

Unsaturated Fatty Acids

Generally found in plant and fish and the foods made
from them.
Carboxylic acids
Stability depends on the number of C=C bonds.
Carbon double bonds are highly reactive making it
unstable. As the amount of unsaturation increases the
stability decreases.

Unsaturated Fatty Acids

Classifications:
1. Mono-unsaturated fat contains fatty acids with 1 C=C double bond. Ex: olive, canola
and peanut oils.
2. Poly-unsaturated fat contains fatty acids with 2 or more C=C double bonds. E.g.
safflower, sunflower, corn, fish oils).
3. Cis and Trans Fat

a. Cis Unsaturated Fat - H atoms on the same side of the double bond. have lower
melting points than trans fats since this configuration causes more kinking of the chain.
The molecules are not as closely packed, decreasing the strength of the van der Waals
forces between them.
b. Trans Fat - H atoms on opposite sides of the C=C double bond. Occurs in processed
unsaturated fats commonly through hydrogenation process

Fats and Oils

Fats and oils are made through esterification, a reaction
in which the hydroxyl groups of glycerol form ester
bonds with the carboxyl groups of fatty acids. It is the
reaction between glycerol and three fatty acids to
produce triglycerides (fat) and water.

Reactions Triglycerides Undergo

1. Hydrolysis important for fat and oil digestion. Triglycerides
are hydrolysed (split by water) in the presence of strong acids or
digestive enzymes called lipases. The products of hydrolysis of the
ester bonds are glycerol and three fatty acids.

Reactions Triglycerides Undergo

Hydrogenation - converts carbon-carbon double bonds to single bonds. The
hydrogen gas bubbled through the heated oil the presence of a nickel
catalyst (or another transition metal).

3. Oxidative Rancidity - Results in the formation of a small carboxylic acid and

an aldehyde. - Responsible for the foul odor associated with fat
decomposition
Triglyceride + O2 Small organic molecules

Fats

Generally crystalline solids at room temperature.

Contains more saturated fatty acids
As the length of the fatty acid chain increases the
number of atoms and number of electrons increases.
The strength of the Van der Waals forces between
the fat molecules increases, increasing the melting
point.
Ex: butter, cheese

Oils
Generally liquids at room temperature.
Contains more unsaturated fatty acids. The double
bond in unsaturated fatty acids produces a kink in
the chain which means that the fat molecules can not
pack closely together. As the number of C=C
double bonds increases the amount of kinking
increases and the distance between the fat
molecules increases. This decreases the strength of
the Van der Waals forces between the molecules,
decreasing the melting point.

Waxes
The word "wax" is derived from the old
English "weax" for the honeycomb of the
bee-hive. Thus, bee wax can be
considered as the reference wax.
Wax is the water resistant protective
coatings of leaves, fruits, and trees,
also in animals, algae, fungi and bacteria.
Wax is hydrophobic in nature produced by
combining fatty acids with alcohols.
All waxes are water-resistant materials made up of various substances includinghydrocarbons
(normal or branched alkanes and alkenes), ketones, diketones, primary and secondary alcohols,
aldehydes, sterol esters, alkanoic acids,terpenes (squalene) and monoesters (wax esters), all with
long or very long carbon chains (from 12 up to about 38 carbon atoms) and solid in a large range
of temperature (fusion point between 60 and 100C).
They are soluble in aromatic solvents, chloroform, ethers, esters and ketones.

Good Fats vs. Bad Fats

Good Fats: Monounsaturated
Polyunsaturated Omega 3, 6
Bad Fats: Trans Fat

2016-8-13

Essential Fats
1.

Omega 3 Fats
Once eaten, the body converts (alphalinolenic
acid) ALA to (eicosapentaenoic acid ) EPA and
(docosahexaenoic acid) DHA, the two types of
omega-3 fatty acids more readily used by the
body.

2016-8-13

Sources

ALA:ALA is found in flax seed (18-22%) and flax

seed oil (50-60%), and in small amounts in some
nuts, green leafy vegetables, canola, wheat germ
and black current seeds.
EPA and DHA:EPA and DHA are found in fatty fish
like salmon, mackerel and tuna. Depending on the
source, fish oils vary in the amount of EPA and DHA
they provide. Fish oil supplements often contain
18% EPA and 12% DHA, with more concentrated
oils containing 30% EPA and 20% DHA. Algal
sources of EPA and DHA are also widely available

Essential Fats
2. Omega 6 Fats
Linoleic acid is converted in the body to the longchain polyunsaturated fatty acids gamma-linolenic
acid (GLA) and arachidonic acid (AA)

Sources

LA:LA is present in many vegetables and most vegetable

oils sunflower (65-75%), safflower (79%), evening
primrose seed (72%), corn (57%), peanut (31%), canola
(19-26%), and olive (8%). LA is abundant in the food
supply and thus there is no need to supplement.
GLA:The richest sources of GLA are borage (starflower)
oil,GLA (20-24%); evening primrose oil (8-10%); and black
currant oil (15-17%). GLA is present in small amounts in
human breast milk and some foods, but the typical diet
provides very little GLA.
AA:Found in high amounts in eggs, fish and meat, AA is
abundant in the food supply and supplementation is not
usually necessary.

2016-8-13

Omega 3-Omega 6 Ratio

In the human body, LA and ALA compete for
metabolism. Too high intake of LA would reduce the
amount of omega6-desaturase available for the
metabolism of ALA, which may increase the risk of
heart disease.
It has been estimated that the ratio of omega-6
to omega-3 fatty acids in the typical diet is almost
10:1 due to increased use of vegetable oils rich in
omega-6 fatty acids as well as reduced fish
consumption

Health Benefits

Both omega-3 and omega-6 fatty acids are important

components of cell membranes and are precursors to many
other substances in the body such as those involved with
regulating blood pressure and inflammatory responses.
They are necessary in treatment and prevention of:
Heart disease
Arthritis and other joint conditions
Skin disorders
Mental disorders
gastrointestinal disorders, diabetes, obesity, PMS,
mastalgia (breast tenderness), hypertension, multiple
sclerosis, lupus, asthma, allergies and cancer.

Deficiency
Abnormalities in the liver and kidney
Changes in the blood
Reduced growth rates
Decreased immune function
Depression
Skin changes, including dryness and scaliness, Eczema
Mental disorders
Diabetes
Atherosclerosis
Hypertension, PMS, and inflammatory conditions such as
rheumatoid arthritis.

Health Risks of Trans Fat

Increases the amount of harmful LDL (low density
lipoprotein) cholesterol in the bloodstream and
reduces the amount of beneficial HDL cholesterol.
Trans fats create inflammation, which is linked to
heart disease, stroke, diabetes, and other chronic
conditions.
They contribute to insulin resistance, which increases
the risk of developing type 2 diabetes.

Sources of Trans Fat

Commercially baked goods (cookies,

crackers, cakes, muffins, pie crusts, pizza
dough, breads like hamburger buns)
Packaged snack foods (crackers, microwave
popcorn, chips, candy)
Solid fats (stick margarine, vegetable
shortening)
Fried foods (French fries, fried chicken,
chicken nuggets, breaded fish, hard taco
shells)
Pre-mixed products (cake mix, pancake,
chocolate milk)
Anything with partially hydrogenated oil
listed in the ingredients

END