Fatty acids can be classified as follows:

Saturated
Unsaturated
Branched
Substituted
Cyclic
Eicosanoids
• Fatty acids are divided into four groups according
to the length of hydrocarbon chains:

(i) short chain with 2—3 carbons;

(ii) medium chain with 4-12 carbons;
(iii) long chain with 12—20 carbons
(iv) very long chain with more than 20 carbons

Different classes, examples and sources of the fatty

acids are given in table .
Different types of fatty acids (FAs) with examples and sources
Different types of fatty acids (FAs) with examples and sources
• Types of fatty acids

• Saturated F A
• Saturated FAs having 10 carbon or less number of
carbon atoms are called as Lower fatty acids,e.g.
acetic acid , butyric acid ,etc.

• Saturated F A having more than 10 carbon atoms

are called as higher fatty acids,e.g. palmitic acid ,
stearic acid, etc.
• The main sources of saturated fatty acids are dairy
and meat products

• and some vegetable oils, such as coconut and palm

oils (a major source of fat in Latin America and Asia)

• Most experts strongly advise limiting intake of

saturated fats
• Unsaturated fatty acids may be further subdivided
as follows:

• Monounsaturated (monoenoic) acids, containing

one double bond. Example Oleic acid

• Polyunsaturated (polyenoic) acids, containing two

or more double bonds- Arachdonic acid
 Monounsaturated fats

• Triacylglycerols containing primarily fatty acids

with one double bond are referred to as
monounsaturated fat

• Unsaturated fatty acids are generally derived from

vegetables and fish

• When substituted for saturated fatty acids in the

diet, monounsaturated fats lower both total
plasma cholesterol and LDL cholesterol, but
increase HDLs
• This ability of monounsaturated fats to favorably
modify lipoprotein levels may explain, in part, the
observation that Mediterranean cultures,

• with diets rich in olive oil (high in

monounsaturated oleic acid), show a low
incidence of coronary heart disease
.
.
..
Polyunsaturated Fatty Acids (PUFAs) OR Essential
Fatty Acids

• The three polyunsaturated fatty acids (PUFAs),

namely, linoleic, linolenic and arachidonic acids are
called essential fatty acids (EFA).

• These fatty acids are called ‘essential’ because they

cannot be synthesized in the human body.

• They need to be provided in the diet. The human

body is incapable of introducing a double bond
beyond the ninth carbon atom.
• Arachidonic acid, however, can be synthesized
from linoleic acid and is therefore called semi-
essential’ fatty acid.

• PUFAs are necessary for the maintenance of

growth, reproduction and good health.

• Deficiency causes fatty liver and faulty vision.

• The PUFAs occur as structural elements of the

membranes.
• They are precursors …

of leukotrienes and
prostanoids.

• High intake of PUFA tends to lower cholesterol,

prolong blood-clotting time and prevent dermatitis.
Docosahexaenoic acid (DHA) ω3,22:6

•Docosahexaenoic acid (DHA) is a polyunsaturated

fatty acid which is synthesized from α-linolenic or
obtained directly from dietary fish oil.

•This fatty acid is present in high concentrations in

retina, cerebral cortex, testes and sperms.

•DHA is particulary needed for development of the

brain and retina and is supplied via the placenta and
milk.
• In EFA deficency, nonessential polyenoic acids of
the ω9 family replace the essential fatty acids in
…

phospholipids (PL), other complex lipids and

membranes.

• Clinical Aspect:
• Low blood levels of DHA have been reported in
patients with Retinitis Pigmentosa.
ESSENTIAL FATTY ACIDS
 Functions of EFA

1.Synthesis of Ecosanoids

2.Maintenance of structural integrity of

cells

3.Development of retina andbrain

4.Antiatherogenic effect
Leukotrienes Prostaglandins
Thromboxanes
 EFAdeficiency

The syndrome in humans characterized by

Horny eruptions on the posterior

Phrynoderma and lateral parts of limbs, on the
back and buttocks.
Dermatitis
Poor wound healing
 Essential fatty acids

• Two fatty acids are dietary essentials in humans as

double bonds can be introduced at the Δ4, Δ5, Δ6,
and Δ9 positions in most animals, but never
beyond the Δ9 position
– linoleic acid, 18: 2 Δ 9, 12 which is the precursor of
arachidonic acid 20: 4 Δ 5, 8, 11, 14, the substrate for
prostaglandin synthesis
– linolenic acid 18:3 Δ9,12,15, the precursor of other
ω-3 fatty acids important for growth and
development
• A deficiency of linolenic acid results in decreased
vision and altered learning behaviors
• Arachidonic acid becomes essential if linoleic acid
is deficient in the diet

• The effects of polyunsaturated fatty acids (PUFAs)

on cardiovascular diseases is influenced by the
location of the double bonds within the molecule
• Consumption of fats containing ω-6
polyunsaturated fatty acids, principally linoleic acid,
(18:2Δ9, 12) obtained from vegetable oils, lowers
plasma cholesterol when substituted for saturated
fats
• Plasma LDLs are lowered, but HDLs, which protect
against coronary heart disease, are also lowered

• The powerful benefits of lowering LDLs are only

partially offset because of the decreased HDLs

• Nuts, avocados, olives, soyabeans, and various

oils, including sesame, cottonseed, and corn oil,
are common sources of the ω-6 fatty acids

• Linoleic acid, along with linolenic acid are essential

fatty acids required for fluidity of membrane
structure and synthesis of eicosanoids
• A deficiency of essential fatty acids is characterized
by scaly dermatitis, hair loss, and poor wound
healing

• Dietary ω-3 polyunsaturated fats suppress cardiac

arrhythmias, reduce serum triacylglycerols,
decrease the tendency to thrombosis, and
substantially reduce risk of cardiovascular
mortality, but they have little effect on LDL or HDL
cholesterol levels
• The ω-3 polyunsaturated fats (mainly α-linolenic
essential fatty acid), are found in plants and in fish
oil
• Imbalance of omega-6 and omega-3::PUFAs in the
diet is associated with an increased risk of
cardiovascular disease

• The optimal dietary ratio of omega-6 to omega-3

PUFAs is between1 :1 and 4:1, but the ratio in the
diets of most North Americans is closer to 10:1 to
30:1, Ieading to an increased frequency of heart
disease and stroke

• When lipid-rich foods are exposed too long to the

oxygen in air, they may spoil and become rancid
• The unpleasant taste and smell associated with
rancidity result from the oxidative cleavage of
double bonds in unsaturated fatty acids, which
produces aldehydes and carboxylic acids of shorter
chain length and therefore higher volatility

• To improve the shelf life of vegetable oils used in

cooking, and to increase their stability at the high
temperatures used in deep-frying, commercial
vegetable oils are subjected to partial
hydrogenation
• Partial hydrogenation has an undesirable effect:
some cis double bonds are converted to trans
double bonds
• This process converts many of the cis double bonds
in the fatty acids to single bonds and increases the
melting temperature of the oils so that they are
more nearly solid at room temperature (margarine
is produced from vegetable oil in this way)

• There is now strong evidence that dietary intake of

trans fatty acids (often referred to simply as "trans
fats") leads to a higher incidence of cardiovascular
disease

• Avoiding these fats in the diet substantially

reduces the risk of coronary heart disease
• Dietary trans fatty acids raise the level of
triacylglycerols and of LDL ("bad") cholesterol in
the blood,

• and lower the level of HDL ("good")cholesterol and

these changes alone are enough to increase the
risk of coronary heart disease

• Tans fatty acids may have further adverse effects as

they seem, for example, to increase the body's
inflammatory response
• The deleterious effects of trans fats occur at intakes
of 2 to 7 g/day(20 to 60 kcal in a daily caloric intake
of 2000 kcal)

• A single serving of French fries in a restaurant may

contain this amount of trans fatty acids!

• Many other prepared foods, baked goods, and

snacks on the shelves of supermarkets have
comparably high levels of trans fats
 The Mediterranean diet:

• The Mediterranean diet is an example of a diet rich

in monounsaturated fatty acids (from olive oil) and
n-3 fatty acids (from fish oils and some nuts), but
low in saturated fat

• The Mediterranean diet contains seasonally fresh

food,
• with an abundance of plant material,
• low amounts of red meat,
• and olive oil as the principal source of fat
 Branched Chain FA

• Odd and even carbon branched chain fatty acids

occur in animals and plant lipids, e.g.

• Sebaceous glands , Sebum contain branched chain

FA.

• Branched chain FA is present in certain foods ,e.g.

phytanic acid in butter
 Substituted Fatty Acids

• In hydroxy FA & methyl FA one or more of the

hydrogen atoms have been replaced by –OH group
–CH3 group respectively.

• Both saturated and unsaturated hydroxy fatty acids

,particularly with long chains, are found in nature
,e.g.
Cerebronic acid of brain glycolipids,
Ricinoleic acid in castor
 Cyclic Fatty Acids

• Fatty acids bearing cyclic groups are present in

some seeds,e.g.
• Chaulmoogric acid obtained from Chaulmoogra
seeds
• Hydnocarpic acid
• Both of them have been used earlier for long time
for treatment of Leprocy
Properties of Fatty Acids
Structure
• The introduction of a cis double bond causes fatty
acid to ‘kink’ at that position.
Most naturally occurring fatty acids exist as ‘cis’
configuration
Melting Point
• In general, increasing the length of chain increases
the melting point of a fatty acid.
For example butter which contains medium-chain
fatty acids soften at room temperature.

• Addition of double bonds decreases the melting

point.
• Therefore, the presence of unsaturated fatty acids
in membrane lipids helps maintain the fluid
nature of these lipids.
• The melting point is also strongly influenced by the
….

degree of unsaturation.

• The higher the unsaturation, the lower is the

melting point.

• Melting point is lowered if the fatty acid chain is

branched.
Isomerism
• Geometrical isomers (cis and trans isomers) are
formed due to their orientation around the axis of the
double bond.
Oleic acid (cis isomer)
HOOC — (CH2)7— CH
HOOC — (CH2)7— CH
M.P. 13°C
• Margarine and fats used in making french fries
contain trans fatty acids.

• Positional isomers vary with respect to location of

the double bond along the unsaturated fatty acid
chain. This variation may produce many isomers of
the compound. Oleic acid has 15 different positional
isomers.

Solubility
• Soluble in chloroform and benzene.
• Decreases with fall in temperature and rise in chain
length.
Ester Formation
• When fatty acids react with alcohol, esters are
formed.
Palmitic acid + Alcohol → Ethylpamitate

Soap Formation
Soaps are sodium/potassium salts of fatty acids.

Hydrogenation of Unsaturation Fatty Acids

When exposed to hydrogen at high pressure and
temperature (l5O—2OO0C), and in the presence of
nickel and platinum, unsaturated fatty acids get
hydrogenated.
Steam Volatility
•It reduces with increase in length of carbon chains.

Halogenation

• Unsaturated fatty acids absorb halogens in the

following order: Fl > Cl > Br > I.
Oxidation

• Saturated fatty acids are relatively resistant to

oxidation outside the body.
• Unsaturated fatty acids get oxidized in the presence
of air, leading to rancidity.