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Lipids

Definition
Fats, oils and waxes belong to the group of
naturally occurring compounds called Lipids
(Greek, lipos= fat).

Lipids are those constituents of animals and


plants which are soluble in organic solvents such
as ether, chloroform, carbon tetrachloride,
benzene, hexane etc., but insoluble in water.
The lipids which yield fatty acids and alcohols on
hydrolysis with aqueous base (saponified) are
referred as Simple Lipids.

These can be further divided into two classes


(a) Fats and Oils : yield long-chain fatty acids
and glycerol upon hydrolysis
(b) Waxes: yield long-chain fatty acids and long-
chain alcohols upon hydroloysis.
COMPOUND LIPIDS: Esters of fatty acids containing
groups in addition to an alcohol and a fatty acid.

a. Phospholipids: Lipids containing, in addition to fatty


acids and an alcohol, a phosphoric acid residue.
They frequently have nitrogen containing bases and
other substituents.
glycerophospholipids : alcohol is glycerol
sphingophospholipids : alcohol is sphingosine.

b. Glycolipids (glycosphingolipids): Lipids containing a


fatty acid, sphingosine, and carbohydrate.

c. Other complex lipids: sulfolipids ;aminolipids.


Occurrence
Fats and oils come from a variety of sources
animals, plants and marine organisms.
Plants- store large quantities of fats in their seeds,
roots & fruits
Cotton seeds, castor beans, peanuts, coconuts &
olives have high fat content.
Animals- fat deposits found mostly under the skin &
around the intestines & kidneys.
Lard (fat of hogs) & tallow (fat of sheep & horses)
Marine Oils- Obtained from water animals -
sardines, herrings, salmons, whales, dolphins, seals,
porpoises
Composition of fats
Fats & oils are triesters formed from glycerol and
long-chain carboxylic acids

General structure

R,R, R: parts of higher fatty acids forming ester


with glycerol
A triester of glycerol is called a triglyceride or
glyceride.
If all the R groups are identical, the triester is
designated as a Simple glyceride
if they are not a Mixed glyceride
Fatty acids that go to form the fat or oil
molecules (glycerides) have carbon chains with
only even number of carbon atoms.
Most common fatty acids have unbranched
carbon chains of 14, 16 or 18 carbons.
Chains: saturated / unsaturated (1 or more
double bonds)
Reactions of Fats and oils
Reactions are those of ester groups in triplicate &
Carbon-carbon double bonds
Hydrolysis: Triglyerides easily hydrolysed by
enzymes called lipases (catalysts) in the
digestive tracts of human beings and animals to
give fatty acids and glycerol
Saponification: triglycerides are hydrolysed
(saponified) by alkalis, glycerol plus the salts of
fatty acids are produced.
the sodium or potassium salts are obtained which
are termed soaps.
Hydrogenation/ Hardening of Oils : On catalytic
hydrogenation, hydrogen adds across the
carbon-carbon double bonds of the acid
components of triglycerides.
Result in formation of saturated glycerides solid
fat at R.T
Hydrogenolysis (Reduction to Alcohols)
Upon treatment with hydrogen at high pressure
and temperature in the presence of copper
chromite (CuCr2O4) as catalyst, glycerides
split up like other esters.
Products: glycerol and the reduction products of
the fatty acid, along chain alcohols.

Hydrogenolysis: hydrogenation involving


cleavage
Addition of Halogens (Halogenation)
Unsaturated glycerides add halogens to give the
corresponding dihalide
Unsaturated glycerides on treatment with iodine
in the presence of mercuric chloride as catalyst,
give diiodides
Rancidity
Rancid is applied to any fat or oil that develops a
disagreeable odour when left exposed to warm,
moist air for any length of time.
Rancidification caused by 2 types of reaction:
Oxidation & Reduction
Oxidative Rancidification: involves oxidation of carbon-
carbon double bonds in fats and oils to produce
volatile carboxylic acid

Hydrolytic Rancidification: involves hydrolysis of one or


more ester linkages in fats & oils to produce original
acid
Drying
When highly unsaturated oils are exposed to air,
they undergo oxidation and polymerization to
form a thin waterproof film.
Such oils are called- Drying oils
Reaction referred as: Drying

Linseed oil, the most widely used drying oil,


contains about 63 per cent of its fatty acids as
linoleates.
Determination of analytical values for
fats and oils
Saponification Number
is an arbitrary unit that is defined as the Number
of milligrams of potassium hydroxide required
to saponify one gram of the fat or oil.

Since there are three ester bonds in a molecule


to hydrolyse, three equivalents of potassium
hydroxide are needed to saponify one molecular
weight of any fat or oil.
If M be the molecular weight of the
fat, the saponification number=
168,000/M.
Iodine Number: defined as the Number of
grams of Iodine which will add to 100 grams of
fat or oil
extent of unsaturation in a fat or oil is expressed
in terms of its Iodine Number
Acid Number
The acid number (or value) of a fat or oil tells the
amount of free fatty acids present in it.

The acid number is expressed as the Number of


milligrams of potassium hydroxide required to
neutralise one gram of fat.

determined by dissolving a weighed quantity of


the fat in ethanol and titrating the solution
against standard alkali.