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5
LIPIDS

Q. What are lipids?

Ans. The lipids are heterogeneous group of compounds related to the fatty acids and are insoluble
in water but soluble in solvents such as ether, chloroform and benzene. The lipids occur widely in
plant and animal kingdom. The lipids include fats, oils, waxes and related compounds. Oils are liquids
at 20°C but fats are solid at 20°C. The fats and oils used almost universally as stored form of energy
in living organisms are highly reduced compounds which are derivatives of fatty acids.
Q. What are Simple Lipids?
Ans. Simple lipids are the esters of fatty acids with various alcohols. If the alcohol is glycerol,
then they are called as fats or neutral fats. If the fat is liquid at ordinary temperature it is called oil.
But if their is alcohol of high molecular weight instead of glycerol than they are called as waxes.
Q. What are fats?
Ans. Fats are the esters of fatty acids with glycerol.

CH2OH HOOC – R1 CH2O.CO.R1

| |
CHOH + HOOC – R2 CHO.CO.R2
| |
CH2OH HOOC – R3 CH2O.CO.R3
Fig. 5.1. Fat molecule (triglyceride).

The chemical structure of fat consists of three different molecules of fatty acids with one
molecule of glycerol. The three different fatty acids (R1, R2, R3) are esterified with the three hydroxyl
groups of glycerol because the polar hydroxyls of glycerols and the polar carboxylate of the fatty acids
are bound in ester linkages, triacyl glycerols are non-polar, hydrophobic molecules insoluble in water.
Q. List different properties of fats.
Ans. The different physical and chemical properties of fats are as follows—
Physical properties
Fats are insoluble in water but readily soluble in ether, chloroform, benzene, carbon tetrachloride.
They are themselves good solvents for other fats, fatty acids etc. and are tasteless, odourless,
colourless and neutral in reaction.They spread uniformly over the surface of water, so their spreading
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effect is to lower surface tension. Their melting points are low.

Chemical properties
Hydrolysis—Hydrolysis of triacylglycerol takes place by lipases producing fatty acids and
glycerols. Phospholipases attack the ester linkage of phospholipids.
O O O
|| || ||
R1 CO–CH2 R1 CO CH2 R1 CO– CH2
O H2O lipase H2O /lipase |
|| CHOH
R2 CO–CH R3COOH R2 CO CH R2COOH |
O CH2OH
||
R3 CO–CH2 CH2OH Monoglyceride
Triglyceride Diglyceride

CH2OH
H2O lipase |
CHOH
R1COOH |
CH2OH
Glycerol
Fig. 5.2. Hydrolysis of fat.

Saponification—Saponification is the hydrolysis of a fat by alkali and the products formed are
glycerol and the alkali salts of fatty acids which are called as soaps.

CH2OCOR1 CH2OH
| |
CH2OCOR2 + NaOH CHOH + 3RCOONa
| |
CH2OCOR3 Alkali CH2OH
Fat Glycerol Soap
Fig. 5.3. Saponification of fat.

The number of milligrams of KOH required to saponify 1 gram of fat or oil is called as its
saponification number.
Acid number—The number of milligrams of KOH required to neutralize the free fatty acids of 1
gram of fat.
Iodine number—It is the amount in grams of iodine absorbed by 100 grams of fat. Thus it is
the measure of the degree of unsaturation of a fat.
Acetyl number—The number of milligram of KOH required to neutralize the acetic acid obtained
by saponification of gram of fat after it had been acetylated. This is a measure of the number of
hydroxy acid groups in the fat.
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Halogenation—The halogen atoms i.e. chlorine, bromine and iodine may be added to the double
bonds of unsaturated fatty acids containing fat.
Rancidity—Nearly all-natural fats are oxidized when exposed to air, light and moisture. They
develop an unpleasant odour and taste. This happens so due to the formation of peroxides at the
double bonds of unsaturated fatty acids. Vitamin E is an important natural antioxidant.
Hydrogenation—Unsaturated plant fats are converted into more saturated and solid fats by
catalytic hydrogenation. This is usually done over finely divided nickel. In the production of margarine
and vegetable shortening, this property is exploited commercially.

H2 gas
Vegetable oil Solid fat
Ni powder/Pressure

CH2O.CO.C17H33 CH2O.CO.C17H35
| |
CHO.CO.C17H33 + 6H CHO.CO.C17H35
| |
CH2O.CO.C17H33 CH2O.CO.C17H35
Triolein (oil) Tristaerin (fat)

Q. Define Waxes.
Ans. Waxes are the esters of fatty acids with higher alcohols and are formed as secretions,
which are mostly protective in functions in many animals. They resemble the fat and are usually
solids. In the human body the commonest waxes are esters of cholesterol. Their constituent acids and
alcohols have usually 24 to 36 carbon atoms.
Q. What are compound lipids? Mention brief classification of compound lipids.
Ans. Compound lipids are the esters of fatty acids containing groups, other than and in addition
to an alcohol and fatty acids. They are further subdivided into
A. Phospholipids
B. Glycolipids
C. Sulpholipids
D. Lipoproteins
E. Aminolipids (Proteolipids)
Phospholipids
These are the compound lipids, which are the esters of fatty acids with glycerol containing an
esterified phosphoric acid and a nitrogen base. They are present in large amounts in nerve tissues,
brain, liver, kidney, pancreas and heart. They form the structures of membranes, matrix of cell wall,
myelin sheath, microsomes and mitochondria. They also act as carriers of inorganic ions across the
membranes and helps in blood clotting. They act as prosthetic group to certain enzymes and increases
the rate of fatty acid oxidation.
Glycolipids
These contain an amino alcohol (sphingosine or isosphingosine) attached with an amide linkage to
a fatty acid glycosidically to a carbohydrate moiety (sugars, amino sugar, sialic acid ). They are
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further classified into

1. Cerebroside
2. Ganglioside
1. Cerebrosides
Cerebrosides occur in large amounts in the white matter of brain and myelin sheath of nerve. A
cerebroside is considered to be built on the following lines.

Fatty acid of high molecular weight

Sphingosine

Usually galactose but sometimes it may be glucose

There is no glycerol, no phosphoric acid and no nitrogenous base. Thus a cerebroside on

hydrolysis yields
a. A sugar usually galactose.
b. A high molecular weight fatty acid.
c. The alcohol, sphingosine or dihydrosphingosine.
Thus they contain nitrogen although there is no nitrogenous base.
Individual cerebrosides are differentiated by the kinds of fatty acids in the molecule. Four types
of cerebrosides have been isolated and their fatty acids have been identified.
(a) Kerasin—It contains lignoceric acid C23H47COOH as fatty acid.
(b) Cerebron or Phrenosin—It contains hydroxy lignoceric acid and also called as cerebronic
acid.
(c) Nervon—It contains an unsaturated homologue of lignoceric acid called nervonic acid
C23H45COOH.
(d) Oxynervon—It contains hydroxy derivative of nervonic acid.
2. Gangliosides
Gangliosides have been isolated from ganglion cells, neuronal bodies and dendrites, spleen and
RBC stroma. The highest concentrations are found in grey matter of brain. Although the exact
structures of gangliosides are not definitely established but they contain ceramide (sphingosine fatty
acids) glucose or galactose, N-acetyl galactosamine and sialic acid. Some gangliosides also contains
dihydrosphingosine or gangliosine in place of sphingosine. The gangliosides can serve as specific
membrane binding sites (receptor sites) for circulating hormones and thereby influences various
biochemical processes in the cell.
Sulpholipids
These lipids are characterized by possessing sulphate groups. In general they appear to be sulfate
esters of glycolipids, the sulphate group is esterified with OH group of hexose moiety of the molecule.
Lipoproteins
These are the lipid molecules conjugated with the protein molecules. They contain triacylglycerol
(45%) phospholipids (35%) cholesterol and cholesteryl esters (15%) free fatty acids (less than 5%)
and also proteins in combination. The density of lipoproteins increases as the protein content rises and
the lipid content falls and the size of the particle becomes smaller. Lipoproteins may be separated on
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the basis of their electrophretic properties and may be identified more accurately by means of
immunoelectrophoresis. Four major groups of lipoproteins have been identified which are important
physiologically and in chemical diagnosis in some metabolic disorders of fat metabolism. These are
(a) Chylomicrons
(b) Very low density lipoproteins (VLDL)
(c) Low density lipoproteins (LDL)
(d) High density lipoproteins (HDL)
(e) Chylomicrons and VLDL
The predominant lipid is triacyl glycerol (50%) and cholesterol (23%). The concentrations of
these are increased in artherosclerosis and coronary thrombosis etc. The protein moiety in lipoprotein
is known as apoprotein, which constitues nearly 60% of some HDL and 1% of chylomicrons. Many
lipoproteins contain more than one type of apoprotein polypeptide. The larger lipoproteins such as
chylomicrons and VLDL consist of lipid core of non-polar triacylglycerol and cholesteryl ester
surrounded by more polar phospholipid, cholesterol and apoproteins.
The lipoproteins help in transfer of lipids to tissues. They also maintain the structural integrity of
cell surface and subcellular particles like mitochondria and microsomes.
Q. Write a note on derived lipids.
Ans. Derived lipids are the derivatives of simple and compound lipids, which still possess the
general characteristics of lipids. There are further classified into
(a) Fatty acids
(b) Steroids and sterols
(a) Fatty acids
The fatty acids are carboxylic acids with hydrocarbon chain of 4 – 36 carbons. In some fatty
acids, this chain is fully saturated i.e. contains no double bond, and unbranched, others contain one
or more double bonds. A few contains 3 carbon rings or hydroxyl groups.
The physical properties of the fatty acids, and of compounds that contain them are largely
determined by the length and degree of unsaturation of the hydrocarbon chain. The nonpolar
hydrocarbon chain accounts for the poor solubility of fatty acids in water. The longer the fatty acyl chain
and the fewer the double bonds, the lower the solubility in water. The carboxylic acid group is polar (and
ionized at neutral pH), and accounts for the slight solubility of short chain fatty acids in water.
There are 2 types of fatty acids.
Saturated fatty acids
They contain no double bond and have general formula C nH 2n+1COOH. Saturated fatty acids
having 10 carbon or less number of carbon atoms are called as lower fatty acids for e.g. acetic acid,
butyric acid. Saturated fatty acids having more than 10 carbon atoms are called as higher fatty acids
presents some saturated fatty acids occurring widely in nature.
Unsaturated fatty acids
These are the fatty acids which posses one or more than one double bonds in them. The
common examples of unsaturated fatty acids are palmitoleic acid, oleic acid and Eicosanoids
Q. What are Eicosanoids?
Ans. Eicosanoids are derived from eicosapoly enoic fatty acid.
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Eicosapoly enoic fatty acid

Prostanoids (A) Leukotrienes (B)

(1) Prostaglandins (PGs)

(2) Prostacylins (PGI)
(3) Thromboxanes
Prostanoids
These include prostacyclins (PGI) and thrombxanes (TX). These prostanoids virtually exists in all
mammalian tissues and acts as local hormones. They have important physiological and pharmacological
activites.
Prostaglandins
The prostaglandins are relative derivatives of hypothetical molecule C 20 (Prostanoic acid). All
prostaglandin are 20C fatty acid containing a cyclopentane ring on parent saturated acid called
prostanoic acid and have OH group at 15 position and trans double bond at 13 position.
Prostacyclins (PGI)
They are formed in vascular endothelium and continuously formed in heart and kidney. They are
formed from cyclic endoperoxide PGH2 by the reaction of micosomal prostacyclin synthetase. They
decrease blood pressure and protect coronary arteries. They increase renal blood flow and stimulate
rennin production.
Thromboxanes
They contract smooth muscles of blood vessels, GI tract, uterus, bronchioles.
Q. What are Leukotrienes?
Ans. The Leukotrienes are the second group of eicosanoid derivatives formed via lipoxygenase
pathway rather than cyclization of the fatty acid chain. They are characteized by the presence of three
conjugated double bond. They are stimulators of mucus secretion and are responsible for
vasoconstriction of bronchial muscles. The most common example of leukotrine is prostaglandin E 2
(PGE2).
Q. Define Essential Fatty Acids.
Ans. The essential fatty acids are the polyunsaturated fatty acids, which are not synthesized in the
body but are taken from the natural sources. They are essential for the growth and health. The linoleic
acid, linolenic acid and arachidonic acid are the essential fatty acids. The essential fatty acids of
vegetable oils have low melting points and iodine number. They become saturated fatty acids on
hydrogenation and thus oils become solid fats. These along with the lipids constitute the structural
elements of the tissues. The deficiency of these acids in the diet causes eczema in babies. They retard
artheroclerosis. They also affect the prolongation of clotting time and increase the fibrinolytic activity.
Q. What are steroids and sterols?
Ans. The steroids are often associated with fat. All of the steroids have a similar cyclic nucleus
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which resembles phenanthrene to which cyclopentane ring is attached. It is referred to as cyclopentano

perhydrophenathrene nucleus.

18
12 17
11 16 Cyclopentane ring
1 9
13
14
15
}
2 10 8
3
5 7
4 6
}
Phenanthrene ring
Fig. 5.4. Cyclopentanoperhydrophenathrene nucleus.

A side chain at position 17 is usual. If the compound has one or more OH groups and no
carbonyl or carboxy groups it is called as sterol. Most important sterol in human body is cholesterol.
Q. Write in brief the structure, properties and functions of Cholesterol.
Ans. The cholesterol is the most important sterol in the body. Its molecular formula in C27H45OH.
It possesses the cyclopentanoperhydrophenathrene nucleus with OH group at C 3

CH3 CH3
|
CH3 CH2 – (CH2)3 – CH
|
CH3
17
CH3 13

3 5

OH 6
Cholesterol
It has an unsaturated double bond between C5 and C6 with two methyl groups at C10 and C13. It
also has 8-carbon side chain attached to C17. Cholesterol occur both in free form and in ester form
in which it is esterified with fatty acids at –OH group at C3 position. The ester form of cholesterol is
also referred as bound form while free cholesterol is equally distributed between plasma and red blood
cells but the latter do not contain esters.
Q. Write a note on the biological significance of lipids.
Ans. The lipids have several important biological functions.
1. Lipids serve, as the reservoir of energy because of their high-energy content (9 kcal/gm).
2. Lipids form the structural components of cell membranes.
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3. Lipids forms the protective coating on the surface of many organs such as kidney. They
facilitate absorption of the fat soluble vitamin i.e. A, D and K.
4. Lipoproteins and glycolipids are essential for maintaining cellular integrity.They produce
metabolites through oxidation in the tissues, which are used in the interconversion of
substance.