Contents

1. Introduction.
2. Classification of lipids
3. Reactions of fatty acids and lipids
4. Essential fatty acids
5. Pharmaceutical importance of lipids
 1. Simple lipids
1. Fats
 These are triesters of fatty acids with
glycerol.
 Also called triglycerides, triglycerol or
neutral fats.
2. Waxes
 These are esters of fatty acid with
alcohol (higher molecular weight
monohydric) other than glycerol.
2. Compound or complex lipids
 Esters of fatty acids containing groups in addition to
an alcohol and a fatty acid.
1. Glycolipids
 Lipids containing carbohydrate moiety are called
glycolipids.
 They contain a special alcohol called sphingosine or
sphingol and nitrogenous base in addition to fatty
acids.
 These are of two types:
• Cerebrosides
• Gangliosides

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2. Phospholipids
 Lipids contain, in addition to fatty acids and
alcohol, a phosphoric acid residue. They
frequently have nitrogen-containing bases and
other substituents.
 Example: Lecithin and cephalin
 Based on type of alcohol present they are of two
types:
I. Glycerophospholipid
II. Sphingophospholipid
3. Derived lipids
 Derivatives obtained by hydrolysis of simple and
complex lipids.
 These include
• Diacylglycerol
• Fatty acids
• Alcohols
• Sterols
• Vitamin D, E, K
• Carotenoids
• Terpenes
 Fatty acids
 Fatty acids (FA) are aliphatic carboxylic acids and
have the general formula, R—CO—OH, where
COOH (carboxylic group) represents the functional
group.
 Depending on the R group (the hydrocarbon chain),
the physical properties of fatty acids may vary.
Fatty acids typically contain between 4 to 20 carbon.
The number is usually always even

nonpolar polar

9
 Types of fatty acids
1. Saturated FA
2. Unsaturated FA
1. Saturated fatty acids
 Those which contain no double bonds.
 Their general formula is CnH2n+1 COOH
 Examples
• Acetic acid CH3COOH
• Propionic acid C2H5COOH
• Butyric acid C3H7COOH
• Caproic acid C5H11COOH
• Palmitic acid C15 H31COOH
• Stearic acid C17 H35COOH and so on.
 Saturated fatty acids having 10 carbon or less
number of carbon atoms are called as lower fatty
acids, e.g. acetic acid, butyric acid, etc.
 Saturated fatty acids having more than 10 carbon
atoms are called higher fatty acids,
e.g. palmitic acid, stearic acid, etc
2. Unsaturated fatty acids
 Those which contain one or more double bonds.
 They are mono or polyunsaturated FA.
I. Monounsaturated FA contains one double
bond such as oleic acid.
II. Polyunsaturated FA contains more than one
double bond such as linoleic acid.
 Essential Fatty Acids
 Three polyunsaturated fatty acids are called
essential fatty acids.
• linoleic acid
• linolenic acid and
• arachidonic acid
 They cannot be synthesized in the body and
must be provided in the diet.
 Lack of EFA in the diet can produce growth
retardation and other deficiency
manifestation symptoms.
Properties of fatty acids
1. Hydrogenation
 Unsaturated fatty acid converted to
corresponding saturated FA by the addition of
hydrogen.

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2. Halogenation
 When treated with halogen, unsaturated FA are
converted into halogenated FA.

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3. Salt formation
 Saturated and unsaturated FA form salts with
alkali
 Na and K salt of long chain FA are called soaps
4. Ester formation
 Both saturated and unsaturated FA form esters
with alcohols.
 Such as diglycerides, triglycerides
5. Oxidation of fatty acids
 All fatty acids undergo oxidation in the body to
give energy.
 Beta-oxidation is the major process by which acids
are oxidized
 However, the unsaturated fatty acids can undergo
auto-oxidation, due to the presence of the highly
reactive double bonds, and a variety of products
are formed.
Triglycerides/Neutral Fat
 Neutral fats are also called triacylglycerols
(TAG) or triglycerides (TG). These are esters of
trihydric alcohol, glycerol with fatty acids.
 Naturally occurring fats and oils are mixtures
of triglycerides.
 They are hydrophobic and insoluble in water.
 Oils are liquids at 20C; they are triacylglycerols,
which contain a higher proportion of unsaturated
fatty acids or short chain triglycerides. Oils are
generally of plant origin.
 Fats are solids at room temperature and contain
mainly saturated long-chain fatty acids. Fats are
mainly of animal origin.
 When the constituent fatty acids have a higher chain
length and are predominantly saturated, ‘hard fat' is
formed
 Fats containing medium-chain triacylglycerols or
unsaturated fatty acids are soft fats, e.g. butter, and
coconut oil.
Chemical reactions of Fats and Oils
1. Saponification and saponification number
 When triacylglycerols are hydrolyzed by alkali, the process is
known as saponification. The products are glycerol and
soaps.
 Saponification number is defined as the number of
milligrams of potassium hydroxide required to saponify one
gram of fat.
 Human fat has a saponification number of 194–198,
and butter has 210–230
The amount of alkali needed to saponify a given quantity
of fat will depend upon the number of –COOH group
present.
• Thus fats containing short-chain fatty acids will have more –
COOH groups per gram than long-chain fatty acids and this
will take up more alkali and hence will have a higher
saponification number.
Saponification
2. Iodine number
 Iodine number of a fat is defined as the
number of grams of iodine taken up by 100
grams of fat.
 It is an index of the degree of unsaturation and
is directly proportional to the content of
unsaturated fatty acids.
 Higher the iodine number, higher is the degree of
unsaturation, e.g. iodine number of butter is 28,
and that of sunflower oil is 130.
3. Acid number
 Number of mg of KOH required to neutralize the
fatty acids in a gm of fat is known as the acid
number. It gives degree of rancidity of given fat.
4. Rancidity
• Fats and oils have a tendency to become rancid.
The term rancidity refers to the appearance of an
unpleasant smell and taste for fats and oils.
• Hydrolytic rancidity is due to partial hydrolysis of the
triacylglycerol molecules due to traces of hydrolytic
enzymes present in naturally occurring fats and oils.
• Oxidative rancidity is the result of partial oxidation
of unsaturated fatty acids with resultant formation
of epoxides and peroxides
 WAXES
 They are esters of higher fatty acids with higher
monohydroxy aliphatic alcohols and so have
very long straight chains of 60–100 carbon
atoms.
 They are used as the base for the preparation of
cosmetics, ointments, polishes, lubricants and
candles.
 Example: bees wax, carnuba wax
 Phospholipids
 They contain glycerol, fatty acids, phosphoric acid
residue, and a nitrogenous base e.g
Phosphoglycerides
 Structural: Phospholipids participate in the
lipoprotein complexes which are thought to
constitute the matrix of cell walls and membranes,
the myelin sheath, and of such structures as
mitochondria
 Role in enzyme action: Certain enzymes require
tightly bound phospholipids for their actions, e.g.
mitochondrial enzyme system involved in oxidative
phosphorylation.
Role in blood coagulation: Phospholipids play
an essential part in the blood coagulation
process.
Insulation: Phospholipids of myelin sheaths
provide the insulation around the nerve
fibers
Cofactor: Phospholipids are required as a
cofactor for the activity of the enzyme
lipoprotein lipase and triacylglycerol lipase.
 Steroids and sterols
 The steroids are often found in association with
fat.
 All of the steroids have a similar cyclic nucleus
resembling phenanthrene (rings A, B and C) to
which a cyclopentane ring (ring D) is attached.
 It is designated as a cyclopentano perhydro-
phenanthrene nucleus
 Cholesterol
 Cholesterol is the most important sterol in human
body. Its molecular formula is C27H45OH.
 It possesses “cyclopentanoperhydrophenanthrene
nucleus”. It has an –OH group at C3.
 It has an unsaturated double bond between C5
and C6.
 It has two –CH3 groups at C10 and C13.
 It has an eight carbon side chain attached to C17.
 We need a small amount of blood cholesterol because:
 It builds the structure of cell membranes.
 Make hormones like estrogen, testosterone, and
adrenal hormones.
 Help your metabolism work efficiently, for example,
cholesterol is essential for your body to produce vitamin
D.
 Lipoproteins
 Lipoproteins contain lipids and proteins.
 They include:
• Chylomicrons transport primarily triglycerides
from the digestive tract.
• LDLs (low-density lipoproteins) transport
cholesterol, triglycerides, and phospholipids
from the liver to other tissues.
• HDLs (high-density lipoproteins) transport
cholesterol and phospholipids back to the liver.
 The HDL and LDL levels in the blood can be used
to assess one’s risk for atherosclerosis.
Importance of lipids
 References
• Murray R, Rodwell V, Bender D, Kathleen M,
Botham P, Weil A et al. Harper's Illustrated
Biochemistry. 28th Ed. Print-Hall; 2009
• Illustrated Biochemistry, 4th Ed, J Lippincot
Company,
• M N Chaterjea, Medical Biochemistry, 7th Ed,
Jaypee Brothers Medical Publishers, New Delhi,
2007
• A text book of Biochemistry, Mushtaq Ahmad