Nangarhar University

Veterinary Science Faculty

Pre-Clinic Department

Lipids
Prepared by :Fazal Akbar Khalili

09/13/2023 1
 Introduction
• Lipids comprise very heterogeneous group of compounds which are insoluble in water
but soluble in non-polar organic solvents such us benzene, chloroform, and ether.
• They are either hydrophobic (nonpolar) or amphipathic (containing both nonpolar and
polar regions).

According to Bloor, lipids are compounds having the following characteristics:

• They are insoluble in water
• Solubility in one or more organic solvents, such as ether, chloroform, Benzene,
Acetone which are generally called as fat "solvents".
• Some relationship to the fatty acids as esters.
• Possibility of utilization by living organisms.
09/13/2023 2
 Biological Importance of Lipids
• ENERGY SOURCE: Lipids act as fuel in the body. Lipids yield 9.5Kcal/gram whereas
proteins and carbohydrates yield only about 4Kcal/gram.
• LIPID STORAGE: Since lipids are insoluble in aqueous solution, they can be stored
easily in body.
• INSULATION: Fats are usually stored in the subcutaneous layers. They exert insulating
property. This is found to be useful especially useful in those animals living in the cold
climate like whale etc., Lipids stored around internal organs found to be padding and
protecting the organs.
• STRUCTURAL ROLE: Lipids play a vital role in structure by being the important
component of lipid bilayer in membrane. Especially phospholipids and cholesterols are
important.
• ENDOCRINE FUNCTION: Hormones like adrenocorticoids, mineralocorticoids, sex
hormones and vitamin D were found to be synthesized from lipids like cholesterol.
09/13/2023 3
 Biological Importance of Lipids
• VITAMIN ABSORPTION: Lipids are essential for the absorption of fat soluble
vitamins like vitamin A, D, E and K.
• NERVOUS SYSTEM: Lipids are found to be important constituent of the nervous
system because nerve cells found to contain greater amount of lipids they play vital role
nerve cell insulation and impulse conduction.
• ANTIBIOTIC ACTIVITY: Squalamine, a steroid from Sharks' blood, has been found
to be antifungal and antibacterial activity.
In addition, they are commercially important in the form of soaps, detergents, greases
and the various oils of the paint industries.
09/13/2023 4
 Classification
There is no single, internationally accepted system of classification for the lipids
available. Bloor's classification

09/13/2023 5
 Classification

09/13/2023 6
 Simple lipids
Simple lipids are esters of fatty acids with various alcohols. They contain mainly fatty
acids and alcohols alone. They are further divided into two classes namely, Neutral fats
and waxes.
Neutral Fats: They are triesters of fatty acids with glycerol. Triacylglycerol is an example
for Neutral fats. They are also called as tri acyl glycerol or triglycerides.

09/13/2023 7
 Simple lipids
• Depending upon the fatty acid residues in glycerol, there are two types of fats namely
simple triglycerides and mixed triglycerides.
• If all three fatty acids are the same, the triglyceride is called simple triglycerides. E.g.
in Olive oil, the fatty acid is oleic acid then it was named as triolein. Similarly
tristearin contains three stearic acid residues.

09/13/2023 8
 Simple lipids
If more than one fatty acid was S. No ANIMAL FAT PLANT FAT
esterified with glycerol then the fat is Relatively rich in saturated fatty Relatively rich in unsaturated
1
named as mixed triglycerides. The acids fatty acids.
name of the fat depends upon the Solid at ordinary room
2 Liquid at room temperature
substituted fatty acid and its position. temperature

Mixed triglycerides exhibit isomerism 3

These have usually low iodine These have usually high iodine
number number
depending on the position occupied
by the different fatty acid residues. 4
These have usually high
Reichert-Meissl Number
These have low RM number

These are stored mainly in liver These are stored mainly in

5
and bone marrow seeds and fruits

Oxidative rancidity is observed Oxidative rancidity is observed

6
more frequently less frequently
Example: Olive oil, Caster
7 Example : Butter fat, Beef fat
09/13/2023 oil 9
 Simple lipids
Properties of Fats: Properties of fats and oils depend upon the fatty acids and alcohol
which are present in it.
Physical Properties:
• Fats containing saturated fatty acids are solid at room temperature.
• When pure, the fats are colorless, virtually odorless and possess an extremely bland
taste.
• The fats are only sparingly soluble in water.
• The melting point of fats depends on the chain length and the degree of unsaturation.
Melting point increases with increase in their chain length but increase in the degree
of unsaturation lowers melting point.
• The specific gravity of the fats is less than 1 i.e. 0.86. Therefore, they float on water
surface.

09/13/2023 10
 Simple lipids
Properties of Fats:
Chemical Properties:

Chemical properties of fats studied under three different headings namely

1. Reactions due to COOH group

2. Reactions due to Double bonds

3. Reactions due to OH group

09/13/2023 11
 Simple lipids
Chemical Properties:
1. Reactions due to COOH group:
A. Hydrolysis by Enzyme: The fats are hydrolyzed by

the enzymes lipases to yield fatty acids and glycerol.

This reaction occurs in three steps at a slightly alkaline
pH. The fats first split to produce diglycerides, part of
these are then split to monoglycerides. Finally, part of
the monoglycerides split to yield to glycerol and fatty
acid
09/13/2023 12
 Simple lipids
Chemical Properties:
1. Reactions due to COOH group:
B. Hydrolysis by Alkali (Saponification):
• The hydrolysis of fats by alkali is called as
saponification. This reaction results in the
formation of glycerol and salts of fatty acids which
are called as soaps.
• The soaps are of two types namely hard and soft.
• Hard soaps such as the common bar soaps are the
sodium salts of the higher fatty acids.
• Soft soaps are the potassium salts of higher fatty
acids.
09/13/2023 13
 Simple lipids
Chemical Properties:
1. Reactions due to COOH group:
B. Hydrolysis by Alkali (Saponification):
• The fatty acid salts of calcium, magnesium, zinc and lead are, however,
insoluble in water.
• Calcium soaps are used industrially as lubricating greases.
• Zinc soaps are employed in the manufacture of talcum powder and other
cosmetics.
• Lead and magnesium soaps are used in paints industry to hasten the process
drying.

09/13/2023 14
 Simple lipids
Chemical Properties:
1. Reactions due to COOH group:
C. Hydrolysis by Acid:

• When fats are hydrolyzed by acid, it yields only fatty acids and glycerol

09/13/2023 15
 Simple lipids
Chemical Properties:
1. Reactions due to COOH group:
D. Hydrolysis by Microbes
• When butter or other fats are stored, they often become rancid and hence unpalatable.
• Rancidity is caused by the growth of microorganisms which secrete enzymes like lipases.
• These split the fats into glycerol and free fatty acids. The fatty acids impart unpleasant
odour and flavor to the fat.
• Since, rancidity aroused due to the hydrolysis reaction, it is known as hydrolytic
rancidity.
• However, butter may be prevented from becoming rancid by refrigeration or by exclusion
of water.

09/13/2023 16
 Simple lipids
Chemical Properties:
2. Reactions due to Double bond:
A. HYDROGENATION OF FATS:
• Hydrogenation is a commercial chemical process to add more hydrogen to natural
unsaturated fats to decrease the number of double bonds and retard or eliminate the
potential for rancidity.
• Unsaturated oils, such as soybean oil, which contain unsaturated fatty acids like oleic
and linoleic acid, are heated with metal catalysts in the presence of pressurized
hydrogen gas. Hydrogen is incorporated into the fatty acid molecules and they become
saturated with hydrogen. Oleic acid (C18:1) and linoleic acid (C18:2) are both converted
to stearic acid (C18:0) when fully saturated.

09/13/2023 17
 Simple lipids
Chemical Properties:
2. Reactions due to Double bond:
B. Halogenation:
• Unsaturated fatty acids and their esters can take up halogens like Bromine and Iodine at
their double bonds at room temperature in acetic acid or methanol solution.

09/13/2023 18
 Simple lipids
Chemical Properties:
2. Reactions due to Double bond:
C. Oxidation:
Unsaturated fatty acids are susceptible to
oxidation at their double bonds. Oxidation may
be carried with ozone, KMnO4 and oxygen itself.
i) With ozone:
Ozone interacts with unsaturated fatty acids
and form ozonide as an unstable intermediate
and which is later cleaved by water to give two
molecules of aldehydes.
09/13/2023 19
 Simple lipids
Chemical Properties:
2. Reactions due to Double bond:
C. Oxidation:
ii) With KMnO4 :
Under mild conditions, the glycols are formed at the sites of double bonds.

09/13/2023 20
 Simple lipids
Chemical Properties:
2. Reactions due to Double bond:
C. Oxidation:
iii) With oxygen:

Oils containing highly unsaturated fatty acids are spontaneously oxidized by atmospheric

oxygen at ordinary temperature. The oxidation takes place slowly and results in the formation of
short chain fatty acids and aldehydes which give a rancid taste and odour to the fats. This type of
rancidity(The unpleasant odour and taste developed by most natural fats on aging is referred to
as rancidity) or rancidification is called oxidative rancidity and is due to a reaction called
autoxidation.
09/13/2023 21
 Simple lipids
Chemical Properties:
3. REACTIONS DUE TO HYDROXYL GROUP:
A. Dehydration (Acrolin test):

Fats when heated in the presence of a dehydrating

agent, NaHSO4 or KHSO4 produce unsaturated

aldehydes called acrolin from the glycerol moiety.
Acrolin easily recognized by its pungent odour and
thus forms the basis of the test for the presence of
glycerol in fat molecule.
09/13/2023 22
 Simple lipids
2. Waxes:
• The word "wax" originate from the Old English word "Weax" meaning " the material of the honeycomb" i.e.
beewax.
• Waxes are esters of long chain fatty alcohols (reduced fatty acids) and fatty acids.
• The fatty acids rang in between C14 and C36 and the alcohols range from C16 to C36.
• Waxes are saponified with great difficulty than fats and are not attacked by lipase.
• Bee wax: It contains esters derived from alcohols having 24 - 30 carbon atoms example palmitate of myricyl
alcohol and n-hexacosanol.
• Spermaceti: It is obtained from the head of the sperm whale. It is rich in ester of acetyl alcohol and palmitic
acid. It is used in the manufacture of candle. CH3 (CH2)14COOC16H33

• A wax found in blood plasma is found to have cholesteryl palmitate i.e. ester of cholesterol and palmitic acid.

09/13/2023 23
 Simple lipids
2. Waxes:
• Sperm oil: It is a liquid wax and occurs with spermaceti in the sperm whale. It is a
valuable lubricant used for delicate instruments such as watches. It does not become
gummy like other normal oils.
• Carnauba Wax: It is the hardest known wax. It consists mainly of fatty acids esterified
with tetracosanol and tetratriacontanol. It is found in the leaves of the carnauba palm of
Brazil. It is used as an ingredient in the manufacture of various wax polishes. Because
waxes are very inert chemically, they make an excellent protective coating.
• Lanolin: It is obtained from wool and is used in making ointments and salves. It
readily forms an emulsion with water and for this reason makes it possible for drugs
which are soluble in water to be incorporated into salves.
09/13/2023 24
 Simple lipids
PHYSIOLOGICAL IMPORTANCE OF WAXES:
1. The most important physiological function of waxes is as a protective agent on the
surfaces of animals and plants.
2. Waxes are found on the surface of feathers and hair with the result they remain soft and
pliable.
3. Waxes prevent aquatic animals from becoming wet. Because of this water related birds
like duck able to maintain dryness.
4. Waxy coating on the surface of plants protects them from excessive loss of moisture.
5. Waxy coating prevents the infection of plants from fungi and bacteria which can cause
diseases.

09/13/2023 25
 Compound lipids
PHOSPHOLIPIDS
• Phospholipids are of two types namely glycophospholipids and spingolipids depending
upon the nature of the alcohol.
• If glycerol present as alcohol then they will be called as glycerophospholipids or
glycophospholipids.
• if spingosine present as alcohol then they are known as spingophospholipids or
spingolipids.

09/13/2023 26
 Compound lipids
Functions of PHOSPHOLIPIDS
• Structural Role: 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 and microsomes.
• 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 important part in the blood
coagulation process. They are required at the stage of conversion of prothrombin by
active factor X and in the activation of factor VIII by activated factor IX.
• Role in lipid absorption in intestine

09/13/2023 27
 Compound lipids
Functions of PHOSPHOLIPIDS
• Role in transport of lipids from intestines: Exogenous triglycerides is carried as
lipoprotein complex, chylomicrons, in which phospholipids takes an active part.
• Role in transport of lipids from liver: Endogenous triglycerides are carried from Liver
to various tissues as lipoprotein complex. Phospholipid is required for the formation of
the lipoprotein complex.
• Role in electron transport: Probably phospholipid helps to couple oxidation with
phosphorylation and maintains electron transport enzymes in active conformation and
proper relative positions.
• Lipotrophic action of Lecithin: Choline acts as a lipotropic agent as it can prevent
formation of fatty liver. As lecithin can provide choline it acts as a lipotropic agent.
09/13/2023 28
 Compound lipids
Functions of PHOSPHOLIPIDS
• Membrane phospholipids: Phospholipids of membrane are hydrolyzed by
phospholipase A2 and provide the unsaturated fatty acid arachidonic acid, which is
utilized for synthesis of prostaglandins and leukotrienes.
• 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.
09/13/2023 29
 Compound lipids
GLYCEROPHOSPHOLIPIDS:
• They consist of an alcohol (glycerol), one or two molecules of fatty acid, and a
phosphoric acid compound. Phospholipids are fat derivatives in which one fatty acid has
been replaced by a phosphate group and one of several nitrogen-containing molecules.
• They are found in all plants and animals and include such substances as lecithin,
cephalin, and sphingomyelin.
• Lecithin is a significant constituent of brain and nervous tissue consisting of a mixture
of diglycerides of stearic, palmitic, and oleic acids, linked to the choline ester of
phosphoric acid.

09/13/2023
Lecithin 30
 Compound lipids
GLYCEROPHOSPHOLIPIDS:
• The hydrocarbon chains are hydrophobic . However, the charges on the phosphate and
amino groups make that portion of the molecule hydrophilic. The result is an
amphiphilic molecule.
• Amphiphilic lipids, in general, and phosphatidyl ethanolamine, in particular, are major
constituents of cell membranes. These molecules form a phospholipid bilayer with their
hydrophilic (polar) heads facing their aqueous surroundings (e.g., the cytosol) and their
hydrophobic tails facing each other.

09/13/2023 31
 Compound lipids
PROPERTIES OF GLYCEROPHOSPHOLIPIDS:
1. Glycerophospholipids are white waxy substances, which become dark when exposed to
air and light, owing to autoxidation and decomposition. This is due to the presence of
unsaturated fatty acids in the molecules.
2. They are soluble in alcohol and other fat solvents except in acetone.
3. They are hygroscopic and mix well with water to form cloudy, colloidal and slimy
solutions.
4. They do not have definite melting point and decompose when heated.
5. They are readily hydrolysed by boiling with acids and alkalies to their constituents.
6. They are hydrolysed by enzyme phospholipase to various components.

09/13/2023 32
 Compound lipids
Structure of GLYCEROPHOSPHOLIPIDS:
• Phospholipids are synthesized by esterification of an alcohol to the phosphate of
phosphatidic acid (1, 2-diacylglycerol 3-phosphate). Most phospholipids have a
saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone.
• The most commonly added alcohols (serine, ethanolamine and choline) also contain
nitrogen that may be positively charged, whereas, glycerol and inositol do not.

Phosphatidylcholine (PC) Phosphatidylethanolamine Phosphatidylserine (PS)

09/13/2023 33
(PE)
 Compound lipids
Structure of GLYCEROPHOSPHOLIPIDS:

Phosphatidylinositol (PI)

Diphosphatidylglycerol
09/13/2023 (DPG) 34
 Compound lipids
Role of Phospholipids in Cell membran:
• Different cells have different quantities of phospholipid in their membranes.
• Gray matter in the brain is nearly 70% phospholipid, whereas brain white matter is less than half
phospholipid.
• Brain gray matter is 30% phosphatidylcholine whereas brain white matter is 10%
phosphatidylcholine.
• The inner layer of neuron membranes primarily contain phosphatidylethanolamine &
phosphatidylserine, whereas in the outer layer phosphatidylcholine & sphingomyelin
predominate.
• Mitochondrial and endoplasmic reticulum membranes are both 40% phosphatidylcholine. But
mitochondrial membranes are also 35% phosphatidylethanolamine, whereas endoplasmic
reticulum membrane is about 17% phosphatidylethanolamine.
09/13/2023 35
 Compound lipids
Action of Phospholipases:
• Each of the 3 groups attached to the glycerol
backbone has a special enzyme that can separate the
group from the backbone.
• Phospholipase A1 enzyme attacks the attachment of
the first fatty acid.
• Phospholipase A2 attacks the attachment of the
middle fatty acid. Phospholipase D attacks the
alcohol attachment.
• Phospholipase C : which is a major toxin secreted by
bacteria -- releases 1, 2-DiAcylGlycerol (DAG) along
with a phosphoryl base.
09/13/2023 36
 Compound lipids
SPHINGOLIPIDS:
• After glycerophospholipids, the most abundant
lipids in plant and animal membranes are
sphingolipids. In mammals, sphingolipids are
particularly abundant in tissues of the central
nervous system.
• Most bacteria do not have sphingolipids.
• The structural backbone of sphingolipids is
sphingosine ,an unbranched alcohol with a
trans double bond between C-4 and C-5, an Sphingosine
amino group at C-2, and hydroxyl groups at C-1
and C-3.
09/13/2023 37
 Compound lipids
SPHINGOLIPIDS:
• Ceramide consists of a fatty acyl group linked to the
C-2 amino group of sphingosine by an amide bond.
• Ceramides are the metabolic precursors of all
sphingolipids.
• The three major families of sphingolipids are the
sphingomyelins, the cerebrosides, and the
gangliosides. Of these, only sphingomyelins contain
phosphate and are classified as phospholipids;
cerebrosides and gangliosides contain
carbohydrate residues and are classified as
glycosphingolipids.
Ceramide
09/13/2023 38
 Compound lipids
SPHINGOLIPIDS:
Sphingomyelins:
• In sphingomyelins, phosphocholine is attached to
the C-1 hydroxyl group of a ceramide.
• The sphingomyelins are synthesized by the transfer of
phosphorylcholine from phosphatidylcholine to a
ceramide in a reaction catalyzed by sphingomyelin
synthase.
• Sphingomyelins are present in the plasma
membranes of most mammalian cells and are a major sphingomyelins
component of the myelin sheaths that surround
certain nerve cells
09/13/2023 39
 Compound lipids
SPHINGOLIPIDS:
Cerebrosides:
• Cerebrosides are glycosphingolipids that contain one
monosaccharide residue attached by a linkage to C-1 of a
ceramide.
• Galactocerebrosides, also known as galactosylceramides, have
a single -D-galactosyl residue as a polar headgroup.
• Galactocerebrosides are abundant in nerve tissue and account
for about 15% of the lipids of myelin sheaths.
• Many other mammalian tissues contain glucocerebrosides,
ceramides with a -D-glucosyl head group. In some
glycosphingolipids, a linear chain of up to three more
monosaccharide residues is attached to the galactosyl or
glucosyl
09/13/2023 moiety of a cerebroside. 40
 Compound lipids
SPHINGOLIPIDS:
Gangliosides:
• Klenk, in 1942, isolated from beef brain.
• The highest concentrations are found in gray matter of brain. Gangliosides are the most complex of
the glycosphingolipids.
• Their molecular weights varies from 180,000 to 250,000.
• On hydrolysis, gangliosides yield the following:
• A long chain fatty acid usually C18 to C24.
• Alcohol – sphingosine
• A carbohydrate moiety which usually contains glucose or galactose, one molecule of N-acetyl galactosamine and
at least one molecule of N-acetyl neuraminic acid (NANA).
• Brain gangliosides are known to be complex and mono, di, trisialogangliosides containing 1 to 3 sialic
acid residues have been isolated.
09/13/2023 41
 Compound lipids
SPHINGOLIPIDS:
Gangliosides:
• The sugar units and sialic acid sections of the molecule are water soluble and negatively
charged, whereas the ceramide portion is lipid soluble.
• Deficiencies in lysosomal enzymes, which normally are responsible for the degradation of the
carbohydrate portions of various gangliosides, underlie the symptoms observed in rare
autosomally inherited diseases termed lipid storage diseases.

09/13/2023 42
 Compound lipids
SULFOLIPIDS:
• A glycolipid that contains sulfur is widely distributed in plants. It is localized in the
chloroplast but is also found in the chromatophores of photosynthetic bacteria.
• As the sulfur in this compound is present as a sulfonic group in a hexose, this may be
included under a class of compounds called sulfolipids.

09/13/2023 43
 FATTY ACIDS

09/13/2023 44
 FATTY ACIDS
Introduction:
• Fatty acids consist of the elements carbon (C), hydrogen (H) and oxygen (O) arranged as a carbon
chain skeleton with a carboxyl group (-COOH) at one end.
• A fatty acid may be defined as an organic acid that occurs in a natural triglyceride and is a
monocarboxylic acid ranging in chain length from C4 to about C30 carbon atoms.
• More than 100 different fatty acids have been identified in various species.
• Fatty acids differ from one another in the
• length of their hydrocarbon tails,
• the number of carbon–carbon double bonds,
• the positions of the double bonds in the chains, and
• the number of branches.
• Fatty acids usually do not occur in free or uncombined state in cells or tissues but are present in
covalently bound form in different classes of lipids.
• Fatty acids which occur in natural fats are usually monocarboxylic acid.
09/13/2023 45
 FATTY ACIDS
Introduction: The number of carbon atoms in the most abundant fatty acids
ranges from 12 to 20 and is almost always even since fatty acids are synthesized by the
sequential addition of two-carbon units.

09/13/2023 46
 FATTY ACIDS
Physical properties of fatty acids:
1. Fatty acids from butyric acid (C4) to caproic acid (C10) are liquid at ordinary tempreture while higher members above
C10 are solids.
2. The melting point increase with chain length.

3. Solubility in water decreases with chain length. Butyric acid is soluble in water in all proportions. Caproic acid is
moderately soluble in water.
4. The short chain fatty acids are steam volatile, the volatility decreases with chain length.

5. Most of fatty acids are soluble in hot alchole.

6. Variation in the position of the double bonds in unsaturated fatty acid chains produce isomers. Thus, Oliec acid could
have 15 different positional Isomers.
09/13/2023 47
 FATTY ACIDS
NOMENCLATURE:
• The systematic nomenclature of the fatty acids is based on the Genevan system.
• According to this system, The names of saturated fatty acids end with the suffix “-anoic” and
those of unsaturated acids with the suffix “-enoic”.
• Generally, the numbers are used with the International Union of Pure and Applied Chemistry
(IUPAC) system of nomenclature and the Greek letters when the common names are
employed.
• The position of carbon atoms in the fatty acid chain is indicated either by numbering in which
case the carboxyl carbon is numbered as C1, the carbon adjacent to C1 as C2 and so on or by the
use of Greek letters in which case carbon atom next to carboxyl group numbered as alpha and
next carbon beta and so on. The methyl carbon of fatty acid labeled as omega carbon.

09/13/2023 48
 FATTY ACIDS
NOMENCLATURE:
• In the case of unsaturated fatty acids for indicating double bond is to write number of carbon
atoms, the number of double bonds and the position of the double bonds below the name of the
acid.
• The position of a double bond is indicated by the lower number of the two carbon atoms involved
in double bonding. For example, oleic acid having 18 carbon atoms and a double bond between
carbon atoms 9 and 10 is written as 18:1; 9. Similarly linoleic acid with 18 carbon atoms, 2 double
bonds at C9 and C12 is written as 18:2;9,12.
• An alternative method to write the name of an unsaturated fatty acid is to write first the position
of double bonds in numerals and then the total number of carbon atoms in Roman followed by
the suffix “-enoic” acid. Thus, oleic acid may be written as 9-octadecenoic acid and Linoleic acid
as 9,12-octadecadienoic acid.

09/13/2023 49
 FATTY ACIDS
NOMENCLATURE:
• A shorthand notation for identifying fatty acids uses two numbers separated by a colon; the first refers
to the number of carbon atoms in the fatty acid, and the second refers to the number of carbon–carbon
double bonds, with their positions indicated as superscripts following a Greek symbol, Δ In this
notation, palmitate is written as 16:0, oleate as 18:1 Δ9 and arachidonate as 20:4 Δ 5,8,11,14
• Unsaturated fatty acids can also be described by the location of the last double bond in the
chain. This double bond is usually found three, six, or nine carbon atoms from the end of the chain.
Such fatty acids are called ω-3 (e.g., 18:3 Δ9,12,15), ω-6 (e.g., 18:2 Δ9,12), or ω-9 (e.g., 18:1 Δ9 ).

09/13/2023 50
 FATTY ACIDS

09/13/2023 51
 FATTY ACIDS
SATURATION:
Base on saturation,they are studied under two different
headings namely saturated and unsaturated fatty acids.
SATURATED FATTY ACIDS:
• The general formula for these acids is CnH2n+1COOH.
• When there is no double or triple bonds are present in the
fatty acids they are referred as saturated fatty acids. They
vary from C3 to C30.
• Saturated fatty acids having 10 carbons or less number of
carbon atoms are called as lower fatty acids e.g. acetic acid
and butyric acid. Milk contains significant amount of lower
fatty acids.
• Saturated fatty acids having more than 10 carbon atoms are
called higher fatty acids e.g. palmitic acid and stearic acid.
09/13/2023 52
 FATTY ACIDS
SATURATION:
UNSATURATED FATTY ACIDS:
• Fatty acids with only one double-bond are called mono-unsaturated. The general formula for
monounsaturated fatty acids is CnH2n-1COOH. For example: Oleic acid, Palmito oleic acid found in all
fats.
• Fatty acids with more than one double-bond are called poly-unsaturated (Polyethenoid) Fatty acid
(PUFA). Depending upon the double bonds their general formulae vary. For example:
• PUFA with two double bonds general formula is CnH2n-3COOH. Linoleic acid (18:2;9,12) occurs in many
seed oil, corn, peanut, cottonseed, soya bean oil.
• General formula for three double bond containing fatty acid is CnH2n-5COOH. Linolenic acid
(18:3;9,12,15)
• For fatty acids containing four double bonds CnH2n-7COOH. Arachidonic acid (20:4;5,8,11,14)
09/13/2023 53
 FATTY ACIDS
SATURATION:
UNSATURATED FATTY ACIDS:
• On account of the presence of double bonds, the unsaturated fatty acids exhibit geometric or cis-trans isomerism.
Most unsaturated fatty acids are found as the unstable cis isomer rather than as the more stable than trans isomer.

• Polyunsaturated fats have often been recommended to reduce coronary heart disease. But all saturated fats
do not have the same effect on cholesterol synthesis in the liver. Only the saturated fats of chain-length 12,
14 and 16 (lauric acid, myristic acid and palmitic acid) have been shown to elevate blood cholesterol.
• Polyunsaturated fatty acids can be a health hazard because carbon-carbon double bonds can lead to free-
radical formation and reactions with oxygen to form unstable lipid peroxide compounds containing the
same unstable oxygen-oxygen bond found in hydrogen peroxide. Lipid peroxidation and free radicals can
cause cancer and may accelerate aging.
09/13/2023 54
 FATTY ACIDS
SATURATION:
UNSATURATED FATTY ACIDS:
• Polyunsaturated "cis" fatty acids can be beneficial in cell membranes by preventing the tight packing of fatty
acids in membranes -- thereby making the membranes more "fluid". Membrane fluidity is important for
optimal function of most cells in the body.
• Most of the double-bonds made by biological systems have the cis configuration. It is the cis configuration of
unsaturated fatty acids that prevents tight packing of fatty acids in membranes, and hence increases
membrane fluidity.
• Saturated fats (like butter or lard) and fatty acids with trans double-bonds (like margarine) tend to be solids
at room temperature, whereas natural fatty acids with cis double-bonds (like vegetable oils) tend to be liquids.
• By artificially hydrogenating vegetable oils, the food processing industry reduces the number of double bonds
and causes the formation of trans fatty acids.
• when trans fatty acids are incorporated into cell membranes, the membrane fluidity is reduced and the cells
do not function as well.
09/13/2023 55
 FATTY ACIDS
NUMBER OF CARBON ATOMS:

Depending upon the number of carbon atoms, fatty acids generally classified into even number

and odd number fatty acids.

EVEN CHAIN FATTY ACIDS:

Fatty acids with even number carbon atoms are referred as even number fatty acids. Examples are

palmitic acid and stearic acid.

ODD CHAIN FATTY ACIDS:

If the number of carbon atoms in fatty acid is odd number then the fatty acids are refered as odd

chain fatty acids. Example: propionic acid and pentanoic acid.

09/13/2023 56
 FATTY ACIDS
 CHAIN NATURE:
 Depending upon the nature of carbon chain in fatty acids, they are classified as straight, branched, cyclic
and substituted fatty acids.
 STRAIGHT CHAIN FATTY ACIDS:
 If the carbon chain in fatty acids is straight chain then they are referred as straight chain fatty acids.
Example palmitic acid and stearic acid.
 BRANCHED CHAIN FATTY ACIDS:
 If the carbon chain in fatty acids is branched in nature then they are referred as branched chain fatty acids.
Example Isopalmitic acid in wool fat and phytanic acid in butter. Phytanic acid is 3, 7, 11, 15 tetramethyl
hexadecanoic acid.

09/13/2023 57
 CHAIN NATURE:
FATTY ACIDS
 SUBSTITUTED FATTY ACIDS:
 In hydroxy fatty acid and methyl fatty acid, one or more of the hydrogen atoms have been replaced by -OH
group or -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 oil.

 CYCLIC FATTY ACIDS:

 These are rare occurrence. Chaulmoogra oil, obtained from the plant Hydnocarpus kurzil and used in the
treatment of leprosy, contains two such acids hydnocarpic and chaulmoogric acids. They are named so
because they contain cyclic structure.

09/13/2023 58
09/13/2023 59
09/13/2023 60
Chemical Names and Descriptions of some Common Fatty Acids
Carbon Double
Common Name Scientific Name Sources
Atoms Bonds
Butyric acid 4 0 butanoic acid butterfat
Caproic Acid 6 0 hexanoic acid butterfat
Caprylic Acid 8 0 octanoic acid coconut oil
Capric Acid 10 0 decanoic acid coconut oil
Lauric Acid 12 0 dodecanoic acid coconut oil
Myristic Acid 14 0 tetradecanoic acid palm kernel oil
Palmitic Acid 16 0 hexadecanoic acid palm oil
Palmitoleic Acid 16 1 9-hexadecenoic acid animal fats
Stearic Acid 18 0 octadecanoic acid animal fats
Oleic Acid 18 1 9-octadecenoic acid olive oil
Vaccenic Acid 18 1 11-octadecenoic acid butterfat
Linoleic Acid 18 2 9,12-octadecadienoic acid safflower oil
61
Chemical Names and Descriptions of some Common Fatty Acids
Carbon Double Flaxseed (linseed)
Common Name Scientific Name
Atoms Bonds oil
Alpha-Linolenic Acid
18 3 9,12,15-octadecatrienoic acid borage oil
(ALA)
Gamma-Linolenic Peanut oil,
18 3 6,9,12-octadecatrienoic acid
Acid(GLA) fish oil
Arachidic Acid 20 0 eicosanoic acid fish oil
Gadoleic Acid 20 1 9-eicosenoic acid liver fats
Arachidonic Acid (AA) 20 4 5,8,11,14-eicosatetraenoic acid fish oil
EPA 20 5 5,8,11,14,17-eicosapentaenoicacid rapeseed oil
Behenic acid 22 0 docosanoic acid rapeseed oil
Erucic acid 22 1 13-docosenoic acid fish oil
small amounts
DHA 22 6 4,7,10,13,16,19 docosahexaenoicacid
in most fats
Flaxseed (linseed)
Lignoceric acid 24 0 tetracosanoic acid
oil

09/13/2023 62
 FATTY ACIDS
Essential Fatty Acids (EFA):

The fatty acids that cannot be synthesized by the body and therefore should be supplied

in the diet are known as essential fatty acids. Chemically they are polyunsaturated fatty

acids (PUFA), namely linoleic acid, linolenic acid and arachidonic acid.

Structure CH3 (CH2)4 CH = CH-CH2-CH=CH(CH2)7 COOH Linoleic acid

CH3 (CH2)4 CH = CH-CH2-CH=CH -CH2-CH = CH(CH2)7 COOH Linolenic acid

CH3 (CH2)4 CH = CH-CH2-CH=CH -CH2-CH = CH-CH2-CH=CH- (CH2)3 COOH

09/13/2023 63
 FATTY ACIDS
Functions of EFA:

1. EFAs are required for the membrane structure and functions.

2. They are necessary for the maintenance of growth, reproduction and good health.

3. They are important for the transport of cholesterol, formation of lipoprotein and prevention of fatty liver.

4. They serve as precursor for prostaglandin biosynthesis.

5. They prolong clotting time and increase fibrinolytic activity.

09/13/2023 64
 Steroids

09/13/2023 65
 Steroid
Introduction:
• Steroids are a third class of lipids found in the membranes of eukaryotes and, very rarely, in
bacteria.
• Steroids contain four fused rings: three six-carbon rings designated A, B, and C and a five
carbon D ring. They whole rign system conined as cyclopentanoperhydro phenanthrene
(CPPP).
• steroids differ in the length of the side chain attached to C-17 and in the number and
placement of methyl groups, double bonds, hydroxyl groups, and in some cases, keto groups.
• The characteristic ring structure is derived from squalene.
09/13/2023 66
09/13/2023 67
 Steroid
Animal Sterol (Cholesterol):
• Cholesterol has been found in animal tissues and rarely found in plants and
never in prokaryotes and fungi.
• The highest concentration of cholesterol occurs in brain and nervous tissues,
adrenal cortex, corpus luteum, testes and egg yolk. Moderate amounts of
cholesterol are present in liver, kidney, spleen and skin.
• Cholesterol is synthesized by mammalian cells. It is not only a component of
certain membranes but also an essential precursor of steroid hormones and bile
salts.
Structure:
• C27H46O, Cholesterol has a steroid ring system consisting of 19 carbon atoms
and a side chain hydrocarbon consisting of 8 carbon atoms.
• It has a double bond at carbon 5-6 and a secondary alcoholic hydroxyl group
attached to C3.
• The C10 and C13 carry two methyl groups which are numbered respectively as C19
and C18
09/13/2023 68
• The side chain is attached to C17.
 Steroid
Animal Sterol (Cholesterol):
Properties:
 Cholesterol first isolated from bile in 1784, Cholesterol is insoluble in water but soluble in solvents such
as chloroform, ether, benzene and hot alcohol.
 It is tasteless and odorless, solid at room temperature and melts at 150C.
 Cholesterol has several asymmetric carbon atoms, about 512 stereoisomers are possible.
 The chemical properties of cholesterol are particularly related to secondary hydroxyl group and the
double bond present in the molecule.
 It gives addition reactions such as hydrogenation and halogenation because of the presence of double
bond.
 It is one of the essential constituents of cells and influences the permeability functions of the cell.
 It assists the formation of bile acids and bile salts, 7- dehydrocholesterol, vitamin D3, corticosteroid
hormones, androgens, estrogens and progesterone.
 It controls the redcells from being easily hemolyzed and It performs defensive action.
09/13/2023 69
 Steroid
7-Dehydrocholesterol:
• This sterol occurs in many tissues but that which is present in the skin has a special role.
• It is converted to vitamin D3, i.e. cholecalciferol when the skin is exposed to ultraviolet rays.
• Exposure to sunlight also results in the formation of Vit D3 in the skin because sunlight
contains some U.V rays; for this reason, vitamin D3 is also called sunlight vitamin.
Ergosterol:
• Ergosterol occur in plants. It is also found in yeast and fungi as the structural constituent
of membranes and first isolated from ergot.
• It is an important precursor for vitamin-D. When exposed to light, it is converted to
ergocaliciferol, a compound containing vitamin-D activity.
• Its structure is similar to that of cholesterol, but differs in 1. It has another double bond at
C7-C8. 2. It has a double bond in the side chain. 3. It has an additional CH3 group in the
side chain.

09/13/2023 70