LIPID CHEMISTRY

The lipids are a heterogeneous group of

compounds, including fats, oils, steroids, waxes,
and related compounds, that are related more by
their physical than by their chemical properties.

They have the common property of being

(1) relatively insoluble in water

(2) soluble in nonpolar solvents such as ether and

chloroform.
(3) In contrast to other biomolecules like
polysaccharides,proteins and nucleic acids they do not
form polymers.
lipids are a group of naturally occuring
molecules that include fats, waxes ,sterols, fat-
soluble vitamins (such as vitamins A, D, E, and K), 
monoglycerides,diglycerides, triglycerides
, phospholipids, and others
.
Although the term lipid is sometimes used as a
synonym for fats, fats are a subgroup of lipids called 
triglycerides
 • Biological importance of lipids

 Lipids (in the form of fats) form an important component of our

diet. Also, food is stored in our body in the form of fats (which are
lipids). Fats provide slow and long lasting energy.  They have a high-
energy value (25% of body needs) and they provide more energy
per gram than carbohydrates and proteins
. 
Lipids as phospho-lipids are found in plasma membranes and other
organelle membranes of all the cells. 
Lipids as lipoprotein are important cellular constituent of both
cellular and sub cellular membranes.

. Vitamin A, D, E and K are derived lipids. 

Spingolipids are found in myelin sheath of Nerve cells. 
Glycolipids are found in grey matter and white matter of the
brain. 

. Prostaglandin a derived lipid helps in induction of labour

pain for normal birth of child. They also cause broncho
dialation and decreases secretion of HCL in stomach. It is used
for treating asthma. 

. Cholesterol a steroid lipid helps in the synthesis of Vitamin

D. Cholesterol forms hormones like testosterone, estrogen,
progestrone, cortisone, aldosterone, cortisol. It also prevents
breakdown of plasma membrane and also percentage
breakdown of RBC's
lipids are required as essential fatty acids
that cannot be synthesized by the body
Wax which is a Lipid is of various types:
 
---> Cerumen (Ear wax): It is found in the human
ear to protect the entry of bacteria and insects
and also to amplify sound. 
---> Lanolin (Wool Wax): It is found in the wool
of animals to protect them against the ravages
of climate and the environment
--> Beewax is produced by bees and it us used
for making candles. 
-Stored lipids “depot fat” is stored in all human cells
acts as:
A store of energy.
A pad for the internal organs to protect them from
outside shocks.
A subcutaneous thermal insulator against loss of
body heat.
Lipids provide bases for dealing with diseases such
as obesity, atherosclerosis, lipid-storage
diseases, essential fatty acid deficiency,
respiratory distress syndrome,
Classification of Lipids

1. Simple lipids (Fats &

Waxes)
2. Compound or conjugated
lipids
3. Derived Lipids
4. Lipid-associating
substance
Simple lipids: Esters of fatty acids with various
alcohols.

a. Fats: Esters of fatty acids with glycerol. Oils are fats in

the liquid state. Most of dietary lipids are fats and
oils (triglycerides and triacylglycerols) - These are esters
of fatty acids with a trihydroxy alcohol, glycerol. A fat is
solid at ordinary room temperature, an oil is liquid.

b. Waxes: Esters of fatty acids with higher molecular

weight monohydric alcohols.
   
1-Simple Lipids
A-Neutral Fats and oils (Triglycerides)

Definition:
- They are called neutral because they are uncharged due to
absence of ionizable groups in it.
The neutral fats are the most abundant lipids in nature.
They constitute about 98% of the lipids of adipose tissue,
30% of plasma or liver lipids, less than 10% of erythrocyte
lipids.
Triglycerides These are formed by esterification
of three molecules of fatty acids with one molecule of
trihydric alcohol, glycerol.
If the number of fatty acids attached to a glycerol
happens to be two, the ester is called diglyceride

If there is only one molecule of fatty acid attached to a

glycerol molecule it is monoglyceride.

In mammals, triglycerides are found in the cytoplasm of

adipose cells which are specialized for the synthesis and
storage of triglycerides.
Triglycerides lack any free polar group because polar
OH group of glycerol and carboxyl
Group of FA are involved in ester linkage.
This gives TG a complete non polar characteristics.
2. Complex lipids(COMPOUND LIPIDS):
Esters of fatty acids containing groups in addition to an alcohol
and a fatty acid. additional groups are—phosphate group,
nitrogenous base,carbohydrate,proteins etc.

 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
Depending on type of alcohol,further subdivided into 2 groups
glycerophospholipids the alcohol is glycerol .

LECITHIN(phosphatidyl choline)
Cephalin(phosphatidyl ethanolamine)

and in sphingophospholipids the alcohol is sphingosine.

b. Glycolipids (glycosphingolipids): Lipids containing
a fatty acid, sphingosine, and carbohydrate. No
phosphoric acid and glycerol.

These are of 2 types

Cerebrosides
Gangliosides

Lipoprotiens contain protein group complexed with

lipid molecule.
Help in transport of lipids.

c. Other complex lipids: Lipids such as sulfolipids

and aminolipids.
Derived lipids: These
include-
 fatty acids
glycerol
steroids
other alcohols
fatty aldehyde
 ketone bodies
hydrocarbons, lipid-soluble
vitamins, and hormones.
GLYCEROLIt is a trihydric alcohol (i.e., containing
three OH groups) and has the popular name glycerin.
It is synthesized in the body from glucose.

Colorless viscous oily liquid with sweet taste.

-It has a nutritive value by conversion into glucose

and enters in structure of phospholipids.
 USES OF GLYCEROL
1. Reduces brain edema in cerebrovascular disease.

2. Nitroglycerin is used as vasodilator especially for the

coronary arteries, thus it is used in treatment of
angina pectoris. Also, enters in explosives
manufacturing.
3. Glycerol is used in treatment of glaucoma (increased
intraocular pressure)due to its ability to dehydrate
the tissue from its water content.
4. Many pharmaceutical and cosmetic preparations
have glycerol in their formulas. It has many uses in
laboratory.
 Fatty Acids

Definition:

Fatty acids are aliphatic mono-carboxylic acids that

are mostly obtained from the hydrolysis of natural
fats and oils.
Have the general formula R-(CH2)n-COOH and mostly
have straight chain (a few exceptions have branched
and heterocyclic chains). In this formula "n" is
mostly an even number of carbon atoms (2-34) with
a few exceptions that have an odd number.

Fatty acids are classified according to several bases

as follows:
2)Classification of fatty acids based on
length of hydrophobic chain
Short chain-with 2-6 carbon atoms
Medium chain- with 8-14 carbon atoms
Long chain- with 16-18 carbon atoms
Very long chain fatty acids- with 20 or more carbon
atoms
Fatty acids can be classified in many ways-
1) According to nature of the hydrophobic
chain-
a) Saturated
b) Unsaturated
c) Branched chain fatty acids
d) Substituted Fatty acids
Saturated fatty acids do not contain double bonds,
while unsaturated fatty acids contain double bonds
I. According to presence or absence of double
bonds they are classified into:

A-Saturated Fatty Acids

they contain no double bonds with 2-24 or more
carbons.
They are solid at room temperature except if
they are short chained.
They may be even or odd numbered.
They have the following molecular formula,
CnH2n+1COOH.
 The 16- and 18-carbon fatty acids are most
common.
The hydrocarbon chain is almost invariably
unbranched in animal fatty acids. A few
branched-chain fatty acids have also been
isolated from both plant and animal sources.
Number of C Common Name Systemic Name Formula
atoms
2 Acetic acid Ethanoic acid CH3COOH
4 Butyric acid Butanoic acid CH3(CH2)2COOH
6 Caproic acid Hexanoic acid CH3(CH2)4COOH

8 Caprylic acid Octanoic acid CH3(CH2)6COOH

10 Capric acid Decanoic acid CH3(CH2)8COOH

12 Lauric acid Dodecanoic acid CH3(CH2)10COOH
14 Myristic acid Tetradecanoic acid CH3(CH2)12COOH

16 Palmitic acid Hexadecanoic acid CH3(CH2)14COOH

18 Stearic acid Octadecanoic acid CH3(CH2)16COOH

20 Arachidic acid Eicosanoic acid CH3(CH2)18COOH

22 Behenic acid Docosanoic acid CH3(CH2)20COOH
Source: vegetable oils such as corn oil, linseed
oil, peanut oil, olive oil, cottonseed oil,
soybean oil and many other plant oils, cod
liver oil and animal fats.
Deficiency: Their deficiency in the diet leads
to nutrition deficiency disease.
Its symptoms include: poor growth and health
with susceptibility to infections, dermatitis,
decreased capacity to reproduce, impaired
transport of lipids, fatty liver, and lowered
resistance to stress.
B-Unsaturated Fatty Acids
They contain double bond
monounsaturated (MUFA)
they contain one double bond.
(CnH2n-1 COOH)
polyunsaturated (PUFA)
they contain more the one double bond (CnH2n-
more than 1 COOH).
1-Monounsaturated fatty acids:
1-Palmitoleic acid :
It is found in all fats.
It is C16:1∆9, i.e., has 16 carbons and one double bond
located at carbon number 9 and involving carbon 10.

CH3-( CH2 )5CH = CH-(CH2)7 –COOH

2-Oleic acid
Is the most common fatty acid in natural fats.
It is C18:1∆9, i.e., has 18 carbons and one double
bond located at carbon number 9 and involving
carbon 10.

CH3-(CH2)7- CH=CH – (CH2)7-COOH

2-Polyunsaturated fatty acids :
(Essential fatty acids):
Definition:
They are essential fatty acids that can not be
synthesized in the human body and must be
taken in adequate amounts in the diet.
They are required for normal growth and
metabolism
1-Linoleic acid:
C18:29, 12.
It is the most important since other essential
fatty acids can be synthesized from it in the
body.

CH3-(CH2)4-CH = CH-CH2-CH=CH-(CH2)7-COOH
-Linolenic acid:
C18:39, 12, 15,
in corn, linseed, peanut, olive, cottonseed and
soybean oils.

CH3-CH2-CH=CH-CH2-CH=CH-CH2-CH=CH-
(CH2)7-COOH
3-Arachidonic acid:
C20:45, 8, 11, 14.
It is an important component of
phospholipids in animal and in peanut oil
from which prostaglandins are synthesized.

CH3-(CH2)4-CH=CH-CH2-CH=CH-CH2-CH=CH-
CH2-CH=CH-(CH2)3- COOH
Because of the kinks in the hydrocarbon tails, unsaturated fats
can’t pack as closely together, making them liquid at room
temperature.

The membrane lipids, which must be fluid at all environmental

temperatures, are more unsaturated than storage lipids.
Lipids in tissues that are subject to cooling, eg, in hibernators or in
the extremities of animals, are more unsaturated.
At higher temperatures, some bonds rotate, causing chain
shortening, which explains why biomembranes become thinner
with increases in temperature.

The carbon chains of saturated fatty acids form a zigzag pattern

when extended, as at low temperatures.
Function of Essential Fatty Acids:
1. They are useful in the treatment of atherosclerosis
by help transporting blood cholesterol and lowering
it and transporting triglycerides.
2. The hormones are synthesized from them.
3. They enter in structure of all cellular and subcellular
membranes and the transporting plasma
phospholipids.
4. They are essential for skin integrity, normal growth
and reproduction.
5. They have an important role in blood clotting
(intrinsic factor).
6. Important in preventing and treating fatty liver.
7. Important role in health of the retina and vision.
8. They can be oxidized for energy production
 Nomenclature of Fatty acids

The systematic name for a fatty acid is derived from the

name of its parent hydrocarbon by the substitution of oic
for the final e.
For example, the C18 saturated fatty acid is called
octadecanoic acid because the parent hydrocarbon is
octadecane.
A C18 fatty acid with one double bond is called
octadecenoic acid; with two double bonds, octadecadienoic
acid; and with three double bonds, octadecatrienoic acid.
The notation 18:0 denotes a C18 fatty acid with no
double bonds, whereas 18:2 signifies that there are two
double bonds.
Carbon atoms are numbered from the carboxyl carbon
(carbon No. 1).
The carbon atoms adjacent to the carboxyl carbon (Nos. 2, 3,
and 4) are also known as the α ,β , and carbons, respectively,
and the terminal methyl carbon is known as theω or n-
carbon. The position of a double bond is represented by the
symbol ∆followed by a superscript number.
eg, ∆ 9 indicates a double bond between carbons 9 and 10 of
the fatty acid
Alternatively, the position of a double bond
can be denoted by counting from the distal
end, with the ω-carbon atom (the methyl
carbon) as number 1.
ω9 indicates a double bond on the ninth
carbon counting from the ω-carbon.

In animals, additional double bonds are

introduced only between the existing double
bond (eg, 9, 6, or 3) and the carboxyl carbon,
leading to three series of fatty acids known as
the ω9, ω6, and ω3 families, respectively.
Omega 3 and Omega 6 fatty acids
Trans fatty acids are present in certain foods,
arising as a by-product of the saturation of fatty acids
during hydrogenation, or "hardening," of natural oils in
the manufacture of margarine.
An additional small contribution comes from the
ingestion of ruminant fat that contains trans fatty acids
arising from the action of microorganisms in the rumen.
Naturally-occurring unsaturated vegetable oils have
almost all cis bonds, but using oil for frying causes some
of the cis bonds to convert to trans bonds.
 brached chain
fatty acid ; Phytanic acid present in butter
Sebum also contains branched chain fatty acids

There may be even or odd chain fatty acids.

Even chain fatty acids are predominantly present.
d) Cyclic fatty acids-
 Chaulmoogric acid and Hydnocarpic acid
e) Substituted fatty acids
 Cerebronic acid- OH fatty acid
S.No. Number of C Family Common Systemic Name
atoms, Name
number and
location of
double bonds

[c] Trienoic acids

(three double
bonds) 

1. 18:3;6,9,12 ω6 Y- Linolenic all-cis-6,9,12-

acid Octadecatrien
oic 

2. 18:3;9,12,15 ω3 α-Linolenic all-cis-

9,12,15Octade
catrienoic 
 2-Compound Lipids
Definition:
They are lipids that contain additional substances, e.g.,
sulfur, phosphorus, amino group, carbohydrate, or
proteins beside fatty acid and alcohol.
Compound or conjugated lipids are classified into the
following types according to the nature of the additional
group:
1. Phospholipids
2. Glycolipids.
3. Lipoproteins
4. Sulfolipids and amino lipids.
a)Phospholipids-
Contain in addition to fatty acids
and glycerol/or other alcohol, a
phosphoric acid residue, nitrogen
containing base and other
substituents.
Phospholipids may be regarded
as derivatives of phosphatidic
acid , in which the phosphate is
esterified with the —OH of a
suitable alcohol.
They are amphipathic molecules
containing a polar head and a
hydrophobic portion
2TYPES OF PHOSPHOLIPIDS
Based on nature of alcohol-
1)Glycerophospholipids- Glycerol is the alcohol group.
Examples-
o Phosphatidyl choline
o Cardiolipin
o Plasmalogen
o Platelet activating factor
o Phosphatidyl Glycerol
o Phosphatidyl ethanolamine
o Phosphatidyl serine
o Phosphatidyl inositol
o Phosphatidic acid
2)Sphingophospholipids- Sphingol is the alcohol group
Example- Sphingomyelin
1) Phosphatidylcholines (Lecithins )
Phosphoacylglycerols containing choline are the
most abundant phospholipids of the cell membrane
 Are present a large proportion of the body's store
of choline. Choline is important in nervous
transmission, as acetylcholine, and as a store of
labile methyl groups
Dipalmitoyl lecithin is a very effective surface-active
agent and a major constituent of the surfactant
preventing adherence, due to surface tension, of the
inner surfaces of the lungs. Its absence from the lungs of
premature infants causes respiratory distress syndrome.
5) Cardiolipin –
Abundantly found in mitochondrial membrane.
This is the only phospholipid with antigenic properties.

6) Plasmalogens –
constitute as much as 10% of the phospholipids of brain and
muscle.
Structurally, the plasmalogens resemble
phosphatidylethanolamine but possess an ether link on the
sn-1 carbon instead of the ester link found in acylglycerols.
Typically, the alkyl radical is an unsaturated alcohol .
In some instances, choline, serine, or inositol may be
substituted for ethanolamine
7) Platelet activating factor (PAF)-

Ether glycerophospholipid
Contains an unsaturated alkyl group in an ether link to
carbon -1
An acetyl residue at carbon 2 of the glycerol backbone.
Synthesized and released by various cell types
PAF activates inflammatory cells and mediates
hypersensitivity, acute inflammatory and anaphylactic
reactions
Causes platelets to aggregate and degranulate and
neutrophils and alveolar macrophages to generate
superoxide radicals
8) Phosphatidyl Glycerol-
Formed by esterification of
phosphatidic acid with
glycerol
Diphosphatidyl glycerol,
cardiolipin is found in the
mitochondrial membrane
 2)Sphingophospholipids

SPHINGOMYELIN Backbone is sphingosine ( Amino

alcohol) A long chain fatty acid is attached to amino
group of sphingosine to form Ceramide
The alcohol group at carbon-1of sphingosine is
esterified to phosphoryl choline, producing
sphingomyelin
Sphingomyelin is an important component of myelin
of nerve fibers
 Functions of Phospholipids

Components of cell membrane,

mitochondrial membrane and lipoproteins
Participate in lipid absorption and
transportation from intestine
Play important role in blood coagulation
 Required for enzyme action- especially in
mitochondrial electron transport chain
Choline acts as a lipotropic agent
Membrane phospholipids acts as source of
Arachidonic acid
Act as reservoir of second messenger- Phosphatidyl
Inositol
Act as cofactor for the activity of Lipoprotein lipase
Phospholipids of myelin sheath provide insulation
around the nerve fobers
Dipalmitoyl lecithin acts as a surfactant
 B-Glycolipids
Definition: They are lipids that contain carbohydrate
residues with sphingosine as the alcohol and a very
long-chain fatty acid (24 carbon series).
They are present in cerebral tissue, therefore are called
cerebrosides
Classification: According to the number and nature of
the carbohydrate residue(s) present in the glycolipids
the following are
1. Cerebrosides. They have one galactose molecule
(galactosides).
2. Sulfatides. They are cerebrosides with sulfate on
the sugar (sulfated cerebrosides).
3. Gangliosides. They have several sugar and
sugaramine residues.
 Ceramide

Sphingosine
Fatty acid
OH O
CH3 (CH2)12 CH CH CH CH NH C R1
CH2

CH2OH O
OH O
H
Galactose
OH H
H H

H OH

Psychosin
Cerebroside
1-Cerebrosides:
Occurrence: They occur in myelin sheath of
nerves and white matter of the brain tissues
and cellular membranes. They are important
for nerve conductance.
Structure: They contain sugar, usually -
galactose and may be glucose or lactose,
sphingosine and fatty acid, but no phosphoric
acid.
3-Gangliosides:
They are more complex glycolipids that occur in the
gray matter of the brain, ganglion cells, and RBCs.
They transfer biogenic amines across the cell
membrane and act as a cell membrane receptor.
 C-Lipoproteins
Definition: Lipoproteins are lipids combined with
proteins in the tissues. The lipid component is
phospholipid, cholesterol or triglycerides. The
holding bonds are secondary bonds.
They include:
1. Structural lipoproteins: These are widely
distributed in tissues being present in cellular
and subcellular membranes. In lung tissues
acting as a surfactant in a complex of a protein
and lecithin. In the eye, rhodopsin of rods is a
lipoprotein complex.
Transport lipoproteins:
These are the forms present in blood plasma.
They are composed of a protein called apolipoprotein
and different types of lipids. (Cholesterol, cholesterol
esters, phospholipids and triglycerides). As the lipid
content increases, the density of plasma lipoproteins
decreases
a) Chylomicrons:
They have the largest diameter and the least
density. They contain 1-2% protein only and 98-
99% fat. The main lipid fraction is triglycerides
absorbed from the intestine and they contain
small amounts of the absorbed cholesterol and
phospholipids.
b) Very low-density lipoproteins (VLDL) or pre--
lipoproteins: Their diameter is smaller than chylomicrons.
They contain about 7-10% protein and 90-93% lipid. The
lipid content is mainly triglycerides formed in the liver. They
contain phospholipid and cholesterol more than
chylomicrons.

c) Low-density lipoproteins (LDL) or -lipoproteins:

They contain 10-20% proteins in the form of apolipoprotein
B. Their lipid content varies from 80-90%. They contain
about 60% of total blood cholesterol and 40% of total blood
phospholipids. As their percentage increases, the liability to
atherosclerosis increases.
d) High-density lipoproteins (HDL) or -Lipoproteins:
They contain 35-55% proteins in the form of
apolipoprotein A. They contain 45-65% lipids formed of
cholesterol (40% of total blood content) and
phospholipids (60% of total blood content). They act as
cholesterol scavengers, as their percentage increases, the
liability to atherosclerosis decreases. They are higher in
females than in males. Due to their high protein content
they possess the highest density.

e) Albumin-free fatty acids complex: It is a proteolipid

complex with 99% protein content associated with long-
chain free fatty acids for transporting them.
Cholesterol:
Importance: -
It is the most important sterol in animal tissues as free
alcohol or in an esterified form (with linoleic, oleic,
palmitic acids or other fatty acids).
Steroid hormones, bile salts and vitamin D are
derivatives from it.
Tissues contain different amounts of it that serve a
structural and metabolic role, e.g., adrenal cortex
content is 10%, whereas, brain is 2%, others 0.2-0.3%.
Source: - It is synthesized in the body from
acetyl-CoA (1gm/day, cholesterol does not
exist in plants) and is also taken in the diet (0.3
gm/day as in, butter, milk, egg yolk, brain,
meat and animal fat
Most important sterol in human
body
CHOLESTEROL
 Molecular formula-C27H45 OH
Possesses a cyclo pentano
perhydrophenatherene ring
nucleus
Has an -OH group at C3
 A double bond between C5 and
C6
 Two- CH3 groups at C10 and
C13
An eight carbon side chain
attached to C17
Cholesterol occurs both as free form or in ester form

 In cholesteryl ester, the hydroxyl group on position 3 is

esterified with a long-chain fatty acid.

Cholesterol esters are formed by the transfer of acyl group

by Acyl transferases-(LCAT and ACAT)

In plasma, both forms are transported in lipoproteins

 Plasma low-density lipoprotein (LDL) is the vehicle of
uptake of cholesterol and cholesteryl ester into many
tissues.

Free cholesterol is removed from tissues by plasma high-

density lipoprotein (HDL) and transported to the liver, where
it is eliminated from the body either unchanged or after
conversion to bile acids in the process known as reverse
cholesterol transport

A sum total of free and ester cholesterol in serum is called

serum total cholesterol
 Significance of Cholesterol

Cholesterol is widely distributed in all cells of the body but

particularly in nervous tissue.
It is a major constituent of the plasma membrane and of
plasma lipoproteins.
It is synthesized in many tissues from acetyl-CoA and is the
precursor of all other steroids in the body, including
corticosteroids, sex hormones, bile acids, and vitamin D.
Cholesterol is a major constituent of gallstones.
Its chief role in pathologic processes is as a factor in the
genesis of atherosclerosis of vital arteries, causing
cerebrovascular, coronary, and peripheral vascular disease.
Other sterols of biological Importance

7- dehydrocholesterol- also called as Provitamin D3

(Precursor of vitamin D)
Ergo sterol-plant sterol (First isolated from Ergot-
Fungus of Rye)
Stigmasterol and Sitosterol- Plant sterols
Coprosterol (Coprostanol)- Reduced products of
cholesterol- found in feces
Other steroids- Bile acids, adrenocortical
hormones, gonadal hormones, D vitamins and
Cardiac glycosides.
 Normal serum level and Variations
Normal level of serum total cholesterol ranges between
150-220 mg/dL
 Physiological variations-
Low at the time of birth, increases with advancing age.
The level is increased during pregnancy
Pathological Variations-
a) Low cholesterol (Hypocholesterolemia)-
Thyrotoxicosis, anemia, hemolytic jaundice, wasting
diseases and malabsorption syndrome.
B) Hypercholesterolemia-
 Nephrotic syndrome
Diabetes Mellitus
Obstructive Jaundice
Myxoedema
Xanthomatous biliary
cirrhosis
Hypopituitarism
Familial
Hypercholesterolemia
Idiopathic
AMPHIPATHIC LIPIDS
Fatty acids, phospholipids, sphingolipids, bile salts, and, to
a lesser extent, cholesterol contain polar groups.
Therefore, part of the molecule is hydrophobic, or water-
insoluble; and part is hydrophilic, or water-soluble. Such
molecules are described as amphipathic
They become oriented at oil:water interfaces with the
polar group in the water phase and the nonpolar group in
the oil phase.
A bilayer of such amphipathic lipids is the basic structure
in biologic membranes
Liposomes-Liposomes may be formed by sonicating an
amphipathic lipid in an aqueous medium.
They consist of spheres of lipid bilayers that enclose part of
the aqueous medium.
Liposomes are of potential clinical use—particularly when
combined with tissue-specific antibodies—as carriers of
drugs in the circulation, targeted to specific organs, eg, in
cancer therapy.
In addition, they are used for gene transfer into vascular
cells and as carriers for topical and transdermal delivery of
drugs and cosmetics.
Chemical Properties of fats and oils:
1-Hydrolysis:
They are hydrolyzed into their constituents
(fatty acids and glycerol) by the action of
super heated steam, acid, alkali or enzyme
(e.g., lipase of pancreas).
- During their enzymatic and acid hydrolysis
glycerol and free fatty acids are produced.
 O O
CH2 O C R1 H2C OH R1 C OH
O Lipase or Acid O
R2 C O C H HO C H + R C OH
2
O
O
CH2 O C R3 3 H2O H2C OH
R3 C OH
Triacylglycerol Glycerol Free fatty acids
 2-Saponification. Alkaline hydrolysis produces
glycerol and salts of fatty acids (soaps).
Soaps cause emulsification of oily material
this help easy washing of the fatty materials

O O
CH2 O C R1 H2C OH R1 C ONa
O O
R2 C O C H HO C H + R C ONa
2
O
O
CH2 O C R3 3 NaOH H2C OH
R3 C ONa
Triacylglycerol Glycerol Sodium salts of
fatty acids (soap)
3-Halogenation
Neutral fats containing unsaturated fatty acids
have the ability of adding halogens (e.g.,
hydrogen or hydrogenation and iodine or
iodination) at the double bonds.
- It is a very important property to determine
the degree of unsaturation of the fat or oil
that determines its biological value
4-Hydrogenation or hardening of oils:
It is a type of addition reactions accepting
hydrogen at the double bonds of unsaturated
fatty acids.
The hydrogenation is done under high
pressure of hydrogen and is catalyzed by
finely divided nickel or copper and heat.
It is the base of hardening of oils (margarine
manufacturing), e.g., change of oleic acid of
fats (liquid) into stearic acid (solid).
It is advisable not to saturate all double
bonds; otherwise margarine produced will be
very hard, of very low biological value and
difficult to digest.
 Oils Hydrogen, high pressure, nickel Hard fat
(liquid) (margarine, solid)
(with unsaturated (with saturated
fatty acids, e.g., oleic) fatty acids, e.g., stearic)

Advantages for hydrogenated oil or fat are as

follows:
1. It is more pleasant as cooking fat.
2. It is digestible and utilizable as normal
animal fats and oils.
3. It is less liable to cause gastric or
intestinal irritation.
4. It is easily stored and transported and
less liable to rancidity.
Disadvantages of hydrogenated
fats include lack of fat-soluble vitamins (A, D,
E and K) and essential fatty acids
5-Oxidation(Rancidty)
This toxic reaction of triglycerides leads to
unpleasant odour or taste of oils and fats
developing after oxidation by oxygen of air,
bacteria, or moisture.
Also this is the base of the drying oils after
exposure to atmospheric oxygen.
Example is linseed oil, which is used in
paints and varnishes manufacturing
 Rancidity
Definition:
It is a physico-chemical change in the natural
properties of the fat leading to the
development of unpleasant odor or taste or
abnormal color particularly on aging after
exposure to atmospheric oxygen, light,
moisture, bacterial or fungal contamination
and/or heat.
Saturated fats resist rancidity more than
unsaturated fats that have unsaturated
double bonds
Types and causes of Rancidity:
1. Hydrolytic rancidity
2. Oxidative rancidity
3. Ketonic rancidity
1-Hydrolytic rancidity:
It results from slight hydrolysis of the fat by
lipase from bacterial contamination
leading to the liberation of free fatty
acids and glycerol at high temperature
and moisture.
Volatile short-chain fatty acids have
unpleasant odor.
 O O
CH2 O C R1 H2C OH R1 C OH
O
Lipase O
R2 C O C H HO C H + R C OH
2
O
O
CH2 O C R3 3 H2O H2C OH
R3 C OH
Triacylglycerol Glycerol Free fatty acids
(volatile, bad odor)
2-Oxidative Rancidity:
It is oxidation of fat or oil catalyzed by
exposure to oxygen, light and/or heat
producing peroxide derivatives which on
decomposition give substances, e.g.,
peroxides, aldehydes, ketones and
dicarboxylic acids that are toxic and have bad
odor.
This occurs due to oxidative addition of
oxygen at the unsaturated double bond of
unsaturated fatty acid of oils.
 Polyunsaturated fatty acid
Oxidant, O2

Peroxyradical

Cyclic peroxide Hydroperoxide

Aldehydes Hydroxy fatty acid

such as malondialdehyde
Other fragments
such as dicarboxylic acids
3-Ketonic Rancidity:
It is due to the contamination with certain
fungi such as Asperigillus Niger on fats such as
coconut oil.
Ketones, fatty aldehydes, short chain fatty
acids and fatty alcohols are formed.
Moisture accelerates ketonic rancidity.
Prevention of rancidity is achieved by:
1. Avoidance of the causes (exposure to
light, oxygen, moisture, high
temperature and bacteria or fungal
contamination). By keeping fats or oils in
well-closed containers in cold, dark and
dry place (i.e., good storage conditions).
2. Removal of catalysts such as lead and
copper that catalyze rancidity.
3. Addition of anti-oxidants to prevent
peroxidation in fat (i.e., rancidity). They
include phenols, naphthols, tannins and
hydroquinones. The most common
natural antioxidant is vitamin E that is
important in vitro and in vivo.
Hazards of Rancid Fats:
1. The products of rancidity are toxic, i.e.,
causes food poisoning and cancer.
2. Rancidity destroys the fat-soluble
vitamins (vitamins A, D, K and E).
3. Rancidity destroys the polyunsaturated
essential fatty acids.
4. Rancidity causes economical loss
because rancid fat is inedible.
 Analysis and Identification of fats and oils
(Fat Constants)
Fat constants or numbers are tests used for:
1. Checking the purity of fat for detection
of adulteration.
2. To quantitatively estimate certain
properties of fat.
3. To identify the biological value and
natural characteristics of fat.
4. Detection of fat rancidity and presence
of toxic hydroxy fatty acids.
1-Iodine number (or value):
Definition: It is the number of grams of iodine
absorbed by 100 grams of fat or oil.
Uses: It is a measure for the degree of
unsaturation of the fat, as a natural property
for it.
Unsaturated fatty acids absorb iodine at their
double bonds, therefore, as the degree of
unsaturation increases iodine number and
hence biological value of the fat increase.
It is used for identification of the type of fat,
detection of adulteration and determining the
biological value of fat.
2-Saponification number (or value):
Definition: It is the number of milligrams of
KOH required to completely saponify one
gram of fat.
Uses:
Since each carboxyl group of a fatty acid
reacts with one mole of KOH during
saponification, therefore, the amount of alkali
needed to saponify certain weight of fat
depends upon the number of fatty acids
present per weight.
Thus, fats containing short-chain acids will
have more carboxyl groups per gram than
long chain fatty acids and consume more
alkali, i.e., will have higher saponification
number.
3-Acids Number (or value):
Definition:
It is the number of milligrams of KOH required
to neutralize the free fatty acids present in
one gram of fat.
Uses:
It is used for detection of hydrolytic rancidity
because it measures the amount of free fatty
acids