LIPIDS

Dr.B.RENGESH | M.Tech., Ph.D.

Associate Professor, Department of Pharmaceutical Technology,
Mahendra Engineering College (Autonomous),
Namakkal District, Tamil Nadu, India
v Lipids are organic compounds formed mainly from alcohol and fatty acids
combined together by ester linkage.

v Lipids are biological molecules that are insoluble in water but soluble in
nonpolar solvents (ether, chloroform, benzene, acetone).
v Lipids are the waxy, greasy, or oily compounds found in plants and animals.
 BIOLOGICAL IMPROTANCE OF LIPIDS
v They are more palatable and storable to unlimited amount compared to
carbohydrates.
v They have a high-energy value (25% of body needs) and they provide
more energy per gram than carbohydrates and proteins but carbohydrates
are the preferable source of energy.
v Supply the essential fatty acids that cannot be synthesized by the body.
v Supply the body with fat-soluble vitamins (A, D, E and K).
v They are important constituents of cell membrane and nervous system.
 BIOLOGICAL IMPROTANCE OF LIPIDS
v Stored lipids “depot fat” is stored in all animal cells act 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.
v Lipids provide bases for dealing with diseases such as obesity,
atherosclerosis, lipid-storage diseases, essential fatty acid deficiency,
respiratory distress syndrome,
 CLASSIFICATION OF LIPIDS

contain esters

contain 2 types of components (a contain > 2 types of components

fatty acid & an alcohol) (a fatty acid, an alcohol & others)
 FATTY ACIDS
v a fatty acid is a carboxylic acid with a long aliphatic chain, which is either
saturated or unsaturated.
 FATTY ACIDS
Properties:
• The long, nonpolar hydrocarbon tails of fatty acids are responsible for most
of the fatty or oily characteristics of lipids.
• The carboxyl (COOH) group is hydrophilic (polar) under basic conditions,
such as physiological pH (7.4)
• Fatty Acid Micelles

Micelles are important in the transport of insoluble lipids

in the blood
 FATTY ACIDS
Characteristics:
• The chain length ranges from 4 to 30 carbons; 12-24 is most common.
• The chain is typically linear, and usually contains an even number of
carbons
• The many fatty acids which occur naturally arise primarily through
variation of chain length and degree of saturation
• There may be one double bond or many, up to six in important fatty acids.
 FATTY ACIDS
Characteristics:
• When double bonds occur they are almost always cis. If there is more than 1
double bond, they occur at three-carbon intervals

e.g., -C=C-C-C=C-.
This is called
divinylmethane pattern.
FATTY ACIDS - Classification based on number of double bonds & Nomenclature
• If without double bonds: Saturated Fatty Acids
• If with double bonds: Unsaturated Fatty Acids
o 1 double bond: Monounsaturated fatty acids
o 2 or more double bonds: Polyunsaturated fatty acids
 List of some Saturated Fatty Acids
Structural
Common Name Systematic Name Lipid Numbers
Formula
Propionic acid Propanoic acid CH3CH2COOH C3:0
Butyric acid Butanoic acid CH3(CH2)2COOH C4:0
Valeric acid Pentanoic acid CH3(CH2)3COOH C5:0
Caproic acid Hexanoic acid CH3(CH2)4COOH C6:0
Caprylic acid Octanoic acid CH3(CH2)6COOH C8:0
Capric acid Decanoic acid CH3(CH2)8COOH C10:0
Myristic acid Tetradecanoic acid CH3(CH2)12COOH C14:0
Palmitic acid Hexadecanoic acid CH3(CH2)14COOH C16:0
Stearic acid Octadecanoic acid CH3(CH2)16COOH C18:0
 List of some Mono-Unsaturated Fatty Acids
Common Name Chemical Name Lipid Numbers
Myristoleic acid cis-Tetradec-9-enoic acid 14:1 (n-5)
Palmitoleic acid cis-Hexadec-9-enoic acid 16:1 (n-7)
Oleic acid cis-Octadec-9-enoic acid 18:1 (n-9)
Elaidic acid (trans-oleic acid) trans-Octadec-9-enoic acid 18:1 (n-9)
11-Eicosenoic acid (gondoic acid) cis-Eicos-11-enoic acid 20:1 (n-9)
 Common Name Lipid Numbers Chemical Name

List of some Omega-3 Poly-Unsaturated Fatty Acids

Alpha-linolenic acid 18:3 (n-3) all-cis-9,12,15-octadecatrienoic acid
Eicosapentaenoic acid 20:5 (n-3) all-cis-5,8,11,14,17-eicosapentaenoic acid
Docosahexaenoic acid 22:6 (n-3) all-cis-4,7,10,13,16,19-docosahexaenoic acid
List of some Omega-6 Poly-Unsaturated Fatty Acids
Linoleic acid 18:2 (n-6) all-cis-9,12-octadecadienoic acid
Gamma-linolenic acid 18:3 (n-6) all-cis-6,9,12-octadecatrienoic acid

α-linolenic acid 𝛄-linolenic acid

 FATTY ACIDS – Melting Property
• Shorter fatty acids usually have lower melting points than longer ones
(stearic acid [18C] = 70ºC, palmitic acid [16C] = 63ºC)

• The cis-double bonds in

unsaturated fatty acids put an
inflexible “kink” in the carbon
chain, preventing the molecules
from packing together as tightly
as saturated fatty acids do.
 STRUCTURE OF FATS AND OILS
TRIGLYCERIDES

• Animal fats and

vegetable oils are
esters composed of
three molecules of a
fatty acid connected to
a glycerol molecule,
producing a structure
called a triglyceride or
a triacylglycerol
 TRIGLYCERIDES

• The fatty acids in a triglyceride molecule are usually not all the same;
natural triglycerides are often mixtures of many different triglyceride
molecules
 TRIGLYCERIDES
• Fats are triglycerides that are solids at room temp.
– usually derived from animals & mostly saturated fatty acids
• Oils are triglycerides that are liquids at room temp.
– usually derived from plants or fish & mostly unsaturated fatty acids
TRIGLYCERIDES - Hydrolysis
 TRIGLYCERIDES - Saponification

carboxylate salts
of the fatty
acids
TRIGLYCERIDES - Hydrogenation
 WAXES
• Waxes are simple lipids contain a fatty acid joined to a long-chain (12-32
carbons) alcohol
 WAXES
• Waxes are insoluble in water, and not as easily hydrolysed as fats and oils.
They often occur in nature as protective coatings on feathers, fur, skin,
leaves, and fruits.
• Sebum, secreted by the sebaceous glands of the skin, contains waxes that
help to keep skin soft and prevent dehydration.
• Waxes are used commercially to make cosmetics, candles, ointments, and
protective polishes.
 PHOSPHOGLYCERIDES
• Phosphoglycerides are complex lipids that are major components of cell
membranes. Phosphoglycerides and related compounds are also called
phospholipids.
 PHOSPHOGLYCERIDES - Aminoalcohols
• The most abundant phosphoglycerides contain the alcohols choline,
ethanolamine, or serine attached to the phosphate group.
 PHOSPHOGLYCERIDES – (Aminoalcohol) – Lecithin
• Phosphoglycerides that contains the aminoalcohol ‘choline’ are called
lecithins.

• The fatty acids at the first and second positions are variable, so there are a
number of different possible lecithins.
• They act as an emulsifying agent
 PHOSPHOGLYCERIDES – (Aminoalcohol) – Cephalin
• Phosphoglycerides that contains the aminoalcohol ‘ethanolamine or serine’
are called lecithins.

• Cephalins are found in most cell membranes, and are particularly abundant in
brain tissue. They are also found in blood platelets, and play a role in blood-
clotting.
 SPHINGOLIPIDS
• Sphingolipids are complex lipids that contain sphingosine instead of glycerol.
 SPHINGOLIPIDS - Spingomyelin
• One important type of sphingolipds are the sphingomyelins.

SPINGOMYELIN

• Sphingomyelins are found brain and nerve tissue,

and in the myelin sheath that protects nerves
SPHINGOLIPIDS - Spingomyelin

• Sphingomyelins - a
bilayer that wraps
around nerve cell
axons
 SPHINGOLIPIDS - Glycolipids
• Glycolipids are sphingolipids that contain carbohydrates (usually
monosaccharides). They are also referred to as cerebrosides because of their
abundance in brain tissue

Cerebroside
BIOLOGICAL MEMBRANES - Membrane Structure
• Most cell
membranes
contain about
60% lipids
(Amphipathic
Lipids) and
40% proteins.
• The fluid-
mosaic model :
Cell membrane
- Lipid bilayer
membrane re-
forming @ damage
The Fluid Mosaic Model
 STERIODS
• Steroids are classified as lipids because they are soluble in nonpolar solvents,
but they are non-saponifiable because the components are not held together
by ester linkages
• The basic steroid structure contains four fused rings

• There are three important types of

steroids:
1) Cholesterol
2) Steroid hormones
3) Bile salts
 STERIODS - Cholesterol
• Cholesterol is the most abundant steroid in the body.
• it is manufactured in the liver.
• It is an essential component of cell membranes, and is a precursor for other
steroids, such as the bile salts, sex hormones, vitamin D, and the
adrenocorticoid hormones.
• There is apparently a correlation
between high levels of cholesterol in
the blood and atherosclerosis.
 STERIODS – Steroid hormones
• Hormones, molecules that regulate the function of organs and tissues, come
in a variety of forms.
• Some, such as sex hormones and adrenocorticoid hormones, are steroids
• Sex hormones produced in the testes and ovaries regulate the production of
sperm and eggs and aid in the development of secondary sex characteristics
Eg.: testosterone, estradiol, progesterone
• Adrenocorticoid hormones are produced in the adrenal glands (located on
the top of the kidney). Eg.: Glucocorticoids - Cortisol and its derivatives,
cortisone and prednisolone
STERIODS
Sex hormones
 STERIODS
Adrenocorticoid
hormones
 STERIODS - Bile Salts
• Bile is a yellowish brown or green fluid produced in the liver and stored in
the gall bladder.
 PROSTAGLANDINS
• Prostaglandins are cyclic compounds synthesized from arachidonic acid.
Like hormones, they are involved in a host of body processes, including
reproduction, blood clotting, inflammation, and fever.
• Prostaglandins have a wide range of biological effects:
– causing pain
– causing inflammation
– causing fever
– affecting blood pressure
– inducing labor (PGE2)
PROSTAGLANDINS

Dinoprostone

Carboprost