BCH2132: Chemistry of Lipid (MBBS/BDS)

By

UMAR AMINU

Biochemistry Department, BUK

Relevance of Biochemistry to Medicine
• Biochemistry is the study of chemical processes occurring in living
organisms.
• Without biochemistry, we wouldn’t be able to understand how our
bodies work.
• Biochemistry, in tandem with medical physiology, aims to evaluate the
functioning of the systems found in the human body to later diagnose
abnormalities or diseases.
• Without biochemistry, healthcare professionals wouldn’t have access
to the processes taking place in humans and other living organisms.
 Lipids Chemistry
• Lipids are a heterogeneous group of organic substances that are
relatively insoluble in water (and other polar solvents) but soluble in
organic solvents (such as chloroform, ethanol, ether and benzene).
• Lipids are of great importance to the body as the chief concentrated
storage form of energy, besides their role in cellular structure and
various other biochemical functions.
• They occur naturally in most animals, microorganisms and plants.
• Examples are Fats and oils (triglyceride), waxes (e.g., beeswax),
steroids (e.g., cholesterol), fat-soluble vitamins (e.g., progesterone),
phospholipids, etc.
Biological importance of lipids
Act as fuel (source of energy) in the body.

Deposits of fats underneath the skin exert insulating effects.

The fat around organs (e.g., kidney) functions in padding and

protecting internal organs.
Building materials (e.g., cholesterol in steroid hormone synthesis).

Structural and metabolic roles.

Classification of Lipids
1. Simple lipids:
• Are esters that fatty acids form with various alcohols.
• Simple lipids include fats, oils & waxes.
• Fats and oils are esters of fatty acids and glycerol.
• Waxes are esters of fatty acids and long-chain monohydroxy alcohols
(mostly 12-34 C-atoms in length).
2. Compound Lipids:

• Consist of fatty acids, an alcohol and one or

more other chemical groups such as phosphorus
or nitrogen.
• Phospholipids, Glycolipids, Sulpholipids,
Lipoproteins.
– Phospholipids: Fatty acids + glycerol + phosphoric
acid + nitrogenous compound (e.g., lecithin, serine).
– Glycolipids: Lipids + carbohydrate.
– Sulpholipids: Lipids containing sulphate groups.
– Lipoproteins: Lipids + protein.
Derived Lipid

• These are the derivatives obtained on the hydrolysis of group1 and

group 2 lipids which possess the characteristics of lipids.

• These include glycerol and other alcohols, fatty acids, mono-and

diacylglycerols, lipid (fat) soluble vitamins, steroid hormones,
hydrocarbons and ketone bodies.
Physical Properties of Fats
• Greasy to touch and leaves an oily impression on paper.
• Are insoluble in water but soluble in organic solvents.
• The relative density of fat is less than that of water (solid fat= 0.86,
liquid fat = 0.95, water 1.0 g/cm3)  hence floats on water.
• Pure glycerides are tasteless, odourless, colourless and neutral in
reaction.
Differences Between Fats & Oils
• Fats are solid or semi-solid at room temperature.
 The triacylglycerol in fats contain mainly saturated fatty acid.

• Oils are liquid at room temperature.

 The triacylglycerol in oils contain mainly unsaturated fatty acids.
Melting points of unsaturated fatty acids are lower than those for
saturated fatty acids.
Triacylglycerol
• The simplest lipids constructed from fatty acids are the
triacylglycerols, also referred to as triglycerides, fats or neutral fats.
• Triacylglycerols are composed of three fatty acids each in ester linkage
with a single glycerol.

Formation of triacylglycerols from

glycerol and 3 fatty acids
Fatty Acids
• A fatty acid is a naturally occurring carboxylic acid with an alipathic
chain, which is either saturated or unsaturated.
• Saturated fatty acids do not contain double bonds, while unsaturated
fatty acids contain one or more double bonds.
• Both saturated and unsaturated fatty acids almost equally occur in the
natural lipids.
• Fatty acids with one double bond are mono unsaturated, and those
with 2 or more double bonds are collectively known as
polyunsaturated fatty acids (PUFA).
Even and Odd Carbon Fatty Acids

• Most of the fatty acids that occur in natural lipids are of even
carbons(usually 14C-20C).
• This is due to the fact that biosynthesis of fatty acids mainly occurs
with the sequential addition of 2 carbon units.
• Palmitic acid (l6C) and stearic acid (l8C) are the most common.
• Among the odd chain fatty acids, propionic acid (3C) and valeric acid
(5C) are well known.
Essential Fatty Acids(EFA)
• The fatty acids that cannot be synthesized by the body and, therefore,
should be supplied in the diet.
• Chemically, they are polyunsaturated fatty acids, namely :
• linoleic acid (18 : 2; 9, 12)
• Iinolenic acid (18 : 3; 9, 12, 15)
Note that: Arachidonic acid (20 :4;5,8, 11,14) becomes essential, if its
precursor linoleic acid is not provided in the diet in sufficient amounts.
Functions of EFA
• Membrane structure and function,
• Transport of cholesterol
• Formation of lipoproteins
• Prevention of fatty liver
• Eicosanoids synthesis
Deficiency of EFA
The deficiency of EFA results in phrynoderma or toad skin,
characterized by the presence of
• horny eruptions on the posterior and lateral parts of limbs

• loss of hair

• poor wound healing

Nomenclature of Fatty Acids
• Common names of fatty acids are generally derived from either the
Latin or Greek name of their source of origin.
• Examples of common names:
 Palmitic acid (from Latin: Palma - palm tree)
Stearic acid (from Greek: ‘stear’ or tallow)
 Arachidic acid (from Greek: Arachne - spider). Etc.
Numbering Of Carbon Atoms
• lt starts from the carboxyl carbon which is taken as number 1.
• The carbons adjacent to this (carboxyl C) are 2, 3, 4 and so on or
alternately α, β, γ and so on.
• The terminal carbon containing methyl group is known omega (or)
carbon. Starting from the methyl end, the carbon atoms in a fatty acid
are numbered as omega 1, 2, 3 etc.
The numbering of carbon atoms in two different ways is given below
Cont.,
• IUPAC or Systematic name of a fatty acid is formed
by replacing the ending -e with suffix -oic acid in the
name of the alkane with the same number of carbon
atoms.
• The carboxyl carbon is numbered as carbon number
one.
• Examples:
16C fatty acid is: Hexadecanoic acid
18C fatty acid is: Octadecanoic acid
 Cont.,
• The delta (∆) system is used to indicate the position of a
double bond in fatty acids where the carboxyl carbon is the first
carbon atom (C-1).
Number of C-atoms in the fatty acid: Number of double bonds: Position
of double bonds
Examples
－ Palmitoleic acid; C16:1:9 (or C16:1;∆9 or C16:1:∆9)
－ Oleic acid; cis- ∆9 -Octadecenoic acid; C18:1; ∆9
－ Linoleic acid; cis-9,12-octadecadienoic acid; 18:2;9,12.
Examples of Unsaturated Fatty Acids
Examples of Saturated Fatty Acids
Chemical Properties of Fat
• Hydrolysis: Triglycerides could be broken down (hyrolysed) in the
presence of heat or enzymes (lipases).
Cont.,
• Acrolein Formation: Formed when oil is used in cooking (the smell of
burnt fat). Acrolein is formed when glycerol is broken down by heat.
Cont.,
• Hydrogenation: Is the process that converts liquid vegetable oils into
solid or semi-solid fats by adding hydrogen across double bonds. E.g.,
margarine. (hardening).
Cont.,
• Halogenation: Is the addition of a halogen (e.g. bromine, iodine,
fluorine) to a fat. The halogen is added at the double bond of
unsaturated fatty acids.
• Iodine number: Is a measure of the degree of unsaturation of fats. It is the
amount of iodine taken up by 100 grams of fat.
Cont.,
• Saponification: Is the hydrolysis of fat by alkali to generate alkali salts of
fatty acids (soap).

• Saponification number: Is the number of milligrams of KOH required to

saponify one gram of fat.
 It is a measure of the average molecular weight of the fatty acids in a fat sample.
Cont.,
• Rancidity: Chemical change resulting in unpleasant odour
and taste that occur in fats, especially on aging.
• Rancidity occur when fats are exposed to light, heat, air and
moisture.
• Two types of rancidity:
Hydrolytic rancidity: Occurs by hydrolysis of fats: producing hydrolytic
products viz., fatty acids, glycerol, and/or mono and diglycerides.
Oxidative rancidity: Occurs by oxidation of unsaturated fatty acids which
may lead to the formation of aldehydes of objectionable taste and odour.
 Antioxidants such as ascorbic acid (Vitamin C) prevents rancidity.
Phospholipids
• Glycerophospholipids: The
glycerophospholipids are made up of
three components: a phosphorylated Schematic structure of a
phospholipid.
head group, a three-carbon glycerol
backbone and two hydrocarbon fatty acid
chains. Amphipathic lipid
• These lipids are amphipathic
(amphiphilic) molecules .
• they contain both a hydrophilic & a hydrophobic
moiety.
• Cell membranes are lipid bilayer membranes A section of a lipid bilayer membrane
made mainly by phospholipids.
 Chemical Structures of Glycero-
phospholipids

X = -H in phophatidate
= -CH2CH2NH3+ in phosphatidylethanolamine

= -CH2CH2NH3+ in phosphatidylcholine

= -CH2CH(COOH)NH3+ in phosphatidylserine

= -CH2CH(OH)CH2OH in phosphatidylglycerol

= -C6H12O6 in phosphatidylinositol
Lipoproteins
• Lipoprotein => Lipid + Protein
• They are involved in the transport of lipids (cholesterol,
triglycerides) to tissues.
• E.g., plasma lipoproteins: chylomicrons, low density lipoproteins
(LDL) and HDL.
Glycolipids
• Glycolipids are lipids covalently bonded to a
carbohydrate.
－Include the glyceroglycolipids and sphingoglycolipids.
－E.g., galactocerobroside, gangliosides,etc.
• They are found on the surfaces of cell membranes.
• They facilitate cellular recognition and communication.
－This is important in immune response, connections that
allow cells to connect to one another to form tissues, etc.
Steroids
• Are derived lipids having 4 rings fused together in their chemical
structure.
－ E.g.: Cholesterol, Sex hormones, Vitamin D.
THANKS

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