FATTY ACIDS

Presentation created by Mahpara Gondal

Lecturer
Rashid latif college of pharmacy
 OBJECTIVES

• CHEMISTRY OF FATTY ACIDS

• NOMENCLATURE OF FATTY ACIDS
• CLASSIFICATION OF FATTY ACIDS
• SATURATED
• UNSATURATED
• BRANCHED
• SUBSTITUTED
• CYCLIC
• EICOSANOIDS
 FATTY ACIDS
• BUILDING BLOCKS FOR TRIGLYCERIDES AND PHOSPHOLIPIDS
• A CHAIN OF CARBON AND HYDROGEN ATOMS WITH A CARBOXYL GROUP AT
THE ALPHA END AND A METHYL GROUP AT THE OMEGA END

Figure 5.1
 FATTY ACIDS CHEMISTRY
• HIGHER RATIO OF CARBON AND HYDROGEN TO OXYGEN THAN IN
CARBOHYDRATES AND PROTEIN
• DIFFERENT STRUCTURES IMPART DIFFERENT CHARACTERISTICS

Figure: The molecular structure of fatty acid. A. Lauric acid and B. a simplified
diagram of a fatty acid with a nonpolar tail and a polar head.
• In aqueous solution, the ions of fatty acids associate to form spherical
clusters, called micelles.
• In micelles, the nonpolar chains extend toward the interior of the structure
away from water, and the polar carboxylate groups face outward in
contact with the water.
Nomenclature of fatty acids

The systematic nomenclature of the fatty acids is based on the

Genevan system.
According to this system, the fatty acid is named after the
hydrocarbon with the same number of carbon atoms.
The suffix -oic is written in place of the final letter e in the name of
the hydrocarbon.
The names of saturated fatty acids end with the suffix –
anoic e.g., Octadecanoic acid.
The names of unsaturated fatty acids end with the suffix –
enoic e.g., Octadecenoic acid (Oleic acid).
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 C2 is denoted as a-

carbon, C3 as b-carbon and so on, while the terminal methyl (-
CH3) carbon is known as w-carbon.
The notation most commonly used for fatty acids indicates the:
•Number of carbon atoms, and
•Number of double bonds.
The notation 18:0 denotes an C18 fatty acid with no double bonds,
while 18:1 signifies an C18 fatty acid with one double bond.
To specify double-bond positioning within the carbon chain of an unsaturated fatty
acid, the preceding notation is expanded by adding the Greek capital letter delta (D)
followed by one or more superscript numbers.
The notation 18:3(D9,12,15) denotes a C18 PUFA with three double bonds at locations
between carbons 9 and 10, 12 and 13, and 15 and 16.
 Selected Fatty Acids of Biological Importance

Saturated Fatty Acids

Common Structural Formula Common Sources
Name Notation
Lauric Acid 12:0 CH3(CH2)10COOH Laurel oil, Spermaceti
Myristic Acid 14:0 CH3(CH2)12COOH Butter and wool fat
Palmitic Acid 16:0 CH3(CH2)14COOH Palm Oil
Stearic Acid 18:0 CH3(CH2)16COOH Animal and plant fats
Arachidic Acid 20:0 CH3(CH2)18COOH Peanut Oil
 Selected Fatty Acids of Biological Importance
Unsaturated Fatty Acids

Common Name Structural Formula Common Sources

Notation

Oleic Acid 18:1 – D9 CH3(CH2)7CH=CH(CH2)7COOH Animal and plant fats

Peanut & cottonseed

Linoleic Acid 18:2 – D9,12 CH3(CH2)4CH=CH(CH2)CH=CH(CH2)7COOH
Oil

Linolenic Acid 18:3 – D9,12,15 CH3(CH2CH=CH)3(CH2)7COOH Linseed Oil

Arachidonic Acid 20:4 – D5,8,11,14 CH3 (CH2)4(CH=CHCH2) 4(CH2)2COOH Animal fats

 Isomerism in Fatty acids
The unsaturated fatty acids exhibit geometric (or cis-trans) isomerism at the double
bonds.
In biochemically important MUFAs, the configuration about the double bond is
nearly always cis rather than trans.
‘Cis’ form is comparatively unstable and is more reactive.
For example, Oleic acid can exist in two forms: cis-oleic acid and trans-oleic acid
which is also called elaidic acid.
Cis’ configuration creates a rigid 30o bend, or kink, in the fatty
acid chain that is not found in saturated fatty acids.

Such a bend affects the physical properties of a fatty acid.

 TYPES OF FATTY ACIDS (VARY IN DEGREE OF
SATURATION)

• A) SATURATED FATTY ACIDS

• ALL THE CARBONS ON THE FATTY ACID ARE BOUND TO HYDROGEN
• USUALLY MORE SOLID AT ROOM TEMPERATURE
• HIGHER MELTING POINT
• MORE STABLE
 Their general formula is CnH2n+1 COOH
Examples:
• Acetic acid CH COOH
3

• Propionic acid C H COOH 2 5

• Butyric acid C H COOH

3 7

• Caproic acid C H COOH

5 11

• Palmitic acid C H COOH

15 31

• Stearic acid C H COOH and so on.

17 35

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,
 FATTY ACIDS VARY IN SATURATION
• A) UNSATURATED FATTY ACIDS
• SOME CARBONS FORM A DOUBLE BOND WITH EACH OTHER INSTEAD OF BINDING
TO HYDROGEN
• MONOUNSATURATED FATTY ACID (MUFA)
• HAS ONE CARBON TO CARBON (C=C) DOUBLE BOND
• POLYUNSATURATED FATTY ACID (PUFA)
• HAS TWO OR MORE CARBON TO CARBON (C=C)DOUBLE BONDS
• MORE LIQUID AT ROOM TEMPERATURE
• LOWER MELTING POINT
• LESS STABLE
SATURATED AND UNSATURATED FATTY
ACIDS HELP SHAPE FOODS

Figure 5.3
 MONOUNSATURATED FATTY
ACIDS
• A MONOUNSATURATED FATTY ACID IS A FATTY ACID WITH
A CARBON CHAIN IN WHICH ONE CARBON–CARBON
DOUBLE BOND IS PRESENT.
• FOR EXAMPLE, OLEIC ACID IS A MONOUNSATURATED FATTY
ACID, THAT IS FOUND IN NEARLY ALL FATS.
b) POLYUNSATURATED FATTY ACIDS
• A POLYUNSATURATED FATTY ACID IS A FATTY ACID WITH A
CARBON CHAIN IN WHICH TWO OR MORE CARBON–CARBON
DOUBLE BONDS ARE PRESENT.
• UP TO SIX DOUBLE BONDS ARE FOUND IN BIOCHEMICALLY IMPORTANT
PUFAS; THEY INCLUDE:
• DIENOIC ACIDS SERIES HAVE TWO DOUBLE BONDS, E.G. LINOLEIC ACID
• TRIENOIC ACIDS SERIES HAVE THREE DOUBLE BONDS, E.G. LINOLENIC ACID
• TETRAENOIC ACID SERIES WITH FOUR DOUBLE BONDS, E.G. ARACHIDONIC
ACID
 FATTY ACIDS DIFFER IN DOUBLE-BOND
LOCATION
• THE LOCATION OF THE FIRST DOUBLE BOND IN UNSATURATED FATTY ACIDS
AFFECTS THE NAMING AND CHARACTERISTICS OF THE UNSATURATED FATTY
ACIDS

• OMEGA-3 FATTY ACID

• FIRST DOUBLE BOND IS BETWEEN THE THIRD AND FOURTH CARBON FROM THE
OMEGA END
• EXAMPLE: ALPHA-LINOLENIC ACID (ALA)
• ONE OF THE TWO ESSENTIAL FATTY ACIDS

• OMEGA-6 FATTY ACID

• FIRST DOUBLE BOND IS BETWEEN THE SIXTH AND SEVENTH CARBON FROM THE
OMEGA END
• EXAMPLE: LINOLEIC ACID
• ONE OF THE TWO ESSENTIAL FATTY ACIDS
THE ESSENTIAL FATTY ACIDS: OMEGA-3
AND OMEGA-6

Figure 5.4
UNSATURATED FATTY ACIDS VARY IN SHAPE
• UNSATURATED FATTY ACIDS FORM TWO DIFFERENT SHAPES

Figure 5.5
 FATTY ACIDS AND RANCIDITY
• RANCIDITY: SPOILING OF FATS THROUGH OXIDATION
• THE MORE DOUBLE BONDS THERE ARE, THE MORE SUSCEPTIBLE TO OXIDATION AND
RANCIDITY

PUFA > MUFA > SATURATED FATTY ACIDS

• WAYS TO ENHANCE STABILITY OF FATTY ACIDS AND REDUCE RANCIDITY
• ADDING ANTIOXIDANTS
• LIMITING FOOD EXPOSURE TO OXYGEN, HEAT, AND LIGHT
• HYDROGENATION (PARTIAL OR FULL)
(c) Branched chain FA: Odd and even carbon branched
chain fatty acids occur in animal and plant lipids, e.g.
• Sebaceous glands: Sebum contain branched chain FA
• Branched chain FA is present in certain foods, e.g.
phytanic acid in butter.

(d) 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 – CH group
3

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.
(e) Cyclic fatty acids: Fatty acids bearing cyclic groups are
present in some seeds, e.g.
• Chaulmoogric acid obtained from chaulmoogra seeds,
• Hydnocarpic acid.
Biomedical Importance
Both of them have been used earlier for long time for treatment of leprosy.
(f) Eicosanoids: These are derived from eicosapolyenoic
FA.
 Essential fatty acids
Essential fatty acids are those polyunsaturated fatty acids that cannot be
synthesized by our cells and we should obtain them from plants through diet.
Linoleic acid and linolenic acid are the only essential fatty acids for animals.
Other polyunsaturated fatty acids can be synthesized from these essential fatty
acids.
For example, arachidonic acid can be synthesized only from linoleic acid.
Therefore, in deficiency of linoleic acid, arachidonic acid also becomes an
essential fatty acids.
 IMPORTANCE of Essential Fatty Acids
Linoleic acid is the starting material for the biosynthesis of arachidonic acid.
Arachidonic acid is the major starting material for eicosanoids, substances that
help regulate blood pressure, clotting, and several other important body functions.
Linolenic acid is the starting material for the biosynthesis of two additional
omega-3 fatty acids.
Linolenic acid (18:3) → EPA (20:5) → DHA (22:6)

EPA (eicosapentaenoic acid) and DHA (docosahexaenoic acid) are important

constituents of the communication membranes of the brain and are necessary
for normal brain development.
EPA and DHA are also active in the retina of the eye.
Functions of EFA: (Biomedical Importance)

• Structural elements of tissues: Polyunsaturated fatty acids occur in higher

concentration in lipids associated with structural elements of tissues.
• Structural element of gonads: Lipids of gonads also contain a high concentration
of polyunsaturated fatty acids, which suggests importance of these compounds in
reproductive function.
• Synthesis of prostaglandins and other compounds:
Prostaglandins are synthesised from Arachidonic acid by cyclooxygenase enzyme
system. Leucotrienes are conjugated trienes formed from arachidonic acid in
leucocytes by the Lipoxygenase pathway.
• Structural element of mitochondrial membrane: A deficiency of EFA causes
swelling of mitochondrial membrane and reduction in efficiency of oxidative
phosphorylation. This may explain for increased heat production noted in EFA
deficient animals.
Serum level of cholesterol: Fats with high content of polyunsaturated fatty
acids tends to lower serum level of cholesterol.
• Effect on clotting time: Prolongation of clotting time is noted in ingestion of
fats rich in EFA.
• Effect on fibrinolytic activity: An increase in fibrinolytic activity follows the
ingestion of fats rich in EFA.
• Role of EFA in fatty liver: Deficiency of EFA produces fatty liver.
• Role in vision: Docosahexaenoic acid (22:6n-3) is the most abundant
polyenoic fatty acids present in retinal photoreceptor membranes.
Docosahexaenoic acid is formed from dietary linolenic acid. It enhances the
electrical response of the photoreceptors to illumination. Hence linolenic acid
is necessary in the diet for optimal vision