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Study Of Derived Lipids
Study Of Fatty Acids
FATTY ACIDS( FAs)
Class- Derived Lipids
BASIC COMPONENT
OF LIPID FORMS
What are Fatty Acids?
Fatty Acids Are Derived Lipids
? Fatty acids are of Class Derived Lipids:
?Since Fatty acids are Hydrolytic
products of Simple and Compound
Lipids.
Fatty Acids (FA)
? Fatty Acids (FA) are relatively or
potential y related to various Lipid
structures.
?Simple Lipids
?Compound Lipids
?Derivatives of Lipids
Structure And Chemical Nature
Of Fatty Acids
Chemical Structure Of Fatty Acids
Fatty acid Structures Has
Varied Hydrocarbon Chains
? The Hydrocarbon chain of
each Fatty acid is of varying
chain length (C2 - C26).
Human Body Fatty Acid From C2-C26
S.No Fatty Acid Name Fatty Acid Structure has
Carbon atoms
1
Acetic Acid
C2
2
Propionic Acid
C3
3
Butyric Acid
C4
4
Valeric Acid
C5
5
Palmitic
C16
6
Stearic
C18
7
Oleic
C18
S.No
Fatty Acid Name
Fatty Acid Structure
8
Linoleic Acid
C18
9
Arachidic Acid
C20
10
Arachidonic Acid
C20
11
Behenic acid
C22
12
Lignoceric acid
C24
13
Cerotic acid
C26
? Fatty acid structure have two
ends:
? Carboxylic group(-COOH) at one end (Delta end
denoted as /Alpha end )
? Methyl group (-CH3) at another end (Omega
end denoted as )
Carboxylic Acid Functional Group Of
Fatty Acid
Definition of Fatty acids
Fatty Acids are Defined as:
? Fatty acids are chemical y Organic acids
? With Aliphatic Hydrocarbon chain (of varying
length C2 to C26) with Mono terminal
Carboxylic acid group as functional group.
Different Forms Of
Fatty acids In Body
Free Fatty acid /Unesterified Fatty acid
? Fatty acid who has free Carboxylic group
? Fatty acid not reacted and linked to an
Alcohol by an Ester bond.
Esterified Fatty acid/Bound form of Fatty Acid
?Fatty acid has no free Carboxylic
group
?Fatty acid is linked to an Alcohol
with an Ester bond.
Classification of Fatty acids
Biomedical y Important Fatty Acids
Based On Six Different Modes:
? Classification of FAs Based on Six Modes:
1. Total number of Carbon atoms in a Fatty acid structure
2. Hydrocarbon chain length of Fatty acid
3. Bonds present in Fatty acid
4. Nutritional requirement of Fatty acid
5. Chemical Nature and Structure of Fatty acids
6. Geometric Isomerism of UFAs
Fatty acids Based on
Total Number of Carbon atoms
?Even numbered Carbon Atom Fatty
acids (2,4,6,8,16,18,20 etc)
?Odd numbered Carbon Atom Fatty
acids (3,5,7,---)
? Most natural y occurring /human body Fatty
acids are even carbon numbered FAs.
? Since biosynthesis of Fatty acids uses 2
Carbon units Acetyl-CoA (C2).
? Examples of Even Carbon Numbered
Fatty acids:
? Butyric Acid (C4)
? Palmitic Acid (C16)
? Stearic Acid (C18)
? Oleic Acid (C18) (Most Common)
? Linoleic acid (C18)
? Linolenic Acid (C18)
? Arachidic acid (C20)
? Arachidonic acid (C20)
? Odd Carbon numbered Fatty acids are less related to
human body
? Example of Odd carbon Fatty acid associated to
human body
?Propionic Acid ( 3C)
Fatty acids Based on
Nature and Number of Bonds present
? Saturated Fatty acids(SFAs)
? Fatty acids having single bonds in hydrocarbon
chain structure.
? Examples:
? Acetic acid (C2)
? Butyric acid (C4)
? Palmitic acid (C16)
? Stearic acid (C18)
? Arachidic acid(C20)
? Unsaturated Fatty acids (UFAs)
? Fatty acids having double bonds in its structure.
? Types of UFAs:
? Monounsaturated Fatty acids (MUFAs)
? Polyunsaturated Fatty acids (PUFAs)
? Human body have no Enzyme system to introduce
double bond beyond Carbon atom 10 in the
hydrocarbon chain.
? Hence PUFAs are not biosynthesized
in human beings.
? Monounsaturated Fatty Acids(MUFAs):
? MUFAs have one double bond in a fatty acid structure
? Examples of MUFAs :
? Palmitoleic acid (C16:1;9) (7)
? Oleic acid (C18:1;9)(9)
? Erucic acid (C22:1;9)(9)
? Poly Unsaturated Fatty Acids (PUFAs):
? UFAs with two or more double bonds in
the structure are termed as PUFAs.
? Examples Of PUFAS:
? Linoleic(18:2;9,12) (6)
? Linolenic(18:3;9,12,15) (3)
? Arachidonic(20:4;5,8,11,14) (6)
? Timnodonic (20:5;5,8,11,14,17) (3)
? Cervonic/Docosa Hexaenoic
acid(DHA)(22:6;4,7,10,13,16,19) (3)
? Remember Unsaturated Fatty acids
? Double bonds are:
? Weaker /unstable bonds.
? Get easily cleavable/metabolized
?More the degree of Unsaturation in Fatty
acids.
?More is the unstability of Fatty acids.
? Saturated Fatty acids structures are
Straight.
? Unsaturated Fatty acids structures are
bent (Kink).
? Saturated FAs: with straight structures are
tightly packed together.
? Unsaturated FAs: with bent structures are
not compact and has no tight packing.
? More the degree of unsaturation in
FA/More double bonds in FA
structure
? More is the bent of Fatty acid
structure.
Fatty acids Based on the Nutritional
Requirement
Nutritionally Essential Fatty
acids
?Nutritional y Essential Fatty acids:
?Fatty acids not biosynthesized in
human body and indispensable
through nutrition/diet are termed as
Essential Fatty acids.
?PUFAS are nutritional y essential
Fatty acids.
Examples of Essential Fatty Acids/PUFAs:
?Linoleic
?Linolenic
?Arachidonic acids
?Timnodonic and
?Cervonic
Nutritional y Non Essential Fatty acids
? Nutritional y Non essential Fatty acids:
? Fatty acids which are biosynthesized in the body
and are nutritional y non essential Fatty acids.
? Saturated Fatty acids and MUFAs are non essential
Fatty acids.
Examples Of Non Essential Fatty Acids
? Palmitic
? Stearic
? Oleic acid
Based on Geometric Isomerism of
Unsaturated Fatty acids
? Cis Fatty Acids:
The Groups around double bond of Unsaturated FAs
are on same side.
? Examples:
? Cis Oleic acid (rich in Olive oil)
? Palmitoleic acid
? Trans Fatty Acids :
? The groups around double bond of UFAs are on
opposite side
? Example :
? Elaidic acid /Trans Oleic acid (Hydrogenated
Fats )
Types Of Fatty acids Based on
Hydrocarbon chain length
? Short Chain Fatty acids (2-6 Hydrocarbon Chain length)
? Examples:
? Acetic acid (C2)
? Propionic acid (C3)
? Butyric acid (C4)
? Valeric acid (C5)
? Caproic acid (C6)
? Medium Chain Fatty acids (8-14 Carbon length)
? Examples:
? Caprylic acid (C8)
? Capric acid (C10)
? Lauric acid (C12)
? Myristic acid (C14)
? Long Chain Fatty acids ( 16-20 Carbon length)
? Examples:
? Palmitic acid (C16)
? Palmitoleic acid (C16)
? Stearic acid (C18 )
? Oleic acid (C18)
? Linoleic acid (C18)
? Linolenic acid (C18)
? Arichidic acid (C20)
? Arachidonic acid /ETA(C20)
? Timnodonic acid/EPA (C20)
? Very Long Chain Fatty Acids (C22 onwards )
? Examples:
? Behenic acid/Docosanoic (C22)
? Erucic acid/Docosa 13 Enoic (C22)
? Clupanodonic/Docosapentaenoic acid (DPA) (C22)
? Cervonic acid/DocosaHexaenoic (DHA) (C22)
? Lignoceric acid /Tetracosanoic (C24)
? Nervonic /Tetracosaenoic (C24)
? Cerotic acid/Hexacosanoic (C26)
Fatty acids Based on
Chemical Nature and Structure
?Aliphatic Fatty acids:
Straight Hydrocarbon chain
? Examples:
?Palmitic acid (C16)
?Stearic acid (C18)
? Branched Chain Fatty acids:
? Possess Branched chains
? Examples:
?Isovaleric (C5)
?Phytanic acid (Butter , dairy products)
? Cyclic Fatty acids :
? Contains Ring structure
? Examples:
? Chaulmoogric acid
(Used for Leprosy treatment in olden days)
? Hydnocarpic acid
? Hydroxy Fatty acids:
? Contain Hydroxyl Groups
? Examples:
? Cerebronic acid (C24)/
2-HydroxyTetracosanoic acid
? Ricinoleic acid(C18) (Castor oil)
Naming And Numbering
Of Fatty Acids
? Every Fatty acids has a:
? Common Name
? Systematic Name
? Most of the Fatty acids are known by their
common names.(Since easy to use)
? Systematic names of Fatty acids are limited
in use. (Since not easy to use)
Remember
? Long chain Fatty acids are
also termed as Acyl chains.
vThe systematic names of Saturated Fatty
acids are named by adding suffix `anoic'.
v Example : Palmitic acid- C16/ Hexadecanoic
acid
? The systematic names of Unsaturated Fatty
acids are named by suffix `enoic'.
? Example: Oleic acid- C18/ Octadecaenoic
acid
S.N Common Name Systematic Name
1
Palmitic Acid
Hexadecanoic Acid
2
Stearic Acid
Octadecanoic Acid
3
Oleic acid
Octadecaenoic acid
4
Linoleic Acid
Octadecadienoic acid
5
Linolenic Acid
Octadecatrienoic acid
6
Arachidonic acid Eicosatetraenoic acid
Numbering Of Fatty Acids
? Numbering of Carbon atoms of
Fatty acids is done from :
?Both ends of Fatty acids-
? end/ end
? end
Numbering Of Fatty acid From
Carboxyl/ end ( end)
? From Carboxyl Group end( end ) :
? Carboxylic acid group of Fatty acid is
numbered as C1
? C2 is next adjacent Carbon atom ,
? C3 and so onn..........
? Carbon atom is next to the functional
group ?COOH of a Fatty acid.
? Next to Carbon is , , , and so onn.
? Carbon atoms from Methyl(?CH3)
group /non polar end() of a fatty
acid are numbered as 1,2,3
and so onn.
Nomenclature Of Fatty
acids
? FA Nomenclature is Based On
? Chain length/Total Number of Carbon atoms in a FA.
? Count Number of Carbon atoms in FA
? Number and Position of Double bonds
? Position of double bond from Carboxyl/Delta end
? Position of double bond from Methyl/Omega
Short Hand Representations
of Fatty acids
? Short Hand Representations
of Fatty acids:
?Palmitic Acid (16:0)
?Palmitoleic acid (16:1;9)
?\
? First digit stands for total number of carbon atoms
in the fatty acid.
? Second digit designates number of double bonds.
? Third digit onwards indicates the position of
double bonds.
Fatty-acid Nomenclature
? Named according to chain length
? C18
Fatty-acid Nomenclature
? Named according to the number of
double bonds
? C18:0
Common name:
Stearic acid
Fatty-acid Nomenclature
? Named according to the number of
double bonds
? C18:1
Common name:
Oleic acid
Fatty-acid Nomenclature
? Named according to the number of
double bonds
? C18:2
Common name:
Linoleic acid
Fatty-acid Nomenclature
? Named according to the number of
double bonds
? C18:3
Common name:
Linolenic acid
Omega System Nomenclature
? Named according to the
location of the first double bond from the non-carboxyl Methyl
end (count from the Methyl end /Omega end )
Omega Fatty-acid Nomenclature
Omega 9 or n?9 fatty acid
Omega 6 or n?6 fatty acid
Omega 3 or n?3 fatty acid
?Stearic acid (18:0)
?Oleic acid (18:1;9)
?Linoleic acid (18:2;9,12)
?Linolenic acid (18:3;9,12,15)
?Arachidonic acid (20:4;5,8,11,14)
? A Fatty acid may also be designated as :
? Linoleic acid (18C;9,12)
? Linolenic acid (18C;9,12,15)
? indicates from COOH end.
? 9,12,15 are double bond positions from delta
end.
Short Hand Presentation of FA
14:0 Myristic acid
16:0 Palmitic acid
18:0 Stearic acid
18:1 cis D9 Oleic acid (9)
18:2 cisD9,12 Linoleic acid (6)
18:3 cisD9,12,15 a-Linolenic acid (3)
20:4 cisD5,8,11,14 Arachidonic acid (6)
20:5 cisD5,8,11,14,17 Eicosapentaenoic acid (3 )
22:5 CisD7,10,13,16,19 Docosapentaenoic acid (3 )
Important Properties Of Fatty Acids
Properties Of Fatty Acids
? Physical Properties
? Chemical Reactions
Physical Properties Of Fatty Acids
1. Solubility
2. Melting Point
Solubility Of Fatty Acids Depends
Upon
Factors Responsible For Solubility Of
Fatty Acids
1. Hydrocarbon chain length
2. Degree of Unsaturation- Number of Double Bonds
3. Hydrophobicity/Polarity of Fatty acids
4. Polarity of Solvents
? Smal hydrocarbon chain length are less
hydrophobic and more soluble
? Long Chain FA and VLCFA more hydrophobic are
very less soluble
? Solubility of Fatty acids decreases with increase in
Fatty acid hydrocarbon chain length.
? Double bonds increases solubility
Melting Point of Fatty Acids
Factors Responsible For
Melting Points Of Fatty Acids
1. Hydrocarbon chain length
2. Nature of Bonds
3. Degree of Unsaturation/Number of double bonds
Fatty Acids With
Decreased Melting Points
? Short and Unsaturated Fatty
acids has low melting point
? More degree of unsaturation low
is melting point of FAS
Melting Points
? Affected by chain length
?Longer chain = higher melting temp
Fatty acid: C12:0
C14:0
C16:0
C18:0
C20:0
Melting point: 44?C
58?C
63?C
72?C
77?C
Melting Points
? Affected by number of double bonds
?More saturated = higher melting temp
Fatty acid:
C18:0
C18:1
C18:2
C18:3
Melting point:
72?C
16?C
?5?C
?11?C
Fatty Acids With
Increased Melting Points
? Long and Saturated Fatty acids are
has high melting point.
? Less degree of Unsaturation more is
melting point of Fatty acids
? Thus melting point of Fatty acids(FAs):
?Increases with increase in chain
length of FAs.
?Decreases with decrease in chain
length of FAs.
?Increases with low unsaturation of
FAs
?Decreases with more unsaturation of
Fatty acids
Structures and Melting Points of Saturated Fatty Acids
Chemical Reactions Of Fatty Acids
Types Of Chemical Reactions
Of Fatty acids
Reactions due to
Carboxyl group of Fatty acids:
? Esterification/Esterified forms of Lipids
? Saponification/Soap Formation
Reactions Associated to
Double bonds of Fatty acids:
? Halogenation/Addition of Halogens around double
bond
? Hydrogenation/Transform to UFAs to SFAs
Significance Of Halogenation
?Halogenation of fatty
acids is an index of
assessing the degree of
unsaturation
? Iodine Number is a process of
Halogenation which checks the
content of SFA and PUFAs of Fats
and Oils.
? SFA has zero Iodine number.
? PUFAs has high Iodine number.
Hydrogenation Of Fatty acids
Alters Geometric Isomerism Of
Unsaturated Fatty acids
Transforms Natural Cis Form to Trans Form
Increases Shelf life of PUFAs
Al -Cis Fatty acids
Good for Health
? Human body contain Enzyme system to
metabolize Cis form of Fatty acids.
? Cis forms when ingested through food are
easily metabolized and does not retain in the
body.
? Hence All ?Cis forms are good for health and no
risk of Atherosclerosis and CVD.
? Al Cis form of fatty acids are unstable and
easily metabolizable.
? More content of Trans Fatty acids are found
in processed/Refined foods viz:
?Hydrogenated Oils (Vanaspati Dalda)
?Ghee
?Margarine
?Bakery products /Fast foods
?Deeply Fried recipes in Oils which are
prepared in repeatedly heated oils.
? Trans fatty acids increases risk of
:
?Atherosclerosis
?Cardio Vascular disorders:
?Ischemia
?Myocardial Infarction
?Stroke(Brain attack)
Message
Learnt, Understood And To Be Implemented
For Good Fatty acid metabolism and Significant Health
? Eat natural Cis forms of Fatty acids
? Avoid Hydrogenated Trans Fatty
acids
? Eat home made food
? Avoid Processed/Junk Foods
PUFAs And Omega Fatty Acids
Types Of Omega Fatty acids
?In Nutrition and Clinical
practice
?3 Fatty acids
?6 Fatty acids
?7 Fatty acids
?9 Fatty acids
Omega Fatty Acids
Omega 3 Fas
Omega 6 Fas
Omega 7 Fas
Omega 9 Fas
PUFAs
PUFAs
MUFAs
MUFAs
Linolenic
Linoleic
Palmitoleic Oleic ?
C18-(ODTA)
C18- (ODDA) C16-(HDA) C18(ODA)
Timnodonic
Erucic ?
C20-(EPA)
Arachidonic
C22(DA)
Cervonic
C20-(ETA)
Nervonic
C22-(DHA)
C24-(TA)
Clupanodonic
C22-(DPA)
Examples of 3 Fatty acids
? Linolenic (18:3;9,12,15) (3)
? Timnodonic/Ecosapentaenoic Acid /EPA
(20:5;5,8,11,14,17)(3)
? Clupanodonic acid/(Docosa Pentaenoic Acid): (DPA)
(C22:5;7,10,13,16,19 )(3)
? Cervonic/Docosa Hexaenoic Acid
(DHA)(22:6;4,7,10,13,16,19)(3)
Rich sources of dietary Omega and nutritional
essential PUFAS are:
?Vegetable Oils
?Green Leaves, Algae
?Fish and Fish oils
?Flax Seeds
Sources,Distribution,Composition Of
Fatty Acids In Human Body
Sources Of Fatty Acids To Human Body
? Exogenous Sources- Dietary Food Items
? Endogenous Biosynthesis- From Free Excess
Glucose in Liver
Forms of Dietary Fatty Acids To Be Ingested
Natural Forms Of Fatty Acids
? Fatty acids in nature mostly presently in
? Esterified form of FAs? (TAG,PL,CE)
? Even Numbered Carbon
? Unsaturated- PUFAs/Omega 3 and 6
? Cis forms
Contents Of Fatty acids Sources Of Oils
Highest Content of MUFA Olive Oil , Mustard Oil
Highest content of PUFA Safflower, Sunflower,
Flax seed Oil
Highest content of SFA
Coconut Oil
Oils Rich In
Oils rich in
Oils rich in
SFAs
MUFAs
PUFAs
Coconut Oil
Olive Oil (75%)
Flax seeds/
Linseed Oil
Palm Oil
Sunflower Oil (85%)
Soya /Safflower Oil
Butter
Ground nut /
Almond Oil
Pea nut Oil
Animal Fat
Almond Oil
Rice Bran
Sesame Oil
Walnuts Oil
Beef Fat (Tal ow Fat) 50%
Corn Oil
Lard (Pork Fat) 40%
Marine Fish
Carbons
Double bonds
Abbreviation
Source
Fatty Acids
Acetic
2
0
2:0
bacterial metabolism
Propionic
3
0
3:0
bacterial metabolism
Butyric
4
0
4:0
butterfat
Caproic
6
0
6:0
butterfat
Caprylic
8
0
8:0
coconut oil
Capric
10
0
10:0
coconut oil
Lauric
12
0
12:0
coconut oil
Myristic
14
0
14:0
palm kernel oil
Palmitic
16
0
16:0
palm oil
Palmitoleic
16
1
16:1
animal fats
Stearic
18
0
18:0
animal fats
Oleic
18
1
18:1
olive oil
Linoleic
18
2
18:2
grape seed oil
Linolenic
18
3
18:3
flaxseed (linseed) oil
Arachidonic
20
4
20:4
peanut oil, fish oil
Fatty acid Composition
of Human Body
Fatty acid
Percentage
Oleic acid
50% (MUFA)
Palmitic acid
35% (SFA)
Lionleic acid
10% (PUFA)
Stearic acid
5% (SFA)
? Thus most abundant Fatty acids
present in human Lipids are:
?Oleic acid (50%)
?Palmitic acid(35%)
Ideal Requirement
Of Fatty Acids To Human Body
? It is ideal to consume ratio of:
?1 : 1 : 1
? SFA MUFA PUFAs
? respectively from the diet to maintain good
health.
? Naturally there is no single oil which has
all 3 types of fatty acids in ideal
proportion.
? Hence it is always advisable to mix a
combination of oils and consume.
Transportation Of Fatty Acids In
Human Body
? Bound form /Esterified
Forms Of Fatty acids are
Transported through
various Lipoproteins.
Fatty acids Transportation In body
? More than 90% of the fatty acids found in
plasma are in the form of Fatty acid esters.
? Fatty acids Esters/Esterifed form of Fatty
acids exist as:
? Triacylglycerol
? Cholesteryl esters
? Phospholipids
? Unesterified/Free Fatty acids (FFA)
are very less amount in body.
? Long Chain FFA are transported in
the blood circulation in association
with Albumin.
Functions Of Fatty Acids
1. Secondary Source Of Energy
2. Components Of Biomembranes
3. PUFA (Arachidonic Acid) Precursor for Eicosanoid
Biosynthesis
4. Esterification of Cholesterol and its Excretion
5. PUFAs build and protect Brain and Heart
6. PUFAs prevents early ageing, prolongs Clotting
time.
? PUFAs of membrane play role
in:(Less compact)
?Membrane fluidity
?Selective permeability
Functions Of
PUFAS /Omega 3, and 6 FAs
? Components of cel biomembranes
? More associated to Human brain and Heart
? Involve in Growth ,development and
functioning of Brain
? Omega Fatty acids Reduces risk of Heart disease:
?Reduces Platelet aggregation by stimulating
Prostaglandins and Prostacyclin's .
?Reduces blood clotting and Thrombus
formation by Lowering the production of
Thromboxane .
? Omega 3 Fatty acids have pleiotropic effects
(more than on effect):
?Cardio protective effect
? Lowers Blood pressure
? Anti-Inflammatory
? Anti-Atherogenic
? Anti-Thrombotic
? PUFAs Lowers Risk Of Atherosclerosis
? Since double bonds of PUFAs are unstable and
easily cleavable.
? PUFAs get easily metabolized and do not get
accumulated in the blood arteries and capillaries.
? Thus PUFAs have low risk of Atherosclerosis and
Cardio vascular disorders.
? Fish (rich in Omega 3 Fatty acids) Eaters has
Healthy Brain and Heart
? Brain development with an efficient
nervous function.
? Protected from Heart attacks.
? Deficiency of Essential Fatty acids :
? Affects every cel ,organ and system
?Growth retardation
?Problems with reproduction
?Skin lesions
?Kidney and Liver disorders
?Brain disorders/Behavioral disorders.
Deficiency Of PUFAs/ Omega 3,6
Fatty acids
? Deficit of omega fatty acids affect the normal
growth ,development and functioning of brain.
? Persons may suffer from mental il ness like:
?Depression
?Attention deficit
?Dementia=Alzheimer's Disease
? Deficiency of Omega 3 Fatty acids :
?Alters the cell membrane structure.
?Increases the risk of
? Heart attack
? Cancer
? Rheumatoid Arthritis
Phrynoderma /Toad Skin is due
to PUFA deficiency.
? Phrynoderma /Toad Skin Symptoms
? The skin becomes dry with lesions
(Scaly Dermatitis).
? Presence of horny erruptions on the posterior and lateral
parts of limbs, back and Buttock.
? Loss of hair
? Poor wound healing
? Acanthosis and Hyperkeratosis
? Deficiency of PUFAs lower:
?Oxidative Phosphorylation-ATP generation
?Fibrinolytic Activities
Fatty Acids At Glance
Name of Biomolecule Fatty acids
Class
Derived Lipids
Structural Features
Organic acids ,Hydrocarbon Chain (C2-
26) Terminal Mono Carboxylic Acid
Sources of FAs to
From Exogenous and Endogenous
body
Distribution in Body FAs mostly in esterified form,
Associated with Simple and
Compound Lipids. Distributed in all
tissues.
Functional aspects
Energy, Biomembrane components
Interrelationships
Fatty acids associated to other form
of Simple and Compound Lipids
This post was last modified on 05 April 2022