Class- Derived Lipids
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BASIC COMPONENTOF LIPID FORMS
What are Fatty Acids?
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Fatty Acids Are Derived Lipids? Fatty acids are of Class Derived Lipids:
?Since Fatty acids are Hydrolytic
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products of Simple and Compound
Lipids.
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Fatty Acids (FA)? Fatty Acids (FA) are relatively or
potential y related to various Lipid
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structures.
?Simple Lipids
?Compound Lipids
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?Derivatives of LipidsStructure And Chemical Nature
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Of Fatty AcidsChemical Structure Of Fatty Acids
Fatty acid Structures Has
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Varied Hydrocarbon Chains? The Hydrocarbon chain of
each Fatty acid is of varying
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chain length (C2 - C26).
Human Body Fatty Acid From C2-C26
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S.No Fatty Acid Name Fatty Acid Structure hasCarbon atoms
1
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Acetic Acid
C2
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2Propionic Acid
C3
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3
Butyric Acid
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C44
Valeric Acid
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C5
5
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PalmiticC16
6
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Stearic
C18
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7Oleic
C18
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S.NoFatty Acid Name
Fatty Acid Structure
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8
Linoleic Acid
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C189
Arachidic Acid
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C20
10
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Arachidonic AcidC20
11
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Behenic acid
C22
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12Lignoceric acid
C24
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13
Cerotic acid
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C26? Fatty acid structure have two
ends:
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? Carboxylic group(-COOH) at one end (Delta end
denoted as /Alpha end )
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? Methyl group (-CH3) at another end (Omegaend denoted as )
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Carboxylic Acid Functional Group OfFatty Acid
Definition of Fatty acids
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Fatty Acids are Defined as:? Fatty acids are chemical y Organic acids
? With Aliphatic Hydrocarbon chain (of varying
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length C2 to C26) with Mono terminal
Carboxylic acid group as functional group.
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Different Forms Of
Fatty acids In Body
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Free Fatty acid /Unesterified Fatty acid? Fatty acid who has free Carboxylic group
? Fatty acid not reacted and linked to an
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Alcohol by an Ester bond.
Esterified Fatty acid/Bound form of Fatty Acid
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?Fatty acid has no free Carboxylicgroup
?Fatty acid is linked to an Alcohol
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with an Ester bond.
Classification of Fatty acids
Biomedical y Important Fatty Acids
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Based On Six Different Modes:
? Classification of FAs Based on Six Modes:
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1. Total number of Carbon atoms in a Fatty acid structure2. Hydrocarbon chain length of Fatty acid
3. Bonds present in Fatty acid
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4. Nutritional requirement of Fatty acid
5. Chemical Nature and Structure of Fatty acids
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6. Geometric Isomerism of UFAsFatty acids Based on
Total Number of Carbon atoms
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?Even numbered Carbon Atom Fattyacids (2,4,6,8,16,18,20 etc)
?Odd numbered Carbon Atom Fatty
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acids (3,5,7,---)
? Most natural y occurring /human body Fatty
acids are even carbon numbered FAs.
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? Since biosynthesis of Fatty acids uses 2
Carbon units Acetyl-CoA (C2).
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? Examples of Even Carbon Numbered
Fatty acids:
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? Butyric Acid (C4)? Palmitic Acid (C16)
? Stearic Acid (C18)
? Oleic Acid (C18) (Most Common)
? Linoleic acid (C18)
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? Linolenic Acid (C18)? Arachidic acid (C20)
? Arachidonic acid (C20)
? Odd Carbon numbered Fatty acids are less related to
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human body? Example of Odd carbon Fatty acid associated to
human body
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?Propionic Acid ( 3C)
Fatty acids Based on
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Nature and Number of Bonds present? Saturated Fatty acids(SFAs)
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? Fatty acids having single bonds in hydrocarbon
chain structure.
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? Examples:? Acetic acid (C2)
? Butyric acid (C4)
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? Palmitic acid (C16)
? Stearic acid (C18)
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? Arachidic acid(C20)? Unsaturated Fatty acids (UFAs)
? Fatty acids having double bonds in its structure.
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? Types of UFAs:
? Monounsaturated Fatty acids (MUFAs)
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? Polyunsaturated Fatty acids (PUFAs)? Human body have no Enzyme system to introduce
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double bond beyond Carbon atom 10 in thehydrocarbon chain.
? Hence PUFAs are not biosynthesized
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in human beings.? Monounsaturated Fatty Acids(MUFAs):
? MUFAs have one double bond in a fatty acid structure
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? Examples of MUFAs :? Palmitoleic acid (C16:1;9) (7)
? Oleic acid (C18:1;9)(9)
? Erucic acid (C22:1;9)(9)
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? Poly Unsaturated Fatty Acids (PUFAs):
? UFAs with two or more double bonds in
the structure are termed as PUFAs.
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? Examples Of PUFAS:
? Linoleic(18:2;9,12) (6)
? Linolenic(18:3;9,12,15) (3)
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? 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)
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? Remember Unsaturated Fatty acids? Double bonds are:
? Weaker /unstable bonds.
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? Get easily cleavable/metabolized
?More the degree of Unsaturation in Fatty
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acids.?More is the unstability of Fatty acids.
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? Saturated Fatty acids structures areStraight.
? Unsaturated Fatty acids structures are
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bent (Kink).
? Saturated FAs: with straight structures are
tightly packed together.
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? Unsaturated FAs: with bent structures are
not compact and has no tight packing.
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? More the degree of unsaturation inFA/More double bonds in FA
structure
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? More is the bent of Fatty acid
structure.
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Fatty acids Based on the Nutritional
Requirement
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Nutritionally Essential Fattyacids
?Nutritional y Essential Fatty acids:
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?Fatty acids not biosynthesized in
human body and indispensable
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through nutrition/diet are termed asEssential Fatty acids.
?PUFAS are nutritional y essential
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Fatty acids.
Examples of Essential Fatty Acids/PUFAs:
?Linoleic
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?Linolenic
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?Arachidonic acids?Timnodonic and
?Cervonic
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Nutritional y Non Essential Fatty acids
? Nutritional y Non essential Fatty acids:
? Fatty acids which are biosynthesized in the body
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and are nutritional y non essential Fatty acids.
? Saturated Fatty acids and MUFAs are non essential
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Fatty acids.Examples Of Non Essential Fatty Acids
? Palmitic
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? Stearic? Oleic acid
Based on Geometric Isomerism of
Unsaturated Fatty acids
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? Cis Fatty Acids:
The Groups around double bond of Unsaturated FAs
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are on same side.? Examples:
? Cis Oleic acid (rich in Olive oil)
? Palmitoleic acid
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? Trans Fatty Acids :
? The groups around double bond of UFAs are on
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opposite side
? Example :
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? Elaidic acid /Trans Oleic acid (HydrogenatedFats )
Types Of Fatty acids Based on
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Hydrocarbon chain length? Short Chain Fatty acids (2-6 Hydrocarbon Chain length)
? Examples:
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? Acetic acid (C2)
? Propionic acid (C3)
? Butyric acid (C4)
? Valeric acid (C5)
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? Caproic acid (C6)? Medium Chain Fatty acids (8-14 Carbon length)
? Examples:
? Caprylic acid (C8)
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? Capric acid (C10)? Lauric acid (C12)
? Myristic acid (C14)
? Long Chain Fatty acids ( 16-20 Carbon length)
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? Examples:? Palmitic acid (C16)
? Palmitoleic acid (C16)
? Stearic acid (C18 )
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? Oleic acid (C18)? Linoleic acid (C18)
? Linolenic acid (C18)
? Arichidic acid (C20)
? Arachidonic acid /ETA(C20)
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? Timnodonic acid/EPA (C20)? Very Long Chain Fatty Acids (C22 onwards )
? Examples:
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? Behenic acid/Docosanoic (C22)? Erucic acid/Docosa 13 Enoic (C22)
? Clupanodonic/Docosapentaenoic acid (DPA) (C22)
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? Cervonic acid/DocosaHexaenoic (DHA) (C22)
? Lignoceric acid /Tetracosanoic (C24)
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? Nervonic /Tetracosaenoic (C24)? Cerotic acid/Hexacosanoic (C26)
Fatty acids Based on
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Chemical Nature and Structure
?Aliphatic Fatty acids:
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Straight Hydrocarbon chain
? Examples:
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?Palmitic acid (C16)?Stearic acid (C18)
? Branched Chain Fatty acids:
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? Possess Branched chains? Examples:
?Isovaleric (C5)
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?Phytanic acid (Butter , dairy products)
? Cyclic Fatty acids :
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? Contains Ring structure
? Examples:
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? Chaulmoogric acid(Used for Leprosy treatment in olden days)
? Hydnocarpic acid
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? Hydroxy Fatty acids:
? Contain Hydroxyl Groups
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? Examples:? Cerebronic acid (C24)/
2-HydroxyTetracosanoic acid
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? Ricinoleic acid(C18) (Castor oil)
Naming And Numbering
Of Fatty Acids
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? Every Fatty acids has a:
? Common Name
? Systematic Name
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? Most of the Fatty acids are known by their
common names.(Since easy to use)
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? Systematic names of Fatty acids are limited
in use. (Since not easy to use)
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Remember? Long chain Fatty acids are
also termed as Acyl chains.
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vThe systematic names of Saturated Fattyacids are named by adding suffix `anoic'.
v Example : Palmitic acid- C16/ Hexadecanoic
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acid
? The systematic names of Unsaturated Fatty
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acids are named by suffix `enoic'.? Example: Oleic acid- C18/ Octadecaenoic
acid
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S.N Common Name Systematic Name1
Palmitic Acid
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Hexadecanoic Acid
2
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Stearic AcidOctadecanoic Acid
3
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Oleic acid
Octadecaenoic acid
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4Linoleic Acid
Octadecadienoic acid
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5
Linolenic Acid
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Octadecatrienoic acid6
Arachidonic acid Eicosatetraenoic acid
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Numbering Of Fatty Acids
? Numbering of Carbon atoms of
Fatty acids is done from :
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?Both ends of Fatty acids-
? end/ end
? end
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Numbering Of Fatty acid From
Carboxyl/ end ( end)
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? From Carboxyl Group end( end ) :? Carboxylic acid group of Fatty acid is
numbered as C1
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? C2 is next adjacent Carbon atom ,? C3 and so onn..........
? Carbon atom is next to the functional
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group ?COOH of a Fatty acid.
? Next to Carbon is , , , and so onn.
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? Carbon atoms from Methyl(?CH3)group /non polar end() of a fatty
acid are numbered as 1,2,3
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and so onn.
Nomenclature Of Fatty
acids
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? FA Nomenclature is Based On
? Chain length/Total Number of Carbon atoms in a FA.
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? Count Number of Carbon atoms in FA? Number and Position of Double bonds
? Position of double bond from Carboxyl/Delta end
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? Position of double bond from Methyl/Omega
Short Hand Representations
of Fatty acids
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? Short Hand Representations
of Fatty acids:
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?Palmitic Acid (16:0)?Palmitoleic acid (16:1;9)
?\
? First digit stands for total number of carbon atoms
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in the fatty acid.
? Second digit designates number of double bonds.
? Third digit onwards indicates the position of
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double bonds.
Fatty-acid Nomenclature
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? Named according to chain length
? C18
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Fatty-acid Nomenclature? Named according to the number of
double bonds
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? C18:0
Common name:
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Fatty-acid Nomenclature? Named according to the number of
double bonds
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? C18:1
Common name:
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Oleic acidFatty-acid Nomenclature
? Named according to the number of
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double bonds
? C18:2
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Common name:Linoleic acid
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Fatty-acid Nomenclature? Named according to the number of
double bonds
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? C18:3
Common name:
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Linolenic acidOmega System Nomenclature
? Named according to the
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location of the first double bond from the non-carboxyl Methyl
end (count from the Methyl end /Omega end )
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Omega Fatty-acid Nomenclature
Omega 9 or n?9 fatty acid
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Omega 6 or n?6 fatty acidOmega 3 or n?3 fatty acid
?Stearic acid (18:0)
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?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 :
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? Linoleic acid (18C;9,12)? Linolenic acid (18C;9,12,15)
? indicates from COOH end.
? 9,12,15 are double bond positions from delta
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end.Short Hand Presentation of FA
14:0 Myristic acid
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16:0 Palmitic acid18:0 Stearic acid
18:1 cis D9 Oleic acid (9)
18:2 cisD9,12 Linoleic acid (6)
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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 )
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22:5 CisD7,10,13,16,19 Docosapentaenoic acid (3 )
Important Properties Of Fatty Acids
Properties Of Fatty Acids
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? Physical Properties
? Chemical Reactions
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Physical Properties Of Fatty Acids
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1. Solubility2. Melting Point
Solubility Of Fatty Acids Depends
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UponFactors Responsible For Solubility Of
Fatty Acids
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1. Hydrocarbon chain length2. Degree of Unsaturation- Number of Double Bonds
3. Hydrophobicity/Polarity of Fatty acids
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4. Polarity of Solvents
? Smal hydrocarbon chain length are less
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hydrophobic and more soluble? Long Chain FA and VLCFA more hydrophobic are
very less soluble
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? Solubility of Fatty acids decreases with increase in
Fatty acid hydrocarbon chain length.
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? Double bonds increases solubilityMelting Point of Fatty Acids
Factors Responsible For
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Melting Points Of Fatty Acids1. Hydrocarbon chain length
2. Nature of Bonds
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3. Degree of Unsaturation/Number of double bonds
Fatty Acids With
Decreased Melting Points
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? Short and Unsaturated Fatty
acids has low melting point
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? More degree of unsaturation lowis melting point of FAS
Melting Points
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? Affected by chain length
?Longer chain = higher melting temp
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Fatty acid: C12:0C14:0
C16:0
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C18:0
C20:0
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Melting point: 44?C58?C
63?C
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72?C
77?C
Melting Points
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? Affected by number of double bonds
?More saturated = higher melting temp
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Fatty acid:C18:0
C18:1
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C18:2
C18:3
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Melting point:72?C
16?C
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?5?C
?11?C
Fatty Acids With
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Increased Melting Points
? Long and Saturated Fatty acids are
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has high melting point.? Less degree of Unsaturation more is
melting point of Fatty acids
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? Thus melting point of Fatty acids(FAs):
?Increases with increase in chain
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length of FAs.?Decreases with decrease in chain
length of FAs.
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?Increases with low unsaturation of
FAs
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?Decreases with more unsaturation ofFatty acids
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Structures and Melting Points of Saturated Fatty AcidsChemical Reactions Of Fatty Acids
Types Of Chemical Reactions
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Of Fatty acidsReactions due to
Carboxyl group of Fatty acids:
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? Esterification/Esterified forms of Lipids
? Saponification/Soap Formation
Reactions Associated to
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Double bonds of Fatty acids:
? Halogenation/Addition of Halogens around double
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bond? Hydrogenation/Transform to UFAs to SFAs
Significance Of Halogenation
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?Halogenation of fatty
acids is an index of
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assessing the degree ofunsaturation
? Iodine Number is a process of
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Halogenation which checks thecontent of SFA and PUFAs of Fats
and Oils.
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? SFA has zero Iodine number.
? PUFAs has high Iodine number.
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Hydrogenation Of Fatty acidsAlters Geometric Isomerism Of
Unsaturated Fatty acids
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Transforms Natural Cis Form to Trans Form
Increases Shelf life of PUFAs
Al -Cis Fatty acids
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Good for Health
? Human body contain Enzyme system to
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metabolize Cis form of Fatty acids.? Cis forms when ingested through food are
easily metabolized and does not retain in the
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body.
? Hence All ?Cis forms are good for health and no
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risk of Atherosclerosis and CVD.? Al Cis form of fatty acids are unstable and
easily metabolizable.
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? More content of Trans Fatty acids are found
in processed/Refined foods viz:
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?Hydrogenated Oils (Vanaspati Dalda)?Ghee
?Margarine
?Bakery products /Fast foods
?Deeply Fried recipes in Oils which are
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prepared in repeatedly heated oils.
? Trans fatty acids increases risk of
:
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?Atherosclerosis
?Cardio Vascular disorders:
?Ischemia
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?Myocardial Infarction?Stroke(Brain attack)
Message
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Learnt, Understood And To Be Implemented
For Good Fatty acid metabolism and Significant Health
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? Eat natural Cis forms of Fatty acids? Avoid Hydrogenated Trans Fatty
acids
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? Eat home made food? Avoid Processed/Junk Foods
PUFAs And Omega Fatty Acids
Types Of Omega Fatty acids
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?In Nutrition and Clinical
practice
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?3 Fatty acids?6 Fatty acids
?7 Fatty acids
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?9 Fatty acids
Omega Fatty Acids
Omega 3 Fas
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Omega 6 Fas
Omega 7 Fas
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Omega 9 FasPUFAs
PUFAs
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MUFAs
MUFAs
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LinolenicLinoleic
Palmitoleic Oleic ?
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C18-(ODTA)
C18- (ODDA) C16-(HDA) C18(ODA)
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TimnodonicErucic ?
C20-(EPA)
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Arachidonic
C22(DA)
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CervonicC20-(ETA)
Nervonic
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C22-(DHA)
C24-(TA)
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ClupanodonicC22-(DPA)
Examples of 3 Fatty acids
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? Linolenic (18:3;9,12,15) (3)
? Timnodonic/Ecosapentaenoic Acid /EPA
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(20:5;5,8,11,14,17)(3)? Clupanodonic acid/(Docosa Pentaenoic Acid): (DPA)
(C22:5;7,10,13,16,19 )(3)
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? Cervonic/Docosa Hexaenoic Acid
(DHA)(22:6;4,7,10,13,16,19)(3)
Rich sources of dietary Omega and nutritional
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essential PUFAS are:
?Vegetable Oils
?Green Leaves, Algae
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?Fish and Fish oils?Flax Seeds
Sources,Distribution,Composition Of
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Fatty Acids In Human BodySources Of Fatty Acids To Human Body
? Exogenous Sources- Dietary Food Items
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? Endogenous Biosynthesis- From Free ExcessGlucose in Liver
Forms of Dietary Fatty Acids To Be Ingested
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Natural Forms Of Fatty Acids? Fatty acids in nature mostly presently in
? Esterified form of FAs? (TAG,PL,CE)
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? Even Numbered Carbon? Unsaturated- PUFAs/Omega 3 and 6
? Cis forms
Contents Of Fatty acids Sources Of Oils
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Highest Content of MUFA Olive Oil , Mustard OilHighest content of PUFA Safflower, Sunflower,
Flax seed Oil
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Highest content of SFA
Coconut Oil
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Oils Rich InOils rich in
Oils rich in
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SFAs
MUFAs
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PUFAsCoconut Oil
Olive Oil (75%)
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Flax seeds/
Linseed Oil
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Palm OilSunflower Oil (85%)
Soya /Safflower Oil
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Butter
Ground nut /
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Almond OilPea nut Oil
Animal Fat
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Almond Oil
Rice Bran
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Sesame OilWalnuts Oil
Beef Fat (Tal ow Fat) 50%
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Corn Oil
Lard (Pork Fat) 40%
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Marine FishCarbons
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Double bonds
Abbreviation
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SourceFatty Acids
Acetic
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2
0
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2:0bacterial metabolism
Propionic
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3
0
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3:0bacterial metabolism
Butyric
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4
0
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4:0butterfat
Caproic
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6
0
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6:0butterfat
Caprylic
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8
0
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8:0coconut oil
Capric
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10
0
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10:0coconut oil
Lauric
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12
0
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12:0coconut oil
Myristic
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14
0
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14:0palm kernel oil
Palmitic
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16
0
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16:0palm oil
Palmitoleic
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16
1
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16:1animal fats
Stearic
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18
0
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18:0animal fats
Oleic
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18
1
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18:1olive oil
Linoleic
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18
2
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18:2grape seed oil
Linolenic
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18
3
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18:3flaxseed (linseed) oil
Arachidonic
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20
4
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20:4peanut oil, fish oil
Fatty acid Composition
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of Human BodyFatty acid
Percentage
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Oleic acid
50% (MUFA)
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Palmitic acid35% (SFA)
Lionleic acid
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10% (PUFA)
Stearic acid
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5% (SFA)? Thus most abundant Fatty acids
present in human Lipids are:
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?Oleic acid (50%)
?Palmitic acid(35%)
Ideal Requirement
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Of Fatty Acids To Human Body? It is ideal to consume ratio of:
?1 : 1 : 1
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? SFA MUFA PUFAs
? respectively from the diet to maintain good
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health.? Naturally there is no single oil which has
all 3 types of fatty acids in ideal
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proportion.? Hence it is always advisable to mix a
combination of oils and consume.
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Transportation Of Fatty Acids In
Human Body
? Bound form /Esterified
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Forms Of Fatty acids are
Transported through
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various Lipoproteins.Fatty acids Transportation In body
? More than 90% of the fatty acids found in
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plasma are in the form of Fatty acid esters.
? Fatty acids Esters/Esterifed form of Fatty
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acids exist as:? Triacylglycerol
? Cholesteryl esters
? Phospholipids
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? Unesterified/Free Fatty acids (FFA)are very less amount in body.
? Long Chain FFA are transported in
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the blood circulation in association
with Albumin.
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Functions Of Fatty Acids1. Secondary Source Of Energy
2. Components Of Biomembranes
3. PUFA (Arachidonic Acid) Precursor for Eicosanoid
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Biosynthesis
4. Esterification of Cholesterol and its Excretion
5. PUFAs build and protect Brain and Heart
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6. PUFAs prevents early ageing, prolongs Clottingtime.
? PUFAs of membrane play role
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in:(Less compact)?Membrane fluidity
?Selective permeability
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Functions OfPUFAS /Omega 3, and 6 FAs
? Components of cel biomembranes
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? More associated to Human brain and Heart
? Involve in Growth ,development and
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functioning of Brain? Omega Fatty acids Reduces risk of Heart disease:
?Reduces Platelet aggregation by stimulating
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Prostaglandins and Prostacyclin's .?Reduces blood clotting and Thrombus
formation by Lowering the production of
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Thromboxane .
? Omega 3 Fatty acids have pleiotropic effects
(more than on effect):
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?Cardio protective effect
? Lowers Blood pressure
? Anti-Inflammatory
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? Anti-Atherogenic? Anti-Thrombotic
? PUFAs Lowers Risk Of Atherosclerosis
? Since double bonds of PUFAs are unstable and
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easily cleavable.
? PUFAs get easily metabolized and do not get
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accumulated in the blood arteries and capillaries.? Thus PUFAs have low risk of Atherosclerosis and
Cardio vascular disorders.
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? Fish (rich in Omega 3 Fatty acids) Eaters has
Healthy Brain and Heart
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? Brain development with an efficientnervous function.
? Protected from Heart attacks.
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? Deficiency of Essential Fatty acids :? Affects every cel ,organ and system
?Growth retardation
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?Problems with reproduction?Skin lesions
?Kidney and Liver disorders
?Brain disorders/Behavioral disorders.
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Deficiency Of PUFAs/ Omega 3,6Fatty acids
? Deficit of omega fatty acids affect the normal
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growth ,development and functioning of brain.
? Persons may suffer from mental il ness like:
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?Depression?Attention deficit
?Dementia=Alzheimer's Disease
? Deficiency of Omega 3 Fatty acids :
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?Alters the cell membrane structure.?Increases the risk of
? Heart attack
? Cancer
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? Rheumatoid ArthritisPhrynoderma /Toad Skin is due
to PUFA deficiency.
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? Phrynoderma /Toad Skin Symptoms? The skin becomes dry with lesions
(Scaly Dermatitis).
? Presence of horny erruptions on the posterior and lateral
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parts of limbs, back and Buttock.
? Loss of hair
? Poor wound healing
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? Acanthosis and Hyperkeratosis? Deficiency of PUFAs lower:
?Oxidative Phosphorylation-ATP generation
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?Fibrinolytic Activities
Fatty Acids At Glance
Name of Biomolecule Fatty acids
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Class
Derived Lipids
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Structural FeaturesOrganic acids ,Hydrocarbon Chain (C2-
26) Terminal Mono Carboxylic Acid
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Sources of FAs to
From Exogenous and Endogenous
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bodyDistribution in Body FAs mostly in esterified form,
Associated with Simple and
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Compound Lipids. Distributed in alltissues.
Functional aspects
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Energy, Biomembrane components
Interrelationships
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Fatty acids associated to other formof Simple and Compound Lipids