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Polyunsaturated fatty acid

Polyunsaturated fatty acid

Overview
Polyunsaturated fatty acids (PUFA) are those that contain more than one double bond
Double bond
A double bond in chemistry is a chemical bond between two chemical elements involving four bonding electrons instead of the usual two. The most common double bond, that between two carbon atoms, can be found in alkenes. Many types of double bonds between two different elements exist, for example in...

.
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Encyclopedia
Polyunsaturated fatty acids (PUFA) are those that contain more than one double bond
Double bond
A double bond in chemistry is a chemical bond between two chemical elements involving four bonding electrons instead of the usual two. The most common double bond, that between two carbon atoms, can be found in alkenes. Many types of double bonds between two different elements exist, for example in...

.

Methylene-Interrupted Polyenes


These fatty acids have 2 or more cis double bond
Double bond
A double bond in chemistry is a chemical bond between two chemical elements involving four bonding electrons instead of the usual two. The most common double bond, that between two carbon atoms, can be found in alkenes. Many types of double bonds between two different elements exist, for example in...

s that are separated from each other by a single methylene
Methylene
Methylene is a chemical species in which a carbon atom is bonded to two hydrogen atoms. Three different possibilities present themselves:* the −CH2− group, e.g. dichloromethane...

 group. (This form is also sometimes called a divinylmethane pattern.)
Methylene- interrupted double bonds
-C-C=C-C-C=C-

The essential fatty acid
Essential fatty acid
Essential fatty acids, or EFAs, are fatty acids that cannot be constructed within an organism from other components by any known chemical pathways, and therefore must be obtained from the diet. The term refers to fatty acids involved in biological processes, and not those which may just play a...

s are all omega-3 and -6 methylene-interrupted fatty acids. See more at Essential fatty acids—Nomenclature

Omega-3

Common name Lipid name Chemical name
align=center| Omega-3 fatty acid
Omega-3 fatty acid
n−3 fatty acids are a family of unsaturated fatty acids that have in common a final carbon–carbon double bond in the n−3 position; that is, the third bond from the methyl end of the fatty acid.Important nutritionally essential n−3 fatty acids are: α-linolenic acid , eicosapentaenoic acid...

s
16:3 (n-3) all-cis 7,10,13-hexadecatrienoic acid
Alpha-linolenic acid
Alpha-linolenic acid
α-Linolenic acid is an organic compound found in many common vegetable oils. Systematically, it is named all-cis-9,12,15-octadecatrienoic acid. In physiological literature, it is given the name 18:3 ....

 (ALA)
18:3 (n-3) all-cis-9,12,15-octadecatrienoic acid
Stearidonic acid
Stearidonic acid
Stearidonic acid is an ω-3 essential fatty acid, sometimes called moroctic acid. It is biosynthesized from alpha-linolenic acid by the enzyme delta-6-desaturase. Natural sources of this fatty acid are the seed oils of hemp, blackcurrant and echium, and the cyanobacterium spirulina....

 (STD)
18:4 (n-3) all-cis-6,9,12,15,-octadecatetraenoic acid
Eicosatrienoic acid (ETE) 20:3 (n-3) all-cis-11,14,17-eicosatrienoic acid
Eicosatetraenoic acid
Eicosatetraenoic acid
Eicosatetraenoic acid, ETA, designates any straight chain 20:4 fatty acid.Two isomers, both of them essential fatty acids, are of particular interest:* all-cis 5,8,11,14-eicosatetraenoic acid is an ω-6 fatty acid with the trivial name arachidonic acid...

 (ETA)
20:4 (n-3) all-cis-8,11,14,17-eicosatetraenoic acid
Eicosapentaenoic acid
Eicosapentaenoic acid
Eicosapentaenoic acid is an omega-3 fatty acid. In physiological literature, it is given the name 20:5. It also has the trivial name timnodonic acid...

 (EPA)
20:5 (n-3) all-cis-5,8,11,14,17-eicosapentaenoic acid
Docosapentaenoic acid
Docosapentaenoic acid
Docosapentaenoic acid designates any straight chain 22:5 fatty acid.Two isomers are of particular interest* all-cis-7,10,13,16,19-docosapentaenoic acid is an ω-3 fatty acid with the trivial name clupanodonic acid, commonly called DPA. It is an intermediary between eicosapentaenoic acid and...

 (DPA, Clupanodonic acid)
22:5 (n-3) all-cis-7,10,13,16,19-docosapentaenoic acid
Docosahexaenoic acid
Docosahexaenoic acid
Docosahexaenoic acid is an omega-3 fatty acid. In chemical structure, DHA is a carboxylic acid with a 22-carbon chain and six cis double bonds; the first double bond is located at the third carbon from the omega end...

 (DHA)
22:6 (n-3) all-cis-4,7,10,13,16,19-docosahexaenoic acid
Tetracosapentaenoic acid 24:5 (n-3) all-cis-9,12,15,18,21-tetracosapentaenoic acid
Tetracosahexaenoic acid (Nisinic acid) 24:6 (n-3) all-cis-6,9,12,15,18,21-tetracosahexaenoic acid

Omega-6

Common name Lipid name Chemical name
align=center|Omega-6 fatty acid
Omega-6 fatty acid
n−6 fatty acids are a family of unsaturated fatty acids that have in common a final carbon–carbon double bond in the n−6 position, that is, the sixth bond from the end of the fatty acid.The biological effects of the n−6 fatty acids are largely mediated by their conversion to n-6 eicosanoids that...

s
Linoleic acid
Linoleic acid
Linoleic acid is an unsaturated omega-6 fatty acid. It is a colorless liquid. In physiological literature, it is called 18:2. Chemically, linoleic acid is a carboxylic acid with an 18-carbon chain and two cis double bonds; the first double bond is located at the sixth carbon from the omega...

18:2 (n-6) all-cis-9,12-octadecadienoic acid
Gamma-linolenic acid
Gamma-Linolenic acid
γ-Linolenic acid is a fatty acid found primarily in vegetable oils. It is sold as a dietary supplement for treating problems with inflammation and auto-immune diseases...

 (GLA)
18:3 (n-6) all-cis-6,9,12-octadecatrienoic acid
Eicosadienoic acid 20:2 (n-6) all-cis-11,14-eicosadienoic acid
Dihomo-gamma-linolenic acid
Dihomo-gamma-linolenic acid
Dihomo-γ-linolenic acid is a 20-carbon ω−6 fatty acid. In physiological literature, it is given the name 20:3 . Chemically, DGLA is a carboxylic acid with a 20-carbon chain and three cis double bonds; the first double bond is located at the sixth carbon from the omega end. DGLA is the...

 (DGLA)
20:3 (n-6) all-cis-8,11,14-eicosatrienoic acid
Arachidonic acid
Arachidonic acid
Arachidonic acid is an omega-6 fatty acid 20:4.It is the counterpart to the saturated arachidic acid found in peanut oil, Arachidonic acid (AA, sometimes ARA) is an omega-6 fatty acid 20:4(ω-6).It is the counterpart to the saturated arachidic acid found in peanut oil, Arachidonic acid (AA,...

 (AA)
20:4 (n-6) all-cis-5,8,11,14-eicosatetraenoic acid
Docosadienoic acid 22:2 (n-6) all-cis-13,16-docosadienoic acid
Adrenic acid
Docosatetraenoic acid
Docosatetraenoic acid designates any straight chain 22:4 fatty acid. One isomer is of particular interest:...

22:4 (n-6) all-cis-7,10,13,16-docosatetraenoic acid
Docosapentaenoic acid
Docosapentaenoic acid
Docosapentaenoic acid designates any straight chain 22:5 fatty acid.Two isomers are of particular interest* all-cis-7,10,13,16,19-docosapentaenoic acid is an ω-3 fatty acid with the trivial name clupanodonic acid, commonly called DPA. It is an intermediary between eicosapentaenoic acid and...

  (Osbond acid)
22:5 (n-6) all-cis-4,7,10,13,16-docosapentaenoic acid

Omega-9

Common name Lipid name Chemical name
align=center|Omega-9 fatty acid
Omega-9 fatty acid
Under severe conditions of EFA deprivation, mammals will elongate and desaturate oleic acid to make mead acid, . This also occurs to a lesser extent in vegetarians and semi-vegetarians.-Potential negative health effects:...

s, mono- and polysaturated
Oleic acid
Oleic acid
Oleic acid is a mono-unsaturated omega-9 fatty acid found in various animal and vegetable sources. It has the formula CH37CH=CH7COOH)...

18:1 (n-9) cis-9-octadecenoic acid
Eicosenoic acid
Eicosenoic acid
Eicosenoic acid is an monounsaturated omega-9 fatty acid found in a variety of plant oils....

20:1 (n-9) cis-11-eicosenoic acid
Mead acid
Mead acid
Mead acid is an omega-9 fatty acid, first characterized by James F. Mead. Like some other omega-9 polyunsaturated fatty acids animals can make Mead acid de novo. Its elevated presence in the blood is an indication of essential fatty acid deficiency....

20:3 (n-9) all-cis-5,8,11-eicosatrienoic acid
Erucic acid
Erucic acid
Erucic acid is a monounsaturated omega-9 fatty acid, denoted 22:1 ω-9. It is prevalent in rapeseed, wallflower seed, and mustard seed, making up 40-50% of their oils...

22:1 (n-9) cis-13-docosenoic acid
Nervonic acid
Nervonic acid
Nervonic acid is a monounsaturated omega-9 fatty acid. Nervonic acid has been identified as important in the biosynthesis of nerve cell myelin...

24:1 (n-9) cis-15-tetracosenoic acid
Monounsaturated
Monounsaturated fat
In biochemistry and nutrition, monounsaturated fats are fatty acids that have a single double bond in the fatty acid chain and all of the remainder of the carbon atoms in the chain are single-bonded...


Conjugated fatty acids


Conjugated double bonds
-C=C-C=C-

Common name Lipid name Chemical name
align=center|Conjugated fatty acid
Conjugated fatty acid
Conjugated fatty acids are polyunsaturated fatty acids in which at least one pair of double bonds are separated by only one single bond, as in conjugated linoleic acid:The conjugation results in delocalization of electrons along the system....

s  have two or more conjugated double bonds
Conjugated system
A conjugated system occurs in an organic compound where atoms covalently bond with alternating single and multiple bonds and influence each other to produce a region called electron delocalization. In this region electrons do not belong to a single bond or atom, but rather a group...

Conjugated Linoleic Acid
Conjugated linoleic acid
Conjugated linoleic acids are a family of at least 28 isomers of linoleic acid found especially in the meat and dairy products derived from ruminants. As the name implies, the double bonds of CLAs are conjugated.-History:...

s (two conjugated double bonds)
Rumenic acid
Rumenic acid
Rumenic acid, also known as bovinic acid, is a conjugated linoleic acid found in the fat of ruminants and in dairy products. It is an omega-7 trans fat. Its lipid shorthand name is cis-9, trans-11 18:2 acid....

18:2 (n-7) 9Z,11E-octadeca-9,11-dienoic acid
  18:2 (n-6) 10E,12Z-octadeca-9,11-dienoic acid
Conjugated Linolenic Acids (three conjugated double bonds)
α-Calendic acid
Calendic acid
Calendic acid is an unsaturated fatty acid, named for the pot marigold , from which it is obtained. It is chemically similar to the conjugated linoleic acids; laboratory work suggests it may have similar health benefits.-Biosynthesis:Calendic acid is an omega-6 fatty acid...

18:3 (n-6) 8E,10E,12Z-octadecatrienoic acid
β-Calendic acid
Calendic acid
Calendic acid is an unsaturated fatty acid, named for the pot marigold , from which it is obtained. It is chemically similar to the conjugated linoleic acids; laboratory work suggests it may have similar health benefits.-Biosynthesis:Calendic acid is an omega-6 fatty acid...

18:3 (n-6) 8E,10E,12E-octadecatrienoic acid
Jacaric acid
Jacaric acid
Jacaric acid is a conjugated polyunsaturated fatty acid. The melting point of this fatty acid is 44 °C. It occurs naturally in the seeds of the Jacaranda mimosifolia which contain about 36% jacaric acid....

18:3 (n-6) 8E,10Z,12E-octadecatrienoic acid
α-Eleostearic acid
Eleostearic acid
Eleostearic acid , sometimes called α-eleostearic acid, is a conjugated linolenic acid . It makes up approximately 80% of the fatty acids in tung oil and 60% of bitter gourd oil. Its high degree of unsaturation gives tung oil its properties as a drying oil...

18:3 (n-5) 9Z,11E,13E-octadeca-9,11,13-trienoic acid
β-Eleostearic acid
Eleostearic acid
Eleostearic acid , sometimes called α-eleostearic acid, is a conjugated linolenic acid . It makes up approximately 80% of the fatty acids in tung oil and 60% of bitter gourd oil. Its high degree of unsaturation gives tung oil its properties as a drying oil...

18:3 (n-5) 9E,11E,13E-octadeca-9,11,13-trienoic acid
Catalpic acid
Catalpic acid
Catalpic acid is a conjugated polyunsaturated fatty acid. The melting point of this fatty acid is 32 °C. Catalpic acid occurs naturally in the seeds of Catalpa ovata and Southern Catalpa . Seeds of Catalpa species contain about 40% catalpic acid....

18:3 (n-5) 9Z,11Z,13E-octadeca-9,11,13-trienoic acid
Punicic acid
Punicic acid
Punicic acid is a polyunsaturated fatty acid, 18:3 . It is named for the pomegranate, , and is obtained from pomegranate seed oil....

18:3 (n-5) 9Z,11E,13Z-octadeca-9,11,13-trienoic acid
Other
Rumelenic acid 18:3 (n-3) 9E,11Z,15E-octadeca-9,11,15-trienoic acid
α-Parinaric acid 18:4 (n-3) 9E,11Z,13Z,15E-octadeca-9,11,13,15-trienoic acid
β-Parinaric acid 18:4 (n-3) all trans-octadeca-9,11,13,15-trienoic acid
Bosseopentaenoic acid
Bosseopentaenoic acid
Bosseopentaenoic acid is a conjugated polyunsaturated fatty acid. Bosseopentaenoic acid can extract from the red coralline algae, Bossiella orbigniana....

20:5 (n-6) 5Z,8Z,10E,12E,14Z-eicosanoic acid

Other Polyunsaturates

Common name Lipid name Chemical name
Pinolenic acid
Pinolenic acid
Pinolenic acid is a fatty acid contained in the Korean Pine nut and the seeds of other conifers . The highest percentage of pinolenic acid is found in Siberian pine nuts and the oil produced by them....

18:3 (n-6) (5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid
Podocarpic acid 20:3 (n-6) (5Z,11Z,14Z)-eicosa-5,11,14-trienoic acid

Function and effects


The biological effects of the ω-3 and ω-6 fatty acids are largely mediated by their mutual interactions, see Essential fatty acid interactions
Essential fatty acid interactions
The actions of the ω-3 and ω-6 essential fatty acids are best characterized by their interactions; they cannot be understood separately.Arachidonic acid is a 20-carbon ω-6 essential fatty acid...

 for detail.

See also

  • Fatty acid
    Fatty acid
    In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail , which is either saturated or unsaturated...

  • Essential fatty acid
    Essential fatty acid
    Essential fatty acids, or EFAs, are fatty acids that cannot be constructed within an organism from other components by any known chemical pathways, and therefore must be obtained from the diet. The term refers to fatty acids involved in biological processes, and not those which may just play a...

  • Unsaturated fat
    Unsaturated fat
    An unsaturated fat is a fat or fatty acid in which there are one or more double bonds in the fatty acid chain. A fat molecule is monounsaturated if it contains one double bond, and polyunsaturated if it contains more than one double bond. Where double bonds are formed, hydrogen atoms are...

  • Monounsaturated fat
    Monounsaturated fat
    In biochemistry and nutrition, monounsaturated fats are fatty acids that have a single double bond in the fatty acid chain and all of the remainder of the carbon atoms in the chain are single-bonded...

  • Polyunsaturated fat
    Polyunsaturated fat
    In nutrition, polyunsaturated fat, or polyunsaturated fatty acid, are fatty acids in which more than one double bond exists within the representative molecule. That is, the molecule has two or more points on its structure capable of supporting hydrogen atoms not currently part of the structure...

  • Saturated fat
    Saturated fat
    Saturated fat is fat that consists of triglycerides containing only saturated fatty acid radicals. There are several kinds of naturally occurring saturated fatty acids, which differ by the number of carbon atoms, ranging from 3 carbons to 36...