Polyunsaturated fatty acid

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Polyunsaturated fatty acids (PUFA) are those which contain more than one double bond.

Contents

[edit] Methylene-Interrupted Polyenes

These fatty acids have 2 or more cis double bonds which are separated from each other by a single methylene group. (This form is also sometimes called a divinylmethane pattern.) [1]

Methylene- interrupted double bonds
-C-C=C-C-C=C-

The essential fatty acids comprise the omega-3 and -6 methylene-interrupted fatty acids. See more at Essential fatty acids—Nomenclature

[edit] Omega-3

Omega-3 fatty acids

Common name Lipid name Chemical name
16:3 (n-3) all-cis 7,10,13-hexadecatrienoic acid
Alpha-linolenic acid (ALA) 18:3 (n-3) all-cis-9,12,15-octadecatrienoic acid
Stearidonic acid (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 (ETA) 20:4 (n-3) all-cis-8,11,14,17-eicosatetraenoic acid
Eicosapentaenoic acid (EPA) 20:5 (n-3) all-cis-5,8,11,14,17-eicosapentaenoic acid
Docosapentaenoic acid (DPA, Clupanodonic acid) 22:5 (n-3) all-cis-7,10,13,16,19-docosapentaenoic acid
Docosahexaenoic acid (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

[edit] Omega-6

Omega-6 fatty acids

Common name Lipid name Chemical name
Linoleic acid 18:2 (n-6) all-cis-9,12-octadecadienoic acid
Gamma-linolenic acid (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 (DGLA) 20:3 (n-6) all-cis-8,11,14-eicosatrienoic acid
Arachidonic acid (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 22:4 (n-6) all-cis-7,10,13,16-docosatetraenoic acid
Docosapentaenoic acid (Osbond acid) 22:5 (n-6) all-cis-4,7,10,13,16-docosapentaenoic acid

[edit] Omega-9

Omega-9 fatty acids, mono- and polysaturated

Common name Lipid name Chemical name
Oleic acid† 18:1 (n-9) cis-9-octadecenoic acid
Eicosenoic acid† 20:1 (n-9) cis-11-eicosenoic acid
Mead acid 20:3 (n-9) all-cis-5,8,11-eicosatrienoic acid
Erucic acid† 22:1 (n-9) cis-13-docosenoic acid
Nervonic acid† 24:1 (n-9) cis-15-tetracosenoic acid
†Monounsaturated

[edit] Conjugated fatty acids

 It has been suggested that Conjugated fatty acid be merged into this article or section. (Discuss)
Conjugated double bonds
-C=C-C=C-

Conjugated fatty acids have two or more conjugated double bonds

Common name Lipid name Chemical name
Conjugated Linoleic Acids (two conjugated double bonds)
Rumenic 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 18:3 (n-6) 8E,10E,12Z-octadecatrienoic acid
β-Calendic acid 18:3 (n-6) 8E,10E,12E-octadecatrienoic acid
Jacaric acid 18:3 (n-6) 8E,10Z,12E-octadecatrienoic acid
α-Eleostearic acid 18:3 (n-5) 9E,11E,13Z-octadeca-9,11,13-trienoic acid
β-Eleostearic acid 18:3 (n-5) 9E,11E,13E-octadeca-9,11,13-trienoic acid
Catalpic acid 18:3 (n-5) 9Z,11Z,13E-octadeca-9,11,13-trienoic acid
Punicic acid 18:3 (n-5) 9E,11Z,13E-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 20:5 (n-6) 5Z,8Z,10E,12E,14Z-eicosanoic acid

[edit] Other Polyunsaturates

Common name Lipid name Chemical name
Pinolenic acid 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

[edit] 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 for detail.

[edit] See also

[edit] References

[edit] Citations

  1. ^ Baggott, James (1997). The divinylmethane pattern in fatty acids. Salt Lake City, UT: Knowledge Weavers. 

[edit] General References

  • Heinz (1983). "Similarities and Differences in Lipid Metabolism of Chloroplasts Isolated from 18:3 and 16:3 Plants". Plant Physiol 72 (2): 273–279. PMID 16662992.