Polyunsaturated fatty acid
The polyunsaturated fatty acids (PUFA) are fatty acids which contains more than one double bond.
Additional recommended knowledge
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-
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The essential fatty acids comprise the omega-3 and -6 methylene-interrupted fatty acids. See more at Essential fatty acids—Nomenclature
Omega-3
Common name
| Lipid name
| Chemical name
| Omega-3 fatty acids
| 16:3 (n-3)
| all-cis 7,10,13-hexadecatrienoic acid
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Alpha-linolenic acid (ALA)
| 18:3 (n-3)
| all-cis-9,12,15-octadecatrienoic acid
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Stearidonic acid
| 18:4 (n-3)
| all-cis-6,9,12,15,-octadecatetraenoic acid
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Eicosatetraenoic acid
| 20:4 (n-3)
| all-cis-8,11,14,17-eicosatetraenoic acid
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Eicosapentaenoic acid (EPA)
| 20:5 (n-3)
| all-cis-5,8,11,14,17-eicosapentaenoic acid
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Docosapentaenoic acid (DPA, Clupanodonic acid)
| 22:5 (n-3)
| all-cis-7,10,13,16,19-docosapentaenoic
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Docosahexaenoic acid (DHA)
| 22:6 (n-3)
| all-cis-4,7,10,13,16,19-docosahexaenoic acid
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| 24:5 (n-3)
| all-cis-4,7,10,13,16,19-docosahexaenoic acid
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Nisinic acid
| 24:6 (n-3)
| all-cis-6,9,12,15,18,21-tetracosenoic acid
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Omega-6
Common name
| Lipid name
| Chemical name
| Omega-6 fatty acids
Linoleic acid
| 18:2 (n-6)
| all-cis-9,12-octadecadienoic acid
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Gamma-linolenic acid (GLA)
| 18:3 (n-6)
| all-cis-6,9,12-octadecatrienoic acid
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Eicosadienoic acid
| 20:2 (n-6)
| all-cis-11,14-eicosadienoic acid
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Dihomo-gamma-linolenic acid (DGLA)
| 20:3 (n-6)
| all-cis-8,11,14-eicosatrienoic acid
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Arachidonic acid (AA)
| 20:4 (n-6)
| all-cis-5,8,11,14-eicosatetraenoic acid
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Docosadienoic acid
| 22:2 (n-6)
| all-cis-13,16-docosadienoic acid
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Adrenic acid
| 22:4 (n-6)
| all-cis-7,10,13,16-docosatetraenoic acid
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Docosapentaenoic acid (Osbond acid)
| 22:5 (n-6)
| all-cis-4,7,10,13,16-docosapentaenoic acid
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Omega-9
Common name
| Lipid name
| Chemical name
| Omega-9 fatty acids, mono- and polysaturated
Oleic acid†
| 18:1 (n-9)
| cis-9-octadecenoic acid
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Eicosenoic acid†
| 20:1 (n-9)
| cis-11-eicosenoic acid
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Mead acid
| 20:3 (n-9)
| all-cis-5,8,11-eicosatrienoic acid
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Erucic acid†
| 22:1 (n-9)
| cis-13-docosenoic acid
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Nervonic acid†
| 24:1 (n-9)
| cis-15-tetracosenoic acid
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†Monounsaturated
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Conjugated fatty acids
Conjugated double bonds
-C=C-C=C-
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Common name
| Lipid name
| Chemical name
| Conjugated fatty acids have two or more conjugated double bonds
Conjugated Linoleic Acids (two conjugated double bonds)
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Rumenic acid
| 18:2 (n-7)
| 9Z,11E-octadeca-9,11-dienoic acid
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| 18:2 (n-6)
| 10E,12Z-octadeca-9,11-dienoic acid
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Conjugated Linolenic Acids (three conjugated double bonds)
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α-Calendic acid
| 18:3 (n-6)
| 8E,10E,12Z-octadecatrienoic acid
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β-Calendic acid
| 18:3 (n-6)
| 8E,10E,12E-octadecatrienoic acid
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Jacaric acid
| 18:3 (n-6)
| 8E,10Z,12E-octadecatrienoic acid
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α-Eleostearic acid
| 18:3 (n-5)
| 9E,11E,13Z-octadeca-9,11,13-trienoic acid
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β-Eleostearic acid
| 18:3 (n-5)
| 9E,11E,13E-octadeca-9,11,13-trienoic acid
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Catalpic acid
| 18:3 (n-5)
| 9Z,11Z,13E-octadeca-9,11,13-trienoic acid
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Punicic acid
| 18:3 (n-5)
| 9E,11Z,13E-octadeca-9,11,13-trienoic acid
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Other
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Rumelenic acid
| 18:3 (n-3)
| 9E,11Z,15E-octadeca-9,11,15-trienoic acid
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α-Parinaric acid
| 18:4 (n-3)
| 9E,11Z,13Z,15E-octadeca-9,11,13,15-trienoic acid
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β-Parinaric acid
| 18:4 (n-3)
| all trans-octadeca-9,11,13,15-trienoic acid
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Bosseopentaenoic acid
| 20:5 (n-6)
| 5Z,8Z,10E,12E,14Z-eicosanoic acid
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Other Polyunsaturates
Common name
| Lipid name
| Chemical name
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Pinolenic acid
| 18:3 (n-6)
| (5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid
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Podocarpic acid
| 20:3 (n-6)
| (5Z,11Z,14Z)-eicosa-5,11,14-trienoic acid
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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.
See also
References
Citations
- ^
Baggott, James (1997). The divinylmethane pattern in fatty acids. Salt Lake City, UT: Knowledge Weavers.
General References
- Cyberlipid. Polyenoic Fatty Acids. Retrieved on 2007-01-17.
- Gunstone, Frank D. Lipid Glossary 2. Retrieved on 2007-01-17.
- Adlof, R. O. and Gunstone, F. D. (2003-9-17). Common (non-systematic) Names for Fatty Acids. Retrieved on 2007-01-24.
- 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.
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