Polyunsaturated fatty acid
Oxford Food & Nutrition Dictionary:
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polyunsaturated fatty acids
Long-chain fatty acids containing two or more double bonds, separated by methylene bridges:
Oxford Dictionary of Biochemistry:
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polyunsaturated fatty acid
abbr.: PUFA; any fatty acid that is polyunsaturated; the multiple bonds are most frequently all ethylenic and usually methylene-interrupted, the configuration of their substituents generally being Z (i.e. cis); more rarely is an acetylenic bond present. In animal metabolism, polyunsaturated fatty acids belong to families denoted by the position of the double bond nearest to the methyl group and often also by the name of the fatty acid from which the remainder can be derived; hence linoleic family, linolenic family, oleic family, and palmitoleic family. In recent years, emphasis has been placed on a role of some polyunsaturated fatty acids in lowering plasma cholesterol, and potentially reducing the risk of heart disease. Foremost among these have been those of the n-6 family such as linoleic acid. A recommendation has been made that the diet should contain these polyunsaturated fats in a ratio of 2:1 to saturated fats. See also essential fatty acid, fatty-acid nomenclature, fish oil.
| polyunsaturated, polyubiquitin, polytrioxophosphate | |
| polyuria, polyuronide, polyvalent |
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Polyunsaturated fatty acid
Polyunsaturated fatty acids (PUFAs) are fatty acids that contain more than one double bond in their backbone. This class includes many important compounds, such as essential fatty acids and those that give drying oils their characteristic property.
Polyunsaturated fatty acids can be classified in various groups by their chemical structure:
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Contents
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Methylene-Interrupted Polyenes
These fatty acids have 2 or more cis double bonds that are separated from each other by a single methylene group. (This form is also sometimes called a divinylmethane pattern.) [1]
| -C-C=C-C-C=C- |
The essential fatty acids 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 |
|---|---|---|
| Hexadecatrienoic acid (HTA) | 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 (SDA) | 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, Timnodonic acid) | 20:5 (n-3) | all-cis-5,8,11,14,17-eicosapentaenoic acid |
| Heneicosapentaenoic acid (HPA) | 21:5 (n-3) | all-cis-6,9,12,15,18-heneicosapentaenoic acid |
| Docosapentaenoic acid (DPA, Clupanodonic acid) | 22:5 (n-3) | all-cis-7,10,13,16,19-docosapentaenoic acid |
| Docosahexaenoic acid (DHA, Cervonic acid) | 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 |
|---|---|---|
| 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 |
| Tetracosatetraenoic acid | 24:4 (n-6) | all-cis-9,12,15,18-tetracosatetraenoic acid |
| Tetracosapentaenoic acid | 24:5 (n-6) | all-cis-6,9,12,15,18-tetracosapentaenoic acid |
Omega-9
Omega-9 fatty acids, mono- and polyunsaturated
| 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 | ||
Conjugated fatty acids
| -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) | 9Z,11E,13E-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) | 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 | 20:5 (n-6) | 5Z,8Z,10E,12E,14Z-eicosanoic acid |
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 |
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
- Fatty acid
- Essential fatty acid
- Unsaturated fat
- Monounsaturated fat
- Polyunsaturated fat
- Saturated fat
References
Citations
- ^ Baggott, James (1997). The divinylmethane pattern in fatty acids. Salt Lake City, UT: Knowledge Weavers.
General References
- Cyberlipid. "Polyenoic Fatty Acids". http://www.cyberlipid.org/fa/acid0003.htm. Retrieved 2007-01-17.
- Gunstone, Frank D. "Lipid Glossary 2" (PDF). Archived from the original on 2006-08-13. http://web.archive.org/web/20060813111917/http://www.plantbiology.msu.edu/ohlrogge/labweb/lipid_glossary.pdf. Retrieved 2007-01-17.
- Adlof, R. O. and Gunstone, F. D. (2003-09-17). "Common (non-systematic) Names for Fatty Acids". Archived from the original on 2006-12-06. http://web.archive.org/web/20061206090944/http://www.aocs.org/member/division/analytic/fanames.asp. Retrieved 2007-01-24.
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Oxford Food & Nutrition Dictionary
A Dictionary of Food and Nutrition. Copyright © 1995, 2003, 2005 by A. E. Bender and D. A. Bender. All rights reserved.
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