Polyunsaturated fatty acid

Polyunsaturated fatty acid
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Polyunsaturated_fatty_acid".

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

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1 Methylene-Interrupted Polyenes
2 Conjugated fatty acids
3 Other Polyunsaturates
4 Function and effects
5 See also
6 References
- 6.1 Citations
- 6.2 General References

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

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

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

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

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)	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.

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" (PDF). Retrieved on 2007-01-17.

Adlof, R. O. and Gunstone, F. D. (2003-09-17). "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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