Polyunsaturated fatty acid
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'''Polyunsaturated [[fatty acids]]''' ('''PUFA''') are those which contain more than one [[double bond]].
== Methylene-Interrupted Polyenes ==
These fatty acids have 2 or more ''cis'' [[double bond]]s which are separated from each other by a single [[methylene]] group. (This form is also sometimes called a ''divinylmethane pattern''.) <ref name=baggott>
{{cite book
|author= Baggott, James|year= 1997|title= The divinylmethane pattern in fatty acids
|location= Salt Lake City, UT|publisher= Knowledge Weavers}}</ref>
{| class="wikitable" style="margin: 1em 0 1em 1em; float: right;"
|+ Methylene- interrupted double bonds
|-
| '''-C-C=C-C-C=C-'''
|-
|}
The [[essential fatty acid]]s comprise the omega-3 and -6 methylene-interrupted fatty acids. ''See more at [[Essential fatty acid#Nomenclature and terminology|Essential fatty acids—Nomenclature]]''
=== Omega-3 ===
{| class="wikitable"
! Common name
! Lipid name
! Chemical name
|+ align=center| [[Omega-3 fatty acid]]s
|-
|
| 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 ===
{| class="wikitable"
! Common name
! Lipid name
! Chemical name
|+ align=center|[[Omega-6 fatty acid]]s
|-
| [[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
|-
| [[Docosatetraenoic 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 ===
{| class="wikitable"
! Common name
! Lipid name
! Chemical name
|+ align=center|[[Omega-9 fatty acid]]s, mono- and polysaturated
|-
| [[Oleic acid]]<sup>†</sup>
| 18:1 (n-9)
| ''cis''-9-octadecenoic acid
|-
| [[Eicosenoic acid]]<sup>†</sup>
| 20:1 (n-9)
| ''cis''-11-eicosenoic acid
|-
| [[Mead acid]]
| 20:3 (n-9)
|''all-cis''-5,8,11-eicosatrienoic acid
|-
| [[Erucic acid]]<sup>†</sup>
| 22:1 (n-9)
|''cis''-13-docosenoic acid
|-
| [[Nervonic acid]]<sup>†</sup>
| 24:1 (n-9)
|''cis''-15-tetracosenoic acid
|-
| colspan=3|<small><sup>†</sup>[[Monounsaturated fat|Monounsaturated</small>]]
|}
== Conjugated fatty acids ==
{{Mergefrom|Conjugated fatty acid|date=December 2007}}
{| class="wikitable" style="margin: 1em 0 1em 1em; float: right;"
|+ Conjugated double bonds
|-
| '''-C=C-C=C-'''
|-
|}
{| class="wikitable"
! Common name
! Lipid name
! Chemical name
|+ align=center|[[Conjugated fatty acid]]s have two or more [[Conjugated system|conjugated double bonds]]
<!--|-
| [[Trans fat]]
| ''mixture of isomers''
| ''Mostly 18 carbons''-->
|-
| colspan=3 align=center | ''[[Conjugated Linoleic Acid]]s (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
|-
| colspan=3 align=center| ''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
|-
| colspan = 3 align=center|''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==
{| class="wikitable"
! 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===
<references />
===General References===
*{{cite web
| url=http://www.cyberlipid.org/fa/acid0003.htm
| title= Polyenoic Fatty Acids
| author=Cyberlipid| accessdate=2007-01-17}}
* {{cite web
|title=Lipid Glossary 2
|url=http://www.plantbiology.msu.edu/ohlrogge/labweb/lipid_glossary.pdf
|author=Gunstone, Frank D | accessdate=2007-01-17|format=PDF}}
*{{cite web
| url=http://aocs.org/member/division/analytic/fanames.asp
|author = Adlof, R. O. and Gunstone, F. D.|title=Common (non-systematic) Names for Fatty Acids|date= 2003-09-17 | accessdate=2007-01-24}}
*{{cite journal |author= Heinz|title=Similarities and Differences in Lipid Metabolism of Chloroplasts Isolated from 18:3 and 16:3 Plants |journal=Plant Physiol |volume=72 |issue=2 |pages=273–279 |year=1983 |pmid=16662992}}
[[Category:Fatty acids]]
[[Category:Chemical structures]]
[[Category:Nutrition]]
[[Category:Nutrients]]