Polyunsaturated fatty acid 3321981 225927205 2008-07-16T01:34:32Z Rjwilmsi 203434 gen fixes + link/fix date fields in cite templates (explanation [[User:Rjwilmsi#My_correction_of_citation_templates|here]]) using [[Project:AutoWikiBrowser|AWB]] '''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&mdash;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 &nbsp;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 |- | &nbsp; | 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]]