Omega-9 fatty acid 3110439 224381298 2008-07-08T16:33:13Z 146.101.201.218 Removed annotation {{For2|an explanation of ''n'' and numerical nomenclature (such as ''n''−9 or 18:1)|[[Fatty acid#Nomenclature|Nomenclature of fatty acids]]}} {{Fats}} '''''n''−9 fatty acids''' (popularly referred to as '''ω−9 fatty acids''' or '''omega-9 fatty acids''') are a family of [[unsaturated fat|unsaturated]] [[fatty acid]]s which have in common a carbon–carbon [[double bond#Bond order|double bond]] in the [[essential fatty acid#Nomenclature and terminology|''n''−9]] position; that is, the ninth bond from the end of the fatty acid. ==Background== Some ''n''−9s are common components of [[animal fat]] and [[vegetable oil]]. Two ''n''−9 fatty acids important in industry are: * [[Oleic acid]] (18:1, ''n''−9), which is a main component of [[olive oil]] and other [[monounsaturated fat]]s * [[Erucic acid]] (22:1, ''n''−9), which is found in [[rapeseed]], [[wallflower]] seed, and [[mustard seed]]. Rapeseed with high erucic acid content is grown for commercial use in paintings and coatings as a [[drying oil]]. Unlike [[Omega-3 fatty acids|''n''−3]] and [[Omega-6 fatty acids|''n''−6]] fatty acids, ''n''−9 fatty acids are not classed as [[essential fatty acids]] (EFA). This is both because they can be created by the human body from [[unsaturated fat]], and are therefore not essential in the diet, and because the lack of an ''n''−6 double bond keeps them from participating in the reactions that form the [[eicosanoid]]s. Under severe conditions of EFA deprivation, mammals will elongate and desaturate oleic acid to make [[mead acid]], (20:3, ''n''−9).<ref name="lipomics">{{cite web|url=http://www.lipomics.com/resources/fatty_acids/20_3n9.htm |author=Lipomics|title = Mead acid| accessdate= February 14|accessyear = 2006}}</ref> This also occurs to a lesser extent in [[vegetarians]] and semi-vegetarians.<ref name="phinney1990">{{cite web| author=Phinney, SD, RS Odin, SB Johnson and RT Holman |title=Reduced arachidonate in serum phospholipids and cholesteryl esters associated with vegetarian diets in humans|url=http://intl.ajcn.org/cgi/content/abstract/51/3/385|accessdate=February 11|accessyear=2006|year=1990}}</ref> ==List of ''n''−9 fatty acids== {| class="wikitable" ! Common name ! Lipid name ! Chemical name |- ! [[oleic acid]] | 18:1 (''n''−9) | 9-octadecenoic acid |- ! [[eicosenoic acid]] | 20:1 (''n''−9) | 11-eicosenoic acid |- ! [[mead acid]] | 20:3 (''n''−9) | 5,8,11-eicosatrienoic acid |- ! [[erucic acid]] | 22:1 (''n''−9) | 13-docosenoic acid |- ! [[nervonic acid]] | 24:1 (''n''−9) | 15-tetracosenoic acid |} ==See also== * [[Polyunsaturated fatty acid]], lists of fatty acids including ''n''−3, ''n''−6, and ''n''−9 fatty acids * [[Omega-3 fatty acid|''n''−3 fatty acid]] * [[Omega-6 fatty acid|''n''−6 fatty acid]] ==References== {{reflist}} ===Additional references=== {{refbegin}} * {{cite web|author=Cyberlipid Center| title= Polyenoic fatty acids| url= http://www.cyberlipid.org/fa/acid0003.htm | accessdate=February 11| accessyear=2006}} {{refend}} {{Lipids}} [[Category:Fatty acids|ω]] [[de:Omega-9-Fettsäure]] [[es:Ácidos grasos omega 9]] [[fr:Oméga-9]] [[pt:Ômega 9]]