Fatty alcohol 1741326 225164794 2008-07-12T06:19:51Z SieBot 4005189 robot Modifying: [[de:Fettalkohole]] '''Fatty alcohols''' are [[aliphatic]] [[alcohol]]s derived from natural [[fat]]s and [[oil]]s, originating in plants, but also synthesized in animals and [[algae]]. Their significance in nutrition and health has historically been overlooked, and is only now being realized, as they are closely related to [[fatty acids]], including the well-documented [[omega 3 fatty acids]]. The other counterparts are [[fatty aldehyde]]s. Fatty alcohols usually have even number of carbon atoms. Production from fatty acids yields normal-chain alcohols&mdash;the alcohol group (-OH) attaches to the terminal carbon. Other processing can yield iso-alcohols&mdash;where the alcohol attaches to a carbon in the interior of the carbon chain. ==Current and future uses== The smaller molecules are used in [[cosmetics]] and food, and as industrial [[solvent]]s. Some of the larger molecules are simply seen as [[biofuel]]s, but little research has been done until 2006 regarding many of these, and they have been shown to be have anticancer, antiviral, antifungal, anti-[[HIV]] properties, for potential use in medicine and health supplements. Due to their [[amphipathic]] nature, fatty alcohols behave as nonionic [[surfactant]]s. They find use as [[emulsifier]]s, [[emollient]]s and [[thickener]]s in [[cosmetics]] and [[food industry]]. Fatty alcohols are a common component of [[wax]]es, mostly as [[ester]]s with [[fatty acid]]s but also as alcohols themselves. ==History== Search for polyisoprenoid alcohols was initiated with the accidental discovery of [[solanesol]] in tobacco leaves (Rowland RL et al., J Am Chem Soc 1956, 78, 4680) and isolation of several polyprenols (C30-C45) in cellulose pulp extracts (Lindgren BO, Acta Chem Scan 1965, 19, 1317). Octacosanol, present in carrots and ginseng, was found to lower cholesterol levels in 1994. Following this, a major paper was released in 2006 and another in 2007 studying hundreds of previously unstudied fatty alcohols. More than 120 [[cytotoxic]] anticancer compounds have shown confirmed activity [[in vitro]] tumor cell lines [[bioassay]] and are of current interest to Natural Cancer Institute (of Poland) for further in vivo evaluation.<ref>[http://kubicov.lib.bioinfo.pl/pmid:17584156 Natural peroxy anticancer agents<!-- Bot generated title -->]</ref> ==Types== * [[Normal-chain alcohols]] ** [[Saturated alcohols]] ** [[Unsaturated alcohols]] ** [[Acetylenic alcohols]] ** [[Sulfated alcohols]] * [[Branched-chain alcohols]] ** [[Mono-methylated]] alcohols ** [[Polyisoprenoid]] alcohols *** [[Saturated polyisoprenoids]] ([[Isopranols]]) *** [[Unsaturated polyisoprenoids]] ([[prenols]] or [[polyprenols]]) incl [[turpenols]]. * [[Phenolic alcohols]] (aka phenolphthiocerol) ==Common names== Those with common names include: * [[capryl alcohol]] (1-octanol) -- 8 carbon atoms * [[2-Ethylhexanol|2-ethyl hexanol]] -- 8 carbon atoms, branched * [[pelargonic alcohol]] (1-nonanol) -- 9 carbon atoms * [[capric alcohol]] (1-decanol, decyl alcohol) -- 10 carbon atoms * [[Dodecanol|1-dodecanol]] (lauryl alcohol) -- 12 carbon atoms * [[myristyl alcohol]] (1-tetradecanol) -- 14 carbon atoms * [[cetyl alcohol]] (1-hexadecanol) -- 16 carbon atoms * [[palmitoleyl alcohol]] (cis-9-hexadecen-1-ol) -- 16 carbon atoms, unsaturated, CH<sub>3</sub>(CH<sub>2</sub>)<sub>5</sub>CH=CH(CH<sub>2</sub>)<sub>8</sub>OH * [[stearyl alcohol]] (1-octadecanol) -- 18 carbon atoms * [[isostearyl alcohol]] (16-methylheptadecan-1-ol) -- 18 carbon atoms, branched, (CH<sub>3</sub>)<sub>2</sub>CH-(CH<sub>2</sub>)<sub>15</sub>OH * [[elaidyl alcohol]] (9E-octadecen-1-ol) -- 18 carbon atoms, unsaturated, CH<sub>3</sub>(CH<sub>2</sub>)<sub>7</sub>CH=CH(CH<sub>2</sub>)<sub>8</sub>OH * [[oleyl alcohol]] (cis-9-octadecen-1-ol) -- 18 carbon atoms, unsaturated * [[linoleyl alcohol]] (9Z, 12Z-octadecadien-1-ol) -- 18 carbon atoms, polyunsaturated, a hydrolyzation of [[linolinic acid]], an [[omega 6 fatty acid]]. * [[elaidolinoleyl alcohol]] (9E, 12E-octadecadien-1-ol) -- 18 carbon atoms, polyunsaturated * [[linolenyl alcohol]] (9Z, 12Z, 15Z-octadecatrien-1-ol) -- 18 carbon atoms, polyunsaturated * [[elaidolinolenyl alcohol]] (9E, 12E, 15-E-octadecatrien-1-ol) -- 18 carbon atoms, polyunsaturated * [[ricinoleyl alcohol]] (12-hydroxy-9-octadecen-1-ol) -- 18 carbon atoms, unsaturated, diol, CH<sub>3</sub>(CH<sub>2</sub>)<sub>5</sub>CH(OH)CH<sub>2</sub>CH=CH(CH<sub>2</sub>)<sub>8</sub>OH * [[arachidyl alcohol]] (1-eicosanol) -- 20 carbon atoms * [[behenyl alcohol]] (1-docosanol) -- 22 carbon atoms * [[erucyl alcohol]] (cis-13-docosen-1-ol) -- 22 carbon atoms, unsaturated, CH<sub>3</sub>(CH<sub>2</sub>)<sub>7</sub>CH=CH(CH<sub>2</sub>)<sub>12</sub>OH * [[lignoceryl alcohol]] (1-tetracosanol) -- 24 carbon atoms * [[ceryl alcohol]] (1-hexacosanol) -- 26 carbon atoms * [[montanyl alcohol]], [[cluytyl alcohol]] (1-octacosanol) -- 28 carbon atoms * [[myricyl alcohol]], [[melissyl alcohol]] (1-triacontanol) -- 30 carbon atoms * [[geddyl alcohol]] (1-tetratriacontanol) -- 34 carbon atoms * [[Cetearyl alcohol]] [[Behenyl alcohol]], [[lignoceryl alcohol]], [[ceryl alcohol]], [[1-heptacosanol]], [[montanyl alcohol]], [[1-nonacosanol]], [[myricyl alcohol]], [[1-dotriacontanol]], and [[geddyl alcohol]] are together classified as [[policosanol]], with montanyl alcohol and myricyl alcohol being the most abundant. ==Nutrition== Very long chain fatty alcohols (VLCFA), obtained from plant waxes and [[beeswax]] have been reported to lower plasma [[cholesterol]] in humans. They can be found in unrefined cereal grains, beeswax, and many plant-derived foods. Reports suggest that 5–20 mg per day of mixed C24–C34 alcohols, including [[octacosanol]] and [[triacontanol]], lower [[low-density lipoprotein]] (LDL) cholesterol by 21%–29% and raise [[high-density lipoprotein]] cholesterol by 8%–15%. Wax esters are [[hydrolyzed]] by a [[bile]] salt–dependent [[pancreatic]] [[carboxyl esterase]], releasing long chain alcohols and fatty acids that are absorbed in the [[gastrointestinal tract]]. Studies of fatty alcohol metabolism in [[fibroblasts]] suggest that very long chain fatty alcohols, [[fatty aldehydes]], and [[fatty acids]] are reversibly inter-converted in a [[fatty alcohol cycle]]. The metabolism of these compounds is impaired in several inherited human [[peroxisomal]] disorders, including [[adrenoleukodystrophy]] and [[Sjögren-Larsson syndrome]]. <ref>[http://www.ebmonline.org/cgi/content/abstract/229/3/215 Nutritional Significance and Metabolism of Very Long Chain Fatty Alcohols and Acids from Dietary Waxes - Hargrove et al. 229 (3): 215 - Experimental Biology and Medicine<!-- Bot generated title -->]</ref> Concentrations of VLCFA in blood plasma increase during [[fasting]] and when children are placed on [[ketogenic]] diets to suppress [[seizures]]. ==Article Sources== *{{cite web| url=http://www.cyberlipid.org/simple/simp0003.htm |title=Fatty Alcohols and Aldehydes | author = Cyberlipid|accessdate=2007-02-06}} General overview of fatty alcohols, with references. *{{cite web| url= http://www.zenitech.com/documents/new%20pdfs/articles/All%20about%20fatty%20alcohols%20Condea.pdf |title= Dr. Z Presents All about fatty alcohols |author =CONDEA| accessdate=2007-02-06}} ==See also== * [[Fatty acid]]s * [[Fatty aldehyde]]s ==References== {{Reflist}} [[Category:Alcohols]] [[Category:Fatty alcohols| ]] [[Category:Lipids]] [[de:Fettalkohole]] [[fr:Alcool gras]] [[nl:Vetalcohol]] [[pt:Álcool graxo]]