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20-September-2008 09:29:06 - Linoleic acid Linoleic acid IUPAC name cis, cis-9,12-octadecadienoic acid.1 Identifiers CAS number 60-33-3 SMILES CCCCCC=CCC=CCCCCCCCC=OO Properties Molecular formula C18H32O2 Molar mass 280.445481724 g/mol Density 0.9 g/cm3 Melting point -5 °C Boiling point °C Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Linoleic acid LA is an unsaturated omega-6 fatty acid. It is a colorless liquid. In physiological literature, it is called 18:2n-6. Chemically, linoleic acid is a carboxylic acid with an 18-carbon chain and two cis double bonds; the first double bond is located at the sixth carbon from the omega end. The word linoleic comes from the Greek word linon flax. Oleic means of, relating to, or derived from oil or of or relating to oleic acid since removing the omega-6 double bond produces oleic acid. Contents 1 In Physiology 2 Industrial uses 3 Foods 4 See also 5 References In Physiology Linoleic acid is a polyunsaturated fatty acid used in the biosynthesis of prostaglandins. It is found in the lipids of cell membranes. It is abundant in many vegetable oils, especially safflower and sunflower oils. To be fully utilised by the body, LA must be converted into gamma-linolenic acid, a reaction catalysed by the enzyme delta-6-desaturase D6D. Linoleic acid is a member of the group of essential fatty acids called omega-6 fatty acids, so called because they are an essential dietary requirement for all mammals. The other group of essential fatty acids is the omega-3 fatty acids, for example Alpha-linolenic acid. Omega-6 deficiency symptoms include dry hair, hair loss,2 and poor wound healing.3 It is easy to meet the daily requirement for these fatty acids even for people consuming low fat diets and most people get plenty of omega-6 fatty acids in their diet by consuming approximately a tablespoon of polyunsaturated plant oils per day.citation needed Industrial uses Linoleic acid is used in making soaps, emulsifiers, and quick-drying oils. Reduction of linoleic acid yields linoleyl alcohol. Linoleic acid has become increasingly popular in the beauty products industry because of its beneficial properties on the skin. Research points to linoleic acid's affective properties when applied topically on the skin, ie. anti-inflammatory, acne reduction, moisture retention properties.456 Noni seed oil is abundant in linoleic acid, and a number of beauty products contain noni seed oil.citation needed Foods Oils and foods that contain linoleic acid include safflower oil 78%, poppy seed oil 70%, hemp oil 50-70%, walnut oil, grass fed cow milk, olive oil, palm oil, sunflower oil, soybean, lard, coconut oil, egg yolks 16%, spirulina, peanut oil, okra, rice bran oil, wheat germ oil, grape seed oil, macadamia oil, pistachio oil, sesame oil. See also Alpha-linolenic acid Conjugated linoleic acid Essential fatty acids Essential fatty acid interactions Eicosanoids Essential nutrients Linolein References ^ Beare-Rogers 2001. IUPAC Lexicon of Lipid Nutrition pdf. Retrieved on 2006-02-22. ^ Cunnane S, Anderson M 1997. Pure linoleate deficiency in the rat: influence on growth, accumulation of n-6 polyunsaturates, and 1-14C linoleate oxidation. J Lipid Res 38 4: 805-12. PMID 9144095. Retrieved on 2007-01-15. ^ Ruthig DJ Meckling-Gill KA. 1999. Both n-3 and n-6 fatty acids stimulate wound healing in the rat intestinal epithelial cell line, IEC-6. Journal of Nutrition 129 10: 1791-8. PMID 10498749. Retrieved on 2007-01-15. ^ Plant oils: Topical application and anti-inflammatory effects croton oil test 1993. Dermatol. Monatsschr 179: 173. ^ Letawe,; Letawe C, Boone M, Pierard GE March 1998. Digital image analysis of the effect of topically applied linoleic acid on acne microcomedones. Clinical Experimental Dermatology 23 2: 56-58. doi:10.1046/j.1365-2230.1998.00315.x. PMID : 9692305. ^ Darmstadt, G L; Darmstadt GL, Mao-Qiang M, Chi E, Saha SK, Ziboh VA, Black RE, Santosham M, Elias PM 2002. Impact of topical oils on the skin barrier: possible implications for neonatal health in developing countries. Acta Paediatrica 91 5: 546-554. doi:10.1080/080352502753711678. Retrieved on 2007-01-12. v d e Lipids: fatty acids Saturated Butyric Hexanoic Caprylic Decanoic Lauric Myristic Palmitic Stearic Arachidic Behenic Lignoceric n-3 Unsaturated α-Linolenic Stearidonic Eicosapentaenoic Docosahexaenoic n-6 Unsaturated Linoleic γ-Linolenic Dihomo-γ-linolenic Arachidonic n-9 Unsaturated Oleic Erucic Nervonic Retrieved from http://en..org/wiki/Linoleic_acid Categories: Carboxylic acids | Essential fatty acids | Essential nutrients | Fatty acidsHidden categories: All articles with statements | Articles with statements since February 2007 | Articles with statements since December 2007 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages العربية ÄŒesky Deutsch Español Français LatvieÅ¡u Nederlands 日本語 Polski Português РуÑ?Ñ?кий Suomi Svenska This page was last modified on 5 July 2008, at 00:33
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