[{"@context":"http:\/\/schema.org\/","@type":"BlogPosting","@id":"https:\/\/wiki.edu.vn\/en\/wiki8\/omega-hydroxy-acid-wikipedia\/#BlogPosting","mainEntityOfPage":"https:\/\/wiki.edu.vn\/en\/wiki8\/omega-hydroxy-acid-wikipedia\/","headline":"Omega hydroxy acid – Wikipedia","name":"Omega hydroxy acid – Wikipedia","description":"From Wikipedia, the free encyclopedia Omega hydroxy acids (\u03c9-hydroxycarboxylic acids) are a class of naturally occurring straight-chain aliphatic organic acids","datePublished":"2014-04-28","dateModified":"2014-04-28","author":{"@type":"Person","@id":"https:\/\/wiki.edu.vn\/en\/wiki8\/author\/lordneo\/#Person","name":"lordneo","url":"https:\/\/wiki.edu.vn\/en\/wiki8\/author\/lordneo\/","image":{"@type":"ImageObject","@id":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","url":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","height":96,"width":96}},"publisher":{"@type":"Organization","name":"Enzyklop\u00e4die","logo":{"@type":"ImageObject","@id":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","url":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","width":600,"height":60}},"image":{"@type":"ImageObject","@id":"https:\/\/en.wikipedia.org\/wiki\/Special:CentralAutoLogin\/start?type=1x1","url":"https:\/\/en.wikipedia.org\/wiki\/Special:CentralAutoLogin\/start?type=1x1","height":"1","width":"1"},"url":"https:\/\/wiki.edu.vn\/en\/wiki8\/omega-hydroxy-acid-wikipedia\/","wordCount":3856,"articleBody":"From Wikipedia, the free encyclopediaOmega hydroxy acids (\u03c9-hydroxycarboxylic acids) are a class of naturally occurring straight-chain aliphatic organic acids n carbon atoms long with a carboxyl group at position 1 (the starting point for the family of carboxylic acids), and a hydroxyl at terminal position n where n > 3. The C16 and C18 omega hydroxy acids 16-hydroxy palmitic acid and 18-hydroxy stearic acid are key monomers of cutin in the plant cuticle.[1][2] The polymer cutin is formed by interesterification of omega hydroxy acids and derivatives of them that are substituted in mid-chain, such as 10,16-dihydroxy palmitic acid.[3][4] Only the epidermal cells of plants synthesize cutin.[5]Omega hydroxy fatty acids also occur in animals. Cytochrome P450 (CYP450) microsome \u03c9-hydroxylases such as CYP4A11, CYP4A22, CYP4F2, and CYP4F3 in humans, Cyp4a10 and Cyp4a12 in mice, and Cyp4a1, Cyp4a2, Cyp4a3, and Cyp4a8 in rats metabolize arachidonic acid and many arachidonic acid metabolites to their corresponding omega hydroxyl products.[6] This metabolism of arachidonic acid produces 20-hydroxyarachidonic acid (i.e. 20-hydroxyeicosatetraeonic acid or 20-HETE), a bioactive product involved in various physiological and pathological processes;[7] and this metabolism of certain bioactive arachidonic acid metabolites such as leukotriene B4 and 5-hydroxyicosatetraenoic acid produces 20-hydroxylated products which are 100- to 1,000-fold weaker than, and therefore represents the inactivation of, their respective precursors.[8][9][10]The definition for “omega” includes number of carbons (C#) greater or equal to three. Lower numbers are included here to match the formula pattern CnH2nO3.C#systematic nametrivial namemelting point\u00b0CformulaSMILESCASNoPubChem CIDChemSpiderIDUNIIChEBIoccurrencereference1Carbonic acidCH2O3OC(=O)O463-79-6767747142M471B3J2897622-Hydroxyethanoic acidGlycolic acid75C2H4O3OCC(=O)O79-14-17577370WT12SX38S17497plants33-Hydroxypropionic acid\u03b2-Lactic acid139-140C3H6O3OCCC(=O)O503-66-26815261460most living organisms44-Hydroxybutanoic acidgamma-Hydroxybutyric acid?C4H8O3OCCCC(=O)O591-81-110413998430IW36W5B230830human neurotransmitter55-Hydroxypentanoic acid5-hydroxyvaleric acidC5H10O3OCCCCC(=O)O13392-69-32594524171H5EVV4LP594556466-Hydroxyhexanoic acid6-Hydroxycaproic acidC6H12O3OCCCCCC(=O)O1191-25-914490138353Y3OX37NM81786977-Hydroxyheptanoic acidC7H14O3OCCCCCCC(=O)O3710-42-71380161216607911288-Hydroxyoctanoic acidomega-hydroxycaprylic acidC8H16O3OCCCCCCCC(=O)O764-89-669820630187916299-Hydroxynonanoic acid9-hydroxypelargonic acidC9H18O3OCCCCCCCCC(=O)O3788-56-5138052121694HV672SU12G791211010-Hydroxydecanoic acid10-hydroxy capric acidC10H20O3OCCCCCCCCCC(=O)O1679-53-47430066903NP03XO416B174091111-Hydroxyundecanoic acid11-HUDAC11H22O3OCCCCCCCCCCC(=O)O3669-80-57723769664SD6J9LX2XK791261212-Hydroxydodecanoic acidSabinic acidC12H24O3OCCCCCCCCCCCC(=O)O505-95-37903471366SUH3LR2K9D39567[11]1313-Hydroxytridecanoic acidC13H26O3OCCCCCCCCCCCCC(=O)O7735-38-8139065122656791661414-Hydroxytetradecanoic acid\u03c9-hydroxy myristic acidC14H28O3OCCCCCCCCCCCCCC(=O)O17278-74-90842762341369771681515-Hydroxypentadecanoic acidC15H30O3OCCCCCCCCCCCCCCC(=O)O4617-33-87836070730FU65P3692T79169Angelica archangelica1616-hydroxyhexadecanoic acidJuniperic acidC16H32O3OCCCCCCCCCCCCCCCC(=O)O506-13-8104661003455328plant cuticle[12]1717-Hydroxyheptadecanoic acidC17H34O3OCCCCCCCCCCCCCCCCC(=O)O13099-34-84308451351397779177Pinus radiata1818-Hydroxyoctadecanoic acid\u03c9-hydroxystearic acidC18H36O3OCCCCCCCCCCCCCCCCCC(=O)O3155-42-852829154446042CCR5P6ICT279182plant cutin1919-Hydroxynonadecanoic acidC19H38O3OCCCCCCCCCCCCCCCCCCC(=O)O52829174446044791792020-Hydroxyicosanoic acid\u03c9-hydroxyarachidic acidC20H40O3OCCCCCCCCCCCCCCCCCCCC(=O)O62643-46-35282919444604679190stem and seed cutin2121-Hydroxyhenicosanoic acidC21H42O3OCCCCCCCCCCCCCCCCCCCCC(=O)O52829204446047791952222-Hydroxydocosanoic acid22-hydroxybehenic acidC22H44O3OCCCCCCCCCCCCCCCCCCCCCC(=O)O506-45-652829224446049763222323-Hydroxytricosanoic acidC23H46O3OCCCCCCCCCCCCCCCCCCCCCCC(=O)O61658-18-2117604429935141cutin2424-Hydroxytetracosanoic acidC24H48O3OCCCCCCCCCCCCCCCCCCCCCCCC(=O)O75912-18-4531278044722052525-Hydroxypentacosanoic acidC25H50O3OCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O82612-07-514325176575075832626-Hydroxyhexacosanoic acid\u03c9-hydroxycerotic acidC26H52O3OCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O506-47-853127854472210763252727-Hydroxyheptacosanoic acidC27H54O3OCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O1432517713739624848612828-Hydroxyoctacosanoic acidC28H56O3OCCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O52900-17-153127864472211848632929-hydroxynonacosanoic acidomega-Hydroxynonacosanoic acidC29H58O3OCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O1432517834449103848653030-Hydroxytriacontanoic acidC30H60O3OCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O52900-18-25312787447221276220See also[edit]References[edit]^ Kolattukudy, P. E.; Walton, T. J. (1972). “Structure and biosynthesis of the hydroxy fatty acids of cutin in Vicia faba leaves”. Biochemistry. 11 (10): 1897\u20131907. doi:10.1021\/bi00760a026. PMID\u00a05025632.^ Soliday, C. L.; Kolattukudy, P. E. (1977). “Biosynthesis of Cutin \u03c9-hydroxylation of fatty acids by a microsomal preparation from germinating Vicia faba“. Plant Physiology. 59 (6): 1116\u20131121. doi:10.1104\/pp.59.6.1116. PMC\u00a0542517. PMID\u00a016660004.^ T.J. Walton TJ and P.E. Kolattukudy (1972) Enzymatic conversion of 16-hydroxypalmitic acid into 10,16-dihydroxypalmitic acid in Vicia faba epidermal extracts. Biochem Biophys Res Communications 46, (1), 16\u201321^ P. J. Holloway (1982) The chemical constitution of plant cutins. p45-85 in In “The Plant Cuticle”. ed. by DF Cutler, KL Alvin and CE Price. Academic Press, London. ISBN\u00a00-12-199920-3^ Kolattukudy, PE (1996) Biosynthetic pathways of cutin and waxes, and their sensitivity to environmental stresses. In: Plant Cuticles. Ed. by G. Kerstiens, BIOS Scientific publishers, Oxford, pp 83-108^ Hoopes SL, Garcia V, Edin ML, Schwartzman ML, Zeldin DC (Jul 2015). “Vascular actions of 20-HETE”. Prostaglandins & Other Lipid Mediators. 120: 9\u201316. doi:10.1016\/j.prostaglandins.2015.03.002. PMC\u00a04575602. PMID\u00a025813407.^ Annu Rev Pharmacol Toxicol. 2005;45:413-38^ Du, L; Yin, H; Morrow, JD; Strobel, HW; Keeney, DS (2009). “20-Hydroxylation is the CYP-dependent and retinoid-inducible leukotriene B4 inactivation pathway in human and mouse skin cells”. Archives of Biochemistry and Biophysics. 484 (1): 80\u201386. doi:10.1016\/j.abb.2009.01.012. PMC\u00a02687325. PMID\u00a019467632.^ J Immunol. 1986 Nov 15;137(10):3277-83^ Powell, WS; Rokach, J (Apr 2015). “Biosynthesis, biological effects, and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid”. Biochim Biophys Acta. 1851 (4): 340\u2013355. doi:10.1016\/j.bbalip.2014.10.008. PMC\u00a05710736. PMID\u00a025449650.^ Lycan, W. H.; Adams, Roger (February 1929). “Omega-Hydroxy Aliphatic Acids. Synthesis of Sabinic Acid”. Journal of the American Chemical Society. 51 (2): 625\u2013629. doi:10.1021\/ja01377a042. ISSN\u00a00002-7863.^ Spring, F. S. (March 1945). “Naturally Occurring Polyesters”. Nature. 155 (3931): 272. Bibcode:1945Natur.155..272S. doi:10.1038\/155272b0. ISSN\u00a00028-0836. S2CID\u00a04108900."},{"@context":"http:\/\/schema.org\/","@type":"BreadcrumbList","itemListElement":[{"@type":"ListItem","position":1,"item":{"@id":"https:\/\/wiki.edu.vn\/en\/wiki8\/#breadcrumbitem","name":"Enzyklop\u00e4die"}},{"@type":"ListItem","position":2,"item":{"@id":"https:\/\/wiki.edu.vn\/en\/wiki8\/omega-hydroxy-acid-wikipedia\/#breadcrumbitem","name":"Omega hydroxy acid – Wikipedia"}}]}]