2.02012-08-09 09:16:12 -06002015-09-13 15:15:33 -0600ECMDB21423M2MDB001818Elaidic acidElaidic acid is an unsaturated trans fatty acid that is similar to the cis-fatty acid known as oleic acid. Trans fatty acids can be found in nature (especially in dairy products) but the majority of trans fatty acids produced today are from food processing techniques.Elaidatetrans-9-OctadecenoateTrans-9-Octadecenoic acidtrans-OleateTrans-Oleic acidC18H34O2282.4614282.255880332(9Z)-octadec-9-enoic acidoleic acid112-79-8CCCCCCCC\C=C/CCCCCCCC(O)=OInChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-ZQPPMHVWECSIRJ-KTKRTIGZSA-NSolidMembranelogp7.68logs-6.37solubility1.21e-04 g/lmelting_point42-44 oClogp6.78pka_strongest_acidic4.99iupac(9Z)-octadec-9-enoic acidaverage_mass282.4614mono_mass282.255880332smilesCCCCCCCC\C=C/CCCCCCCC(O)=OformulaC18H34O2inchiInChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-inchikeyZQPPMHVWECSIRJ-KTKRTIGZSA-Npolar_surface_area37.3refractivity87.4polarizability37.09rotatable_bond_count15acceptor_count2donor_count1physiological_charge-1formal_charge0Specdb::CMs463Specdb::CMs1874Specdb::CMs2563Specdb::CMs27397Specdb::CMs30911Specdb::CMs31072Specdb::CMs37356Specdb::CMs153882Specdb::CMs1054040Specdb::EiMs1978Specdb::NmrOneD1190Specdb::MsMs334Specdb::MsMs335Specdb::MsMs336Specdb::MsMs797Specdb::MsMs798Specdb::MsMs799Specdb::MsMs3612Specdb::MsMs3613Specdb::MsMs178443Specdb::MsMs178444Specdb::MsMs178445Specdb::MsMs180762Specdb::MsMs180763Specdb::MsMs180764Specdb::MsMs285572Specdb::MsMs285573Specdb::MsMs285574Specdb::MsMs285575Specdb::MsMs373995Specdb::MsMs373996Specdb::MsMs373997Specdb::MsMs373998Specdb::MsMs373999Specdb::MsMs438646Specdb::MsMs440469Specdb::NmrTwoD1206HMDB00573965393217C0071227997OLIElaidic acidvan der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.17765195Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.ASreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4.19212411Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69.8412012Cater NB, Denke MA: Behenic acid is a cholesterol-raising saturated fatty acid in humans. Am J Clin Nutr. 2001 Jan;73(1):41-4.11124748Ayala-Bravo HA, Quintanar-Guerrero D, Naik A, Kalia YN, Cornejo-Bravo JM, Ganem-Quintanar A: Effects of sucrose oleate and sucrose laureate on in vivo human stratum corneum permeability. Pharm Res. 2003 Aug;20(8):1267-73.12948025Bajaj M, Suraamornkul S, Romanelli A, Cline GW, Mandarino LJ, Shulman GI, DeFronzo RA: Effect of a sustained reduction in plasma free fatty acid concentration on intramuscular long-chain fatty Acyl-CoAs and insulin action in type 2 diabetic patients. Diabetes. 2005 Nov;54(11):3148-53.16249438Takahashi K, Rytting JH: Novel approach to improve permeation of ondansetron across shed snake skin as a model membrane. J Pharm Pharmacol. 2001 Jun;53(6):789-94.11428654Jensen MD: Gender differences in regional fatty acid metabolism before and after meal ingestion. J Clin Invest. 1995 Nov;96(5):2297-303.7593616Russell AP, Somm E, Debigare R, Hartley O, Richard D, Gastaldi G, Melotti A, Michaud A, Giacobino JP, Muzzin P, LeBlanc P, Maltais F: COPD results in a reduction in UCP3 long mRNA and UCP3 protein content in types I and IIa skeletal muscle fibers. J Cardiopulm Rehabil. 2004 Sep-Oct;24(5):332-9.15602154Crocker I, Lawson N, Daniels I, Baker P, Fletcher J: Significance of fatty acids in pregnancy-induced immunosuppression. Clin Diagn Lab Immunol. 1999 Jul;6(4):587-93.10391868Colette C, Percheron C, Pares-Herbute N, Michel F, Pham TC, Brillant L, Descomps B, Monnier L: Exchanging carbohydrates for monounsaturated fats in energy-restricted diets: effects on metabolic profile and other cardiovascular risk factors. Int J Obes Relat Metab Disord. 2003 Jun;27(6):648-56.12833107Christophe AB, De Greyt WF, Delanghe JR, Huyghebaert AD: Substituting enzymatically interesterified butter for native butter has no effect on lipemia or lipoproteinemia in Man. Ann Nutr Metab. 2000;44(2):61-7.10970994de la Maza MP, Hirsch S, Nieto S, Petermann M, Bunout D: Fatty acid composition of liver total lipids in alcoholic patients with and without liver damage. Alcohol Clin Exp Res. 1996 Nov;20(8):1418-22.8947319Droke EA, Briske-Anderson M, Lukaski HC: Fatty acids alter monolayer integrity, paracellular transport, and iron uptake and transport in Caco-2 cells. Biol Trace Elem Res. 2003 Dec;95(3):219-32.14665727Valjakka-Koskela R, Hirvonen J, Monkkonen J, Kiesvaara J, Antila S, Lehtonen L, Urtti A: Transdermal delivery of levosimendan. Eur J Pharm Sci. 2000 Oct;11(4):343-50.11033078Jones AE, Stolinski M, Smith RD, Murphy JL, Wootton SA: Effect of fatty acid chain length and saturation on the gastrointestinal handling and metabolic disposal of dietary fatty acids in women. Br J Nutr. 1999 Jan;81(1):37-43.10341674Thielitz A, Helmdach M, Ropke EM, Gollnick H: Lipid analysis of follicular casts from cyanoacrylate strips as a new method for studying therapeutic effects of antiacne agents. Br J Dermatol. 2001 Jul;145(1):19-27.11453902Richieri GV, Ogata RT, Kleinfeld AM: Equilibrium constants for the binding of fatty acids with fatty acid-binding proteins from adipocyte, intestine, heart, and liver measured with the fluorescent probe ADIFAB. J Biol Chem. 1994 Sep 30;269(39):23918-30.7929039Lima WP, Carnevali LC Jr, Eder R, Costa Rosa LF, Bacchi EM, Seelaender MC: Lipid metabolism in trained rats: effect of guarana (Paullinia cupana Mart.) supplementation. Clin Nutr. 2005 Dec;24(6):1019-28. Epub 2005 Sep 22.16182414Vinggaard AM, Provost JJ, Exton JH, Hansen HS: Arf and RhoA regulate both the cytosolic and the membrane-bound phospholipase D from human placenta. Cell Signal. 1997 Feb;9(2):189-96.9113419Mittendorfer B, Liem O, Patterson BW, Miles JM, Klein S: What does the measurement of whole-body fatty acid rate of appearance in plasma by using a fatty acid tracer really mean? Diabetes. 2003 Jul;52(7):1641-8.12829627Andersen TC, Pedersen JF, Nordentoft T, Olsen O: Fat and mesenteric blood flow. Scand J Gastroenterol. 1999 Sep;34(9):894-7.10522608Hu, Sheng; Yuan, Ji-rong; Zhu, Jin; Yin, Ying-sui. Preparation of high-purity oleic acid by selective reaction. Yingyong Huagong (2005), 34(12), 748-750, 753.http://hmdb.ca/system/metabolites/msds/000/000/492/original/HMDB00573.pdf?1358461685