1.0 2016-09-30 22:33:00 UTC 2020-06-04 22:28:40 UTC BMDB0000573 BMDB00573 BMDB0063575 BMDB63575 Elaidic acid Elaidic acid, also known as (9E)-octadecenoic acid, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Elaidic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Elaidic acid is the major trans fat found in hydrogenated vegetable oils and occurs in small amounts in caprine and bovine milk (very roughly 0.1 % of the fatty acids) and some meats. It is the trans isomer of oleic acid. The name of the elaidinization reaction comes from elaidic acid. Elaidic acid increases CETP activity, which in turn raises VLDL and lowers HDL cholesterol (Wikipedia). (9E)-Octadecenoic acid (e)-Oleic acid 9-OCTADECENOIC ACID 9-trans-Octadecenoic acid Acide elaidique D9-trans-Octadecenoic acid Elaidinsaure Elaidinsaeure trans-9-Octadecenoic acid trans-D9-Octadecenoic acid trans-Delta(9)-Octadecenoic acid trans-Elaidic acid trans-Oleic acid (9E)-Octadecenoate (e)-Oleate 9-OCTADECENOate 9-trans-Octadecenoate D9-trans-Octadecenoate trans-9-Octadecenoate trans-D9-Octadecenoate trans-delta(9)-Octadecenoate trans-Δ(9)-octadecenoate trans-Δ(9)-octadecenoic acid trans-Elaidate trans-Oleate Elaidate FA(18:1(9E)) 9-Elaidate 18:1 N-9 C18:1 N-9 Octadec-9-enoic acid Octadec-9-enoate 9,10-Octadecenoate 9,10-Octadecenoic acid Acid, 9-octadecenoic 9 Octadecenoic acid (9E)-9-Octadecenoic acid (e)-9-Octadecenoic acid 9-trans-Oleic acid Elaidinic acid delta9-trans-Octadecenoic acid trans-delta9-Octadecenoic acid trans-Δ9-octadecenoic acid Δ9-trans-octadecenoic acid Elaidic acid C18H34O2 282.4614 282.255880332 (9E)-octadec-9-enoic acid elaidic acid 112-79-8 [H]\C(CCCCCCCC)=C(\[H])CCCCCCCC(O)=O InChI=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-MDZDMXLPSA-N belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Long-chain fatty acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Unsaturated fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Unsaturated fatty acid Aliphatic acyclic compounds Monounsaturated fatty acids Unsaturated fatty acids Unsaturated fatty acids octadec-9-enoic acid Liquid melting_point 42 - 44 °C logp 6.78 Extrapolated logp 7.68 ALOGPS logs -6.37 ALOGPS logp 6.78 ChemAxon pka_strongest_acidic 4.99 ChemAxon iupac (9E)-octadec-9-enoic acid ChemAxon average_mass 282.4614 ChemAxon mono_mass 282.255880332 ChemAxon smiles [H]\C(CCCCCCCC)=C(\[H])CCCCCCCC(O)=O ChemAxon formula C18H34O2 ChemAxon inchi InChI=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+ ChemAxon inchikey ZQPPMHVWECSIRJ-MDZDMXLPSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 87.4 ChemAxon polarizability 37.64 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::EiMs 809 Specdb::CMs 1881 Specdb::CMs 23176 Specdb::CMs 31169 Specdb::CMs 32369 Specdb::CMs 37631 Specdb::CMs 151247 Specdb::CMs 1066884 Specdb::NmrTwoD 1370 Specdb::NmrOneD 1425 Specdb::NmrOneD 2163 Specdb::NmrOneD 2851 Specdb::MsMs 84009 Specdb::MsMs 84010 Specdb::MsMs 84011 Specdb::MsMs 145758 Specdb::MsMs 145759 Specdb::MsMs 145760 Specdb::MsMs 2235923 Specdb::MsMs 2237470 Specdb::MsMs 2239502 Specdb::MsMs 2469820 Specdb::MsMs 2469821 Specdb::MsMs 2469822 Specdb::MsMs 2492333 Specdb::MsMs 2492334 Specdb::MsMs 2492335 Adipose Tissue 933.22 nmol/g of tissue Intramuscular (IMF) fat of beef steers fed red clover silage with flaxseed. C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20. Adipose Tissue 368.62 nmol/g of tissue Intramuscular (IMF) fat of beef steers fed red clover silage without flaxseed. C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20. Adipose Tissue 17763.52 nmol/g of tissue Perirenal (PF) fat of beef steers fed red clover silage with flaxseed. C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20. Adipose Tissue 6465.31 nmol/g of tissue Perirenal (PF) fat of beef steers fed red clover silage without flaxseed. C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20. Adipose Tissue 14110.42 nmol/g of tissue Subcutaneous (SF) fat of beef steers fed red clover silage with flaxseed. C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20. Adipose Tissue 5799.73 nmol/g of tissue Subcutaneous (SF) fat of beef steers fed red clover silage without flaxseed. C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20. Adipose Tissue 8602.95 nmol/g of tissue Fatty acid of subcutaneous fat. Calf-finished Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41. 24188642 Adipose Tissue 8921.57 nmol/g of tissue Fatty acid of subcutaneous fat. With growth promoting implants Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41. 24188642 Adipose Tissue 8468.41 nmol/g of tissue Fatty acid of subcutaneous fat. Without growth promoting implants Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41. 24188642 Adipose Tissue 8889.71 nmol/g of tissue Fatty acid of subcutaneous fat. Yearling-finished Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41. 24188642 Adipose Tissue Cull beef cows fed barley silage diet for 12 weeks He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281. 22274861 Adipose Tissue Cull beef cows fed barley silage diet with flaxseed for 12 weeks He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281. 22274861 Adipose Tissue Cull beef cows fed hay for 12 weeks He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281. 22274861 Adipose Tissue Cull beef cows fed hay with flaxseed for 12 weeks He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281. 22274861 Fibroblasts Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Milk Raw milk from 6 Holstein and 6 Montbeliarde cows Lopez C, Briard-Bion V, Menard O, Rousseau F, Pradel P, Besle JM: Phospholipid, sphingolipid, and fatty acid compositions of the milk fat globule membrane are modified by diet. J Agric Food Chem. 2008 Jul 9;56(13):5226-36. doi: 10.1021/jf7036104. Epub 2008 Jun 4. 18522410 Milk This is a duplicate concentration of concentration_id 4476, unpexported by An Chi on Aug 20, 2018 Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. 11913692 Milk 10691.726 uM Milk, partly skim, conventional (not organic), 1.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 10691.726 uM Milk, partly skim, organic, 1.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 2372.00552 uM Skim milk Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 3681.919 uM Milk, skim, 0.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 2372.00552 uM Milk, skim, organic Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 27224.959 uM Milk, whole, 3.5, (UHT), % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 26198.27 uM Milk, whole, conventional (not organic), 3.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 26198.27 uM Milk, whole, organic, 3.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Muscle Samples have been collected from Heifer cows. Osorio MT, Downey G, Moloney AP, Rohrle FT, Luciano G, Schmidt O, Monahan FJ: Beef authentication using dietary markers: chemometric selection and modelling of significant beef biomarkers using concatenated data from multiple analytical methods. Food Chem. 2013 Dec 1;141(3):2795-801. doi: 10.1016/j.foodchem.2013.05.118. Epub 2013 Jun 5. 23871026 FDB002951 C01712 553123 DB04224 C00052377 637517 27997 38213 Elaidic_acid 3406 Vitagliano, Michele. Formation of elaidic acid. Oli, Grassi, Derivati (1967), 111(12), 77-8. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. 11913692 Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. 20855010 Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026. 29570652 van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. 28219465 Lopez C, Briard-Bion V, Menard O, Rousseau F, Pradel P, Besle JM: Phospholipid, sphingolipid, and fatty acid compositions of the milk fat globule membrane are modified by diet. J Agric Food Chem. 2008 Jul 9;56(13):5226-36. doi: 10.1021/jf7036104. Epub 2008 Jun 4. 18522410 Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en