1.0 2016-09-30 23:21:03 UTC 2020-06-04 22:43:33 UTC BMDB0006270 BMDB06270 Linoelaidic acid Linoleic acid, also known as linoleate, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Linoleic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Linoleic acid exists in all eukaryotes, ranging from yeast to humans. 18:2, N-6,9 all-trans 9E,12E-Octadecadienoic acid C18:2, N-6,9 all-trans trans-9,trans-12-Linoleic acid 9E,12E-Octadecadienoate trans-9,trans-12-Linoleate Linoelaidate (9E,12E)-9,12-Octadecadienoate (9E,12E)-9,12-Octadecadienoic acid 9,12-Octadecadienoic acid Linoleic acid Linoleic acid, (Z,Z)-isomer, 14C-labeled Linolelaidic acid cis,cis-9,12-Octadecadienoic acid Linoleic acid, (e,e)-isomer Linoleic acid, (Z,Z)-isomer Linoleic acid, ammonium salt, (Z,Z)-isomer Linoleic acid, potassium salt, (Z,Z)-isomer Linoelaidic acid, (e,Z)-isomer 9 trans,12 trans Octadecadienoic acid Linoleic acid, sodium salt, (e,e)-isomer Linoleic acid, sodium salt, (Z,Z)-isomer Acid, 9,12-octadecadienoic trans,trans-9,12-Octadecadienoic acid Linoleic acid, (Z,e)-isomer 9,12 Octadecadienoic acid Linoleic acid, calcium salt, (Z,Z)-isomer 9-trans,12-trans-Octadecadienoic acid Linoleate C18H32O2 280.4455 280.240230268 (9E,12E)-octadeca-9,12-dienoic acid linoelaidic acid 506-21-8 CCCCC\C=C\C\C=C\CCCCCCCC(O)=O InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6+,10-9+ OYHQOLUKZRVURQ-AVQMFFATSA-N belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Organic compounds Lipids and lipid-like molecules Fatty Acyls Lineolic acids and derivatives Lineolic acids and derivatives Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Unsaturated fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Long-chain fatty acid Monocarboxylic acid or derivatives Octadecanoid Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Unsaturated fatty acid Aliphatic acyclic compounds Unsaturated fatty acids octadecadienoic acid omega-6 fatty acid Solid melting_point 28 - 29 °C logp 7.06 ALOGPS logs -6.26 ALOGPS logp 6.42 ChemAxon pka_strongest_acidic 4.99 ChemAxon iupac (9E,12E)-octadeca-9,12-dienoic acid ChemAxon average_mass 280.4455 ChemAxon mono_mass 280.240230268 ChemAxon smiles CCCCC\C=C\C\C=C\CCCCCCCC(O)=O ChemAxon formula C18H32O2 ChemAxon inchi InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6+,10-9+ ChemAxon inchikey OYHQOLUKZRVURQ-AVQMFFATSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 88.52 ChemAxon polarizability 35.45 ChemAxon rotatable_bond_count 14 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::CMs 3099 Specdb::CMs 38985 Specdb::CMs 152501 Specdb::MsMs 106785 Specdb::MsMs 106786 Specdb::MsMs 106787 Specdb::MsMs 173616 Specdb::MsMs 173617 Specdb::MsMs 173618 Specdb::MsMs 285950 Specdb::MsMs 285951 Specdb::MsMs 285952 Specdb::MsMs 285953 Specdb::MsMs 285954 Specdb::MsMs 373990 Specdb::MsMs 373991 Specdb::MsMs 373992 Specdb::MsMs 373993 Specdb::MsMs 373994 Specdb::MsMs 440466 Specdb::MsMs 440467 Specdb::MsMs 440468 Specdb::MsMs 2257394 Specdb::MsMs 2259214 Specdb::MsMs 2259339 Specdb::MsMs 2281399 Specdb::MsMs 2281400 Specdb::MsMs 2281401 Adipose Tissue Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with flaxseed for 205 days. Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014. 25093808 Adipose Tissue 5522.11 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 5275.89 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 38145.42 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 47861.6 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 37266.63 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 44394.79 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 Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with sunflower seed for 205 days. Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014. 25093808 Adipose Tissue Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with flaxseed for 205 days. Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014. 25093808 Adipose Tissue 42361.17 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 46533.11 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 40678.14 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 45099.67 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 Adipose Tissue Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with sunflower seed for 205 days. Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014. 25093808 Milk Pasteurized milk with 3.9% fat, organic, by GC-FID 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 FDB023868 4445609 5282457 75108 C00036669 2217974 Linoelaidic_acid Gunstone, Frank D.; Lie Ken Jie, M. Fatty acids. 24. Synthesis of ten octadecadiynoic acids and of the related cis,cis- and trans,trans-octadecadienoic acids. Chemistry and Physics of Lipids (1970), 4(1), 1-14. 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