1.0 2011-09-21 00:32:22 UTC 2020-09-17 15:33:14 UTC FDB023609 9E,11E-Octadecadienoic acid 9E,11E-Octadecadienoic acid, also known as (e,e)-isolinoleic acid or (9E,11E)-9,11-octadecadienoate, 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. Conjugated linoleic acid (CLA) is an integral term for the mixture of positional and geometrical isomers of the octadecadienoic acids, whose two double-bonds are separated with one single-bond. The most common isomers are cis-9, trans-11, and trans-10, cis-12. 9E,11E-Octadecadienoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 9E,11E-Octadecadienoic acid has been detected in milk and dairy products (from cow) and red meat. This could make 9E,11E-octadecadienoic acid a potential biomarker for the consumption of these foods. Much attention has focused on the therapeutic potential of conjugated linoleic acid. Initial animal studies associated conjugated linoleic acid with beneficial health properties, such as reducing the risk of cancer, diabetes, atherosclerosis, inflammation, and obesity. More recent human CLA-supplementation studies have often shown conflicting and less convincing health benefits. The marked variation between studies may reflect the isomer-specific effect of the individual conjugated linoleic acid isomers, which can often have opposing effects. Detrimental effects have been observed in some studies, after supplementation with the trans-10, cis-12 conjugated linoleic acid isomer. Diet composition may modulate CLA effects on body fat accumulation. Contemporary dietary recommendations tend to limit red meat and dairy products and the possible CLA deficiencies must be compensated with dietary supplements. However, with human studies, a specific dietary pattern that controls and includes CLA has not been established. As a result, differences among studies and among subjects in the same study are likely. In rodents, the effects of CLA vary with genotype, suggesting that genetic predisposition to fat accumulation can play an important role in the effectiveness of CLA. Human volunteers with different body mass index have participated in the published studies and even in the same experiment. So, differences in lipid metabolism among subjects could help to explain the discrepancies observed in the literature. Age and maturity of the participants may also impact these studies (PMID: 17053429, 17217167, 17554969, 16477173). 9,11-Linoleic acid CLA 80 Conjugated linoleic acid Delta9,11-Octadecadienoate Delta9,11-Octadecadienoic acid Nouracid DE 554 Ricineic acid Ricinenic acid Selin CLA C18H32O2 280.4455 280.240230268 (9E,11E)-octadeca-9,11-dienoic acid 9E,11E-octadecadienoic acid 1839-11-8 CCCCCC\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/h7-10H,2-6,11-17H2,1H3,(H,19,20)/b8-7+,10-9+ JBYXPOFIGCOSSB-XBLVEGMJSA-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. Lineolic acids and derivatives Organic compounds Lipids and lipid-like molecules Fatty Acyls Lineolic acids and derivatives Aliphatic acyclic compounds 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 Unsaturated fatty acids Liquid logp 7.11 ALOGPS logs -6.28 ALOGPS solubility 1.48e-04 g/l ALOGPS logp 6.42 ChemAxon pka_strongest_acidic 4.99 ChemAxon iupac (9E,11E)-octadeca-9,11-dienoic acid ChemAxon average_mass 280.4455 ChemAxon mono_mass 280.240230268 ChemAxon smiles CCCCCC\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/h7-10H,2-6,11-17H2,1H3,(H,19,20)/b8-7+,10-9+ ChemAxon inchikey JBYXPOFIGCOSSB-XBLVEGMJSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 88.52 ChemAxon polarizability 37.12 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 16601 Specdb::CMs 38843 Specdb::CMs 174910 Specdb::MsMs 302671 Specdb::MsMs 302672 Specdb::MsMs 302673 Specdb::MsMs 345451 Specdb::MsMs 345452 Specdb::MsMs 345453 Specdb::MsMs 374009 Specdb::MsMs 374010 Specdb::MsMs 374011 Specdb::MsMs 374012 Specdb::MsMs 374013 Specdb::MsMs 440477 Specdb::MsMs 440478 Specdb::MsMs 440479 Specdb::MsMs 2256472 Specdb::MsMs 2258434 Specdb::MsMs 2260131 Specdb::MsMs 2771372 Specdb::MsMs 2771373 Specdb::MsMs 2771374 Specdb::MsMs 2908080 Specdb::MsMs 2908081 Specdb::MsMs 2908082 HMDB05047 36025 #<Reference:0x000055ce31615800> #<Reference:0x000055ce316155a8> #<Reference:0x000055ce316153a0> #<Reference:0x000055ce31615170> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Milk (Cow) Type 2 specific Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823