1.0 2011-09-21 01:51:28 UTC 2015-07-21 06:59:39 UTC FDB029190 9'-Carboxy-alpha-chromanol 9'-carboxy-alpha-tocopherol is a dehydrogenation carboxylate product of 9'-hydroxy-a-tocopherol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate The tocopherols ( a-tocopherol , b-tocopherol ,r-tocopherol and d-tocopherol ) and their corresponding tocotrienols are synthesized by plants and have vitamin E antixoidant activity (see pathway vitamin E biosynthesis ). They differ in the number and location of methyl groups on the chromanol ring. The naturally occurring form of a-tocopherol is (2R,4'R,8'R)-a-tocopherol (synonym (R,R,R)-a-tocopherol). Synthetic a-tocopherols are a racemic mixture of eight different R and S stereoisomers. Only the 2R forms are recognized as meeting human requirements. The in vivo function of vitamin E is to scavenge peroxyl radicals via its phenolic (chromanol) hydroxyl group, thus protecting lipids against free radical-catalyzed peroxidation. The tocopheryl radical formed can then be reduced by reductants such as L-ascorbate. Other major products of a-tocopherol oxidation include α-tocopherylquinone and epoxy-a-tocopherols. The metabolites a-tocopheronic acid and its lactone, known as the Simon metabolites, are generally believed to be artefacts. In addition to these oxidation products, the other major class of tocopherol metabolites is the carboxyethyl-hydroxychromans.These metabolites are produced in significant amounts in response to excess vitamin E ingestion. Vitamin E is fat-soluble and its utilization requires intestinal fat absorption mechanisms. It is secreted from the intestine into the lymphatic system in chylomicrons which subsequently enter the plasma. Lipolysis of these chylomicrons can result in delivery of vitamin E to tissues, transfer to high-density lipoproteins (and subsequently to other lipoproteins via the phospholipid exchange protein), or retention in chylomicron remnants. These remnants are taken up by the liver. Natural (R,R,R)-α-tocopherol and synthetic 2R-α-tocopherols are then preferentially secreted from the liver into plasma as a result of the specificity of the α-tocopherol transfer protein. This protein, along with the metabolism of excess vitamin E in the liver and excretion into urine and bile, mediate the supply of a-tocopherol in plasma and tissues [HMDB] 2-(9-carboxy-4,8-dimethylnonyl)-6-hydroxy-2,5,7,8-tetramethylchroman 2,5,7,8-Tetramethyl-2-(4',8'-dimethyl-9'-carboxy-nonyl)-6-chromanol 9'-carboxy-alpha-tocopherol C24H38O4 390.5561 390.277009704 (6S)-9-[(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnonanoic acid (6S)-9-[(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6-dimethylnonanoic acid C[C@@H](CCCC(C)C(O)=O)CCC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C InChI=1S/C24H38O4/c1-15(9-7-11-16(2)23(26)27)10-8-13-24(6)14-12-20-19(5)21(25)17(3)18(4)22(20)28-24/h15-16,25H,7-14H2,1-6H3,(H,26,27)/t15-,16?,24-/m0/s1 CUGVBZDXUTZXJO-GCIQOJCMSA-N belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. 1-benzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds Alkyl aryl ethers Benzenoids Carbonyl compounds Carboxylic acids Heterocyclic fatty acids Hydrocarbon derivatives Hydroxy fatty acids Medium-chain fatty acids Methyl-branched fatty acids Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds 1-benzopyran Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Branched fatty acid Carbonyl group Carboxylic acid Carboxylic acid derivative Ether Fatty acid Fatty acyl Heterocyclic fatty acid Hydrocarbon derivative Hydroxy fatty acid Medium-chain fatty acid Methyl-branched fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Oxacycle Solid logp 5.67 ALOGPS logs -5.83 ALOGPS solubility 5.78e-04 g/l ALOGPS logp 7.38 ChemAxon pka_strongest_acidic 5 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (6S)-9-[(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnonanoic acid ChemAxon average_mass 390.5561 ChemAxon mono_mass 390.277009704 ChemAxon smiles C[C@@H](CCCC(C)C(O)=O)CCC[C@@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C ChemAxon formula C24H38O4 ChemAxon inchi InChI=1S/C24H38O4/c1-15(9-7-11-16(2)23(26)27)10-8-13-24(6)14-12-20-19(5)21(25)17(3)18(4)22(20)28-24/h15-16,25H,7-14H2,1-6H3,(H,26,27)/t15-,16?,24-/m0/s1 ChemAxon inchikey CUGVBZDXUTZXJO-GCIQOJCMSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 114.11 ChemAxon polarizability 47.16 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 322009 Specdb::MsMs 322010 Specdb::MsMs 322011 Specdb::MsMs 369790 Specdb::MsMs 369791 Specdb::MsMs 369792 Specdb::MsMs 2419797 Specdb::MsMs 2419798 Specdb::MsMs 2419799 Specdb::MsMs 2543249 Specdb::MsMs 2543250 Specdb::MsMs 2543251 Specdb::CMs 25300 Specdb::CMs 40007 Specdb::CMs 130354 Specdb::CMs 138088 HMDB12866