1.0 2016-09-30 22:46:43 UTC 2020-06-04 19:14:00 UTC BMDB0001492 BMDB01492 Gamma-Tocopherol Gamma-Tocopherol, also known as vitaplus e or DL-alpha-tocopherol, belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain. Gamma-Tocopherol exists as a liquid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. DL-alpha-Tocopherol DL-a-Tocopherol DL-Α-tocopherol g-Tocopherol Γ-tocopherol 3,4-Dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol 7,8-Dimethyltocol 7,8-Dimethyltocolo-xylotocopherol Methyltocols O-Xylotocopherol Tocopherol Tocopherols Vitamin e gamma Bioweyxin e-Mulsin Embial GNR-Pharma brand OF tocopherol actetate Organon brand OF tocopherol acetate Schwarzhaupt brand OF tocopherol acetate Snow-e muscle, energy and feritility Spondyvit Tocolion Tocopherol rodisma-med brand Tocopherol worwag brand Togasan vitamin e Unique e Vibolex Vita-e Vitamin e dragees Atarost brand OF tocopherol acetate Biocur brand OF tocopherol acetate Cambridge laboratories brand OF tocopherol actetate Dal e Detulin e Vitamin e EVI-mirale, vitamin-e Elex verla Eplonat Richelet brand OF tocopherol acetate Roche nicholas brand OF tocopherol acetate Rodisma med brand OF tocopherol Sciencex brand OF tocopherol acetate Steigerwald brand OF tocopherol acetate Strathmann brand OF tocopherol Tocopherol grunwalder brand Tocopherol stadapharm brand Verla brand OF tocopherol Vit. e stada VitaPlus e Vitamin-e evi-mirale Vitamine e GNR Vitazell Worwag brand OF tocopherol Alcala brand OF tocopherol acetate Bio e Biopto-e e Vicotrat e-Ferol EUNOVA vitamin e Equivit e Evion Internation animal health brand OF tocopherol acetate MIP brand OF tocopherol acetate Sanum-kehlbeck brand OF tocopherol actetate Tocopherol infirmarius-rovit brand Tocopherol twardy brand Tocovital Vitamin-e dragees Wiedemann brand OF tocopherol Abortosan Arkopharma brand OF tocopherol acetate Dal vita brand OF vitamin e succinate Eu rho brand OF tocopherol Eusovit Infirmarius-rovit brand OF tocopherol Richtavit e Riemser brand OF tocopherol Tocopherol ausrichter brand Tocopherol balkanpharma brand Vitagutt vitamin e Vitamin e natur Vitamin e, togasan Ratiopharm brand OF tocopherol Aliud brand OF tocopherol Bottger brand OF tocopherol acetate Dermorelle e Ferol e-Vitamin-ratiopharm Heyl brand OF tocopherol acetate Kohler brand OF tocopherol Lasar Puncto e Rodisma-med brand OF tocopherol Sanum kehlbeck brand OF tocopherol actetate Scot tussin brand OF tocopherol acetate Stadapharm brand OF tocopherol Tocopa Tocopherol bayer Tocopherol grace brand Tocopherol ratiopharm brand Twardy brand OF tocopherol Uno vit Uno-vit Veyx brand OF tocopherol Vit e hydrosol Vita e Vitamin e al Wiedemann brand OF vitamin e succinate Ausrichter brand OF tocopherol Auxina e Balkanpharma brand OF tocopherol Blackmores brand OF tocopherol Dal-e Davitamon e-Vicotrat Ecoro Ephynal Grunwalder brand OF tocopherol ICN brand OF tocopherol acetate Mucos brand OF tocopherol acetate Tocopherol togal brand Tocopherol verla brand Togal brand OF tocopherol Troyapharm brand OF tocopherol acetate Vita-plus e Vitamin e sanum Vitamin e MP Vitamin emp Woelm brand OF tocopherol acetate Bayer brand OF tocopherol acetate GNR Pharma brand OF tocopherol actetate Grace brand OF tocopherol Malton e Merck brand OF tocopherol acetate Mowivit vitamin e Tocopherol wiedemann brand UnoVit Vitamin e evi mirale Vitamin e suspension Vitamin e, mowivit Vitamin e, vitagutt Vitamin e-MP Adisseo brand OF tocopherol Antioxidans e-hevert Aquasol e AstraZeneca brand OF tocopherol acetate Biosan Dal-vita brand OF vitamin e succinate Dragees, vitamin-e e Mulsin Hervert brand OF tocopherol acetate Hydrovit e Infirmarius rovit brand OF tocopherol Jenapharm brand OF tocopherol Kentucky brand OF tocopherol Micorvit e Sanavitan S Scot-tussin brand OF tocopherol acetate Tocopharm Tocopherol kentucky brand Vita plus e VitaE Medphano brand OF tocopherol acetate VitaminE evimirale C28H48O2 416.6795 416.36543078 2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol 2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-1-benzopyran-6-ol 10191-41-0 CC(C)CCCC(C)CCCC(C)CCCC1(C)CCC2=CC(O)=C(C)C(C)=C2O1 InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h19-22,29H,8-18H2,1-7H3 QUEDXNHFTDJVIY-UHFFFAOYSA-N belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain. Organic compounds Lipids and lipid-like molecules Prenol lipids Quinone and hydroquinone lipids Tocopherols 1-benzopyrans 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Diterpenoids Hydrocarbon derivatives Oxacyclic compounds 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Benzopyran Chromane Diterpenoid Ether Hydrocarbon derivative Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Tocopherol Aromatic heteropolycyclic compounds vitamin E Solid water_solubility 128 mg/mL logp 8.81 ALOGPS logs -7.75 ALOGPS logp 9.99 ChemAxon pka_strongest_acidic 10.47 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol ChemAxon average_mass 416.6795 ChemAxon mono_mass 416.36543078 ChemAxon smiles CC(C)CCCC(C)CCCC(C)CCCC1(C)CCC2=CC(O)=C(C)C(C)=C2O1 ChemAxon formula C28H48O2 ChemAxon inchi InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h19-22,29H,8-18H2,1-7H3 ChemAxon inchikey QUEDXNHFTDJVIY-UHFFFAOYSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 130.33 ChemAxon polarizability 54.13 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::CMs 14964 Specdb::CMs 38095 Specdb::MsMs 81432 Specdb::MsMs 81433 Specdb::MsMs 81434 Specdb::MsMs 142539 Specdb::MsMs 142540 Specdb::MsMs 142541 Adipose Tissue 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 Epidermis 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 Erythrocyte 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 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 Heart 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 Intestine 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 Leukocyte 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 Liver 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 0.0264 +/- 0.00720 uM Raw milk. Holstein. corn silage with concentrates International Dairy Journal; Volume 14, Issue 7, July 2004, Pages 563-570 Milk 0.0744 +/- 0.00960 uM Raw milk. Holstein. Diet: grass silage with concentates International Dairy Journal; Volume 14, Issue 7, July 2004, Pages 563-570 Milk Whole milk 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 Placenta 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 Platelet 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 Prostate Tissue 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 Skeletal Muscle 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 FDB002431 14266 14986 298402 C00007365 2296479 Gamma-Tocopherol 6276 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 Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. 27999311 International Dairy Journal; Volume 14, Issue 7, July 2004, Pages 563-570 BMDBP02253 SEC14-like protein 2 P58875 SEC14L2 Enzyme