Showing Metabocard for beta-tocopherol (BASm0002209)
| Common Name | Beta-tocopherol |
|---|---|
| Description | beta-Tocopherol is an antioxidant which is synthesized by photosynthetic organisms and plays an important role in human and animal nutrition. beta-Tocopherols can be oxidized in dry CH2Cl2 or CH3CN by one electron to form cation radicals that deprotonate to form the neutral phenoxyl radicals, which are then immediately further oxidized by one electron to the phenoxonium cations (an ECE electrochemical mechanism, where E signifies an electron transfer and C represents a chemical step, with the electrochemical mechanism having been determined by in situ spectroscopic analysis). The phenoxonium cation of beta-tocopherol is stable for several minutes (PMID: 16771430 ). beta-Tocopherol has been identified in the human placenta (PMID: 32033212 ). |
| Structure | |
| Molecular Formula | C28H48O2 |
| Average Mass | 416.67950 |
| Monoisotopic Mass | 416.36543 |
| IUPAC Name | (2R)-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol |
| Traditional Name | Β-tocopherol |
| CAS Registry Number | 148-03-8 |
| SMILES | Cc1cc(O)c(C)c2c1O[C@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)CC2 |
| InChI Identifier | InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-24(6)26(29)19-23(5)27(25)30-28/h19-22,29H,8-18H2,1-7H3/t21-,22-,28-/m1/s1 |
| InChI Key | WGVKWNUPNGFDFJ-DQCZWYHMSA-N |
| CHEBI ID | CHEBI:47771 |
| HMDB ID | HMDB0006335 |
| State | Not Available |
| Water Solubility | 7.26e-06 g/l |
| logP | 8.81 |
| logS | -7.76 |
| pKa (Strongest Acidic) | 10.47 |
| pKa (Strongest Basic) | -4.85 |
| Hydrogen Acceptor Count | 2 |
| Hydrogen Donor Count | 1 |
| Polar Surface Area | 29.46 Ų |
| Rotatable Bond Count | 12 |
| Physiological Charge | 0 |
| Formal Charge | 0 |
| Refractivity | 130.33 m³·mol⁻¹ |
| Polarizability | 53.32 |