Showing Metabocard for 13-hydroxy-gamma-tocopherol (BASm0007239)
| Common Name | 13-hydroxy-gamma-tocopherol |
|---|---|
| Description | 13'-hydroxy-r-tocopherol is a precursor of dehydrogenation to form 13'-Carboxy-gamma-tocopherol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. r-Tocopherol provides different antioxidant activities in food and in-vitro studies and showed higher activity in trapping lipophilic electrophiles and reactive nitrogen and oxygen species. From the metabolism end product, only that of r-tocopherol (2,7,8-trimethyl-2-(b-carboxyethyl)-6-hydroxychroman), but not that of a-tocopherol, was identified to provide natriuretic activity. Only the r-tocopherol plasma level served as biomarker for cancer and cardiovascular risk. |
| Structure | |
| Molecular Formula | C28H48O3 |
| Average Mass | 432.67890 |
| Monoisotopic Mass | 432.36035 |
| IUPAC Name | (2R)-2-[(4S,8R)-13-hydroxy-4,8,12-trimethyltridecyl]-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-6-ol |
| Traditional Name | (2r)-2-[(4s,8r)-13-hydroxy-4,8,12-trimethyltridecyl]-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-6-ol |
| CAS Registry Number | Not Available |
| SMILES | Cc1c(O)cc2c(c1C)O[C@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)CO)CC2 |
| InChI Identifier | InChI=1S/C28H48O3/c1-20(12-8-13-22(3)19-29)10-7-11-21(2)14-9-16-28(6)17-15-25-18-26(30)23(4)24(5)27(25)31-28/h18,20-22,29-30H,7-17,19H2,1-6H3/t20-,21+,22?,28-/m1/s1 |
| InChI Key | QNBPVJMQPAQXML-SLGTZZLGSA-N |
| CHEBI ID | CHEBI:84963 |
| HMDB ID | HMDB0012561 |
| State | Not Available |
| Water Solubility | 3.28e-05 g/l |
| logP | 8.05 |
| logS | -7.12 |
| pKa (Strongest Acidic) | 10.47 |
| pKa (Strongest Basic) | -1.74 |
| Hydrogen Acceptor Count | 3 |
| Hydrogen Donor Count | 2 |
| Polar Surface Area | 49.69 Ų |
| Rotatable Bond Count | 13 |
| Physiological Charge | 0 |
| Formal Charge | 0 |
| Refractivity | 132.18 m³·mol⁻¹ |
| Polarizability | 55.09 |