Showing Metabocard for all-trans-violaxanthin (BASm0001934)
| Common Name | All-trans-violaxanthin |
|---|---|
| Description | Violaxanthin belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Xanthophylls arise by oxygenation of the carotene backbone. Thus, violaxanthin is considered to be an isoprenoid lipid molecule. Violaxanthin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Violaxanthin is an orange-coloured pigment that is found in brown algae and various plants (e.g. pansies). It is biosynthesized from the epoxidation of zeaxanthin. Violaxanthin is a food additive that is only approved for use in Australia and New Zealand (INS: 161e) (PMID: 29890662 ). |
| Structure | |
| Molecular Formula | C40H56O4 |
| Average Mass | 600.88400 |
| Monoisotopic Mass | 600.41786 |
| IUPAC Name | (1R,6R)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol |
| Traditional Name | (1r,6r)-6-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(1s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol |
| CAS Registry Number | 126-29-4 |
| SMILES | CC(/C=C/C=C(C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C)=C\C=C\C=C(C)\C=C\C=C(C)\C=C\[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C |
| InChI Identifier | InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-39-35(5,6)25-33(41)27-37(39,9)43-39)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(42)28-38(40,10)44-40/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t33-,34-,37+,38+,39-,40-/m0/s1 |
| InChI Key | SZCBXWMUOPQSOX-WVJDLNGLSA-N |
| CHEBI ID | CHEBI:35288 |
| HMDB ID | HMDB0003101 |
| State | Not Available |
| Water Solubility | 5.68e-04 g/l |
| logP | 8.33 |
| logS | -6.02 |
| pKa (Strongest Acidic) | 14.84 |
| pKa (Strongest Basic) | -2.74 |
| Hydrogen Acceptor Count | 4 |
| Hydrogen Donor Count | 2 |
| Polar Surface Area | 65.52 Ų |
| Rotatable Bond Count | 10 |
| Physiological Charge | 0 |
| Formal Charge | 0 |
| Refractivity | 192.33 m³·mol⁻¹ |
| Polarizability | 74.63 |