(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)nona-2,4,6,8-tetraen-1-ol

• ChemBase ID: 165692
• Molecular Formular: C20H28O
• Molecular Mass: 284.43572
• Monoisotopic Mass: 284.21401552
• SMILES: C1C=CC(=C(C1(C)C)/C=C/C(=C/C=C/C(=C/CO)/C)/C)C
• Canonical SMILES: OC/C=C(/C=C/C=C(/C=C/C1=C(C)C=CCC1(C)C)\C)\C
• InChI: InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6-13,21H,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
• InChIKey: XWCYDHJOKKGVHC-OVSJKPMPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)nona-2,4,6,8-tetraen-1-ol
• IUPAC Traditional name: vitamin A 2
• Synonyms: (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2,4,6,8-nonatetraen-1-ol; 3,4-Dehydroretinol; all-trans- 3-Dehydroretinol; Dehydroretinol; Vitamin A2; all-trans-3,4-Didehydroretinol; 3-Dehydro Retinol

Database IDs

• CAS Number: 79-80-1
• PubChem SID: 162259825
• PubChem CID: 6436043

CALCULATED PROPERTIES

• Acid pKa: 16.43577
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 4.3321714
• LogD (pH = 7.4): 4.3321714
• Log P: 4.3321714
• Molar Refractivity: 99.04 cm^3
• Polarizability: 36.115406 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Thick Orange Gel

Safety Information

• Storage Condition: Hygroscopic, -86°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D230100

Naturally occurring retinoid originally discovered in livers of freshwater fish. Constitutes 20-25% of total retinoid content in human epidermis; levels are markedly elevated in patients with hyperproliferative dermatoses such as psoriasis.

REFERENCES

• Garling, D., et al.: J. Nutr., 106, 1368 (1976)
• Bravo, R., et al.: Nature, 326, 515 (1976)
• Takeuchi, T., et al.: Aquaculture, 169, 155 (1976)
• Rollman, O., et al.: Biochem. J., 293, 675 (1976)
• Funkenstein, B., et al.: Comp. Biochem. Physiol., 129B, 613