(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol

• ChemBase ID: 177455
• Molecular Formular: C20H30O
• Molecular Mass: 286.4516
• Monoisotopic Mass: 286.22966558
• SMILES: C1(=C(CCCC1(C)C)C)/C=C/C(=C\C=C\C(=C\CO)\C)/C
• Canonical SMILES: OC/C=C(/C=C/C=C(\C=C\C1=C(C)CCCC1(C)C)/C)\C
• InChI: InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8-,17-13+
• InChIKey: FPIPGXGPPPQFEQ-MKOSUFFBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
• IUPAC Traditional name: retinol, 9-cis-
• Synonyms: 9-cis-Retinol; 9-cis-Vitamin A Alcohol; 9-cis-Retinol

Database IDs

• CAS Number: 22737-97-9
• PubChem SID: 164233365
• PubChem CID: 9947823

CALCULATED PROPERTIES

• Acid pKa: 16.43577
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 4.694093
• LogD (pH = 7.4): 4.694093
• Log P: 4.694093
• Molar Refractivity: 97.9234 cm^3
• Polarizability: 36.345623 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichlromethane; Ethyl Acetate
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 82-83°C

Safety Information

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

DETAILS

Toronto Research Chemicals - R252095

A metabolite of Vitamin A.

REFERENCES

• McCormick, A., et al.: J. Biol. Chem., 257(4)
• 1730 (4)
• Buck, J., et al.: Science, 254, 1654 (4)
• Napoli, J., et al.: Chem. Immunol. Immunopathol., 80, S52 (4)