(2E,4E,6E,8E)-9-[4-(acetyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraen-1-yl acetate

• ChemBase ID: 171265
• Molecular Formular: C24H34O4
• Molecular Mass: 386.52436
• Monoisotopic Mass: 386.24570957
• SMILES: C1(CC(CC(=C1/C=C/C(=C/C=C/C(=C/COC(=O)C)/C)/C)C)OC(=O)C)(C)C
• Canonical SMILES: CC(=O)OC/C=C(/C=C/C=C(/C=C/C1=C(C)CC(CC1(C)C)OC(=O)C)\C)\C
• InChI: InChI=1S/C24H34O4/c1-17(9-8-10-18(2)13-14-27-20(4)25)11-12-23-19(3)15-22(28-21(5)26)16-24(23,6)7/h8-13,22H,14-16H2,1-7H3/b10-8+,12-11+,17-9+,18-13+
• InChIKey: UZQRWSZPFLIVIM-QJGAXEKYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,4E,6E,8E)-9-[4-(acetyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraen-1-yl acetate
• IUPAC Traditional name: (2E,4E,6E,8E)-9-[4-(acetyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraen-1-yl acetate
• Synonyms: 3-(Acetyloxy)-retinol Acetate; rac all-trans 3-(Acetyloxy) Retinol Acetate 90%

Database IDs

• CAS Number: 76686-33-4
• PubChem SID: 164227175
• PubChem CID: 21772456

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.1896253
• LogD (pH = 7.4): 4.1896253
• Log P: 4.1896253
• Molar Refractivity: 117.8959 cm^3
• Polarizability: 44.53173 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H953305

A metabolite of all-trans Retinoic acid.

REFERENCES

• Omiecinski, C., et al.: Cancer Res., 50, 4315 (1990)
• Chapman, D., et al.: Biochem. Pharmacol., 48, 1807 (1990)
• White, J., et al.: J. Biol. Chem., 271, 29922 (1990)
• Chen, H., et al.: Drug Metab. Dispos., 28, 1051 (1990)