(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

• ChemBase ID: 171969
• Molecular Formular: C20H26O3
• Molecular Mass: 314.41864
• Monoisotopic Mass: 314.18819469
• SMILES: C1CC(=O)C(=C(C1(C)C)/C=C/C(=C/C=C/C(=C\C(=O)O)/C)/C)C
• Canonical SMILES: C/C(=C\C=C\C(=C/C(=O)O)\C)/C=C/C1=C(C)C(=O)CCC1(C)C
• InChI: InChI=1S/C20H26O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13-
• InChIKey: GGCUJPCCTQNTJF-FAOQNJJDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
• IUPAC Traditional name: 4-oxo-13-cis-retinoic acid
• Synonyms: 3,7-Dimethyl-9-(4-keto-2,6,6-trimethyl-1-cyclohexen-1-yl)-2Z,4E,6E,8E-nonatetranenoic Acid; 4-Oxoisotretinoin; Ro 22-6595; 4-Oxo-13-cis-retinoic Acid; 4-Keto 13-cis-Retinoic Acid

Database IDs

• CAS Number: 71748-58-8
• PubChem SID: 164227879
• PubChem CID: 6437087

CALCULATED PROPERTIES

• Acid pKa: 4.996648
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.7256129
• LogD (pH = 7.4): 1.9733462
• Log P: 4.3470845
• Molar Refractivity: 98.484 cm^3
• Polarizability: 36.218983 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Ethanol (slightly); Ether; Ethyl Acetate; Isopropanol
• Apperance: Yellow to Orange Solid
• Melting Point: 150-157°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Moisture, Temperature, Light Sensitive, Store in freezer

DETAILS

Toronto Research Chemicals - K204970

A metabolite of Retinoic acid in neuroblastoma.

REFERENCES

• Andreola, F., et al.: J. Biol. Chem., 279, 3434 (2004)
• Armstrong, J., et al.: Biochem. Pharmacol., 69, 1299 (2004)
• Njar, V., et al.: Bioorg. Med. Chem., 14, 4323 (2004)
• Veal, G., et al.: Br. J. Cancer, 96, 424 (2004)