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

• ChemBase ID: 171966
• Molecular Formular: C20H26O3
• Molecular Mass: 314.41864
• Monoisotopic Mass: 314.18819469
• SMILES: C1(=C(C(=O)CCC1(C)C)C)/C=C/C(=C\C=C\C(=C\C(=O)O)\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-NAXRMXIQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,4E,6Z,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: (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
• Synonyms: (2E,4E,6Z,8E)-4-Keto-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoic Acid; 4-Keto-9-cis-tretinoin; 4-Oxo-9-cis-Retinoic Acid; 4-Keto 9-cis Retinoic Acid

Database IDs

• CAS Number: 150737-18-1
• PubChem SID: 164227876
• PubChem CID: 9972939

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: Chloroform; Dichloromethane; Ethanol
• Apperance: Yellow Solid
• Melting Point: 158-160°C

Safety Information

• Storage Condition: Amber Vial, -86°C Freezer, Under Inert Atmosphere
• Storage Warning: Light and Temperature Sensitive

DETAILS

Toronto Research Chemicals - K204960

A metabolite of Retinoic acid.

REFERENCES

• Hoyos, B., et al.: J. Exp. Med.,192, 835 ( 2000), Braungart, E., et al.: J. Invest. Dermatol.,116, 778 (2001)
• Fray, M., et al.: J. Med. Chem., 46, 3514 (2001)
• Ha, M., et al.: Exp. Dermatol., et al.: 13, 543 (2001)