(2Z,4E,6E,8E)-9-[4-(2H3)methoxy-2,3,6-trimethylphenyl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid

• ChemBase ID: 159524
• Molecular Formular: C21H26O3
• Molecular Mass: 326.42934
• Monoisotopic Mass: 326.18819469
• SMILES: c1(c(c(cc(c1/C=C/C(=C/C=C/C(=C\C(=O)O)/C)/C)C)OC)C)C
• Canonical SMILES: COc1cc(C)c(c(c1C)C)/C=C/C(=C/C=C/C(=C\C(=O)O)/C)/C
• InChI: InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12-
• InChIKey: IHUNBGSDBOWDMA-UGOGCBOOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z,4E,6E,8E)-9-[4-(^2H₃)methoxy-2,3,6-trimethylphenyl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid
• IUPAC Traditional name: (2Z,4E,6E,8E)-9-[4-(^2H₃)methoxy-2,3,6-trimethylphenyl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid
• Synonyms: 9-(4-Methoxy-d3-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic Acid, 13-cis-Etretin-d3, Isoacitretin-d3, Isoetretin-d3, Ro 13-7652-d3; 13-cis Acitretin-d3

Database IDs

• PubChem SID: 162253659
• PubChem CID: 46780079

CALCULATED PROPERTIES

• Acid pKa: 5.011076
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.976502
• LogD (pH = 7.4): 3.2266924
• Log P: 5.5870485
• Molar Refractivity: 104.1665 cm^3
• Polarizability: 38.03137 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Yellow Solid
• Melting Point: 178-180°C

Safety Information

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

DETAILS

Toronto Research Chemicals - A189927

A deuterated synthetic retinoid which is the major metabolite of etretinate (E938000).

REFERENCES

• Sato, T., et al.: J. Med. Chem., 51, 7705 (2008)
• Liu, X., et al.: Cancer Chemother. Pharmacol., 63, 167 (2008)