(2E,4E,6E,8E)-9-(3-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid

• ChemBase ID: 171263
• Molecular Formular: C20H28O3
• Molecular Mass: 316.43452
• Monoisotopic Mass: 316.20384476
• SMILES: C1(CCC(C(=C1/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C)C)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/C20H28O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13,18,21H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+
• InChIKey: KGUMXGDKXYTTEY-FRCNGJHJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,4E,6E,8E)-9-(3-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
• IUPAC Traditional name: 4-hydroxyretinoic acid
• Synonyms: 4-Hydroxy-all-trans-retinoic Acid; 4-Hydroxyretinoic Acid; rac all-trans 4-Hydroxy Retinoic Acid

Database IDs

• CAS Number: 66592-72-1
• PubChem SID: 164227173
• PubChem CID: 6438629

CALCULATED PROPERTIES

• Acid pKa: 4.996648
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.162085
• LogD (pH = 7.4): 1.4098185
• Log P: 3.7835567
• Molar Refractivity: 99.3063 cm^3
• Polarizability: 36.76783 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: N/A

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H953300

A metabolite of all-trans Retinoic acid (R250200).

REFERENCES

• Idres, N., et al.: Cancer Res., 61, 700 (2001)
• Taimi, M., et al.: J. Biol. Chem., 279, 77 (2001)
• Vermot, J., et al.: Science, 308, 563 (2001)