(2Z,4E,6E)-7-(4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-yl)-3-methylocta-2,4,6-trienoic acid

• ChemBase ID: 168131
• Molecular Formular: C20H28O3
• Molecular Mass: 316.43452
• Monoisotopic Mass: 316.20384476
• SMILES: C1CCC2(C(=CC(/C(=C/C=C/C(=C\C(=O)O)/C)/C)O2)C1(C)C)C
• Canonical SMILES: OC(=O)/C=C(\C=C\C=C(\C1C=C2C(O1)(C)CCCC2(C)C)/C)/C
• InChI: InChI=1S/C20H28O3/c1-14(12-18(21)22)8-6-9-15(2)16-13-17-19(3,4)10-7-11-20(17,5)23-16/h6,8-9,12-13,16H,7,10-11H2,1-5H3,(H,21,22)/b8-6+,14-12-,15-9+
• InChIKey: QDOSIDVGVRAXSE-DYIZZJGFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z,4E,6E)-7-(4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-yl)-3-methylocta-2,4,6-trienoic acid
• IUPAC Traditional name: (2Z,4E,6E)-7-(4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl)-3-methylocta-2,4,6-trienoic acid
• Synonyms: (2Z,4E,6E)-7-(2,4,5,6,7,7a-Hexahydro-4,4,7a-trimethyl-2-benzofuranyl)-3-methyl-2,4,6-octatrienoic Acid; 13-cis-5,8-Epoxy-5,8-dihydroretinoic Acid; 5,8-Epoxy-13-cis Retinoic Acid(Mixture of Diastereomers)

Database IDs

• CAS Number: 112018-12-9
• PubChem SID: 162262263
• PubChem CID: 71316382

CALCULATED PROPERTIES

• Acid pKa: 4.64343
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.357271
• LogD (pH = 7.4): 1.5798651
• Log P: 4.2694936
• Molar Refractivity: 96.3973 cm^3
• Polarizability: 36.347374 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Pale Yellow Solid
• Melting Point: 186-188°C

Safety Information

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

DETAILS

Toronto Research Chemicals - E589820

A metabolite of 13-cis-Retinoic Acid (R250000).

REFERENCES

• Samokyszyn, V., et al.: J. Biol. Chem., 262, 14119 (1987)
• Oldfield, N., et al.: Drug Metabol. Dispos., 18, 1105 (1987)
• Samokyszyn, V., et al.: Chem. Res. Toxicol., 10, 795 (1987)