(2E,4E,6E,8E)-3,7-dimethyl-9-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}nona-2,4,6,8-tetraenoic acid

• ChemBase ID: 168128
• Molecular Formular: C20H28O3
• Molecular Mass: 316.43452
• Monoisotopic Mass: 316.20384476
• SMILES: C1(CCCC2(C1(/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C)O2)C)(C)C
• Canonical SMILES: C/C(=C\C=C\C(=C\C(=O)O)\C)/C=C/C12OC2(C)CCCC1(C)C
• InChI: InChI=1S/C20H28O3/c1-15(8-6-9-16(2)14-17(21)22)10-13-20-18(3,4)11-7-12-19(20,5)23-20/h6,8-10,13-14H,7,11-12H2,1-5H3,(H,21,22)/b9-6+,13-10+,15-8+,16-14+
• InChIKey: KEEHJLBAOLGBJZ-WEDZBJJJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,4E,6E,8E)-3,7-dimethyl-9-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}nona-2,4,6,8-tetraenoic acid
• IUPAC Traditional name: (2E,4E,6E,8E)-3,7-dimethyl-9-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}nona-2,4,6,8-tetraenoic acid
• Synonyms: 5,6-Epoxy-5,6-dihydroretinoic Acid; 5,6-Epoxyretinoic Acid; all-trans 5,6-Epoxy Retinoic Acid

Database IDs

• CAS Number: 13100-69-1
• PubChem SID: 162262260
• PubChem CID: 5363137

CALCULATED PROPERTIES

• Acid pKa: 4.9366875
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.872786
• LogD (pH = 7.4): 2.1115441
• Log P: 4.5405703
• Molar Refractivity: 96.5225 cm^3
• Polarizability: 36.347374 Å^3
• Polar Surface Area: 49.83 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 160-162°C

Safety Information

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

DETAILS

Toronto Research Chemicals - E589800

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)