methyl (4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoate

• ChemBase ID: 173935
• Molecular Formular: C18H22O6
• Molecular Mass: 334.36368
• Monoisotopic Mass: 334.14163842
• SMILES: c1(c(c(c(c2c1COC2=O)O)C/C=C(/CCC(=O)OC)\C)OC)C
• Canonical SMILES: COC(=O)CC/C(=C/Cc1c(OC)c(C)c2c(c1O)C(=O)OC2)/C
• InChI: InChI=1S/C18H22O6/c1-10(6-8-14(19)22-3)5-7-12-16(20)15-13(9-24-18(15)21)11(2)17(12)23-4/h5,20H,6-9H2,1-4H3/b10-5+
• InChIKey: ZPXRQFLATDNYSS-BJMVGYQFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoate
• IUPAC Traditional name: methyl (4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoate
• Synonyms: (4E)-6-(1,3-Dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic Acid Methyl Ester; Mycophenolic Acid Methyl Ester; EP Impurity E; Methyl Mycophenolate (EP Impurity E)

Database IDs

• CAS Number: 31858-66-9
• PubChem SID: 164229845
• PubChem CID: 6478685

CALCULATED PROPERTIES

• Acid pKa: 9.758773
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.6734679
• LogD (pH = 7.4): 3.6716099
• Log P: 3.6734915
• Molar Refractivity: 90.0025 cm^3
• Polarizability: 34.200127 Å^3
• Polar Surface Area: 82.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: White Solid
• Melting Point: 105-106°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M320540

Degradation product of Mycophenolate mofetil. EP Impurity E.

REFERENCES

• Allison, A., et al.: Immunol. Rev., 136, 5 (1993)
• Anderson, E., et al.: Biocatal. Biotransform., 16(1993)
• 181 (1993)
• Srinivas, T., et al.: Expert. Opin. Pharmacother., 4, 2325 (1993)