(2E)-3-[4-methoxy-3-(sulfooxy)phenyl]prop-2-enoic acid

• ChemBase ID: 171793
• Molecular Formular: C10H10O7S
• Molecular Mass: 274.2472
• Monoisotopic Mass: 274.01472366
• SMILES: c1(c(cc(cc1)/C=C/C(=O)O)OS(=O)(=O)O)OC
• Canonical SMILES: COc1ccc(cc1OS(=O)(=O)O)/C=C/C(=O)O
• InChI: InChI=1S/C10H10O7S/c1-16-8-4-2-7(3-5-10(11)12)6-9(8)17-18(13,14)15/h2-6H,1H3,(H,11,12)(H,13,14,15)/b5-3+
• InChIKey: DCMKMHVTKFJMAU-HWKANZROSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-3-[4-methoxy-3-(sulfooxy)phenyl]prop-2-enoic acid
• IUPAC Traditional name: (2E)-3-[4-methoxy-3-(sulfooxy)phenyl]prop-2-enoic acid
• Synonyms: 3-[4-Methoxy-3-(sulfooxy)phenyl]-2-propenoic Acid; Isoferulic Acid 3-O-Sulfate

Database IDs

• CAS Number: 1258842-19-1
• PubChem SID: 164227703
• PubChem CID: 71749556

CALCULATED PROPERTIES

• Acid pKa: -2.1997883
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -3.4282417
• LogD (pH = 7.4): -4.6173325
• Log P: 1.1995363
• Molar Refractivity: 61.4958 cm^3
• Polarizability: 24.228119 Å^3
• Polar Surface Area: 110.13 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I816160

Isoferulic Acid 3-O-Sulfate is the sulfate conjugate of Isoferulic Acid (H946180). Isoferulic Acid 3-O-Sulfate is one of the circulating metabolites in human plasma after consumption of coffee.

REFERENCES

• Fumeaux, R. et al.: Org. Biomol. Chem., 8, 5199 (2010)
• Redeuil, K. et al.: J. Chrom. A, 1218, 4678 (2010)