(2E)-3-[4-(2H3)methoxy-3-(sulfooxy)phenyl]prop-2-enoic acid

• ChemBase ID: 171794
• 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-(^2H₃)methoxy-3-(sulfooxy)phenyl]prop-2-enoic acid
• IUPAC Traditional name: (2E)-3-[4-(^2H₃)methoxy-3-(sulfooxy)phenyl]prop-2-enoic acid
• Synonyms: 3-[4-(Methoxy-d3)-3-(sulfooxy)phenyl]-2-propenoic Acid Disodium Salt; Isoferulic Acid-d3 3-O-Sulfate Disodium Salt

Database IDs

• PubChem SID: 164227704
• PubChem CID: 71749557

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: 24.228989 Å^3
• Polar Surface Area: 110.13 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 202-205°C

Safety Information

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

DETAILS

Toronto Research Chemicals - I816162

Labelled Isoferulic Acid 3-O-Sulfate,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)