(2E)-3-[3-hydroxy-4-(2H3)methoxyphenyl]prop-2-enoic acid

• ChemBase ID: 170744
• Molecular Formular: C10H10O4
• Molecular Mass: 194.184
• Monoisotopic Mass: 194.0579088
• SMILES: c1(c(cc(cc1)/C=C/C(=O)O)O)OC
• Canonical SMILES: COc1ccc(cc1O)/C=C/C(=O)O
• InChI: InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+
• InChIKey: QURCVMIEKCOAJU-HWKANZROSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-3-[3-hydroxy-4-(^2H₃)methoxyphenyl]prop-2-enoic acid
• IUPAC Traditional name: (2E)-3-[3-hydroxy-4-(^2H₃)methoxyphenyl]prop-2-enoic acid
• Synonyms: 3-[3-Hydroxy-4-(methoxy-d3)phenyl]acrylic Acid; Isoferulic Acid; 3-[3-Hydroxy-4-(methoxy-d3)phenyl]-2-propenoic Acid; 3-Hydroxy-4-methoxycinnamic Acid-d3 (Isoferulic Acid-d3)

Database IDs

• CAS Number: 1028203-97-5
• PubChem SID: 164226654
• PubChem CID: 71749120

CALCULATED PROPERTIES

• Acid pKa: 3.7674725
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.058786187
• LogD (pH = 7.4): -1.6036878
• Log P: 1.6748496
• Molar Refractivity: 51.504 cm^3
• Polarizability: 19.350763 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 229-231°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H946182

Labelled 3-Hydroxy-4-methoxycinnamic Acid (Isoferulic acid), a hypoglycemic agent.

REFERENCES

• Liu, I.-M., et al.: J. Pharmacol. Exp. Ther., 307, 1196 (2003)