disodium (2E)-3-[4-(sulfonatooxy)phenyl]prop-2-enoate

• ChemBase ID: 164997
• Molecular Formular: C9H6Na2O6S
• Molecular Mass: 288.18488
• Monoisotopic Mass: 287.96804747
• SMILES: c1c(ccc(c1)/C=C/C(=O)[O-])OS(=O)(=O)[O-].[Na+].[Na+]
• Canonical SMILES: [O-]C(=O)/C=C/c1ccc(cc1)OS(=O)(=O)[O-].[Na+].[Na+]
• InChI: InChI=1S/C9H8O6S.2Na/c10-9(11)6-3-7-1-4-8(5-2-7)15-16(12,13)14;;/h1-6H,(H,10,11)(H,12,13,14);;/q;2*+1/p-2/b6-3+
• InChIKey: ZBEAEMLBRSACIO-RRHCXGJISA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (2E)-3-[4-(sulfonatooxy)phenyl]prop-2-enoate
• IUPAC Traditional name: disodium (2E)-3-[4-(sulfonatooxy)phenyl]prop-2-enoate
• Synonyms: 3-[4-(Sulfooxy)phenyl]-2-propenoic Acid Disodium Salt; p-Coumaric Acid Sulfate Disodium Salt; p-Coumaric Acid 4-O-Sulfate Disodium Salt

Database IDs

• CAS Number: 308338-96-7
• PubChem SID: 162259130
• PubChem CID: 71314998

CALCULATED PROPERTIES

• Acid pKa: -2.2078419
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -3.196707
• LogD (pH = 7.4): -4.444095
• Log P: 1.3572075
• Molar Refractivity: 64.748 cm^3
• Polarizability: 21.438616 Å^3
• Polar Surface Area: 106.56 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: >279°C (Dec.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C755375

p-Coumaric Acid 4-O-Sulfate is the sulfate conjugate of p-Coumaric Acid. p-Coumaric Acid 4-O-Sulfate is one of the metabolites in human biological fluids after coffee consumption. p-Coumaric Acid 4-O-Sulfate is also a metabolite of 4-Nonylphenol (N650430)

REFERENCES

• Fumeaux, R. et al.: Org. Biomol. Chem., 8, 5199 (2010)
• Zalko, D. et al.: Drug Metab. Disp., 31, 168 (2010)
• Thibaut, R. et al.: Xenobiotica, 28, 745 (2010)