(2S,3S,4S,5R,6S)-6-{5-[(1E)-2-carboxyeth-1-en-1-yl]-2-methoxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 171791
• Molecular Formular: C16H18O10
• Molecular Mass: 370.30812
• Monoisotopic Mass: 370.08999678
• SMILES: c1(c(cc(cc1)/C=C/C(=O)O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)OC
• Canonical SMILES: COc1ccc(cc1O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)/C=C/C(=O)O
• InChI: InChI=1S/C16H18O10/c1-24-8-4-2-7(3-5-10(17)18)6-9(8)25-16-13(21)11(19)12(20)14(26-16)15(22)23/h2-6,11-14,16,19-21H,1H3,(H,17,18)(H,22,23)/b5-3+/t11-,12-,13+,14-,16+/m0/s1
• InChIKey: SHJZLGVIOYFHCB-MBAOVNHDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{5-[(1E)-2-carboxyeth-1-en-1-yl]-2-methoxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{5-[(1E)-2-carboxyeth-1-en-1-yl]-2-methoxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 5-(2-Carboxyethenyl)-2-methoxyphenyl β-D-Glucopyranosiduronic Acid; Isoferulic Acid 3-O-β-D-Glucuronide

Database IDs

• CAS Number: 1065272-10-7
• PubChem SID: 164227701
• PubChem CID: 49844484

CALCULATED PROPERTIES

• Acid pKa: 3.0363083
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -4.5139103
• LogD (pH = 7.4): -7.086013
• Log P: -0.27294388
• Molar Refractivity: 83.5158 cm^3
• Polarizability: 33.10129 Å^3
• Polar Surface Area: 162.98 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 174-177°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - I816150

Isoferulic Acid 3-O-β-D-Glucuronide is the glucuronide conjugate of Isoferulic Acid (H946180). Isoferulic Acid 3-O-β-D-Glucuronide is one of the circulating metabolites in human plasma after coffee consumption.

REFERENCES

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