(2S,3S,4S,5R,6S)-6-[5-(2-carboxyethyl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 167573
• Molecular Formular: C16H20O10
• Molecular Mass: 372.324
• Monoisotopic Mass: 372.10564684
• SMILES: c1(c(cc(cc1)CCC(=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)CCC(=O)O
• InChI: InChI=1S/C16H20O10/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/h2,4,6,11-14,16,19-21H,3,5H2,1H3,(H,17,18)(H,22,23)/t11-,12-,13+,14-,16+/m0/s1
• InChIKey: OSJGZCUHTGTJHT-JHZZJYKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[5-(2-carboxyethyl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[5-(2-carboxyethyl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 5-(2-Carboxyethyl)-2-methoxyphenyl β-D-Glucopyranosiduronic Acid; Dihydroisoferulic Acid 3-O-Glucuronide; Dihydro Isoferulic Acid 3-O-β-D-Glucuronide

Database IDs

• CAS Number: 1187945-72-7
• PubChem SID: 162261706
• PubChem CID: 49844034

CALCULATED PROPERTIES

• Acid pKa: 3.0922236
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -4.4347825
• LogD (pH = 7.4): -7.111768
• Log P: -0.35346738
• Molar Refractivity: 82.4225 cm^3
• Polarizability: 33.289215 Å^3
• Polar Surface Area: 162.98 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 128-140°C

Safety Information

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

DETAILS

Toronto Research Chemicals - D448940

Dihydroisoferulic Acid 3-O-β-D-Glucuronide is the glucuronide conjugate of Dihydroisoferulic Acid (H946365). Dihydroisoferulic Acid 3-O-β-D-Glucuronide is a minor circulating metabolite in human plasma after ingestion of coffee and can be used as a biomar

REFERENCES

• Fumeaux, R. et al.: Org. Biomol. Chem., 8, 5199 (2010)
• Stalmach, A. et al.: Drug Metab. Disp., 37, 1749 (2010)