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

• ChemBase ID: 167863
• Molecular Formular: C15H18O10
• Molecular Mass: 358.29742
• Monoisotopic Mass: 358.08999678
• SMILES: c1(cc(cc(c1)CCC(=O)O)O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: OC(=O)CCc1cc(cc(c1)O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C15H18O10/c16-7-3-6(1-2-9(17)18)4-8(5-7)24-15-12(21)10(19)11(20)13(25-15)14(22)23/h3-5,10-13,15-16,19-21H,1-2H2,(H,17,18)(H,22,23)/t10-,11-,12+,13-,15+/m0/s1
• InChIKey: IITQLVPAMWYCDQ-DKBOKBLXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[3-(2-carboxyethyl)-5-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[3-(2-carboxyethyl)-5-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 3-(3,5-Dihydroxyphenyl)-1-propanoic Acid β-D-Glucuronide; DHPPA β-D-Glucuronide; 3,5-Dihydroxyphenylpropanoic Acid 3-O-β-D-Glucuronide

Database IDs

• PubChem SID: 162261996
• PubChem CID: 71316266

CALCULATED PROPERTIES

• Acid pKa: 3.0007532
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -4.762767
• LogD (pH = 7.4): -7.3144836
• Log P: -0.49936143
• Molar Refractivity: 77.9402 cm^3
• Polarizability: 31.415129 Å^3
• Polar Surface Area: 173.98 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: >114°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D454370

3,5-Dihydroxyphenylpropanoic Acid 3-O-β-D-Glucuronide is a metabolite of alkylresorcinol in plasma, used as biomarkers of whole-grain intake.

REFERENCES

• Linko, A., et al.: Anal. Biochem., 308, 307 (2002)
• Ross, A., et al.: J. Agric. Food Chem., 51, 4111 (2002)
• Linko-Parvinen, A., et al.: J. Nutr., 137, 1137 (2002)