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

• ChemBase ID: 167385
• Molecular Formular: C15H18O10
• Molecular Mass: 358.29742
• Monoisotopic Mass: 358.08999678
• SMILES: c1(c(ccc(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)CCc1ccc(c(c1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)O
• InChI: InChI=1S/C15H18O10/c16-7-3-1-6(2-4-9(17)18)5-8(7)24-15-12(21)10(19)11(20)13(25-15)14(22)23/h1,3,5,10-13,15-16,19-21H,2,4H2,(H,17,18)(H,22,23)/t10-,11-,12+,13-,15+/m0/s1
• InChIKey: AELQNMHOLDHBFA-DKBOKBLXSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 1187945-71-6
• PubChem SID: 162261518
• PubChem CID: 49844972

CALCULATED PROPERTIES

• Acid pKa: 3.0131598
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -4.7382774
• LogD (pH = 7.4): -7.305055
• Log P: -0.49936143
• Molar Refractivity: 77.9402 cm^3
• Polarizability: 31.41649 Å^3
• Polar Surface Area: 173.98 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Warm Water
• Apperance: Pale Brown Solid
• Melting Point: 165-168°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - D448705

Dihydro Caffeic Acid 3-O-β-D-Glucuronide is a glucuronide metabolite of Caffeic Acid (C080000).

REFERENCES

• Clifford, M., et al.: J .Agric. Food Chem., 53, 3821 (2005)
• Lafay, S., et al.: J. Nutr., 136, 1192 (2005)
• Poquet, L., et al.: Drug Metab. Dispos., 36, 190 (2005)