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

• ChemBase ID: 163529
• Molecular Formular: C15H16O10
• Molecular Mass: 356.28154
• Monoisotopic Mass: 356.07434671
• SMILES: c1(c(ccc(c1)/C=C/C(=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)/C=C/c1ccc(c(c1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)O
• InChI: InChI=1S/C15H16O10/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/h1-5,10-13,15-16,19-21H,(H,17,18)(H,22,23)/b4-2+/t10-,11-,12+,13-,15+/m0/s1
• InChIKey: BSOMSDFTZKNUHY-ZYZFHZPYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 1093679-73-2
• PubChem SID: 162257664
• PubChem CID: 25171992

CALCULATED PROPERTIES

• Acid pKa: 2.9542038
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -4.8216877
• LogD (pH = 7.4): -7.2732096
• Log P: -0.41883793
• Molar Refractivity: 79.0335 cm^3
• Polarizability: 31.227343 Å^3
• Polar Surface Area: 173.98 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Pale Brown Solid
• Melting Point: >150°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - C080015

A metabolite of Caffeic acid.

REFERENCES

• Zhu, B., et al.: J. Biol. Chem., 269, 292 (1994)
• Azuma, K., et al.: J. Agric. Food Chem., 48, 5496 (1994)
• Stark, T., et al.: J. Agric. Food Chem., 54, 5530 (1994)
• Hensel, A., et al.: Planta Med., 73, 142 (1994)