(2S,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 157572
• Molecular Formular: C21H18O13
• Molecular Mass: 478.35982
• Monoisotopic Mass: 478.07474064
• SMILES: c1cc(c(cc1c1c(c(=O)c2c(cc(cc2o1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C(=O)O)O)O)O)O)O
• Canonical SMILES: Oc1cc(O)c2c(c1)oc(c(c2=O)O[C@@H]1O[C@H](C(=O)O)[C@H]([C@@H]([C@H]1O)O)O)c1ccc(c(c1)O)O
• InChI: InChI=1S/C21H18O13/c22-7-4-10(25)12-11(5-7)32-17(6-1-2-8(23)9(24)3-6)18(13(12)26)33-21-16(29)14(27)15(28)19(34-21)20(30)31/h1-5,14-16,19,21-25,27-29H,(H,30,31)/t14-,15-,16+,19-,21+/m0/s1
• InChIKey: DUBCCGAQYVUYEU-ZUGPOPFOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl β-D-Glucopyranosiduronic Acid; Quercetin 3-O-Glucuronide; Quercetin 3-O-β-D-Glucuronopyranoside; Quercetin 3-Glucuronide; Quercetin 3-β-Glucuronide; Quercetin Glucuronide; Quercetin β-Glucuronide; Quercituron; Quercetin 3-O-β-D-Glucuronide; 3,3′,4′,5,7-Pentahydroxyflavone 3-glucuronide; Mikwelianin; Miquelianin; Quercetin 3-O-β-D-glucuronide; Querciturone; Quercetin 3-glucuronide

Database IDs

• CAS Number: 22688-79-5
• MDL Number: MFCD09752939
• PubChem SID: 162251709
• PubChem CID: 5274585

CALCULATED PROPERTIES

• Acid pKa: 2.6505625
• H Acceptors: 13
• H Donor: 8
• LogD (pH = 5.5): -2.6396623
• LogD (pH = 7.4): -4.3444734
• Log P: 0.17543924
• Molar Refractivity: 109.1429 cm^3
• Polarizability: 42.194145 Å^3
• Polar Surface Area: 223.67 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C21H18O13

DETAILS

Toronto Research Chemicals - Q509510

Quercetin 3-O-β-D-Glucuronide is the major metabolite of Quercetin (Q509500).

REFERENCES

• Ajay, M., et al.: Life Sci., 74, 603 (2003)
• Shen, S., et al.: Toxicol. Appl. Pharmacol., 197, 84 (2003)
• Amira, S., et al.: Eur. J. Pharmacol. 599, 126 (2003)