Quercetin 3-glucuronide

Base Information

• Chemical Name: Quercetin 3-glucuronide
• CAS No.: 22688-79-5
• Molecular Formula: C₂₁H₁₈O₁₃
• Molecular Weight: 478.366
• European Community (EC) Number: 805-253-8
• ChEMBL ID: CHEMBL1506682
• Metabolomics Workbench ID: 64556,123563
• Wikidata: Q104252968
• Wikipedia: Miquelianin
• Mol file: 22688-79-5.mol

Synonyms:miquelianin;quercetin 3-O-beta-D-glucopyranoside;quercetin 3-O-beta-glucopyranoside;quercetin 3-O-glucopyranoside;querciturone

Chemical Property of Quercetin 3-glucuronide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 193～195℃
• Boiling Point: 927.8°C at 760 mmHg
• PKA: 2.76±0.70(Predicted)
• Flash Point: 325.8°C
• PSA: 227.58000
• Density: 1.96g/cm³
• LogP: -0.44660
• Storage Temp.: ?20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 4
• Exact Mass: 478.07474062
• Heavy Atom Count: 34
• Complexity: 830

Purity/Quality:

≥98% ^*data from raw suppliers

Quercetin3-O-β-D-Glucuronide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)C(=O)O)O)O)O)O)O
• Description: Quercetin 3-O-glucuronide is a pharmacologically active flavonol glucuronide isolated from H. perforatum (St. John’s wort) that inhibits the α2c adrenergic receptor (Ki = 4,060 nM in hα2c preparations). Quercetin 3-O-glucuronide (0.6 mg/kg) reduced the time rats spent immobile in the forced swim test, suggesting antidepressant-like properties, when given either acutely or chronically. It also reduced open field stress-induced hyperthermia in mice (at 1.2 mg/kg).
• Uses: Quercetin 3-O-β-D-Glucuronide is the major metabolite of Quercetin (Q509500).

Technology Process of Quercetin 3-glucuronide

There total 22 articles about Quercetin 3-glucuronide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

5,7-bisbenzyloxy-2-(3,4-bisbenzyloxyphenyl)-3-(β-D-glucopyranosyloxy)-4H-chromen-4-one (1332833-27-8) → quercetin 3-O-β-D-glucuronopyranoside (22688-79-5,74336-89-3)

Guidance literature:

5,7-bisbenzyloxy-2-(3,4-bisbenzyloxyphenyl)-3-(β-D-glucopyranosyloxy)-4H-chromen-4-one; With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammomium bromide; potassium carbonate; potassium bromide; In dichloromethane; for 1h;

With 10% palladium hydroxide on charcoal; hydrogen; In tetrahydrofuran; ethanol; for 12h;

DOI:10.1016/j.tetlet.2011.06.108

Reference yield:

(2S,3S,4S,5R,6S)-6-[5,7-Bis-benzyloxy-2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-4-oxo-4H-chromen-3-yloxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid → quercetin 3-O-β-D-glucuronopyranoside (22688-79-5,74336-89-3)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1016/S0040-4039(02)01264-9

Reference yield:

2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-trihydroxychromen-4-one (357194-03-7) → quercetin 3-O-β-D-glucuronopyranoside (22688-79-5,74336-89-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 54 percent / K₂CO₃ / dimethylformamide

2: K₂CO₃ / dimethylformamide

3: MeONa; Amberlite 120 H⁽¹⁺⁾ / methanol

4: NaOCl; TEMPO; NaBr / 2 h

5: hydrogen / palladium on charcoal

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; Amberlite 120 H⁽¹⁺⁾; hydrogen; sodium methylate; potassium carbonate; sodium bromide; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(02)01264-9

upstream raw materials:

quercetol

7,4’-di-O-benzylquercetin

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-trihydroxychromen-4-one

Downstream raw materials:

D-glucuronic acid

quercetol

D-glucuronic acid