Benzoyl glucuronide

Base Information

• Chemical Name: Benzoyl glucuronide
• CAS No.: 19237-53-7
• Molecular Formula: C13H14 O8
• Molecular Weight: 298.249
• UNII: OC94T61O9A
• DSSTox Substance ID: DTXSID90940901
• Nikkaji Number: J619.200I
• Wikidata: Q27285571
• Metabolomics Workbench ID: 40880
• Mol file: 19237-53-7.mol

Synonyms:benzoyl glucuronide

Chemical Property of Benzoyl glucuronide

Chemical Property:

• Vapor Pressure: 1.52E-13mmHg at 25°C
• Refractive Index: 1.639
• Boiling Point: 563.7°Cat760mmHg
• Flash Point: 216.9°C
• PSA: 133.52000
• Density: 1.6g/cm³
• LogP: -1.26440
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 298.06886740
• Heavy Atom Count: 21
• Complexity: 392

Purity/Quality:

Benzoic acid-acyl-b-D-glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)OC2C(C(C(C(O2)C(=O)O)O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C(=O)O)O)O)O
• Uses: Benzoic Acid Acyl-β-D-glucuronide is in the class of 1-β-D-Acyl glucuronides (βGAs) which are potentially highly reactive metabolites which are capable of binding to protein molecules and resulting in adverse drug reactions observed in medications.

Technology Process of Benzoyl glucuronide

There total 1 articles about Benzoyl 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:

O1-benzoyl-β-D-glucopyranuronic acid methyl ester (1000700-92-4) → Benzoic acid glucuronide (19237-53-7) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With Candida antarctica Type B lipase; sodium citrate; In water; dimethyl sulfoxide; at 40 ℃; for 2h; pH=5.0;

DOI:10.1021/jo701547b

Reference yield:

Benzoic acid glucuronide (19237-53-7) → methyl 2,3,4-tri-O-acetyl-1-O-benzoyl-β-D-glucopyranuronate (19237-59-3)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether

2: pyridine

With pyridine; diethyl ether;

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + Benzoic acid glucuronide (19237-53-7) → O1-benzoyl-β-D-glucopyranuronic acid methyl ester (1000700-92-4)

Guidance literature:

With diethyl ether;

upstream raw materials:

O¹-benzoyl-β-D-glucopyranuronic acid methyl ester

Downstream raw materials:

O¹-benzoyl-β-D-glucopyranuronic acid methyl ester

methyl 2,3,4-tri-O-acetyl-1-O-benzoyl-β-D-glucopyranuronate

Refernces