Chloramphenicol glucuronide

Base Information

• Chemical Name: Chloramphenicol glucuronide
• CAS No.: 39751-33-2
• Molecular Formula: C₁₇H₂₀Cl₂N₂O₁₁
• Molecular Weight: 499.259
• UNII: 5N9C7NNS4Q
• DSSTox Substance ID: DTXSID10960343
• Nikkaji Number: J470.597A
• Wikidata: Q82941503
• Mol file: 39751-33-2.mol

Synonyms:chloramphenicol glucuronide

Chemical Property of Chloramphenicol glucuronide

Chemical Property:

• Vapor Pressure: 1.17E-34mmHg at 25°C
• Melting Point: 170-174°C
• Boiling Point: 897.7°C at 760 mmHg
• Flash Point: 496.7°C
• PSA: 211.60000
• Density: 1.71g/cm³
• LogP: -0.26040
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 8
• Exact Mass: 498.0444148
• Heavy Atom Count: 32
• Complexity: 671

Purity/Quality:

97% ^*data from raw suppliers

Chloramphenicol glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(C(COC2C(C(C(C(O2)C(=O)O)O)O)O)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
• Isomeric SMILES: C1=CC(=CC=C1[C@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C(=O)O)O)O)O)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
• Uses: The major glucuronide metabolite of Chloramphenicol (C325030).

Technology Process of Chloramphenicol glucuronide

There total 2 articles about Chloramphenicol 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:

α-D-glucuronyl fluoride (777038-38-7) + chloramphenicol (56-75-7,85666-84-8) → Chloramphenicol 3-O-glucuronide (39751-33-2)

Guidance literature:

With Escherichia coli β-glucuronidase E504G mutant; In aq. phosphate buffer; tert-butyl alcohol; at 37 ℃; for 48h; pH=7.5; Enzymatic reaction;

DOI:10.1039/c4ob00984c

Reference yield:

2,2-dichloro-N-[2-hydroxy-1-hydroxymethyl-2-(4-nitrophenyl)ethyl]acetamide (579-51-1,85666-84-8) + uridine-5'-diphosphoglucuronic acid → chloramphenicol glucuronide (39751-33-2)

Guidance literature:

With glucuronosyl transferase immobilized on Sepharose; phosphate buffer pH 7.8; Ambient temperature;

DOI:10.1021/ac00251a051

upstream raw materials:

α-D-glucuronyl fluoride

chloramphenicol

2,2-dichloro-N-[2-hydroxy-1-hydroxymethyl-2-(4-nitrophenyl)ethyl]acetamide

Refernces

• 1、 Ma, Paul,Kanizaj, Nicholas,Chan, Shu-Ann,Ollis, David L.,McLeod, Malcolm D.. "The Escherichia coli glucuronylsynthase promoted synthesis of steroid glucuronides: Improved practicality and broader scope". supporting information. p. 6208 - 6214. Retrieved 2014/08/05.