3-(Cystein-S-yl)paracetamol

Base Information

• Chemical Name: 3-(Cystein-S-yl)paracetamol
• CAS No.: 53446-10-9
• Molecular Formula: C₁₁H₁₄N₂O₄S
• Molecular Weight: 270.309
• UNII: 6Q2X58Y8BP
• DSSTox Substance ID: DTXSID70201608
• Nikkaji Number: J247.941I
• Metabolomics Workbench ID: 71637
• ChEMBL ID: CHEMBL3785905
• Mol file: 53446-10-9.mol

Synonyms:3-(cystein-S-yl)acetaminophen;3-(cystein-S-yl)paracetamol

Chemical Property of 3-(Cystein-S-yl)paracetamol

Chemical Property:

• Vapor Pressure: 1.54E-12mmHg at 25°C
• Melting Point: 190-193°C dec.
• Boiling Point: 541.1°Cat760mmHg
• Flash Point: 281°C
• PSA: 175.25000
• Density: 1.44g/cm³
• LogP: 2.26120
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Aqueous Base (Slightly), DMSO (Slightly, Sonicated), Methanol (Slightly)
• XLogP3: -2.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 270.06742811
• Heavy Atom Count: 18
• Complexity: 313

Purity/Quality:

99% ^*data from raw suppliers

3-Cysteinylacetaminophen Trifluoroacetic Acid Salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1=CC(=C(C=C1)O)SCC(C(=O)O)N
• Isomeric SMILES: CC(=O)NC1=CC(=C(C=C1)O)SC[C@@H](C(=O)O)N
• Uses: APAP-CYS is a metabolite of Acetaminophen implicated in nephrotoxicity.

Technology Process of 3-(Cystein-S-yl)paracetamol

There total 3 articles about 3-(Cystein-S-yl)paracetamol 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:

3-(5-Acetylamino-2-benzyloxy-phenylsulfanyl)-2-benzyloxycarbonylamino-propionic acid (37398-29-1) → 3-(S)-Cysteinylacetaminophen (37398-30-4,53446-10-9)

Guidance literature:

With boron trifluoride diethyl etherate; trifluoroacetic acid;

DOI:10.1139/v72-326

Reference yield:

3-(5-Acetylamino-2-benzyloxy-phenylsulfanyl)-2-benzyloxycarbonylamino-propionic acid methyl ester (37398-28-0) → 3-(S)-Cysteinylacetaminophen (37398-30-4,53446-10-9)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH

2: BF₃-Et₂O, CF₃CO₂H

With sodium hydroxide; boron trifluoride diethyl etherate; trifluoroacetic acid;

DOI:10.1139/v72-326

Reference yield:

→ 3-(S)-Cysteinylacetaminophen (37398-30-4,53446-10-9)

Guidance literature:

entspr. Acetanilid 2, Cysteinhydrochlorid;

upstream raw materials:

3-(5-Acetylamino-2-benzyloxy-phenylsulfanyl)-2-benzyloxycarbonylamino-propionic acid

3-(5-Acetylamino-2-benzyloxy-phenylsulfanyl)-2-benzyloxycarbonylamino-propionic acid methyl ester