Acetaminophen mercapturate

Base Information

• Chemical Name: Acetaminophen mercapturate
• CAS No.: 52372-86-8
• Molecular Formula: C₁₃H₁₆N₂O₅S
• Molecular Weight: 312.346
• UNII: R86SEU3G6U
• DSSTox Substance ID: DTXSID30966766
• Nikkaji Number: J354.296C
• Wikidata: Q27287959
• Metabolomics Workbench ID: 78521
• Mol file: 52372-86-8.mol

Synonyms:acetaminophen mercapturate;acetaminophen mercapturate monopotassium salt;paracetamol mercapturate

Chemical Property of Acetaminophen mercapturate

Chemical Property:

• Vapor Pressure: 2.73E-18mmHg at 25°C
• Melting Point: 160-163oC
• Refractive Index: 1.625
• Boiling Point: 659.5 °C at 760 mmHg
• PKA: 3.27±0.10(Predicted)
• Flash Point: 352.6 °C
• PSA: 143.86000
• Density: 1.41 g/cm³
• LogP: 0.16120
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 312.07799279
• Heavy Atom Count: 21
• Complexity: 404

Purity/Quality:

99% ^*data from raw suppliers

3-(N-Acetyl-L-cystein-S-yl)Acetaminophen ^*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)NC(=O)C
• Isomeric SMILES: CC(=O)NC1=CC(=C(C=C1)O)SC[C@@H](C(=O)O)NC(=O)C
• Uses: APAP-CYS is a metabolite of acetaminophen (A161220) implicated in nephrotoxicity. Paracetamol Mercapturate is a metabolite of Acetaminophen (A161220) (1,2). Acetaminophen is a widely used analgesic and antipyretic drug. It can also be used in biological study of urinary antihypertensive drug metabolite screening using molecular networking coupled to high-resolution mass spectrometry fragmentation.

Technology Process of Acetaminophen mercapturate

There total 2 articles about Acetaminophen mercapturate 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:

N-Acetylcysteine (7218-04-4,26117-28-2,616-91-1,7696-05-1) + N-acetyl-p-benzoquinoneimine (50700-49-7) → 4-acetaminophenol (103-90-2,8055-08-1) + 2-acetamido-3-(5′-acetamido-2′-hydroxyphenylthio) propanoic acid (60603-13-6,52372-86-8)

Guidance literature:

In water; benzene; at 37 ℃; Product distribution;

DOI:10.1016/S0040-4039(00)71162-2

Reference yield:

→ 2-acetamido-3-(5′-acetamido-2′-hydroxyphenylthio) propanoic acid (60603-13-6,52372-86-8)

Guidance literature:

entspr. Acetanilid 2, N-Acetylcystein;

upstream raw materials:

N-Acetylcysteine

N-acetyl-p-benzoquinoneimine

Refernces