N-ACETYL-4-BENZOQUINONE IMINE

Base Information

• Chemical Name: N-ACETYL-4-BENZOQUINONE IMINE
• CAS No.: 50700-49-7
• Molecular Formula: C8H7NO2
• Molecular Weight: 149.149
• Hs Code.: 2924299090
• European Community (EC) Number: 640-545-7
• UNII: G6S9BN13TI
• DSSTox Substance ID: DTXSID20198756
• Nikkaji Number: J3.514I
• Wikipedia: N-acetyl-p-benzoquinone_imine,NAPQI
• Wikidata: Q6952342
• Pharos Ligand ID: W4D3WDC3G5MG
• Metabolomics Workbench ID: 54037
• ChEMBL ID: CHEMBL33232
• Mol file: 50700-49-7.mol

Synonyms:Acetamide,N-(4-oxo-2,5-cyclohexadien-1-ylidene)- (9CI);Acetimidoquinone;N-Acetyl-1,4-benzoquinonimine;N-Acetyl-p-benzoquinonimine;NAPQI;

Chemical Property of N-ACETYL-4-BENZOQUINONE IMINE

Chemical Property:

• Appearance/Colour: Yellow Crystalline Solid
• Vapor Pressure: 0.0162mmHg at 25°C
• Melting Point: 74-75 ºC
• Refractive Index: 1.544
• Boiling Point: 255.6 ºC at 760 mmHg
• PKA: -3.37±0.20(Predicted)
• Flash Point: 101.6 ºC
• PSA: 46.50000
• Density: 1.13 g/cm³
• LogP: 0.66900
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly, Sonicated), DMSO (Slightly)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 149.047678466
• Heavy Atom Count: 11
• Complexity: 267

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Acetyl-4-benzoquinone Imine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)N=C1C=CC(=O)C=C1
• Description: N-Acetyl-4-benzoquinone imine (NAPQI) is a cytochrome P450 3A4 and 2E1 metabolite of acetaminophen that can be toxic to the liver when acetaminophen is consumed in large doses. At therapeutic doses of acetaminophen, NAPQI is inactivated by conjugation with glutathione. However, following toxic doses of acetaminophen, available liver reserves of glutathione are quickly depleted due to clearance of excess NAPQI, which enables hepatic proteins to become covalently modified by reactive metabolites and eventually results in hepatocyte necrosis.
• Uses: A toxic metabolite of Acetaminophen, which reacts with serum proteins A toxic metabolite of Acetaminophen (A161220), which reacts with serum proteins. Reactant involved in:? ;Redox reactions1? ;Hydrohalogenation2? ;pH dependent reactions: in acidic media it is hydrolyzed, hydroxylated in alkaline media, and dimerized at intermediate pHs3? ;Mediation of acetaminophen hepatotoxicity4? ;Studies to identify the utility of acetaminophen for treating autoimmune disorders5 N-Acetyl-4-benzoquinone imine (NAPQI) is a cytochrome P450 3A4 and 2E1 metabolite of acetaminophen that can be toxic to the liver when acetaminophen is consumed in large doses. At therapeutic doses of acetaminophen, NAPQI is inactivated by conjugation with glutathione. However, following toxic doses of acetaminophen, available liver reserves of glutathione are quickly depleted due to clearance of excess NAPQI, which enables hepatic proteins to become covalently modified by reactive metabolites and eventually results in hepatocyte necrosis.

Technology Process of N-ACETYL-4-BENZOQUINONE IMINE

There total 10 articles about N-ACETYL-4-BENZOQUINONE IMINE 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: 95.0%

4-acetaminophenol (103-90-2,8055-08-1) → N-acetyl-p-benzoquinoneimine (50700-49-7)

Guidance literature:

With silver(l) oxide;

DOI:10.3109/00498259609046740

Reference yield:

iodoxybenzene (696-33-3) + 4-amino-phenol (123-30-8) → iodosylbenzene (536-80-1) + N-acetyl-p-benzoquinoneimine (50700-49-7)

Guidance literature:

In acetone; Product distribution;

DOI:10.1021/ac00295a037

Reference yield:

N-(pivaloyloxy)-4-methoxyacetanilide (99512-61-5) → methanol (67-56-1) + N-acetyl-p-benzoquinoneimine (50700-49-7)

Guidance literature:

With diclazuril; In water-d2; at 5 ℃; Product distribution; pD = 3.17;

DOI:10.1021/ja00261a019

upstream raw materials:

4-acetaminophenol

N-hydroxy-N-(4-hydroxyphenyl)acetamide

iodoxybenzene

4-amino-phenol

Downstream raw materials:

4-acetaminophenol

S-(5'-Acetamido-2'-hydroxyphenyl)glutathion

2-acetamido-3-(5′-acetamido-2′-hydroxyphenylthio) propanoic acid

N-(4-hydroxy-2-nitrophenyl)-acetamide

Refernces

• 1、 Cheng, Dan,Xu, Wang,Yuan, Lin,Zhang, Xiaobing. "Investigation of Drug-Induced Hepatotoxicity and Its Remediation Pathway with Reaction-Based Fluorescent Probes". . p. 7693 - 7700. Retrieved 2017.
• 2、 Khan, Rajkumar,Mangaiyarkarasi, R.,Pratibha, R.,Premlatha, S.,Umadevi, S.. "Electrochemical performance of a new imidazolium ionic liquid crystal and carbon paste composite electrode for the sensitive detection of paracetamol". . . Retrieved 2020.
• 3、 Shaidarova,Gedmina,Chelnokova,Budnikov. "Selective determination of paracetamol and acetylsalicylic acid on electrode modified with a mixed-valent film of ruthenium oxide-ruthenium cyanide". . p. 620 - 627. Retrieved 2011.
• 4、 Narang, Jagriti,Malhotra, Nitesh,Singh, Sandeep,Singh, Gajendra,Pundir. "Monitoring analgesic drug using sensing method based on nanocomposite". . p. 2396 - 2404. Retrieved 2015.
• 5、 Asghari, Alireza,Ameri, Mohsen,Taghipour, Samira,Ghaderi, Omid. "Facile and clean electrochemical synthesis of new acetaminophen derivatives through electrochemical oxidation of acetaminophen in the presence of thiouracil derivatives". . p. 163 - 172. Retrieved 2017.
• 6、 Kingsley, Mal Phebe,Kalambate, Pramod K.,Srivastava, Ashwini K.. "Simultaneous determination of ciprofloxacin and paracetamol by adsorptive stripping voltammetry using copper zinc ferrite nanoparticles modified carbon paste electrode". . p. 15101 - 15111. Retrieved 2016.
• 7、 Anancia Grace, Arockiajawahar,Dharuman, Venkataraman,Hahn, Jong Hoon. "GdTiO3 perovskite modified graphene composite for electrochemical simultaneous sensing of Acetaminophen and Dopamine". . . Retrieved 2021/08/03.