ChemicalBook > CAS DataBase List > N-ACETYL-4-BENZOQUINONE IMINE

N-ACETYL-4-BENZOQUINONE IMINE

Product Name
N-ACETYL-4-BENZOQUINONE IMINE
CAS No.
50700-49-7
Chemical Name
N-ACETYL-4-BENZOQUINONE IMINE
Synonyms
napqi;N-Acetylimidoquinone;N-ACETYL-P-BENZOQUINONE IMINE;N-Acetyl-p-benzoquinonimine;Chebi:29132;acetimidoquinone;n-acetyl-p-quinonimine;N-ACETYLBENZOQUINONE-IMINE;N-ACETYL-PARA-QUINONEIMINE;N-acrtyl Benzoquinoneimine
CBNumber
CB0696629
Molecular Formula
C8H7NO2
Formula Weight
149.15
MOL File
50700-49-7.mol
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N-ACETYL-4-BENZOQUINONE IMINE Property

Melting point:
74-75
Boiling point:
255.6±43.0 °C(Predicted)
Density 
1.13±0.1 g/cm3(Predicted)
storage temp. 
-70°C
solubility 
Chloroform (Slightly, Sonicated), DMSO (Slightly)
form 
Solid
pka
-3.37±0.20(Predicted)
color 
Pale Yellow to Very Dark Red
Stability:
Temperature, Moisture, Light, and Oxygen Sensitive
CAS DataBase Reference
50700-49-7
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Safety

WGK Germany 
3
RTECS 
AC6960000
HS Code 
2902110000
Toxicity
LD50 i.p. in male BALB/c mice: 20 mg/kg (Dahlin, Nelson)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
A7300
Product name
N-Acetylbenzoquinoneimine
Packaging
1mg
Price
$315
Updated
2024/03/01
Sigma-Aldrich
Product number
A7300
Product name
N-Acetylbenzoquinoneimine
Packaging
5mg
Price
$1240
Updated
2024/03/01
Cayman Chemical
Product number
16115
Product name
N-Acetyl-4-benzoquinone imine
Purity
≥90%
Packaging
500μg
Price
$117
Updated
2024/03/01
Cayman Chemical
Product number
16115
Product name
N-Acetyl-4-benzoquinone imine
Purity
≥90%
Packaging
1mg
Price
$222
Updated
2024/03/01
Cayman Chemical
Product number
16115
Product name
N-Acetyl-4-benzoquinone imine
Purity
≥90%
Packaging
5mg
Price
$923
Updated
2024/03/01
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N-ACETYL-4-BENZOQUINONE IMINE Chemical Properties,Usage,Production

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.

Chemical Properties

Yellow Crystalline Solid

Uses

A toxic metabolite of Acetaminophen, which reacts with serum proteins

Uses

A toxic metabolite of Acetaminophen (A161220), which reacts with serum proteins.

Uses

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

Uses

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.

Definition

ChEBI: N-acetyl-1,4-benzoquinone imine is a quinone imine and a ketoimine. It is functionally related to a 1,4-benzoquinone imine.

N-ACETYL-4-BENZOQUINONE IMINE Preparation Products And Raw materials

Raw materials

Preparation Products

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N-ACETYL-4-BENZOQUINONE IMINE Suppliers

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50700-49-7, N-ACETYL-4-BENZOQUINONE IMINERelated Search:


  • N-ACETYLBENZOQUINONE-IMINE
  • N-ACETYL-4-BENZOQUINONE IMINE
  • N-ACETYL-P-BENZOQUINONE IMINE
  • N-N-Acetyl-4-benzoquinone Imine
  • N-ACETYL-PARA-QUINONEIMINE
  • napqi
  • N-Acetyl-p-benzoquinone imine (NAPQI), 98%
  • 4-(Acetylimino)-2,5-cyclohexadien-1-one
  • N-Acetyl-p-benzoquinonimine
  • N-(4-Oxo-1-cyclohexa-2,5-dienylidene)acetamide, N-Acetyl-p-benzo-quinone imine, NAPQI
  • N-Acetyl-1,4-benzoquinone imine
  • Chebi:29132
  • N-(4-Oxocyclohexa-2,5-dien-1-ylidene)acetamide
  • N-(4-Oxo-1-cyclohexa-2,5-dienylidene)acetamide
  • Phenylephrine Impurity 23(N-Acetyl-4-Benzoquinone Imine)
  • N-acrtyl Benzoquinoneimine
  • 4-acetylimino-5-cyclohexadien-1-one
  • acetimidoquinone
  • n-(4-oxo-2,5-cyclohexadien-1-ylidene)-acetamid
  • n-(4-oxo-2,5-cyclohexadien-1-ylidene)acetamide
  • n-(4-oxo-2,5-cyclohexadienylidene)acetamide
  • n-acetyl-p-quinonimine
  • N-Acetylimidoquinone
  • Phenylephrine Impurity 7 (N-Acetyl-4-Benzoquinone Imine)
  • Acetamide, N-(4-oxo-2,5-cyclohexadien-1-ylidene)-
  • 50700-49-7
  • 50600-49-7
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