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Key Documents

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A7300

Sigma-Aldrich

N-Acetylbenzoquinoneimine

Sinónimos:

N-(4-oxo-1-cyclohexa-2,5-dienylidene)acetamide, N-Acetyl-p-benzo-quinone imine, NAPQI

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About This Item

Fórmula empírica (notación de Hill):
C8H7NO2
Número de CAS:
50700-49-7
Peso molecular:
149.15
MDL number:
MFCD00078909
UNSPSC Code:
12352100
PubChem Substance ID:
57653880
NACRES:
NA.22

form

solid

Quality Level

100

storage temp.

−70°C

SMILES string

CC(=O)\N=C1\C=CC(=O)C=C1

InChI

1S/C8H7NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5H,1H3

InChI key

URNSECGXFRDEDC-UHFFFAOYSA-N

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Application

Reactant involved in:
  • Redox reactions
  • Hydrohalogenation
  • pH dependent reactions: in acidic media it is hydrolyzed, hydroxylated in alkaline media, and dimerized at intermediate pHs
  • Mediation of acetaminophen hepatotoxicity
  • Studies to identify the utility of acetaminophen for treating autoimmune disorders

Other Notes

Acetaminophen metabolite that reacts with serum proteins.

Caution

air, moisture and light sensitive

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Paracetamol British Pharmacopoeia (BP) Reference Standard

BP371

Paracetamol

Sigma-Aldrich

Sigma-Aldrich

270733

Agua

Acetaminophen analytical standard

Sigma-Aldrich

A3035

Acetaminophen

Acetaminophen BioXtra, ≥99.0%

Sigma-Aldrich

A7085

Acetaminophen

Angela S Burke et al.
Chemical research in toxicology, 23(7), 1286-1292 (2010-06-29)
Acetaminophen (APAP) toxicity in primary mouse hepatocytes occurs in two phases. The initial phase (0-2 h) occurs with metabolism to N-acetyl-p-benzoquinoneimine which depletes glutathione, and covalently binds to proteins, but little toxicity is observed. Subsequent washing of hepatocytes to remove
Laura P James et al.
Drug metabolism and disposition: the biological fate of chemicals, 37(8), 1779-1784 (2009-05-15)
Acetaminophen (APAP)-induced liver toxicity occurs with formation of APAP-protein adducts. These adducts are formed by hepatic metabolism of APAP to N-acetyl-p-benzoquinone imine, which covalently binds to hepatic proteins as 3-(cystein-S-yl)-APAP adducts. Adducts are released into blood during hepatocyte lysis. We
Amaresh Kumar Sahoo et al.
Nanoscale, 3(10), 4226-4233 (2011-09-08)
Herein, we report the generation of a composite comprised of p-hydroxyacetanilide dimer and Ag nanoparticles (NPs) by reaction of AgNO(3) and p-hydroxyacetanilide. The formation of the composite was established by UV-vis, FTIR and NMR spectroscopy, transmission electron microscopy and X-ray
Hui Ting Chng et al.
Journal of biomolecular screening, 17(7), 974-986 (2012-05-31)
The zebrafish model has been increasingly explored as an alternative model for toxicity screening of pharmaceutical drugs. However, little is understood about the bioactivation of drug to reactive metabolite and phase I and II metabolism of chemical in zebrafish as
Cross-linking of protein molecules by the reactive metabolite of acetaminophen, N-acetyl-p-benzoquinone imine, and related quinoid compounds.
A J Streeter et al.
Advances in experimental medicine and biology, 197, 727-737 (1986-01-01)
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