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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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Shingo Arakawa et al.
The Journal of toxicological sciences, 37(3), 595-605 (2012-06-13)
We investigated the role of glutathione S-transferases Mu 1 (GSTM1) in acetaminophen (APAP)-induced hepatotoxicity using Gstm1-null mice. A single oral administration of APAP resulted in a marked increase in plasma alanine aminotransferase accompanied by hepatocyte necrosis 24 hr after administration
Johannes S Hoos et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 859(2), 147-156 (2007-10-05)
A generic method for the detection of covalent adducts to the cysteine-34 residue of human serum albumin (HSA) has been developed, based on an on-line combination of immunoaffinity chromatography for selective sample pre-treatment, solution phase digestion, liquid chromatography and tandem
Jean-Matthieu Prot et al.
Toxicology and applied pharmacology, 259(3), 270-280 (2012-01-11)
We have analyzed transcriptomic, proteomic and metabolomic profiles of hepatoma cells cultivated inside a microfluidic biochip with or without acetaminophen (APAP). Without APAP, the results show an adaptive cellular response to the microfluidic environment, leading to the induction of anti-oxidative
Gregg V Crichlow et al.
Biochemistry, 48(1), 132-139 (2008-12-19)
Macrophage migration inhibitory factor (MIF) is a secreted protein expressed in numerous cell types that counters the antiinflammatory effects of glucocorticoids and has been implicated in sepsis, cancer, and certain autoimmune diseases. Interestingly, the structure of MIF contains a catalytic
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
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