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A7300

Sigma-Aldrich

N-Acetylbenzoquinoneimine

Synonym(s):

N-(4-Oxo-1-cyclohexa-2,5-dienylidene)acetamide, N-Acetyl-p-benzo-quinoneimine, NAPQI

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About This Item

Empirical Formula (Hill Notation):
C8H7NO2
CAS Number:
50700-49-7
Molecular Weight:
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000365449
0000365449
0000320642
SLCR6515
0000253151

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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
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
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
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
Jeffrey L Woodhead et al.
The Journal of pharmacology and experimental therapeutics, 342(2), 529-540 (2012-05-18)
N-acetylcysteine (NAC) is the treatment of choice for acetaminophen poisoning; standard 72-h oral or 21-h intravenous protocols are most frequently used. There is controversy regarding which protocol is optimal and whether the full treatment course is always necessary. It would
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