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Key Documents

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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20 EA
CN¥3,850.41

CN¥3,850.41


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20 EA
CN¥3,850.41

About This Item

Empirical Formula (Hill Notation):
C8H7NO2
CAS Number:
Molecular Weight:
149.15
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

CN¥3,850.41


Available to ship onApril 27, 2025Details


Request a Bulk Order

form

solid

Quality Level

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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1 of 4

This Item
853086853001852164
form

powder

form

powder

form

powder

form

powder

assay

≥98% (TLC)

assay

≥98% (TLC)

assay

≥98% (TLC)

assay

≥85.0% (acidimetric), ≥98% (TLC), ≥98.0% (HPLC)

product line

Novabiochem®

product line

Novabiochem®

product line

Novabiochem®

product line

Novabiochem®

storage temp.

2-30°C

storage temp.

2-30°C

storage temp.

2-30°C

storage temp.

15-25°C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

reaction suitability

reaction type: Boc solid-phase peptide synthesis

reaction suitability

reaction type: Boc solid-phase peptide synthesis

reaction suitability

reaction type: Boc solid-phase peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

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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    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
    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

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