346616
1,2-Naphthoquinone
97%
Synonym(s):
β-Naphthoquinone
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About This Item
Empirical Formula (Hill Notation):
C10H6O2
CAS Number:
Molecular Weight:
158.15
Beilstein/REAXYS Number:
606546
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
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assay
97%
form
powder
mp
139-142 °C (dec.) (lit.)
functional group
ketone
SMILES string
O=C1C=Cc2ccccc2C1=O
InChI
1S/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H
InChI key
KETQAJRQOHHATG-UHFFFAOYSA-N
Gene Information
human ... PTPRC(5788)
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General description
1,2-Naphthoquinone is one of the major metabolite of naphthalene, which is responsible for the cytotoxicity and genotoxicity associated with it. 1,2-Naphthoquinone is an atmospheric contaminant. It causes the contraction of trachea smooth muscles in guinea pig through the activation of epidermal growth factor receptor. 1,2-Naphthoquinone has been reported as an environmental quinone in diesel exhaust particles (DEP) and atmospheric particulate matter.
Application
1,2-Naphthoquinone was employed as mediator during electrochemical mapping of redox activity in normal human breast (MCF-10A) cells by scanning electrochemical microscopy (SECM).
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Suramya Waidyanatha et al.
Chemico-biological interactions, 141(3), 189-210 (2002-10-19)
Naphthalene-1,2-oxide (NPO), 1,2-naphthoquinone (1,2-NPQ) and 1,4-naphthoquinone (1,4-NPQ) are the major metabolites of naphthalene that are thought to be responsible for the cytotoxicity and genotoxicity of this chemical. We measured cysteinyl adducts of these metabolites in hemoglobin (Hb) and albumin (Alb)
B Liu et al.
Proceedings of the National Academy of Sciences of the United States of America, 97(18), 9855-9860 (2000-08-30)
Electrochemical methods have been widely used to monitor physiologically important molecules in biological systems. This report describes the first application of the scanning electrochemical microscope (SECM) to probe the redox activity of individual living cells. The possibilities of measuring the
Shota Kikuno et al.
Toxicology and applied pharmacology, 210(1-2), 47-54 (2005-07-26)
1,2-Naphthoquinone (1,2-NQ) has recently been identified as an environmental quinone in diesel exhaust particles (DEP) and atmospheric PM2.5. We have found that this quinone is capable of causing a concentration-dependent contraction of tracheal smooth muscle in guinea pigs with EC50
Soraia K P Costa et al.
Archives of toxicology, 84(2), 109-117 (2009-04-29)
The environmental chemical 1,2-naphthoquinone (1,2-NQ) is implicated in the exacerbation of airways diseases induced by exposure to diesel exhaust particles (DEP), which involves a neurogenic-mediated mechanism. Plasma extravasation in trachea, main bronchus and lung was measured as the local (125)I-bovine
Yasuhiro Shinkai et al.
Chemical research in toxicology, 25(6), 1222-1230 (2012-05-17)
1,2-Naphthoquinone (1,2-NQ) is an atmospheric chemical capable of (1) redox cycling with electron donors and (2) covalent modification of nucleophilic groups on proteins. In the present study, we investigated its interaction with the redox protein, thioredoxin1 (Trx1), which led to
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