346616

Sigma-Aldrich

1,2-Naphthoquinone

97%

Synonym(s):
β-Naphthoquinone
Empirical Formula (Hill Notation):
C10H6O2
CAS Number:
Molecular Weight:
158.15
Beilstein/REAXYS Number:
606546
EC Number:
MDL number:
PubChem Substance ID:
Pricing and availability is not currently available.

Quality Level

assay

97%

mp

139-142 °C (dec.) (lit.)

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).

Packaging

1, 5 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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...
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)...
Stefan Wirth et al.
Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry, 15(3), 429-440 (2010-01-22)
The synthesis and characterization of three novel iridium(III) complexes and one rhodium(III) complex with 1-nitroso-2-naphthol (3) chelating as a 1,2-naphthoquinone-1-oximato ligand are described. The reaction of mu(2)-halogenido-bridged dimers [(eta(5)-C(5)Me(5))IrX(2)](2) [X is Cl (1a), Br (1b), I (1c)] and [(eta(5)-C(5)Me(5))RhCl(2)](2) (2a)...
Graham M Pumphrey et al.
Microbiology (Reading, England), 153(Pt 11), 3730-3738 (2007-11-03)
This study was designed to characterize naphthalene metabolism in Polaromonas naphthalenivorans CJ2. Comparisons were completed using two archetypal naphthalene-degrading bacteria: Pseudomonas putida NCIB 9816-4 and Ralstonia sp. strain U2, representative of the catechol and gentisate pathways, respectively. Strain CJ2 carries...

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