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346616

Sigma-Aldrich

1,2-Naphthoquinone

97%

Synonym(s):

β-Naphthoquinone

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About This Item

Empirical Formula (Hill Notation):
C10H6O2
CAS Number:
524-42-5
Molecular Weight:
158.15
Beilstein:
606546
EC Number:
208-360-2
MDL number:
MFCD00001698
UNSPSC Code:
12352100
PubChem Substance ID:
24861421

Assay

97%

form

powder

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).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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

Certificates of Analysis (COA)

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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
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
Chao-Jian Chen et al.
Macromolecular rapid communications, 32(14), 1077-1081 (2011-06-16)
A novel comb-like derivative CPEG-g-DNQ was prepared by incorporating light responsive 2-diazo-1,2-naphthoquinone (DNQ) groups into the structure of comb-like poly(ethylene glycol) (CPEG). DLS and TEM results showed that CPEG-g-DNQ self-assembled into spherical micelles with an average size of about 135 nm
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