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1,2-Naphthoquinone

Name: 1,2-Naphthoquinone
Brand: ALDRICH

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

GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Precautionary Statements

P261 - P264 - P270 - P301 + P312 - P302 + P352 - P305 + P351 + P338

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

H47003

5-Hydroxy-1,4-naphthoquinone

Scanning electrochemical microscopy of living cells: different redox activities of nonmetastatic and metastatic human breast cells.

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

1,2-Naphthoquinone activates vanilloid receptor 1 through increased protein tyrosine phosphorylation, leading to contraction of guinea pig trachea.

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

Involvement of sensory nerves and TRPV1 receptors in the rat airway inflammatory response to two environment pollutants: diesel exhaust particles (DEP) and 1,2-naphthoquinone (1,2-NQ).

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

Linking oxidative events to inflammatory and adaptive gene expression induced by exposure to an organic particulate matter component.

Wan-Yun Cheng et al.

Environmental health perspectives, 120(2), 267-274 (2011-10-15)

Toxicological studies have correlated inflammatory effects of diesel exhaust particles (DEP) with its organic constituents, such as the organic electrophile 1,2-naphthoquinone (1,2-NQ). To elucidate the mechanisms involved in 1,2-NQ-induced inflammatory responses, we examined the role of oxidant stress in 1,2-NQ-induced

GSH-mediated S-transarylation of a quinone glyceraldehyde-3-phosphate dehydrogenase conjugate.

Takashi Miura et al.

Chemical research in toxicology, 24(11), 1836-1844 (2011-08-11)

Many cellular proteins with reactive thiols form covalent bonds with electrophiles, thereby modifying their structures and activities. Here, we describe the recovery of a glycolytic protein, glyceraldehyde-3-phosphate dehydrogenase (GAPDH), from such an electrophilic attack by 1,2-napthoquinone (1,2-NQ). GAPDH readily formed

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