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346616

Sigma-Aldrich

1,2-Naphthoquinone

97%

Synonyme(s) :

β-Naphthoquinone

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About This Item

Formule empirique (notation de Hill):
C10H6O2
Numéro CAS:
524-42-5
Poids moléculaire :
158.15
Numéro Beilstein :
606546
Numéro CE :
208-360-2
Numéro MDL:
MFCD00001698
Code UNSPSC :
12352100
ID de substance PubChem :
24861421

Pureté

97%

Forme

powder

Pf

139-142 °C (dec.) (lit.)

Chaîne SMILES 

O=C1C=Cc2ccccc2C1=O

InChI

1S/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H

Clé InChI

KETQAJRQOHHATG-UHFFFAOYSA-N

Informations sur le gène

human ... PTPRC(5788)

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Description générale

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).

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302,H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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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
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
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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