9,10-Phenanthrenequinone

Name: 9,10-Phenanthrenequinone
Brand: ALDRICH
Price: 119 USD
Availability: InStock

95%

Synonym(s):

9,10-Phenanthrenedione

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About This Item

Empirical Formula (Hill Notation):

C₁₄H₈O₂

CAS Number:

84-11-7

Molecular Weight:

208.21

Beilstein/REAXYS Number:

608838

EC Number:

201-515-5

MDL number:

MFCD00001163

UNSPSC Code:

12352103

PubChem Substance ID:

24856622

NACRES:

NA.23

Key Documents

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Quality Level

100

assay

95%

form

powder

mp

209-212 °C (lit.)

SMILES string

O=C1C(=O)c2ccccc2-c3ccccc13

InChI

1S/C14H8O2/c15-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)14(13)16/h1-8H

InChI key

YYVYAPXYZVYDHN-UHFFFAOYSA-N

Gene Information

human ... PTPN1(5770), PTPRC(5788)

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Show Differences

1 of 4

This Item	156507	8.07564	8.20529
Sigma-Aldrich 275034 9,10-Phenanthrenequinone	Sigma-Aldrich 156507 9,10-Phenanthrenequinone	Sigma-Aldrich 8.07564 9,10-Phenanthrenequinone	Sigma-Aldrich 8.20529 9,10-Diphenylanthracene
assay 95%	assay ≥99%	assay ≥99.0% (HPLC)	assay ≥98.0% (HPLC)
form powder	form -	form powder	form powder
mp 209-212 °C (lit.)	mp 209-212 °C (lit.)	mp 203-206 °C	mp 247-252 °C
Quality Level 100	Quality Level 100	Quality Level 200	Quality Level 200
Gene Information human ... PTPN1(5770), PTPRC(5788)	Gene Information human ... PTPN1(5770), PTPRC(5788)	Gene Information -	Gene Information -

General description

The quinones of polycyclic aromatic hydrocarbons are present in abundance in all burnt organic material.[1] On being used to passivate silicon surfaces, it reacts with the dangling bonds on the surface via a heteroatomic Diels-Alder reaction. On account of the Π-electron conjugation, the semi conducting nature of the silicon is unaffected.[2]

Application

9,10-Phenanthrenequinon may be used for high quality passivation on silicon (100) surfaces.[2] Quinones may serve as substrates for a variety of flavoenzymes.[1]

pictograms

GHS07,GHS09

signalword

Warning

hcodes

H319,H400

pcodes

P264 - P273 - P280 - P305 + P351 + P338 - P337 + P313 - P391

Hazard Classifications

Aquatic Acute 1 - Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

473.0 °F

flash_point_c

245 °C

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Mutagenicity of quinones: pathways of metabolic activation and detoxification.

P L Chesis et al.

Proceedings of the National Academy of Sciences of the United States of America, 81(6), 1696-1700 (1984-03-01)

The mutagenicity of various quinones, a class of compounds widely distributed in nature, is demonstrated in the Salmonella TA104 tester strain. The metabolic pathways by which four quinones, menadione, benzo[a]pyrene 3,6-quinone, 9,10-phenanthrenequinone, and danthron, caused mutagenicity in this test system

Electronic structure and band alignment of 9, 10-phenanthrenequinone passivated silicon surfaces

Avasthi, Sushobhan, et al.

Surface Science, 605(13), 1308-1312 (2011)

Redox cycling of 9,10-phenanthraquinone to cause oxidative stress is terminated through its monoglucuronide conjugation in human pulmonary epithelial A549 cells.

Keiko Taguchi et al.

Free radical biology & medicine, 44(8), 1645-1655 (2008-02-26)

9,10-Phenanthraquinone (PQ), a component of airborne particulate matter, causes marked cellular protein oxidation and cytotoxicity through a two-electron reduction to 9,10-dihydroxyphenanthrene (PQH2), which is associated with the propagation of reactive oxygen species (K. Taguchi et al., Free Radic. Biol. Med.

9,10-Phenanthrenequinone induces DNA deletions and forward mutations via oxidative mechanisms in the yeast Saccharomyces cerevisiae.

Chester E Rodriguez et al.

Toxicology in vitro : an international journal published in association with BIBRA, 22(2), 296-300 (2007-10-26)

The estimated cancer risk from diesel exhaust particles (DEP) in the air is approximately 70% of the cancer risk from all air pollutants. DEP is comprised of a complex mixture of chemicals whose carcinogenic potential has not been adequately assessed.

9,10-Phenanthrenequinone promotes secretion of pulmonary aldo-keto reductases with surfactant.

Toshiyuki Matsunaga et al.

Cell and tissue research, 347(2), 407-417 (2012-01-28)

9,10-Phenanthrenequinone (9,10-PQ), a major quinone in diesel exhaust particles, induces apoptosis via the generation of reactive oxygen species (ROS) because of 9,10-PQ redox cycling. We have found that intratracheal infusion of 9,10-PQ facilitates the secretion of surfactant into rat alveolus.

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