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275034

Sigma-Aldrich

9,10-Phenanthrenequinone

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

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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General description

The quinones of polycyclic aromatic hydrocarbons are present in abundance in all burnt organic material. 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.

Application

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

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

hcodes

H319,H400

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

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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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)
Petr Milko et al.
Inorganic chemistry, 48(24), 11734-11742 (2009-11-26)
With the use of the model complexes [(PQ)FeCl(CH(3)O)](+), [(phen)FeCl(CH(3)O)](+), and [(PQ)(phen)FeCl(CH(3)O)](+), where PQ is 9,10-phenanthraquinone and phen is 1,10-phenanthroline, the reactivity of phenanthraquinone in complexes with iron(III) is investigated. It is shown that 9,10-phenanthraquinone takes part in redox processes occurring
Naoya Kishikawa et al.
Talanta, 85(1), 809-812 (2011-06-08)
9,10-Phenanthrenequinone (PQ) is harmful environmental pollutant that is detected in airborne particulates. The measurement of PQ in the air should be necessary to evaluate the potential adverse effects of PQ on human health. We have recently developed a determination method
Michael C Byrns et al.
Biochemical pharmacology, 75(2), 484-493 (2007-10-24)
Aldo-keto reductase (AKR) 1C3 (type 2 3alpha-HSD, type 5 17beta-HSD, and prostaglandin F synthase) regulates ligand access to steroid hormone and prostaglandin receptors and may stimulate proliferation of prostate and breast cancer cells. NSAIDs are known inhibitors of AKR1C enzymes.
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