275034
9,10-Phenanthrenequinone
95%
Synonym(s):
9,10-Phenanthrenedione
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About This Item
Empirical Formula (Hill Notation):
C14H8O2
CAS Number:
Molecular Weight:
208.21
UNSPSC Code:
12352103
NACRES:
NA.23
PubChem Substance ID:
EC Number:
201-515-5
Beilstein/REAXYS Number:
608838
MDL number:
Assay:
95%
Form:
powder
InChI key
YYVYAPXYZVYDHN-UHFFFAOYSA-N
InChI
1S/C14H8O2/c15-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)14(13)16/h1-8H
SMILES string
O=C1C(=O)c2ccccc2-c3ccccc13
assay
95%
form
powder
Quality Level
Gene Information
human ... PTPN1(5770), PTPRC(5788)
mp
209-212 °C (lit.)
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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.
signalword
Warning
hcodes
Hazard Classifications
Aquatic Acute 1 - Eye Irrit. 2
Storage Class
11 - Combustible Solids
wgk
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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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)
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.
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.
Toshiyuki Matsunaga et al.
Free radical research, 45(7), 848-857 (2011-06-01)
9,10-Phenanthrenequinone (9,10-PQ), a redox-active quinone in diesel exhausts, triggers cellular apoptosis via reactive oxygen species (ROS) generation in its redox cycling. This study found that induction of CCAAT/enhancer-binding protein-homologous protein (CHOP), a pro-apoptotic factor derived from endoplasmic reticulum stress, participates
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