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
Beilstein:
608838
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.23
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Quality Level
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Aquatic Acute 1 - Eye Irrit. 2
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
473.0 °F
Flash Point(C)
245 °C
Personal Protective Equipment
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.
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
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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