86674-49-9

Usage

Uses

Used in Environmental Monitoring and Research:
1-nitropyrene-3-ol is used as a biomarker for monitoring air pollution levels and assessing the genotoxic potential of particulate matter in the atmosphere. Its presence in air samples can provide valuable information on the sources and distribution of genotoxic pollutants, aiding in the development of strategies to reduce exposure and mitigate their harmful effects on human health and the environment.
Used in Toxicology Studies:
1-nitropyrene-3-ol serves as a model compound in toxicology research, helping scientists to understand the mechanisms of genotoxicity and carcinogenicity associated with nitroarene exposure. By studying its interactions with biological systems, researchers can gain insights into the molecular pathways and processes that contribute to the toxic effects of air pollutants, ultimately leading to the identification of potential targets for intervention and prevention.
Used in Analytical Chemistry:
1-nitropyrene-3-ol can be employed as a reference material in the development and validation of analytical methods for the detection and quantification of genotoxic compounds in environmental and biological samples. Its unique chemical properties make it a suitable candidate for the calibration of instruments and the optimization of extraction and detection techniques, ensuring accurate and reliable measurements in various applications.

InChI:InChI=1/C16H9NO3/c18-14-8-13(17(19)20)11-6-4-9-2-1-3-10-5-7-12(14)16(11)15(9)10/h1-8,18H

Upstream product

• 75321-20-9 1,3-dinitropyrene 
• 78751-40-3 pyren-1-yl acetate 

Downstream Products

• 99026-65-0 1-Acetamidopyren-3-ol 

Relevant academic research and scientific papers

Photodegradation mechanisms of 1-nitropyrene, an environmental pollutant: The effect of organic solvents, water, oxygen, phenols, and polycyclic aromatics on the destruction and product yields

This work describes studies of the photodegradation mechanism of 1-nitropyrene (1-NO2Py) in a chemical model system consisting of an organic solvent and known constituents of an aerosol particle. Photoproducts such as 1-hydroxypyrene (1-OHPy),

Role of O-acetyltransferase in activation of oxidised metabolites of the genotoxic environmental pollutant 1-nitropyrene

The genotoxic environmental contaminant 1-nitropyrene is metabolised in mammalian systems by pathways more complex than the straightforward nitroreduction which accounts for most of its biological activity in bacteria. In order to evaluate the role of O-acetyltransferase (OAT) activity in generation of genotoxic intermediates from 1-nitropyrene, the mutagenicity of the major primary oxidised metabolites of 1-nitropyrene was characterised in the Ames Salmonella typhimurium plate incorporation assay with strain TA98, and with variants of TA98 deficient (TA98/1,8-DNP6) or enhanced (YG1024) in O-acetyltransferase. 1-Nitropyren-3-ol was more mutagenic in the absence than in the presence of S9, while 1-nitropyren-4-ol, 1-nitropyren-6-ol and 1-nitropyren-8-ol required S9 for maximum expression of mutagenicity. 1-Nitropyren-4-ol (176 rev/nmol without S9, 467 rev/nmol with S9 in TA98) and 1-nitropyren-6-ol (13 rev/nmol without S9, 266 rev/nmol with S9 in TA98) were overall the most potent nitropyrenol isomers assayed. 1-Acetamidopyren-8-ol and 1-acetamidopyrene 4,5-quinone were only minimally active. 1-Acetamidopyren-3-ol exhibited direct-acting mutagenicity. 1-Acetamidopyren-6-ol, previously shown to be a major contributor to mutagenicity in the urines of rats dosed with 1-nitropyrene (Ball et al., 1984b), was confirmed as a potent (359 rev/nmol) S9-dependent mutagen. Both the direct-acting and the S9-dependent mutagenicity of all the compounds studied was enhanced in the OAT-overproducing strain and much diminished (though not always entirely lost) in the OAT-deficient strain, showing that OAT amplifies expression of the genotoxicity of these compounds. 1-Acetamidopyren-6-ol required both S9 and OAT activity in order to exhibit any mutagenicity; this finding strongly implicates N-hydroxylation followed by O-esterification, as opposed to further S9-catalyzed ring oxidation, as a major route of activation for urinary metabolites of 1-nitropyrene.

Chemical Oxidation of Nitrated Polycyclic Aromatic Hydrocarbons: Hydroxylation with Superoxide Anion Radical

Nitrated polycyclic aromatic hydrocarbon (nitroPAH) is a potent mutagen which is reductively and/or oxidatively metabolized. Biological oxidation of nitroPAH, such as hydroxylation and epoxidation, is known, but chemical oxidation has been reported in only a few papers. NitroPAH is barely oxidized by various chemical oxidants because of the electron deficient property of the aromatic ring with the nitro substituent. Nucleophilic reactivity of superoxide anion radical is known, and thus the oxidation of nitroPAH with the chemically generated superoxide anion radical was carried out in this study. When 1-nitropyrene was reacted with KO2/18-crown-6 in dimethylformamide, 5-, 6-, 8-, and 9-hydroxy-1-nitropyrenes and 1-hydroxypyrene were obtained in preparative yields. Three isomeric dinitropyrenes, 3-nitrofluoranthene, 6-nitrobenzopyrene, and 6-nitrochrysene, were oxidized to hydroxy derivatives, some of which correspond to the oxidative metabolite of nitroPAH. The oxidation of dinitropyrenes with trifluoroperacetic acid gave K-region oxidized products.

Determination of nitrated polynuclear aromatic hydrocarbons in particulate extracts by capillary column gas chromatography with nitrogen selective detection

The highly complex matrix of a diesel particulate extract was analyzed for nitrated polynuclear aromatic hydrocarbons (nitro-PAH) by use of fused-silica capillary column GC/thermionic nitrogen-phosphorus (GC/NPD) analysis of HPLC fractions. These samples were found to contain at least 100 nitro-PAH. Positive isomer identification for 17 nitro-PAH has been made utilizing the GC retention times of authentic standards and low- and high-resolution mass spectra as criteria. An additional 45 nitro-PAH were tentatively identified by using one or more of these techniques. Quantitative GC/MS analysis of 1-nitropyrene, 1,3-dinitropyrene, 1,6-di-nitropyrene, and 1,8-dinitropyrene was facilitated by the use of perdeuterated analogues of these compounds as internal standards. Detection limits by the GC/NPD method range between 0. 2 and 0. 5 ppm for the HPLC fractionated samples.