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192-97-2 | BENZO[E]PYRENE
CAS No: 192-97-2 Catalog No: AG002FL9 MDL No:MFCD00003605
Product Description
Catalog Number:
AG002FL9
Chemical Name:
BENZO[E]PYRENE
CAS Number:
192-97-2
Molecular Formula:
C20H12
Molecular Weight:
252.3093
MDL Number:
MFCD00003605
IUPAC Name:
benzo[e]pyrene
InChI:
InChI=1S/C20H12/c1-2-8-16-15(7-1)17-9-3-5-13-11-12-14-6-4-10-18(16)20(14)19(13)17/h1-12H
InChI Key:
TXVHTIQJNYSSKO-UHFFFAOYSA-N
SMILES:
c1ccc2c(c1)c1cccc3c1c1c2cccc1cc3
EC Number:
205-892-7
UNII:
63APT6398R
NSC Number:
89273
RTECS Number:
DJ4200000
UN Number:
3077
Properties
Complexity:
336
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
252.094g/mol
Formal Charge:
0
Heavy Atom Count:
20
Hydrogen Bond Acceptor Count:
0
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
252.316g/mol
Monoisotopic Mass:
252.094g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
0A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
6.4
Literature
| Title | Journal |
|---|---|
| Inhibition of the formation of benzo[a]pyrene adducts to DNA in A549 lung cells exposed to mixtures of polycyclic aromatic hydrocarbons. | Toxicology in vitro : an international journal published in association with BIBRA 20160901 |
| Successful validation of genomic biomarkers for human immunotoxicity in Jurkat T cells in vitro. | Journal of applied toxicology : JAT 20150701 |
| Pressurized liquid extraction of diesel and air particulate standard reference materials: effect of extraction temperature and pressure. | Analytical chemistry 20121002 |
| Aryl hydrocarbon receptor-independent up-regulation of intracellular calcium concentration by environmental polycyclic aromatic hydrocarbons in human endothelial HMEC-1 cells. | Environmental toxicology 20120901 |
| Changes in thyroid peroxidase activity in response to various chemicals. | Journal of environmental monitoring : JEM 20120801 |
| Influence of earthworm activity on microbial communities related with the degradation of persistent pollutants. | Environmental toxicology and chemistry 20120401 |
| Polycyclic aromatic hydrocarbons (PAHs) in vegetables and fruits produced in Saudi Arabia. | Bulletin of environmental contamination and toxicology 20120401 |
| Seasonal variation for the ratio of BaP to BeP at different sites in Great Xiamen Bay. | Journal of environmental monitoring : JEM 20120401 |
| [Compositions and diagnostic ratios of heavily degraded crude oil residues in contaminated soil in oilfields]. | Huan jing ke xue= Huanjing kexue 20120401 |
| Automobile tires--a potential source of highly carcinogenic dibenzopyrenes to the environment. | Environmental science & technology 20120320 |
| Ah-receptor-independent stimulation of hepatoma 27 culture cell proliferation by polycyclic aromatic hydrocarbons. | Biochemistry. Biokhimiia 20120201 |
| Potent phototoxicity of marine bunker oil to translucent herring embryos after prolonged weathering. | PloS one 20120101 |
| Validation of the Candida albicans delayed-type hypersensitivity (DTH) model in the female B₆C₃F₁ mouse for use in immunotoxicological investigations. | Journal of immunotoxicology 20120101 |
| Micronucleus frequency in children exposed to biomass burning in the Brazilian Legal Amazon region: a control case study. | BMC oral health 20120101 |
| Controlled human wood smoke exposure: oxidative stress, inflammation and microvascular function. | Particle and fibre toxicology 20120101 |
| Effects of hydroquinone on retinal and vascular cells in vitro. | Indian journal of ophthalmology 20120101 |
| Traffic-related air pollution and DNA damage: a longitudinal study in Taiwanese traffic conductors. | PloS one 20120101 |
| Benzo[e]pyrene skeleton dipyrylium dication with a strong donor-acceptor-donor interaction, and its two-electron reduced molecule. | Chemistry (Weinheim an der Bergstrasse, Germany) 20111209 |
| Cardiac toxicity of 5-ring polycyclic aromatic hydrocarbons is differentially dependent on the aryl hydrocarbon receptor 2 isoform during zebrafish development. | Toxicology and applied pharmacology 20111201 |
| Improved efficiency of extraction of polycyclic aromatic hydrocarbons (PAHs) from the National Institute of Standards and Technology (NIST) Standard Reference Material Diesel Particulate Matter (SRM 2975) using accelerated solvent extraction. | Analytical and bioanalytical chemistry 20111201 |
| Aryl hydrocarbon receptor-dependent induction of the IgA receptor FcαRI by the environmental contaminant benzo(a)pyrene in human macrophages. | Toxicology 20111128 |
| Reduced cytochrome P4501A activity and recovery from oxidative stress during subchronic benzo[a]pyrene and benzo[e]pyrene treatment of rainbow trout. | Toxicology and applied pharmacology 20110701 |
| Biodegradation of polycyclic aromatic hydrocarbons by a halotolerant bacterial strain Ochrobactrum sp. VA1. | Marine pollution bulletin 20110201 |
| Osteosarcomagenesis: modeling cancer initiation in the mouse. | Sarcoma 20110101 |
| In vitro toxicity of particulate matter (PM) collected at different sites in the Netherlands is associated with PM composition, size fraction and oxidative potential--the RAPTES project. | Particle and fibre toxicology 20110101 |
| Influence of temperature and origin of dissolved organic matter on the partitioning behavior of polycyclic aromatic hydrocarbons. | Environmental science and pollution research international 20100601 |
| Inhibition of apoptosis in human retinal pigment epithelial cells treated with benzo(e)pyrene, a toxic component of cigarette smoke. | Investigative ophthalmology & visual science 20100501 |
| Malondialdehyde-modified low density lipoprotein (MDA-LDL)-induced cell growth was suppressed by polycyclic aromatic hydrocarbons (PAHs). | The Journal of toxicological sciences 20100401 |
| Navajo coal combustion and respiratory health near Shiprock, New Mexico. | Journal of environmental and public health 20100101 |
| Antioxidant airway responses following experimental exposure to wood smoke in man. | Particle and fibre toxicology 20100101 |
| 3-methylcholanthrene and benzo(a)pyrene modulate cardiac cytochrome P450 gene expression and arachidonic acid metabolism in male Sprague Dawley rats. | British journal of pharmacology 20091201 |
| Oligothiophene functionalized dimethyldihydropyrenes I: syntheses and photochromicity. | The Journal of organic chemistry 20090904 |
| Inhibition of human mesenchymal stem cell-derived adipogenesis by the environmental contaminant benzo(a)pyrene. | Toxicology in vitro : an international journal published in association with BIBRA 20090901 |
| Effects of benzo(e)pyrene on the retinal neurosensory cells and human microvascular endothelial cells in vitro. | Current eye research 20090801 |
| Polycyclic aromatic hydrocarbons in Tripuí River, Ouro Preto, MG, Brazil. | Journal of hazardous materials 20090615 |
| Role of a moderately halophilic bacterial consortium in the biodegradation of polyaromatic hydrocarbons. | Marine pollution bulletin 20090201 |
| [Ah receptor-independent inhibition of gap junction intercellular communications in hepatoma cell culture 27 by polycyclic aromatic hydrocarbons]. | Tsitologiia 20090101 |
| Rapid SPE-HPLC determination of the 16 European priority polycyclic aromatic hydrocarbons in olive oils. | Journal of separation science 20081201 |
| Polycyclic aromatic hydrocarbons in spanish olive oils: relationship between benzo(a)pyrene and total polycyclic aromatic hydrocarbon content. | Journal of agricultural and food chemistry 20081112 |
| Effects of Benzo(e)Pyrene, a toxic component of cigarette smoke, on human retinal pigment epithelial cells in vitro. | Investigative ophthalmology & visual science 20081101 |
| The response of Ty1 test to genotoxins. | Archives of toxicology 20081001 |
| Size distribution of particle-phase molecular markers during a severe winter pollution episode. | Environmental science & technology 20080901 |
| Experimental approaches to evaluate activities of cytochromes P450 3A. | Interdisciplinary toxicology 20080901 |
| VOCs and PAHs emissions from creosote-treated wood in a field storage area. | The Science of the total environment 20080825 |
| Enhanced kinetics of solid-phase microextraction and biodegradation of polycyclic aromatic hydrocarbons in the presence of dissolved organic matter. | Environmental toxicology and chemistry 20080701 |
| Photochemical degradation of polycyclic aromatic hydrocarbons in oil films. | Environmental science & technology 20080401 |
| Fluorescence study of inclusion complexes between star-shaped cholic acid derivatives and polycyclic aromatic fluorescent probes and the size effects of host and guest molecules. | The journal of physical chemistry. B 20080320 |
| Unexpected DNA damage caused by polycyclic aromatic hydrocarbons under standard laboratory conditions. | Mutation research 20080227 |
| Optimization of the matrix solid-phase dispersion sample preparation procedure for analysis of polycyclic aromatic hydrocarbons in soils: comparison with microwave-assisted extraction. | Journal of chromatography. A 20070921 |
| The environmental carcinogen benzo[a]pyrene induces expression of monocyte-chemoattractant protein-1 in vascular tissue: a possible role in atherogenesis. | Mutation research 20070801 |
| Effects of benzo(e)pyrene and benzo(a)pyrene on P-glycoprotein-mediated transport in Caco-2 cell monolayer: a comparative approach. | Toxicology in vitro : an international journal published in association with BIBRA 20070801 |
| Oxidized metabolites from benzo[a]pyrene, benzo[e]pyrene, and aza-benzo[a]pyrenes. A computational study of their carbocations formed by epoxide ring opening reactions. | Organic & biomolecular chemistry 20070721 |
| Trophic dilution of polycyclic aromatic hydrocarbons (PAHs) in a marine food web from Bohai Bay, north China. | Environmental science & technology 20070501 |
| Benzo[a]pyrene-dependent activation of transcription factors NF-kappaB and AP-1 related to tumor promotion in hepatoma cell cultures. | Biochemistry. Biokhimiia 20070501 |
| [Determination of trace polycyclic aromatic hydrocarbons in surface sediments of Huangpu River by high performance liquid chromatography]. | Se pu = Chinese journal of chromatography 20070501 |
| Microheterogeneity evaluation of polycyclic aromatic hydrocarbons in particulate standard reference materials. | Analytical and bioanalytical chemistry 20070401 |
| Sample preparation of sewage sludge and soil samples for the determination of polycyclic aromatic hydrocarbons based on one-pot microwave-assisted saponification and extraction. | Analytical and bioanalytical chemistry 20070401 |
| UVA photoirradiation of methylated benzo[a]pyrene and benzo[e]pyrene leading to induction of lipid peroxidation. | International journal of environmental research and public health 20070201 |
| Source apportionment of molecular markers and organic aerosol--1. Polycyclic aromatic hydrocarbons and methodology for data visualization. | Environmental science & technology 20061215 |
| Polycyclic aromatic hydrocarbons in food samples collected in Barcelona, Spain. | Journal of food protection 20060801 |
| Electron affinities of polycyclic aromatic hydrocarbons by means of B3LYP/6-31+G* calculations. | The journal of physical chemistry. A 20060525 |
| Microsphere-based protease assays and screening application for lethal factor and factor Xa. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501 |
| Distribution of pesticides, PAHs and heavy metals in prawn ponds near Kolleru lake wetland, India. | Environment international 20060401 |
| Optimization of the procedure for the determination of polycyclic aromatic hydrocarbons and their derivatives in fish tissue: Estimation of measurements uncertainty. | Food additives and contaminants 20060301 |
| Phenacenes from Diels-Alder trapping of photogenerated o-xylylenols: phenanthrenes and benzo[e]pyrene bisimide. | Organic letters 20060216 |
| Physicochemical characterisation of combustion particles from vehicle exhaust and residential wood smoke. | Particle and fibre toxicology 20060101 |
| Time- and concentration-dependent changes in gene expression induced by benzo(a)pyrene in two human cell lines, MCF-7 and HepG2. | BMC genomics 20060101 |
| Further evaluation of the skin micronucleus test: results obtained using 10 polycyclic aromatic hydrocarbons. | Mutation research 20051207 |
| Detection of initiating as well as promoting activity of chemicals by a novel cell transformation assay using v-Ha-ras-transfected BALB/c 3T3 cells (Bhas 42 cells). | Mutation research 20051207 |
| Polycyclic aromatic hydrocarbons induce an inflammatory atherosclerotic plaque phenotype irrespective of their DNA binding properties. | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20050801 |
| Photochemical transformations of benzo[e]pyrene in solution and adsorbed on silica gel and alumina surfaces. | Environmental science & technology 20050515 |
| Detection of a novel mutagen, 3,6-dinitrobenzo[e]pyrene, as a major contaminant in surface soil in Osaka and Aichi Prefectures, Japan. | Chemical research in toxicology 20050201 |
| Solid-matrix fluorescence quenching of benzo[e]pyrene and (+/-)-anti-dibenzo[a, l]pyrene diolepoxide-DNA adducts. | Applied spectroscopy 20050101 |
| Performance of PAHs emission from bituminous coal combustion. | Journal of Zhejiang University. Science 20041201 |
| Gas chromatographic-mass spectrometric determination of polycyclic aromatic hydrocarbons formed during the pyrolysis of phenylalanine. | Journal of chromatography. A 20040206 |
| Spatial distributions and profiles of atmospheric polycyclic aromatic hydrocarbons in two industrial cities in Japan. | Environmental science & technology 20040101 |
| Degradation of polycyclic aromatic hydrocarbons and long chain alkanes at 60-70 degrees C by Thermus and Bacillus spp [corrected]. | Biodegradation 20031201 |
| Atmospheric particulate matter and polycyclic aromatic hydrocarbons for PM10 and size-segregated samples in Bangkok. | Journal of the Air & Waste Management Association (1995) 20031201 |
| Polycyclic aromatic hydrocarbons inhibit differentiation of human monocytes into macrophages. | Journal of immunology (Baltimore, Md. : 1950) 20030301 |
| Polycyclic aromatic hydrocarbons in mountain soils of the subtropical Atlantic. | Journal of environmental quality 20030101 |
| Picogram quantitation of polycyclic aromatic hydrocarbons adsorbed on aerosol particles by two-step laser mass spectrometry. | Analytical chemistry 20020715 |
| Arylhydrocarbon receptor-dependent induction of liver and lung cytochromes P450 1A1, 1A2, and 1B1 by polycyclic aromatic hydrocarbons and polychlorinated biphenyls in genetically engineered C57BL/6J mice. | Carcinogenesis 20020701 |
| Homogeneous liquid-liquid extraction and micellar electrokinetic chromatography using sweeping effect concentration system for determination of trace amounts of several polycyclic aromatic hydrocarbons. | Analytical and bioanalytical chemistry 20020501 |
| The Japanese medaka (Oryzias latipes) model: applicability for investigating the immunosuppressive effects of the aquatic pollutant benzo[a]pyrene (BaP). | Marine environmental research 20020101 |
| Induction of tumor clones in D. melanogaster wts/+ heterozygotes with chemical carcinogens. | Mutation research 20011115 |
| Polycyclic aromatic hydrocarbons in remote mountain lake waters. | Water research 20011101 |
| Spiral, herringbone, and triple-decker silver(I) complexes of benzopyrene derivatives assembled through eta(2)-coordination. | Inorganic chemistry 20010618 |
| Polycyclic aromatic hydrocarbons identified in soot extracts from domestic coal-burning stoves of Henan Province, China. | Environmental science & technology 20010515 |
| Inhibition of liver methionine adenosyltransferase gene expression by 3-methylcolanthrene: protective effect of S-adenosylmethionine. | Biochemical pharmacology 20010501 |
| Application of the ethoxyresorufin-O-deethylase (EROD) assay to mixtures of halogenated aromatic compounds. | Environmental toxicology 20010101 |
| Glycine N-methyltransferase is an example of functional diversity. Role as a polycyclic aromatic hydrocarbon-binding receptor. | The Journal of biological chemistry 19970822 |
| Metabolic requirements for induction of contact hypersensitivity to immunotoxic polyaromatic hydrocarbons. | Journal of immunology (Baltimore, Md. : 1950) 19951001 |
| Induction of CYP1A1 gene expression in mouse hepatoma cells by benzo[e]pyrene, a ligand of the 4S polycyclic hydrocarbon-binding protein. | Toxicology and applied pharmacology 19940901 |
| Benzo[e]pyrene elicits changes in the biochemical activities and chromatographic behavior of murine hepatic cytochromes P-450 that are distinct from those induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin. | Chemico-biological interactions 19920828 |
| Induction of CYP1A1 gene expression in H4-II-E rat hepatoma cells by benzo[e]pyrene. | Molecular carcinogenesis 19920101 |
| Arteriosclerotic plaque development is 'promoted' by polynuclear aromatic hydrocarbons. | Carcinogenesis 19881201 |
| Binding of polynuclear aromatic hydrocarbons to the rat 4S cytosolic binding protein: structure-activity relationships. | Cancer letters 19870201 |
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