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| o-xylene |
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| CHEBI:28063 |
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| o-xylene |
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| A xylene substituted by methyl groups at positions 1 and 2. |
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This entity has been manually annotated by the ChEBI Team.
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CHEBI:44697, CHEBI:10611, CHEBI:25623
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| No supplier information found for this compound. |
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Molfile
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SDF
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more structures >>
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call loadScript javascripts\jsmol\core\package.js call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js Jmol JavaScript applet jmolApplet0_object__998297068881924__ initializing getValue debug = null getValue logLevel = null getValue allowjavascript = null AppletRegistry.checkIn(jmolApplet0_object__998297068881924__) call loadScript javascripts\jsmol\core\corestate.z.js viewerOptions: { "name":"jmolApplet0_object","applet":true,"documentBase":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28063","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__998297068881924__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"998297068881924","bgcolor":"#000" } (C) 2012 Jmol Development Jmol Version: 13.2.7 $Date: 2013-10-01 11:35:15 -0500 (Tue, 01 Oct 2013) $ java.vendor: j2s java.version: 0.0 os.name: j2s Access: ALL memory: 0.0/0.0 processors available: 1 useCommandThread: false appletId:jmolApplet0_object (signed) starting HoverWatcher_1 getValue emulate = null defaults = "Jmol" getValue boxbgcolor = null getValue bgcolor = #000 backgroundColor = "#000" getValue ANIMFRAMECallback = null getValue APPLETREADYCallback = Jmol._readyCallback APPLETREADYCallback = "Jmol._readyCallback" getValue ATOMMOVEDCallback = null getValue CLICKCallback = null getValue ECHOCallback = null getValue ERRORCallback = null getValue EVALCallback = null getValue HOVERCallback = null getValue LOADSTRUCTCallback = null getValue MEASURECallback = null getValue MESSAGECallback = null getValue MINIMIZATIONCallback = null getValue PICKCallback = null getValue RESIZECallback = null getValue SCRIPTCallback = null getValue SYNCCallback = null getValue STRUCTUREMODIFIEDCallback = null getValue doTranslate = null language=en_US getValue popupMenu = null getValue script = null Jmol applet jmolApplet0_object__998297068881924__ ready call loadScript javascripts\jsmol\core\corescript.z.js call loadScript javascripts\jsmol\J\script\FileLoadThread.js starting QueueThread0_2 script 1 started starting HoverWatcher_3 starting HoverWatcher_4 The Resolver thinks Mol Marvin 06250710323D starting HoverWatcher_5 Time for openFile( Marvin 06250710323D 18 18 0 0 0 0 999 V2000 -1.6598 -0.2062 -0.4651 C 0 0 0 0 0 0 0 0 0 6 0 0 -1.6598 -1.5848 -0.1941 C 0 0 0 0 0 0 0 0 0 5 0 0 -0.4966 -2.2012 0.2943 C 0 0 0 0 0 0 0 0 0 4 0 0 0.6623 -1.4366 0.5100 C 0 0 0 0 0 0 0 0 0 3 0 0 -0.5011 0.5782 -0.2534 C 0 0 0 0 0 0 0 0 0 1 0 0 -0.5413 2.0319 -0.5518 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6791 -0.0472 0.2423 C 0 0 0 0 0 0 0 0 0 2 0 0 1.9234 0.7259 0.4832 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5226 0.2149 -0.8204 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5049 -2.1385 -0.3522 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4933 -3.2044 0.4926 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4948 -1.9139 0.8667 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5046 2.3818 -0.9248 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3204 2.5990 0.3543 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2054 2.2717 -1.3109 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7517 0.1264 0.8627 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2571 1.1845 -0.4493 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7312 1.5118 1.2159 H 0 0 0 0 0 0 0 0 0 0 0 0 5 1 4 0 0 0 0 5 7 4 0 0 0 0 1 2 4 0 0 0 0 2 3 4 0 0 0 0 3 4 4 0 0 0 0 4 7 4 0 0 0 0 5 6 1 0 0 0 0 7 8 1 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 6 13 1 0 0 0 0 6 14 1 0 0 0 0 6 15 1 0 0 0 0 8 16 1 0 0 0 0 8 17 1 0 0 0 0 8 18 1 0 0 0 0 M END): 19 ms reading 18 atoms ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false 1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them. Default Van der Waals type for model set to Babel 18 atoms created ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation Script completed Jmol script terminated
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| o-Xylene (ortho-xylene) is an aromatic hydrocarbon with the formula C6H4(CH3)2, with two methyl substituents bonded to adjacent carbon atoms of a benzene ring (the ortho configuration). It is a constitutional isomer of m-xylene and p-xylene, the mixture being called xylene or xylenes. o-Xylene is a colourless slightly oily flammable liquid. |
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Read full article at Wikipedia
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| InChI=1S/C8H10/c1-7-5-3-4-6-8(7)2/h3-6H,1-2H3 |
| CTQNGGLPUBDAKN-UHFFFAOYSA-N |
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1,2-dimethylbenzene
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NIST Chemistry WebBook
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1,2-Dimethylbenzol
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ChEBI
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2-xylene
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ChemIDplus
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3,4-xylene
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NIST Chemistry WebBook
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o-Dimethylbenzene
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KEGG COMPOUND
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o-Methyltoluene
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KEGG COMPOUND
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o-Xylene
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KEGG COMPOUND
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o-Xylol
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ChemIDplus
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ORTHO-XYLENE
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PDBeChem
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ortho-xylene
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MetaCyc
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6967
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ChemSpider
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C00056020
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KNApSAcK
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c0248
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UM-BBD
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C07212
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KEGG COMPOUND
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CPD-1421
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MetaCyc
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DB03029
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DrugBank
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FDB005819
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FooDB
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HMDB0059851
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HMDB
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O-Xylene
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Wikipedia
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OXE
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PDBeChem
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| View more database links |
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1815558
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Reaxys Registry Number
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Reaxys
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67796
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Gmelin Registry Number
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Gmelin
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95-47-6
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CAS Registry Number
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NIST Chemistry WebBook
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95-47-6
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CAS Registry Number
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ChemIDplus
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Würth A, Menberg K, Martus P, Sültenfuß J, Blum P (2021)
Quantifying biodegradation rate constants of o-xylene by combining compound-specific isotope analysis and groundwater dating.
Journal of contaminant hydrology 238, 103757 [PubMed:33465657]
[show Abstract]
The objective of this study is to estimate hydraulic conductivities and biodegradation rate constants in a coal-tar contaminated aquifer by compound-specific isotope analysis (CSIA) and tracer-based (3H-3He) groundwater dating (TGD). In two observation wells downgradient from the contaminant source in situ biodegradation of o-xylene, toluene and naphthalene under sulfate-reducing redox conditions could be demonstrated using CSIA. Median biodegradation rate constants for o-xylene ranging between 0.08 and 0.22 a-1 were estimated. By using tracer-based groundwater dating in these two wells, hydraulic conductivities could be also estimated, which are in a similar range as k-values derived from sieve analysis, a pumping test and a calibrated groundwater flow model. These results clearly demonstrate the applicability of tracer-based groundwater dating for the determination of in situ hydraulic conductivities in aquifers without pumping contaminated groundwater. Finally, a sensitivity analysis is performed using a Monte Carlo simulation. These results indicate high sensitivities of the assumed effective porosity for the estimation of the hydraulic conductivity and the selected isotope enrichment factor for the biodegradation rate constant, respectively. Conversely, the outcome also evidently demonstrates the main limitations of the novel combined isotope approach for a successful implementation of monitored natural attenuation (MNA) at such field sites. | Mahmood A, Wang X, Shi G, Wang Z, Xie X, Sun J (2020)
Revealing adsorption and the photodegradation mechanism of gas phase o-xylene on carbon quantum dots modified TiO2 nanoparticles.
Journal of hazardous materials 386, 121962 [PubMed:31911380]
[show Abstract]
Here, we report the photocatalytic oxidation (PCO) of o-xylene on carbon quantum dots (CQDs) modified TiO2 nanoparticles. The results demonstrated that with 1 wt% CQDs loading, 87 % of o-xylene (50 ppm) can be photodegraded, which is 55.3 % higher than pure TiO2 (56 %) under UV/visible light. This improved photocatalytic activity is associated with the important role of CQDs on TiO2 surface, which increased the o-xylene adsorption and facilitated the photogenerated hole-electron separation process. Also, the 1 wt%CQDs/TiO2 nanocomposite showed photocatalytic activity in the visible region (λ > 400 nm) compared to pure TiO2 (inactive). The DFT study revealed that o-xylene strongly adsorb on TiO2 (001) surface than (101) through π electrons of the aromatic ring. The in situ DRIFTS study showed that free OH groups on the photocatalyst surface could act as effective Lewis sides for the o-xylene adsorption. The interaction of π electrons of the aromatic ring and isolated OH groups was also observed. The FTIR peaks for CO2 increased in the case of CQDs/TiO2 nanocomposite contrasted to pure TiO2, which suggested that the presence of CQDs improved the mineralization potency of TiO2. These findings should affect the quest for a better photocatalyst to photodegrade VOCs. | Hu Y, Li N, Li G, Wang A, Cong Y, Wang X, Zhang T (2017)
Sustainable Production of o-Xylene from Biomass-Derived Pinacol and Acrolein.
ChemSusChem 10, 2880-2885 [PubMed:28621498]
[show Abstract]
o-Xylene (OX) is a large-volume commodity chemical that is conventionally produced from fossil fuels. In this study, an efficient and sustainable two-step route is used to produce OX from biomass-derived pinacol and acrolein. In the first step, the phosphotungstic acid (HPW)-catalyzed pinacol dehydration in 1-ethyl-3-methylimidazolium chloride ([emim]Cl) selectively affords 2,3-dimethylbutadiene. The high selectivity of this reaction can be ascribed to the H-bonding interaction between Cl- and the hydroxy group of pinacol. The stabilization of the carbocation intermediate by the surrounding anion Cl- may be another reason for the high selectivity. Notably, the good reusability of the HPW/[emim]Cl system can reduce the waste output and production cost. In the second step, OX is selectively produced by a Diels-Alder reaction of 2,3-dimethylbutadiene and acrolein, followed by a Pd/C-catalyzed decarbonylation/aromatization cascade in a one-pot fashion. The sustainable two-step process efficiently produces renewable OX in 79 % overall yield. Analogously, biomass-derived crotonaldehyde and pinacol can also serve as the feedstocks for the production of 1,2,4-trimethylbenzene. | de Lacy Costello B, Amann A, Al-Kateb H, Flynn C, Filipiak W, Khalid T, Osborne D, Ratcliffe NM (2014)
A review of the volatiles from the healthy human body.
Journal of breath research 8, 014001 [PubMed:24421258]
[show Abstract]
A compendium of all the volatile organic compounds (VOCs) emanating from the human body (the volatolome) is for the first time reported. 1840 VOCs have been assigned from breath (872), saliva (359), blood (154), milk (256), skin secretions (532) urine (279), and faeces (381) in apparently healthy individuals. Compounds were assigned CAS registry numbers and named according to a common convention where possible. The compounds have been grouped into tables according to their chemical class or functionality to permit easy comparison. Some clear differences are observed, for instance, a lack of esters in urine with a high number in faeces. Careful use of the database is needed. The numbers may not be a true reflection of the actual VOCs present from each bodily excretion. The lack of a compound could be due to the techniques used or reflect the intensity of effort e.g. there are few publications on VOCs from blood compared to a large number on VOCs in breath. The large number of volatiles reported from skin is partly due to the methodologies used, e.g. collecting excretions on glass beads and then heating to desorb VOCs. All compounds have been included as reported (unless there was a clear discrepancy between name and chemical structure), but there may be some mistaken assignations arising from the original publications, particularly for isomers. It is the authors' intention that this database will not only be a useful database of VOCs listed in the literature, but will stimulate further study of VOCs from healthy individuals. Establishing a list of volatiles emanating from healthy individuals and increased understanding of VOC metabolic pathways is an important step for differentiating between diseases using VOCs. | Kountouriotis A, Aleiferis PG, Charalambides AG (2014)
Numerical investigation of VOC levels in the area of petrol stations.
The Science of the total environment 470-471, 1205-1224 [PubMed:24246944]
[show Abstract]
In the area of petrol stations several Volatile Organic Compounds (VOCs) leak into the atmosphere due to the evaporation of liquid fuels, especially of gasoline that is predominantly composed of light hydrocarbons. The aim of the present study is to investigate the spatial distribution of various VOCs when leaked into the atmosphere in the area of a petrol station. The study is based on numerical simulations. The effect of wind speed and direction, as well as of air temperature has been studied. Gasoline components of different properties have been studied (e.g. pentane, iso-octane, o-xylene, toluene, benzene), as well as ethanol that is considered a new fuel blend component that can be found in different fractions in new gasoline blends worldwide. The area of flammable cloud near the source of the leak is investigated for various atmospheric conditions taking into account the lower and higher flammable limits of each compound. Lastly, the exposure to gasoline vapour is studied taking into consideration the recommended occupational exposure limits of various organisations. | Zhang L, Zhang C, Cheng Z, Yao Y, Chen J (2013)
Biodegradation of benzene, toluene, ethylbenzene, and o-xylene by the bacterium Mycobacterium cosmeticum byf-4.
Chemosphere 90, 1340-1347 [PubMed:22960059]
[show Abstract]
A new strain Mycobacterium cosmeticum byf-4 able to simultaneously degrade benzene, toluene, ethylbenzene, and o-xylene (BTE(o-)X) compounds has been isolated and identified previously in our laboratory. We further report here the extent of degradation of every BTE(o-)X component, and unravel the initial mechanism involved in BTE(o-)X degradation. This organism efficiently degrades all the BTE(o-)X components when these compounds are added either individually or as a composite mixture, and has a preference for toluene followed by benzene, ethylbenzene and then o-xylene. The significantly high carbon recovery indicated that the predominant fate for BTE(o-)X compounds was mineralization and incorporation into cell materials. The presence of BTE compounds in binary or ternary mixtures consistently had a negative effect on o-xylene degradation. The initial steps involved in the degradation of BTE(o-)X were investigated by isolation of metabolites and assay of reverse transcription RT-PCR. Isolation of metabolites suggested that the BTE(o-)X compounds were initially converted by a dioxygenase to their respective catechols. The gene sequence of the PCR amplicons revealed that this isolate contained a 454-bp toluene dioxygenase (TOD) fragment. The BTE(o-)X-specific induction of the genes encoding TOD was confirmed by RT-PCR analysis. These results indicated that TOD was possibly responsible for the initial steps of BTE(o-)X catabolism in M. cosmeticum byf-4. | De Preter V, Van Staeyen G, Esser D, Rutgeerts P, Verbeke K (2009)
Development of a screening method to determine the pattern of fermentation metabolites in faecal samples using on-line purge-and-trap gas chromatographic-mass spectrometric analysis.
Journal of chromatography. A 1216, 1476-1483 [PubMed:19167006]
[show Abstract]
An on-line screening method to analyse volatile organic compounds (VOCs) in faecal samples was developed. VOCs were isolated from a standard solution or faecal samples using a purge-and-trap system and identified and quantified by GC-MS. The experimental conditions were optimised and the performance of the system was evaluated. Linear calibration curves were obtained with correlation coefficients of at least 0.992. RSDs within and between days were less than 10%. The method was successfully applied to the analysis of faecal samples, yielding 135 different volatile organic compounds identified in 11 faecal samples. Of those, 22 VOCs were found in all volunteers, whereas 34 VOCs were person-specific. | Han QJ, Wu HL, Cai CB, Tang LJ, Yu RQ (2008)
Using near-infrared spectroscopy and differential adsorption bed method to study adsorption kinetics of orthoxylene on silica gel.
Talanta 76, 752-757 [PubMed:18656653]
[show Abstract]
This paper has demonstrated the study on the adsorption kinetics of orthoxylene on silica gel with a novel experimental methodology. In the method, there was a differential adsorption bed (DAB) where the solid adsorbent always contacted with the same bulk concentration of the adsorbate vapor, and the DAB was monitored with near-infrared diffuse reflectance spectroscopy (NIRDRS) continuously as well as non-invasively. Local partial least squares (PLS) algorithm was suggested to replace normal global PLS method in multivariate calibration models for processing NIRDRS data, because the concentration of the adsorbate on the adsorbent varied greatly as the adsorption process was going on. In this way, we, conveniently as well as promptly, obtained instantaneous adsorption rates of several orthoxylene/silica gel adsorption processes under different conditions like partial pressure of orthoxylene vapor and velocity of gas, and discovered that the adsorption process was physical adsorption, and mainly controlled by external diffusion. | Silaev MM (2001)
[New kinetic model of the radical-chain oxidation, including competitive reactions: oxygen as an autoinhibitor].
Biofizika 46, 203-209 [PubMed:11357330]
[show Abstract]
The application of competitive kinetics to the process of nonkatalytic oxidation by the radical-chain nonbranched mechanism was considered using the homogenous liquid phase oxidation of orthoxylene as an example. It was assumed that the free cycloalkylhydrotetraoxyl radical [formula: see text] is the intermediate compound that inhibits the chain process. By the method of quasi-stationary concentrations, kinetic equations for the rates of formation of oxidation products (alkylhydroperoxide, alcohols, carbonyl compounds, etc.) were derived in which 1-3 parameters should be determined. | Park SH, Schatz RA (1999)
Effect of low-level short-term o-xylene inhalation of benzo[a]pyrene (BaP) metabolism and BaP-DNA adduct formation in rat liver and lung microsomes.
Journal of toxicology and environmental health. Part A 58, 299-312 [PubMed:10598955]
[show Abstract]
o-Xylene is a commonly used solvent that alters mixed-function oxidase (MFO) activity in an organ- and isozyme-specific pattern following intraperitoneal (ip) administration. Similar MFO alterations have been observed after ip or inhalation exposure to other methyl benzenes. These MFO alterations shifted the metabolism of the carcinogen benzo[a]pyrene (BaP) toward formation of toxication metabolites in lung. The purpose of this study was to determine whether o-xylene inhalation caused similar MFO changes and whether these alterations were reflected in altered BaP metabolism and BaP-DNA adduct formation. o-Xylene (300 ppm, 6 h) decreased the activity of arylhydrocarbon hydroxylase (AHH) in lung. CYP2B1 activity (benzyloxyresorufin O-dealkylase; BROD), which is responsible for metabolism of BaP to relatively nontoxic metabolites, was decreased in lung, as was, to a lesser extent, CYP1A1 (ethoxyresorufin O-dealkylase; EROD), which is responsible for metabolism of BaP to reactive/toxic metabolites. The BROD/EROD ratio, an indirect indicator of the pattern of BaP toxication/detoxication, was decreased in lung, suggesting that BaP metabolism is shifted toward toxication. No MFO alterations were observed in liver. In lung microsomes, o-xylene increased formation of 7,8-BaP-diol, while 9,10-BaP-diol, 3-OH BaP, and 9-OH BaP were decreased. In liver, o-xylene increased 9-OH BaP formation, while 4,5- and 9,10-diols as well as total diols were decreased. The toxication/detoxication ratios for BaP individual and total metabolite groups were increased in lung microsomes and unaltered in liver. The major BaP-DNA adduct, BaP diol epoxide-N2-deoxyguanosine, was increased in lung but decreased in liver microsomes from o-xylene-exposed rats. Four minor BaP-DNA adducts were formed in lung and three in liver, only one of which (liver adduct 3) was decreased. The o-xylene-induced increase in BaP adduct formation in lung and decrease in liver indicate that coexposure to organic solvents such as the methyl benzenes may alter the carcinogenesis of BaP, or other PAHs, in an organ-specific fashion. | van Beelen P, Fleuren-Kemilä AK (1993)
Toxic effects of pentachlorophenol and other pollutants on the mineralization of acetate in several soils.
Ecotoxicology and environmental safety 26, 10-17 [PubMed:7691530]
[show Abstract]
The mineralization of [14C]acetate was studied in bottles with fresh soil and groundwater. Addition of toxicants inhibited the formation of 14CO2 and dose-effect curves were obtained. The acetate mineralization was not inhibited by zinc, cadmium, K2Cr2O7, chloropyrifos, and paraquat in an acid sandy soil at 1000 mg/kg dry soil. The IC10 is the toxicant concentration which inhibits 10% of the initial mineralization rate. The IC10 concentrations for 3,4-dichloroaniline, triphenyltin, and orthoxylene were 48, 96, and 730 mg/kg, respectively, in the acid sandy soil. The IC10 of pentachlorophenol was measured in samples from the acid sandy soil and in several other soil and subsoil samples. The geometrical mean of the 13 IC10 values was 16 mg pentachlorophenol/kg. A statistical method was used to calculate the PCP concentration above which 5% of the most sensitive acetate-mineralizing communities in all soils are influenced. The best estimate of this concentration is 0.3 mg PCP/kg but to be on the safe side the 95% confidence level of this concentration is 25 micrograms/kg. | Ogata M, Yamazaki Y, Sugihara R, Shimada Y, Meguro T (1980)
Quantitation of urinary o-xylene metabolites of rats and human beings by high performance liquid chromatography.
International archives of occupational and environmental health 46, 127-139 [PubMed:7399721] |
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