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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__818328412843034__ initializing getValue debug = null getValue logLevel = null getValue allowjavascript = null AppletRegistry.checkIn(jmolApplet0_object__818328412843034__) 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:29021","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__818328412843034__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"818328412843034","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__818328412843034__ 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 11260814253D starting HoverWatcher_5 Time for openFile( Marvin 11260814253D 20 19 0 0 0 0 999 V2000 -2.6227 3.7602 1.9114 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6951 3.3042 0.7644 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8826 2.0319 1.1296 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0538 1.5610 -0.0115 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8663 0.2888 0.3538 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7940 -0.1673 -0.7932 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1732 4.6542 1.6135 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3387 2.9739 2.1526 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0365 3.9918 2.8012 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0086 4.1202 0.5236 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3044 3.1074 -0.1218 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5781 1.2241 1.3713 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2800 2.2387 2.0178 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7494 2.3688 -0.2532 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5488 1.3542 -0.8997 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1798 -0.5273 0.5945 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4756 0.4856 1.2399 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3444 -1.0613 -0.4952 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2078 -0.3989 -1.6830 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5101 0.6189 -1.0344 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 0 0 0 3 2 1 0 0 0 0 4 3 1 0 0 0 0 5 4 1 0 0 0 0 6 5 1 0 0 0 0 1 7 1 0 0 0 0 1 8 1 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 6 19 1 0 0 0 0 6 20 1 0 0 0 0 M END): 22 ms reading 20 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 20 atoms created ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation Script completed Jmol script terminated
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| Hexane () or n-hexane is an organic compound, a straight-chain alkane with six carbon atoms and the molecular formula C6H14.
Hexane is a colorless liquid, odorless when pure, and with a boiling point of approximately 69 °C (156 °F). It is widely used as a cheap, relatively safe, largely unreactive, and easily evaporated non-polar solvent, and modern gasoline blends contain about 3% hexane.
The term hexanes refers to a mixture, composed largely (>60%) of n-hexane, with varying amounts of the isomeric compounds 2-methylpentane and 3-methylpentane, and possibly, smaller amounts of nonisomeric C5, C6, and C7 (cyclo)alkanes. These "hexanes" mixtures are cheaper than pure hexane and are often used in large-scale operations not requiring a single isomer (e.g., as cleaning solvent or for chromatography). |
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Read full article at Wikipedia
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| InChI=1S/C6H14/c1-3-5-6-4-2/h3-6H2,1-2H3 |
| VLKZOEOYAKHREP-UHFFFAOYSA-N |
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non-polar solvent
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neurotoxin
A poison that interferes with the functions of the nervous system.
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non-polar solvent
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View more via ChEBI Ontology
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Outgoing
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hexane
(CHEBI:29021)
has role
neurotoxin
(CHEBI:50910)
hexane
(CHEBI:29021)
has role
non-polar solvent
(CHEBI:48355)
hexane
(CHEBI:29021)
is a
alkane
(CHEBI:18310)
hexane
(CHEBI:29021)
is a
volatile organic compound
(CHEBI:134179)
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Incoming
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1-iminohexane-2,3,4,5-tetrol
(CHEBI:111512)
has parent hydride
hexane
(CHEBI:29021)
1-isothiocyanato-6-(methylsulfanyl)hexane
(CHEBI:136921)
has parent hydride
hexane
(CHEBI:29021)
1-nitrohexane
(CHEBI:89185)
has parent hydride
hexane
(CHEBI:29021)
2,3,5-trimethylhexane
(CHEBI:141559)
has parent hydride
hexane
(CHEBI:29021)
2,4-dimethylhexane
(CHEBI:141561)
has parent hydride
hexane
(CHEBI:29021)
2,5-hexanedione
(CHEBI:85014)
has parent hydride
hexane
(CHEBI:29021)
2-hexanamine
(CHEBI:195543)
has parent hydride
hexane
(CHEBI:29021)
3-hexanone
(CHEBI:89891)
has parent hydride
hexane
(CHEBI:29021)
3-mercaptohexanol
(CHEBI:77690)
has parent hydride
hexane
(CHEBI:29021)
3-methoxy-3-methylhexane
(CHEBI:84286)
has parent hydride
hexane
(CHEBI:29021)
5-iminohexane-1,2,3,4,6-pentol
(CHEBI:131195)
has parent hydride
hexane
(CHEBI:29021)
7-(methylthio)heptanonitrile oxide
(CHEBI:136945)
has parent hydride
hexane
(CHEBI:29021)
hexanal
(CHEBI:88528)
has parent hydride
hexane
(CHEBI:29021)
hexane-1,6-diamine
(CHEBI:39618)
has parent hydride
hexane
(CHEBI:29021)
hexane-1,6-diol
(CHEBI:43078)
has parent hydride
hexane
(CHEBI:29021)
hexane-2,5-diol
(CHEBI:84894)
has parent hydride
hexane
(CHEBI:29021)
hexanol
(CHEBI:143552)
has parent hydride
hexane
(CHEBI:29021)
perfluorohexane
(CHEBI:39427)
has parent hydride
hexane
(CHEBI:29021)
hexyl group
(CHEBI:24593)
is substituent group from
hexane
(CHEBI:29021)
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CH3‒[CH2]4‒CH3
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IUPAC
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Hexan
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ChEBI
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Hexane
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KEGG COMPOUND
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HEXANE
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PDBeChem
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n-Hexane
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KEGG COMPOUND
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110-54-3
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CAS Registry Number
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KEGG COMPOUND
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110-54-3
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CAS Registry Number
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ChemIDplus
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110-54-3
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CAS Registry Number
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NIST Chemistry WebBook
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1730733
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Reaxys Registry Number
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Reaxys
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1985
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Gmelin Registry Number
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Gmelin
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Li H, Liu J, Sun Y, Wang W, Weng S, Xiao S, Huang H, Zhang W (2014)
N-hexane inhalation during pregnancy alters DNA promoter methylation in the ovarian granulosa cells of rat offspring.
Journal of applied toxicology : JAT 34, 841-856 [PubMed:23740543]
[show Abstract]
The N-hexane-induced impact on the reproductive system of the offspring of animals exposed to n-hexane has caused great concern. Pregnant Wistar rats inhaled 500, 2 500 or 12 500 ppm n-hexane during gestational days 1-20. Clinical characteristics and developmental indices were observed. Ovarian granulosa cells were extracted from F1 rats, the number of follicles was determined in ovarian slices and promoter methylation was assessed using MeDIP-Chip. Several methods were used to analyze the scanned genes, including the Gene Ontology Consortium tools, the DAVID Functional Annotation Clustering Tool, hierarchical clustering and KEGG pathway analysis. The results indicated that the live pups/litter ratio was significantly lowest in the 12 500 ppm group. A significant decrease in secondary follicles and an increase in atresic follicles were observed in the 12 500 ppm group. The number of shared demethylated genes was higher than that of the methylated genes, and the differentially methylated genes were enriched in cell death and apoptosis, cell growth and hormone regulation. The methylation profiles of the offspring from the 500 ppm and control groups were different from those of the 2500 and 12 500 ppm groups. Furthermore, the methylation status of genes in the PI3K-Akt and NF-kappa B signaling pathways was changed after n-hexane exposure. The Cyp11a1, Cyp17a1, Hsd3b1, Cyp1a1 and Srd5a1 promoters were hypermethylated in the n-hexane-exposed groups. These results indicate that the developmental toxicity of n-hexane in F1 ovaries is accompanied by the altered methylation of promoters of genes associated with apoptotic processes and steroid hormone biosynthesis. | Zayats MF, Leschev SM, Petrashkevich NV, Zayats MA, Kadenczki L, Szitás R, Szemán Dobrik H, Keresztény N (2013)
Distribution of pesticides in n-hexane/water and n-hexane/acetonitrile systems and estimation of possibilities of their extraction isolation and preconcentration from various matrices.
Analytica chimica acta 774, 33-43 [PubMed:23567114]
[show Abstract]
Distribution of 150 most widely used pesticides of different chemical classes (amides, anilinopirimidines, aromatics, benzenesulfonates, carbamates, dicarboximides, organophosphorus compounds, phenyl esters, phenylureas, pyrazoles, pyrethroids, pyrimidines, strobilurins, sulfamides, triazines, triazoles, etc.) in n-hexane/water and n-hexane/acetonitrile systems was investigated at 25°C. Distribution constants of pesticides (P) have been calculated as ratio of pesticide concentration in n-hexane to its concentration in water or acetonitrile phase. HPLC and GC methods were used for pesticides determination in phases. It was found that the overwhelming majority of pesticides are hydrophobic, i.e. in n-hexane/water system LgP≫0, and the difference in LgP values can reach 9.1 units. Replacement of water for acetonitrile leads to dramatic fall of LgP values reaching 9.5 units. The majority of LgP values in this case are negative and their differences is strongly leveled in comparison with a hexane/water system. Thus, maximal difference in pesticides LgP values for n-hexane/acetonitrile system is 3.2 units. It is shown that n-hexane can be used for selective and efficient extraction and preconcentration of pesticides from water matrices. On the other hand, acetonitrile is effective for the isolation and preconcentration of pesticides from hydrocarbon and vegetable oil matrices. The distribution constants described in the paper may be effectively used for the estimation of possibilities of extraction isolation, preconcentration and separation of pesticides. | Muhammad N, Saeed M, Khan H, Raziq N, Halimi SM, Abass M (2013)
Antipyretic and anticonvulsant activity of n-hexane fraction of Viola betonicifolia.
Asian Pacific journal of tropical biomedicine 3, 280-283 [PubMed:23620851]
[show Abstract]
ObjectiveTo investigate the antipyretic and anticonvulsant activities of n-hexane fraction of Viola betonicifolia (V. betonicifolia).MethodsThe antipyretic effect was scrutinized using brewer's yeast induced pyrexia and anticonvlsion effect was tested using pentylenetetrazol and strychnine induced convulsion in mice.ResultsN-hexane fraction of V. betonicifolia demonstrated highly significant antipyretic activity during various assessment times (1-5 h) when challenged in yeast induced pyrexia test. The effect was in a dose dependent manner with maximum attenuation (82.50%) observed at 300 mg/kg i.p. When tested in pentylenetetrazol induced convulsion test, the 1st stage (Ear and facial twitching) and 2nd stage (Convulsive wave through the body) was 100% protected during 24 h at all the test doses (300, 400 and 500 mg/kg i.p.), while the latency time of remaining stages was significantly increased. The maximum effect was observed by n-hexane fraction of V. betonicifolia at 400 and 500 mg/kg i.p., as the latency time for generalized clonic-tonic seizure (5th stage) was increased up to 25.34 min. However, n-hexane fraction of V. betonicifolia had no protection in strychnine induced convulsion test.ConclusionsIn conclusion, phytopharmacological studies provide scientific foundation to the folk uses of the plant in the treatment of pyrexia and neurological disorders. | Li L, Leopold K, Schuster M (2013)
Comparative study of alkylthiols and alkylamines for the phase transfer of gold nanoparticles from an aqueous phase to n-hexane.
Journal of colloid and interface science 397, 199-205 [PubMed:23452516]
[show Abstract]
An efficient ligand-assisted phase transfer method has been developed to transfer gold nanoparticles (Au-NPs, d: 5-25 nm) from an aqueous solution to n-hexane. Four different ligands, namely 1-dodecanethiol (DDT), 1-octadecanethiol (ODT), dodecylamine (DDA), and octadecylamine (ODA) were investigated, and DDT was found to be the most efficient ligand. It appears that the molar ratio of DDT to Au-NPs is a critical factor affecting the transfer efficiency, and 270-310 is found to be the optimum range, under which the transfer efficiency is >96%. Moreover, the DDT-assisted phase transfer can preserve the shape and size of the Au-NPs, which was confirmed by UV-vis spectra and transmission electron microscopy (TEM). Additionally, the transferred Au-NPs still can be well dispersed in the n-hexane phase and remain stable for at least 2 weeks. On the other hand, the ODT-, DDA-, and ODA-assisted phase transfer is fraught with problems either related to transfer efficiency or NPs aggregation. Overall, the DDT-assisted phase transfer of Au-NPs provides a rapid and efficient method to recover Au-NPs from an aqueous solution to n-hexane. | Lísal M, Izák P (2013)
Molecular dynamics simulations of n-hexane at 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl) imide interface.
The Journal of chemical physics 139, 014704 [PubMed:23822317]
[show Abstract]
Molecular dynamics simulations of n-hexane adsorbed onto the interface of 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl) imide ([bmim][Tf2N]) are performed at three n-hexane surface densities, ranged from 0.7 to 2.3 μmol/m(2) at 300 K. For [bmim][Tf2N] room-temperature ionic liquid, we use a non-polarizable all-atom force field with the partial atomic charges based on ab initio calculations for the isolated ion pair. The net charges of the ions are ±0.89e, which mimics the anion to cation charge transfer and polarization effects. The OPLS-AA force field is employed for modeling of n-hexane. The surface tension is computed using the mechanical route and its value decreases with increase of the n-hexane surface density. The [bmim][Tf2N]/n-hexane interface is analyzed using the intrinsic method, and the structural and dynamic properties of the interfacial, sub-interfacial, and central layers are computed. We determine the surface roughness, global and intrinsic density profiles, and orientation ordering of the molecules to describe the structure of the interface. We further compute the survival probability, normal and lateral self-diffusion coefficients, and re-orientation correlation functions to elucidate the effects of n-hexane on dynamics of the cations and anions in the layers. | Guerrero H, Cea P, Gascón I, Royo FM, Lafuente C (2013)
Volumetric study of the mixtures n-hexane + isomeric chlorobutane: experimental characterization and volume translated Peng-Robinson predictions.
The journal of physical chemistry. B 117, 10284-10292 [PubMed:23931182]
[show Abstract]
The pρTx behavior of the binary mixtures n-hexane + isomeric chlorobutane has been studied over the whole composition range at temperatures between 283.15 and 323.15 K and pressures from 0.1 to 65.0 MPa. Experimental densities have been used to obtain different excess properties: excess molar volume, excess isobaric expansibility, excess isothermal compressibility, and excess internal pressure. These excess properties have been analyzed in terms of molecular interactions and structural effects. Finally, experimental densities of the binary mixtures have been compared with the predictions of the volume translated Peng-Robinson (VTPR) model. The overall average deviation between experimental and calculated densities is 0.00427 g·cm(-3), which can be considered reasonably good predictions. | Mateus FH, Lepera JS, Marques MP, Boralli VB, Lanchote VL (2010)
Influence of N-hexane inhalation on the enantioselective pharmacokinetics and metabolism of verapamil in rats.
Chirality 22, 29-34 [PubMed:19229957]
[show Abstract]
Verapamil (VER) is commercialized as a racemic mixture of the (+)-(R)-VER and (-)-(S)-VER enantiomers. VER is biotransformed into norverapamil (NOR) and other metabolites through CYP-dependent pathways. N-hexane is a solvent that can alter the metabolism of CYP-dependent drugs. The present study investigated the influence of n-hexane (nose-only inhalation exposure chamber at concentrations of 88, 176, and 352 mg/m3) on the kinetic disposition of the (+)-(R)-VER, (-)-(S)-VER, (R)-NOR and (S)-NOR in rats treated with a single dose of racemic VER (10 mg/kg). VER and NOR enantiomers in rat plasma was analyzed by LC-MS/MS (m/z = 441.3 > 165.5 for the NOR and m/z 455.3 > 165.5 for the VER enantiomers) using a Chiralpak AD column. Pharmacokinetic analysis was performed using a monocompartmental model. The pharmacokinetics of VER was enantioselective in control rats, with higher plasma proportions of the (-)-(S)-VER eutomer (AUC(0-infinity) = 250.8 vs. 120.4 ng/ml/h; P < or = 0.05, Wilcoxon test). The (S)-NOR metabolite was also found to accumulate in plasma of control animals, with an S/R AUC(0-infinity) ratio of 1.5. The pharmacokinetic parameters AUC(0-infinity), Cl/F, Vd/F, and t(1/2) obtained for VER and NOR enantiomers were not altered by nose-only exposure to n-hexane at concentrations of 88, 176, or 352 mg/m3 (P > 0.05, Kruskal-Wallis test). However, the verapamil kinetic disposition was not enantioselective for the animals exposed to n-hexane at concentrations equal to or higher than the TLV-TWA. This finding is relevant considering that the (-)-(S)-VER eutomer is 10-20 times more potent than R-(+)-VER in terms of its chronotropic effect on atrioventricular conduction in rats and humans. | Sari-Minodier I, Truchon G, Charest-Tardif G, Bérubé A, Tardif R (2009)
The effect of workload on biological monitoring of occupational exposure to toluene and n-Hexane: contribution of physiologically based toxicokinetic modeling.
Journal of occupational and environmental hygiene 6, 415-432 [PubMed:19384711]
[show Abstract]
A physiologically based toxicokinetic model was used to examine the impact of work load on the relationship between the airborne concentrations and exposure indicator levels of two industrial solvents, toluene and n-Hexane. The authors simulated occupational exposure (8 hr/day, 5 days/week) at different concentrations, notably 20 ppm and 50 ppm, which are the current threshold limit values recommended by ACGIH for toluene and n-hexane, respectively. Different levels of physical activity, namely, rest, 25 W, and 50 W (for 12 hr followed by 12 hr at rest) were simulated to assess the impact of work load on the recommended biological exposure indices: toluene in blood prior to the last shift of the workweek, urinary o-cresol (a metabolite of toluene) at the end of the shift, and free (nonhydrolyzed) 2,5-hexanedione (a metabolite of n-hexane) at the end of the shift at the end of the workweek. In addition, urinary excretion of unchanged toluene was simulated. The predicted biological concentrations were compared with the results of both experimental studies among human volunteers and field studies among workers. The highest predicted increase with physical exercise was noted for toluene in blood (39 microg/L at 50 W vs. 14 microg/L at rest for 20 ppm, i.e., a 2.8-fold increase). The end-of-shift urinary concentrations of o-cresol and toluene were two times higher at 50 W than at rest (for 20 ppm, 0.65 vs. 0.33 mg/L for o-cresol and 43 vs. 21 microg/L for toluene). Urinary 2,5-hexanedione predicted for 50 ppm was 1.07 mg/L at 50 W and 0.92 mg/L at rest (+16%). The simulations that best describe the concentrations among workers exposed to toluene are those corresponding to 25 W or less. In conclusion, toxicokinetic modeling confirms the significant impact of work load on toluene exposure indicators, whereas only a very slight effect is noted on n-hexane kinetics. These results highlight the necessity of taking work load into account in risk assessment relative to toluene exposure. | McDermott C, O'Donoghue MH, Heffron JJ (2008)
n-Hexane toxicity in Jurkat T-cells is mediated by reactive oxygen species.
Archives of toxicology 82, 165-171 [PubMed:18231777]
[show Abstract]
Here we assess the role of reactive oxygen species (ROS) formation in the manifestation of n-hexane toxicity in Jurkat T-cells and the chemo-protective potential of the antioxidants epigallocatechin-3-gallate (EGCG) and thymoquinone (TQ) against n-hexane toxicity in vitro. n-Hexane is an important industrial solvent and ambient air pollutant. Subchronic exposure to n-hexane results in a concentration-dependent increase in ROS formation with a corresponding decrease in Jurkat T-cell proliferation. Results from time-course studies indicate that ROS formation plays a causal role in n-hexane induced alterations in Jurkat T-cell proliferation and membrane integrity. Treatment of cells with EGCG, at a concentration reached in plasma, reduced the ROS formation caused by exposure to n-hexane and inhibited the decrease in cell proliferation. Similar effects were obtained with TQ. Both EGCG and TQ significantly reduced n-hexane-induced LDH leakage to control levels. The combined results show that oxidative stress plays a role in the development of n-hexane toxicity. | Bebarta V, DeWitt C (2004)
Miscellaneous hydrocarbon solvents.
Clinics in occupational and environmental medicine 4, 455-79, vi [PubMed:15325316]
[show Abstract]
The solvents discussed in this article are common solvents not categorized as halogenated, aromatic, or botanical. The solvents discussed are categorized into two groups: hydrocarbon mixtures and single agents. The hydrocarbon mixtures discussed are Stoddard solvent, naphtha, and kerosene. The remaining solvents described are n-hexane, methyl n-butyl ketone, dimethylformamide, dimethyl sulfoxide, and butyl mercaptans. Effects common to this group of agents and their unique effects are characterized. Treatment of exposures and toxic effects of these solvents is described, and physiochemical properties and occupational exposure levels are listed. | Muralidhar RV, Chirumamilla RR, Ramachandran VN, Marchant R, Nigam P (2002)
Resolution of (RS)-proglumide using lipase from Candida cylindraceae.
Bioorganic & medicinal chemistry 10, 1471-1475 [PubMed:11886809]
[show Abstract]
Proglumide is used in the treatment of neuropathic pain. It acts by inhibiting peptide cholecystokinin (CCK). Neural injury produces an elevation in plasma CCK. Proglumide has been also shown to augment the analgesic effect of sustained release morphine in neuropathic pain. Currently proglumide is administered as a racemic mixture. In the present study, an attempt is made to separate the racemic mixture of the drug using lipase obtained from Candida cylindracea by stereoselective esterification. Enzymatic stereoselective esterification was carried out in organic solvents. The resolution was studied using a chromatographic column with a chiral support and mass spectrometry. The reaction conditions for stereoselective esterification including amount of substrate, amount of enzyme, alcohol, solvent and temperature were optimised during the present investigation. Butanol and hexanol were found to be suitable for formation of S and R esters, respectively. Hexane was the best solvent for esterification and the optimum temperature was found to be 30 degreesC. | Julián E, Cama M, Martínez P, Luquin M (2001)
An ELISA for five glycolipids from the cell wall of Mycobacterium tuberculosis: Tween 20 interference in the assay.
Journal of immunological methods 251, 21-30 [PubMed:11292478]
[show Abstract]
Mycobacterium tuberculosis cell wall contains antigenic glycolipids: phenol-glycolipid (PGL), diacyltrehalose (DAT), triacyltrehalose (TAT), cord-factor (CF), and sulpholipid-I (SL-I). In the last decade, the usefulness of these antigens for the serodiagnosis of tuberculosis has been evaluated mainly using enzyme-linked immunosorbent assays (ELISA). Currently, there are no conclusive results about the utility of these glycolipidic antigens, because the results obtained by different groups are discrepant. In order to explain these discrepancies, we have investigated the methodological variations in the ELISAs used previously. Specifically, we have studied the following: the coating solvent, the optimum amount of glycolipid coated per well, the blocking agent, and the use of detergent (Tween 20) in the washing buffer. The most significant finding was that Tween 20 detaches PGL, DAT, TAT and SL-I from microtitre wells. However, Tween 20 does not remove CF from the wells. In addition, we have found that the best solvent for coating is n-hexane, that the optimum antigen coating concentration is 1000 ng/well, and that BSA and gelatin are equally effective blocking agents. We can therefore conclude that the use of Tween 20 as a detergent, and the lower antigen coating concentrations (100-200 ng/well), may well explain some of the discrepancies in previous studies. | Nagasaki T, Yasuda S, Imai T (2001)
Preparation of antibody against agatharesinol, a norlignan, using a hapten-carrier conjugate.
Phytochemistry 58, 833-840 [PubMed:11684179]
[show Abstract]
In order to immunolabel heartwood extractives in Japanese cedar (Sugi, Cryptomeria japonica), we attempted to prepare antibodies against agatharesinol, a major norlignan of these heartwood extractives. Agatharesinol by itself is not antigenic due to its low-M(r), and thus was covalently bound to bovine serum albumin in order to synthesize an antigenic hapten-carrier conjugate (artificial antigen). The number of agatharesinol molecules per artificial antigen molecule was estimated as 27-28 by quantifying Lys in an acid hydrolysate of the artificial antigen by HPLC. Reaction between the artificial antigen and serum obtained from a rabbit immunized with the artificial antigen was competitively inhibited by agatharesinol, indicating the successful production of anti-agatharesinol antibodies. Inhibition by sequirin C, another major norlignan in Sugi, was weaker than that by agatharesinol. Furthermore, an EtOAc soluble fraction, which contains mainly norlignans, inhibited the reaction more strongly than any of the other fractions of Sugi heartwood extractives. Thus, the antiserum we have produced reacts most strongly with agatharesinol and recognizes norlignans almost selectively among Sugi heartwood extractives. | Graham DG, Amarnath V, Valentine WM, Pyle SJ, Anthony DC (1995)
Pathogenetic studies of hexane and carbon disulfide neurotoxicity.
Critical reviews in toxicology 25, 91-112 [PubMed:7612176]
[show Abstract]
Two commonly employed solvents, n-hexane and carbon disulfide (CS2), although chemically dissimilar, result in identical neurofilament-filled swellings of the distal axon in both the central and peripheral nervous systems. Whereas CS2 is itself a neurotoxicant, hexane requires metabolism to the gamma-diketone, 2,5-hexanedione (HD). Both HD and CS2 react with protein amino functions to yield initial adducts (pyrrolyl or dithiocarbamate derivatives, respectively), which then undergo oxidation or decomposition to an electrophile (oxidized pyrrole ring or isothiocyanate), that then reacts with protein nucleophiles to result in protein cross-linking. It is postulated that progressive cross-linking of the stable neurofilament during its anterograde transport in the longest axons ultimately results in the accumulation of neurofilaments within axonal swellings. Reaction with additional targets appears to be responsible for the degeneration of the axon distal to the swellings. |
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