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Chemical Compound Review

Chromar     1,4-dimethylbenzene

Synonyms: Scintillar, P-XYLENE, p-Xylenes, p-Xylol, Para-Xylene, ...
 
 
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Disease relevance of p-xylene

 

Psychiatry related information on p-xylene

  • Studies of motor activity showed that while vertically-directed activity was unaffected by p-xylene, horizontally-directed activity was increased by about 30% for the first 15 min of each daily 25-min test.(ABSTRACT TRUNCATED AT 250 WORDS)[6]
  • In contrast, inhaled p-xylene at 1600 ppm suppressed response rates in an automaintained reversal learning paradigm without affecting reversal rate [6].
  • Among the three isomers studied, only para-xylene produced moderate to severe ototoxicity in rats exposed at 900 and 1,800 p.p.m. Increased auditory thresholds were observed at 2, 4, 8 and 16 kHz in rats exposed to 1800 p.p.m. para-xylene [7].
 

High impact information on p-xylene

  • Insight into the mechanism of aromatic hydroxylation by toluene 4-monooxygenase by use of specifically deuterated toluene and p-xylene [8].
  • Vesicle fusion (contents mixing) and leakage were then monitored with the 1-aminonaphthalene-3,6,8-trisulfonic acid/p-xylene bis(pyridinium bromide) fluorescence assay [9].
  • Enhanced para-xylene selectivity in the toluene alkylation reaction at ultralow contact time [10].
  • Solid state NMR method for the determination of 3D zeolite framework/sorbate structures: 1H/29Si CP MAS NMR study of the high-loaded form of p-xylene in ZSM-5 and determination of the unknown structure of the low-loaded form [11].
  • The activation energy barrier of p-xylene formation is found to be approximately 20 kJ/mol lower than the corresponding values for the formation of its isomers [12].
 

Chemical compound and disease context of p-xylene

 

Biological context of p-xylene

  • Kinetic measurements of the acylation of toluene (2a) and p-xylene (2b), side-chain deuterated toluene (2a-d(3)), as well as perdeuterated toluene (2a-d(8)) and p-xylene (2b-d(10)) with the aroyl triflate 1 in 1,2-dichloroethane reveal a strong dependence of the isotope effect on reaction conditions [18].
  • The catabolic potential of the isolate was expanded to include m- and p-xylene and related hydrocarbons by transfer of the TOL plasmid pWW0-Km [19].
  • During growth with p-xylene (20% [vol/vol]), there was an initial lag period accompanied by cell death, which was followed by a period of exponential growth [1].
  • A similar depression in peak N3 amplitude was observed following inhalation exposure to 1600 ppm p-xylene [20].
  • The intent of this study was to determine the effect of intermittent, acute, and subchronic p-xylene exposure on the axonal transport of proteins and glycoproteins within the rat retinofugal tract [21].
 

Anatomical context of p-xylene

 

Associations of p-xylene with other chemical compounds

  • Two distinct p-xylene and water environments were identified within the C18-bonded silica through the measurement of (1)H NMR chemical shifts, T(1) and T(2) relaxation times and diffusion coefficients, including their temperature dependence [24].
  • Disk-shaped triazine triamides self-assembled to form columnar-type helical aggregates through pi-stacking interactions among the central triphenyltriazine moieties, hydrogen-bonding interactions among the amide groups, and van der Waals interactions among the alkyl groups in nonpolar solvents such as hexane, octane, toluene, and p-xylene [25].
  • However, polarographic studies indicated that the organism utilizes the same pathway for the degradation of toluene, m-xylene, and p-xylene as that used by P. putida mt-2 which contains the TOL plasmid pWWO.(ABSTRACT TRUNCATED AT 250 WORDS)[1]
  • Kinetics of biodegradation of p-xylene and naphthalene and oxygen transfer in a novel airlift immobilized bioreactor [26].
  • In acetonitrile, the formation of the p-xylene radical cation requires two 266 nm photons, and the decay rate of the radical cation ((1.6 +/- 0.2) x 10(6) s(-1)) equals the growth rate of the p-methylbenzyl radical ((2.0 +/- 0.2) x 10(6) s(-1)) [27].
 

Gene context of p-xylene

  • Probing molecular dynamics in chromatographic systems using high-resolution 1H magic-angle-spinning NMR spectroscopy: interaction between p-Xylene and C18-bonded silica [24].
  • The catechols were converted to meta ring fission products by an inducible catechol-2,3-dioxygenase which was partially purified from p-xylene-grown cells of P. putida BG1 [15].
  • The contact angle, surface free energy, p-xylene adhesion, and zeta potential of these bacteria were in the range of 43-69 deg, 45.4-61.8 erg cm(-2), 2.3-80.3%, and from -650.2 to + 17.5 mV, respectively [28].
  • The micellization of PEO-PPO-PEO block copolymers in p-xylene has been studied in the presence of CO2 [29].
  • MATERIALS AND METHODS: The cytotoxicity of proximal tubular cells (LLC-PK1) exposed to 106 mg/mL of p-xylene or 92 mg/mL of toluene was compared with untreated controls using cell viability (MTS assay) and caspase-3 activity, with or without caspase-3 selective inhibitor [30].
 

Analytical, diagnostic and therapeutic context of p-xylene

  • The effects produced by oral administration of 500 mg/kg p-xylene or toluene lasted at least 8 hr, while the effect of inhaled p-xylene dissipated within 75 min of removal from the exposure [20].
  • Immobilization of microorganisms on a non-woven polyester textile developed the active biofilm, thereby obtaining biodegradation rates of 81 mg/L . h and 40 mg/L . h for p-xylene and naphthalene, respectively [26].
  • The determination of urinary mercapturic acid, N-acetyl-S-(m-xylyl)-L-cysteine or N-acetyl-S-(p-xylyl)-L-cysteine, was undertaken by HPLC after i.p. administration of m- or p-xylene to rats in order to confirm the structure of thioether which was known to be excreted in small amounts related with the metabolism of m- or p-xylene [31].
  • The major accumulating compounds formed during the degradation of m- and p-xylene by DK17 were isolated by high-pressure liquid chromatography and identified by gas chromatography-mass spectrometric and (1)H nuclear magnetic resonance spectral techniques [32].
  • Inverse gas chromatography (IGC) is used for the analysis of the influence of air relative humidity on the retention of hexane, benzene, toluene and p-xylene in a sandy soil under experimental conditions similar to those typical of soil vapor extraction (SVE) [33].

References

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  2. Cytochrome P450 2B isoenzymes are responsible for the pulmonary bioactivation and toxicity of butylated hydroxytoluene, O,O,S-trimethylphosphorothioate and methylcyclopentadienyl manganese tricarbonyl. Verschoyle, R.D., Wolf, C.R., Dinsdale, D. J. Pharmacol. Exp. Ther. (1993) [Pubmed]
  3. Developmental toxicities of ethylbenzene, ortho-, meta-, para-xylene and technical xylene in rats following inhalation exposure. Saillenfait, A.M., Gallissot, F., Morel, G., Bonnet, P. Food Chem. Toxicol. (2003) [Pubmed]
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  6. Behavioral effects of acute p-xylene inhalation in rats: autoshaping, motor activity, and reversal learning. Bushnell, P.J. Neurotoxicology and teratology. (1988) [Pubmed]
  7. Ototoxicity in rats exposed to ortho-, meta- and para-xylene vapours for 13 weeks. Gagnaire, F., Marignac, B., Langlais, C., Bonnet, P. Pharmacol. Toxicol. (2001) [Pubmed]
  8. Insight into the mechanism of aromatic hydroxylation by toluene 4-monooxygenase by use of specifically deuterated toluene and p-xylene. Mitchell, K.H., Rogge, C.E., Gierahn, T., Fox, B.G. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  9. Peptide inhibitors of enveloped virus infection inhibit phospholipid vesicle fusion and Sendai virus fusion with phospholipid vesicles. Kelsey, D.R., Flanagan, T.D., Young, J., Yeagle, P.L. J. Biol. Chem. (1990) [Pubmed]
  10. Enhanced para-xylene selectivity in the toluene alkylation reaction at ultralow contact time. Breen, J., Burch, R., Kulkarni, M., Collier, P., Golunski, S. J. Am. Chem. Soc. (2005) [Pubmed]
  11. Solid state NMR method for the determination of 3D zeolite framework/sorbate structures: 1H/29Si CP MAS NMR study of the high-loaded form of p-xylene in ZSM-5 and determination of the unknown structure of the low-loaded form. Fyfe, C.A., Diaz, A.C., Grondey, H., Lewis, A.R., Förster, H. J. Am. Chem. Soc. (2005) [Pubmed]
  12. A theoretical study of the alkylation reaction of toluene with methanol catalyzed by acidic mordenite. Vos, A.M., Rozanska, X., Schoonheydt, R.A., van Santen, R.A., Hutschka, F., Hafner, J. J. Am. Chem. Soc. (2001) [Pubmed]
  13. Substrate interactions of benzene, toluene, and para-xylene during microbial degradation by pure cultures and mixed culture aquifer slurries. Alvarez, P.J., Vogel, T.M. Appl. Environ. Microbiol. (1991) [Pubmed]
  14. Organisation of the tmb catabolic operons of Pseudomonas putida TMB and evolutionary relationship with the xyl operons of the TOL plasmid pWW0. Favaro, R., Bernasconi, C., Passini, N., Bertoni, G., Bestetti, G., Galli, E., Dehò, G. Gene (1996) [Pubmed]
  15. Identification of cis-diols as intermediates in the oxidation of aromatic acids by a strain of Pseudomonas putida that contains a TOL plasmid. Whited, G.M., McCombie, W.R., Kwart, L.D., Gibson, D.T. J. Bacteriol. (1986) [Pubmed]
  16. 1-Nitronaphthalene toxicity in rat lung and liver: effects of inhibiting and inducing cytochrome P450 activity. Verschoyle, R.D., Carthew, P., Wolf, C.R., Dinsdale, D. Toxicol. Appl. Pharmacol. (1993) [Pubmed]
  17. Implications of the xylQ gene of TOL plasmid pWW102 for the evolution of aromatic catabolic pathways. Aemprapa, S., Williams, P.A. Microbiology (Reading, Engl.) (1998) [Pubmed]
  18. Changing the ortho/para ratio in aromatic acylation reactions by changing reaction conditions: a mechanistic explanation from kinetic measurements. Effenberger, F., Maier, A.H. J. Am. Chem. Soc. (2001) [Pubmed]
  19. Isolation and expansion of the catabolic potential of a Pseudomonas putida strain able to grow in the presence of high concentrations of aromatic hydrocarbons. Ramos, J.L., Duque, E., Huertas, M.J., Haïdour, A. J. Bacteriol. (1995) [Pubmed]
  20. Acute exposures to p-xylene and toluene alter visual information processing. Dyer, R.S., Bercegeay, M.S., Mayo, L.M. Neurotoxicology and teratology. (1988) [Pubmed]
  21. Effects of p-xylene inhalation on axonal transport in the rat retinal ganglion cells. Padilla, S.S., Lyerly, D.P. Toxicol. Appl. Pharmacol. (1989) [Pubmed]
  22. Human cytochrome P450 isoform specificity in the regioselective metabolism of toluene and o-, m- and p-xylene. Tassaneeyakul, W., Birkett, D.J., Edwards, J.W., Veronese, M.E., Tassaneeyakul, W., Tukey, R.H., Miners, J.O. J. Pharmacol. Exp. Ther. (1996) [Pubmed]
  23. The biotransformation of p-xylene to a toxic aldehyde. Patel, J.M., Harper, C., Drew, R.T. Drug Metab. Dispos. (1978) [Pubmed]
  24. Probing molecular dynamics in chromatographic systems using high-resolution 1H magic-angle-spinning NMR spectroscopy: interaction between p-Xylene and C18-bonded silica. Coen, M., Wilson, I.D., Nicholson, J.K., Tang, H., Lindon, J.C. Anal. Chem. (2004) [Pubmed]
  25. An enantiomeric nanoscale architecture obtained from a pseudoenantiomeric aggregate: covalent fixation of helical chirality formed in self-assembled discotic triazine triamides by chiral amplification. Ishi-i, T., Kuwahara, R., Takata, A., Jeong, Y., Sakurai, K., Mataka, S. Chemistry (Weinheim an der Bergstrasse, Germany) (2006) [Pubmed]
  26. Kinetics of biodegradation of p-xylene and naphthalene and oxygen transfer in a novel airlift immobilized bioreactor. Jajuee, B., Margaritis, A., Karamanev, D., Bergougnou, M.A. Biotechnol. Bioeng. (2007) [Pubmed]
  27. Photodissociation of p-xylene in polar and nonpolar solutions. Fujiwara, M., Mouri, Y., Ariki, K., Tanimoto, Y. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2005) [Pubmed]
  28. Adhesion of different bacterial strains to low-temperature plasma treated biomedical PVC catheter surfaces. Yousefi Rad, A., Ayhan, H., Kisa, U., Pişkin, E. Journal of biomaterials science. Polymer edition. (1998) [Pubmed]
  29. Effect of structure of PEO-PPO-PEO copolymers on reverse micelle formation induced by compressed CO2. Zhang, R., Liu, J., Han, B., He, J., Wang, B., Sun, D. Journal of colloid and interface science. (2004) [Pubmed]
  30. Organic solvent-induced proximal tubular cell toxicity via caspase-3 activation. Al-Ghamdi, S.S., Raftery, M.J., Yaqoob, M.M. J. Toxicol. Clin. Toxicol. (2003) [Pubmed]
  31. High performance liquid chromatographic determination of mercapturic acids in urine of rats administered with m- or p-xylene. Tsujimoto, Y., Noda, T., Moriwaki, H., Tanaka, M. Chemosphere (1998) [Pubmed]
  32. Regioselective oxidation of xylene isomers by Rhodococcus sp. strain DK17. Kim, D., Kim, Y.S., Jung, J.W., Zylstra, G.J., Kim, Y.M., Kim, S.K., Kim, E. FEMS Microbiol. Lett. (2003) [Pubmed]
  33. Column study of the influence of air humidity on the retention of hydrocarbons on soil. García-Herruzo, F., Rodríguez-Maroto, J.M., García-Delgado, R.A., Gómez-Lahoz, C., Vereda-Alonso, C. Chemosphere (2000) [Pubmed]
 
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