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Chemical Compound Review

Xylene     1,2-dimethylbenzene

Synonyms: O-XYLENE, o-Xylenes, o-Xylol, Ortho-Xylene, o-XYLENE- D10, ...
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Disease relevance of o-xylene


High impact information on o-xylene


Chemical compound and disease context of o-xylene


Biological context of o-xylene

  • Toluene and o-xylene were completely mineralized to stoichiometric amounts of carbon dioxide, methane, and biomass by aquifer-derived microorganisms under strictly anaerobic conditions [13].
  • In order to study the toluene and o-xylene catabolic genes of Pseudomonas stutzeri OX1, a genomic library was constructed [14].
  • The knockout of each ORF and complementation with the wild-type allele indicated that all six ORFs are essential for the full activity of the toluene/o-xylene monooxygenase in Escherichia coli [15].
  • This explains the pattern of blood levels observed for the C6 to C10 aromates in the rat after inhalation, with o-xylene demonstrating the lowest concentration [16].
  • The psychrophilic bacterium Pseudoalteromonas haloplanktis TAC125, isolated from Antarctic seawater, was used as recipient for a biodegradative gene of the mesophilic Pseudomonas stutzeri OX1. tou cluster, coding for Toluene o-Xylene Monooxygenase (ToMO), was successfully cloned and expressed into a "cold expression" vector [17].

Anatomical context of o-xylene


Associations of o-xylene with other chemical compounds


Gene context of o-xylene

  • Strain T1 is also capable of o-xylene transformation during growth on toluene. o-Xylene does not serve as a source of carbon and is not mineralized [26].
  • Binary experiments with o-xylene, a major compound of gasoline as co-contaminant, imply that all resins preferentially sorb o-xylene over MTBE or TBA, i.e., there is sorption competition [27].
  • For ethylbenzene, m,p-xylene, and o-xylene, the air concentrations were significantly higher in the dry cleaning stores using Solvent V, YuClean, and Super New Cleaner than in those using a PERC mixture [28].

Analytical, diagnostic and therapeutic context of o-xylene

  • RT-PCR experiments show that the two copies of the dioxygenase genes are operonic with the downstream putative catabolic genes and that both operons are induced by o-xylene [3].
  • The limit of detection ranging from 0.6 for benzene to 1.1 microg l(-1) for o-xylene and limit of quantification ranging 2.0-3.6 microg l(-1) are lower that those reached by gas chromatography with flame ionization detection and direct aqueous injection before [29].
  • To evaluate the significance of these exposures, the dermal absorption of o-xylene was assessed in F344 male rats and human volunteers using a combination of real-time exhaled breath analysis and physiologically based pharmacokinetic (PBPK) modeling [30].
  • Human volunteers participating in the study placed both legs into a stainless steel hydrotherapy tub containing an initial concentration of approximately 500 microg/L o-xylene [30].
  • The growth of this bacterial group in an o-xylene-contaminated soil was followed by competitive PCR (cPCR) [31].


  1. Crystal structure of the toluene/o-xylene monooxygenase hydroxylase from Pseudomonas stutzeri OX1. Insight into the substrate specificity, substrate channeling, and active site tuning of multicomponent monooxygenases. Sazinsky, M.H., Bard, J., Di Donato, A., Lippard, S.J. J. Biol. Chem. (2004) [Pubmed]
  2. Isolation and characterization of o-xylene oxygenase genes from Rhodococcus opacus TKN14. Maruyama, T., Ishikura, M., Taki, H., Shindo, K., Kasai, H., Haga, M., Inomata, Y., Misawa, N. Appl. Environ. Microbiol. (2005) [Pubmed]
  3. Identification of a novel dioxygenase involved in metabolism of o-xylene, toluene, and ethylbenzene by Rhodococcus sp. strain DK17. Kim, D., Chae, J.C., Zylstra, G.J., Kim, Y.S., Kim, S.K., Nam, M.H., Kim, Y.M., Kim, E. Appl. Environ. Microbiol. (2004) [Pubmed]
  4. Degradation 1,2-dimethylbenzene by Corynebacterium strain C125. Schraa, G., Bethe, B.M., van Neerven, A.R., Van den Tweel, W.J., Van der Wende, E., Zehnder, A.J. Antonie Van Leeuwenhoek (1987) [Pubmed]
  5. Degradation of o-xylene and m-xylene by a novel sulfate-reducer belonging to the genus Desulfotomaculum. Morasch, B., Schink, B., Tebbe, C.C., Meckenstock, R.U. Arch. Microbiol. (2004) [Pubmed]
  6. X-ray Crystal Structures of Manganese(II)-Reconstituted and Native Toluene/o-Xylene Monooxygenase Hydroxylase Reveal Rotamer Shifts in Conserved Residues and an Enhanced View of the Protein Interior. McCormick, M.S., Sazinsky, M.H., Condon, K.L., Lippard, S.J. J. Am. Chem. Soc. (2006) [Pubmed]
  7. New insights into the activation of o-xylene biodegradation in Pseudomonas stutzeri OX1 by pathway substrates. Arenghi, F.L., Barbieri, P., Bertoni, G., de Lorenzo, V. EMBO Rep. (2001) [Pubmed]
  8. Organization and regulation of meta cleavage pathway genes for toluene and o-xylene derivative degradation in Pseudomonas stutzeri OX1. Arenghi, F.L., Berlanda, D., Galli, E., Sello, G., Barbieri, P. Appl. Environ. Microbiol. (2001) [Pubmed]
  9. Functional characterization and molecular modeling of methylcatechol 2,3-dioxygenase from o-xylene-degrading Rhodococcus sp. strain DK17. Kim, D., Chae, J.C., Jang, J.Y., Zylstra, G.J., Kim, Y.M., Kang, B.S., Kim, E. Biochem. Biophys. Res. Commun. (2005) [Pubmed]
  10. 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]
  11. Characterization of Rhodococcus opacus R7, a strain able to degrade naphthalene and o-xylene isolated from a polycyclic aromatic hydrocarbon-contaminated soil. Di Gennaro, P., Rescalli, E., Galli, E., Sello, G., Bestetti, G. Res. Microbiol. (2001) [Pubmed]
  12. The role of glutathione and cysteine conjugates in the nephrotoxicity of o-xylene in rats. Morel, G., Bonnet, P., Cossec, B., Morel, S., Cour, C., Lambert, A.M., Roure, M.B., Brondeau, M.T. Arch. Toxicol. (1998) [Pubmed]
  13. Anaerobic degradation of toluene and o-xylene by a methanogenic consortium. Edwards, E.A., Grbić-Galić, D. Appl. Environ. Microbiol. (1994) [Pubmed]
  14. Cloning of the genes for and characterization of the early stages of toluene and o-xylene catabolism in Pseudomonas stutzeri OX1. Bertoni, G., Bolognese, F., Galli, E., Barbieri, P. Appl. Environ. Microbiol. (1996) [Pubmed]
  15. Analysis of the gene cluster encoding toluene/o-xylene monooxygenase from Pseudomonas stutzeri OX1. Bertoni, G., Martino, M., Galli, E., Barbieri, P. Appl. Environ. Microbiol. (1998) [Pubmed]
  16. Prediction of in vivo metabolic clearance of 25 different petroleum hydrocarbons by a rat liver head-space technique. Mortensen, B., Eide, I., Zahlsen, K., Nilsen, O.G. Arch. Toxicol. (2000) [Pubmed]
  17. Recombinant expression of Toluene o-Xylene Monooxygenase (ToMO) from Pseudomonas stutzeri OX1 in the marine Antarctic bacterium Pseudoalteromonas haloplanktis TAC125. Siani, L., Papa, R., Di Donato, A., Sannia, G. J. Biotechnol. (2006) [Pubmed]
  18. 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. Park, S.H., Schatz, R.A. J. Toxicol. Environ. Health Part A (1999) [Pubmed]
  19. Biodegradation of benzene, toluene, ethylbenzene, and o-xylene by a coculture of Pseudomonas putida and Pseudomonas fluorescens immobilized in a fibrous-bed bioreactor. Shim, H., Yang, S.T. J. Biotechnol. (1999) [Pubmed]
  20. Methyl-substitution of benzene and toluene in preparations of human bone marrow. Flesher, J.W., Myers, S.R. Life Sci. (1991) [Pubmed]
  21. A chromosomally based tod-luxCDABE whole-cell reporter for benzene, toluene, ethybenzene, and xylene (BTEX) sensing. Applegate, B.M., Kehrmeyer, S.R., Sayler, G.S. Appl. Environ. Microbiol. (1998) [Pubmed]
  22. Spatial and temporal trends of volatile organic compounds (VOC) in a rural area of northern Spain. Parra, M.A., González, L., Elustondo, D., Garrigó, J., Bermejo, R., Santamaría, J.M. Sci. Total Environ. (2006) [Pubmed]
  23. Exposures to benzene and other volatile compounds from active and passive smoking. Wallace, L., Pellizzari, E., Hartwell, T.D., Perritt, R., Ziegenfus, R. Arch. Environ. Health (1987) [Pubmed]
  24. Activity and stability of chemically modified Candida antarctica lipase B adsorbed on solid supports. Koops, B.C., Papadimou, E., Verheij, H.M., Slotboom, A.J., Egmond, M.R. Appl. Microbiol. Biotechnol. (1999) [Pubmed]
  25. Volatile organic compounds in indoor environments in Mumbai, India. Srivastava, P.K., Pandit, G.G., Sharma, S., Mohan Rao, A.M. Sci. Total Environ. (2000) [Pubmed]
  26. Metabolites formed during anaerobic transformation of toluene and o-xylene and their proposed relationship to the initial steps of toluene mineralization. Evans, P.J., Ling, W., Goldschmidt, B., Ritter, E.R., Young, L.Y. Appl. Environ. Microbiol. (1992) [Pubmed]
  27. Sorption of methyl tert-butyl ether (MTBE) and tert-butyl alcohol (TBA) to synthetic resins. Bi, E., Haderlein, S.B., Schmidt, T.C. Water Res. (2005) [Pubmed]
  28. Worker exposure to aromatic volatile organic compounds in dry cleaning stores. Jo, W.K., Kim, S.H. AIHAJ : a journal for the science of occupational and environmental health and safety. (2001) [Pubmed]
  29. Gas chromatographic determination of benzene, toluene, ethylbenzene and xylenes using flame ionization detector in water samples with direct aqueous injection up to 250 microl. Kubinec, R., Adamuscin, J., Jurdáková, H., Foltin, M., Ostrovský, I., Kraus, A., Soják, L. Journal of chromatography. A. (2005) [Pubmed]
  30. Evaluation of the dermal bioavailability of aqueous xylene in F344 rats and human volunteers. Thrall, K., Woodstock, A. J. Toxicol. Environ. Health Part A (2003) [Pubmed]
  31. Identification and characterization of o-xylene-degrading Rhodococcus spp. which were dominant species in the remediation of o-xylene-contaminated soils. Taki, H., Syutsubo, K., Mattison, R.G., Harayama, S. Biodegradation (2007) [Pubmed]
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