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Chemical Compound Review

Chlorbenzol     chlorobenzene

Synonyms: Chlorbenzene, Chlorobenzen, Chlorobenzol, Clorobenzene, PhCl, ...
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Disease relevance of chlorobenzene


Psychiatry related information on chlorobenzene

  • The mechanism of monochlorobenzene-induced liver injury and the possible aggravating role of chronic alcohol consumption are discussed [6].
  • The pattern of chlorobenzene and PCB homologues found in wolf liver are more similar to those found in marten (Martes americana) and other carnivores than caribou (Rangifer tarandus), perhaps reflecting similarities in food habits and metabolic capacities [7].

High impact information on chlorobenzene


Chemical compound and disease context of chlorobenzene


Biological context of chlorobenzene

  • We used this approach for detecting the products of the toluene-dioxygenase-catalyzed hydroxylation of chlorobenzene and to screen large mutant libraries of Pseudomonas putida cytochrome P450cam by fluorescence digital imaging [15].
  • This result suggests that the presence of multiple copies of the clc gene cluster was a prerequisite for the growth of P. putida RR22 on chlorobenzene and that amplification of the element was positively selected for in the presence of chlorobenzene [16].
  • Analysis of one of the regions of catabolic plasmid pP51 which encode chlorobenzene metabolism of Pseudomonas sp. strain P51 revealed that the tcbA and tcbB genes for chlorobenzene dioxygenase and dehydrogenase are located on a transposable element, Tn5280 [17].
  • The unique reconstruction of formation of a metabolic pathway through the activity of IS elements and a genomic island in the chlorobenzene-degrading strain JS705 demonstrated how pathway evolution can occur under natural conditions in a few 'steps' [18].
  • The TecA chlorobenzene dioxygenase and the TodCBA toluene dioxygenase exhibit substantial sequence similarity yet have different substrate specificities [19].

Anatomical context of chlorobenzene


Associations of chlorobenzene with other chemical compounds


Gene context of chlorobenzene

  • GSH-S-epoxide transferase (GSH-S-transferase E) activity was indicated in both species; neither species effected the conjugation of bromo- or chlorobenzene [28].
  • The Kyodai nitration of toluene and chlorobenzene has been examined in the presence of a solid inorganic catalyst (montmorillonite K10, zeolite HZSM-5, or HBEA-25) [29].
  • The previously reported triphosphino/trithiolato-ruthenium anion, [tris-(2-diphenylphosphinothia-phenolato)ruthenium(II)](-), [Ru(DPPBT)(3)](-), has been isolated as the PPN salt (PPN = bis(triphenylphosphoranylidene) ammonium), 1, from chlorobenzene/ether as light-orange crystalline plates, and the X-ray crystal structure has been determined [30].
  • The degradation of chlorobenzene was investigated with the specially chosen strain Methylocystis sp. GB 14 DSM 12955, using 23 ml headspace vials and in a soil column filled with quaternary aquifer material from a depth of 20 m [31].
  • HDTMA-modified soil has a higher ability to sorb chlorobenzene from simulated groundwater than unmodified soil [32].

Analytical, diagnostic and therapeutic context of chlorobenzene

  • 4c crystallizes from chlorobenzene as 4c(ClPh).0.5PhCl, which has been characterized by X-ray crystallography [33].
  • PCR analysis of the genetic environment of the tec genes indicated high similarity to the transposon-organized catabolic tcb chlorobenzene degradation genes of Pseudomonas sp. strain P51 [3].
  • Elimination capacities observed in the bioreactor were much higher than those previously reported for biotrickling filters treating MCB containing gas streams: 300 to 450 g m(-3) h(-1) [34].
  • The preparation and crystallization from chlorobenzene leads to a new crystalline phase that has been structurally characterized [35].
  • Stochastic simulation of hepatic preneoplastic foci development for four chlorobenzene congeners in a medium-term bioassay [36].


  1. The broad substrate chlorobenzene dioxygenase and cis-chlorobenzene dihydrodiol dehydrogenase of Pseudomonas sp. strain P51 are linked evolutionarily to the enzymes for benzene and toluene degradation. Werlen, C., Kohler, H.P., van der Meer, J.R. J. Biol. Chem. (1996) [Pubmed]
  2. Transformation of chlorinated benzenes and toluenes by Ralstonia sp. strain PS12 tecA (tetrachlorobenzene dioxygenase) and tecB (chlorobenzene dihydrodiol dehydrogenase) gene products. Pollmann, K., Beil, S., Pieper, D.H. Appl. Environ. Microbiol. (2001) [Pubmed]
  3. Genetic and biochemical analyses of the tec operon suggest a route for evolution of chlorobenzene degradation genes. Beil, S., Timmis, K.N., Pieper, D.H. J. Bacteriol. (1999) [Pubmed]
  4. Construction of chlorobenzene-utilizing recombinants by progenitive manifestation of a rare event. Kröckel, L., Focht, D.D. Appl. Environ. Microbiol. (1987) [Pubmed]
  5. Purification and characterization of chlorobenzene cis-dihydrodiol dehydrogenase from Xanthobacter flavus 14p1. Spiess, E., Görisch, H. Arch. Microbiol. (1996) [Pubmed]
  6. Severe monochlorobenzene-induced liver cell necrosis. Babany, G., Bernuau, J., Cailleux, A., Cadranel, J.F., Degott, C., Erlinger, S., Benhamou, J.P. Gastroenterology (1991) [Pubmed]
  7. Contaminant residue levels in arctic wolves (Canis lupus) from the Yukon Territory, Canada. Gamberg, M., Braune, B.M. Sci. Total Environ. (1999) [Pubmed]
  8. Engineering a recombinant Deinococcus radiodurans for organopollutant degradation in radioactive mixed waste environments. Lange, C.C., Wackett, L.P., Minton, K.W., Daly, M.J. Nat. Biotechnol. (1998) [Pubmed]
  9. Mechanisms of molecular manipulation with the scanning tunneling microscope at room temperature: chlorobenzene/si(111)-(7 x 7). Sloan, P.A., Hedouin, M.F., Palmer, R.E., Persson, M. Phys. Rev. Lett. (2003) [Pubmed]
  10. Structural determinants of HERG channel block by clofilium and ibutilide. Perry, M., de Groot, M.J., Helliwell, R., Leishman, D., Tristani-Firouzi, M., Sanguinetti, M.C., Mitcheson, J. Mol. Pharmacol. (2004) [Pubmed]
  11. Degradation of 1,2-dichlorobenzene by a Pseudomonas sp. Haigler, B.E., Nishino, S.F., Spain, J.C. Appl. Environ. Microbiol. (1988) [Pubmed]
  12. Low-frequency horizontal transfer of an element containing the chlorocatechol degradation genes from Pseudomonas sp. strain B13 to Pseudomonas putida F1 and to indigenous bacteria in laboratory-scale activated-sludge microcosms. Ravatn, R., Zehnder, A.J., van der Meer, J.R. Appl. Environ. Microbiol. (1998) [Pubmed]
  13. Microbial dynamics in a continuous stirred tank bioreactor exposed to an alternating sequence of organic compounds. Ferreira Jorge, R.M., Livingston, A.G. Biotechnol. Bioeng. (2000) [Pubmed]
  14. Microorganisms degrading chlorobenzene via a meta-cleavage pathway harbor highly similar chlorocatechol 2,3-dioxygenase-encoding gene clusters. Göbel, M., Kranz, O.H., Kaschabek, S.R., Schmidt, E., Pieper, D.H., Reineke, W. Arch. Microbiol. (2004) [Pubmed]
  15. A high-throughput digital imaging screen for the discovery and directed evolution of oxygenases. Joo, H., Arisawa, A., Lin, Z., Arnold, F.H. Chem. Biol. (1999) [Pubmed]
  16. Chromosomal integration, tandem amplification, and deamplification in Pseudomonas putida F1 of a 105-kilobase genetic element containing the chlorocatechol degradative genes from Pseudomonas sp. Strain B13. Ravatn, R., Studer, S., Springael, D., Zehnder, A.J., van der Meer, J.R. J. Bacteriol. (1998) [Pubmed]
  17. Identification of a novel composite transposable element, Tn5280, carrying chlorobenzene dioxygenase genes of Pseudomonas sp. strain P51. van der Meer, J.R., Zehnder, A.J., de Vos, W.M. J. Bacteriol. (1991) [Pubmed]
  18. Evolution of a chlorobenzene degradative pathway among bacteria in a contaminated groundwater mediated by a genomic island in Ralstonia. Müller, T.A., Werlen, C., Spain, J., Van Der Meer, J.R. Environ. Microbiol. (2003) [Pubmed]
  19. Identification of chlorobenzene dioxygenase sequence elements involved in dechlorination of 1,2,4,5-tetrachlorobenzene. Beil, S., Mason, J.R., Timmis, K.N., Pieper, D.H. J. Bacteriol. (1998) [Pubmed]
  20. Metobolism of chlorobenzene with hepatic microsomes and solubilized cytochrome P-450 systems. Selander, H.G., Jerina, D.M., Daly, J.W. Arch. Biochem. Biophys. (1975) [Pubmed]
  21. The formation of chlorobenzene and benzene by the reductive metabolism of lindane in rat liver microsomes. Baker, M.T., Nelson, R.M., Van Dyke, R.A. Arch. Biochem. Biophys. (1985) [Pubmed]
  22. The liver, kidney, and thyroid toxicity of chlorinated benzenes. den Besten, C., Vet, J.J., Besselink, H.T., Kiel, G.S., van Berkel, B.J., Beems, R., van Bladeren, P.J. Toxicol. Appl. Pharmacol. (1991) [Pubmed]
  23. Demonstration of chlorobenzene-induced DNA damage in mouse lymphocytes using the single cell gel electrophoresis assay. Vaghef, H., Hellman, B. Toxicology (1995) [Pubmed]
  24. Strain stability in biological systems treating recalcitrant organic compounds. Emanuelsson, E.A., Baptista, I.I., Mantalaris, A., Livingston, A.G. Biotechnol. Bioeng. (2005) [Pubmed]
  25. Thermal desorption-gas chromatography for the determination of benzene, aniline, nitrobenzene and chlorobenzene in workplace air. Patil, S.F., Lonkar, S.T. J. Chromatogr. (1992) [Pubmed]
  26. Degradation of chlorobenzenes by a strain of Acidovorax avenae isolated from a polluted aquifer. Monferrán, M.V., Echenique, J.R., Wunderlin, D.A. Chemosphere (2005) [Pubmed]
  27. Ultrasonic degradation of trichloroethylene and chlorobenzene at micromolar concentrations: kinetics and modelling. Dewulf, J., Van Langenhove, H., De Visscher, A., Sabbe, S. Ultrasonics sonochemistry. (2001) [Pubmed]
  28. Glutathione conjugation of some xenobiotics by Ascaris suum and Moniezia expansa. Douch, P.G., Buchanan, L.L. Xenobiotica (1978) [Pubmed]
  29. Regioselective double Kyodai nitration of toluene and chlorobenzene over zeolites. high preference for the 2,4-dinitro isomer at the second nitration stage. Peng, X., Suzuki, H. Org. Lett. (2001) [Pubmed]
  30. Dichloromethane alkylates a trithiolato-ruthenium complex to yield a methylene-bridged thioether core. Synthesis and structural comparison to the thiolato-ruthenium precursor. Grapperhaus, C.A., Poturovic, S., Mashuta, M.S. Inorganic chemistry. (2002) [Pubmed]
  31. Cometabolic degradation of chlorinated aromatic compounds. Jechorek, M., Wendlandt, K.D., Beck, M. J. Biotechnol. (2003) [Pubmed]
  32. Sorption and cosorption of organic contaminant on surfactant-modified soils. Gao, B., Wang, X., Zhao, J., Sheng, G. Chemosphere (2001) [Pubmed]
  33. Cationic aluminum alkyl complexes incorporating aminotroponiminate ligands. Korolev, A.V., Ihara, E., Guzei, I.A., Young, V.G., Jordan, R.F. J. Am. Chem. Soc. (2001) [Pubmed]
  34. Bioscrubbing of waste gas-substrate absorber to avoid instability induced by inhibition kinetics. Oliveira, T.A., Livingston, A.G. Biotechnol. Bioeng. (2003) [Pubmed]
  35. Structure of the deoxymyoglobin model [Fe(TPP)(2-MeHIm)] reveals unusual porphyrin core distortions. Ellison, M.K., Schulz, C.E., Scheidt, W.R. Inorganic chemistry. (2002) [Pubmed]
  36. Stochastic simulation of hepatic preneoplastic foci development for four chlorobenzene congeners in a medium-term bioassay. Ou, Y.C., Conolly, R.B., Thomas, R.S., Gustafson, D.L., Long, M.E., Dobrev, I.D., Chubb, L.S., Xu, Y., Lapidot, S.A., Andersen, M.E., Yang, R.S. Toxicol. Sci. (2003) [Pubmed]
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