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Chemical Compound Review:

PubChem3673 4-chloro-2-methyl-phenol

Synonyms: CHEMBL194121, SureCN171059, NSC-2851, CCRIS 1939, CHEBI:1800, ...

Müller, R.H. et al., Lechner, U. et al., Carralero, V. et al., Nickel, K. et al., Pozo, O. et al., et al.

Williams, Harrison, Carlick, Crowley,

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Disease relevance of NSC2851

Cell extracts of Sphingomonas herbicidovorans MH grown on (R)-mecoprop contained an enzyme activity that selectively converted (R)-mecoprop to 4-chloro-2-methylphenol, whereas extracts of cells grown on (S)-mecoprop contained an enzyme activity selective for the S enantiomer [1].
Toxicity of 4-chloro-O-cresol to rat: I. Light microscopy and chemical observations [2].

High impact information on NSC2851

The Tyr-Au(coll)-graphite-Teflon biosensor exhibited suitable amperometric responses at -0.10V for the different phenolic compounds tested (catechol; phenol; 3,4-dimethylphenol; 4-chloro-3-methylphenol; 4-chlorophenol; 4-chloro-2-methylphenol; 3-methylphenol and 4-methylphenol) [3].
A rapid and sensitive LC-electrospray tandem mass spectrometry method has been developed for the quantitation of 4-chloro-2-methylphenoxyacetic acid (MCPA) and 4-chloro-2-methylphenol in both water and soil samples [4].
Under nitrate-reducing conditions (S)-mecoprop does not degrade, but (R)-mecoprop degrades with zero-order kinetics at 0.65 mg l(-1) day(-1) to produce a stoichiometric equivalent amount of 4-chloro-2-methylphenol [5].
In the absence of substrate the occurrence of a pseudo catalytic activity is shown to be due to the hydrolysis of the Fast Red TR with the subsequent production of 4-chloro-2-methylphenol [6].
From concrete debris of a demolished herbicide production plant several Gram-negative bacterial strains were isolated, which exhibit metabolic capabilities for the degradation of 2,4-dichlorophenol (DCP)l), 4-chloro-2-methylphenol (MCP) and 4-chlorophenol (4-CP), while 2-chlorophenol (2-CP) was degraded at a slower rate [7].

Biological context of NSC2851

Identification of 4-chloro-2-methylphenol as a soil degradation product of ring-labelled [14C]mecoprop [8].

Gene context of NSC2851

Toxicity of 4-chloro-o-cresol to fish. Light microscopy and chemical analysis of the tissue [9].

Analytical, diagnostic and therapeutic context of NSC2851

The Gram-negative strain S1, isolated from activated sludge, metabolized 4-chloro-2-methylphenol by an inducible pathway via a modified ortho-cleavage route as indicated by a transiently secreted intermediate, identified as 2-methyl-4-carboxymethylenebut-2-en-4-olide by gas chromatography/mass spectrometry [10].

References

Involvement of two alpha-ketoglutarate-dependent dioxygenases in enantioselective degradation of (R)- and (S)-mecoprop by Sphingomonas herbicidovorans MH. Nickel, K., Suter, M.J., Kohler, H.P. J. Bacteriol. (1997) [Pubmed]
Toxicity of 4-chloro-O-cresol to rat: I. Light microscopy and chemical observations. Hattula, M.L., Reunanen, H., Arstila, A.U. Bulletin of environmental contamination and toxicology. (1979) [Pubmed]
Development of a high analytical performance-tyrosinase biosensor based on a composite graphite-Teflon electrode modified with gold nanoparticles. Carralero, V., Mena, M.L., Gonzalez-Cort??s, A., Y????ez-Sede??o, P., Pingarr??n, J.M. Biosensors & bioelectronics. (2006) [Pubmed]
Determination of the herbicide 4-chloro-2-methylphenoxyacetic acid and its main metabolite, 4-chloro-2-methylphenol in water and soil by liquid chromatography-electrospray tandem mass spectrometry. Pozo, O., Pitarch, E., Sancho, J.V., Hernández, F. Journal of chromatography. A. (2001) [Pubmed]
Changes in enantiomeric fraction as evidence of natural attenuation of mecoprop in a limestone aquifer. Williams, G.M., Harrison, I., Carlick, C.A., Crowley, O. J. Contam. Hydrol. (2003) [Pubmed]
The estimation of serum acid phosphatase using alpha-naphthyl phosphate as substrate: observations on the use of Fast Red TR salt in the assay. Cooper, J.D., Turnell, D.C., Price, C.P. Clin. Chim. Acta (1982) [Pubmed]
Degradation of various chlorophenols under alkaline conditions by gram-negative bacteria closely related to Ochrobactrum anthropi. Müller, R.H., Jorks, S., Kleinsteuber, S., Babel, W. J. Basic Microbiol. (1998) [Pubmed]
Identification of 4-chloro-2-methylphenol as a soil degradation product of ring-labelled [14C]mecoprop. Smith, A.E. Bulletin of environmental contamination and toxicology. (1985) [Pubmed]
Toxicity of 4-chloro-o-cresol to fish. Light microscopy and chemical analysis of the tissue. Hattula, M.L., Reunanen, H., Wasenius, V.M., Krees, R., Arstila, A.U. Bulletin of environmental contamination and toxicology. (1979) [Pubmed]
Degradation of 4-chloro-2-methylphenol by an activated sludge isolate and its taxonomic description. Lechner, U., Baumbach, R., Becker, D., Kitunen, V., Auling, G., Salkinoja-Salonen, M. Biodegradation (1995) [Pubmed]

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