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Chemical Compound Review:

CCRIS 4722 2,3,4,5-tetrachlorophenol

Synonyms: AG-E-76315, AG-F-65031, AG-L-63215, HSDB 6765, LS-1296, ...

Ahlborg, U.G. et al., Demers, P.A. et al., Dai, M. et al., Friesen, M.C. et al., Mundy, D.E. et al., et al.

Demers, Davies, Friesen, Hertzman, Ostry, Hershler, Teschke,

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Disease relevance of AI3-01682

Stronger associations for non-Hodgkin lymphoma and kidney cancer incidence were observed with pentachlorophenol than with total chlorophenol; no association was observed with tetrachlorophenol [1].
The acute toxicity of the tetrachlorophenols and tetrachloro-p-hydroquinone was studied in mice upon oral and intraperitoneal administration [2].

High impact information on AI3-01682

Based upon the known mechanisms of flavin monooxygenases such as PCP hydroxylase, hydroxylation of PCP should produce tetrachlorobenzoquinone, while hydroxylation of tetrachlorophenol should produce tetrachlorohydroquinone [3].
Cancer and occupational exposure to pentachlorophenol and tetrachlorophenol (Canada) [4].
Partitioning of tetrachlorophenol into lipid bilayers and sarcoplasmic reticulum: effect of length of acyl chains, carbonyl group of lipids and biomembrane structure [5].
Activation of liver microsomes by 2,3,4,5-tetrachlorophenol [6].
Pentachlorophenol (PCP: 25.0 +/- 3.9 ng/ml; mean +/- s.e.m., n = 50) and tetrachlorophenol (TCP: 6.2 +/- 1.6 ng/ml; mean +/- s.e.m., n = 25) were found in all samples [7].

Chemical compound and disease context of AI3-01682

Tetrachloro-p-hydroquinone proved to have low oral toxicity (LD50p.o. 500 mg . kg-1) but was more toxic than the tetrachlorophenols when administered intraperitoneally [2].

Gene context of AI3-01682

Using gas chromatography in combination with ECD and mass spectrometry 14 mono-, di-, tri- and tetrachlorophenols were identified in the urine samples of the workers [8].

Analytical, diagnostic and therapeutic context of AI3-01682

OBJECTIVE: The objective of this study is to assess the carcinogenicity of pentachlorophenol and tetrachlorophenol using data from the BC sawmill workers cohort study [4].
The rapid determination of pentachlorophenol and tetrachlorophenols in animal materials by high-performance liquid chromatography (HPLC) on porous silica is described [9].

References

Impact of the specificity of the exposure metric on exposure-response relationships. Friesen, M.C., Davies, H.W., Teschke, K., Ostry, A.S., Hertzman, C., Demers, P.A. Epidemiology (Cambridge, Mass.) (2007) [Pubmed]
Metabolism of tetrachlorophenols in the rat. Ahlborg, U.G., Larsson, K. Arch. Toxicol. (1978) [Pubmed]
A previously unrecognized step in pentachlorophenol degradation in Sphingobium chlorophenolicum is catalyzed by tetrachlorobenzoquinone reductase (PcpD). Dai, M., Rogers, J.B., Warner, J.R., Copley, S.D. J. Bacteriol. (2003) [Pubmed]
Cancer and occupational exposure to pentachlorophenol and tetrachlorophenol (Canada). Demers, P.A., Davies, H.W., Friesen, M.C., Hertzman, C., Ostry, A., Hershler, R., Teschke, K. Cancer Causes Control (2006) [Pubmed]
Partitioning of tetrachlorophenol into lipid bilayers and sarcoplasmic reticulum: effect of length of acyl chains, carbonyl group of lipids and biomembrane structure. Word, R.C., Smejtek, P. J. Membr. Biol. (2005) [Pubmed]
Activation of liver microsomes by 2,3,4,5-tetrachlorophenol. Süssmuth, R., Ackermann-Schmidt, B., Lingens, F. Mutat. Res. (1980) [Pubmed]
Pentachlorophenol and hexachlorobenzene in serum and urine of the population of Barcelona. Gómez-Catalán, J., To-Figueras, J., Planas, J., Rodamilans, M., Corbella, J. Human toxicology. (1987) [Pubmed]
Occupational exposure to hexachlorocyclohexane. VI. Metabolism of gamma-hexachlorocyclohexane in man. Angerer, J., Maass, R., Heinrich, R. International archives of occupational and environmental health. (1983) [Pubmed]
Determination of pentachlorophenol and related compounds in animal materials by high-performance liquid chromatography and gas chromatography. Mundy, D.E., Machin, A.F. J. Chromatogr. (1981) [Pubmed]

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