| Pentachlorophenol (PCP) is an organochlorine compound used as a pesticide and a disinfectant. First produced in the 1930s, it is marketed under many trade names. It can be found as pure PCP, or as the sodium salt of PCP, the latter of which dissolves easily in water. It can be biodegraded by some bacteria, including Sphingobium chlorophenolicum.
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| InChI=1S/C6HCl5O/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H |
| IZUPBVBPLAPZRR-UHFFFAOYSA-N |
| Oc1c(Cl)c(Cl)c(Cl)c(Cl)c1Cl |
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human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
fungicide
A substance used to destroy fungal pests.
(via aromatic fungicide )
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fungicide
A substance used to destroy fungal pests.
(via aromatic fungicide )
pesticide
Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.
(via organochlorine pesticide )
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View more via ChEBI Ontology
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2,3,4,5,6-pentachlorophenol
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NIST Chemistry WebBook
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PCP
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KEGG COMPOUND
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Pentachlorophenol
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KEGG COMPOUND
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PENTACHLOROPHENOL
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PDBeChem
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102794
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Gmelin Registry Number
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Gmelin
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1285380
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Reaxys Registry Number
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Reaxys
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87-86-5
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CAS Registry Number
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KEGG COMPOUND
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87-86-5
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CAS Registry Number
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ChemIDplus
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87-86-5
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CAS Registry Number
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NIST Chemistry WebBook
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Chen Y, Huang J, Xing L, Liu H, Giesy JP, Yu H, Zhang X (2014)
Effects of multigenerational exposures of D. magna to environmentally relevant concentrations of pentachlorophenol.
Environmental science and pollution research international 21, 234-243 [PubMed:23636589]
[show Abstract]
The re-emergence of schistosomiasis has given rise to ubiquitous concentrations of the primary control agent pentachlorophenol (PCP) in the environment, especially in the surface waters of China. In this study, the effects of environmentally relevant concentrations of PCP, namely, 0.0002, 0.002, 0.02, 0.2, and 2 μmol/L on survival, age at first reproduction, fecundity, length of mothers, and number of molts of Daphnia magna were studied over three generations. The survival of D. magna exposed to 2 μmol/L was significantly affected in the three generations. Toxic effects were enhanced in later generations. Age at first reproduction of F1 and F2 D. magna was significantly slower than that of the controls. The total number of offspring per female exposed to concentrations of 0.002 μmol/L or greater was less (23.5 to 67.6, 9.4 to 73.7, and 3.6 to 83.7%) than that of the controls in the F0, F1, and F2 generations, respectively. The body length of mothers significantly decreased (4.7 to 6.8, 9.6 to 15.1, and 13.3 to 23.2%) after exposure to 0.002 μmol/L or greater than those of unexposed individuals in the F0, F1, and F2 generations, respectively. Dose-response relationships between concentrations of PCP and length and number of molts of D. magna were observed in the F0 to F2 generations. PCP concentrations on the surface waters of China caused adverse effects to D. magna, which increased over successive generations. Significant effects were observed in the third generation. The multigenerational studies were more sensitive than the single-generation experiments. Thus, multigenerational exposure may be more predictive of chronic exposure under field conditions. | Yu LQ, Zhao GF, Feng M, Wen W, Li K, Zhang PW, Peng X, Huo WJ, Zhou HD (2014)
Chronic exposure to pentachlorophenol alters thyroid hormones and thyroid hormone pathway mRNAs in zebrafish.
Environmental toxicology and chemistry 33, 170-176 [PubMed:24123209]
[show Abstract]
Pentachlorophenol (PCP) is frequently detected in the aquatic environment and has been implicated as an endocrine disruptor in fish. In the present study, 4-month-old zebrafish (Danio rerio) were exposed to 1 of 4 concentrations of PCP (0.1, 1, 9, and 27 µg/L) for 70 d. The effects of PCP exposure on plasma thyroid hormone levels, and the expression levels of selected genes, were measured in the brain and liver. The PCP exposure at 27 µg/L resulted in elevated plasma thyroxine concentrations in male and female zebrafish and depressed 3, 5, 3'-triiodothyronine concentrations in males only. In both sexes, PCP exposure resulted in decreased messenger RNA (mRNA) expression levels of thyroid-stimulating hormone β-subunit (tshβ) and thyroid hormone receptor β (trβ) in the brain, as well as increased liver levels of uridine diphosphoglucuronosyl transferase (ugt1ab) and decreased deiodinase 1 (dio1). The authors also identified several sex-specific effects of PCP exposure, including changes in mRNA levels for deiodinase 2 (dio2), cytosolic sulfotransferase (sult1 st5), and transthyretin (ttr) genes in the liver. Environmental PCP exposure also caused an increased malformation rate in offspring that received maternal exposure to PCP. The present study demonstrates that chronic exposure to environmental levels of PCP alters plasma thyroid hormone levels, as well as the expression of genes associated with thyroid hormone signaling and metabolism in the hypothalamic-pituitary-thyroid (HPT) axis and liver, resulting in abnormal zebrafish development. | Vaidyanathan VG, Villalta PW, Sturla SJ (2007)
Nucleobase-dependent reactivity of a quinone metabolite of pentachlorophenol.
Chemical research in toxicology 20, 913-919 [PubMed:17497895]
[show Abstract]
Pentachlorophenol (PCP) is a possible human carcinogen detected widely in the environment. A quinone metabolite of PCP, tetrachloro-1,4-benzoquinone (Cl4BQ), is a reactive electrophile with the capacity to damage DNA by forming bulky covalent DNA adducts. These quinone adducts may contribute to chlorophenol carcinogenesis, but their structures, occurrence, and biological consequences are not known. Previous studies have indicated that several DNA adducts are formed in vivo in rats exposed to Cl4BQ, but these adducts were not identified structurally. In the present study, we have elucidated the structure of new agent-specific DNA adducts resulting from the reaction of dGuo, dCyd, and Thd with Cl4BQ. These have been characterized chemically by liquid chromatography-electrospray ionization mass spectrometry, HPLC, UV, and NMR analysis. Two dGuo adducts and one dCyd adduct resulting from the reaction of double-stranded DNA with Cl4BQ have been identified. The results indicate that, in the structural context of DNA, Cl4BQ reacts most readily with dGuo compared to the other DNA bases and that the mode of Cl4BQ reactivity is dependent on the base structure; i.e., multiple types of adducts are formed. Finally, DNA adducts consistent with Cl4BQ reactions are observed when DNA or dGuo is treated with PCP and a peroxidase-based bioactivating system. |
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