210 2,4-Dichlorophenol 2,4-Dichlorophenol is a chlorinated organic chemical due to environmental exposure, that can be detected in breast milk. The free species of phenols and chlorinated organic appear to be most prevalent in milk (A11269). 120-83-2 8449 C6H4Cl2O 161.963920 White powder. (L159) 45°C 210 °C 1.383 at 60 °C/25 °C 4.5 mg/mL at 20°C 121 °C Oral (L159) ; dermal (L159) Chlorophenols have moderately high lipophilicity. Absorption through the gastrointestinal tract is by simple diffusion and is expected to be both rapid and virtually complete. The chlorophenols are also readily absorbed after dermal exposure. Chlorophenols uncouple mitochondrial oxidative phosphorylation and produce convulsions. At low concentrations, uncoupling produces stimulation of state 4 (resting state) respiration as a result of increased adenosine triphosphatase (ATPase) activity in the absence of a phosphate acceptor. Inhibition of state 3 (active) respiration is also observed. At moderate concentrations, resting respiration is neither stimulated nor inhibited. Significant inhibition of respiration, associated with a breakdown of the electron transport process and decreased ATPase activity, occurs at very high concentrations. (L159) After inhalation and dermal routes, 2,4-DCP is rapidly absorbed and excreted. Data on absorption following oral route are limited to animal studies. When administered intravenously to rats, 2,4-DCP rapidly distributes to the kidney, liver, fat, and brain, with the highest concentrations in the kidney and liver. 2,4-DCP strongly bind to serum proteins, including albumin and globulin. Both human and animal studies indicate that sulfation and glucuronidation are the main metabolic pathways of chlorophenols. 2,4-DCP has been shown to be metabolized into two major metabolites identified as 2-chloro-1,4-hydroxyquinone and 2-chloro-1,4-benzoquinone by microsomal fractions and whole cells of yeast Saccharomyces cerevisiae expressing human cytochrome P-450 3A4. Another metabolite, 1,2,4-hydroxybenzene, was also detected during biotransformation by whole cells but was not observed in microsomal fractions. (L159) 2B, possibly carcinogenic to humans. (L135) Chlorophenols are used as intermediates in the production of dyes and chlorinated pesticides. Exposed pesticide production workers may be at increased risk for soft tissue sarcoma, Hodgkin’s disease, and non-Hodgkin’s lymphoma. Most people are exposed to very low levels of chlorophenols from chlorinated drinking water. (L159) Dermally absorbed doses of chlorophenols are potentially more toxic than orally absorbed doses. Within 20 minutes of being accidentally splashed with 2,4-DCP on his right arm and leg, a worker experienced seizures, collapsed, and died shortly thereafter. Lethargy, tremors, convulsions, and/or central nervous system depression have been reported in chlorophenol-exposed animals. (L159) 2009-03-06T18:58:17Z 2014-12-24T20:21:19Z http://en.wikipedia.org/wiki/2,4-Dichlorophenol C02625 16738 24-DICHLOROPHENOL C004762 2,4-Dichlorophenol 444 true OC1=C(Cl)C=C(Cl)C=C1 C6H4Cl2O InChI=1S/C6H4Cl2O/c7-4-1-2-6(9)5(8)3-4/h1-3,9H InChIKey=HFZWRUODUSTPEG-UHFFFAOYSA-N 163.001 161.963920164 Exogenous Solid 3.06 HMDB04811 CHEMBL1143 8140 Ziegler, Erich; Simmler, Inge. Acid condensation of 2,4-dichlorophenol with trioxymethylene. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1941), 74B 1871-9.