Halogenated aromatic hydrocarbon

The following reactions will assist the student in the identification of halogenated aromatic hydrocarbons. 

Commercial PCBs Toxic and Biochemical Effects. PCBs and related halogenated aromatic hydrocarbons ehcit a diverse spectmm of toxic and biochemical responses in laboratory animals dependent on a number of factors including age, sex, species, and strain of the test animal and the dosing regimen (single or multiple) (27—32). In Bobwhite and Japanese quad, the LC q dose for several different commercial PCB preparations ranged from 600 to 30,000 ppm in the diet the LC q values for mink that were fed Aroclors 1242 and 1254 were 8.6 and 6.7 ppm in the diet, respectively (8,28,33). The... 

Gibson DT, JR Koch, CL Schuld, RE Kallio (1968) Oxidative degradation of aromatic hydrocarbons by microorganisms. II. Metabolism of halogenated aromatic hydrocarbons. Biochemistry 7 3795-3802. 

Peijnenburg WJGM, MJ t Hart, HA den Hollander, D van de Meent, HH Verboom, NL Wolfe (1992) QSARs for predicting reductive transformation constants of halogenated aromatic hydrocarbons in anoxic sediment systems. Environ Toxicol Chem 11 301-314. 

Poland, A., and J. C. Knutson. 1982. 2,3,7,8-Tetrachlorodibenzo-p-dioxin and Related Halogenated Aromatic Hydrocarbons Examination of the Mechanism of Toxicity. Ann. Rev. Pharmacol. Toxicol. 22, 517. 

Hendriks, A.J., H. Pieters, and J. de Boer. 1998. Accumulation of metals, polycyclic (halogenated) aromatic hydrocarbons, and biocides in zebra mussel and eel from the Rhine and Meuse Rivers. Environ. Toxicol. Chem. 17 1885-1898. 

Ishizuka, M., T. Sakiyama, H. Iwata, M. Fukushima, A. Kazusaka, and S. Fujita. 1998. Accumulation of halogenated aromatic hydrocarbons and activities of cytochrome P450 and glutathione 5-transferase in crabs (Eriocheir japonicus) from Japanese rivers. Environ. Toxicol. Chem. 17 1490-1498. 

Sanderson, J.T., S.W. Kennedy, and J.P. Giesy. 1998. In vitro induction of ethoxyresorufin-O-deethylase and porphyrin by halogenated aromatic hydrocarbons in avian primary hepatocytes. Environ. Toxicol. Chem. 17 2006-2018. 

Poland, A., Knutson, J.C. 2,3,7,8-tetrachlorodibenzo-p-dioxin and related halogenated aromatic hydrocarbons examination of the mechanism of toxicity, Ann. Rev.Pharm. Toxicol., 22, 517, 1989. 

Holsapple, M.P. Immunotoxicity of halogenated aromatic hydrocarbons, in Experimental Immunotoxicology, Smialowicz, R.J., Hollsapple, M.P., Eds, CRC Press, Boca Raton, FL. 1996, chap. 14. 

As observed in mammalian models, the immune system of fishes is a sensitive target organ system to evaluate toxicity. For a more thorough review of environmental immunotoxicology in fishes, with reference to specific classes of xenobiotics, readers are referred to several reviews that deal with the subject over a span of nearly three decades [45-47, 54-57], While fish in the environment may be exposed to a variety of xenobiotics, the most frequently investigated xenobiotics are the polycyclic aromatic hydrocarbons (PAHs) and halogenated aromatic hydrocarbons (HAHs) due to the presence and activation of the aryl hydrocarbon receptor (AhR) in fish, and heavy metals due to their ubiquitous environmental distribution. 

Halogen acid furnaces, 13 179 Halogenated alkyl phosphates/ phosphonates, 11 489-496 Halogenated aromatic hydrocarbons (HAHs), 13 135 toxic responses to, 13 138 Halogenated aryloxyacetic acids,... 

Nicolson, W.J., Moore, J.A. (eds) (1979) Health Effects of Halogenated Aromatic Hydrocarbons, New York Academy of Sciences, New York. 

Albro PW. 1979. Problems in analytic methodology Sample handling extraction and cleanup. In Nicholson WJ, Moore JA, eds. Annals of the New York Academy of Sciences, Health Effects of Halogenated Aromatic Hydrocarbons International Symposium, New York, NY, USA, June 24-27, 1978. New York, NY New York Academy of Sciences, 320 19-27. 

The metabolism of 1,4-dichlorobenzene could involve the formation of an arene oxide intermediate, as has been proposed to occur in the oxidative metabolism of many halogenated aromatic hydrocarbons (Jerina and Daly 1974). 1,4-Dichlorobenzene has not been shown to be mutagenic in microbial or mammalian systems, a result that may be viewed as further suggestive evidence that an arene oxide intermediate is not involved in its metabolism. 

Williams RT. 1959. The metabolism of halogenated aromatic hydrocarbons. In Detoxication mechanisms. 2nded. New York, NY John Wiley and Sons, 237-258. 

Clearly, humans are exposed to a complex mixture of CDDs and other halogenated aromatic hydrocarbons such as chlorinated diben-zofurans (CDF) and polychlorinated biphenyls (PCBs). The toxicological concerns resulting from exposure to mixtures, as well as the gaps... 

For halogenated aromatic hydrocarbons like polychlorinated biphenyls (PCBs), polychlorinated dibenzofurans (PCDFs), and polychlorinated dibenzo-p-dioxins (PCDDs) the binding to the aryl hydrocarbon (Ah) receptor regulates their toxicity [89]. The Ah receptor controls the induction of one of the cytochrome P450 enzymes in the liver. Toxic responses such as thymic atrophy, iveight loss, immu-notoxicity and acute lethality are associated ivith the relative affinity of PCBs, PCDFs and PCDDs for the Ah receptor [89]. The quantitative structure-activity relationship (QSAR) models predicting the affinity of the halogenated aromatic hydrocarbons ivith the Ah receptor describe the electron acceptor capability as well as the hydrophobicity and polarizability of the chemicals [89[. 

Schriks, M., Vrabie, C.M., Gutleb, A.C., Faassen, E., Rietjens, I.M.C.M, Murk, A.J. (2006). T-screen to quantify potentiating, antagonistic and thyroid hormone-like activities of poly halogenated aromatic hydrocarbons (PHAHs). Toxicology in vitro, Vol 20, no 4,490-498. 

Mono, di, trihalogenated aliphatic hydrocarbons Halogenated aromatic hydrocarbons HO—... 

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