Abstract
Hexachloro 1,3-butadiene (HCBD; other synonyms: hexachlorobutadiene;1,1,2,3,4,4-hexachloro-1,3-butadiene; perchlorobutadiene; trade names: C46; Dolen-Pur; CAS No.: 87-68-3) is a colorless liquid with a faint turpentine-like odor. It is practically insoluble in water (5 μg/mL at 20°C) but is soluble in ethanol and diethyl ether. It has a melting point of about -21°C and a specific gravity of 1.675. It is not volatile (22 mm Hg at 100°C) and is a nonflammable, stable compound (Hawley 1977).
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References
Anderson PM, Schultze MO (1965) Cleavage of DCVC by an enzyme of bovine origin. Arch Biochem Biophys 109:593–602.
Badaeva LN (1983) Structural and metabolic indexes of the postnatal neurotoxicity of organohalide pesticides. Dopov Akad Nauk Ukr RSR, Ser B: Geol Kjim Biol Nauki 6:55–58 (Chem Abs 99:83463w, 1983).
Badaeva LN (1986) Potential hazard of the chloroganic pesticide hexachlorobutadiene in the mother-fetus-offspring system. Vrach Delo 6:104–106. (Chem Abst 105:74074w, 1986).
Baggett JM, Berndt WO (1984) Renal and hepatic glutathione concentrations in rats after treatment with hexachloro-1,3-butadiene and citrinin. Arch Toxicol 56:46–49.
Berndt WO, Mehendale HM (1979) Effects of hexachlorobutadiene (HCBD) on renal function and renal organic ion transport in the rat. Toxicology 14:55–65.
Bonhaus DD, Gandolfì AJ (1981) Conjugation and bioactivation of chlorotrifluoroethylene. Life Sci 29:2399–2405.
Davis ME (1984) Changes of hexachlorobutadiene nephrotoxicity after piperonyl butoxide treatment. Toxicology 30:217–225.
Davis ME, Berndt WO, Mehendale HM (1980) Disposition and nephrotoxicity of hexachloro-1,3-butadiene. Toxicology 16:179–191.
Davis ME, Berndt WO, Mehendale HM (1986) Effects of cysteine and diethylmaleate pretreatments on renal function and response to a nephrotoxicant. Arch Toxicol 59:7–11.
Dekant W, Metzler M, Henschler D (1986) Identification of S-1,2-dichlorovinyl-N- acetyl-cysteine as a urinary metabolite of trichloroethylene: A possible explanation for its nephrocarcinogenicity in male rats. Biochem Pharmacol 35:2455–2458.
Derr RF, Schultze MO (1963) The metabolism of 35 S (1,2-dichlorovinyl)-L-cysteine in the rat. Biochem Pharmacol 12:465–474.
Duprat P, Gradiski D (1978) Percutaneous toxicity of hexachlorobutadiene. Acta Pharmacol Toxicol 43:346–353.
Gage JC (1970) The subacute inhalation toxicity of 109 industrial chemicals. Br J Indus Med 27:1–18.
Gehring PJ, MacDougall D (1971) Review of the toxicity of hexachlorobenzene and hexachlorobutadiene. Dow Chemical Co, Midland, MI.
Gandolfi AJ, Nagle RB, Soltis JJ, Piescia FH (1981) Nephrotoxicity of halogenated vinyl cysteine compounds. Res Commun Chem Pathol Pharmacol 33:249–261.
German IV (1986) Level of chromosome aberrations in worker coming into contact with hexachlorobutadiene during production. Gig Tr Prof Zabol 5:57–59. (Chem Abst 105:29129w, 1986).
Gradiski D, Duprat P, Magadur JL, Fayein E (1975) Experimental toxicological study of hexachlorobutadiene. Eur J Toxicol 8:180–187.
Gulko AG, Zimina NI, Shroit IG (1964) Toxicological study of insecticide hexachlorobutadiene. Vopr Gigieny i Sanit Ozdorovl Vneshn Sredy Kishinev Sb 128. (Chem Abst 62:13757c, 1965).
Hardin BD, Bond GP, Sikov MR, Andrew FD, Beliles RP, Niemeier RW (1981) Testing of selected workplace chemicals for teratogenic potential. Scand J Work Environ Health 7 (Suppl 4):66–75.
Harleman JH, Seinen W (1979) Short-term toxicity and reproduction studies in rats with hexachloro-(1,3)-butadiene. Toxicol Appl Pharmacol 47:1–14.
Hassall CD, Gandolfi AJ, Brendel K (1983) Effect of halogenated vinyl cysteine conjugates on renal tubular active transport. Toxicology 26:285–294.
Hawley GG (1977) The Condensed Chemical Dictionary, 9th Ed., New York, Van Nostrand-Reinhold. p 436.
Haworth S, Lawlor T, Mortelmans K, Speck W, Zeiger E (1983) Salmonella mutagenicity test results for 250 chemicals. Environ Mutagenesis 5 (Suppl 1):3–142.
Hook JB, Rose MS, Lock EA (1982) The nephrotoxicity of hexachloro-1:3-butadiene in the rat: Studies of organic anion and cation transport in renal slices and the effect of monooxygenase inducers. Toxicol Appl Pharmacol 65:373–382.
Hook JB, Ishmael J, Lock EA (1983) Nephrotoxicity of hexachloro-1:3-butadiene in the rat: The effect of age, sex, and strain. Toxicol Appl Pharmacol 67:122–131.
IARC (1979) IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. 20:179–193.
Igwe OJ (1986) Biologically active intermediates generated by the reduced glutathione conjugation pathway. Toxicological implications. Biochem Pharmacol 35:2987–2994.
Ishmael J, Pratt I, Lock EA (1982) Necrosis of the pars recta (S3 segment) of the rat kidney produced by hexachloro 1:3 butadiene. J Pathol 138:99–113.
Ishmael J, Pratt I, Lock EA (1984) Hexachloro-1:3-butadiene-induced renal tubular necrosis in the mouse. J Pathol 142:195–203.
Jaffe DR, Hassall CD, Brendal K, Gandolfi AJ (1983) In vivo and in vitro nephrotoxicity of the cysteine conjugate of hexachlorobutadiene. J Toxicol Environ Health 11:857–867.
Jones TW, Gerdes RG, Ormstad K, Orrenius S (1985) The formation of both a mono- and a bis-substituted glutathione conjugate of hexachlorobutadiene by isolated hepatocytes and following in vivo administration to the rat. Chem Biol Interactions 56:251–267.
Kluwe WM, McNish R, Smithson K, Hook JB (1981) Depletion by 1,2-dibromoethane, 1,2-dibromo-3-chloropropane, tris(2,3-dibromopropyl) phosphate, and hexachloro -1,3-butadiene of reduced non-protein sulfhydryl groups in target and non-target organs. Biochem Pharmacol 30:2265–2271.
Kluwe WM, Harrington FW, Cooper SE (1982) Toxic effects of organohalide compounds on renal tubular cells in vivo and in vitro. J Pharmacol Exp Therapeut 220:597–603.
Kociba RJ, Keyes DG, Jersey GC, Ballard JJ, Dittenber DA, Quast JF, Wade CE, Humiston CG, Schwetz BA (1977) Results of a two year chronic toxicity study with hexachlorobutadiene in rats. Am Indus Hyg Assoc J 38:589–602.
Lock EA, Ishmael J (1979) The acute toxic effects of hexachlorobutadiene on the rat kidney. Arch Toxicol 43:47–57.
Lock EA, Ishmael J (1981) Hepatic and renal nonprotein sulfhydryl concentration following toxic doses of hexachloro-1,3-butadiene in the rat: The effect of Aroclor 1254, phenobarbitone, or SKF 525A treatment. Toxicol Appl Pharmacol 57:79–87.
Lock EA, Ishmael J (1982) The hepatotoxicity and nephrotoxicity of hexachlorobutadiene. Adv Pharmacol Ther Proc Int Congr, 8th 5:87–96.
Lock EA, Ishmael J (1985) Effect of the organic acid transport inhibitor prebenecid on renal cortical uptake and proximal tubular toxicity of hexachloro-1,3-butadiene and its conjugates. Toxicol Appl Pharmacol 81:32–42.
Lock EA, Odum J, Ormond P (1986) Transport of N-acetyl-S-pentachloro-1,3-butadi- enylcysteine by rat renal cortex. Arch Toxicol 59:12–15.
Lock EA, Pratt I, Ishmael J (1985) Hexachloro-1:3-butadiene-induced hydropic changes in mouse liver. J Appl Toxicol 5:74–79.
Mailhes JB, Schwetz BA, Patton PC, Lisowe RW (1974) Cytogenetic effects of hexachlorobutadiene on rat bone marrow cells. Dow Chemical Co., Midland, MI.
Murzakaev FG (1963) Toxicity data for hexachlorobutadiene and its intermediates. Farmakol i Toksikol 26:750. (Chem Abst 60:137766, 1964).
Murzakaev FG (1967) Action exerted by low hexachlorobutadiene doses on the activity of the central nervous system and morphological changes in animals so poisoned. Gig Tr Prof Zabol 11:23–28. (Chem Abst 67:31040a, 1967).
Nash JA, King LJ, Lock EA, Green T (1984) The metabolism and disposition of hexachloro-1:3-butadiene in the rat and its relevance to nephrotoxicity. Toxicol Appl Pharmacol 73:124–137.
Poteryaeva GE (1966) Effect of hexachlorobutadiene on the offspring of albino rats. Gig i Sanot 31:331–335.
Rannug U, Gothe R, Wachtmeister CA (1976) The mutagenicity of chloroethylene oxide, chloroacetaldehyde, 2-chloroethanol and chloroacetic acid, conceivable metabolites of vinyl chloride. Chem Biol Interact 12:251–263.
Rapson WH, Nazar MA, Butsky VV (1980) Mutagenicity produced by aqueous chlorination of organic compounds. Bull Environ Contam Toxicol 24:590–596.
Reichert D (1982) Distribution, elimination, and metabolism of hexachloro(1,3)butadiene in rats. Naunyn-Schmeideberg’s Arch Pharmacol 319 (Suppl ):R17 (Abstract).
Reichert D, Neudecker T, Spengler U, Henschler D (1983) Mutagenicity of dichloroacetylene and its degradation products trichloroacetyl chloride, trichloroacryloyl chloride and hexachlorobutadiene. Mutation Res 117:21–29.
Reichert D, Neudecker T, Schutz S (1984) Mutagenicity of hexachlorobutadiene, perchlorobetenoic acid and perchlorobutenoic acid chloride. Mutation Res 137:89–93.
Reichert D, Schutz S (1986) Mercapturic acid formation in an activation and intermediary step in the metabolism of hexachlorobutadiene. Biochem Pharmacol 35:1271–1275.
Reichert D, Schutz S, Metzler M (1985) Excretion pattern and metabolism of hexachlorobutadiene in rats. Biochem Pharmacol 34:499–505.
Rush GF, Smith JH, Newton JF, Hook JB (1984) Chemically induced nephrotoxicity: Role of metabolic activation. CRC Crit Rev Toxicol 13:99–160.
Schiffmann D, Reichert D, Henschler D (1984) Induction of morphological transformation and unscheduled DNA synthesis in Syrian hamster embryo fibroblasts by hexachlorobutadiene and its putative metabolite pentachlorobutenoic acid. Cancer Lett 23:297–305.
Schwetz BA, Norris JM, Kociba RJ, Keeler PA, Cornier RF, Gehring PJ (1974) Reproduction study in Japanese Quail fed hexachlorobutadiene for 90 days. Toxicol Appl Pharmacol 30:255–265.
Schwetz BA, Smith FA, Humiston CG, Quast JF, Kociba RJ (1977) Results of a reproduction study in rats fed diets containing hexachlorobutadiene. Toxicol Appl Pharmacol 42:387–398.
Simmon VF, Kauhaneny K, Mortelmans K, Tardiff R (1978) Mutagenic activity of chemicals identified in drinking water. Mutation Res 53:262 (Abstract).
Stott WT, Quast JF, Watanabe PG (1981) Differentiation of the mechanisms of oncogenicity of 1,4-dioxane and 1,3-hexachlorobutadiene in the rat. Toxicol Appl Pharmacol 60:287–300.
Tardiff RG, Carlson GP, Simmon V (1976) Halogenated organics in tap water: a toxicological evaluation, in “The Environmental Impact of Water Chlorination”, Jolley RL (ed), Natl. Tech. Infor. Serv., Springfield, VA. pp 213–227.
Theiss JC, Stoner GD, Shimkin MB, Weisburger EK (1977) Test for carcinogenicity of organic contaminates of United States drinking waters by pulmonary tumor response in strain A mice. Cancer Res 37:2717–2720.
Tomisawa H, Fukazawa H, Ichihara S, Tateichi M (1986) A novel pathway for formation of thiol-containing metabolites from cysteine conjugates. Biochem Pharmacol 35:2270–2272.
US EPA (1975) Survey of Industrial Processing Data, Task I-Hexachlorobenzene and Hexachlorobutadiene Pollution from Chlorocarbon Processing, PB-243 641, Natl. Tech. Infor. Serv., Springfield, VA.
US EPA (1980) Ambient Water Quality Criteria for Hexachlorobutadiene, PB81-117640, Natl. Tech. Infor. Serv., Springfield, VA.
Wild D, Schutz S, Reichert D (1986) Mutagenicity of the mercapturic acid and other S-containing derivatives of hexachloro-1,3-butadiene. Carcinogenesis 7:431–434.
Wolf CR, Berry PN, Nash JA, Green T, Lock EA (1984) Role of microsomal and cytosolic glutathione S-transferases in the conjugation of hexachloro-1:3-butadiene and its possible relevance to toxicity. J Pharm Exp Ther 228:202–208.
Woodruff RC, Mason JM, Valencia R, Zimmering S (1985) Chemical mutagenesis testing in Drosophila. V. Results of 53 coded compounds tested for the National Toxicology Program. Environ Mutagenesis 7:677–702.
Yang RSH, Abdo KM, Elwell MR, Levy AC, Brennecke LH (1987) Subchronic toxicology studies of hexachloro-1,3-butadiene (HCBD) in B6C3F1 mice following dietary incorporation. Toxicologist 7:271. (Abstract).
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Yang, R.S.H. (1988). Hexachloro-1,3-Butadiene: Toxicology, Metabolism, and Mechanisms of Toxicity. In: Ware, G.W. (eds) Reviews of Environmental Contamination and Toxicology. Reviews of Environmental Contamination and Toxicology, vol 101. Springer, New York, NY. https://doi.org/10.1007/978-1-4612-3770-9_4
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DOI: https://doi.org/10.1007/978-1-4612-3770-9_4
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