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Name Description
id 21
T3DB ID T3D0022
Name Hexachlorobutadiene
Class SmallMolecule
Description Hexachlorobutadiene is a man-made chemical primarily produced as a by-product in the production of carbon tetrachloride and tetrachloroethene. It is also used to make rubber compounds, lubricants, in gyroscopes, as a heat transfer liquid, as a hydraulic fluid, and as a solvent. (L93, L94)
Categories "Industrial/Workplace Toxin", "Pollutant", "Airborne Pollutant", "Synthetic Toxin"
Types "Organic Compound", "Organochloride", "Solvent", "Pollutant", "Industrial/Workplace Toxin", "Synthetic Compound"
Synonyms "1,1,2,3,4, 4-Hexachloro-1,3-butadiene", "1,1,2,3,4,4-hexachloro-1,3-Butadiene", "1,1,2,3,4,4-Hexachloro-buta-1,3-diene", "1,1,2,3,4,4-hexachlorobuta-1,3-diene", "1,3-Hexachlorobutadiene", "Dolen-pur", "HCB", "HCBD", "Hexachlorbutadiene", "Hexachloro-1,3-Butadiene", "Hexachloro-Butadiene", "Hexachlorobuta-1,3-diene", "Hexachlorobutadiene-(1,3)", "Hexachlorobutadiene13", "Perchloro-1,3-butadiene", "Perchlorobutadiene"
CAS Number 87-68-3
Chemical Formula C4Cl6
Average Molecular Mass 260.76
Monoisotopic Mass 257.81
IUPAC Name hexachlorobuta-1,3-diene
Traditional Name hexachlorobutadiene
SMILES ClC(Cl)=C(Cl)C(Cl)=C(Cl)Cl
InChI Identifier InChI=1S/C4Cl6/c5-1(3(7)8)2(6)4(9)10
InChI Key InChIKey=RWNKSTSCBHKHTB-UHFFFAOYSA-N
Kingdom Organic Compounds
Super Class Organohalogen Compounds
Class Vinyl Halides
Sub Class Vinyl Chlorides
Direct Parent Chlorocarbons
Alternate Parents "Chloroalkenes", "Organochlorides"
Geometric Description Aliphatic Acyclic Compounds
Substituents "organochloride", "Aliphatic Acyclic Compound", "Chloroalkene", "Vinyl Chloride", "Haloalkene"
Descriptors
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Membrane"
Biofluids
Tissues
Pathways
State Liquid
Appearance Colorless liquid.
Melting Point -21°C
Boiling Point 210-220°C
Solubility 0.0032 mg/mL at 25 °C [BANERJEE,S et al. (1980)]
LogP
Route of Exposure Oral (L94); inhalation (L94); dermal (L94)
Mechanism of Toxicity It is believed that intermediates produced by modification of the S- 1,1,2,3,4-pentachlorodienyl cysteine derivative metabolite by gamma-glutamyltransferase are responsible for the observed effects on the proximal tubules of the nephrons. These metabolites uncouple oxidative phosphorylation, preventing the generation of ATP, and also inhibit cytochrome c-cytochrome oxidase activity and electron transport. The carcinogenic properties of hexachlorobutadiene are proposed to result from binding of the sulfenic acid degradation product or a thioketene intermediate to cellular DNA. The binding of hexachlorobutadiene to alpha 2u-globulin is believed to be an important factor in its nephrotoxicity. (L94, A54)
Metabolism After absorption, most of the hexachlorobutadiene is carried to the liver, where it is metabolized by a glutathione-mediated pathway. It is initially bioactivated to S-glutathione conjugates which may later be metabolized further by beta-lyases and other enzymes. Hexachlorobutadiene and its metabolites preferentially distribute to the kidney, liver, adipose deposits, and possibly the brain. Metabolites are eventually excreted in the urine and faeces. (L94)
Toxicity LD50: 90 mg/kg (Oral, Rat) (T14) LD50: 175 mg/kg (Intraperitoneal, Rat) (T14) LD50: 1211 mg/kg (Dermal, Rabbit) (T14)
Lethal Dose
Carcinogenicity 3, not classifiable as to its carcinogenicity to humans. (L135)
Uses/Sources Hexachlorobutadiene is primarily produced as a by-product in the production of carbon tetrachloride and tetrachloroethene. It is also used to make rubber compounds, lubricants, in gyroscopes, as a heat transfer liquid, as a hydraulic fluid, and as a solvent. (L94)
Minimum Risk Level Intermediate Oral: 0.0002 mg/kg/day (L134)
Health Effects Hexachlorobutadiene is damaging to the liver and kidney, and may result in fatty liver degeneration, epithelial necrotizing nephritis, central nervous system depression and cyanosis. (L93, L94)
Symptoms Inhalation of hexachlorobutadiene causes nasal irritation and difficulty breathing. (L94)
Treatment As there is no antidote for hexachlorobutadiene, exposure is usually treated symptomatically. (L94)
DrugBank ID
HMDB ID
PubChem Compound ID 6901
ChEMBL ID CHEMBL389950
ChemSpider ID 6635
KEGG Compound ID C11091
UniProt ID 0
OMIM ID 0
ChEBI ID 0
BioCyc ID BUTADIENE
CTD ID C001335
Stitch ID Hexachlorobutadiene
PDB ID
ACToR ID 692
Wikipedia Link
Creation Date 2009-03-06 18:57:56
Update Date 2014-12-24 20:20:54