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β-Hexachlorocyclohexane

β-Hexachlorocyclohexane (β-HCH) is an organochloride which is one of the isomers of hexachlorocyclohexane (HCH).[1] It is a byproduct of the production of the insecticide lindane (γ-HCH). It is typically constitutes 5–14% of technical-grade lindane,[2] though it has not been produced or used in the United States since 1985.[1] As of 2009, the Stockholm Convention on Persistent Organic Pollutants classified α-hexachlorocyclohexane and β-HCH as persistent organic pollutants (POPs), due to the chemical's ability to persist in the environment, bioaccumulative, biomagnifying, and long-range transport capacity.

β-Hexachlorocyclohexane
Names
Preferred IUPAC name
(1r,2r,3r,4r,5r,6r)-1,2,3,4,5,6-Hexachlorocyclohexane
Other names
β-HCH
β-Benzenehexachloride
β-BHC
Identifiers
  • 319-85-7 Y
3D model (JSmol)
  • Interactive image
1907338
ChEBI
  • CHEBI:28428 Y
ChEMBL
  • ChEMBL389022 Y
ChemSpider
  • 10468512 Y
ECHA InfoCard 100.005.703
EC Number
  • 206-271-3
KEGG
  • C06988
UNII
  • YM80ODM9PD Y
  • DTXSID7020685
  • InChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3+,4+,5-,6- Y
    Key: JLYXXMFPNIAWKQ-CDRYSYESSA-N Y
  • InChI=1/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3+,4+,5-,6-
    Key: JLYXXMFPNIAWKQ-CDRYSYESBR
  • Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@H](Cl)[C@@H](Cl)[C@@H]1Cl
Properties
C6H6Cl6
Molar mass 290.83 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

This pesticide was widely used during the 1960s and 1970s, particularly on cotton plants. Although banned as a pesticide more than 30 years ago, traces of beta-HCH can still be found in water and soil. Animal studies show that organochlorine pesticides, including beta-HCH, are neurotoxic, cause oxidative stress, and damage the brain's dopaminergic system. Human studies show that exposure to beta-HCH is linked to Parkinson's and Alzheimer's disease.[3] β-HCH was present in elevated levels in some patients as recently as 2009. It was manufactured by exhausting chlorination of benzene and for this reason was called erroneously β-BHC. This synonym still persists.

In March 2005, the Italian National Monitoring System on Chemical Residuals in Food of Animal Origin detected levels of the pesticide β-HCH that were 20 times higher than the legal limit of 0.003 mg/kg in bulk milk from a dairy farm in the Sacco River valley. β-HCH, a lindane isomer and possible human carcinogen, was subsequently found in milk from several neighboring farms. A study was therefore undertaken to evaluate the extent and risk factors for contamination.[4][5]

See also edit

References edit

  1. ^ a b Toxicological Profile for Alpha-, Beta-, Gamma-, and Delta-Hexachlorocyclohexane, U.S. Department of Health and Human Services, Agency for Toxic Substances and Disease Registry, August 2005
  2. ^ beta-hexachlorocyclohexane (Beta HCH) July 20, 2008, at the Wayback Machine, Draft Risk Profile, May 2007
  3. ^ Medscape Medical News, Pesticide Exposure Linked to Parkinson's, Alzheimer's Disease, July 2009
  4. ^ Sala M, Caminiti A, Rombolà P, Volpe A, Roffi C, Caperna O, Miceli M, Ubaldi A, Battisti A, Scaramozzino P (2012). "[Beta-hexachlorocyclohexane contamination in dairy farms of the Sacco River Valley, Latium, Italy, 2005. A retrospective cohort study]". Epidemiol Prev (in Italian). 36 (5 Suppl 4): 34–43. PMID 23139187.
  5. ^ "Valle del Sacco: a poisoned land". 28 December 2012.

External links edit

  • beta-Hexachlorocyclohexane (beta-HCH) - Integrated Risk Information System – US EPA
  • Cyclohexane, 1,2,3,4,5,6-hexachloro-, (1α,2β,3α,4β,5α,6β)- – NIST

hexachlorocyclohexane, organochloride, which, isomers, hexachlorocyclohexane, byproduct, production, insecticide, lindane, typically, constitutes, technical, grade, lindane, though, been, produced, used, united, states, since, 1985, 2009, stockholm, convention. b Hexachlorocyclohexane b HCH is an organochloride which is one of the isomers of hexachlorocyclohexane HCH 1 It is a byproduct of the production of the insecticide lindane g HCH It is typically constitutes 5 14 of technical grade lindane 2 though it has not been produced or used in the United States since 1985 1 As of 2009 the Stockholm Convention on Persistent Organic Pollutants classified a hexachlorocyclohexane and b HCH as persistent organic pollutants POPs due to the chemical s ability to persist in the environment bioaccumulative biomagnifying and long range transport capacity b Hexachlorocyclohexane Names Preferred IUPAC name 1r 2r 3r 4r 5r 6r 1 2 3 4 5 6 Hexachlorocyclohexane Other names b HCHb Benzenehexachlorideb BHC Identifiers CAS Number 319 85 7 Y 3D model JSmol Interactive image Beilstein Reference 1907338 ChEBI CHEBI 28428 Y ChEMBL ChEMBL389022 Y ChemSpider 10468512 Y ECHA InfoCard 100 005 703 EC Number 206 271 3 KEGG C06988 UNII YM80ODM9PD Y CompTox Dashboard EPA DTXSID7020685 InChI InChI 1S C6H6Cl6 c7 1 2 8 4 10 6 12 5 11 3 1 9 h1 6H t1 2 3 4 5 6 YKey JLYXXMFPNIAWKQ CDRYSYESSA N YInChI 1 C6H6Cl6 c7 1 2 8 4 10 6 12 5 11 3 1 9 h1 6H t1 2 3 4 5 6 Key JLYXXMFPNIAWKQ CDRYSYESBR SMILES Cl C H 1 C H Cl C H Cl C H Cl C H Cl C H 1Cl Properties Chemical formula C6H6Cl6 Molar mass 290 83 g mol Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references This pesticide was widely used during the 1960s and 1970s particularly on cotton plants Although banned as a pesticide more than 30 years ago traces of beta HCH can still be found in water and soil Animal studies show that organochlorine pesticides including beta HCH are neurotoxic cause oxidative stress and damage the brain s dopaminergic system Human studies show that exposure to beta HCH is linked to Parkinson s and Alzheimer s disease 3 b HCH was present in elevated levels in some patients as recently as 2009 It was manufactured by exhausting chlorination of benzene and for this reason was called erroneously b BHC This synonym still persists In March 2005 the Italian National Monitoring System on Chemical Residuals in Food of Animal Origin detected levels of the pesticide b HCH that were 20 times higher than the legal limit of 0 003 mg kg in bulk milk from a dairy farm in the Sacco River valley b HCH a lindane isomer and possible human carcinogen was subsequently found in milk from several neighboring farms A study was therefore undertaken to evaluate the extent and risk factors for contamination 4 5 See also edita HexachlorocyclohexaneReferences edit a b Toxicological Profile for Alpha Beta Gamma and Delta Hexachlorocyclohexane U S Department of Health and Human Services Agency for Toxic Substances and Disease Registry August 2005 beta hexachlorocyclohexane Beta HCH Archived July 20 2008 at the Wayback Machine Draft Risk Profile May 2007 Medscape Medical News Pesticide Exposure Linked to Parkinson s Alzheimer s Disease July 2009 Sala M Caminiti A Rombola P Volpe A Roffi C Caperna O Miceli M Ubaldi A Battisti A Scaramozzino P 2012 Beta hexachlorocyclohexane contamination in dairy farms of the Sacco River Valley Latium Italy 2005 A retrospective cohort study Epidemiol Prev in Italian 36 5 Suppl 4 34 43 PMID 23139187 Valle del Sacco a poisoned land 28 December 2012 External links editbeta Hexachlorocyclohexane beta HCH Integrated Risk Information System US EPA Cyclohexane 1 2 3 4 5 6 hexachloro 1a 2b 3a 4b 5a 6b NIST Retrieved from https en wikipedia org w index php title B Hexachlorocyclohexane amp oldid 1161214404, wikipedia, wiki, book, books, library,

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