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{{lowercasetitle}}
{{DISPLAYTITLE:''beta''-Hexachlorocyclohexane}}
{{Chembox {{Chembox
| verifiedrevid = 443419986 | verifiedrevid = 459977188
| Name = ''β''-hexachlorocyclohexane | Name = β-Hexachlorocyclohexane
| ImageFile = beta-hexachlorocyclohexane.svg | ImageFile = beta-hexachlorocyclohexane.svg
| ImageSize = 150px | ImageSize = 150px
| ImageFile1 = Beta-Hexachlorocyclohexane molecule ball.png
| IUPACName = β-1,2,3,4,5,6-hexachlorocyclohexane
| ImageSize1 = 170
⚫ | OtherNames = &beta;-HCH<br />&beta;-Benzenehexachloride<br>&beta;-BHC
| ImageAlt1 = Ball-and-stick model of the beta-hexachlorocyclohexane molecule
⚫ | Section1 = {{Chembox Identifiers
| PIN = (1''r'',2''r'',3''r'',4''r'',5''r'',6''r'')-1,2,3,4,5,6-Hexachlorocyclohexane
⚫ | OtherNames = β-HCH<br />β-Benzenehexachloride<br>β-BHC
⚫ |Section1={{Chembox Identifiers
| InChI = 1/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3+,4+,5-,6- | InChI = 1/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3+,4+,5-,6-
| InChIKey = JLYXXMFPNIAWKQ-CDRYSYESBR | InChIKey = JLYXXMFPNIAWKQ-CDRYSYESBR
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| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 319-85-7 | CASNo = 319-85-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = YM80ODM9PD
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10468512 | ChemSpiderID = 10468512
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 389022 | ChEMBL = 389022
| EINECS = 206-271-3
| PubChem = | PubChem =
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28428 | ChEBI = 28428
| Beilstein = 1907338
| KEGG = C06988
| SMILES = Cl1(Cl)(Cl)(Cl)(Cl)1Cl | SMILES = Cl1(Cl)(Cl)(Cl)(Cl)1Cl
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>6</sub>H<sub>6</sub>Cl<sub>6</sub> | Formula = C<sub>6</sub>H<sub>6</sub>Cl<sub>6</sub>
| MolarMass = 290.83 g/mol | MolarMass = 290.83 g/mol
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| BoilingPt = | BoilingPt =
| Solubility = }} | Solubility = }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = }} | AutoignitionPt = }}
}} }}


'''β-hexachlorocyclohexane''' (β-HCH) is an ] which is one of the isomers of hexachlorocyclohexane (HCH).<ref name="CDC">, U.S. Department of Health and Human Services, Agency for Toxic Substances and Disease Registry, August 2005</ref> It is a byproduct of the production of the ] ] (γ-HCH). It is typically constitutes 5-14% of technical grade lindane,<ref>, Draft Risk Profile, May 2007</ref> though it has not been produced or used in the United States for more than 20 years.<ref name="CDC"/> '''β-Hexachlorocyclohexane''' ('''β-HCH''') is an ] which is one of the isomers of ] (HCH).<ref name="CDC">, U.S. Department of Health and Human Services, Agency for Toxic Substances and Disease Registry, August 2005</ref> It is a byproduct of the production of the ] ] (γ-HCH). It is typically constitutes 5–14% of ] lindane,<ref> {{webarchive |url=https://web.archive.org/web/20080720143144/http://www.oztoxics.org/poprc/CandidatePOPs/beta%20hexachloro.pdf |date=July 20, 2008 }}, Draft Risk Profile, May 2007</ref> though it has not been produced or used in the United States since 1985.<ref name="CDC"/> As of 2009, the ] classified α-hexachlorocyclohexane and β-HCH as ], due to the chemical's ability to persist in the environment, ], ], and long-range transport capacity.


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 <ref>, Pesticide Exposure Linked to Parkinson's, Alzheimer's Disease, July 2009</ref>. Beta-HCH was present in elevated levels in some patients as recently as 2009. This pesticide was widely used during the 1960s and 1970s, particularly on ]s. 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 ], cause ], and damage the brain's ]. Human studies show that exposure to beta-HCH is linked to ] and ].<ref>, Pesticide Exposure Linked to Parkinson's, Alzheimer's Disease, July 2009</ref> β-HCH was present in elevated levels in some patients as recently as 2009.
It was manufactured by exhausting chlorination of ] 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&nbsp;mg/kg in bulk milk from a dairy farm in the ] valley. β-HCH, a lindane ] and possible human ], was subsequently found in milk from several neighboring farms. A study was therefore undertaken to evaluate the extent and risk factors for contamination.<ref name="pmid23139187">{{cite journal | vauthors = Sala M, Caminiti A, Rombolà P, Volpe A, Roffi C, Caperna O, Miceli M, Ubaldi A, Battisti A, Scaramozzino P | title = | language = it | journal = Epidemiol Prev | volume = 36 | issue = 5 Suppl 4 | pages = 34–43 | date = 2012 | pmid = 23139187 }}</ref><ref>{{cite web |url=http://www.valledelsacco.eu/valle-del-sacco-a-poisoned-land/ |title= Valle del Sacco: a poisoned land|author=<!--Not stated--> |date= 28 December 2012}}</ref>


==See also== ==See also==
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==External links== ==External links==
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{{DEFAULTSORT:Hexachlorocyclohexane, Beta-}} {{DEFAULTSORT:Hexachlorocyclohexane, Beta-}}
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