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Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-de badge-Q70894304 mw-list-item" title=""><a href="https://de.wikipedia.org/wiki/%CE%92-Hexachlorcyclohexan" title="Β-Hexachlorcyclohexan – German" lang="de" hreflang="de" data-title="Β-Hexachlorcyclohexan" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Beta-hexakloroziklohexano" title="Beta-hexakloroziklohexano – Basque" lang="eu" hreflang="eu" data-title="Beta-hexakloroziklohexano" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A8%D8%AA%D8%A7-%D9%87%DA%AF%D8%B2%D8%A7%DA%A9%D9%84%D8%B1%D9%88%D8%B3%DB%8C%DA%A9%D9%84%D9%88%D9%87%DA%AF%D8%B2%D8%A7%D9%86" title="بتا-هگزاکلروسیکلوهگزان – Persian" lang="fa" hreflang="fa" data-title="بتا-هگزاکلروسیکلوهگزان" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/%CE%92-esaclorocicloesano" title="Β-esaclorocicloesano – Italian" lang="it" hreflang="it" data-title="Β-esaclorocicloesano" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/%CE%92-Heksaklorosikloheksana" title="Β-Heksaklorosikloheksana – Malay" lang="ms" hreflang="ms" data-title="Β-Heksaklorosikloheksana" 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class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"><span class="mw-redirectedfrom">(Redirected from <a href="/w/index.php?title=Beta-Hexachlorocyclohexane&redirect=no" class="mw-redirect" title="Beta-Hexachlorocyclohexane">Beta-Hexachlorocyclohexane</a>)</span></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>β-Hexachlorocyclohexane </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Beta-hexachlorocyclohexane.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2f/Beta-hexachlorocyclohexane.svg/150px-Beta-hexachlorocyclohexane.svg.png" decoding="async" width="150" height="154" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2f/Beta-hexachlorocyclohexane.svg/225px-Beta-hexachlorocyclohexane.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2f/Beta-hexachlorocyclohexane.svg/300px-Beta-hexachlorocyclohexane.svg.png 2x" data-file-width="220" data-file-height="226" /></a><figcaption></figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Beta-Hexachlorocyclohexane_molecule_ball.png" class="mw-file-description"><img alt="Ball-and-stick model of the beta-hexachlorocyclohexane molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Beta-Hexachlorocyclohexane_molecule_ball.png/170px-Beta-Hexachlorocyclohexane_molecule_ball.png" decoding="async" width="170" height="180" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Beta-Hexachlorocyclohexane_molecule_ball.png/255px-Beta-Hexachlorocyclohexane_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Beta-Hexachlorocyclohexane_molecule_ball.png/340px-Beta-Hexachlorocyclohexane_molecule_ball.png 2x" data-file-width="1894" data-file-height="2000" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">(1<i>r</i>,2<i>r</i>,3<i>r</i>,4<i>r</i>,5<i>r</i>,6<i>r</i>)-1,2,3,4,5,6-Hexachlorocyclohexane</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">β-HCH<br />β-Benzenehexachloride<br />β-BHC</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=319-85-7">319-85-7</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=Cl%5BC%40H%5D1%5BC%40H%5D%28Cl%29%5BC%40%40H%5D%28Cl%29%5BC%40H%5D%28Cl%29%5BC%40%40H%5D%28Cl%29%5BC%40%40H%5D1Cl">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>1907338 </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=28428">CHEBI:28428</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL389022">ChEMBL389022</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.10468512.html">10468512</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.005.703">100.005.703</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q6445839#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>206-271-3</li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C06988">C06988</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/YM80ODM9PD">YM80ODM9PD</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID7020685">DTXSID7020685</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q6445839#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3+,4+,5-,6-<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: JLYXXMFPNIAWKQ-CDRYSYESSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3+,4+,5-,6-</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: JLYXXMFPNIAWKQ-CDRYSYESBR</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@H](Cl)[C@@H](Cl)[C@@H]1Cl</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td>C<sub>6</sub>H<sub>6</sub>Cl<sub>6</sub>  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>290.83 g/mol    </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=459977188&page2=%CE%92-Hexachlorocyclohexane">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>β-Hexachlorocyclohexane</b> (<b>β-HCH</b>) is an <a href="/wiki/Organochloride" class="mw-redirect" title="Organochloride">organochloride</a> which is one of the isomers of <a href="/wiki/Hexachlorocyclohexane" title="Hexachlorocyclohexane">hexachlorocyclohexane</a> (HCH).<sup id="cite_ref-CDC_1-0" class="reference"><a href="#cite_note-CDC-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> It is a byproduct of the production of the <a href="/wiki/Insecticide" title="Insecticide">insecticide</a> <a href="/wiki/Lindane" title="Lindane">lindane</a> (γ-HCH). It is typically constitutes 5–14% of <a href="/wiki/Chemical_purity" title="Chemical purity">technical-grade</a> lindane,<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> though it has not been produced or used in the United States since 1985.<sup id="cite_ref-CDC_1-1" class="reference"><a href="#cite_note-CDC-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> As of 2009, the <a href="/wiki/Stockholm_Convention_on_Persistent_Organic_Pollutants" title="Stockholm Convention on Persistent Organic Pollutants">Stockholm Convention on Persistent Organic Pollutants</a> classified α-hexachlorocyclohexane and β-HCH as <a href="/wiki/Persistent_organic_pollutant" title="Persistent organic pollutant">persistent organic pollutants (POPs)</a>, due to the chemical's ability to persist in the environment, <a href="/wiki/Bioaccumulation" title="Bioaccumulation">bioaccumulative</a>, <a href="/wiki/Biomagnification" title="Biomagnification">biomagnifying</a>, and long-range transport capacity. </p><p>This pesticide was widely used during the 1960s and 1970s, particularly on <a href="/wiki/Cotton_plant" class="mw-redirect" title="Cotton plant">cotton plants</a>. 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 <a href="/wiki/Neurotoxic" class="mw-redirect" title="Neurotoxic">neurotoxic</a>, cause <a href="/wiki/Oxidative_stress" title="Oxidative stress">oxidative stress</a>, and damage the brain's <a href="/wiki/Dopaminergic_system" class="mw-redirect" title="Dopaminergic system">dopaminergic system</a>. Human studies show that exposure to beta-HCH is linked to <a href="/wiki/Parkinson%27s" class="mw-redirect" title="Parkinson's">Parkinson's</a> and <a href="/wiki/Alzheimer%27s_disease" title="Alzheimer's disease">Alzheimer's disease</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> β-HCH was present in elevated levels in some patients as recently as 2009. It was manufactured by exhausting chlorination of <a href="/wiki/Benzene" title="Benzene">benzene</a> and for this reason was called erroneously β-BHC. This synonym still persists. </p><p>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 <a href="/wiki/Sacco_River" class="mw-redirect" title="Sacco River">Sacco River</a> valley. β-HCH, a lindane <a href="/wiki/Isomer" title="Isomer">isomer</a> and possible human <a href="/wiki/Carcinogen" title="Carcinogen">carcinogen</a>, was subsequently found in milk from several neighboring farms. A study was therefore undertaken to evaluate the extent and risk factors for contamination.<sup id="cite_ref-pmid23139187_4-0" class="reference"><a href="#cite_note-pmid23139187-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Hexachlorocyclohexane&action=edit&section=1" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Alpha-Hexachlorocyclohexane" class="mw-redirect" title="Alpha-Hexachlorocyclohexane">α-Hexachlorocyclohexane</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Hexachlorocyclohexane&action=edit&section=2" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-CDC-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-CDC_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-CDC_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://www.atsdr.cdc.gov/toxprofiles/tp43.pdf">Toxicological Profile for Alpha-, Beta-, Gamma-, and Delta-Hexachlorocyclohexane</a>, U.S. Department of Health and Human Services, Agency for Toxic Substances and Disease Registry, August 2005</span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.oztoxics.org/poprc/CandidatePOPs/beta%20hexachloro.pdf">beta-hexachlorocyclohexane (Beta HCH)</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20080720143144/http://www.oztoxics.org/poprc/CandidatePOPs/beta%20hexachloro.pdf">Archived</a> July 20, 2008, at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>, Draft Risk Profile, May 2007</span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.medscape.com/viewarticle/706374">Medscape Medical News</a>, Pesticide Exposure Linked to Parkinson's, Alzheimer's Disease, July 2009</span> </li> <li id="cite_note-pmid23139187-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid23139187_4-0">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFSalaCaminitiRombolàVolpe2012" class="citation journal cs1 cs1-prop-foreign-lang-source">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]". <i>Epidemiol Prev</i> (in Italian). <b>36</b> (5 Suppl 4): <span class="nowrap">34–</span>43. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23139187">23139187</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Epidemiol+Prev&rft.atitle=%5BBeta-hexachlorocyclohexane+contamination+in+dairy+farms+of+the+Sacco+River+Valley%2C+Latium%2C+Italy%2C+2005.+A+retrospective+cohort+study%5D&rft.volume=36&rft.issue=5+Suppl+4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E34-%3C%2Fspan%3E43&rft.date=2012&rft_id=info%3Apmid%2F23139187&rft.aulast=Sala&rft.aufirst=M&rft.au=Caminiti%2C+A&rft.au=Rombol%C3%A0%2C+P&rft.au=Volpe%2C+A&rft.au=Roffi%2C+C&rft.au=Caperna%2C+O&rft.au=Miceli%2C+M&rft.au=Ubaldi%2C+A&rft.au=Battisti%2C+A&rft.au=Scaramozzino%2C+P&rfr_id=info%3Asid%2Fen.wikipedia.org%3A%CE%92-Hexachlorocyclohexane" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.valledelsacco.eu/valle-del-sacco-a-poisoned-land/">"Valle del Sacco: a poisoned land"</a>. 28 December 2012.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Valle+del+Sacco%3A+a+poisoned+land&rft.date=2012-12-28&rft_id=http%3A%2F%2Fwww.valledelsacco.eu%2Fvalle-del-sacco-a-poisoned-land%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3A%CE%92-Hexachlorocyclohexane" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Hexachlorocyclohexane&action=edit&section=3" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://cfpub.epa.gov/ncea/iris2/chemicalLanding.cfm?substance_nmbr=244">beta-Hexachlorocyclohexane (beta-HCH) - Integrated Risk Information System</a> – <a href="/wiki/United_States_Environmental_Protection_Agency" title="United States Environmental Protection Agency">US EPA</a></li> <li><a rel="nofollow" class="external text" href="http://webbook.nist.gov/cgi/cbook.cgi?ID=319-85-7&Units=SI">Cyclohexane, 1,2,3,4,5,6-hexachloro-, (1α,2β,3α,4β,5α,6β)-</a> – <a href="/wiki/National_Institute_of_Standards_and_Technology" title="National Institute of Standards and Technology">NIST</a></li></ul>    </div><noscript><img src="https://auth.wikimedia.org/loginwiki/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=1" alt="" width="1" height="1" style="border: none; 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