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'''β-hexachlorocyclohexane''' (β-HCH) is an [[organochloride]] which is one of the isomers of hexachlorocyclohexane (HCH).<ref name="CDC">[http://www.atsdr.cdc.gov/toxprofiles/tp43.pdf 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</ref> It is a byproduct of the production of the [[insecticide]] [[lindane]] (γ-HCH). It is typically constitutes 5-14% of technical grade lindane,<ref>[http://www.oztoxics.org/poprc/CandidatePOPs/beta%20hexachloro.pdf beta-hexachlorocyclohexane (Beta HCH)], Draft Risk Profile, May 2007</ref> though it has not been produced or used in the United States for more than 20 years, i.e. since 1985.<ref name="CDC"/> As of 2011, the [[Stockholm Convention on Persistent Organic Pollutants]] classified (&alpha;-HCH) and (β-HCH) as [[Persistent organic pollutant|Persistent organic pollutants (POPs)]], due to to the chemical's ability to persistence in the environment, bioaccumulative, biomagnifying, and long-range transport capacity.
'''β-hexachlorocyclohexane''' (β-HCH) is an [[organochloride]] which is one of the isomers of hexachlorocyclohexane (HCH).<ref name="CDC">[http://www.atsdr.cdc.gov/toxprofiles/tp43.pdf 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</ref> It is a byproduct of the production of the [[insecticide]] [[lindane]] (γ-HCH). It is typically constitutes 5-14% of technical grade lindane,<ref>[http://www.oztoxics.org/poprc/CandidatePOPs/beta%20hexachloro.pdf beta-hexachlorocyclohexane (Beta HCH)], Draft Risk Profile, May 2007</ref> though it has not been produced or used in the United States for more than 20 years, i.e. since 1985.<ref name="CDC"/> As of 2009, the [[Stockholm Convention on Persistent Organic Pollutants]] classified (&alpha;-HCH) and (β-HCH) as [[Persistent organic pollutant|Persistent organic pollutants (POPs)]], due to to the chemical's ability to persistence in the environment, bioaccumulative, biomagnifying, 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>[http://www.medscape.com/viewarticle/706374 Medscape Medical News], 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 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>[http://www.medscape.com/viewarticle/706374 Medscape Medical News], 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.

Revision as of 20:53, 30 April 2014

β-hexachlorocyclohexane
Names
IUPAC name
β-1,2,3,4,5,6-hexachlorocyclohexane
Other names
β-HCH
β-Benzenehexachloride
β-BHC
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.703 Edit this at Wikidata
  • InChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3+,4+,5-,6- checkY
    Key: JLYXXMFPNIAWKQ-CDRYSYESSA-N checkY
  • 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).
checkY verify (what is checkY☒N ?)

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 for more than 20 years, i.e. since 1985.[1] As of 2009, the Stockholm Convention on Persistent Organic Pollutants classified (α-HCH) and (β-HCH) as Persistent organic pollutants (POPs), due to to the chemical's ability to persistence in the environment, bioaccumulative, biomagnifying, 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.[3] Beta-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 beta-BHC. This synnonym still persists.

In March 2005, the Italian National Monitoring System on Chemical Residuals in Food of Animal Origin detected levels of the pesticide beta-hexachlorocyclohexane (ß-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. ß-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

References

  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), Draft Risk Profile, May 2007
  3. ^ Medscape Medical News, Pesticide Exposure Linked to Parkinson's, Alzheimer's Disease, July 2009
  4. ^ [1], Beta-hexachlorocyclohexane contamination in dairy farms of the Sacco River Valley, Latium, Italy, 2005. A retrospective cohort study
  5. ^ [2], Valle del Sacco: a poisoned land

External links