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{{Chembox
| verifiedrevid = 443635813
| ImageFile = p,p'-dichlorodiphenyldichloroethene.svg
| ImageSize =
| ImageName = Dichlorodiphenyldichloroethylene
| ImageFile1 = Dichlorodiphenyldichloroethylene-from-xtal-3D-bs-17.png
| ImageSize1 =
| ImageName1 = Dichlorodiphenyldichloroethylene
| PIN = 1,1′-(2,2-Dichloroethene-1,1-diyl)bis(4-chlorobenzene)
| OtherNames = {{ubl|Dichlorodiphenyldichloroethylene|1,1-Dichloro-2,2-bis(4-chlorophenyl)ethene}}
| Section1 = {{Chembox Identifiers
| Abbreviations = p,p'-DDE
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2927
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C04596
| InChI = 1/C14H8Cl4/c15-11-5-1-9(2-6-11)13(14(17)18)10-3-7-12(16)8-4-10/h1-8H
| InChIKey = UCNVFOCBFJOQAL-UHFFFAOYAE
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 363207
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C14H8Cl4/c15-11-5-1-9(2-6-11)13(14(17)18)10-3-7-12(16)8-4-10/h1-8H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UCNVFOCBFJOQAL-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 72-55-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4M7FS82U08
| PubChem = 3035
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16598
| SMILES = Clc2ccc(\C(=C(/Cl)Cl)c1ccc(Cl)cc1)cc2
}}
| Section2 = {{Chembox Properties
| C=14 | H=8 | Cl=4
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
'''Dichlorodiphenyldichloroethylene''' ('''DDE''') is a [[chemical compound]] formed by the loss of [[hydrogen chloride]] ([[dehydrohalogenation]]) from [[DDT]], of which it is one of the more common breakdown products.<ref>{{Cite web |url=https://wwwn.cdc.gov/TSP/PHS/PHSLanding.aspx?id=79&tid=20 |title=ATSDR – Public Health Statement: DDT, DDE, and DDD<!-- Bot generated title --> |access-date=2023-12-29 |archive-date=2023-12-15 |archive-url=https://web.archive.org/web/20231215103554/https://wwwn.cdc.gov/TSP/PHS/PHSLanding.aspx?id=79&tid=20 |url-status=live }}</ref> Due to DDT's massive prevalence in society and [[agriculture]] during the mid 20th century, DDT and DDE are still widely seen in animal tissue samples.<ref>{{cite journal|doi=10.1021/jf60040a006 | volume=2 | issue=20 | title=Pesticide Residues in Foods, Dichlorodiphenyltrichloroethane and Dichlorodiphenyldichloroethylene Content in Prepared Foods | year=1954 | journal=Journal of Agricultural and Food Chemistry | pages=1034–1037 | last1 = Walker | first1 = K. C. | last2 = Goette | first2 = M. B. | last3 = Batchelor | first3 = G. S.| bibcode=1954JAFC....2.1034W }}</ref> DDE is particularly dangerous because it is fat-soluble like other [[organochlorines]]; thus, it is rarely excreted from the body, and concentrations tend to increase throughout life. The major exception is the excretion of DDE in [[breast milk]], which transfers a substantial portion of the mother's DDE burden to the young animal or child.<ref>{{cite journal | pmid = 19551328 | doi=10.1007/s00128-009-9796-3 | volume=83 | issue=6 | title=Breast milk excretion Kinetic of b-HCH, pp'DDE and pp'DDT | journal=Bull Environ Contam Toxicol | pages=869–73 | last1 = Waliszewski | first1 = SM | last2 = Melo-Santiesteban | first2 = G | last3 = Villalobos-Pietrini | first3 = R | last4 = Gómez-Arroyo | first4 = S | last5 = Amador-Muñoz | first5 = O | last6 = Herrero-Mercado | first6 = M | last7 = Carvajal | first7 = O | year=2009| bibcode=2009BuECT..83..869W | s2cid=24374271 }}</ref> Along with accumulation over an organism's lifetime, this stability leads to bioaccumulation in the environment, which amplifies DDE's negative effects.
==Synthesis==
DDE is created by dehydrohalogenation of DDT. The loss of HCl results in a [[double bond]] on the central (previously quaternary) [[carbon]] atoms.
[[File:Elimination DDT DDE.svg|thumb|upright=1.5|none|Degradation of DDT to form DDE by an elimination of HCl]]
==Toxicity==
DDE has been shown to be toxic to rats at 79.6 mg/kg.<ref>{{Cite web |url=https://www-s.nist.gov/srmors/msds/8467-MSDS.pdf?CFID=6441706&CFTOKEN=3aa7cf88111f43d5-7A960AA1-F2A1-B615-78A041930E2DD768 |title=NIST DDE MSDS |access-date=2015-04-30 |archive-date=2020-04-13 |archive-url=https://web.archive.org/web/20200413072628/https://www-s.nist.gov/srmors/msds/8467-MSDS.pdf?CFID=6441706&CFTOKEN=3aa7cf88111f43d5-7A960AA1-F2A1-B615-78A041930E2DD768 |url-status=dead }}</ref> DDE and its parent, DDT, are reproductive toxicants for certain birds species, and major reasons for the decline of the [[bald eagle]],<ref name="pmid17588911">{{cite journal |last1=Stokstad |first1=E |title=Species conservation. Can the bald eagle still soar after it is delisted? |journal=Science |volume=316 |issue=5832 |pages=1689–90 |year=2007 |pmid=17588911 |doi=10.1126/science.316.5832.1689 |s2cid=5051469 }}</ref> [[brown pelican]]<ref>"Endangered and Threatened Wildlife and Plants; 12-Month Petition Finding and Proposed Rule To Remove the Brown Pelican (Pelecanus occidentalis) From the Federal List of Endangered and Threatened Wildlife; Proposed Rule," Fish and Wildlife Service, U.S. Department of the Interior, February 20, 2008. {{USFR|73|9407}}</ref> [[peregrine falcon]], and [[osprey]].<ref name="ATSDRc5"/> These compounds cause egg shell thinning in susceptible species, which leads to the birds' crushing their eggs instead of incubating them, due to the latter's lack of resistance.<ref>{{Cite web |url=http://www.calacademy.org/calwild/1994spring/stories/falcons.htm |title=California Wild Spring 1994 – Peregrine Falcons<!-- Bot generated title --> |access-date=2007-03-21 |archive-url=https://archive.today/20070616194703/http://www.calacademy.org/calwild/1994spring/stories/falcons.htm |archive-date=2007-06-16 |url-status=dead }}</ref> [[Birds of prey]], [[waterfowl]], and [[passerine|song birds]] are more susceptible to eggshell thinning than chickens and [[Galliformes|related species]], and DDE appears to be more potent than DDT.<ref name="ATSDRc5">{{Cite web |url=https://www.atsdr.cdc.gov/toxprofiledocs/index.html?id=81&tid=20 |title=ATSDR - Toxicological Profile: DDT, DDE, DDD |access-date=2023-12-29 |archive-date=2023-12-27 |archive-url=https://web.archive.org/web/20231227210720/https://www.atsdr.cdc.gov/toxprofiledocs/index.html?id=81&tid=20 |url-status=live }}</ref>
Research shows that an elevated blood levels of DDEs (also of other toxic molecule from nonstick cookware, and fire retardants) have been tied to an increased risk for celiac disease in young people.<ref>{{Cite web|url=https://medicalxpress.com/news/2020-05-celiac-disease-linked-common-chemical.html|title=Celiac disease linked to common chemical pollutants|access-date=2020-05-13|archive-date=2020-05-12|archive-url=https://web.archive.org/web/20200512115956/https://medicalxpress.com/news/2020-05-celiac-disease-linked-common-chemical.html|url-status=live}}</ref> DDE has also been shown to be present in increased concentrations in the tumors of patients with primary hyperparathyroidism.<ref>{{Cite journal|last1=Hu|first1=Xin|last2=Saunders|first2=Neil|last3=Safley|first3=Susan|last4=Smith|first4=Matthew Ryan|last5=Liang|first5=Yongliang|last6=Tran|first6=ViLinh|last7=Sharma|first7=Joe|last8=Jones|first8=Dean P.|last9=Weber|first9=Collin J.|date=2021-01-01|title=Environmental chemicals and metabolic disruption in primary and secondary human parathyroid tumors|journal=Surgery|language=en|volume=169|issue=1|pages=102–108|doi=10.1016/j.surg.2020.06.010|pmid=32771296|pmc=7845795|issn=0039-6060}}</ref>
==Mechanism==
The biological mechanism for the thinning is not entirely known, but it is believed that [[Arene substitution pattern|p,p']]-DDE impairs the hen's gland's ability to excrete [[calcium carbonate]] onto the developing egg.<ref name="ATSDRc5"/><ref>[http://ecos.fws.gov/docs/recovery_plans/1996/960425.pdf Recovery Plan for the California Condor] {{Webarchive|url=https://web.archive.org/web/20061207055131/http://ecos.fws.gov/docs/recovery_plans/1996/960425.pdf |date=2006-12-07 }}, U.S. Fish and Wildlife Service, April 1996, page 23</ref><ref>{{Cite web |url=http://www.ec.gc.ca/soer-ree/English/Indicators/Issues/Toxic/Graphs/tx_s03_e.gif |title=DDE concentration and percent eggshell thinning in Double-crested Conmorant eggs(North Channel, Lake Huron, Ont.) |access-date=2009-04-15 |archive-url=https://web.archive.org/web/20070628141601/http://www.ec.gc.ca/soer-ree/English/Indicators/Issues/Toxic/Graphs/tx_s03_e.gif |archive-date=2007-06-28 |url-status=dead }}</ref><ref name="Guillette, 2006">{{cite web|last=Guillette| first=Louis J. Jr. |year=2006|url=http://www.ehponline.org/members/2005/8045/8045.pdf|title=Endocrine Disrupting Contaminants|access-date=2007-02-02|url-status=dead|archive-url=https://web.archive.org/web/20090325085455/http://www.ehponline.org/members/2005/8045/8045.pdf|archive-date=2009-03-25}}</ref><ref name="Lundholm, 1997">{{cite journal| last=Lundholm| first=C.E.| year=1997| title= DDE-Induced eggshell thinning in birds| journal=Comp Biochem Physiol C| issue= 2| doi= 10.1016/S0742-8413(97)00105-9| volume= 118| pages= 113–28| pmid=9490182}}</ref> Multiple mechanisms may be at work, or different mechanisms may operate in different species.<ref name="ATSDRc5"/> Some studies have shown that although DDE levels have fallen dramatically, eggshell thickness remains 10–12 percent thinner than before DDT was first used.<ref>[http://www.fws.gov/contaminants/examples/AlaskaPeregrine.cfm Division of Environmental Quality] {{webarchive|url=https://web.archive.org/web/20080303174350/http://www.fws.gov/contaminants/examples/AlaskaPeregrine.cfm |date=2008-03-03 }}</ref>
Some studies have indicated that DDE is an [[endocrine disruptor]]<ref>[http://www.breastcancerfund.org/site/pp.asp?c=kwKXLdPaE&b=84567 Chemical fact sheet: Organochlorine – The Breast Cancer Fund<!-- Bot generated title -->] {{webarchive|url=https://web.archive.org/web/20061009104100/http://www.breastcancerfund.org/site/pp.asp?c=kwKXLdPaE&b=84567 |date=2006-10-09 }}</ref> and contributes to [[breast cancer]], but more recent studies provide strong evidence that there is no relationship between DDE exposure and breast cancer.<ref>{{Cite web |url=http://extoxnet.orst.edu/faqs/pesticide/endocrine.htm |title=Questions about Endocrine Disruptors<!-- Bot generated title --> |access-date=2007-03-23 |archive-date=2007-04-04 |archive-url=https://web.archive.org/web/20070404202450/http://extoxnet.orst.edu/faqs/pesticide/endocrine.htm |url-status=live }}</ref> What is more clear is that DDE is a weak [[androgen receptor]] [[receptor antagonist|antagonist]] and can produce male genital tract abnormalities.<ref>{{cite journal | doi = 10.1093/aje/kwk109 | title = In utero exposure to the antiandrogen 1,1-dichloro-2,2-bis(p-chlorophenyl)ethylene (DDE) in relation to anogenital distance in male newborns from Chiapas, México | year = 2007 | last1 = Longnecker | first1 = M. P. | last2 = Gladen | first2 = B. C.|author2-link= Beth Gladen | last3 = Cupul-Uicab | first3 = L. A. | last4 = Romano-Riquer | first4 = S. P. | last5 = Weber | first5 = J.-P. | last6 = Chapin | first6 = R. E. | last7 = Hernandez-Avila | first7 = M. | journal = American Journal of Epidemiology | volume = 165 | issue = 9 | pages = 1015–22 | pmid = 17272288 | pmc = 1852527}}</ref>
==See also==
*[[Insecticide]]
==References==
<references/>
{{Insecticides}}
{{Androgen receptor modulators}}
[[Category:4-Chlorophenyl compounds]]
[[Category:Endocrine disruptors]]
[[Category:Nonsteroidal antiandrogens]]
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