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Dichlorodiphenyldichloroethylene: Difference between revisions

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{{Chembox {{Chembox
| verifiedrevid = 414419691 | verifiedrevid = 443635813
| ImageFile = p,p'-dichlorodiphenyldichloroethene.svg | ImageFile = p,p'-dichlorodiphenyldichloroethene.svg
| ImageSize = | ImageSize =
| ImageName = Dichlorodiphenyldichloroethylene | ImageName = Dichlorodiphenyldichloroethylene
| ImageFile1 = DDE-3D-balls.png | ImageFile1 = Dichlorodiphenyldichloroethylene-from-xtal-3D-bs-17.png
| ImageSize1 = | ImageSize1 =
| ImageName1 = Dichlorodiphenyldichloroethylene | ImageName1 = Dichlorodiphenyldichloroethylene
| PIN = 1,1′-(2,2-Dichloroethene-1,1-diyl)bis(4-chlorobenzene)
| IUPACName = 1,1-''bis''-(4-chlorophenyl)-2,2-dichloroethene
| OtherNames = Dichlorodiphenyldichloroethylene | OtherNames = {{ubl|Dichlorodiphenyldichloroethylene|1,1-Dichloro-2,2-bis(4-chlorophenyl)ethene}}
⚫ | Abbreviations = p,p'-DDE
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
⚫ | Abbreviations = p,p'-DDE
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2927 | ChemSpiderID = 2927
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| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 72-55-9 | CASNo = 72-55-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4M7FS82U08
| PubChem = 3035 | PubChem = 3035
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16598 | ChEBI = 16598
| SMILES = Clc2ccc(\C(=C(/Cl)Cl)c1ccc(Cl)cc1)cc2 | SMILES = Clc2ccc(\C(=C(/Cl)Cl)c1ccc(Cl)cc1)cc2
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| C=14 | H=8 | Cl=4
| Formula = C<sub>14</sub>H<sub>8</sub>Cl<sub>4</sub>
| MolarMass = 318.02 g/mol
| Appearance = | Appearance =
| Density = | Density =
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| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}} }}
}} }}
'''Dichlorodiphenyldichloroethylene''' ('''DDE''') is a ] formed by the loss of ] (]) from ], 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 ] 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 ]; thus, it is rarely excreted from the body, and concentrations tend to increase throughout life. The major exception is the excretion of DDE in ], 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==
'''Dichlorodiphenyldichloroethylene''' (1,1-''bis''-(4-chlorophenyl)-2,2-dichloroethene) is the full name of DDE. This compound is formed by the loss of ] (]) of ] (1,1-''bis''-(4-chlorophenyl)-2,2,2-trichloroethane), of which it is one of the more common breakdown products.<ref></ref> DDE is fat soluble which tends to build up in the fat of animals. Due to its stability in fat, DDE is rarely excreted from the body, and body levels tend to increase throughout life. The major exception is the excretion of DDE in breast milk, which delivers a substantial portion of the mother's DDE burden to the young animal or child.
DDE is created by dehydrohalogenation of DDT. The loss of HCl results in a ] on the central (previously quaternary) ] atoms.

] ]


==Toxicity==
DDE and its parent, DDT, are reproductive toxicants for certain birds species, and major reasons for the decline of the ],<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 }}</ref> ]<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> ], and ].<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></ref> ], ], and ] are more susceptible to eggshell thinning than chickens and ], and DDE appears to be more potent than DDT.<ref name="ATSDRc5">http://www.atsdr.cdc.gov/toxprofiles/tp35.html</ref> DDE has been shown to be toxic to rats at 79.6&nbsp;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 ],<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> ]<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> ], and ].<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> ], ], and ] are more susceptible to eggshell thinning than chickens and ], 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>
⚫ The biological mechanism for the thinning is not entirely known, but it is believed that p,p'-DDE impairs the shell gland's ability to excrete ] onto the developing egg.<ref name="ATSDRc5"/><ref>, U.S. Fish and Wildlife Service, April 1996, page 23</ref><ref></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 |format=PDF| title= Endocrine Disrupting Contaminants |accessdate=2007-02-02}}</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 Pharmacol Toxicol Endocrinol| 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&ndash;12 percent thinner than before DDT was first used.<ref></ref>


==Mechanism==
Some studies have indicated that DDE is an ]<ref></ref> and contributes to ], but more recent studies provide strong evidence that there is no relationship between DDE exposure and breast cancer.<ref></ref> What is more clear is that DDE is a weak antiandrogen.<ref></ref>
⚫ The biological mechanism for the thinning is not entirely known, but it is believed that ]-DDE impairs the hen's gland's ability to excrete ] onto the developing egg.<ref name="ATSDRc5"/><ref> {{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&ndash;12 percent thinner than before DDT was first used.<ref> {{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 ]<ref> {{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 ], 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 ] ] 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>
Other studies found that exposure to DDE is linked to Alzheimer's and Parkinson's disease in humans.<ref name="medscape"></ref> Animal studies show that organochlorine pesticides—such as DDE—are neurotoxic, cause oxidative stress, and damage the brain's dopaminergic system.<ref name="medscape" />

==See also==
*]


==References== ==References==
<references/> <references/>


{{Insecticides}}
<!--==External links==-->
{{Androgen receptor modulators}}

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