Dichlorodiphenyldichloroethylene

Last updated
Dichlorodiphenyldichloroethylene
P,p'-dichlorodiphenyldichloroethene.svg
Dichlorodiphenyldichloroethylene-from-xtal-3D-bs-17.png
Names
Preferred IUPAC name
1,1′-(2,2-Dichloroethene-1,1-diyl)bis(4-chlorobenzene)
Other names
  • Dichlorodiphenyldichloroethylene
  • 1,1-Dichloro-2,2-bis(4-chlorophenyl)ethene
Identifiers
3D model (JSmol)
Abbreviationsp,p'-DDE
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.713 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C14H8Cl4/c15-11-5-1-9(2-6-11)13(14(17)18)10-3-7-12(16)8-4-10/h1-8H Yes check.svgY
    Key: UCNVFOCBFJOQAL-UHFFFAOYSA-N Yes check.svgY
  • 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
    Key: UCNVFOCBFJOQAL-UHFFFAOYAE
  • Clc2ccc(\C(=C(/Cl)Cl)c1ccc(Cl)cc1)cc2
Properties
C14H8Cl4
Molar mass 318.02 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [1] 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. [2] 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. [3] Along with accumulation over an organism's lifetime, this stability leads to bioaccumulation in the environment, which amplifies DDE's negative effects.

Contents

Synthesis

DDE is created by dehydrohalogenation of DDT. The loss of HCl results in a double bond on the central (previously quaternary) carbon atoms.

Degradation of DDT to form DDE by an elimination of HCl Elimination DDT DDE.svg
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. [4] DDE and its parent, DDT, are reproductive toxicants for certain birds species, and major reasons for the decline of the bald eagle, [5] brown pelican [6] peregrine falcon, and osprey. [7] 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. [8] Birds of prey, waterfowl, and song birds are more susceptible to eggshell thinning than chickens and related species, and DDE appears to be more potent than DDT. [7]

A 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. [9] DDE has also been shown to be present in increased concentrations in the tumors of patients with primary hyperparathyroidism. [10]

Mechanism

The biological mechanism for the thinning is not entirely known, but it is believed that p,p'-DDE impairs the mother bird's glands ability to excrete calcium carbonate onto the developing egg. [7] [11] [12] [13] [14] Multiple mechanisms may be at work, or different mechanisms may operate in different species. [7] Some studies have shown that although DDE levels have fallen dramatically, eggshell thickness remains 1012 percent thinner than before DDT was first used. [15]

Some studies have indicated that DDE is an endocrine disruptor [16] and contributes to breast cancer, but more recent studies provide strong evidence that there is no relationship between DDE exposure and breast cancer. [17] What is more clear is that DDE is a weak androgen receptor antagonist and can produce male genital tract abnormalities. [18]

See also

Related Research Articles

<span class="mw-page-title-main">DDT</span> Organochloride known for its insecticidal properties

Dichlorodiphenyltrichloroethane, commonly known as DDT, is a colorless, tasteless, and almost odorless crystalline chemical compound, an organochloride. Originally developed as an insecticide, it became infamous for its environmental impacts. DDT was first synthesized in 1874 by the Austrian chemist Othmar Zeidler. DDT's insecticidal action was discovered by the Swiss chemist Paul Hermann Müller in 1939. DDT was used in the second half of World War II to limit the spread of the insect-borne diseases malaria and typhus among civilians and troops. Müller was awarded the Nobel Prize in Physiology or Medicine in 1948 "for his discovery of the high efficiency of DDT as a contact poison against several arthropods". The WHO's anti-malaria campaign of the 1950s and 1960s relied heavily on DDT and the results were promising, though there was a resurgence in developing countries afterwards.

<span class="mw-page-title-main">Insecticide</span> Pesticide used against insects

Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Insecticides are used in agriculture, medicine, industry and by consumers. Insecticides are claimed to be a major factor behind the increase in the 20th-century's agricultural productivity. Nearly all insecticides can significantly alter ecosystems; many are toxic to humans and/or animals; some become concentrated as they spread along the food chain.

<span class="mw-page-title-main">Peregrine falcon</span> Widely distributed bird of prey

The peregrine falcon, also known simply as the peregrine, and historically as the duck hawk in North America, is a cosmopolitan bird of prey (raptor) in the family Falconidae. A large, crow-sized falcon, it has a blue-grey back, barred white underparts, and a black head. The peregrine is renowned for its speed. It can reach over 320 km/h (200 mph) during its characteristic hunting stoop, making it the fastest member of the animal kingdom. According to a National Geographic TV program, the highest measured speed of a peregrine falcon is 389 km/h (242 mph). As is typical for bird-eating (avivore) raptors, peregrine falcons are sexually dimorphic, with females being considerably larger than males.

Chlordane, or chlordan, is an organochlorine compound that was used as a pesticide. It is a white solid. In the United States, chlordane was used for termite-treatment of approximately 30 million homes until it was banned in 1988. Chlordane was banned 10 years earlier for food crops like corn and citrus, and on lawns and domestic gardens.

<span class="mw-page-title-main">Dicofol</span> Chemical compound

Dicofol is an insecticide, an organochlorine that is chemically related to DDT. Dicofol is a miticide that is very effective against spider mite. Its production and use is banned internationally under the Stockholm Convention.

<span class="mw-page-title-main">Endocrine disruptor</span> Chemicals that can interfere with endocrine or hormonal systems

Endocrine disruptors, sometimes also referred to as hormonally active agents, endocrine disrupting chemicals, or endocrine disrupting compounds are chemicals that can interfere with endocrine systems. These disruptions can cause numerous adverse human health outcomes including, alterations in sperm quality and fertility, abnormalities in sex organs, endometriosis, early puberty, altered nervous system function, immune function, certain cancers, respiratory problems, metabolic issues, diabetes, obesity, cardiovascular problems, growth, neurological and learning disabilities, and more. Found in many household and industrial products, endocrine disruptors "interfere with the synthesis, secretion, transport, binding, action, or elimination of natural hormones in the body that are responsible for development, behavior, fertility, and maintenance of homeostasis ."

Organochlorine chemistry is concerned with the properties of organochlorine compounds, or organochlorides, organic compounds containing at least one covalently bonded atom of chlorine. The chloroalkane class includes common examples. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names, applications, and properties. Organochlorine compounds have wide use in many applications, though some are of profound environmental concern, with TCDD being one of the most notorious.

<span class="mw-page-title-main">Persistent organic pollutant</span> Organic compounds that are resistant to environmental degradation

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<span class="mw-page-title-main">Biomagnification</span> Process of progressive accumulation in food chain

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<span class="mw-page-title-main">Dieldrin</span> Chemical compound

Dieldrin is an organochlorine compound originally produced in 1948 by J. Hyman & Co, Denver, as an insecticide. Dieldrin is closely related to aldrin, which reacts further to form dieldrin. Aldrin is not toxic to insects; it is oxidized in the insect to form dieldrin which is the active compound. Both dieldrin and aldrin are named after the Diels-Alder reaction which is used to form aldrin from a mixture of norbornadiene and hexachlorocyclopentadiene.

Derek Almey Ratcliffe was one of the most significant British nature conservationists of the 20th century. He was Chief Scientist for the Nature Conservancy Council at the Monks Wood Experimental Station, Abbots Ripton, Huntingdon, retiring in 1989. Ratcliffe was the author of the 1977 Nature Conservation Review, a document which set out the most important sites for nature conservation in the United Kingdom. He also published various works on nature and conservation.

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<span class="mw-page-title-main">Aldrin</span> Chemical compound

Aldrin is an organochlorine insecticide that was widely used until the 1990s, when it was banned in most countries. Aldrin is a member of the so-called "classic organochlorines" (COC) group of pesticides. COCs enjoyed a very sharp rise in popularity during and after World War II. Other noteworthy examples of COCs include dieldrin and DDT. After research showed that organochlorines can be highly toxic to the ecosystem through bioaccumulation, most were banned from use. Before the ban, it was heavily used as a pesticide to treat seed and soil. Aldrin and related "cyclodiene" pesticides became notorious as persistent organic pollutants.

David Beaumont Peakall was an internationally recognised toxicologist. His research into the effects of DDE and DDT on eggshells contributed to the ban on DDT in the United States. He proved that the chemicals caused thinning of eggshells, leading to a reduction in the population of various bird species. He also pioneered research on the effects of PCBs on birds.

<span class="mw-page-title-main">Environmental toxicology</span>

Environmental toxicology is a multidisciplinary field of science concerned with the study of the harmful effects of various chemical, biological and physical agents on living organisms. Ecotoxicology is a subdiscipline of environmental toxicology concerned with studying the harmful effects of toxicants at the population and ecosystem levels.

<span class="mw-page-title-main">Environmental impact of pesticides</span> Environmental effect

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References

  1. ATSDR – Public Health Statement: DDT, DDE, and DDD
  2. Walker, K. C.; Goette, M. B.; Batchelor, G. S. (1954). "Pesticide Residues in Foods, Dichlorodiphenyltrichloroethane and Dichlorodiphenyldichloroethylene Content in Prepared Foods". Journal of Agricultural and Food Chemistry. 2 (20): 1034–1037. doi:10.1021/jf60040a006.
  3. Waliszewski, SM; Melo-Santiesteban, G; Villalobos-Pietrini, R; Gómez-Arroyo, S; Amador-Muñoz, O; Herrero-Mercado, M; Carvajal, O (2009). "Breast milk excretion Kinetic of b-HCH, pp'DDE and pp'DDT". Bull Environ Contam Toxicol. 83 (6): 869–73. doi:10.1007/s00128-009-9796-3. PMID   19551328. S2CID   24374271.
  4. NIST DDE MSDS
  5. Stokstad, E (2007). "Species conservation. Can the bald eagle still soar after it is delisted?". Science. 316 (5832): 1689–90. doi:10.1126/science.316.5832.1689. PMID   17588911. S2CID   5051469.
  6. "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. 73 FR 9407
  7. 1 2 3 4 ATSDR - Toxicological Profile: DDT, DDE, DDD
  8. "California Wild Spring 1994 – Peregrine Falcons". Archived from the original on 2007-06-16. Retrieved 2007-03-21.
  9. "Celiac disease linked to common chemical pollutants".
  10. Hu, Xin; Saunders, Neil; Safley, Susan; Smith, Matthew Ryan; Liang, Yongliang; Tran, ViLinh; Sharma, Joe; Jones, Dean P.; Weber, Collin J. (2021-01-01). "Environmental chemicals and metabolic disruption in primary and secondary human parathyroid tumors". Surgery. 169 (1): 102–108. doi:10.1016/j.surg.2020.06.010. ISSN   0039-6060. PMC   7845795 . PMID   32771296.
  11. Recovery Plan for the California Condor, U.S. Fish and Wildlife Service, April 1996, page 23
  12. "DDE concentration and percent eggshell thinning in Double-crested Conmorant eggs(North Channel, Lake Huron, Ont.)". Archived from the original on 2007-06-28. Retrieved 2009-04-15.
  13. Guillette, Louis J. Jr. (2006). "Endocrine Disrupting Contaminants" (PDF). Archived from the original (PDF) on 2009-03-25. Retrieved 2007-02-02.
  14. Lundholm, C.E. (1997). "DDE-Induced eggshell thinning in birds". Comp Biochem Physiol C. 118 (2): 113–28. doi:10.1016/S0742-8413(97)00105-9. PMID   9490182.
  15. Division of Environmental Quality Archived 2008-03-03 at the Wayback Machine
  16. Chemical fact sheet: Organochlorine – The Breast Cancer Fund Archived 2006-10-09 at the Wayback Machine
  17. Questions about Endocrine Disruptors
  18. Longnecker, M. P.; Gladen, B. C.; Cupul-Uicab, L. A.; Romano-Riquer, S. P.; Weber, J.-P.; Chapin, R. E.; Hernandez-Avila, M. (2007). "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". American Journal of Epidemiology. 165 (9): 1015–22. doi:10.1093/aje/kwk109. PMC   1852527 . PMID   17272288.