Dichlorodiphenyldichloroethylene

Dichlorodiphenyldichloroethylene
Dichlorodiphenyldichloroethylene
Dichlorodiphenyldichloroethylene
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)
Abbreviations p,p'-DDE
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.713 Edit this at Wikidata
KEGG
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 checkY
    Key: UCNVFOCBFJOQAL-UHFFFAOYSA-N checkY
  • 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).
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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.

  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.

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