Dichlorodiphenyldichloroethylene

Dichlorodiphenyldichloroethylene

Names
IUPAC name 1,1-bis-(4-chlorophenyl)-2,2-dichloroethene
Other names Dichlorodiphenyldichloroethylene
Identifiers
CAS Number	72-55-9 Y
3D model (Jmol)	Interactive image
Abbreviations	p,p'-DDE
ChEBI	CHEBI:16598 Y
ChemSpider	2927 Y
ECHA InfoCard	100.000.713
KEGG	C04596 Y
PubChem CID	3035
InChI 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 Y Key: UCNVFOCBFJOQAL-UHFFFAOYSA-N Y 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
SMILES Clc2ccc(\C(=C(/Cl)Cl)c1ccc(Cl)cc1)cc2
Properties
Chemical formula	C14H8Cl4
Molar mass	318.02 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

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. 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. 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 delivers a substantial portion of the mother's DDE burden to the young animal or child. Along with accumulation over an organism's life, this stability leads to bioaccumulation in the environment which amplifies DDE’s negative effects.

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

DDE has been shown to be toxic to rats at 79.6 mg/kg. DDE and its parent, DDT, are reproductive toxicants for certain birds species, and major reasons for the decline of the bald eagle,brown pelicanperegrine falcon, and osprey. 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.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.

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 calcium carbonate onto the developing egg. Multiple mechanisms may be at work, or different mechanisms may operate in different species. Some studies have shown that although DDE levels have fallen dramatically, eggshell thickness remains 10–12 percent thinner than before DDT was first used.