A metabolite and degradation product of the pesticide DDT
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o,p'-DDE

Item No. 24235

Technical Information
Formal Name
1-chloro-2-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]-benzene
CAS Number
3424-82-6
Synonyms
  • 2,4’-DDE
  • o,p'-Dichlorodiphenyldichloroethylene
  • NSC 59908
Molecular Formula
C14H8Cl4
Formula Weight
Purity
≥95%
A solid
Chloroform: HeatedMethanol: Slightly soluble
SMILES
ClC1=CC=C(/C(C2=CC=CC=C2Cl)=C(Cl)\Cl)C=C1
InChi Code
InChI=1S/C14H8Cl4/c15-10-7-5-9(6-8-10)13(14(17)18)11-3-1-2-4-12(11)16/h1-8H
InChi Key
ZDYJWDIWLRZXDB-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    o,p'-DDE is a metabolite and degradation product of the organochlorine pesticide DDT.1 It accumulates in smallmouth buffalo, channel catfish, and largemouth bass as well as sediment in the Huntsville Spring Branch-Indian Creek tributary system surrounding a DDT manufacturing plant where it is considered a persistent organic pollutant (POP). o,p'-DDE inhibits estrogen binding to rainbow trout estrogen receptors (rtERs) with an IC50 value of 3.2 μM.2 It induces concentration-dependent secretion of estradiol by granulosa and theca cell co-cultures isolated from porcine ovarian follicles.3 In ovo exposure to o,p'-DDE increases degeneration of ovarian follicles and reduces testicular size in Japanese medaka (O. latipes).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Garrison, A.W., Cyterski, M., Roberts, K.D., et alOccurrences and fate of DDT principal isomers/metabolites, DDA, and o,p'-DDD enantiomers in fish, sediment and water at a DDT-impacted superfund site. Environ. Pollut. 194, 224-234 (2014).

    2. Matthews, J., Celius, T., Halgren, R., et alDifferential estrogen receptor binding of estrogenic substances: A species comparison. J. Steroid. Biochem. Mol. Biol. 74(4), 223-234 (2000).

    3. Wójtowicz, A.K., Gregoraszczuk, E.L., Ptak, A., et alEffect of single and repeated in vitro exposure of ovarian follicles to o,p'-DDT and p,p'-DDT and their metabolites. Pol. J. Pharmacol. 56(4), 465-472 (2004).

    4. Papoulias, D.M., Villalobos, S.A., Meadows, J.N., D.B., et alIn ovo exposure to o,p -DDE affects sexual development but not sexual differentiation in Japanese medaka (Oryzias latipes). Environ. Health Perspect. 111(1), 29-32 (2003).