4,4'-DDE

Chemical properties

white crystalline powder

The Uses of 4,4'-DDE

Military product; chemical research. Degradation product of p,p′-DDT.

The Uses of 4,4'-DDE

1,1-Dichloro-2,2-bis(4-chlorophenyl)ethane(DDE) has been used to study the ability of Pseudomonas acidovorans M3GY to transform DDE and its unchlorinated analog, 1,1-diphenylethylene (DPE).It has been used to investigate the role of incubation time, solvent type, yeast inoculum growth stage and concentration on the results of yeast assay for estrogenic compounds.

What are the applications of Application

1,1-Dichloro-2,2-bis(4-chlorophenyl)ethene is a potent androgen receptor antagonist

Definition

ChEBI: A chlorophenylethylene that is ethylene substituted by two 4-chlorophenyl groups at position 1 and two chlorine atoms at position 2.

General Description

White crystalline solid or white powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

4,4'-DDE is sensitive to exposure to light. 4,4'-DDE is incompatible with strong oxidizing agents and strong bases. Oxidation is catalyzed by UV radiation.

Health Hazard

A derivative of DDT; structurally and toxicproperties are similar to those of DDT;however, the acute effects are somewhatmilder; moderately toxic by ingestion; ateratogenic substance; adequate evidence ofcarcinogenicity in experimental animals
LD50 oral (rat): 880 mg/kg
LD50 oral (mouse): 700 mg/kg.

Fire Hazard

Flash point data for 4,4'-DDE are not available. 4,4'-DDE is probably combustible.

Safety Profile

Suspected carcinogen withexperimental carcinogenic and neoplastigenic data. Poisonby ingestion. Experimental reproductive effects. Mutationdata reported. An insecticide. When heated todecomposition it emits very toxic fumes of Cl-.

Source

Agricultural runoff degradation of p,p′-DDT (quoted, Verschueren, 1983).

Environmental Fate

Biological. In four successive 7-day incubation periods, p,p′-DDE (5 and 10 mg/L) was recalcitrant to degradation in a settled domestic wastewater inoculum (Tabak et al.,1981).
Photolytic. When an aqueous solution of p,p′-DDE (0.004uM) in natural water samples collected from California and Hawaii was irradiated (maximum λ= 240 nm) for 120 hours, 62% was photooxidized to p,p′-dichlorobenzophenone (Ross and Crosby, 1985).
When p,p′-DDE in water was irradiated at 313 nm, a quantum yield of 0.3 was achieved. A photolysis half-life of 0.9 days in summer and 6.1 days in winter by direct sunlight at 40° latitude was observed. Photolysis products included DDMU (yield 20%), o-chl
When p,p′-DDE in a methanol solvent was photolyzed at 260 nm, a dichloro-benzophenone, a dichlorobiphenyl, DDMU and 3,6-dichlorofluorenone (yield 10%) formed as the major products (Plimmer et al., 1970). Chemical/Physical. May degrade to bis(chlorophenyl)acetic acid (DDA) and hydrochloric acid in water (Verschueren, 1983) or oxidize to p,p′-dichlorobenzophenone using UV light as a catalyst (U.S. Department of Health and Human Services, 1989).

Purification Methods

Crystallise DDE from MeOH or EtOH and dry it in vacuo. The purity is checked by TLC. [G.tzi & Stammbach Helv Chim Acta 28 569 1946, Beilstein 5 H 639, 5 III1891.] POSSIBLE CARCINOGEN.