p,p'-DDE

Names

[ CAS No. ]:
72-55-9

[ Name ]:
p,p'-DDE

[Synonym ]:
Benzene, 1,1'-(dichloroethenylidene)bis[4-chloro-
DDE
p,p'-DDE
1,1-bis(4-chlorophenyl)-2,2-dichloroethylene
2,2-Bis(4-chlorophenyl)-1,1-dichloroethylene
dichlorodiphenyldichloroethylene
para,para'-DDE
EINECS 200-784-6
DDE, p,p'-
1,1'-(2,2-dichloroethene-1,1-diyl)bis(4-chlorobenzene)
Benzene, 1,1'-(2,2-dichloroethenylidene)bis[4-chloro-
MFCD00003284
p,p'-Dichlorodiphenyldichloroethylene
1,1'-(2,2-Dichloro-1,1-ethenediyl)bis(4-chlorobenzene)
1,1-Bis(p-chlorophenyl)-2,2-dichloroethylene

Biological Activity

[Description]:

p,p'-DDE (4,4'-DDE), a major metabolite of persistent dichlorodiphenyltrichloroethane (DDT), is a potent androgen receptor antagonist, with an IC50 of 5 μM and a Ki of 3.5 μM[1].

[Related Catalog]:

Research Areas >> Endocrinology

Signaling Pathways >> Others >> Androgen Receptor

[References]

[1]. Kelce WR, et al. Persistent DDT metabolite p,p'-DDE is a potent androgen receptor antagonist. Nature. 1995;375(6532):581-585.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
383.1±37.0 °C at 760 mmHg

[ Melting Point ]:
88-90 °C(lit.)

[ Molecular Formula ]:
C₁₄H₈Cl₄

[ Molecular Weight ]:
318.025

[ Flash Point ]:
183.7±23.9 °C

[ Exact Mass ]:
315.938019

[ LogP ]:
6.37

[ Vapour Pressure ]:
0.0±0.8 mmHg at 25°C

[ Index of Refraction ]:
1.622

[ Stability ]:
Stable, but light-sensitive. Incompatible with strong bases, strong oxidizing agents.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KV9450000

CHEMICAL NAME :: Ethylene, 1,1-dichloro-2,2-bis(p-chlorophenyl)-

CAS REGISTRY NUMBER :: 72-55-9

BEILSTEIN REFERENCE NO. :: 1913355

LAST UPDATED :: 199710

DATA ITEMS CITED :: 42

MOLECULAR FORMULA :: C14-H8-Cl4

MOLECULAR WEIGHT :: 318.02

WISWESSER LINE NOTATION :: GYGUYR DG&R DG

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 880 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 700 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 504 mg/kg/6W-C

TOXIC EFFECTS :: Liver - changes in liver weight Immunological Including Allergic - decrease in cellular immune response Immunological Including Allergic - decrease in humoral immune response

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - pigeon

DOSE/DURATION :: 586 mg/kg/28D-C

TOXIC EFFECTS :: Behavioral - food intake (animal) Liver - changes in liver weight Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - domestic

DOSE/DURATION :: 76160 ug/kg/8W-C

TOXIC EFFECTS :: Autonomic Nervous System - sympathomimetic Liver - changes in liver weight Biochemical - Neurotransmitters or modulators (putative) - dopamine at other sites

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 9700 mg/kg/78W-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 36 gm/kg/86W-C

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Liver - tumors Endocrine - adrenal cortex tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 28 gm/kg/80W-C

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Liver - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 17 gm/kg/78W-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 57 gm/kg/68W-C

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Liver - tumors Endocrine - adrenal cortex tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 41 gm/kg/97W-C

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Liver - tumors Endocrine - adrenal cortex tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 81 gm/kg/97W-C

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Liver - tumors Endocrine - adrenal cortex tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 3500 ug/kg

SEX/DURATION :: female 7 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TYPE OF TEST :: Mutation test systems - not otherwise specified

TYPE OF TEST :: DNA inhibition

MUTATION DATA

TYPE OF TEST :: Mutation in mammalian somatic cells

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 20 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 136,137,1984 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 5,83,1974 IARC Cancer Review:Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 53,179,1991 IARC Cancer Review:Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 53,179,1991 IARC Cancer Review:Group 2B IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 53,179,1991 TOXICOLOGY REVIEW RREVAH Residue Reviews. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1962- Volume(issue)/page/year: 48,141,1973

Safety Information

[ Symbol ]:

GHS02, GHS06, GHS08, GHS09

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H301 + H311 + H331-H370-H411

[ Precautionary Statements ]:
P210-P260-P273-P280-P301 + P310-P311

[ Personal Protective Equipment ]:
Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R22;R33

[ Safety Phrases ]:
36/37-60-61-45-16-7-62

[ RIDADR ]:
UN 3077 9/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
KV9450000

[ HS Code ]:
2903999090

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2903999090

[ Summary ]:
2903999090 halogenated derivatives of aromatic hydrocarbons VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

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