Supplier Related Products Identification Chemical Properties Safety Data Raw materials And Preparation Products Hazard Information Material Safety Data Sheet(MSDS) Spectrum Detail Well-known Reagent Company Product Information
WebSite >  CAS DataBase List  > 56-53-1

56-53-1

Supplier Related Products Identification Chemical Properties Safety Data Raw materials And Preparation Products Hazard Information Material Safety Data Sheet(MSDS) Spectrum Detail Well-known Reagent Company Product Information

Product Image

Identification

Name
Diethylstilbestrol
CAS
56-53-1
Synonyms
3,4-BIS(P-HYDROXYPHENYL)-3-HEXENE
4,4'-DIHYDROXY-ALPHA,BETA-DIETHYLSTILBENE
A,A'-DIETHYL-4,4'-STILBENEDIOL
ALPHA
ALPHA,ALPHA'-DIETHYL-(E)-4,4'-STILBENEDIOL
ALPHA-DIETHYLSTILBENEDIOL
DES
DIETHYLSTILBESTEROL
DIETHYLSTILBESTROL
DOMESTROL
ESTROSYN
FONATOL
GRAFESTROL
LABOTEST-BB LT00233101
OESTROGENINE
PALESTROL
SEXOCRETIN
STILBESTEROL
STILBESTROL
TRANS-DIETHYLSTILBESTROL
EINECS(EC#)
200-278-5
Molecular Formula
C18H20O2
MDL Number
MFCD00002373
Molecular Weight
268.35
MOL File
56-53-1.mol

Chemical Properties

Appearance
White Solid
Melting point 
170-172 °C(lit.)

mp 
170-172 °C(lit.)

Boiling point 
351.51°C (rough estimate)
density 
1.1096 (rough estimate)
refractive index 
1.4800 (estimate)
storage temp. 
0-6°C
solubility 
methanol: 0.1 g/mL, clear, faintly yellow

pka
pKa 9.02(H2O t=25 I=0.025) (Uncertain)
form 
Crystalline Powder
color 
White to almost white
Water Solubility 
PRACTICALLY INSOLUBLE
Usage
A synthetic, nonsteroidal estrogen. Recomended solvents are DMSO, DMF and ethanol, even in these solvents do not store in solution for any prolonged period of time.
Merck 
13,3155
BRN 
2056095
Stability:
Isomerizes rapidly in Benzene, Chloroform, and Ether. Keep Shielded from light.
CAS DataBase Reference
56-53-1(CAS DataBase Reference)
NIST Chemistry Reference
Diethylstilbesterol(56-53-1)
IARC
1 (Vol. 21, Sup 7, 100A) 2012
EPA Substance Registry System
56-53-1(EPA Substance)

Safety Data

Hazard Codes 
T,N
Risk Statements 
R45:May cause cancer.
R61:May cause harm to the unborn child.
R36/37/38:Irritating to eyes, respiratory system and skin .
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R40:Limited evidence of a carcinogenic effect.
Safety Statements 
S53:Avoid exposure-obtain special instruction before use .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
RIDADR 
UN 3077 9/PG 3

WGK Germany 
3

RTECS 
WJ5600000


10
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29072990
Safety Profile
Confirmed carcinogen producing skin, liver, and lung tumors in exposed humans as well as uterine and other reproductive system tumors in the female offspring of exposed women. Experimental carcinogenic, neoplas tigenic, tumorigenic, and teratogenic data. A transplacental carcinogen. A human teratogen by many routes. Poison by intraperitoneal and subcutaneous routes. It causes glandular system effects by sktn contact. Human reproductive effects by ingestion: abnormalspermatogenesis; changes in testes, epididymis, and sperm duct; menstrual cycle changes or disorders; changes in female ferulity; unspecified maternal effects; developmental abnormalities of the fetal urogenital system; germ cell effects in offspring; and delayed effects in newborn. Implicated in male impotence and enlargement of male breasts. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and fumes. See also ETHINYL ESTRADIOL.
Hazardous Substances Data
56-53-1(Hazardous Substances Data)
Toxicity
LD50 oral in rat: > 3gm/kg

Raw materials And Preparation Products

Raw materials
1,4-Dioxane-->Formamide

Hazard Information

General Description
Odorless tasteless white crystalline powder.
Reactivity Profile
DIETHYLSTILBESTROL(56-53-1) is incompatible with strong oxidizing agents, strong bases, acid chlorides and acid anhydrides .
Air & Water Reactions
Insoluble in water.
Fire Hazard
Flash point data for this chemical are not available; however, DIETHYLSTILBESTROL is probably combustible.
Description
Diethylstilbestrol (DES) is a nonsteroidal, synthetic stilbene derivative with estrogenic activity. It is an odorless, white crystalline powder, with a molecular weight of 268.36. Its cisisomer tends to revert to the trans-form.
Chemical Properties
White Solid
Originator
DES,Amfre-Grant,US,1946
Uses
Diethylstilbestrol is a synthetic nonsteroidal estrogen that was formerly used in estrogenic hormone therapy (for menstrual disorders, postpartum breast engorgement, postcoital contraceptive, prevention of spontaneous abortion) and in chemotherapy of various cancers, including postmenopausal breast cancer and prostate cancer. It was also used in biomedical research and veterinary medicine (growth promoter for cattle and sheep; veterinary drug to treat estrogen deficiency disorders).
Uses
A synthetic, nonsteroidal estrogen. Recomended solvents are DMSO, DMF and ethanol, even in these solvents do not store in solution for any prolonged period of time.
Indications
Diethylstilbestrol is one of the older synthetic estrogens in use. It was used to treat prostate cancer but is now rarely used for this purpose because of its adverse effects,although it is occasionally used in postmenopausal women with breast cancer. It is taken orally in tablet form.
Manufacturing Process
50 parts by weight of p-hydroxypropiophenone are dissolved in 200 parts by weight of a 12.5% solution of caustic soda and shaken with 350 parts by weight of 3% sodium amalgam. The sodium salt of the pinacol thereby precipitating is reacted with glacial acetic acid, whereby the free pinacol is obtained (MP 205°C to 210°C, after purification 215°C to 217°C). The yield amounts to 95% of the theoretical. The pinacol is suspended in ether and gaseous hydrogen chloride introduced, whereby water separates and the pinacolin formed is dissolved in the ether, from which it is obtained by evaporation as a viscous oil (diacetateof MP 91°C). The yield is quantitative.
40 parts by weight of pinacolin are dissolved in ethyl alcohol and gradually treated with 80 parts by weight of sodium under reflux. The solution is decomposed with water and the pinacolin alcohol formed extracted from the neutralized solution with ether. The pinacolin alcohol is a viscous oil which is characterized by a dibenzoate of MP 172°C. The yield is 95% of the theoretical.
A solution of 30 parts by weight of pinacolin alcohol in ether is saturated with hydrogen chloride at room temperature and the ether solution then agitated with bicarbonate. After concentration by evaporation it leaves behind the crude diethylstilbestrol [α,β-(p,p'-dihydroxydiphenyl)-α,β-diethylethylene] which, when recrystallized from benzene, melts at 170°C to 171°C. The yield amounts to 75% of the calculated. The total yield of diethylstilbestrol, calculated on p-hydroxypropiophenone, is 68% of the theoretical.
Brand name
Stilbestrol (Tablicaps); Stilbetin (Bristol-Myers Squibb);Distilbene;Oestro-gynedron;Stilphostrol.
Therapeutic Function
Estrogen
World Health Organization (WHO)
Diethylstilbestrol, a synthetic estrogen which is a stilbene derivative, was introduced into obstetric practice in the late 1940s and subsequently widely used for the treatment of threatened abortion. This use was later shown to be associated with an increased risk of vaginal cancer in the offspring which resulted in restrictive regulatory action in several countries. Diethylstilbestrol and other stilbenes remain available in many countries, however, for the treatment of certain hormone-dependent neoplasms including carcinoma of the prostate and postmenopausal breast cancer. (Reference: (WHODI) WHO Drug Information, 77.1, 16, 1977)
Side effects
These include sodium retention and oedema,nausea,gynaecomastia and impotence in men, and venous and arterial thrombosis. It can cause bone pain and hypercalcaemia when used for breast cancer.
Carcinogenicity
Diethylstilbestrol is known to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in humans.
Environmental Fate
Diethylstilbestrol is a known teratogen and carcinogen. Experimental studies using transgenic estrogen receptor knockout animals suggest that binding and activation of the estrogen receptor is required to elicit diethylstilbestrol toxicity. Hence, diethylstilbestrol lesions primarily appear in tissues enriched with estrogen receptors. Diethylstilbestrol binds to the estrogen receptor with a very high affinity and forms a complex with the target tissue. The complex then internalizes in to the cell and translocates to the nucleus. Once in the nucleus, diethylstilbestrol may directly bind with the cellular DNA and cause mutations and unscheduled DNA synthesis. Diethylstilbestrol is also known to induce aneuploidy.
Toxicity evaluation
Diethylstilbestrol’s production and use in biochemical research, medicine, and veterinary medicine may result in its release to the environment through various waste streams. It may also be released to the environment during transport, storage, or disposal. If released to soil, diethylstilbestrol is predicted to strongly adsorb to the soil. Volatilization from the dry or wet soil surface would probably be unlikely. The extent of biodegradation in soil is not known, although diethylstilbestrol has been shown to be resistant to degradation in activated sludge. If released to water, diethylstilbestrol may bioconcentrate in aquatic organisms and strongly adsorb to suspended solids and sediments. Diethylstilbestrol is expected to be essentially nonvolatile on water surfaces. Diethylstilbestrol would not be susceptible to hydrolysis. The extent of biodegradation in natural waters is not certain, although diethylstilbestrol has been shown to be resistant to degradation in activated sludge. If released to the atmosphere, diethylstilbestrol vapors should rapidly oxidize, primarily by reaction with ozone. It is expected to exist solely in the particulate phase in an ambient atmosphere. Particulatephase diethylstilbestrol may be removed from the air by wet and dry deposition.

Material Safety Data Sheet(MSDS)

Spectrum Detail

Well-known Reagent Company Product Information

SupplierMore