Basic information
- CAS
56-53-1- Standard SMILES
CCC(=C(CC)c1ccc(O)cc1)c1ccc(O)cc1- InChIKey
RGLYKWWBQGJZGM-UHFFFAOYSA-N- Molecular formula
- C18H20O2
- Average molar mass
- 268.3 g/mol
- Monoisotopic mass
- 268.14632988
Overview
A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen.
Names & identifiers
- Preferred name
- Diethylstilbesterol
- IUPAC
- 4-[4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol
- English name
- Diethylstilbestrol
- Molecular formula
- C18H20O2
- Molecular weight
- 268.35
Names & synonyms
RefChem:1083540Diethylstilbesterol6898-97-1(Z,E)-Diethylstilbestrolcis-Diethyl Stilbestrolalpha,alpha'-Diethyl-4,4'-stilbenediol-d4DTXSID3040770Phenol, 4,4'-(1,2-diethyl-1,2-ethenediyl)bis-Stilbestrol;DESStilbesterol, DESDESDiethylstilbestrol BP
Show more names
ALPHAEstrogencarbaldehydecarboxaldehydeα-KetoglutaratepiperidinaminefluorobenzenamineSTILBESTROL
4,4'-(3-HEXENE-3,4-DIYL)DIPHENOLSpectrum_000940Diethylstilboestrol (DE)Prestwick0_000756Prestwick1_000756Spectrum2_000148Spectrum3_000391Spectrum4_000512
Database identifiers
- CAS
56-53-1、6898-97-1- PubChem CID
- 3054
- DTXSID
DTXSID3040770
Properties
Computed structural properties
- XLogP
- 5.1
- Topological polar surface area
- 40.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 4
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 286
Experimental & physicochemical properties
LogP5.07
Solubility1.09e-02 g/L
Melting Point170.5 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 170 · 170-172 °C(lit.)
- Boiling point
- 351.51 °C · 351.51°C (rough estimate)
- Density
- 1.1096 · 1.1096 (rough estimate)
- refractive index
- 1.48 · 1.4800 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- 0.1 g/mL, · methanol: 0.1 g/mL, clear, faintly yellow
- pka
- 9.02 · pKa 9.02(H2O t=25 I=0.025) (Uncertain)
- form
- Crystalline Powder
- color
- White to almost white
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Toxicity Summary
Estrogens diffuse into their target cells and interact with a protein receptor, the estrogen receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. The effect of Estrogen binding their receptors causes downstream increases the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).
Signs and SymptomsSymptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.
Carcinogen Classification1, carcinogenic to humans. (L135)
Safety data
- F
- 10
- PPE
- dust mask type N95 (US), Eyeshields, Gloves, type P2 (EN 143) respirator cartridges
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- WJ5600000
- ridadr
- UN 3077 9/PG 3
- hs_code
- 29072990
- Toxicity
- LD50 oral in rat: > 3gm/kg
- risk_code
- 45-61-36/37/38-51/53-40
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08,GHS09
- hazard_code
- T,N
- safety_code
- 53-36/37/39-45-60-61-36/37
- hazard_class
Chemistry & industry
Pharmacology
Metabolism/MetabolitesHepatic.
Cellular LocationsCytoplasm
Uses & manufacturing
UsesUsed in the treatment of prostate cancer. Previously used in the prevention of miscarriage or premature delivery in pregnant women prone to miscarriage or premature delivery.
Applications
DescriptionDiethylstilbestrol (DES) is a synthetic estrogen receptor agonist that was prescribed to pregnant women in the late 1930s. It was banned in 1971 because of possible links to increased risk of breast cancer in mothers along with congenital abnormalities and increased risk of cancer in offspring. DES is structurally related to, and is as potent as, estradiol in most assays, with a longer half-life. It has a relative binding affinity to sex hormone binding globulin (SHBG) of 0.2 compared to estradiol which has a relative binding affinity of 100. A concentration of 20 μM DES, displaces 30 ± 13% of 3H-estradiol from SHBG in serum.
UsesDiethylstilbestrol has been used:to evaluate the estrogenic activity of diethylstilbestrol by quantitating the expression levels of endogenous estrogen-regulated marker genesto evaluate the estrogenic, androgenic and toxicity responses in bioluminescent yeast bioreporter assay (BLYES)to detect its effect on the proliferation and tyrosinase activity of melanocytes
UsesDiethylstilbestrol 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).
Diethylstilbestrol is an odorless tasteless white crystalline powder. (NTP, 1992)
Related reactions
1 records
Compound notes
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