Diethylstilbestrol

Base Information

• Chemical Name: Diethylstilbestrol
• CAS No.: 56-53-1
• Deprecated CAS: 8026-45-7,8028-09-9,8030-34-0,8049-42-1,8053-00-7,8028-09-9,8030-34-0,8049-42-1,8053-00-7
• Molecular Formula: C18H20O2
• Molecular Weight: 268.356
• Hs Code.: 29072990
• European Community (EC) Number: 200-278-5,678-392-3
• NSC Number: 756736,3070
• UN Number: 3077
• UNII: 731DCA35BT
• DSSTox Substance ID: DTXSID3020465
• Nikkaji Number: J113.282B,J2.801K
• Wikipedia: Diethylstilbestrol,Stilbestrol
• Wikidata: Q423989
• NCI Thesaurus Code: C433
• RXCUI: 3390
• Pharos Ligand ID: G6MP2G77G9WR
• Metabolomics Workbench ID: 42655
• ChEMBL ID: CHEMBL411
• Mol file: 56-53-1.mol

Synonyms:Agostilben;Apstil;Diethylstilbestrol;Diethylstilbestrol, (Z)-Isomer;Diethylstilbestrol, Disodium Salt;Distilbène;Estrogen, Stilbene;Stilbene Estrogen;Stilbestrol;Tampovagan

Chemical Property of Diethylstilbestrol

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 3.29E-07mmHg at 25°C
• Melting Point: 170-172 °C(lit.)
• Refractive Index: 1.603
• Boiling Point: 407.1 °C at 760 mmHg
• PKA: pKa 9.02(H2O t=25 I=0.025) (Uncertain)
• Flash Point: 186.9 °C
• PSA: 40.46000
• Density: 1.107 g/cm³
• LogP: 4.82860
• Storage Temp.: 0-6°C
• Solubility.: methanol: 0.1 g/mL, clear, faintly yellow
• Water Solubility.: PRACTICALLY INSOLUBLE
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 268.146329876
• Heavy Atom Count: 20
• Complexity: 286
• Transport DOT Label: Class 9

Purity/Quality:

99.5% ^*data from raw suppliers

Des ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, N
• Hazard Codes: T,N
• Statements: 45-61-36/37/38-51/53-40
• Safety Statements: 53-36/37/39-45-60-61-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(=C(CC)C1=CC=C(C=C1)O)C2=CC=C(C=C2)O
• Isomeric SMILES: CC/C(=C(/CC)\C1=CC=C(C=C1)O)/C2=CC=C(C=C2)O
• Recent ClinicalTrials: Comparison Between Volatile Anesthetic-desflurane and Total Intravenous Anesthesia With Propofol and Remifentanil on Early Recovery Quality and Long Term Prognosis of Patients Undergoing Pancreatic Cancer and Common Bile Duct Cancer Surgery
• Recent EU Clinical Trials: GRACE-trial: A randomized active-controlled trial for vulvovaginal atrophy in breast cancer patients on endocrine therapy
• Description: Diethylstilbestrol (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.
• Uses: Diethylstilbestrol 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 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).
• 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.
• Therapeutic Function: Estrogen

Technology Process of Diethylstilbestrol

There total 69 articles about Diethylstilbestrol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

Diethylstilbestrol dimethyl ether (130-79-0) → diethylstilbestrol (56-53-1,8053-00-7)

Guidance literature:

Diethylstilbestrol dimethyl ether; With boron tribromide; In dichloromethane; at -78 - 20 ℃; for 2h; Inert atmosphere;

With water; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1016/j.ejmech.2015.09.005

Reference yield: 27.0%

4-hydroxypropiophenone (70-70-2) → diethylstilbestrol (56-53-1,8053-00-7) + 3,4-bis(4-hydroxyphenyl)-3,4-hexanediol (7507-01-9) + cis-3,4-Bis(p-hydroxyphenyl)-3-hexene (22610-99-7,8053-00-7)

Guidance literature:

With titanium tetrachloride; zinc; In tetrahydrofuran; for 20h; Yield given; Heating;

Reference yield:

3,4-bis-(4-methoxy-phenyl)-hexan-3-ol (5331-23-7) → diethylstilbestrol (56-53-1,8053-00-7)

Guidance literature:

Multi-step reaction with 2 steps

1: KHSO₄ / 195 - 200 °C

2: ethanolic KOH / 200 - 210 °C

With potassium hydroxide; potassium hydrogensulfate;

upstream raw materials:

diethylstilbestrol dimethyl ether

C₂₀H₂₄O₂

1,4-di(4-methoxyphenyl)ethanone

1,2-bis(4-methoxyphenyl)butanone

Downstream raw materials:

Diethylstilbestrol dimethyl ether

(E)-4-[1-ethyl-2-(4-methoxyphenyl)-1-butenyl]-phenol

Clinestrol

3,4-bis-(4-propionyloxy-phenyl)-hex-3c-ene

Refernces

• 1、 Pathe, Gulab Khushalrao,Konduru, Naveen K.,Parveen, Iram,Ahmed, Naseem. "Anti-proliferative activities of flavone-estradiol Stille-coupling adducts and of indanone-based compounds obtained by SnCl4/Zn-catalysed McMurry cross-coupling reactions". . p. 83512 - 83521. Retrieved 2015/10/19.
• 2、 -. "Anti-Claudin 3 Monoclonal Antibody and Treatment and Diagnosis of Cancer Using the Same". . . Retrieved 2010/05/13.