5776-72-7

Basic information

• Product Name: hexestrol
• Synonyms: HEXESTROL;Dl-dea;Isohexestrol;Nsc 35752;Phenol, 4,4'-(1,2-diethyl-1,2-ethanediyl)bis-, (R*,R*)-(+-)-;Phenol, 4,4'-(1,2-diethyl-1,2-ethylenediyl)bis-, (R*,R*)-(+-)- (9ci)
• CAS NO: 5776-72-7
• Molecular Formula: C₁₈H₂₂O₂
• Molecular Weight: 270.37
• Mol File: 5776-72-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 186.5°C
• Boiling Point: 373.48°C (rough estimate)
• Flash Point: 181.6°C
• Appearance: /
• Density: 1.0310 (rough estimate)
• Refractive Index: 1.5510 (estimate)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: hexestrol(CAS DataBase Reference)
• NIST Chemistry Reference: hexestrol(5776-72-7)
• EPA Substance Registry System: hexestrol(5776-72-7)

Safety Data

• Hazardous Substances Data: 5776-72-7(Hazardous Substances Data)

Usage

Description

Hexestrol, a nonsteroid synthetic estrogen, is an odorless, white, crystalline powder with specific chemical properties. It is soluble in ether, acetone, alcohol, and methanol, but practically insoluble in water and sensitive to light. This synthetic estrogen is known for its estrogenic hormone activity and is used in various medical applications.

Uses

Used in Medicine:
Hexestrol is used as an estrogenic hormone in the medical field for various indications, including the treatment of conditions related to estrogen deficiency or imbalance.
Used in Prostate Cancer Treatment:
In the field of oncology, hexestrol is used as a treatment option for prostate cancer or its hypertrophy in men. It helps in managing the symptoms and progression of the disease by targeting the hormonal aspects associated with prostate cancer growth.
Used for Estrone Indications:
Hexestrol is also utilized for the same indications as estrone, which includes the treatment of menopausal symptoms, osteoporosis, and other conditions related to estrogen deficiency in women. Its synthetic nature allows for a controlled and targeted approach to hormone replacement therapy.

Synthesis

Hexestrol, 4,4
-(1,2-diethylethylene)diphenol (28.1.29), is a derivative of α,β- diphenylethane, and it is a synthetic estrogen. Hexestrol is made in a Wurtz dimerization reaction of 1-bromo-1-(4-methoxyphenyl)propane (28.1.27) in the presence of sodium, magnesium, aluminum, or iron. The initial 1-bromo-1-(4-methoxyphenyl)propane (28.1.27) is made in turn by addition reaction of hydrogen bromide to 4-methoxy-1- propenylbenzene. Subsequent removal of the methoxy protective groups from the resulting dimerization product (28.1.28) using hydroiodic acid gives hexestrol (28.1.29).

Upstream product

• 130-78-9 racem.-3,4-bis-(4-methoxy-phenyl)-hexane 
• 67-56-1 methanol 
• 56-53-1 diethylstilbestrol 
• 64-17-5 ethanol 
• 130-80-3 Clinestrol 
• 70-70-2 4-hydroxypropiophenone 
• 130-79-0 Diethylstilbestrol dimethyl ether 
• 4390-94-7 1,2-bis(4-methoxyphenyl)butanone 
• 84234-15-1 bis-[1-(4-hydroxy-phenyl)-propylidene]-hydrazine 
• 123-11-5 4-methoxy-benzaldehyde 
• 19115-30-1 1-(4-methoxyphenyl)-2-propyn-1-ol 
• 101942-05-6 4.4'-bis-ethoxycarbonyloxy-α.α'-diethyl-trans-stilbene 
• 64-19-7 acetic acid 
• 13029-44-2 Dienol 

Downstream Products

• 5693-81-2 racem.-3.4-bis-(4t-hydroxy-cyclohexyl-(1r))-hexane 
• 5693-81-2 (+/-)-threo-3-(4c-hydroxy-cyclohexyl-(1r))-4-(4t-hydroxy-cyclohexyl-(1r))-hexane 
• 84-16-2 3,4-bis-(4-hydroxy-phenyl)-hexane 
• 41172-51-4 racem.-3,4-bis-(3-nitro-4-hydroxy-phenyl)-hexane 
• 6033-44-9 racem.-3,4-bis-(4-benzoyloxy-phenyl)-hexane 
• 129579-58-4 threo-3-(Cyclohex-3-en-1-on-4-yl)-4-(4-hydroxyphenyl)-hexane 
• 13026-26-1 threo-4-(4-Hydroxyphenyl)-3-(4-methoxyphenyl)-hexane 
• 130-78-9 racem.-3,4-bis-(4-methoxy-phenyl)-hexane 

Relevant articles and documents

Tetrahydrofuran-mediated radical processes: Stereoselective synthesis of d,l-hexestrol

The highly stereoselective synthesis of d,l-hexestrol (1), an inhibitor of microtubule assembly, is developed by using, as a key step, an intermolecular coupling of Co2(CO)6-complexed propargyl radicals. The latter are generated by novel complementary processes involving an interaction of tetrahydrofuran with Co2 (CO)6-complexed propargyl alcohols and cations. An isomerically pure d,l-μ-η2-[3,4-di(4-methoxyphenyl)-1, 5-hexadiyne]-bis-dicobalthexacarbonyl (d,l-6) is isolated in 69-91% yield with intermolecular coupling reactions exhibiting an excellent chemo-(0.5-7%) and d,l-diastereoselectivity (90-94%). The structure of d,l-6 is determined by X-ray diffraction. The subsequent steps include BBr3-induced demethylation of 4-methoxyaryl groups, demetalation with cerium(IV) ammonium nitrate, and hydrogenation of acetylenic termini affording d,l-hexestrol (1).