3589-90-0

Usage

Chemical class

Synthetic estrogen derivative

Parent compound

Estradiol

Therapeutic use

Hormone replacement therapy in postmenopausal women

Alleviates symptoms

Hot flashes, vaginal dryness

Structural feature

Tetrahydro-2H-pyran-2-yloxy group attached to the 17β position

Uniqueness

A unique estrogen derivative with potential therapeutic applications

Role in the body

Important for the regulation of the female reproductive system and various other bodily functions

Pharmaceutical research

Used for studying estrogen receptor binding and activity
These properties and specific content provide a comprehensive overview of 17β-(Tetrahydro-2H-pyran-2-yloxy)estra-1,3,5(10)-trien-3-ol, highlighting its chemical structure, therapeutic applications, and significance in both medical treatment and pharmaceutical research.

InChI:InChI=1/C23H32O3/c1-23-12-11-18-17-8-6-16(24)14-15(17)5-7-19(18)20(23)9-10-21(23)26-22-4-2-3-13-25-22/h6,8,14,18-22,24H,2-5,7,9-13H2,1H3

Upstream product

• 50-28-2 estradiol 
• 135598-57-1 3β,19-O,O'-diacetyl-17β-O''-(tetrahydropyranyl)androst-5-ene-3β,17β,19-triol 
• 135598-56-0 3β,19-O,O'-diacetylandrost-5-ene-3β,17β,19-triol 
• 101296-67-7 17β-O-(tetrahydropyranyl)-19-oxotestosterone 
• 135598-58-2 17β-O-(tetrahydropyranyl)androst-5-ene-3β,17β,19-triol 
• 2857-44-5 3β,19-O,O'-diacetyl-19-hydroxydehydroepiandrosterone 
• 2857-45-6 3β,19-dihydroxy-5-androsten-17-one 
• 50704-79-5 19-nortestosterone tetrahydropyranyl ether 
• 110-87-2 3,4-dihydro-2H-pyran 
• 3589-91-1 3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene 
• 434-22-0 19-nortestosterone 
• 112506-37-3 3-O-(tert-butyldimethylsilyl)-17β-O'-(tetrahydropyranyl)-19-oxoandrosta-2,4-diene-3,17β-diol 

Downstream Products

• 50-28-2 estradiol 

Relevant academic research and scientific papers

Mechanistic Studies on a Placental Aromatase Model Reaction

Aromatase is a cytochrome P-450 enzyme that converts androgens to estrogens via three successive oxidative reactions. The mechanism of the third step has previously been intensively studied, with no clear resolution. A leading theory for the third step proposes nucleophilic attack of the heme ferric peroxide species on the 19-aldehyde intermediate to produce a 19-hydroxy 19-ferric peroxide intermediate. We have shown previously that analogues of this intermediate failed to aromatize under nonenzymatic conditions. In this study, we prepared a 2,4-dien-3-ol analogue of the 19-aldehyde intermediate and showed that it reacted with HOOH to produce the corresponding estrogen derivative. Evidence has been accrued to suggest that this reaction, which we have called the aromatase model reaction, involves a 19-hydroxy 19-hydroperoxide intermediate. The model reaction was shown to be faithful to the actual aromatase-catalyzed reaction with regard to stoichiometric formic acid production, 18O-incorporation patterns, and stereoselectivity for 1/3-hydrogen removal. A kinetic analysis at 37°C was also performed, and the reaction was demonstrated to be pseudo-first-order by using an excess of HOOH, and first-order with respect to HOOH at the concentrations studied. The effects of KOH, EDTA, and BHT on the reaction were also examined, and are discussed.

Proton and carbon-13 nuclear magnetic resonance spectroscopy of diastereoisomeric 3- and 17β-tetrahydropyranyl ether derivatives of estrone and estradiol

Protection of 3- and 17β-hydroxyl groups of estrone and estradiol as tetrahydropyranyl ether derivatives led to mixtures of 2'(R)- and 2'(S)-diastereoisomers which were separated by crystallization (3-tetrahydropyranyl ethers), or by thin layer chromatogr

Conversion of 19-Nortestosterone to β-Estradiol

Selective aromatization of cyclohexenone was achieved via abstraction of an α-proton of 2-cyclohexenone by LDA followed by treatment with phenylselenyl chloride which gave the corresponding phenol upon oxidation.This new methodology was applied in the conversion of 19-Nortestosterone to β-Estradiol.