53-45-2

Basic information

• Product Name: 3-DEOXYESTRONE
• Synonyms: 3-deoxyoestrone;adopron;agrestin;deoxyestrone;desoxyestrone;estra-1,3,5(10)-trien-17-one;estratrien-17-one;(8R,9S,13S,14S)-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS NO: 53-45-2
• Molecular Formula: C₁₈H₂₂O
• Molecular Weight: 254.36668
• Mol File: 53-45-2.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 387°Cat760mmHg
• Flash Point: 167.8°C
• Appearance: /
• Density: 1.088g/cm³
• Vapor Pressure: 3.4E-06mmHg at 25°C
• Refractive Index: 1.565
• CAS DataBase Reference: 3-DEOXYESTRONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-DEOXYESTRONE(53-45-2)
• EPA Substance Registry System: 3-DEOXYESTRONE(53-45-2)

Safety Data

• Hazardous Substances Data: 53-45-2(Hazardous Substances Data)

Usage

General Description

3-Deoxyestrone is a synthetic estrogenic compound that is used in scientific research to study hormone receptor binding and interaction. It is a derivative of natural estrogen and has a similar chemical structure and biological activity. 3-Deoxyestrone has been found to have potential applications in the treatment of hormone-related conditions and diseases, such as breast cancer and menopausal symptoms. It is also used as a tool in the development of new drugs and therapies targeting hormone receptors and signaling pathways. However, further research is needed to fully understand its potential benefits and risks for human health.

InChI:InChI=1/C18H22O/c1-18-11-10-14-13-5-3-2-4-12(13)6-7-15(14)16(18)8-9-17(18)19/h2-5,14-16H,6-11H2,1H3/t14-,15-,16+,18+/m1/s1

Upstream product

• 2529-64-8 3-Deoxyestradiol 
• 4003-22-9 (8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl pivalate 
• 1408168-73-9 potassium [2-(benzyloxy)ethyl]-trifluoroboranuide 
• 92817-04-4 estrone triflate 
• 53-16-7 Estrone 
• 2529-44-4 Estron-diethylphosophat 
• 2626-19-9 Oestradiol-3-diethylphosphat 
• 50-28-2 estradiol 
• 26435-99-4 <(1-phenyl-1H-tetrazol-5-yl)oxy>estra-1,3,5(10)-trien-17-one 
• 132636-60-3 (8R,9S,13S,14S)-3-(1,1-Dioxo-1H-1λ⁶-benzo[d]isothiazol-3-yloxy)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one 

Downstream Products

• 52-77-7 17α-Aethinyl-oestra-1,3,5(10)-trien-17β-ol 
• 1150106-19-6 C₂₄H₂₇NO 
• 1150106-18-5 C₂₄H₂₈BrNO 
• 112648-42-7 N-Benzylestra-1,3,5(10)-trien-17β-amine 

Relevant articles and documents

Hydrogen peroxide induced activation of gene expression in mammalian cells using boronate estrone derivatives

Keeping the boron out of the ER: A genetic switch was engineered that activates gene expression in the presence of H2O2 (see scheme). The use of a boronate group on an estrone molecule allows for activation of gene expression through binding of the estrogen receptor only when the boron group is oxidized by H2O2. This sensor is highly sensitive and specific for H2O2. Copyright

Nickel-Catalyzed Hydrodeoxygenation of Aryl Sulfamates with Alcohols as Mild Reducing Agents

The nickel-catalyzed hydrodeoxygenation of aryl sulfamates has been developed with alcohols as mild reductants. A variety of functional groups and heterocycles were tolerated in this reaction system to give the desired products in high yields. In addition, the gram-scale process and stepwise cine-substitution were also achieved with high efficiency.

Development of a gram-scale synthesis of pbrm, an irreversible inhibitor of 17beta-hydroxysteroid dehydrogenase type 1

Efforts toward the development of a reliable gram scale synthesis of PBRM, a potent and selective steroidal covalent inhibitor of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1), are described. Among the three synthetic routes (C-E) developed herein, route E is the most efficient one with only 6 chemical steps from commercially available estrone, and an overall yield of 13% leading to PBRM with a high HPLC grade purity (99.7%) after recrystallization. Important improvements have been achieved in this sequence from previous reported routes (A and B). Notably, we used a palladium catalyzed Suzuki-Miyaura cross-coupling reaction to rapidly install the requested C3 chain on estrone. Also, catalytic hydrogenation of the C16-enone was shortened by half using Pearlman's catalyst. Finally, we used a selective bromination through deoxygenation of alcohol at the last step of the sequence to provide PBRM without dehydration of its carboxamide functionality, a persistent problem observed in other routes. Crystals of PBRM were also obtained from recrystallization in acetonitrile and submitted to x-ray analysis, which confirmed the PBRM structure. This work now makes it possible to start a proof-of-principle in a non-human primate model for the treatment of endometriosis, while supporting its future pharmacological development.

A facile and mild Pd-catalyzed one-pot process for direct hydrodeoxygenation (HDO) phenols to arenes through a ArOSO2F intermediates transformation

A practical one-pot process for hydrodeoxygenation (HDO) of phenolic derivatives to their corresponding arenes was developed. This method provided a facile route to upgrading bio-oil. The substrate scope of this protocol was wide, complicated and multi-phenolic compounds were also smoothly hydrodeoxygenated to their corresponding arenes.