17253-36-0

Basic information

• Product Name: 3-methoxyestra-1,3,5(10),6-tetraen-17-one
• Synonyms: 3-methoxyestra-1,3,5(10),6-tetraen-17-one;3-Methoxy-19-norandrosta-1,3,5(10),6-tetrene-17-one;3-Methoxyestra-1,3,5(10),6-tetren-17-one
• CAS NO: 17253-36-0
• Molecular Formula: C₁₉H₂₂O₂
• Molecular Weight: 282.37678
• EINECS: 241-287-4
• Mol File: 17253-36-0.mol

Chemical Properties

• Boiling Point: 435.1°Cat760mmHg
• Flash Point: 190.4°C
• Appearance: /
• Density: 1.124g/cm³
• Vapor Pressure: 8.97E-08mmHg at 25°C
• Refractive Index: 1.57
• CAS DataBase Reference: 3-methoxyestra-1,3,5(10),6-tetraen-17-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methoxyestra-1,3,5(10),6-tetraen-17-one(17253-36-0)
• EPA Substance Registry System: 3-methoxyestra-1,3,5(10),6-tetraen-17-one(17253-36-0)

Safety Data

• Hazardous Substances Data: 17253-36-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
3-Methoxyestra-1,3,5(10),6-tetraen-17-one is used as a pharmaceutical agent for its estrogenic activity, primarily for the regulation of the menstrual cycle and alleviation of menopausal symptoms. Its role in these areas is due to its ability to mimic the effects of the natural hormone, providing relief and balance to the hormonal system.
Used in Menstrual Cycle Regulation:
3-Methoxyestra-1,3,5(10),6-tetraen-17-one is used as a hormonal regulator to manage irregular menstrual cycles, providing a means to stabilize and regularize the menstrual cycle in women.
Used in Menopause Symptom Alleviation:
3-methoxyestra-1,3,5(10),6-tetraen-17-one is used as a therapeutic agent to alleviate symptoms associated with menopause, such as hot flashes and mood swings, by providing the necessary hormonal support.
Used in Cancer Research:
3-Methoxyestra-1,3,5(10),6-tetraen-17-one is used in scientific research for its potential anti-cancer properties, particularly in the study of breast cancer treatment. Its estrogenic activity is being investigated for its impact on tumor growth and progression.
Used in Fertility and Reproductive Health Research:
3-methoxyestra-1,3,5(10),6-tetraen-17-one is used as a subject of research in the field of fertility and reproductive health, exploring its potential role in enhancing fertility outcomes and supporting reproductive system health.
Overall, 3-methoxyestra-1,3,5(10),6-tetraen-17-one has demonstrated promise in various areas of medical and pharmaceutical research, with potential applications in the development of treatments for hormonal imbalances, menopause, cancer, and reproductive health conditions.

InChI:InChI=1/C19H22O2/c1-19-10-9-15-14-6-4-13(21-2)11-12(14)3-5-16(15)17(19)7-8-18(19)20/h3-6,11,15-17H,7-10H2,1-2H3

Upstream product

• 130593-50-9 3-methoxy-17-oxoestra-1,3,5⁽¹⁰⁾,6-tetraen-6-yl triflate 
• 19115-79-8 3-O-methylestra-1,3,5⁽¹⁰⁾-trien-3-ol-6,17-dione 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 95282-98-7 19-acetoxyandrosta-1,4-diene-3,17-dione 
• 2229-26-7 19-acetoxy-androst-4-ene-3,17-dione 
• 510-64-5 19-hydroxy-4-androstene-3,17-dione 
• 24130-35-6 19-acetoxy-androsta-1,4,6-trien-3,17-dione 
• 149-73-5 trimethyl orthoformate 
• 13209-45-5 estra-4,6-diene-3,17-dione 
• 734-32-7 estra-4-ene-3,17-dione 
• 434-22-0 19-nortestosterone 
• 67-56-1 methanol 
• 2208-12-0 6-dehydroestrone 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 1624-62-0 estrone 3-methyl ether 
• 56614-59-6 14-dehydroequilenin-3-methylether 
• 33760-56-4 14-dehydro-17β-dihydroequilenin-3-methylether 
• 3907-67-3 3-O-methylequilinine 
• 1229-32-9 d-Isoequilenin methylether 
• 517-09-9 equilenin 
• 1423-97-8 17β-dihydroequilenin 
• 6639-99-2 17α-dihydroequilenin 
• 1229-32-9 (+/-)-3-methoxyestra-1,3,5⁽¹⁰⁾,6,8-pentaen-17-one 
• 1415930-37-8 C₂₈H₃₁NO₄ 
• 643764-64-1 (8R,9S,13S,14S,17S)-3-Methoxy-13-methyl-17-[4-(pyrrolidin-1-ylazo)-phenylethynyl]-9,11,12,13,14,15,16,17-octahydro-8H-cyclopenta[a]phenanthren-17-ol 

Relevant articles and documents

Practical semisynthesis of equilenin and its derivatives

Equilenin 2 and its derivatives are important intermediates in the synthesis of steroidal drugs. Until now, these estrogens were produced by extraction from pregnant mare's urine due to the lack of efficient synthetic methods. Most reported semisyntheses of equilenin involve expensive raw materials or toxic reagents to suppress undesired epimerization at C/D ring juncture. Herein, we reported a practical synthesis of highly pure equilenin and its derivatives from an easily available raw material 6 with conventional reagents.

Acid catalysed reaction of estrones with neopentyl glycol under forced conditions

Upon reaction with an excess of 2,2-dimethylpropane-1,3-diol (neopentyl glycol) under acid catalysis, estrones form 17-O-[2',2'-dimethyl-2'-(5", 5"-dimethyl-1",3"-dioxanyl)ethyl] substituted estra-3,17β-diols. The reaction represents a formal reduction of a keto function under acidic conditions in the absence of a metal.

Acid catalysed reaction of indanones, tetralones and benzosuberone with neopentyl glycol and other alkanediols under forced conditions

Upon reaction with an excess of 2,2-dimethylpropane-1,3-diol (neopentyl glycol, NPG) under acid catalysis, indanones and tetralones yield indenes and dihydronaphthalenes, respectively. The reaction can also be carried out with butane-1,3-diol.

C(10)-C(19) bond cleavage reaction of 19-oxygenated androst-4-ene-3,6-dione steroids under various conditions

C(10)-C(19) bond cleavage reaction of 19-hydroxy- and 19-oxoandrost-4-ene- 3,6,17-triones (5, 6) was explored under various conditions. Treatment of steroids 5 and 6 with KOH in MeOH gave the A-ring aromatized product 6-oxoestrone (11) in a fair yield, respectively, in contrast, the treatment with a weak base yielded 4-methyl steroid 17 (20%) in the case of 19-alcohol 5 or 19-nor- Δ5(10)-steroid 9 (12-67%) along with compound 11 (6-27%) in the case of 19-aldehyde 6. Reaction of compound 6 with HCl in MeOH produced 3-methyl ethers of 6-oxoestrone and Δ6-estrone, compounds 12 and 14 (ca. 20% each). Thus, 6-oxosteroids 5 and 6 showed unique C(10)-C(19) bond cleavage reactions with a base or acid.

An Efficient Preparation of 6,7-Didehydroestrogenes

The title compounds are prepared in excellent yield by palladium-catalyzed reduction with triethylammonium formate of enol triflates of 6-oxo-estrogens.