Menformon A

Base Information

• Chemical Name: Menformon A
• CAS No.: 53-16-7
• Molecular Formula: C18H22O2
• Molecular Weight: 270.371
• Hs Code.: 29335995
• NSC Number: 9699
• Wikidata: Q27166915
• ChEMBL ID: CHEMBL756
• Mol file: 53-16-7.mol

Synonyms:Menformon A;E1;Oestrone;Estrone-[2,3,4-13C3];Fermidyn;Estrin;Femestrone inj.;NSC9699;Follidrin (tablets);1,3,5-Oestratrien-3-ol-17-one;NCGC00015423-03;Duogen (Salt/Mix);ST019426;component of Spanestrin-P;CHEMBL756;Oprea1_745128;MLS001331716;SCHEMBL157262;CHEBI:95131;DNXHEGUUPJUMQT-UHFFFAOYSA-N;HMS2235H07;HMS3370A22;MFCD00003620;3-Hydroxy-17-ketoestra-1,5-triene;3-Hydroxy-17-ketooestra-1,5-triene;AKOS001116292;1,5(10)-Estratrien-3-ol-17-one;1,5(10)-Oestratrien-3-ol-17-one;3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one;5-hydroxy-15-methyltetracyclo[8.7.0.0<2,7>.0<11,15>]heptadeca-2(7),3,5-trien-1 4-one;NCGC00015423-02;NCGC00142363-01;NCGC00142363-02;3-Hydroxyestra-1,5(10)-trien-17-one;SMR000814705;SY036249;3-Hydroxy-1,5(10)-oestratrien-17-one;WLN: L E5 B666 FVTTT&J E1 OQ;3-Hydroxy-oestra-1,5(10)-trien-17-one;3-Hydroxy-1,3,5(10)-oestratrien-17-one;CS-0348902;FT-0668040;FT-0668041;.delta.-1,5-Estratrien-3.beta.-ol-17-one;delta-1,3,5-Estratrien-3.beta.-ol-17-one;EN300-18760;Estra-1,5(10)-trien-17-one, 3-hydroxy-;.delta.-1,5-Oestratrien-3.beta.-ol-17-one;delta-1,3,5-Oestratrien-3.beta.-ol-17-one;.DELTA.-1,3,5(10)-Estratrien-3-ol-17-one;BRD-A14458579-001-08-5;Q27166915;5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-14-one;1187829-63-5;3-Hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-17h-cyclopenta[a]phenanthren-17-one

Chemical Property of Menformon A

Chemical Property:

• Appearance/Colour: crystalline solid
• Vapor Pressure: 1.54E-08mmHg at 25°C
• Melting Point: 258-261 ºC
• Refractive Index: 165 ° (C=1, Dioxane)
• Boiling Point: 445.2 ºC at 760 mmHg
• PKA: pKa 10.77±0.02(H2O)(Approximate)
• Flash Point: 189.7 ºC
• PSA: 37.30000
• Density: 1.164 g/cm³
• LogP: 3.81740
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Dioxane (Slightly), Ethanol (Slightly), Methanol (Slightl
• Water Solubility.: 0.03 g/L
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 270.161979940
• Heavy Atom Count: 20
• Complexity: 418

Purity/Quality:

≥98% ^*data from raw suppliers

Folliculin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,F
• Statements: 45-60-61-64-40-63-39/23/24/25-23/24/25-11
• Safety Statements: 53-45-36/37-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2=O)CCC4=C3C=CC(=C4)O
• Natural Steroid Hormone: Estrone is a natural steroid hormone produced by the ovary, placenta, and adrenal cortex in both humans and animals. It is excreted in urine and feces, ultimately being released into the environment.
• Gene Expression Profiles: Gene profiles influenced by pre- and postmenopausal estrogens differ. Estrone stimulates certain genes associated with epithelial-to-mesenchymal transition (EMT), invasion, and metastasis in vivo.
• Feminizing Hormone Treatment: Estrone is relevant in feminizing hormone treatment for transgender women. It is an estrogen receptor agonist and a metabolite of estradiol. The route of administration (oral vs. transdermal) affects the concentration of estrone, with oral estradiol leading to higher levels. Estrone's relative binding affinity for estrogen receptors is lower than that of estradiol, but its role in feminization varies among individuals.
• Predictor of Circulating Estradiol: Estrone is a strong predictor of circulating estradiol levels in women aged 70 years and older.
• Environmental Contamination: Global-scale contamination of soil and aquatic environments with estrone results from the widespread use of animal manure as fertilizer. Understanding the degradation of estrone by microorganisms is essential for bioremediation efforts.
• Physiological Role: Estrogens, including estrone, regulate various physiological processes such as sexual development, stress response, tissue differentiation, and energy metabolism. During menopause, estrone becomes the principal estrogen in circulation as the ovaries cease estradiol production.

Technology Process of Menformon A

There total 238 articles about Menformon A 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: 93.0%

estrone 3-methyl ether (1624-62-0) → Estrone (53-16-7)

Guidance literature:

With aluminium trichloride; sodium iodide; In dichloromethane; acetonitrile; for 5.5h; Heating;

Reference yield: 91.0%

(8R,9S,13S,14S)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dithiolan]-3-ol (14485-61-1) → Estrone (53-16-7)

Guidance literature:

With iodosylbenzene; In dichloromethane; at 20 ℃; for 1.16667h;

DOI:10.24820/ARK.5550190.P011.476

Reference yield: 16.0%

19-hydroxy-4β,5-epoxy-5β-androstane-3,17-dione (53875-00-6) → Estrone (53-16-7) + 2-hydroxyestrone (362-06-1,4735-38-0) + 2β,19-epoxyandrost-4-ene-3,17-dione (124522-67-4) + 2α,19-dihydroxyandrost-4-ene-3,17-dione (53875-01-7)

Guidance literature:

With sulfuric acid; In dimethyl sulfoxide;

upstream raw materials:

1,4-dioxane

(13α)-3-hydroxyestra-1(10),2,4-trien-17-one

ethanol

Estriol

Downstream raw materials:

3-(2-tetrahydropyranyloxy)-1,3,5(10)estratrien-17β-ol

oestrone acetate

3-hydroxy-1,3,5(10)-estradien-17-one 3-(3-carboxypropanoate)

3-benzyloxy-estra-1,3,5(10),15-tetraen-17β-ol

Refernces

HYDROXYLATION DE L'ESTRONE ET DE SON ACETATE PAR LE PEROXYDE D'HYDROGENE EN MILIEU SUPERACIDE

10.1016/S0040-4020(01)91262-1

The research focuses on the hydroxylation of estrone and its acetate using hydrogen peroxide in a superacidic medium, specifically sulfur hexafluoride-hydrogen fluoride (SbF6-HF). The purpose of the study was to investigate the reactions of these compounds under superacidic conditions and to explore the formation of hydroxylated products. The researchers observed that estrone and its acetate reacted with hydrogen peroxide to yield hydroxylated compounds, with the formation of specific compounds being attributed to electrophilic attacks on the protonated substrates. The study concluded that higher acidity favored the rearrangement of products to yield phenols, and under the reaction conditions, compounds 3b and 1) were slowly converted into the corresponding phenols 3a and 1r. Key chemicals used in the process included estrone, its acetate, hydrogen peroxide, and the superacidic medium of SbF6-HF. The research provided insights into the behavior of organic compounds under extreme acidic conditions and contributed to the understanding of the hydroxylation reactions of steroidal compounds.

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Monofluoroalkyl Halides for Late-Stage Monofluoroalkylation

10.1002/anie.201803228

The study presents a nickel-catalyzed reductive cross-coupling method for the late-stage monofluoroalkylation of aryl halides with unactivated fluoroalkyl halides. The key to this method's success lies in the combination of diverse readily available nitrogen ligands, specifically bidentate and monodentate pyridine-type ligands, which generate easily tunable catalysts. This approach enables the synthesis of fluoroalkylated drug-like molecules under mild conditions with high efficiency and excellent functional group tolerance. The researchers optimized the reaction conditions using phenyl iodide as the substrate and 1-fluoro-1-iodo ethylbenzene as the coupling partner, identifying dmbpy and 4-CN-Py as the optimal ligands. The method demonstrated broad scope, successfully fluorinating various aryl iodides and bromides, including those with electron-donating and withdrawing groups, as well as complex pharmaceuticals like Ezetimibe and Estrone. The study also extended the method to non-fluorinated alkyl halides, showing its potential for late-stage alkylation of drugs. Mechanistic studies suggested the involvement of a nickel-based catalytic cycle with a free monofluoroalkyl radical. This combinatorial catalysis strategy offers a solution for nickel-catalyzed reductive cross-coupling reactions and provides an efficient way to synthesize fluoroalkylated drug-like molecules for drug discovery.