6544-68-9

Basic information

• Product Name: 18-Methyl-estrone
• Synonyms: 18-METHYL-ESTRONE;18-Methyl-3-hydroxy-1,3,5(10)-estratrien-17-one;18a-Methylestrone;(8R,9S,13S,14S)-13-ethyl-3-hydroxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS NO: 6544-68-9
• Molecular Formula: C₁₉H₂₄O₂
• Molecular Weight: 284.39
• Mol File: 6544-68-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 255 °C(Solv: acetone (67-64-1))
• Boiling Point: 456.2 °C at 760 mmHg
• Flash Point: 194.3 °C
• Appearance: /
• Density: 1.138 g/cm³
• Refractive Index: 1.77
• Solubility: Acetonitrile, DCM
• PKA: 10.25±0.40(Predicted)
• CAS DataBase Reference: 18-Methyl-estrone(CAS DataBase Reference)
• NIST Chemistry Reference: 18-Methyl-estrone(6544-68-9)
• EPA Substance Registry System: 18-Methyl-estrone(6544-68-9)

Safety Data

• Hazardous Substances Data: 6544-68-9(Hazardous Substances Data)

Usage

Description

18-Methyl-estrone, also known as 18α-methylestrone, is a synthetic steroid compound derived from estrone, a naturally occurring estrogen hormone. It is characterized by the presence of a methyl group at the 18th position, which distinguishes it from its natural counterpart. This modification endows 18-Methyl-estrone with unique chemical and biological properties, making it a valuable intermediate in the synthesis of various pharmaceutical compounds.

Uses

Used in Pharmaceutical Industry:
18-Methyl-estrone is used as a key reactant in the synthesis of 2-methoxyestradiol (M262625), a natural metabolite of 17β-Estradiol. This metabolite lacks estrogenic activity and has been the subject of research for its potential therapeutic applications. The synthesis of 2-methoxyestradiol from 18-Methyl-estrone involves a series of chemical reactions, highlighting the importance of 18-Methyl-estrone as a precursor in the development of new pharmaceutical agents.

InChI:InChI=1/C13H8Cl2N2O2S2/c1-2-17-12(19)10(21-13(17)20)8-6-3-5(14)4-7(15)9(6)16-11(8)18/h3-4H,2H2,1H3,(H,16,18)

Upstream product

• 21800-83-9 13β-ethyl-gon-4-en-3,17-dione 
• 848-04-4 dl-13-ethyl-3-methoxygona-1,3,5⁽¹⁰⁾-trien-17-one 
• 797-63-7 levonorgestrel 
• 797-63-7 levonorgestrel 
• 3625-82-9 (+)-17β-hydroxy-13β-ethyl-3-methoxygona-1,3,5(10)-triene 
• 7443-72-3 18-methyl-3-methoxy-1,3,5(10),8-estratetraen-17β-ol 
• 845-89-6 13-Ethyl-3-hydroxy-6,7,11,12,13,16-hexahydro-cyclopenta[a]phenanthren-17-one 
• 848-04-4 (+/-)-13-ethyl-3-methoxy-8α-gona-1,3,5(10)-trien-17-one 
• 848-07-7 (+/-)-13-ethyl-3-methoxygona-1,3,5⁽¹⁰⁾,8,14-pentaen-17-one 

Downstream Products

• 33821-10-2 dl-3-Benzyloxy-13β-aethylgona-1,3,5(10)-trien-17-on 
• 14012-72-7 13β-ethyl-18,19-dinor-17α-pregna-1,3,5(10)-trien-20-yne-3,17β-diol 
• 10453-36-8 dl-3-Benzyloxy-13β-ethylgona-1,3,5(10)-trien-17β-ol 
• 14599-98-5 d-3-Benzyloxy-13β-ethylgona-1,3,5(10)-trien-17β-ol 
• 14088-28-9 l-3-Benzyloxy-13β-ethylgona-1,3,5(10)-trien-17β-ol 
• 848-04-4 dl-13-ethyl-3-methoxygona-1,3,5⁽¹⁰⁾-trien-17-one 

Relevant articles and documents

Preparation method of levonorgestrel pharmacopoeia impurity V

The invention belongs to the technical field of pharmacy, and particularly relates to a preparation method of a levonorgestrel pharmacopoeia impurity V. The preparation method comprises the steps of by taking a compound 1 as an initial raw material, carrying out aromatization reaction, methylation reaction and ethynylation reaction to prepare the levonorgestrel pharmacopoeia impurity V; the aromatization method comprises the steps of dissolving the compound 1 with an organic solvent, adding lithium bromide, controlling the temperature to be -5 to 5 DEG C, then adding copper bromide at the temperature, heating to room temperature, reacting and treating to obtain a compound 2. The product obtained by the method is high in purity and yield, avoids generation of impurities, and provides a qualified reference substance for quality control of levonorgestrel.

Preparative chemical methods for aromatization of 19-nor-Δ4-3-oxosteroids

Two preparative chemical methods for aromatization of 19-nor-Δ4-3-oxosteroids are described.The first method consists of an oxidative aromatization of 19-nor-Δ4-3-oxosteroids with iodine-ceric ammonium nitrate in methanol to give a mixture of 3-methoxy ring-A aromatized derivatives consisting of the desired product, the Δ9,11 derivative, the 6-oxo derivative as well as some ring-A iodinated material.Conversion of this material to a mixture of the 3-methoxy ring-A aromatized derivative and its 6-oxo derivative was achieved by catalytic hydrogenation.Finally, reduction of the 6-oxo function with triethylsilane in trifluoroacetic acid gave the 3-methoxy-17-trifluoroacetate ring-A aromatized derivative as a single product.In the second method, reaction of 19-nor-Δ4-3-oxosteroids with copper(II) bromide in acetonitrile at room temperature resulted in aromatic steroids in a single step in excellent yields.The second method was used in the first practical chemical synthesis of a 6-dehydroestrogen from a 19-nor-Δ4,6-3-oxosteroid. - Keywords: copper(II) bromide; ceric ammonium nitrate; iodine; aromatization; 19-nor-Δ4-3-oxosteroids

TOTALLY SYNTHETIC -13-ALKYL-3-HYDROXY AND

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