22256-03-7

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 3,17-Dioxo-4-androsten-19-oate is used as a pharmaceutical compound for its potential role in the development of treatments targeting aromatase, an enzyme involved in the synthesis of estrogen. Its analog nature allows for the exploration of its effects on the enzyme, potentially leading to the creation of new drugs for hormone-related conditions.
Used in Research and Development:
In the field of research and development, Methyl 3,17-Dioxo-4-androsten-19-oate serves as a valuable compound for studying the structure and function of aromatase and its role in various biological processes. Its use in research can contribute to a better understanding of hormone regulation and the development of novel therapeutic strategies.
Used in Chemical Synthesis:
Methyl 3,17-Dioxo-4-androsten-19-oate can be utilized as a starting material or intermediate in the synthesis of other steroidal compounds and derivatives. Its unique structure makes it a potentially useful building block for the creation of new molecules with specific biological activities or properties.

InChI:InChI=1/C20H26O4/c1-19-9-8-16-14(15(19)5-6-17(19)22)4-3-12-11-13(21)7-10-20(12,16)18(23)24-2/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,19-,20+/m0/s1

Upstream product

• 111099-43-5 10β-(Z- and E-2-methoxyethylene)estr-4-ene-3,17-dione 
• 111099-45-7 (8R,9S,10S,13S,14S)-10-(Hydroperoxy-methoxy-methyl)-13-methyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione 
• 186581-53-3 diazomethane 
• 4757-95-3 androst-4-ene-3,17-dion-19-oic acid 
• 968-49-0 19-oxoandrostenedione 
• 510-64-5 19-hydroxy-4-androstene-3,17-dione 

Relevant academic research and scientific papers

Synthesis and Study of a Methoxyhydroperoxide-Androstenedione Derivative; Analogue of a Potential Aromatase Intermediate

A methoxyhydroperoxide analogue (12) to a proposed aromatase intermediate has been synthesized by ozonolysis of metoxyvinyl compound (7) in the presence of methanol; it has been shown not to produce estrone with or without acetylation, but the free hydroperoxide apparently undergoes a facile, stereospecific intramolecular epoxidation.

Steroid dimer formation: Metal reduction of methyl androst-4-ene-3,17-dion-19-oate

Two isomeric dimeric steroids, 3,3'-bis(methyl 3-hydroxyandrost-4-en-17-on-19-oate-3-yl), with symmetrical (α,α') and unsymmetrical structures (α,β'), have been obtained by reduction of methyl androst-4-ene-3,17-dion-19-oate with zinc in aqueous acetic acid together with the major products, the isomeric methyl 5α- and 5β-androst-3-en-17-on-19-oates. The structures of the dimers and unsaturated products are supported by spectroscopic methods. The symmetrical dimer was also obtained from treatment of the 4-en-3-on-19-oate ester with lithium in ammonia. Copyright (C) 2000 Elsevier Science Inc.

Synthesis of and Reactivity Studies with 19-Peroxide-Androstenedione Derivatives: Analogues of a Proposed Aromatase Intermediate

Human placental aromatase is a cytochrome P 450 enzyme system which converts steroidal androgens to steroidal estrogens.Three sequential oxidative steps are involved in the conversion, the first two leading to 19-hydroxy (2) and 19-oxo intermediates (3), respectively.The mechanism of the third step has remained elusive although one proposal which has remained consistent with experimental data involves formation and aromatization of a 19,19-hydroxyferric peroxide (5) intermediate.This study discusses the synthesis of 19,19-methoxy hydroperoxide (12) via ozonolysis, evidence for its formation, and studies of its reactivity under different conditions.Another approach was used to synthesize 19,19-hydroxy peroxide derivatives via the 19-aldehyde (3b).The reactivity of these derivatives was also explored.An analogous reaction involving 18O-HOOH was carried out to investigate the mechanistic details of an unprecedented intramolecular epoxidation reaction.None of the peroxide derivatives were converted into estrogen or estrogen derivatives under the conditions examined, and the possible implications for the aromatase reaction are discussed.