15375-21-0

Basic information

• Product Name: 1,4,9-Androstatriene-3-17-dione
• Synonyms: 1,4,9-Androstatriene-3-17-dione
• CAS NO: 15375-21-0
• Molecular Formula: C₁₉H₂₂O₂
• Molecular Weight: 283.38472
• EINECS: 433-560-3
• Mol File: 15375-21-0.mol

Chemical Properties

• Melting Point: 164-166 °C(Solv: ethyl acetate (141-78-6))
• Boiling Point: 454.188°C at 760 mmHg
• Flash Point: 169.149°C
• Appearance: /
• Density: 1.168g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.588
• CAS DataBase Reference: 1,4,9-Androstatriene-3-17-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4,9-Androstatriene-3-17-dione(15375-21-0)
• EPA Substance Registry System: 1,4,9-Androstatriene-3-17-dione(15375-21-0)

Safety Data

• Hazardous Substances Data: 15375-21-0(Hazardous Substances Data)

Usage

Uses

Used in Bodybuilding and Athletics:
1,4,9-Androstatriene-3,17-dione is used as a performance-enhancing drug in bodybuilding and athletics for its ability to increase testosterone levels. The elevated testosterone levels are thought to contribute to enhanced athletic performance and muscle building. However, due to its controversial nature and potential health risks, it is banned by many athletic organizations and should be used with caution and under the guidance of a medical professional.
Used in Pharmaceutical Research:
While not explicitly mentioned in the provided materials, the compound's role as an aromatase inhibitor could also make it a subject of interest in pharmaceutical research. Researchers may explore its potential applications in the development of treatments for conditions related to hormonal imbalances or in the management of certain diseases where hormonal regulation is a factor. However, further research and clinical trials would be necessary to establish its safety and efficacy in such applications.

InChI:InChI=1/C19H22O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h7-9,11,14-15H,3-6,10H2,1-2H3/t14-,15-,18-,19-/m0/s1

Upstream product

• 898-84-0 (8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-6H-cyclopenta[a]phenanthrene-3,17-dione 
• 109-92-2 ethyl vinyl ether 
• 898-84-0 11α-hydroxy-androsta-1,4-diene-3,17-dione 

Downstream Products

• 105141-33-1 3-<5-Oxo-2-phenyl-1,3-oxazol-4(5H)-yliden>-1,4,9(11)-androstatrien-17-on 
• 910-99-6 17α,21-dihydroxy-16β-methyl-1,4,9(11)-pregnatriene-3,20-dione 21-acetate 
• 38680-83-0 21-acetyloxy-9β,11β-epoxy-17α-hydroxy-1,4-diene-3,20-dione 
• 13649-57-5 21-Deacetyldeflazacort 
• 14484-47-0 deflazacort 
• 37413-91-5 2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate 
• 37927-29-0 (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 0^2,7. 0^11,15]heptadeca-3,6-diene-14-carboxylic acid 
• 898-84-0 (8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-6H-cyclopenta[a]phenanthrene-3,17-dione 
• 791-69-5 9⁽¹¹⁾-Dehydroestradiol 
• 50-28-2 estradiol 

Relevant articles and documents

A concise effective deprotection of spiro 3-cyclic thiaza ketal of steroidal 1,4-dien-3-one

An effective deprotective method of spiro 3-cyclic thiaza ketal of steroidal 1,4-dien-3-ones using alkyl vinyl ether in the presence of protic acid followed by the treatment of aqueous alkali was described. This novel protocol could be fulfilled under mild condition with high yield. The mechanism mediated by a carbonium ion formed in situ was clarified by the capture of the cleaved fragment.

Preparation method of loteprednol etabonate intermediate

The invention provides a preparation method of a loteprednol etabonate intermediate. The preparation method comprises the following steps: carrying out dehydration reaction on 11 alpha-hydroxyl-ADD and a dehydrating agent in an organic solvent to obtain a compound II; carrying out a first addition reaction on the compound II and a halogenating reagent in an organic solvent in the presence of an acid catalyst, and adding a quenching agent to carry out a quenching reaction after the reaction is finished, so as to obtain a compound III; carrying out reduction reaction on the compound III and a metal reducing agent in an organic solvent in the presence of an acid catalyst to obtain a compound IV; carrying out secondary addition reaction on the compound IV and a cyaniding reagent in an organic solvent in the presence of a basic catalyst to obtain a compound V; and carrying out hydrolysis reaction on thecompound V and an acid reagent in an organic solvent to obtain a compound VI, wherein the compound VI is the loteprednol etabonate intermediate. The preparation method saves energy, reduces consumption, and is easy to operate, high in yield and good in purity.

Synthesis method of loteprednol intermediate

The invention provides a preparation method of a loteprednol etabonate intermediate, wherein the method comprises that cheap and accessible 11 alpha-hydroxy-ADD as a starting raw material is subjectedto dehydrating, Grignard reaction, hydrolyzing, oxidizing, bromo-hydroxylating and reducing to obtain 17 beta-carboxylic acid (compound VII). The method has the advantages of easily available initialraw materials, high yield, good purity and stable process.

Preparation method of deflazacort

The present invention relates to a preparation method of deflazacort. The deflazacort is prepared through the following thirteen chemical synthesis reactions of elimination, cyanohydrintion, silanization, translocation and esterification, elimination, epoxidation, protection, ammoniation, cyclization, hydrolysis, bromo hydroxylation, debromination, esterification and the like. Raw materials for the preparation method of deflazacort are easily obtained. Meanwhile, the preparation method of deflazacort is mild in reaction condition, simple in process route and low in pollution, thus having a good application prospect.

A process for the preparation of intermediates fluocinone acetate

The invention discloses a preparation method for a fluocinolone acetonide midbody, i.e., 21-acetate-9,11-epoxy-17-alpha-hydroxypregn-1,4-diene-3,20-diketone. A compound I, i.e., 11-alpha-hydroxy-ADD (androstadienedione), serves as a starting material; an elimination reaction, a cyano-substitution reaction, a siloxy protective reaction, an intramolecular nucleophilic substitution reaction, a bromo-epoxy reaction and a replacement reaction are carried out to obtain the fluocinolone acetonide midbody. The preparation method provided by the invention has the advantages that the starting material which is relatively cheap is used, the reactions in the steps are relatively easy to implement, and the yield is higher, so that the production is more economical and safe, and higher applicability for industrial production is achieved; through route design optimization, the preparation method avoids 9 (11)-double-bonded epoxidation with the existence of 21-acetate in the traditional technique, so as to avoid the 21-acetate hydrolysis, greatly improve the quality and yield of the fluocinolone acetonide midbody, and reduce the entire production cost.