53-42-9

Usage

Uses

Used in Pharmaceutical Industry:
Etiocholanone is used as a pharmaceutical compound for its weak estrogenic action. It serves as a metabolite of testosterone, which can be utilized in the development of medications targeting hormonal imbalances or related conditions.
Used in Research and Development:
In the field of research and development, Etiocholanone is used as a reference compound for studying the effects of testosterone metabolites on various biological processes. Its weak estrogenic action makes it a valuable tool for understanding the complex interactions between hormones and their impact on the body.
Used in Hormone Replacement Therapy:
Etiocholanone, due to its weak estrogenic properties, can be used as a component in hormone replacement therapy. It may help in addressing specific hormonal deficiencies or imbalances in patients requiring such treatment.
Used in Sports Medicine:
As a metabolite of testosterone, Etiocholanone may be utilized in sports medicine to study the effects of testosterone on athletic performance and muscle development. This can contribute to the development of strategies for enhancing athletic performance while adhering to anti-doping regulations.
Used in Analytical Chemistry:
In analytical chemistry, Etiocholanone can be employed as a reference material for the development and validation of analytical methods for the detection and quantification of testosterone metabolites in biological samples. This is crucial for ensuring the accuracy and reliability of hormone level measurements in various applications, such as doping control or clinical diagnostics.

InChI:InChI=1/C19H30O2/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/h12-16,20H,3-11H2,1-2H3/t12-,13-,14+,15+,16?,18+,19+/m1/s1

Upstream product

• 571-20-0 (3S,5S,10S,13S)-10,13-Dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,17-diol 
• 19325-01-0 C₂₁H₃₄OS₂ 
• 1192475-82-3 androstendione 
• 57711-44-1 Androsterone-dimethyl-tert.-butylsilyl-ether 
• 53-43-0 dehydroepiandrosterone 
• 1229-12-5 androstane-3,17-dione 
• 1098-45-9 5β-pregnane-3α,17α,20β-tetraol 
• 546-67-8 lead(IV) tetraacetate 
• 64-19-7 acetic acid 
• 57-83-0 Progesterone 
• 63-05-8 Androstenedione 
• 58-22-0 testosterone 
• 77881-13-1 17β-cyano-17α-hydroxy-4-androsten-3-one 
• 38394-98-8 17α-cyano-17β-hydroxyandrost-4-en-3-one 

Downstream Products

• 846-46-8 androstanedione 
• 1229-12-5 androstane-3,17-dione 
• 571-20-0 5β-androstane-3α,17β-diol 
• 5856-10-0 5beta-Androstane-3alpha,17alpha-diol 
• 1224-92-6 5beta-Androstan-3alpha-ol 
• 1235-97-8 17α-ethylandrost-4-en-17β-ol-3-one 
• 4589-93-9 3α-hydroxy-5β-androstan-17-one-(2,4-dinitro-phenylhydrazone) 
• 18453-92-4 3α-hydroxy-5β-androstane-16,17-dione-16-(Ξ)-oxime 
• 3602-09-3 Etiocholanolone-3-glucuronide 
• 571-20-0 (5α)-androstane-3β,17β-diol 

Relevant academic research and scientific papers

Catalytic removal of tert-butyldimethylsilyl (TBS) ether by PVP-I

A mild, efficient and rapid protocol the deprotection of alcoholic TBDMS ethers using PVP-1 as catalyst in methanol, the procedure of deprotection of various TBDMS ethers were found to be very convenient, easy work-up, high yielding.

Stereo selective one-step reduction in the steroid skeleton 4 - ene -3 - ketone as a 3 α - hydroxy - 5 β - hydrogen A/B cis structure method

The invention relates to a method for one-step reduction of a 4-ene-3-one structure in a steroid skeleton into an A/B cis-3a-hydroxy-5b-hydrogen structure, belonging to the fields of organic chemistry and drug synthesis. According to the method, under the conditions of room temperature and an environment of absolute ethyl alcohol, cuprous chloride is used as a catalyst and sodium borohydride is used as a reducing agent for high-selectivity conversion of the 4-ene-3-one structure of 4-AD, ADD and derivatives thereof into the A/B cis-3a-hydroxy-5b-hydrogen structure. According to results of X-diffraction results, an androstane-3a-hydroxy-5b-hydrogen-17-one product prepared by using the method has a stereo structure; reaction conditions are mild and simple; used reagents are cheap and easily available; operation is convenient; good repeatability is realized, and high yield is obtained. The method provided by the invention lays a good foundation for exploitation of resourceful utilization of sterol and for research on synthesis of drugs like ursodesoxycholic acid, chenodeoxycholic acid, deoxycholic acid and ecdyson with the A/B cis-structure with non-cholic acid type steroids as raw materials.

The regio- and stereo-selective reduction of steroidal 4-en-3-ones using Na2S2O4/NaHCO3 and CuCl/NaBH 4

This paper describes the regio- and stereoselective reduction of a.

Substrate specificity of a mouse aldo-keto reductase (AKR1C12)

AKR1C12, a mouse member of the aldo-keto reductase (AKR) superfamily, is highly expressed in the stomach and is identical to a protein encoded in an interleukin-3-regulated gene in mouse myeloid cells, but its function remains unknown. In this study, the recombinant AKR1C12 was purified to homogeneity and the specificity for coenzymes and substrates was examined at a physiological pH of 7.4. The enzyme reduced various α-dicarbonyl compounds, several ketosteroids, aldehydes and some ketones using NADH as the preferred coenzyme. In the reverse reaction, the enzyme showed coenzyme preference for NAD +, and oxidized 3α-, 17β- and 20α-hydroxysteroids, and non-steroidal aliphatic and alicyclic alcohols, of which many hydroxysteroids and geranylgeraniol were good substrates, exhibiting low K m and high kcat/Km values. The results, together with the intracellular high ratio of NAD+/NADH, suggest that AKR1C12 functions as a dehydrogenase for the endogenous hydroxysteroids and geranylgeraniol in mouse stomach and myeloid cells.

Phosphine effects in the copper(I) hydride-catalyzed hydrogenation of ketones and regioselective 1,2-reduction of α,β-unsaturated ketones and aldehydes. Hydrogenation of decalin and steroidal ketones and enones

The stereoselectivity and regioselectivity of the catalytic hydrogenation of ketones and α,β-unsaturated ketones and aldehydes using soluble copper(I) hydride catalysts have been investigated as a function of the ancillary phosphine ligand. While a relatively narrow range of aryldialkylphosphine ligands produce active hydrogenation catalysts, some ligands provide higher selectivity for 1,2-reduction of acyclic unsaturated carbonyl substrates than observed using the previously reported dimethylphenylphosphine-stabilized catalyst. The synthetic utility of this class of hydridic hydrogenation catalysts is illustrated by the hydrogenation of decalin and steroidal ketones and enones, the latter giving allylic alcohols with high selectivity. (C) 2000 Elsevier Science Ltd.

Steroid transformations with Exophiala jeanselmei var. lecanii-corni and Ceratocystis paradoxa

The fungi Exophiala jeanselmei var. lecanii-corni [IMI (International Mycological Institute) 312989, UAMH (University of Alberta Microfungus Collection and Herbarium) 8783] and Ceratocystis paradoxa (IMI 374529, UAMH 8784) have been examined for their potential in steroid biotransformation. The study has determined that E. jeanselmei var. lecanii-corni effected overall anti-Markovnikov hydration on dehydroisoandrosterone, and side-chain degradation on a variety of pregnanes. Both ascomycetes were found to carry out redox reactions of alcohols and ketones as well as 1,4 reduction of α,β-unsaturated carbonyl systems.

Microbial transformations of testosterone to 5α-dihydrotestosterone by two species of Penicillium: P. chrysogenum and P. crustosum

Two species of Penicillium - P. chrysogenum and P. crustosum - were cultured in presence of [3H]testosterone as a substrate. Both species were shown to reduce the 4,5-double bond in testosterone to give dihydrotestosterone (DHT). The steroids produced were 5α- dihydrotestosterone, DHT, 3α-hydroxy-5β-androstan-17-one, 3α-hydroxy-5α- androstan-17-one, 4-androstene-3,17-dione, and 5α-androstane-3,17-dione. These products implicate the presence of the 5α-reductase, with maximal activity at pH 6 and 8, in both species of Penicillium. The presence of DHT in the growth medium and not in the mycelium suggests that DHT is excreted into the medium.

Heterogeneous Catalysis in Carbonyl Regeneration from 1,3-Dithiolanes and 1,3-Dithianes by Zirconium Sulfophenyl Phosphonate

Layered zirconium sulfophenyl phosphonate was found to be an efficient heterogeneous catalyst for mild hydrolysis of 1,2 dithiolanes and 1,3 dithianes to their corresponding carbonyl compounds.

A New Procedure for Dethioacetalization via Equilibrium Exchange with Aqueous Acetone, Paraformaldehyde and Amberlyst 15 as Acidic Catalyst

Carbonyl compounds were regenerated from corresponding Ethanediyl S,S-Acetals via equilibrium exchange with aqueous acetone, paraformaldehyde and Amberlyst 15, as acidic catalyst, at 80 deg C.