53-42-9

Basic information

• Product Name: Etiocholanone
• Synonyms: 5β-Androsterone;3alpha-Hydroxyetiocholan-17-one;C04373;ETIOCHOLANOLONE(RG);Etiocholan-3α-ol-17-one,3α-Hydroxy-5β-androstan-17-one, 5β-Androsterone, Etiocholanone;3α-Etiocholanolone;3α-Hydroxy-5β-androstane-17-one;5β-Androstane-3α-ol-17-one
• CAS NO: 53-42-9
• Molecular Formula: C₁₉H₃₀O₂
• Molecular Weight: 290.44
• EINECS: 200-835-2
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Steroids;Steroids & Hormones - 13C & 2H
• Mol File: 53-42-9.mol
• Article Data: 23

Chemical Properties

• Melting Point: 148～150℃
• Boiling Point: 392.52°C (rough estimate)
• Flash Point: 2℃
• Appearance: /
• Density: 0.9731 (rough estimate)
• Vapor Pressure: 1.5E-08mmHg at 25°C
• Refractive Index: 1.5360 (estimate)
• Storage Temp.: 2-8°C
• PKA: 15.14±0.60(Predicted)
• Water Solubility: 20.33mg/L(25 oC)
• BRN: 2217625
• CAS DataBase Reference: Etiocholanone(CAS DataBase Reference)
• NIST Chemistry Reference: Etiocholanone(53-42-9)
• EPA Substance Registry System: Etiocholanone(53-42-9)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36
• Safety Statements: 16-36/37
• RIDADR: UN 1648 3 / PGII
• WGK Germany: 3
• Hazardous Substances Data: 53-42-9(Hazardous Substances Data)

Usage

Description

Etiocholanone, also known as 5β-Androsterone, is an androstanoid that is 5β-androstane substituted by an alpha-hydroxy group at position 3 and an oxo group at position 17. It is a metabolite of testosterone in mammals and exhibits weak estrogenic action.

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

• 53-43-0 dehydroepiandrosterone 
• 57-83-0 Progesterone 
• 63-05-8 Androstenedione 
• 1229-12-5 androstane-3,17-dione 
• 1192475-82-3 androstendione 
• 19325-01-0 C₂₁H₃₄OS₂ 
• 571-20-0 (3S,5S,10S,13S)-10,13-Dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,17-diol 
• 571-20-0 (5α)-androstane-3β,17β-diol 
• 897-06-3 Androsta-1,4-diene-3,17-dione 
• 1044-89-9 androst-4-ene-3-one-17-ethylene ketal 
• 38394-98-8 17α-cyano-17β-hydroxyandrost-4-en-3-one 
• 77881-13-1 17β-cyano-17α-hydroxy-4-androsten-3-one 
• 58-22-0 testosterone 
• 1098-45-9 5β-pregnane-3α,17α,20β-tetraol 

Downstream Products

• 154229-26-2 17-(3-pyridyl)-5β-androsta-16-ene-3-one 
• 1940176-03-3 17-(3-pyridyl)-5β-androsta-16-ene-3α-ol 
• 154229-25-1 17-(3-pyridyl)-5α-androsta-16-ene-3α-ol 
• 571-20-0 (5α)-androstane-3β,17β-diol 
• 3602-09-3 Etiocholanolone-3-glucuronide 
• 57305-19-8 C₂₅H₄₆O₂Si₂ 
• 2061-71-4 3α-hydroxy-17a-oxa-D-homo-5α-androstan-17-one 

Relevant articles and documents

An Easy Determination of Epimeric Androsterones by Collision Spectroscopy: the Molar Ratio of 5β-androstan-3α-ol-17-one and 5β-androstan-3β-ol-17-one Obtained by Hydrogenation of 5β-androstan-3,17-dione on Cu/Al2O3

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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.

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.