19037-28-6

Basic information

• Product Name: 5-Pregnene-3alpha-ol-20-one
• Synonyms: 5-Pregnene-3alpha-ol-20-one;(3α)-3-Hydroxypregn-5-en-20-one;3-epi-Pregnenolone;3α-Hydroxy-20-oxopregn-5-ene;Pregn-5-en-3α-ol-20-one
• CAS NO: 19037-28-6
• Molecular Formula: C₂₁H₃₂O₂
• Molecular Weight: 316.47758
• Mol File: 19037-28-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 443.3°Cat760mmHg
• Flash Point: 188.9°C
• Appearance: /
• Density: 1.09g/cm³
• Vapor Pressure: 1.02E-09mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 5-Pregnene-3alpha-ol-20-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Pregnene-3alpha-ol-20-one(19037-28-6)
• EPA Substance Registry System: 5-Pregnene-3alpha-ol-20-one(19037-28-6)

Safety Data

• Hazardous Substances Data: 19037-28-6(Hazardous Substances Data)

Usage

Uses

An epimer of Pregnenolone (P712200), a GABAA antagonist and increases neurogenesis in the hippocampus.

InChI:InChI=1/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16+,17-,18+,19+,20+,21-/m1/s1

Upstream product

• 64-17-5 ethanol 
• 1236-09-5 pregn-5-ene-3,20-dione 
• 5223-98-3 3β-hydroxyl-5-pregnen-20-one acetate 
• 38759-50-1 3β-methanesulfonyloxypregn-5-en-20-one 
• 387-79-1 17-Hydroxypregnenolone 
• 1093959-59-1 3β-hydroxypregn-5-en-20-one-3-acetate 
• 979-02-2 16-dehydropregnenolone acetate 

Downstream Products

• 2862-58-0 (S)-17-Ethyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol 
• 1778-02-5 Pregnenolone acetate 
• 145-13-1 Pregnenolone 
• 302-97-6 androst-4-en-3-one-17β-carboxylic acid 
• 57-83-0 progesterone 
• 1164-98-3 3β-21-Dihydroxy-5-pregnen-20-one 
• 91414-17-4 3β-hydroxy-20-phenylselenopregna-5,17-diene 
• 566-65-4 dihydroprogesterone 
• 53-43-0 dehydroepiandrosterone 
• 1232-18-4 17-Ethyl-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one 
• 24199-63-1 {4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-acetic acid (3S,8S,9S,10R,13S,14S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 

Relevant articles and documents

Design, synthesis, and biological evaluation of novel androst-17β-amide structurally related compounds as dual 5α-reductase inhibitors and androgen receptor antagonists

Prostate cancer (PCa) is the second leading cause of death in men. Apart from androgen receptor, 5α-reductase has also been recognized as a potential target. In this study, a series of androst-17β-amide compounds have been designed and synthesized targeting both AR and 5α-reductase. Their anti-proliferation activities were evaluated in AR + cell line 22RV1 and AR ? cell line PC-3. The results indicated that most of the synthesized compounds inhibited the testosterone-stimulated cell proliferation with good selectivity and safety. Among all the compounds, androst[3,2-c]pyrazole derivatives (9a–9d) displayed the best inhibition activity comparable with flutamide. Moreover, most of the synthesized compounds displayed good 5α-reductase inhibitory activities with IC50 lower than 1 μM. The docking result of 9d-AR indicated that AR was forced to expands its binding cavity and maintain an antagonistic conformation since the steric hindrance of 9d impeded H12 transposition. Overall, compound 9d can be identified as a potential dual 5α-reductase inhibitor and AR antagonist, which might be of therapeutic importance for PCa treatment.

Steroid compound 3-site hydroxyl configuration inversion method

The invention discloses a steroid compound 3-site hydroxyl configuration inversion method. The method specifically comprises the following steps that (1) a steroid compound containing a 3-site hydroxyl reacts with an acyl chloride compound; (2) the product obtained in the step (1) and a substituting agent are subjected to SN2 nucleophilic substitution reaction under existing of a phase transfer catalyst; and (3) the product obtained in the step (2) is subjected to a hydrolysis reaction. Compared with a Mitsunobu method, the method does not need to use triphenylphosphine and azodiformate pricedhigher, and accordingly the production cost is greatly lowered; meanwhile, a p-nitrobenzoic acid derivative which seriously affects the water environment does not need to be used, and therefore the method is more environmentally friendly. The method adopts cesium acetate/18-crown ether-6 system to conduct 3-site hydroxyl configuration inversion, can remarkably reduce occurrence of side reactions,accordingly a higher reaction yield is obtained, and the method is finally applicable to industrialized production.

Stereochemistry of tritium at carbon 15 in cholesterol derived from (3R,2R)-2T-mevalonic acid in rat livers.

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