53906-49-3

Basic information

• Product Name: (3β,20S)-20-Formyl-3-hydroxy-5-pregnene
• Synonyms: (3β,20S)-20-Formyl-3-hydroxy-5-pregnene;(3β,20S)-3-Hydroxy-pregn-5-ene-20-carboxaldehyde;(2S)-2-[(3S,8S,9S,10R,13S,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]propanal
• CAS NO: 53906-49-3
• Molecular Formula: C₂₂H₃₄O₂
• Molecular Weight: 330.50416
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 53906-49-3.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3β,20S)-20-Formyl-3-hydroxy-5-pregnene(CAS DataBase Reference)
• NIST Chemistry Reference: (3β,20S)-20-Formyl-3-hydroxy-5-pregnene(53906-49-3)
• EPA Substance Registry System: (3β,20S)-20-Formyl-3-hydroxy-5-pregnene(53906-49-3)

Safety Data

• Hazardous Substances Data: 53906-49-3(Hazardous Substances Data)

Usage

Description

(3β,20S)-20-Formyl-3-hydroxy-5-pregnene is a steroidal compound derived from the pregnene family, characterized by its unique molecular structure with a formyl group at the 20th position and a hydroxyl group at the 3rd position. It exhibits significant biological activities and has been a subject of interest in pharmaceutical research due to its potential therapeutic applications.

Uses

Used in Pharmaceutical Research:
(3β,20S)-20-Formyl-3-hydroxy-5-pregnene is used as a research compound for the development of novel anti-parasitic agents. Its potential as an anti-trypanosomal and anti-leishmanial agent makes it a valuable candidate for combating tropical diseases such as Chagas disease and leishmaniasis, which are caused by Trypanosoma and Leishmania parasites, respectively.
Used in Anthelmintic Applications:
In addition to its anti-parasitic properties, (3β,20S)-20-Formyl-3-hydroxy-5-pregnene may also be utilized as an anthelmintic agent, targeting various helminth parasites that cause infections in humans and animals. Its effectiveness against these parasites could lead to the development of new treatments for helminthic infections.
Used in Steroid Synthesis:
Due to its structural features, (3β,20S)-20-Formyl-3-hydroxy-5-pregnene can be employed as a key intermediate in the synthesis of various steroidal compounds with diverse biological activities. Its use in this capacity can contribute to the development of new drugs with applications in different therapeutic areas, such as hormonal regulation, inflammation, and immune response modulation.

Upstream product

• 83-48-7 24ξ-24-ethylcholest-5,22-dien-3β-ol 
• 32212-73-0 5α,6β-dibromostigmastan-3β-yl acetate 
• 4651-48-3 stigmasterol acetate 
• 145-13-1 Pregnenolone 
• 287471-28-7 stigmast-4,22-dien-3β-(2-tetrahydropyranyl)ether 
• 83-48-7 Stigmasterol 
• 1474-14-2 3β-acetoxybisnor-5-cholenic acid 
• 55509-37-0 3β-acetoxy-23,24-bisnor-chol-5-en-22-ol 
• 497841-91-5 5α,6β-dibromostigmast-22-en-3β-(2-tetrahydropyranyl)ether 
• 86400-70-6 (3S,8S,9S,10R,13S,14S,17S)-10,13-Dimethyl-17-[(E)-1-methyl-2-(2-trimethylsilanyl-ethoxy)-vinyl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol 
• 86400-71-7 (3S,8S,9S,10R,13S,14S,17S)-10,13-Dimethyl-17-[(Z)-1-methyl-2-(2-trimethylsilanyl-ethoxy)-vinyl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol 
• 10211-88-8 (20S)-3β-acetoxybisnorchol-5-en-22-al 
• 83-48-7 stigmasterol 

Downstream Products

• 26033-10-3 E/Z-cholesta-5,22-dien-3β-ol 
• 35882-85-0 26,27-dinorergost-5-ene-3β,24-diol 
• 333973-17-4 (2R,4S,5S)-5-[(3S,8S,9S,10R,13S,14S,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-ethyl-4-(imidazole-1-carbothioyloxy)-hexanoic acid ethyl ester 
• 333972-96-6 (4S,5S)-4-Benzyloxy-5-[(3S,8S,9S,10R,13S,14S,17R)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylene-hexanoic acid ethyl ester 
• 333972-97-7 (4R,5S)-4-Benzyloxy-5-[(3S,8S,9S,10R,13S,14S,17R)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylene-hexanoic acid ethyl ester 

Relevant articles and documents

Sterol compound and its pharmaceutically acceptable salt or prodrug, and application thereof

The present invention discloses a sterol compound and its pharmaceutically acceptable salt or prodrug, and an application thereof in the prevention or treatment of malignant tumors associated with LXR. The compound has an inhibitory ability against various malignant tumors in in-vitro experiments, and also has an inhibitory ability against malignant tumors malignant tumors in in-vivo experiments.The sterol skeleton compound has the equivalent curative effect on the malignant tumors with cytotoxic drugs currently used for treating the tumors, and has the same therapeutic effect with positive drugs for evaluating the drug effect of the compound. The compound has the advantages of good antitumor activity, good safety, no side effects caused by the positive drugs, and facilitation of enhancement of the immune function of animals. The sterol compound has a potential to become a safe and effective broad-spectrum antitumor drug.

3beta-hydroxy-ergosta-5-ene steroid derivative and drug application thereof

The invention provides a structure of a 3beta-hydroxy-ergosta-5-ene steroid compound, and applications of the compound and the pharmaceutically acceptable form of chemical protection or a prodrug in the preparation of drugs capable of preventing or treating LXRbeta related metabolic syndromes. The LXRbeta related metabolic syndromes include hyperlipidemia, atherosclerosis or hypertension. Throughthe discovery of the evaluation of lipid-lowering activity in animal bodies, the compound has obvious effects on lipid lowering, so that the compound has potentials of further developing into a novellipid-lowering drug.

Novel method used for synthesizing cholesterol

The invention discloses a novel method used for synthesizing cholesterol. The novel method comprises following steps: 1, stigmasterol 02 is dissolved in an organic solvent I, and is subjected to silicon etherification reaction with trimethylchlorosilane under the effect of a catalyst, and a compound 03 is obtained via water washing and condensation; 2, the compound 03 is dissolved in an organic solvent II for ozone oxidation, zinc powder and acetate acid gracial are added for reduction, after reduction, filtering, washing, and condensation are carried out so as to obtain a compound 04; 3, triphenylphosphine is reacted with 1-halogenated-3-methyl butane so as to obtain 3-methyl butyl triphenyl halogenated phosphorus, the 3-methyl butyl triphenyl halogenated phosphorus is added into an aprotic solvent, a strong base is added, wittig reaction with a compound 4 is carried out, and neutralizing, condensation, and filtering are carried out so as to obtain a compound 05; 4, the compound 05 is subjected to selective hydrogenation in a solvent III under the action of a catalyst and a passivator, and filtering, condensation, and crystallization are carried out so as to obtain cholesterol 01. The novel method is simple; raw materials are cheap; the novel method is economic and is friendly to the environment, and is convenient for industrialized production.