40736-33-2

Basic information

• Product Name: 3-keto-23,24-bisnorchol-4-en-22-ol
• Synonyms: 3-keto-23,24-bisnorchol-4-en-22-ol;(20S)-21-Hydroxy-20-Methylpregn-4-en-3-one;23,24-Bisnorchol-4-en-3-on-22-ol
• CAS NO: 40736-33-2
• Molecular Formula: C₂₂H₃₄O₂
• Molecular Weight: 330.50416
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals, Steroids
• Mol File: 40736-33-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 178-180 °C
• Boiling Point: 464.1±14.0 °C(Predicted)
• Appearance: /
• Density: 1.07±0.1 g/cm3(Predicted)
• PKA: 14.97±0.10(Predicted)
• CAS DataBase Reference: 3-keto-23,24-bisnorchol-4-en-22-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-keto-23,24-bisnorchol-4-en-22-ol(40736-33-2)
• EPA Substance Registry System: 3-keto-23,24-bisnorchol-4-en-22-ol(40736-33-2)

Safety Data

• Hazardous Substances Data: 40736-33-2(Hazardous Substances Data)

Usage

Uses

(20S)-21-Hydroxy-20-methylpregn-4-en-3-one is a side chain degradation product of natural sterols. It is also an intermediate in the preparation of follicular fluid-meiosis activating sterol.

Upstream product

• 83-46-5 β-sitosterol 
• 57-87-4 Ergosterol 
• 57-88-5 cholesterol 
• 474-62-4 Campesterol 

Downstream Products

• 356063-47-3 (20S)-20-[((triisopropylsilyl)oxy)methyl]-pregna-4-en-3-one 
• 1715-86-2 cholesta-5,7,24-triene-3β-ol 
• 74996-92-2 22-Chlor-23,24-dinorchol-5-en-3β-yl-ethanoat 
• 87080-70-4 22-Chlor-5α,8α-(4-phenyl-1,2-urazolo)-23,24-dinorchol-6-en-3β-ol 
• 87080-74-8 3β-((tert-butyldimethylsilyl)oxy)-22-tosyloxy-23,24-bisn-orchol-5,7-dien 
• 87171-95-7 3β-acetoxy-22-iodo-5α,8α-(4-phenyl-1,2,4-triazolidine-3,5-dione-1,2-diyl)-23,24-bisnorchol-6-ene 
• 87080-69-1 22-Chlor-5α,8α-(4-phenyl-1,2-urazolo)-23,24-dinorchol-6-en-3β-yl-ethanoat 
• 87080-71-5 3β-(tert-Butyldimethylsilyloxy)-22-chlor-5α,8α-(4-phenyl-1,2-urazolo)-23,24-dinorchol-6-en 
• 128-13-2 ursodeoxycholic acid 
• 2309-32-2 3-acetoxy-cholesta-3,5-diene 
• 80-97-7 Cholestanol 
• 80-97-7 Coprostanol 
• 604-35-3 Cholesteryl acetate 
• 1059-85-4 3-epicholesteryl acetate 

Relevant articles and documents

Microbial side-chain degradation of ergosterol and its 3-substituted derivatives: A new route for obtaining of deltanoids

The strain of Mycobacterium sp. VKM Ac-1815D was found to convert ergosterol and its 3-acetate mainly to androst-4-ene-3,17-dione (AD) thus demonstrating ability to reduce 7(8)-double bond and hydrolyze sterol ester in addition to oxidation of 3β-hydroxy group,δ5-δ4 isomerization and side-chain degradation. Ergosterol bioconversion in the presence of isoflavones and ions of some bivalent metals known inhibitors of 3-hydroxysteroid dehydrogenase, did not alter products composition. Protection of ergosterol 3β-hydroxyl with methoxymethyl group allowed the formation of bioconversion products retaining the δ 5,7-configuration. The major product was identified by mass-spectrometry and proton NMR as 3- methoxymethoxy-androsta-5,7-diene-17-one (MA). TheMAproducing activity was found to be inducible with sterols, cholestenone or lithocholic acid, but not with dehydroepiandrosterone, AD, androsta-1,4- ene-3,17-dione or organic acids. Under the optimized conditions, the yield ofMAreached 5 g/l from 10 g/l O-methoxymethyl-ergosterol (approx. 60% molar conversion) for 120 h. The results might be applied at the production of novel vitamin D derivatives.

BIODEGRADATION OF CHOLESTEROL BY A MUTANT OF THE Mycobacterium SPECIES

The biodegradation of cholesterol by the Mycobacterium mutant CCM 3528 gave rise to 22-hydroxy-23,24-bisnorchola-1,4-diene-3-one (I) as the main product.The identified by-products were 24-norchola-1,4-diene-3,22-dione (IX), androsta-1,4-diene-3,17-dione (XV) and their unsaturated analogues, X and XVI respectively.