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

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

• 3614-61-7 23,24-Bisnorchola-1,4-dien-3-one-22-carboxylic acid 
• 64284-64-6 4,4-DIMETHYL-5ALPHA-CHOLESTA-8,14,24-TRIENE-3BETA-OL 
• 242142-71-8 (3S,9S,10R,13R,14R,17R)-17-((R)-1,5-Dimethyl-hex-5-enyl)-4,4,10,13-tetramethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol 
• 592536-32-8 (20S)-4,4,20-trimethyl-pregna-5,7-dien-3β,21-diol benzoate 
• 841288-42-4 (20S)-4,4-dimethyl-20-[((triisopropylsilyl)oxy)methyl]-pregna-5,7-dien-3β-ol benzoate 
• 552302-71-3 (20S)-4,4-dimethyl-20-[((toluene-4-sulfonyl)oxy)methyl]-pregna-5,7-dien-3β-ol benzoate 
• 552302-70-2 (20S)-4,4-dimethyl-20-[((triisopropylsilyl)oxy)methyl]-pregna-5-en-3β-ol benzoate 
• 301695-61-4 (5α,7α,24R)-7,24-dihydroxy-3-ketocholestane 
• 140914-97-2 (20S)-21-hydroxy-20-methylpregn-4-en-3-one benzoate 
• 128-13-2 ursodeoxycholic acid 
• 434-13-9 Lithocholic acid 
• 57-83-0 Progesterone 
• 2309-32-2 3-acetoxy-cholesta-3,5-diene 
• 80-97-7 Cholestanol 

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.

New product identification in the sterol metabolism by an industrial strain Mycobacterium neoaurum NRRL B-3805

Mycobacterium neoaurum NRRL B-3805 metabolizes sterols to produce androst-4-en-3,17-dione (AD) as the main product, and androsta-1,4-dien-3,17-dione, 9α-hydroxy androst-4-en-3,17-dione and 22-hydroxy-23,24-bisnorchol-4-en-3-one have been identified as by-products. In this study, a new by-product was isolated from the metabolites of sterols and identified as methyl 3-oxo-23,24-bisnorchol-4-en-22-oate (BNC methyl ester), which was proposed to be produced via the esterification of BNC catalyzed by an O-methyltransferase using S-adenosyl-L-methionine as the methyl group donor. These results might open a new dimension for improvement of the efficiency of microbial AD production by eliminating this by-product via genetic manipulation of the strain.

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.

Novel steroid 5α-reductase inhibitors

Compounds of the following general formula are testosterone 5α-reductase inhibitors rendering the compounds useful in the treatment of acne and oily skin and benign prostatic hypertrophy: STR1 wherein R is: =O, --OH, --OCO--alkyl C1-5, --COOH, --CH2 OH, --COO--alkyl C1-6, --COCH3, STR2