23015-99-8

Basic information

• Product Name: Androst-4-ene-3,17-dione, 9-hydroxy-, (9.beta.,10.alpha.)-
• Synonyms: Androst-4-ene-3,17-dione, 9-hydroxy-, (9.beta.,10.alpha.)-
• CAS NO: 23015-99-8
• Molecular Formula: C₁₉H₂₆O₃
• Molecular Weight: 302.41
• Mol File: 23015-99-8.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Androst-4-ene-3,17-dione, 9-hydroxy-, (9.beta.,10.alpha.)-(CAS DataBase Reference)
• NIST Chemistry Reference: Androst-4-ene-3,17-dione, 9-hydroxy-, (9.beta.,10.alpha.)-(23015-99-8)
• EPA Substance Registry System: Androst-4-ene-3,17-dione, 9-hydroxy-, (9.beta.,10.alpha.)-(23015-99-8)

Safety Data

• Hazardous Substances Data: 23015-99-8(Hazardous Substances Data)

Upstream product

• 853-23-6 prasterone acetate 
• 419543-03-6 C₂₃H₃₂Br₂O₄ 
• 103189-15-7 C₁₉H₂₄Br₂O₂ 
• 102047-66-5 3,3-dimethoxyestr-5⁽¹⁰⁾-ene 17-ketal 
• 1238-30-8 17,17-ethanediyldioxy-3-methoxy-estra-2,5⁽¹⁰⁾-diene 
• 57-83-0 Progesterone 
• 152-58-9 Cortexolone 
• 53-43-0 dehydroepiandrosterone 
• 58-22-0 testosterone 
• 83-46-5 β-sitosterol 
• 165281-40-3 3β,9α-dihydroxyandrost-5-en-17-one 
• 566-61-0 allopregnenolone 
• 57-88-5 cholesterol 
• 566-12-1 9α-hydroxycortexolone 

Downstream Products

• 116256-35-0 17β-Cyano-9α,17α-dihydroxyandrost-4-en-3-one 
• 1035-69-4 androst-4,9⁽¹¹⁾-dien-3,17-dione 
• 37413-91-5 2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate 
• 23460-76-6 21-acetoxy-pregna-4,9⁽¹¹⁾,16-triene-3,20-dinone 
• 7780-63-4 pregna-4,9(11)-diene-17α,21-diol-3,20-dione 17,21-diacetate 
• 7753-60-8 anecortave 
• 34184-82-2 pregna-4,9⁽¹¹⁾-diene-3,20-dione-17-hydroxy-21-methyl 
• 5143-55-5 methyl 3α-acetoxy-12-oxo-5β-cholan-24-oate 
• 24637-47-6 12β-hydroxy-3α-acetoxy-5β-cholen-(9(11))-oic acid-(24)-methyl ester 
• 27240-83-1 methyl 3α-acetoxy-12α-hydroxy-5β-cholan-24-oate 
• 4472-02-0 methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate 
• 1093397-74-0 methyl 3α-acetoxy-5β-chol-9(11),16-dien-24-oate 
• 571-49-3 3α-hydroxy-5β-androst-9(11)-en-17-one 
• 83-44-3 Deoxycholic acid 

Relevant articles and documents

A novel 3-phytosterone-9α-hydroxylase oxygenation component and its application in bioconversion of 4-androstene-3,17-dione to 9α-hydroxy-4-androstene-3,17-dione coupling with a NADH regeneration formate dehydrogenase

9α-Hydroxy-4-androstene-3,17-dione (9-OH-AD) is one of the significant intermediates for the preparation of β-methasone, dexamethasone, and other steroids. In general, the key enzyme that enables the biotransformation of 4-androstene-3,17-dione (AD) to 9-OH-AD is 3-phytosterone-9α-hydroxylase (KSH), which consists of two components: a terminal oxygenase (KshA) and ferredoxin reductase (KshB). The reaction is carried out with the concomitant oxidation of NADH to NAD+. In this study, the more efficient 3-phytosterone-9α-hydroxylase oxygenase (KshC) from the Mycobacterium sp. strain VKM Ac-1817D was confirmed and compared with reported KshA. To evaluate the function of KshC on the bioconversion of AD to 9-OH-AD, the characterization of KshC and the compounded system of KshB, KshC, and NADH was constructed. The optimum ratio of KSH oxygenase to reductase content was 1.5:1. An NADH regeneration system was designed by introducing a formate dehydrogenase, further confirming that a more economical process for biological transformation from AD to 9-OH-AD was established. A total of 7.78 g of 9-OH-AD per liter was achieved through a fed-batch process with a 92.11% conversion rate (mol/mol). This enzyme-mediated hydroxylation method provides an environmentally friendly and economical strategy for the production of 9-OH-AD.

METHODS FOR PREPARING SYNTHETIC BILE ACIDS AND COMPOSITIONS COMPRISING THE SAME

This invention relates generally to methods for preparing certain bile acids from non-mammalian sourced starting materials as well as to synthetic bile acids and compositions comprising such acids wherein the acids are characterized by a different C14 population than naturally occurring bile acids as well as being free from any mammalian pathogens. This invention is also directed to the synthesis of intermediates useful in the synthesis of such bile acids. Accordingly, the C ring of the steroidal scaffold is oxidized to provide a synthetic route and intermediates to DCA. This invention also provides synthetic methods for preparing deoxycholic acid or a salt thereof starting from aromatic steroids such as estrogen, equilenin, and derivatives thereof. This invention is also directed to intermediates such as 12-oxo or delta-9,11-ene steroids as well as novel processes for their preparation. In preferred embodiments, bile acids are provided herein which have substituents on the B-ring and/or D-ring side chain and optionally on the hydroxy group of the A-ring.

Steroid 9α-hydroxylation during testosterone degradation by resting Rhodococcus equi cells

The conversion pathway of testosterone to androst-4-ene-3,17-dione and 9α-hydroxy androstane metabolites, 9α-hydroxyandrost-4-ene-3,17- dione and 9α,17β-dihydroxyandrost-4-en-3-one was proposed for the ring degradation in steroids by a minimal liquid medium (NMMP)-dispersed Rhodococcus equi ATCC 14887. The microorganism produced 9α-hydroxy androstane metabolites from testosterone at high conversion ratio without the addition of ring degradation inhibitory agents. Several NMMP-based media showed the similar effect on the microbial transformation, in which the respective molar yields of 9α-hydroxyandrost-4-ene-3,17-dione and 9α,17β-dihydroxyandrost-4-en-3-one were approx. 3 to 47% and approx. 3 to 11%, respectively, whereas nutrient broth, a rich medium, basically showed no accumulation. On the basis of this evidence, magnesium sulfate and casamino acids among the components of NMMP were found to compromise the determinant for the production of the 9α-hydroxy androstane metabolites without appreciable decomposition of the steroid ring system.