560-62-3

Basic information

• Product Name: 9-hydroxy-4-androstene-3,17-dione
• Synonyms: 9-hydroxy-4-androstene-3,17-dione;Androst-4-ene-3,17-dione,9-hydroxy-;(9xi)-9-hydroxyandrost-4-ene-3,17-dione;9alpha-hydroxyandrost-4-en-3,17-dione;(8S,9R,10S,13S,14S)-9-Hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione
• CAS NO: 560-62-3
• Molecular Formula: C₁₉H₂₆O₃
• Molecular Weight: 302.41
• EINECS: 1308068-626-2
• Mol File: 560-62-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 222-223.5 °C
• Boiling Point: 470.3°Cat760mmHg
• Flash Point: 252.3°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 8.05E-11mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: 2-8°C
• PKA: 14.17±0.60(Predicted)
• CAS DataBase Reference: 9-hydroxy-4-androstene-3,17-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 9-hydroxy-4-androstene-3,17-dione(560-62-3)
• EPA Substance Registry System: 9-hydroxy-4-androstene-3,17-dione(560-62-3)

Safety Data

• Hazardous Substances Data: 560-62-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
9-hydroxy-4-androstene-3,17-dione is used as an intermediate in the synthesis of highly effective fluorinated anti-inflammatory remedies. Its potent anti-inflammatory properties make it a valuable component in the development of new medications aimed at reducing inflammation and alleviating pain associated with various conditions.
Used in Anti-Inflammatory Applications:
9-hydroxy-4-androstene-3,17-dione is employed as an active ingredient in the development of anti-inflammatory drugs. Its ability to modulate inflammatory responses and reduce pain makes it a promising candidate for the treatment of various inflammatory disorders, such as arthritis, asthma, and other conditions characterized by chronic inflammation.

InChI:InChI=1/C19H26O3/c1-17-9-10-19(22)15(14(17)5-6-16(17)21)4-3-12-11-13(20)7-8-18(12,19)2/h11,14-15,22H,3-10H2,1-2H3/t14-,15-,17-,18-,19?/m0/s1

Upstream product

• 566-61-0 allopregnenolone 
• 58-22-0 testosterone 
• 63-05-8 Androstenedione 
• 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 
• 83-46-5 β-sitosterol 
• 165281-40-3 3β,9α-dihydroxyandrost-5-en-17-one 
• 853-23-6 prasterone acetate 
• 57-88-5 cholesterol 

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 
• 2394-69-6 3-hydroxy-9,10-secoandrosta-1,3,5⁽¹⁰⁾-triene-9,17-dione 
• 116256-39-4 9α,17β-dihydroxy-17α-ethynylandrost-4-en-3-one 
• 121058-06-8 3β,4β,17β-triacetoxy-9,10-seco-androst-5(10)-en-9-one 
• 121058-05-7 3β,10α,17b-triacetoxy-9,10-seco-androst-4-en-9-one 
• 121154-10-7 3β,10β,17b-triacetoxy-9,10-seco-androst-4-en-9-one 
• 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 
• 34184-82-2 pregna-4,9⁽¹¹⁾-diene-3,20-dione-17-hydroxy-21-methyl 
• 7753-60-8 anecortave 
• 7780-63-4 pregna-4,9(11)-diene-17α,21-diol-3,20-dione 17,21-diacetate 
• 23460-76-6 21-acetoxy-pregna-4,9⁽¹¹⁾,16-triene-3,20-dinone 
• 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 

Relevant articles and documents

Identification andin situremoval of an inhibitory intermediate to develop an efficient phytosterol bioconversion process using a cyclodextrin-resting cell system

A classically versatile steroid intermediate, 9α-hydroxyandrost-4-ene-3,17-dione (9α-OH-AD), can be obtained by phytosterol (PS) bioconversion usingMycobacterium. In this study, a cyclodextrin-resting cell reaction system with a high concentration of PS (50 g L?1) was used to produce 9α-OH-AD. However, the inhibitory effect of metabolic intermediates is a key factor limiting production efficiency. After the separation and identification of a series of metabolic intermediates, it was found that 4-ene-3-keto steroids, which are the first metabolites of sterol side-chain degradation, accumulated at the beginning of the bioprocess and had a remarkable inhibitory effect on bioconversion. The bioconversion rate was greatly improved when 5 g L?1of macroporous adsorbent resin D101 was added to the reaction system in the initial phase. A certain amount of resin acted as a reservoir to remove the inhibitory intermediatein situand facilitated the bioconversion process, and the 9α-OH-AD space-time yield increased to 8.51 g L?1d?1, which was 23.15% higher than that without resin addition (6.91 g L?1d?1) after 72 h bioconversion. In summary, we identified an inhibitory intermediate that limits the bioconversion rate and provided a solution based on resin adsorption for improving 9α-OH-AD production efficiency in a commercial-scale process.

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.

PROCESS FOR THE SELECTIVE ISOLATION, PURIFICATION AND SEPARATION OF MONOHYDROXYLATED 3,17-DIKETO-STEROID COMPOUNDS

The subject of the present invention is a new process for the selective isolation, purification and separation of monohydroxylated 3,17-diketo-steroid compounds from a solution obtained preferably by microbiological way containing a mixture of steroid compounds via selective extraction, purification and selective crystallization of the steroid compounds by treatment of several solvents.

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.

Transformed steroids 195. Introduction of the 9α-hydroxygroup into Δ5-3β-hydroxysteroids by Circinella sp. mold

A preparative method of 9α-hydroxylation of Δ5-3β-hydroxysteroids using the fungi of Circinella sp.IOKh-1220 not capable of modifying the ring A has been developed.It is established that the yields of the main and the side products greatly depend on the transformation conditions, mycelium age, and the structure of the steroid substrate.Under the optimal transformation conditions novel 9α-hydroxysubstituted derivatives of androstenolone, pregnenolone, 16-dehydro-16α,17α-epoxy-, and 16α-methoxypregnenolone have been obtained in 36-80percent yields. - Key words: hydroxylation, Δ5-3β-hydroxysteroids, Δ5-3β,9α-dihydroxysteroids, Circinella sp.

SYNTHESIS OF 9α-HYDROXYSTEROIDS BY A RHODOCOCCUS SP.

9α-Hydroxylation of Δ5-3β-hydroxysteroids (of androstane, pregnane, 24-nor- and 21,24-bisnorcholane groups) was carried out by a Rhodococcus sp., isolated from a petroleum-containing soil sample.A large number of the investigated steroids was transformed into 9α-hydroxy-Δ4-3-ketones in satisfactory yields (50 - 90percent) at high initial concentrations of the substrates (0.5 - 5.0 g/L).The influence of some structural features of the steroid molecule on the progress and effectiveness of the microbial transformation was also shown.

MICROBIAL DEGRADATION OF THE PHYTOSTEROL SIDE-CHAIN TO 24-OXO PRODUCTS

A mutant of the potent sterol degrader Mycobacterium fortuitum (ATCC 6842) has been isolated which is defective in its ability to degrade both the steroid nucleus and sterol side-chains that are branched at the 24-position.Bioconversions of phytosterol mixtures by this mutant resulted in the accumulation of the novel 24-oxo intermediates 9-hydroxy-27-nor-4-cholestene-3,24-dione (II) and 9-hydroxy-26,27-dinor-4-cholestene-3,24-dione (III).Under the same conditions, cholesterol is degraded mainly to 9-hydroxy-4-androstene-3,17-dione (I) by this organism.