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

Description

9-hydroxy-4-androstene-3,17-dione, also known as 9α-Hydroxyandrost-4-ene-3,17-dione, is a 3-oxo-Δ4-steroid derived from androst-4-ene. It is characterized by the presence of oxo groups at positions 3 and 17, along with a hydroxy group at position 9. 9-hydroxy-4-androstene-3,17-dione has been found to possess significant anti-inflammatory properties, making it a valuable compound in the pharmaceutical industry.

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

• 57-88-5 cholesterol 
• 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 
• 853-23-6 prasterone acetate 
• 566-61-0 allopregnenolone 
• 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 
• 2394-69-6 3-hydroxy-9,10-secoandrosta-1,3,5⁽¹⁰⁾-triene-9,17-dione 
• 83-44-3 Deoxycholic acid 
• 571-49-3 3α-hydroxy-5β-androst-9(11)-en-17-one 
• 1093397-74-0 methyl 3α-acetoxy-5β-chol-9(11),16-dien-24-oate 
• 4472-02-0 methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate 
• 5143-55-5 methyl 3α-acetoxy-12-oxo-5β-cholan-24-oate 
• 27240-83-1 methyl 3α-acetoxy-12α-hydroxy-5β-cholan-24-oate 
• 24637-47-6 12β-hydroxy-3α-acetoxy-5β-cholen-(9(11))-oic acid-(24)-methyl ester 
• 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 

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.

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.