600-48-6

Basic information

• Product Name: (6beta,11alpha)-6,11-dihydroxypregn-4-ene-3,20-dione
• Synonyms: 6beta,11alpha-Dihydroxypregn-4-ene-3,20-dione; 6beta,11alpha-Dihydroxyprogesterone
• CAS NO: 600-48-6
• Molecular Formula: C₂₁H₃₀O₄
• Molecular Weight: 346.4605
• Mol File: 600-48-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 532.1°C at 760 mmHg
• Flash Point: 289.7°C
• Density: 1.21g/cm³
• Vapor Pressure: 1.52E-13mmHg at 25°C
• Refractive Index: 1.573
• CAS DataBase Reference: (6beta,11alpha)-6,11-dihydroxypregn-4-ene-3,20-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (6beta,11alpha)-6,11-dihydroxypregn-4-ene-3,20-dione(600-48-6)
• EPA Substance Registry System: (6beta,11alpha)-6,11-dihydroxypregn-4-ene-3,20-dione(600-48-6)

Safety Data

• Hazardous Substances Data: 600-48-6(Hazardous Substances Data)

Usage

General Description

The chemical "(6beta,11alpha)-6,11-dihydroxypregn-4-ene-3,20-dione" is a steroid hormone and a metabolite of cortisol. It is produced in the adrenal glands and plays a crucial role in various physiological processes, including metabolism, immune response, and stress regulation. This chemical also acts as a precursor for the synthesis of other important hormones, such as aldosterone and androgens. Additionally, it has anti-inflammatory and immunosuppressive properties, making it a key target for pharmaceutical research in the development of new drugs for treating conditions such as autoimmune diseases and allergies.

Upstream product

• 57-83-0 Progesterone 

Downstream Products

• 80-75-1 11-alpha-hydroxyprogesterone 

Relevant articles and documents

Biotransformation of progesterone by Aspergillus nidulans VKPM F-1069 (wild type)

Biotechnological transformation of steroids using enzyme systems of microorganisms is often the only possible method to modify the molecule in the industrial production of steroid drugs. Filamentous fungus Aspergillus nidulans has been little studied as a steroid-transforming microorganism. We studied the ability of the A. nidulans VKPM F-1069 strain to transform progesterone (PG) for the first time. This strain converts PG into 3 main products: 11α-hydroxy-PG, 11α-acetoxy-PG and 6β,11α-dihydroxy-PG. It has been established that in the first stage, the hydroxylation of PG occurs into C11α position, then the formed 11α-hydroxy-PG is modified into 11α-acetoxy-PG and 6β,11α-dihydroxy-PG. It was found that changes in the composition of the growth medium, aeration and the duration of the mycelium cultivation do not affect the qualitative composition of PG transformation products, but their ratios have changed. Under conditions of limited aeration, the direction of secondary modification of 11α-hydroxy-PG is shifted towards the formation of 11α-acetoxy-PG.

Biocatalyst mediated production of 6β,11α-dihydroxy derivatives of 4-ene-3-one steroids

Biotransformation of steroids with 4-ene-3-one functionality such as progesterone (I), testosterone (II), 17α-methyltestosterone (III), 4-androstene-3,17-dione (IV) and 19-nortestosterone (V) were studied by using a fungal system belonging to the genera of Mucor (M881). The fungal system efficiently and quantitatively converted these steroids in regio- and stereo-selective manner into corresponding 6β,11α-dihydroxy compounds. Time course experiments suggested that the transformation was initiated by hydroxylation at 6β- or 11α-(10β-hydroxy in case of V) to form monohydroxy derivatives which upon prolonged incubation were converted into corresponding 6β,11α-dihydroxy derivatives. The fermentation studies carried out using 5 L table-top fermentor with substrates (I and II) clearly indicates that 6β,11α-dihydroxy derivatives of steroids with 4-ene-3-one functionality can be produced in large scale by using M881.

HYDROXYLATION OF PROGESTERONE BY CEPHALOSPORIUM APHIDICOLA

The fungus, Cephalosporium aphidicola, has been shown to hydroxylate progesterone predominantly at the 6β- and 11α-positions.Minor metabolites include tetstosterone acetate, the 20(R)-alcohol and 12β,17α-dihydroxyprogesterone.The sequence involves hydroxylation at 11α and then 6β.The hydroxylations of 11α- and 17α-hydroxyprogesterone and 9β,10α-retroprogesterone have also been examined in the light of these results. - Key words: Cephalosporium aphidicola; progesterone; 9β,10α-retroprogesterone; steroid; microbiological hydroxylation.