2243-08-5

Basic information

• Product Name: 4-PREGNEN-3,6,20-TRIONE
• Synonyms: 4-PREGNEN-3,6,20-TRIONE;6-KETOPROGESTERONE;Pregn-4-ene-3,6,20-triene;Nsc76757;6-Oxoprogesterone;6-keto group of progesterone;(8S,9S,10R,13S,14S,17S)-17-Acetyl-10,13-dimethyl-7,8,9,11,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,6(2H,10H)-dione
• CAS NO: 2243-08-5
• Molecular Formula: C₂₁H₂₈O₃
• Molecular Weight: 328.45
• EINECS: 1592732-453-0
• Mol File: 2243-08-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 206-208℃ (ethanol )
• Boiling Point: 473.2 °C at 760 mmHg
• Flash Point: 202.6 °C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 4.03E-09mmHg at 25°C
• Refractive Index: 1.55
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Heated)
• CAS DataBase Reference: 4-PREGNEN-3,6,20-TRIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PREGNEN-3,6,20-TRIONE(2243-08-5)
• EPA Substance Registry System: 4-PREGNEN-3,6,20-TRIONE(2243-08-5)

Safety Data

• Hazardous Substances Data: 2243-08-5(Hazardous Substances Data)

Usage

Description

4-PREGNEN-3,6,20-TRIONE, also known as 6-Ketoprogesterone, is a steroidal compound derived from the natural hormone progesterone. It possesses a unique chemical structure characterized by the presence of three functional groups, including a ketone group at the 6th position. This structural feature endows 4-PREGNEN-3,6,20-TRIONE with potential biological activities and applications in various fields.

Uses

Used in Pharmaceutical Industry:
4-PREGNEN-3,6,20-TRIONE is used as a key intermediate in the synthesis of steroidal derivatives, which are essential for the development of novel therapeutic agents. One of its primary applications is in the synthesis and biological evaluation of selective inhibitors of AKR1B10, a promising anti-cancer therapeutic target. By targeting AKR1B10, these steroidal derivatives can potentially inhibit tumor growth and progression, offering a new avenue for cancer treatment.
In addition to its role in cancer therapeutics, 4-PREGNEN-3,6,20-TRIONE may also find applications in other areas of pharmaceutical research, such as hormone regulation, inflammation, and immune response modulation. Its unique chemical properties and structural features make it a valuable compound for further exploration and development in the pharmaceutical industry.

InChI:InChI=1/C21H28O3/c1-12(22)15-4-5-16-14-11-19(24)18-10-13(23)6-8-21(18,3)17(14)7-9-20(15,16)2/h10,14-17H,4-9,11H2,1-3H3/t14-,15+,16-,17-,20+,21+/m0/s1

Upstream product

• 57-83-0 Progesterone 
• 145-13-1 Pregnenolone 

Relevant articles and documents

Stereospecific oxidation of 3β-hydroxysteroids by persolvent fermentation with Pseudomonas sp. ST-200

Pseudomonas sp. strain ST-200 isolated from a humus soil effectively oxidizes cholesterol dissolved in organic solvents but not that suspended in the growth medium. The organism does not assimilate cholesterol. This organism oxidized a variety of 5α- or 5-ene-steroids dissolved in organic solvent. First, the 3β-OH group was oxidized to a ketone group. The 3α-OH group was scarcely oxidized. Successively, C-6 position of 5-ene-steroids was hydroxylated, and a double bond of 5-ene-steroids was transferred from Δ5 to Δ4. Then, the 6-OH group was oxidized to a ketone group. Persolvent fermentation with ST-200 would provide an effective, convenient, and stereospecific method to oxidize the C-3 and C-6 positions of steroids.