7780-63-4

Basic information

• Product Name: Pregna-4,9(11)-diene-17,21-diol-3,20-dione17,21-diacetate
• Synonyms: 17,21-Diacetyloxypregna-4,9(11)-diene-3,20-dione;17,21-Dihydroxypregna-4,9(11)-diene-3,20-dione17,21-diacetate;Pregna-4,9(11)-diene-17,21-diol-3,20-dione17,21-diacetate;17α,21-Diacetoxy-4,9(11)-pregnadiene-3,20-dione;3,20-Dioxopregna-4,9(11)-diene-17α,21-diol diacetate
• CAS NO: 7780-63-4
• Molecular Formula: C₂₅H₃₂O₆
• Molecular Weight: 0
• Mol File: 7780-63-4.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Pregna-4,9(11)-diene-17,21-diol-3,20-dione17,21-diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Pregna-4,9(11)-diene-17,21-diol-3,20-dione17,21-diacetate(7780-63-4)
• EPA Substance Registry System: Pregna-4,9(11)-diene-17,21-diol-3,20-dione17,21-diacetate(7780-63-4)

Safety Data

• Hazardous Substances Data: 7780-63-4(Hazardous Substances Data)

Upstream product

• 1035-69-4 androst-4,9⁽¹¹⁾-dien-3,17-dione 
• 7753-60-8 anecortave 
• 64-19-7 acetic acid 
• 560-62-3 9-alpha-hydroxyandrost-4-ene-3,17-dione 
• 95816-38-9 17α-Hydroxy-21-iodopregna-4,9(11)-diene-3,20-dione 
• 34184-82-2 pregna-4,9⁽¹¹⁾-diene-3,20-dione-17-hydroxy-21-methyl 

Downstream Products

• 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

An efficient procedure for the synthesis of 21-acetoxypregna-1,4,9(11),16-tetraene-3,20-dione

Background: Halogenated corticosteroids are widely used in medicine, and the global need of these steroidal APIs is estimated to be 40 - 70 tons, annually. Vietnam currently imports the pharmaceutical compounds up to 90%, in particular 100% of steroidal drugs. Currently, industrial production is based on the chemical syntheses of corticosteroids from either 16-dehydropregnenolone acetate (obtained from diosgenin) or androstenedione (obtained from phytosterol). The development of shorter synthetic schemes and more economically feasible technologies is of great significance. Introduction of 1(2)-double bond at the final stages of the corticosteroids synthesis results inpoor yield. 21-Acetoxypregna-1,4,9(11),16-tetraene-3,20-dione (tetraene acetate) is a key intermediate in the synthesis of highly active halogenated corticosteroids such as dexamethasone and other halogenated corticosteroids. 21-acetoxypregna-1,4,9(11),16-tetraene-3,20-dione is a key intermediate in the synthesis of dexamethasone from the readily available and cheap 9α-hydroxyandrost-4-ene-3,17-dione. Objective: The purpose of this study was the development of an efficient and shorter procedure for the synthesis of 21-acetoxypregna-1,4,9(11),16-tetraene-3,20-dione from 9α-hydroxyan-drostenedione, which is a product of a bio-oxidative degradation of the side chain of phytosterols. Methods: Pregnane side chain was constructed using cyanohydrin method. For 1(2)-dehydrogenation, selene dioxide was applied for the introduction of Δ1(2)-double bond. Other stages of the synthesis were epimerization, Stork’s iodination procedure and dehydration. Result: 21-Acetoxypregna-1,4,9(11),16-tetraene-3,20-dione was prepared from 9α-hydroxyandrostenedione in yield more than 46%. Conclusion: An efficient and practically feasible procedure for the synthesis of 21-acetoxypregna-1,4,9(11),16-tetraene-3,20-dione from 9α-hydroxyandrostenedione, a key intermediate for the synthesis of 9-haloidated corticoids, has been developed. The procedure can be applied for the production of value-added 9-haloidated corticoids.