23460-76-6

Basic information

• Product Name: 21-hydroxypregna-4,9(11),16-triene-3,20-dione 21-acetate
• Synonyms: 21-hydroxypregna-4,9(11),16-triene-3,20-dione 21-acetate;21-(Acetyloxy)pregna-4,9(11),16-triene-3,20-dione;3,20-Dioxopregna-4,9(11),16-triene-21-ol acetate;Einecs 245-674-9
• CAS NO: 23460-76-6
• Molecular Formula: C₂₃H₂₈O₄
• Molecular Weight: 368.46602
• EINECS: 245-674-9
• Mol File: 23460-76-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 124-125 °C(Solv: acetone (67-64-1); ligroine (8032-32-4))
• Boiling Point: 529.6°Cat760mmHg
• Flash Point: 230.4°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 2.65E-11mmHg at 25°C
• Refractive Index: 1.569
• CAS DataBase Reference: 21-hydroxypregna-4,9(11),16-triene-3,20-dione 21-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 21-hydroxypregna-4,9(11),16-triene-3,20-dione 21-acetate(23460-76-6)
• EPA Substance Registry System: 21-hydroxypregna-4,9(11),16-triene-3,20-dione 21-acetate(23460-76-6)

Safety Data

• Hazardous Substances Data: 23460-76-6(Hazardous Substances Data)

Usage

Description

21-Hydroxypregna-4,9(11),16-triene-3,20-dione 21-acetate, also known as Hydrocortisone 21-Acetate, is a glucocorticoid derived from Hydrocortisone EP Impurity C. It is a steroid hormone with anti-inflammatory and immunosuppressive properties, making it a valuable compound in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
21-Hydroxypregna-4,9(11),16-triene-3,20-dione 21-acetate is used as a glucocorticoid for its anti-inflammatory and immunosuppressive effects. It is particularly useful in the treatment of various inflammatory and autoimmune conditions, such as rheumatoid arthritis, lupus, and asthma. Its ability to modulate the immune system and reduce inflammation makes it a valuable therapeutic agent in this application.
Used in Steroid Synthesis:
In the chemical industry, 21-Hydroxypregna-4,9(11),16-triene-3,20-dione 21-acetate serves as an intermediate in the synthesis of other steroidal compounds. Its structural properties allow for further modification and development of new steroids with specific therapeutic applications, contributing to the diversity of steroidal drugs available for various medical conditions.
Used in Research and Development:
21-Hydroxypregna-4,9(11),16-triene-3,20-dione 21-acetate is also utilized in research and development for studying the effects of glucocorticoids on various biological processes. Its role in modulating inflammation and immune responses makes it an important tool for understanding the underlying mechanisms of these processes and for developing new therapeutic strategies to target them.

InChI:InChI=1/C23H28O4/c1-14(24)27-13-21(26)20-7-6-18-17-5-4-15-12-16(25)8-10-22(15,2)19(17)9-11-23(18,20)3/h7,9,12,17-18H,4-6,8,10-11,13H2,1-3H3

Upstream product

• 108-24-7 acetic anhydride 
• 1035-69-4 Androstadien-(4,9,⁽¹¹⁾)-dion-3,17 
• 98131-35-2 21-acetoxy-11α-(toluene-4-sulfonyloxy)-pregna-4,16-diene-3,20-dione 
• 24510-86-9 21-Hydroxypregna-4,9⁽¹¹⁾,16-triene-3,20-dione 
• 74176-89-9 9α-chloro-21-acetoxy-17α-(3-iodobenzoyloxy)-4-pregnene-3,20-dione 
• 7753-60-8 anecortave 
• 50-03-3 hydrocortisone acetate 
• 1035-69-4 androst-4,9⁽¹¹⁾-dien-3,17-dione 
• 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 
• 7780-63-4 pregna-4,9(11)-diene-17α,21-diol-3,20-dione 17,21-diacetate 

Downstream Products

• 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 
• 74220-43-2 21-Acetoxy-16α,17α-dihydroxy-4,9(11)-pregnadien-3,20-dion 
• 124-94-7 triamcinolone 
• 337-02-0 9α-fluoro-11β,16α,17α,21-tetrahydroxypregn-4-ene-3,20-dione 
• 1868-22-0 16α,21-diacetoxy-9-fluoro-17-hydroxy-pregna-1,4-diene-3,11,20-trione 
• 67-78-7 triamcinolone diacetate 
• 76-25-5 triamcinolone acetonide 
• 1524-86-3 16α-17-[(1-methylethylidene)bis(oxy)]-11β,21-dihydroxy-9-fluoro-4-ene-pregna-3,20-dione 
• 37413-91-5 21-Acetoxy-1,4,9⁽¹¹⁾,16-pregnatetraen-3,20-dion 
• 802-71-1 (8S,9R,10S,11S,13S,14S)-9-Fluoro-11-hydroxy-17-(2-hydroxy-acetyl)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15-dodecahydro-cyclopenta[a]phenanthren-3-one 
• 3093-35-4 halcinonide 

Relevant articles and documents

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Synthesis method of triene acetate compound

The invention belongs to the technical field of steroid hormone preparation, in particular to a synthesis method of a triene acetate compound. The preparation method comprises the following steps: under the participation of 4-dimethylaminopyridine, removing 17-site hydroxyl of the anecortave acetate by using an N-chlorosuccinimide and a sulfur dioxide pyridine solution; and after the reaction is finished, performing crystallization to obtain the triene acetate compound. The 4-dimethylaminopyridine is added into the reaction system, an intermediate is stabilized, generation of rearrangement impurities is well inhibited, and the content of the rearrangement impurities in the system is reduced from 12% to 2%, so that the triene acetate compound is obtained at a high yield, with the purity reaching 99%, and the yield being 80% or above.

Preparation method of delta 16 steroid

The invention relates to a preparation method of a delta 16 steroid. At the atmosphere of protective gas, a compound of a formula II, an oxidizing agent and sulfur dioxide are subjected to a reaction in an organic solvent, the reaction temperature ranges from minus 50 DEG C to 0 DEG C, and the reaction time is 1.5-2.5 h to obtain a delta 16 steroid I, wherein R1 is selected from H, halogen and acyloxy or hydroxide of C1-5; R2 is selected from alkyl of alpha C1-3 and alkyl or H of beta C1-2; R3 is selected from H, alkyl of alpha C1-3, alkyl of beta C1-2, alpha halogen or beta halogen; R4 and R5 are equal to H or double bonds; R7 is selected from H, and R6 is selected from H, alkyl of C1-3 or acyloxy of C1-5; or R6 and R7 are equal to double bonds. According to the preparation method of the delta 16 steroid, the 17-bit hydroxide compound of the formula II is used as raw materials, and the compound of the formula II is industrially produced and is easy to obtain; the preparation method is mild in reaction condition, no high-temperature strong base or strong acid is needed, fewer by-products are produced, the product yield and purity are high, the yield reaches more than 90%, and the purity reaches more than 93%.