5424-40-8

Basic information

• Product Name: (3beta,5alpha,17beta)-androstane-3,17-diyl diacetate
• Synonyms: 3beta,17beta-Diacetoxy-5alpha-androstane; 5.alpha.-androstan-3.beta.,17.beta.-diol, diacetate; 5.alpha.-Androstane-3.beta.,17.beta.-diol, diacetate; 5alpha-Androstane-3beta,17beta-diol diacetate
• CAS NO: 5424-40-8
• Molecular Formula: C₂₃H₃₆O₄
• Molecular Weight: 376.5295
• Mol File: 5424-40-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 440.2°C at 760 mmHg
• Flash Point: 208.9°C
• Density: 1.1g/cm³
• Vapor Pressure: 6.03E-08mmHg at 25°C
• Refractive Index: 1.52
• CAS DataBase Reference: (3beta,5alpha,17beta)-androstane-3,17-diyl diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (3beta,5alpha,17beta)-androstane-3,17-diyl diacetate(5424-40-8)
• EPA Substance Registry System: (3beta,5alpha,17beta)-androstane-3,17-diyl diacetate(5424-40-8)

Safety Data

• Hazardous Substances Data: 5424-40-8(Hazardous Substances Data)

Usage

General Description

"(3β,5α,17β)-androstane-3,17-diyl diacetate" is a steroid compound that belongs to the class of androgens, which are male sex hormones. It is derived from the hormone testosterone and is commonly used in medical and research settings. The compound is a diester of androstanediol, meaning it has two acetate groups attached to its molecular structure. Its chemical properties make it useful for studying and understanding the effects of androgens on the body and for developing pharmaceuticals for conditions related to hormone imbalances. Additionally, it may be used in the production of synthetic hormones for medical purposes.

Upstream product

• 17006-91-6 3-acetyl-17-acetoxyandrost-2-ene 
• 571-40-4 5α-androst-1-ene-3,17-dione 
• 846-46-8 androstanedione 
• 58-22-0 testosterone 
• 481-29-8 Epiandrosterone 
• 5953-57-1 11β-hydroxy-3β-acetoxy-5α-androstanone-(17) 
• 514-17-0 3β,11β-dihydroxy-5α-androstan-17-one 
• 23498-55-7 (3β,5α)-3-(acetyloxy)androstan-17-one 17-oxime 
• 86270-19-1 17-nitroimino-5α-androstan-3β-yl acetate 
• 1239-31-2 3β-acetoxy-5α-androstan-17-one 
• 906-83-2 pregnenolone acetate 
• 7664-93-9 sulfuric acid 
• 64-19-7 acetic acid 
• 3461-74-3 3β-hydroxy-5α-androst-9(11)-en-17-one 3-acetate 

Downstream Products

• 1164-91-6 stanolone acetate 
• 17328-37-9 3β,17β-Dihydroxy-5α-androstan-6-on 
• 571-20-0 5-androgen-3,17-diol 

Relevant articles and documents

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Ceric ammonium nitrate (CAN) catalyzed Baeyer-Villiger oxidation of carbonyl compounds, specially 20-oxosteroids

The role of ceric ammonium nitrate (CAN) as an effective catalyst in the peracid induced Baeyer-Villiger oxidation of carbonyl compounds with special reference to steroids has been demonstrated.

Steroidal N-Nitro-amines. Part 2. Denitroamination of Steroidal 12β-, 17β-, 20β-, and 23R-Nitro-amines

20β-Nitroaminopregn-5-en-3β-yl acetate (13a), 17β-nitroamino-5α-androstan-3β-yl acetate (14), and 12β-nitroamino-(25R)-5α-spirostan-3β-yl acetate (15a) have been prepared by nitrosation of the corresponding oximes, followed by reduction with sodium borohydride.The 23-nitro-imine (12), obtained by reaction of sarsasapogenin acetate (10) with nitrous acid and boron trifluoride-diethyl ether complex, was similarly reduced to give 23R-nitroamino-(20S,22S,25S)-5β-spirostan-3β-yl acetate (16).Denitroamination of (13a) was achieved by treatment with acetic anhydride and pyridine to give the acetates of pregna-5,20-dien-3β-ol (17), pregn-5-ene-3β,20β-diol (18), 17α-methyl-D-homo-androst-5-ene-3,17aβ-diol (19), and 17α-methyl-12a-methylene-C(12a)-homo-18-norandrost-5-en-3β-ol (20).Under the same conditions the nitro-amine (14) afforded the acetates of 5α-androst-16-en-3β-ol (27a), 17β-methyl-18-nor-5α-androst-12-en-3β-ol (28a), 17-methyl-18-nor-5α-androst-13(17)-en-3β-ol (29a), and 17β-methyl-18-nor-5α-androst-13-en-3β-ol (30a).Denitroamination of (15a) took place through the expected C-nor-D-homo rearrangement producing 14(13->12αH)abeo-(25R)-5α-spirost-13(18)-en-3β-yl acetate (31) in high yield and a minor amount of 14(13->12)abeo-(25R)-5α-spist-12-en-3β-yl acetate (32).The trans-stereochemistry of the β-hydrogen-elimination produced in the denitroamination of (16) was established by using labelled sarsasapogenin (10) biosynthesized by Agave attenuata from mevalonic acid.