14148-09-5

Basic information

• Product Name: 17β-Acetyl-5,6α-epoxy-5α-androstane-3β-ol acetate
• Synonyms: 5a-Pregnan-20-one, 5,6a-epoxy-3b-hydroxy-, acetate (6CI,7CI,8CI);5,6-Epoxy-5H-cyclopenta[a]phenanthrene, pregnan-20-one deriv.; 3b-Acetoxy-5,6a-epoxy-5a-pregnan-20-one; 3b-Acetoxy-5a,6a-epoxypregnan-20-one; NSC 20794; NSC 63554
• CAS NO: 14148-09-5
• Molecular Formula: C₂₃H₃₄O₄
• Molecular Weight: 374.51366
• Mol File: 14148-09-5.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 469.3°Cat760mmHg
• Flash Point: 202°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 5.57E-09mmHg at 25°C
• Refractive Index: 1.543
• CAS DataBase Reference: 17β-Acetyl-5,6α-epoxy-5α-androstane-3β-ol acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 17β-Acetyl-5,6α-epoxy-5α-androstane-3β-ol acetate(14148-09-5)
• EPA Substance Registry System: 17β-Acetyl-5,6α-epoxy-5α-androstane-3β-ol acetate(14148-09-5)

Safety Data

• Hazardous Substances Data: 14148-09-5(Hazardous Substances Data)

Usage

Description

17β-Acetyl-5,6α-epoxy-5α-androstane-3β-ol acetate is a synthetic steroid androgenic-anabolic steroid (AAS) that is a modified version of the natural hormone testosterone. It belongs to the group of 17α-alkylated AAS and features an added acetyl group and an epoxy group. 17β-Acetyl-5,6α-epoxy-5α-androstane-3β-ol acetate is designed to enhance performance, particularly in bodybuilding, by increasing muscle mass and strength.

Uses

Used in Performance Enhancement:
17β-Acetyl-5,6α-epoxy-5α-androstane-3β-ol acetate is used as a performance-enhancing substance in bodybuilding for its ability to increase muscle mass and strength. It is favored for its anabolic effects, which can lead to improved physical performance.
Used in Sports and Athletics:
In the realm of sports and athletics, 17β-Acetyl-5,6α-epoxy-5α-androstane-3β-ol acetate is used as a banned substance due to its potential for abuse and the health risks associated with its use. Athletes may seek to use it illicitly to gain a competitive edge, despite strict regulations and bans in many countries.

InChI:InChI=1/C23H34O4/c1-13(24)17-5-6-18-16-11-20-23(27-20)12-15(26-14(2)25)7-10-22(23,4)19(16)8-9-21(17,18)3/h15-20H,5-12H2,1-4H3/t15-,16-,17+,18-,19-,20-,21+,22+,23-/m0/s1

Upstream product

• 1778-02-5 Pregnenolone acetate 
• 145-13-1 Pregnenolone 
• 108-24-7 acetic anhydride 
• 2193-00-2 3β-hydroxy-5α,6α-epoxypregnane-20-oxide 

Downstream Products

• 103100-68-1 6β-Phenoxy-5α-hydroxy-pregnan-3,20-dion 
• 103050-38-0 6β-Phenoxy-34b,5α-dihydroxy-pregnan-20-on 
• 2300-03-0 6α-Fluoro-4-pregnene-3,20-dione 
• 103209-04-7 6β-Phenoxy-5α-hydroxy-3β-acetoxy-pregnan-20-on 
• 1778-02-5 Pregnenolone acetate 
• 4660-45-1 6β-fluoro-5-hydroxy-5α-pregnane-3,20-dione 
• 1868-98-0 6β-fluoro-3β,5-dihydroxy-5α-pregnan-20-one 

Relevant articles and documents

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A Convenient Synthesis of 5,6β-Epoxides of Some Cholesteryl Esters and Δ5-Ketosteroid Derivatives by Catalytic β-Stereoselective Epoxidation

The epoxidation of a series of cholesteryl esters by air in the presence of a catalytic amount of a ruthenium tetramesitylporphyrin complex is described.The preparative procedure, which requires only 4 to 5 mol percent of the catalyst, leads to high conve

Highly efficient epoxidation of unsaturated steroids using magnesium bis(monoperoxyphthalate) hexahydrate

Fast generation of epoxides from the corresponding homoallylic and allylic steroidal olefins was developed by using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP) as oxidant suspended in acetonitrile (CH3CN) at reflux temperature. The protocol involves the use of a safe readily available oxidant along with an easy work-up, which renders the process very efficient. Selective 4,5- and 5,6-epoxidations of steroids are reported. Among them, highly stereoselective epoxidation of Δ5-B-nor-cholestanes was achieved. Moreover, the method is chemoselective for the 5,6-position and can be applied to the epoxidation of ring-A enones.

Ring A aromatic steroids in the pregnane series

4-Methylpregna-1,3,5(10)-trien-20-one and 4-methylpregna-1,3,5(10),16- tetraen-20-one have been obtained by a dienol: benzene type of rearrangement of 5α,6α-epoxypregnanes possessing a further double bond equivalent on ring A. The crystal structure of 4-methyl-19-norpregna-1,3,5(10)-trien-20-one is reported.