13489-75-3

Basic information

• Product Name: tetrahydroaldosterone
• Synonyms: tetrahydroaldosterone;3ALPHA,5B-Tetrahydroaldosterone;11β,18-Epoxy-3α,18,21-trihydroxy-5β-pregnan-20-one;3α,5β-Tetrahydroaldosterone;5β-Pregnan-11β,18-epoxy-3α,18,21-triol-20-one
• CAS NO: 13489-75-3
• Molecular Formula: C₂₁H₃₂O₅
• Molecular Weight: 364.47578
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Steroids
• Mol File: 13489-75-3.mol

Chemical Properties

• Boiling Point: 557.5°Cat760mmHg
• Flash Point: 195.4°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 9.43E-15mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: ?20°C
• CAS DataBase Reference: tetrahydroaldosterone(CAS DataBase Reference)
• NIST Chemistry Reference: tetrahydroaldosterone(13489-75-3)
• EPA Substance Registry System: tetrahydroaldosterone(13489-75-3)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• WGK Germany: 3
• Hazardous Substances Data: 13489-75-3(Hazardous Substances Data)

Usage

Uses

A metabolite of Aldosterone (A514700).

InChI:InChI=1/C21H32O5/c1-20-7-6-12(23)8-11(20)2-3-13-14-4-5-15(16(24)10-22)21(14)9-17(18(13)20)26-19(21)25/h11-15,17-19,22-23,25H,2-10H2,1H3/t11-,12-,13+,14+,15-,17+,18-,19?,20+,21-/m1/s1

Upstream product

• 6251-71-4 11β,21-dihydroxy-3,20-dioxo-5α-pregnan-18-al 
• 64-19-7 acetic acid 
• 76987-53-6 21-acetoxy-11β,18-epoxy-18-methoxy-3α-(tetrahydropyran-2-yloxy)-5β-pregnan-20-one 
• 7305-52-4 11β,21-dihydroxy-3,20-dioxo-5β-pregnan-18-al 
• 113233-88-8 5β-dihydroaldosterone 21-TBDMS ether 
• 113233-91-3 3β,5β-tetrahydroaldosterone 21-TBDMS ether 
• 113233-92-4 3α,5β-tetrahydroaldosterone 21-TBDMS ether 
• 76976-60-8 3α-acetoxy-18,21-dihydroxy-11β,18-epoxy-5β-pregnan-20-one 
• 113233-87-7 5α-dihydroaldosterone 21-TBDMS ether 
• 113233-89-9 3β,5α-tetrahydroaldosterone 21-TBDMS ether 
• 113233-90-2 3α,5α-tetrahydroaldosterone 21-TBDMS ether 

Relevant articles and documents

18-Substituted Steroids. Part 13. Improved Preparation of the Metabolites of Aldosterone Reduced in Ring A

Protection of the side-chain of aldosterone as the 21-t-butyldimethylsilyl (TBDMS) ether was also found to mask the 20-oxo function, by effectively locking the tautomeric structure of aldosterone into its 11,18:18,20-diepoxy form.Catalytic hydrogenation of aldosterone 21-TBDMS ether gave the 5α- or the 5β-dihydro derivative depending on the choice of solvent.Subsequent reduction of the carbonyl group at C-3, with either 'K-selectride' to form the 3-axial alcohol or lithium tri-t-butoxyaluminium hydride to form the 3-equatorial alcohol, was found to proceed without attack on the side-chain, to give convenient routes to the four isomeric tetrahydroaldosterones.

18-Substituted Steroids. Part 7. Synthesis and Structure of 11β,18-Epoxy-3α,18,21-trihydroxy-5β-pregnan-20-one (3α,5β-Tetrahydroaldosterone)

3α,5β-Tetrahydroaldosterone (1) has been prepared from 21-deoxy-3α,5β-tetrahydroaldosterone 18-methyl ether 3-(tetrahydropyran-2-yl) ether (6).Kinetically controlled enolisation with lithium di-isopropylamide followed by treatment with chlorotrimethylsilane generated specifically the Δ20(21)-trimethylsilyl enol ether (17), which reacted with 3-chloroperbenzoic acid to give the 18-methyl ether-21-alcohol (18), which was converted into its 21-acetate (27).Acid solvolysis of the protecting groups at C-3 and -18 with anhydrous acetic acid, followed by mild alkaline hydrolysis with sodium hydrogencarbonate afforded 3α,5β-tetrahydroaldosterone (1) in 26percent overall yield.