Tetrahydroaldosterone

Base Information

• Chemical Name: Tetrahydroaldosterone
• CAS No.: 13489-75-3
• Molecular Formula: C₂₁H₃₂O₅
• Molecular Weight: 364.482
• European Community (EC) Number: 692-992-2
• DSSTox Substance ID: DTXSID10928807
• Nikkaji Number: J82.260D
• Mol file: 13489-75-3.mol

Synonyms:3 alpha,5 alpha-tetrahydroaldosterone;3 alpha,5 beta-tetrahydroaldosterone;tetrahydroaldosterone;tetrahydroaldosterone, (3beta,5alpha,11beta)-isomer;tetrahydroaldosterone, (3beta,5beta,11beta)-isomer

Chemical Property of Tetrahydroaldosterone

Chemical Property:

• Vapor Pressure: 9.43E-15mmHg at 25°C
• Boiling Point: 557.5°Cat760mmHg
• Flash Point: 195.4°C
• PSA: 86.99000
• Density: 1.29g/cm³
• LogP: 1.87480
• Storage Temp.: ?20°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 364.22497412
• Heavy Atom Count: 26
• Complexity: 607

Purity/Quality:

99% ^*data from raw suppliers

TetrahydroAldosterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2C4CC5(C3CCC5C(=O)CO)C(O4)O)O
• Isomeric SMILES: C[C@]12CC[C@H](C[C@H]1CC[C@@H]3[C@@H]2[C@@H]4C[C@]5([C@H]3CC[C@@H]5C(=O)CO)C(O4)O)O
• Uses: A metabolite of Aldosterone (A514700).

Technology Process of Tetrahydroaldosterone

There total 17 articles about Tetrahydroaldosterone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

3α,5β-tetrahydroaldosterone 21-TBDMS ether (113233-92-4) → 3α,5β-tetrahydroaldosterone (113301-10-3) + 3α,5β-tetrahydroaldosterone (6251-41-8,13489-75-3,19360-15-7,85966-88-7,89772-54-3,113301-12-5,113301-13-6,113301-14-7,113301-15-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 5h; Yield given. Title compound not separated from byproducts;

Reference yield:

11β,21-dihydroxy-3,20-dioxo-5β-pregnan-18-al (7305-52-4) → 3α,5β-tetrahydroaldosterone (6251-41-8,13489-75-3,19360-15-7,85966-88-7,89772-54-3,113301-12-5,113301-13-6,113301-14-7,113301-15-8)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazole / CH₂Cl₂

2: 3 mg / K-selectride / tetrahydrofuran / 0.75 h / -55 - -50 °C

3: tetrabutylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; potassium tri-sec-butyl-borohydride; In tetrahydrofuran; dichloromethane;

Reference yield:

5β-dihydroaldosterone 21-TBDMS ether (113233-88-8) → 3α,5β-tetrahydroaldosterone (6251-41-8,13489-75-3,19360-15-7,85966-88-7,89772-54-3,113301-12-5,113301-13-6,113301-14-7,113301-15-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 3 mg / K-selectride / tetrahydrofuran / 0.75 h / -55 - -50 °C

2: tetrabutylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

With tetrabutyl ammonium fluoride; potassium tri-sec-butyl-borohydride; In tetrahydrofuran;

upstream raw materials:

3α,5α-tetrahydroaldosterone 21-TBDMS ether

11β,21-dihydroxy-3,20-dioxo-5α-pregnan-18-al

5α-dihydroaldosterone 21-TBDMS ether

3β,5α-tetrahydroaldosterone 21-TBDMS ether

Refernces

• 1、 Kirk, David N.,Miller, Barry W.. "18-Substituted Steroids. Part 7. Synthesis and Structure of 11β,18-Epoxy-3α,18,21-trihydroxy-5β-pregnan-20-one (3α,5β-Tetrahydroaldosterone)". . p. 2818 - 2829. Retrieved 2007/10/02.