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Solvating Effects02:12

Solvating Effects

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An understanding of the solvating effect helps rationalize the relation between solvation and acidity of the compound. In addition, this also explains the relative stability of conjugate bases for compounds with different pKa values. This lesson details, in-depth, the principle of solvating effects. The strength of an acid and the stability of its corresponding conjugate base are determined using pKa values. This observed relationship is a consequence of solvation, which is the interaction...
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Solubility03:00

Solubility

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Solution, Solubility, and Solubility Equilibrium
A solution is a homogeneous mixture composed of a solvent, the major component, and a solute, the minor component. The physical state of a solution—solid, liquid, or gas—is typically the same as that of the solvent. Solute concentrations are often described with qualitative terms such as dilute (of relatively low concentration) and concentrated (of relatively high concentration).
In a solution, the solute particles (molecules,...
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Solubility Equilibria: Overview01:09

Solubility Equilibria: Overview

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When a substance such as sodium chloride is added to water, it dissolves, forming an aqueous solution. The extent of dissolution is called solubility. The process of dissolution can exist in equilibrium, just like other chemical processes. Solubility equilibria are also called precipitation equilibria because the process of solubility can be reversible. The reverse of the solubility process is called precipitation.
Solubility is important in biological and environmental processes. A notable...
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Solubility of Ionic Compounds02:55

Solubility of Ionic Compounds

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Solubility is the measure of the maximum amount of solute that can be dissolved in a given quantity of solvent at a given temperature and pressure. Solubility is usually measured in molarity (M) or moles per liter (mol/L). A compound is termed soluble if it dissolves in water.
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Solubility Equilibria03:07

Solubility Equilibria

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Solubility equilibria are established when the dissolution and precipitation of a solute species occur at equal rates. These equilibria underlie many natural and technological processes, ranging from tooth decay to water purification. An understanding of the factors affecting compound solubility is, therefore, essential to the effective management of these processes. This section applies previously introduced equilibrium concepts and tools to systems involving dissolution and precipitation.
The...
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Physical Properties Affecting Solubility02:19

Physical Properties Affecting Solubility

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Solutions of Gases in Liquids
As for any solution, the solubility of a gas in a liquid is affected by the attractive intermolecular forces between solute and solvent species. Unlike solid and liquid solutes, however, there is no solute-solute intermolecular attraction to overcome when a gaseous solute dissolves in a liquid solvent since the atoms or molecules comprising a gas are far separated and experience negligible interactions. Consequently, solute-solvent interactions are the sole...
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Diagonal Method to Measure Synergy Among Any Number of Drugs
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Some observations on solasodine reactivity.

Izabella Jastrzebska1, Jacek W Morzycki1

  • 1Institute of Chemistry, University of Białystok, Ciołkowskiego 1K, 15-245 Białystok, Poland.

Steroids
|September 10, 2017
PubMed
Summary

New chemical transformations of solasodine, a steroid alkaloid, were achieved. These methods offer potential for the large-scale synthesis of steroid hormone intermediates from spirosolan alkaloids.

Area of Science:

  • Organic Chemistry
  • Natural Product Chemistry
  • Medicinal Chemistry

Background:

  • Solasodine is a key steroid alkaloid sapogenin found in the Solanum family.
  • Steroid hormones are crucial in various physiological processes and therapeutic applications.
  • Efficient synthesis routes for steroid intermediates are vital for pharmaceutical production.

Purpose of the Study:

  • To explore novel chemical transformations of solasodine.
  • To develop efficient synthetic pathways for valuable steroid intermediates.
  • To investigate the potential for large-scale production of drug intermediates from spirosolan alkaloids.

Main Methods:

  • Oxidation of N,O-diacetylated solasodine using NaNO2/BF3·Et2O or t-BuONO/BF3·Et2O.
  • Treatment of the acetylated solasodine with TMSOTf followed by aqueous work-up.
Keywords:
AlkaloidsAutoxidationSapogeninsSolasodineSteroids

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  • Purification of reaction mixtures on silica gel columns to induce autoxidation.

    • Main Results:

    • Partial degradation of the solasodine side chain to (20S)-3β-acetoxypregn-5-ene-20,16β-carbolactone (vespertilin acetate).
    • Formation of a pseudosapogenin derivative after TMSOTf treatment and aqueous work-up.
    • Efficient autoxidation to pregna-5,16-dien-3β-ol-20-one acetate under silica gel chromatography conditions.

    Conclusions:

    • The developed transformations provide new routes for modifying solasodine.
    • One-step synthesis of pregna-5,16-dien-3β-ol-20-one acetate is achievable from spirosolan alkaloids.
    • These findings hold potential for the industrial-scale production of steroid hormones.