Bioactive Phenolate Salts: Thymol Salts
Pulikanti Guruprasad Reddy1, Abraham J Domb1
1School of Pharmacy, Faculty of Medicine, The Institute of Drug Research and, The Alex Grass Center for Drug Design and Synthesis, The Hebrew University of Jerusalem, Jerusalem, 91120, Israel.
Chemmedchem
|April 3, 2023
Summary
This study reports the first formation of thymol phenolate salts, enhancing thymol
Area of Science:
- Medicinal Chemistry
- Materials Science
- Organic Chemistry
Background:
- Phenol-containing bioactive agents, like thymol, offer therapeutic benefits but suffer from poor solubility, thermal instability, and high volatility.
- These limitations hinder the practical application of thymol in medicine and agriculture.
- Salt formation presents a strategy to modify and improve the physicochemical properties of such bioactive molecules.
Purpose of the Study:
- To synthesize and characterize novel phenolate salts of thymol.
- To investigate the impact of salt formation on thymol's physicochemical properties, including solubility, thermal stability, and evaporation rate.
- To evaluate the in vitro release characteristics of copper from a synthesized copper-thymol salt.
Main Methods:
- Synthesis of various metal (Na, K, Li, Cu, Zn) and ammonium (tetrabutylammonium, choline) salts of thymol.
- Characterization using IR, NMR, CHN elemental analysis, and Differential Scanning Calorimetry (DSC).
- Determination of molecular formulae and quantification of thymol via UV-Vis spectrophotometry.
- In vitro release studies of copper from the copper-thymol salt at different pH levels.
Main Results:
- Successful synthesis and characterization of multiple thymol phenolate salts, mostly in a 1:1 molar ratio, with a notable 2:1 ratio for the copper salt.
- Most synthesized salts exhibited enhanced thermal stability compared to native thymol.
- Physicochemical properties like solubility and evaporation rate were significantly altered in the salts.
- The copper salt demonstrated pH-dependent in vitro copper release, with rapid release at low pH and minimal release at neutral to alkaline pH.
Conclusions:
- Thymol phenolate salt formation is an effective strategy to improve the physicochemical properties of thymol, addressing its limitations.
- The synthesized salts offer potential for improved formulations and applications in medicine and agriculture.
- The pH-dependent release profile of the copper salt suggests tunable delivery mechanisms.
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