Choline Salicylate Analysis: Chemical Stability and Degradation Product Identification

Molecules. 2019 Dec 22;25(1):51. doi: 10.3390/molecules25010051.

Abstract

Choline salicylate (CS) as a derivative of acetylsalicylic acid is commonly used in different drug forms. In medicine, it is applied topically to inflammation of the oral cavity mucosa and in laryngology. However, this substance in the form of an ionic liquid has not been investigated enough. There are no literature studies on stability tests constituting a stage of pre-formulation research. HPLC (Nucleosil C18, 4.6 × 150 mm, 5 μm; methanol-water-acetic acid 60:40:1, 230 nm or 270 nm) and UV (276 nm) methods for the determination of CS in 2% (g/mL) aqueous solutions were developed. Under stress conditions, CS susceptibility to hydrolytic degradation in aqueous medium, hydrochloric acid, sodium hydroxide, and hydrogen peroxide, and the effect of light on the stability of CS solutions were studied with HPLC analysis. The degradation degree of CS and the purity of the solutions were also tested. Choline salicylate has been qualified as practically stable in neutral and acid media, stable in an alkaline medium, very stable in an oxidizing environment, and photolabile in solution. The HPLC-MS/MS method was used to identify 2,3- and 2,5-dihydroxybenzoic acids as degradation products of CS under the tested conditions.

Keywords: HPLC; HPLC-MS/MS; UV; choline salicylate; ionic liquid; stress test.

MeSH terms

  • Choline / analogs & derivatives*
  • Choline / chemistry
  • Chromatography, High Pressure Liquid
  • Drug Combinations
  • Drug Stability
  • Gentisates / analysis*
  • Hydrolysis
  • Hydroxybenzoates / analysis*
  • Molecular Structure
  • Photolysis
  • Salicylates / chemistry*
  • Tandem Mass Spectrometry

Substances

  • Drug Combinations
  • Gentisates
  • Hydroxybenzoates
  • Salicylates
  • 2,3-dihydroxybenzoic acid
  • choline salicylate
  • Choline
  • 2,5-dihydroxybenzoic acid