Chiral Separations of Pyrethroic Acids Using Cyclodextrin Selectors

Abstract

Pyrethroid insecticides are broadly used. They have low toxicity for warm-blooded living creatures, but high toxicity for both insects and fish. Therefore, it is important to reduce the environmental impact of pyrethroids. Pyrethroic acids are chiral compounds. An effective way to decrease pollution is to use enantio-pure insecticide products instead of their racemic mixtures. Enantiomer-pure products require enantiomer selective synthesis and analysis. The chiral selective analysis of pyrethroic acids (an intermediate of pyrethroids) is also important in terms of process control and from the point of view of their degradation metabolism in the environment. This study used various enantiomeric selective chromatographic methods for the separation of different pyrethroic acids, including gas chromatography, supercritical fluid chromatography and capillary electrophoresis. Systematic experiments were conducted to find the optimum conditions for their chiral separation. The employed enantio-selective agents were cyclodextrin derivatives with different ring sizes and substitution patterns. The β-cyclodextrin proved to be excellent for the chiral separation of these acids. The different chiral recognition mechanisms were established using different ring-sized cyclodextrins. The results of these systematic studies demonstrated the correlations of the chiral selectivity features of selectors and the structures of analytes.

Chiral resolution of ketoprofen by modified polymethyl methacrylate microspheres

“…Cyclodextrin has been studied by many researchers because of its unique ability to recognize chiral drugs. [10][11][12] Juvancz et al 13 used different cyclodextrins and different chiral recognition mechanisms to complete the chiral separation of pyrethroid acid. La et al 14 used anionic cyclodextrin to separate eight chiral drugs and successfully optimized the separation conditions.…”

New opportunities for cyclodextrins in supramolecular assembly: metal organic frameworks, crystalline self-assembly, and catalyzed assembly

“…[27][28][29][30] In some cases, CDs can play the role of a ''catalyst'' in facilitating the formation of specific assembled structures. [31][32][33] In addition, although the chiral nature of CDs has long been recognized and they are widely used in chiral separations, [34][35][36] an increasing number of studies have shown that their full potential has not been explored, particularly in the development of supramolecular chiral materials. [37][38][39][40][41][42] These new findings have greatly enhanced our understanding of CDs.…”

Capillary Electrophoresis: A Three-Year Literature Review

“…In addition to these chiral pharmaceuticals, chiral CE also finds applications in various fields such as illicit drug monitoring (e.g., novel psychoactive substances 207 ), food analysis (e.g., amino acids 208 ), and environmental analysis (e.g., pesticide residue and degradation 209 ).…”