Synthesis and characterization of bio-based quaternary ammonium salts with gibberellate or l-tryptophanate anion

• Published in: Monatshefte für Chemie Vol. 151; no. 9; pp. 1365 - 1373
• Main Authors: Szymaniak, Daria, Pernak, Juliusz, Rzemieniecki, Tomasz, Kaczmarek, Damian Krystian, Andrzejak, Roman, Kosiada, Tomasz, Janowska, Beata
• Format: Journal Article
• Language: English
• Published: Vienna Springer Vienna 2020; Springer Nature B.V
• Subjects: Ammonium hydroxide; Analytical Chemistry; Anions; Biological activity; Biological properties; Biosynthesis; Cations; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Choline; Gibberellic acid; Gibberellins; Growth regulators; Hydroxides; Inorganic Chemistry; Metathesis; Organic Chemistry; Original Paper; Phase transitions; Physical Chemistry; Plant growth; Quaternary ammonium salts; Theoretical and Computational Chemistry; Tryptophan; Ionic liquids; Bioorganic chemistry; Plant growth regulators; Natural compounds; Phytochemistry
• ISSN: 0026-9247; 1434-4475
• DOI: 10.1007/s00706-020-02672-9

Numerous biologically active acids can be transformed into an ionic form in a facile way and combined with appropriate quaternary ammonium cation to improve their application properties or biological activity. This study describes the synthesis of new quaternary ammonium salts with anions of gibberellic acid, a common plant growth regulator from the gibberellin group, or l -tryptophan, an important precursor of auxin biosynthesis. The surface-active tetrapentylammonium ion and natural substances such as acetylcholine, choline, and quinine were the sources of cations. Novel salts of gibberellic acid and l -tryptophan were obtained with high yields exceeding 97% as a result of the metathesis reaction or the neutralization of quaternary ammonium hydroxides. Phase transition temperatures, thermal and chemical stability, and solubility in solvents with different polarities were determined for all obtained salts. On the basis of studies regarding the influence of synthesized salts on the post-harvest longevity and quality of leaves of Convallaria majalis , it was established that the biological activity of the natural plant regulators in most cases was maintained. Therefore, it can be concluded that the conversion of the active substance into the form of a quaternary ammonium salt results in obtaining novel forms of plant growth regulators with favourable physicochemical properties while maintaining the efficacy of the biological active ingredients. Graphic abstract