Preparation and Antimicrobial Activity of Rosin-based Carbamate Group-containing Quaternary Ammonium Salt Derivatives

Guifeng Liu, Caifeng Chen, Guomin Wu, Zhenwu Kong

Abstract


A novel rosin-based carbamate was prepared by the reaction of N,N-dimethylaminopropylamine with rosin-based cyclic carbonate. Using LiBr in conjunction with ethylene glycol as a catalyst, carbon dioxide was treated with triglycidyl ester of maleopimaric acid to prepare the rosin-based cyclic carbonate. The carbamate was then quaternized to form three rosin-based carbamate group-containing quaternary ammonium salt derivatives. The chemical structures of all new compounds were characterized by IR, 1H NMR, and 13C NMR. The antimicrobial activities of the carbamate and quaternary ammonium salt derivatives were investigated. The bioassay test results showed that all derivatives exhibited strong inhibition against Staphylococcus aureus, Escherichia coli, Bacillus subtilis, Bacillus thuringiensis, and Streptomyces microflavus. However, no visible antifungal activity was found against Saccharomyces cerevisiae or Aspergillus niger, except for the activity of the carbamate derivative against S. cerevisiae.

Keywords


Rosin; Cyclic carbonate; Carbamate; Quaternary ammonium salt; Antibacterial activity

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