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

Abstract

A novel rosin-based carbamate was prepared by the reaction of N,Ndimethylaminopropylamine 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 rosinbased cyclic carbonate. The carbamate was then quaternized to form three rosin-based carbamate group-containing quaternary ammonium salt derivatives.

Advances in Rosin-Based Chemicals: The Latest Recipes, Applications and Future Trends

“…It is noteworthy that neat rosin can be acrylated as well [125]. As an important material in rosin chemistry, acrylpimaric acid can be used for preparation of diallyl acrylpimarate [123], polyesters of acrylated rosin and polyethylene glycols [125], epoxy resins [126,127], acrylpimaryl dichloride [128,129], acrylpimaric acid amides [130], cyclic diamide [131], quaternary ammonium salts [132,133,134,135,136], calcium and zinc salts [137] as well as polyesters [138]. Moreover, it can be used directly as an epoxy curing agent [139].…”

“…It can be prepared from maleopimaric acid, epichlorohydrin and sodium hydroxide according to Scheme 2, followed by filtration, washing and evaporation [83]. It can be used in liquid epoxy resins [83], non-cytotoxic bio-based epoxypolyurethanes [162] as well as synthesis of rosin-based cyclic carbonates [132]. Similar liquid resin can be synthesized from fumaropimaric acid [122].…”

“…It can be prepared from maleopimaric acid triglycidyl ester and carbon dioxide according to Scheme 34, prior to washing and vacuum drying [132]. Its applications include synthesis of quaternary ammonium salt derivatives [132] and non-isocyanate polyurethanes [200]. Rosin-based carbamate group-containing quaternary ammonium salt derivatives are brown solids.…”

“…Rosin-based carbamate group-containing quaternary ammonium salt derivatives are brown solids. They can be prepared from rosin-based cyclic tricarbonate, N,N -dimethylaminopropylamine and alkyl bromides according to Scheme 34, and using vacuum drying and recrystallization [132]. They exhibit strong antimicrobial properties [132].…”

Synthesis, Characterization, Antimicrobial and Antitumor Activities of Sucrose Octa(N-ethyl)carbamate

“…Recently, there has been an increasing interest in the development of therapeutic compounds that are biodegradable and biocompatible, derived from plant resources and natural compound-based substances [3]. A growing number of compounds with carbamate linkages have shown strong antimicrobial and cytotoxic activities have been reported [4][5][6][7].…”