Synthesis, characterization, antibacterial and antifungal activities of 1-O-alkylglycerols

1-O-alkylglycerols are a class of natural existing lipids with broad biological activities. However, their use in food or agricultural fields remains to be investigated, especially for their antimicrobial activity. In this work, three 1-O-alkylglycerols, 1-O-octanylglycerol (C₈Gly₁), 1-O-dodecylglycerol (C₁₂Gly₁), and 1-O-hexadecylglycerol (C₁₆Gly₁), were synthesized in the isolated yields of 71.3-89.8 % and characterized by ¹H NMR, ¹³C NMR, FITR, mass spectra, and HPLC-ESLD. The critical micelle concentration (CMC) of 1-O-alkylglycerols was determined to be 1.65 mmol/L (C₈Gly₁), 0.33 mmol/L (C₁₂Gly₁), and 0.23 mmol/L (C₁₆Gly₁) using the pyrene method. C₁₂Gly₁ and C₁₆Gly₁ had similar surface tensions that are lower than C₈Gly₁. C₈Gly₁ can form micelles in aqueous solution with excellent nano-dispersed uniformity and stability. Furthermore, C₈Gly₁ and C₁₂Gly₁ not only displayed good antibacterial activity against Staphylococcus aureus, but they also inhibited the growth of Botryosphaeria dothidea, Monilia fructigena, and Phytophthora capsicum at 400 μg/mL. Thus, the C₈Gly₁ and C₁₂Gly₁ can serve as novel antimicrobial agents in food preservation.