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 (C(8)Gly(1)), 1-O-dodecylglycerol (C(12)Gly(1)), and 1-O-hexadecylglycerol (C(16)Gly(1)), were synthesized in the isolated yields of 71.3–89.8 % and characterized by (1)H NMR, (13)C NMR, FITR, mass spectra, and HPLC-ESLD. The critical micelle concentration (CMC) of 1-O-alkylglycerols was determined to be 1.65 mmol/L (C(8)Gly(1)), 0.33 mmol/L (C(12)Gly(1)), and 0.23 mmol/L (C(16)Gly(1)) using the pyrene method. C(12)Gly(1) and C(16)Gly(1) had similar surface tensions that are lower than C(8)Gly(1). C(8)Gly(1) can form micelles in aqueous solution with excellent nano-dispersed uniformity and stability. Furthermore, C(8)Gly(1) and C(12)Gly(1) 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 C(8)Gly(1) and C(12)Gly(1) can serve as novel antimicrobial agents in food preservation.