Preparation, characterization and antibacterial activity of 1-monoacylglycerol of adamantane-1-carboxylic acid

Abstract

A nontraditional monoacylglycerol, 1-monoacylglycerol of adamantane-1-carboxylic acid (2,3-dihydroxypropyl adamantane-1-carboxylate), has been prepared using the direct addition of adamantane-1-carboxylic acid to glycidol. Several reaction conditions were examined in order to improve the reaction yield. Based upon the results of these experiments, the following conditions were recommended: glycidol at 80% molar excess, molar ratio of the adamantane-1-carboxylic acid and toluene as a solvent 1:10, chromium (III) acetate hydroxide as a catalyst (0.5% w/w), 96C. Final reaction product with conversion higher than 98% was further analyzed using high-performance liquid chromatography, gas chromatography-mass spectrometry, nuclear magnetic resonance analysis and differential scanning calorimetry. The effect exhibited by 2,3-dihydroxypropyl adamantane-1-carboxylate against important species of Gram-positive and Gram-negative bacteria was assessed. Results showed that 2,3-dihydroxypropyl adamantane-1-carboxylate at concentrations 1,000-1,500μg/mL is able to effectively suppress the growth of Gram-positive bacteria; Gram-negative species were less sensitive. Practical Applications: Monoacylglycerols and their derivatives are widely used emulsifiers in the food and cosmetic industry. Besides emulsifying properties, monoacylglycerols with a broad spectrum of microbicidal activity could have beneficial effect by reducing the undesirable microbial flora and extending the shelf life in food or cosmetic products. The aim of this study is to find a suitable antimicrobial agent that could be used as part of food packaging materials and food foils. © 2012 Wiley Periodicals, Inc.