Preparation, Characterization and Antibacterial Activity of 1-Monoacylglycerol of Adamantane-1-Carboxylic Acid
Article first published online: 5 NOV 2012
© 2012 Wiley Periodicals, Inc.
Journal of Food Biochemistry
Volume 37, Issue 5, pages 544–553, October 2013
How to Cite
Doležálková, I., Janiš, R., Buňková, L., Slobodian, P. and Vícha, R. (2013), Preparation, Characterization and Antibacterial Activity of 1-Monoacylglycerol of Adamantane-1-Carboxylic Acid. Journal of Food Biochemistry, 37: 544–553. doi: 10.1111/jfbc.12005
- Issue published online: 7 OCT 2013
- Article first published online: 5 NOV 2012
- Manuscript Accepted: 24 MAY 2012
- Ministry of Education, Youth and Sports of the Czech Republic. Grant Number: MSMT 7088352101
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 1,000–1,500 μg/mL is able to effectively suppress the growth of Gram-positive bacteria; Gram-negative species were less sensitive.
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.