Catalyzed Interesterification of Mixed Short & Medium Chain Fatty Acid Triacylglycerols as a Potential Dietary Food Lipid Source: Synthesis and Characterization

Ronald P. D’Amelia^1, , Gabrielle Cabrera¹, Ling Huang¹ and William F. Nirode¹

¹Department of Chemistry, Hofstra University, Hempstead New York, USA

Cite this paper:
Ronald P. D’Amelia, Gabrielle Cabrera, Ling Huang and William F. Nirode. Catalyzed Interesterification of Mixed Short & Medium Chain Fatty Acid Triacylglycerols as a Potential Dietary Food Lipid Source: Synthesis and Characterization. American Journal of Food Science and Technology. 2017; 5(6):228-232. doi: 10.12691/ajfst-5-6-1

Abstract

Interesterifcation reactions, more commonly called ester-exchange, are a process by which the arrangement of fatty acids in the triacylglycerol molecule is changed. Ester-exchange reactions lead to a random distribution of fatty acids resulting in a triacylglycerol composition that is predictable from the overall fatty acid composition of the starting reaction mixture. In this report, we synthesized various triacylglycerols containing different ratios of saturated short chain fatty acids (SCFA) such as: acetic, propionic and butyric, with a saturated medium chain fatty acid (MCFA) of octanoic acid. The interesterification of these triacylglycerols was prepared by the NaOCH₃ catalyzed interesterification of model reactions performed with different molar ratios of Triacetin, Tripropionin, Tributyrin and Trioctanoin. The reaction products were characterized by Gas Chromatography (GC) and Proton NMR. We found that the difference in fatty acid size and the reduced steric demands of the S/MCFA did not give rise to positional specificity and we found no observable deviations from the random interesterification chemistry model. The potential of having different short and medium fatty acids triacylglycerol on one molecule for direct ingestion and metabolism can be of significant importance to maintaining gut health.

Keywords:
interesterification triacylglycerols triglycerides short chain fatty acids medium chain fatty acids ester-exchange randomization theory

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