Interesterification and trans esterification are traditional techniques that have been applied to lipid chemistry. Chemical interesterification can be defined as a random redistribution of the fatty acid moieties present in a triglyceride oil over its glycerol moieties.<br/>Interesterification was applied to produce a family of low calorie fats known as Salatrim which are  triaclyglycerols containing short and long chain fatty acids.  These fats have been commercialized as low-calorie fat substitutes, emulsifiers, moisture barriers and encapsulating agents.  As the technology has developed, a model system was established to predict the triglyceride distribution of  interesterified  triglycerides. The ability to quantitatively predict the ensemble of TAG structures that arise by random interesterification (RIE) involves nothing more than full application of the statistical equations that reside in the literature. Once developed and tested, spreadsheets can provide a most convenient tool to predict TAG compositions at a highly granular level. Correlation of these predictions to experiment required simultaneous development of analytical tools and strategies that had the capability to resolve complex product mixtures. NMR, High Temperature Gas Chromatography (HTGC) coupled with Mass Spectrometry (MS) proved to be useful helping correlate individual isomeric structures with theory.<br/>Using short chain fatty acid models, the weight % of the triesters found were compared to the amount predicted using the statistical randomized interesterification reaction model. Differences in fatty acid size and the reduced steric demands of the SCFA did not result in  observable deviations from the random interesterification model.<br/>The technology has now been applied to produce unique glycerides with targeted fatty acids for a range of applications.  Delivery of omega-3 fatty acids to produce useful triglycerides delivering nutritional benefits and useful functionality in foods. Bioactive small acids such as pyruvate have been appended to triacyl glycerol’s to become a delivery system for pyruvate in dietary or medical applications.

The evolution of interesterified lipids from curiosity to designer lipids for food and pharma application

255th National Meeting (2018)

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