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Large-scale synthesis of both symmetrical and unsymmetrical triacylglycerols containing docosahexaenoic acid
Authors:Philip C. Andrews  Peter C. Junk  Patrick Perlmutter  Chakra Wijesundera
Affiliation:a Monash University, School of Chemistry, Wellington Road, Clayton, Victoria 3800, Australia
b CSIRO Food Futures National Research Flagship and Food Science Australia, 671 Sneydes Road, Werribee, Victoria 3030, Australia
Abstract:A large-scale (∼100 g) synthesis of symmetrical and unsymmetrical triacylglycerols containg docosahexaenoic acid (D) and two of either lauric (L), palmitic (P) or stearic acid (S) is described. Key improvements in purification of synthetic intermediates, in addition to a more efficient acetonide cleavage reaction affords the six TAGs (LaDLa, LaLaD, PDP, PPD, SDS, SSD) in yields of 80-90% and in regioisomeric purities greater than or equal to 90%.
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