Large-scale synthesis of both symmetrical and unsymmetrical triacylglycerols containing docosahexaenoic acid

Andrews, Philip C., Fraser, Benjamin H., Junk, Peter C., Massi, Massimiliano, Perlmutter, Patrick, Thienthong, Neeranat, and Wijesundera, Chakra (2008) Large-scale synthesis of both symmetrical and unsymmetrical triacylglycerols containing docosahexaenoic acid. Tetrahedron, 64 (39). pp. 9197-9202.

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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%.

Item ID: 29622
Item Type: Article (Research - C1)
ISSN: 1464-5416
Keywords: polyunsaturated fatty-acids; structured triacylglycerols; chemoenzymatic synthesis; omega-3; lipase; omega-3-fatty-acids; interesterification; disease; retina; oil
Funders: Australian Research Council (ARC)
Date Deposited: 02 Oct 2013 10:34
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030599 Organic Chemistry not elsewhere classified @ 100%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
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