Synthesis of Structurally Well-Defined Triglyceryl Di-, Tri-, and Tetra-Fatty Acid Esters as New Oil Gelators

Abstract

We are interested in developing chemically modified linear and cyclic polyglycerols and their esters that have a single polymerization degree and fine structure. Triglyceryl di-, tri-, and tetra-fatty acid esters were synthesized from common substrate as new prominent gelators. The triglyceryl esters were capable of gelling up cooking oils. A comparison of the gelation ability of structurally related compounds clarified that the introduction of alkyl chains of suitable length is required for effective gelation.

Key words

triglycerol - fatty acid esters - gelation - aggregation - mechanistic study

References and Notes

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16

TAISET^® is the 1:1 mixture of the triglyceryl pentastearate and monoglyceryl monobehenate, which is commercially available from Taiyo Kagaku Co., Ltd
(http://www.taiyokagaku.com/).

19

All synthesized compounds were mixture of diastereomers. However, their spectral data appeared as the single structure. For example, the benzylic protons of compound 12a were observed at δ = 4.58 (4 H) and 4.59 (2 H), both as singlets (see the experimental section).