Synthesis 2008(22): 3663-3669  
DOI: 10.1055/s-0028-1083601
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Masahiro Hamada*a,b, Megumi Terayamaa, Kei-ichi Kanekoa, Tohru Ooyab, Takao Kishimotoa,b, Noriyuki Nakajima*a,b
a Department of Biotechnology, Faculty of Engineering, Toyama Prefectural University, Imizu, Toyama 939-0398, Japan
Fax: +81(766)562498; e-Mail: nori@pu-toyama.ac.jp; e-Mail: hamada@pu-toyama.ac.jp.;
b Biotechnology Research Center, Toyama Prefectural University, Imizu, Toyama 939-0398, Japan
Further Information

Publication History

Received 3 July 2008
Publication Date:
30 October 2008 (online)

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.

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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).