Development of Novel Low-Molecular-Mass Oil-gelling Agents: Synthesis and Physical Properties of 1,5-Anhydro-D-glucitol and 1,5-Anhydro-D-mannitol Protected with Saturated Linear Fatty Acids.

Content Provider	Europe PMC
Author	Kajiki, Takahito Komba, Shiro
Abstract	We have developed a novel low-molecular-mass oil-gelling agent that is electrically neutral, has no nitrogen atoms and consists only of cyclic sugar alcohols and saturated linear fatty acids. The cyclic sugar alcohols were 1,5-anhydro-D-glucitol (1,5-AG) and 1,5-anhydro-D-mannitol (1,5-AM) derived from starch via 1,5-anhydro-D-fructose. Various saturated linear fatty acids with 10 to 18 and 22 carbon atoms were introduced into all the hydroxy groups of 1,5-AG. Various saturated linear fatty acids with 13 to 18 and 22 carbon atoms were introduced into all the hydroxy groups of 1,5-AM. Initially, the gelling ability increased as the carbon number increased, but the gelling ability decreased as the carbon number increased beyond 17 carbons. This trend was similar for both 1,5-AG and 1,5-AM. A comparison of 1,5-AG and 1,5-AM derivatives revealed that 1,5-AG derivatives had greater gelling abilities for different kinds of oils at the same fatty acid length. Further, it was confirmed by SEM observations that a three-dimensional fibrous structure was formed, and this network structure formed the gel and held the oil. Here, we report the synthesis and characteristics of a novel low-molecular-weight gelling agent and its gelation mechanism.
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ISSN	13447882
Volume Number	66
PubMed Central reference number	PMC8373582
Issue Number	3
PubMed reference number	34429688
Journal	Journal of Applied Glycoscience [J Appl Glycosci (1999)]
e-ISSN	18807291
DOI	10.5458/jag.jag.jag-2019_0011
Language	English
Publisher	The Japanese Society of Applied Glycoscience
Publisher Date	2019-08-28
Publisher Place	Tokyo, JAPAN
Access Restriction	Open
Rights License	This is an open-access paper distributed under the terms of the Creative Commons Attribution Non-Commercial (by-nc) License (CC-BY-NC4.0: https://creativecommons.org/licenses/by-nc/4.0/). 2019 by The Japanese Society of Applied Glycoscience
Subject Keyword	oil-gelling agents 1,5-anhydro-D-glucitol 1,5-anhydro-D-mannitol fibrous structure
Content Type	Text
Resource Type	Article
Subject	Biochemistry, Genetics and Molecular Biology