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

• Published in: Journal of applied glycoscience : JAG Vol. 66; no. 3; p. 103
• Main Authors: Kajiki, Takahito, Komba, Shiro
• Format: Journal Article
• Language: Japanese
• Published: Tsukuba Japan Science and Technology Agency 01.01.2019
• Subjects: Alcohol; Alcohols; Atomic properties; Carbon; Chemical synthesis; Derivatives; Fatty acids; Fibrous structure; Fructose; Gelation; Mannitol; Nitrogen atoms; Oils & fats; Physical properties; Starch; Sugar
• ISSN: 1344-7882; 1880-7291
• DOI: 10.5458/jag.jag.JAG-2019_0011

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.