Developing ribose fatty acid mono-esters as novel oleogelators with tailored colloidal properties: enzymatic
Mengfei Xie1, Bocheng Zheng1, Bingjie Hu2
1State Key Laboratory of Bioactive Molecules and Druggability Assessment, Guangdong Basic Research Center of Excellence for Natural Bioactive Molecules and Discovery of Innovative Drugs, Institute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan University, Guangzhou 510632, China; Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM & New Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, China.
Hypothesis:
Progress on the development of novel oleogelators that effectively combine green attributes with superior colloidal properties remains limited. Since sugar mono-esters are recognized as green amphiphiles that possess intrinsic self-assembly properties, ribose-based variants are expected to serve as highly efficient oleogelators and so addressing existing deficiencies.
Experiments:
An homologous series of ribose fatty acid mono-esters (C8-C18) was prepared enzymatically and deployed as oleogelators in vegetable oil matrices derived from sunflower seeds, peanuts, camellias, olives and corn. The gelation mechanisms and structure-activity relationships were systematically investigated using a combination of rheological, X-ray diffraction and infrared spectroscopic techniques.
Findings:
Ribose mono-esters have been identified as novel oleogelators that act at concentrations as low as 2 wt% and so significantly outperforming their mainstream counterparts. The associated colloidal characteristics can be effectively tailored by modulating the length of the fatty acid residue that shifts the dominant self-assembly force from hydrogen bonding in the shorter homologs to van der Waals interactions in the longer ones. The crystalline networks formed using longer-chain esters exhibited an approximately 30-fold increase in mechanical strength and a ca. one- to two-fold enhancement in oil-binding capacity over their shorter counterparts. However, this structural enhancement compromised deformability, leading to a ca. three-fold reduction in thixotropic recovery rates. The capacity of the mono-esters to form β-polymorph crystalline networks was validated across all tested oil matrices. This study details both the gelation mechanisms and structure-activity relationships, highlighting the design principles for establishing ribose esters as next-generation oleogelators.
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