title: Biobased Fat Mimicking Molecular Structuring Agents for Medium-Chain Triglycerides (MCTs) and Other Edible Oils.
abstract: To develop sustainable value-added materials from biomass, novel small-molecule sugar ester gelators were synthesized using biocatalysis. The facile one-step regiospecific coupling of the pro-antioxidant raspberry ketone glucoside and unsaturated or saturated long- and medium-chain fatty acids provides a simple approach to tailor the structure and self-assembly of the amphiphilic product. These low molecular weight molecules demonstrated the ability to self-assemble in a variety of solvents and exhibited supergelation, with a minimum gelation concentration of 0.25 wt %, in numerous organic solvents, as well as in a range of natural edible oils, specifically a relatively unstudied group of liquids: natural medium-chain triglyceride oils, notably coconut oil. Spectroscopic analysis details the gelator structure as well as the intermolecular noncovalent interactions, which allow for gelation. X-ray diffraction studies indicate fatty acid chain packing of gelators is similar to that of natural fats, signifying the crystalline nature may lead to desirable textural properties and mouthfeel.
authors.affiliation: Department of Chemistry and Center for Discovery and Innovation (CDI), The City College of New York , 85 St. Nicholas Terrace, New York, New York 10031, United States.|Ph.D. Program in Chemistry, The Graduate Center of the City University of New York , New York, New York 10016, United States.
authors.forename: Julian R
authors.initials: JR
authors.lastname: Silverman
authors.affiliation: Department of Chemistry and Center for Discovery and Innovation (CDI), The City College of New York , 85 St. Nicholas Terrace, New York, New York 10031, United States.|Ph.D. Program in Chemistry, The Graduate Center of the City University of New York , New York, New York 10016, United States.
authors.forename: George
authors.initials: G
authors.lastname: John
mesh_terms: D000074263:Coconut Oil; D005227:Fatty Acids / Q000737:chemistry; D008970:Molecular Weight; D010938:Plant Oils / Q000737:chemistry*; D014280:Triglycerides / Q000737:chemistry*; D014961:X-Ray Diffraction
chemical_list: D005227:Fatty Acids; D010938:Plant Oils; D014280:Triglycerides; D000074263:Coconut Oil
keywords: coconut oil; medium-chain triglycerides (MCTs); molecular gelators; oleogels; supergelators