Synthesis and Structural Characterization of Rhodinol-β-D-glucosidically bound Flavor Precursors linkage
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Abstract:
To determine a method for improving the aroma quality and strengthening the undertone, and to explore the possibility of using glycosidic flavor precursors as raw materials in thermo-flavoring, a natural identical flavor precursor in monoterpenol glycosidically bound form was synthesized and the corresponding properties were studied. For stereoselective synthesis, rhodinol with typical pure-sweet and floral notes was chosen as the main raw material to carry out the glycosylation reaction with tetra-O-acetate-α-D-glucopyranosyl bromide. Rhodinol-β-D-glucoside pentaacetate was obtained by using the modified Koenigs-Knorr reaction, and the deacetylation reaction in alkaline conditions was conducted to yield a flavor precursor with a rhodinol-β-D-glucosidic linkage. The target product was obtained after the crude products were separated and purified by preparative liquid chromatography, and its natural identical structure was confirmed by Fourier transform infrared spectroscopy (FT-IR), proton nuclear magnetic resonance (1H-NMR), and liquid chromatography–mass spectrometry (LC-MS). Finally, the content was determined to be 99.46% by reverse phase high performance liquid chromatography (RP-HPLC). The results provide important data for the stereoselective synthesis of flavor precursors with a monoterpenol-β -D-glucopyranosidic linkage as well as a method to prepare flavoring raw materials for the study of properties of glycosidic flavor precursors and their application in high-temperature-resistant foods.
