FOOD SCIENCE ›› 2012, Vol. 33 ›› Issue (20): 21-26.

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Synthesis and Thermal Degradation Property of β-ionol-β-D-glucoside

  

  • Received:2011-11-03 Revised:2012-09-13 Online:2012-10-25 Published:2012-11-09

Abstract: Reaction conditions for the synthesis of β-Ionol-β-D-glucoside by Koenigs-Knorr method were optimized in this study. The resulting products were characterized and analyzed by thermogravimetry (TG) and pyrolysis-GC/MS. The results indicated that the appropriate conditions for this glucosidation reaction were as follows: 1% freshly prepared SiO2 was added to catalyze a reaction between Br-glucose and β-ionol at a ratio of 1.5:1 in toluene allowed to proceed for 6 h at reflux temperature. FT-IR, ESI-MS and 1H-NMR analyses demonstrated that the products obtained were target products. The glucoside bonds in β-ionol-tetra-O-actyl-β-D-glucoside were broken at around 160 ℃. β-Ionol-tetra-O-actyl-β-D-glucoside and β-ionol-β-D-glucoside and β-ionol-β-D-glucoside could be pyrolyzed into several aromatic compounds such as megastigmatriene, β-ionol, β-ionone, dihydroactinidiolide, dihydroisophorone, isophorone, and 3-oxo-β-ionol. The synthesized β-ionol-β-D-glucoside was stable to heat and could be pyrolyzed into aromatic compounds upon heat, thus holding great promise for applications in the food, tobacco and medicinal industries.

Key words: β-ionol, glucoside, synthesis, thermogravimetric analysis, pyrolysis products

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