Formation mechanism of 2,6-dimethyl-2,6-octadienes from thermal decomposition of linalyl beta-D-glucopyranoside |
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Authors: | Hattori Shoji Kawaharada Chiami Tazaki Hiroyuki Fujimori Takane Kimura Koji Ohnishi Masao Nabeta Kensuke |
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Institution: | Analysis Research Department, Soda Aromatic Co. Ltd., 1573-4 Funakata, Noda-shi, Chiba 270-0233, Japan. |
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Abstract: | Thermally decomposed products of (+/-)-linalyl beta-D-glucoside were analyzed by GC and GC/MS. 2,6-dimethyl-2,6-octadienes produced by mild pyrolysis of linalyl beta-D-glucopyranoside under a vacuum were detected and characterized by MS and NMR spectroscopy. This suggests that 2,6-dimethyl-2,6-octadienes are produced during thermal decomposition of the glucoside via proton transfer from the anomeric position to C-6 in the aglycon moiety. A stable isotope labeling experiment directly indicated the new reaction mechanism. |
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