Formation mechanism of 2,6-dimethyl-2,6-octadienes from thermal decomposition of linalyl beta-D-glucopyranoside.
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.
Hattori
Shoji
S
Analysis Research Department, Soda Aromatic Co. Ltd., 1573-4 Funakata, Noda-shi, Chiba 270-0233, Japan.
Kawaharada
Chiami
C
Tazaki
Hiroyuki
H
Fujimori
Takane
T
Kimura
Koji
K
Ohnishi
Masao
M
Nabeta
Kensuke
K
D000475:Alkenes / Q000737:chemistry; D005960:Glucosides / Q000737:chemistry; D006358:Hot Temperature; D039821:Monoterpenes / Q000737:chemistry*; D009795:Octanes / Q000737:chemistry*
D000475:Alkenes; D005960:Glucosides; D039821:Monoterpenes; D009795:Octanes