Synthesis and pyrolysis transfer rate of isoeugenol-β-D-glucopyranoside
Isoeugenol-2,3,4,6-tetra-O-acetyl-β-D-glucoside(Ⅲ)were synthesized from acetylbromide-α-D-glucose(Ⅰ)and isoeugenol(Ⅱ)through phase transfer catalysis and ionic liquid catalysis.Compound(Ⅲ)deacetylated in sodium methoxide to obtain isoeugenol-β-D-glucoside(Ⅳ).CompoundⅣ was added into cigarette and its transfer rate in the particle phase of cigarette mainstream smoke was analyzed.The results showed that the ionic liquid catalysis method(yield 56.8%)was superior to the phase transfer catalysis method(yield 43.5%).The reaction conditions of the ionic liquid catalytic method were as follows:1-butyl-3-methylimidazolium bromide as catalyst,chloroform as solvent,sodium hydroxide aqueous solution as acid binding agent,n(Ⅰ)∶n(Ⅱ)= 0.8∶1,n(Ⅰ)∶n(1-butyl-3-methylimidazolium bromide)= 1∶1,room temperature,and reaction time 8 h.Under the above-mentioned conditions,the yield of compound Ⅲ was 56.8%.Compound Ⅳ with a yield of 87.6%was obtained from compound Ⅲ reacted in sodium methoxide/methanol solution by removing the tetraacetyl group.During cigarette smoking,the transfer rate of isoeugenol from the thermal decomposition of compound Ⅳ to the mainstream smoke particle phase was 3.2%.
ionic liquidsphase transfer catalysisglycosylationisoeugenol-β-D-glucosidepyrolysis transfer rateperfumes and essences
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