Synthesis of 4-(4-acetyl-5-methyl-1H-pyrrol-2-yl)-2′3′4′-trihydroxybutyl cinnamate and its Application in Unblended Cigarette
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TQ655

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    Abstract:

    Abstract: Under alkaline conditions in aqueous solution, 2-methyl -3-acetyl-5-1′,2′,3′,4′-tetrahydroxy butyl pyrrole were obtained by the reaction of D-glucosamine hydrochloride with acetyl acetone at reflux temperature, then take this chemical compound as raw material, reacted with cinnamic acid to synthesis the 4-(4-acetyl-5-methyl-1H-pyrrol-2-yl)-2,3,4-trihydroxybutyl cinnamate in the presence of DCC which was used as dehydrating agent. Its structure was characterized and verified by 1H NMR, 13C NMR, IR, and HRMS spectral analysis. Then the pyrolysis of the target product at 300, 600, 900°C respectively, and the application of the oil in cigarette flavoring were studied as well. The results showed that benzaldehyde, 2-methyl pyridine, farnesol and so on were detected at three temperatures. It is proved that when the target was ammount to 0.2% in tobacco, which could play an important role in enhancing the aroma quality and volume of smoke, reducing irritancy and improving the aftertaste.

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History
  • Received:December 05,2012
  • Revised:February 01,2013
  • Adopted:February 05,2013
  • Online: May 03,2013
  • Published: