Synthesis of α-ionyl-β-d-glucoside and its property of flavor release

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• 作者：Shitong Zeng (1)
  Shihao Sun (1)
  Shan Liu (1)
  Jun Hu (1)
  Baojiang He (1)
  
• 关键词：α ; Ionol ; β ; d ; glucoside ; Synthesis ; TG ; Py ; GC/MS ; Pyrolysis products ; Flavor release
• 刊名：Journal of Thermal Analysis and Calorimetry
• 出版年：2014
• 出版时间：February 2014
• 年：2014
• 卷：115
• 期：2
• 页码：1049-1056
• 全文大小：1,763 KB
• 作者单位：Shitong Zeng (1)
  Shihao Sun (1)
  Shan Liu (1)
  Jun Hu (1)
  Baojiang He (1)
  
  1. Zhengzhou Tobacco Research Institute of CNTC, Zhengzhou, 450001, People’s Republic of China
  
• ISSN：1572-8943

文摘

A flavor precursor α-ionyl-β-d-glucoside (IG) was synthesized by Koenigs–Knorr method, and its structure was characterized by proton nuclear magnetic resonance spectroscopy, Fourier transform-infrared spectroscopy, and electro spray ionization mass spectroscopy (MS). Thermal degradation behaviors of the intermediate α-ionyl-tetra-O-acetyl-β-d-glucoside (IAG) and IG were analyzed by thermogravimetry and online pyrolysis (Py)-gas chromatography–MS. Flavor release property of IG was investigated with cigarettes as the carrier. The results indicated that fracture temperature of glycosidic bond was about 200?°C for IAG, and was about 190?°C for IG. Py of IAG and IG could generate several aroma compounds such as megastigmatriene, α-ionol, α-ionone, and 3-oxo-α-ionol. IG added in cigarettes could be pyrolyzed to release α-ionol, α-ionone, and 3-oxo-α-ionone, and increase the release amount of megastigmatrienone in mainstream smoke during smoking. The release amount of characteristic flavor components in mainstream smoke remain stable after the cigarette sample with IG placed in standard condition for 30?days, and there was no significant difference in the single puff release amounts, which confirmed the flavor release stability and uniformity of IG under heating treatment.