食品科学 ›› 2012, Vol. 33 ›› Issue (20): 21-26.

• 工艺技术 • 上一篇    下一篇

β-紫罗兰醇-β-D-葡糖苷的合成及热解性质

孟广宇,曾世通,刘 珊,刘 洋,宋瑜冰,胡 军,何保江*   

  1. 中国烟草总公司郑州烟草研究院
  • 收稿日期:2011-11-03 修回日期:2012-09-13 出版日期:2012-10-25 发布日期:2012-11-09
  • 通讯作者: 曾世通 E-mail:shitong_zeng@yahoo.com.cn
  • 基金资助:

    Maillard反应精细化加工技术研究;紫罗兰醇类葡糖苷的合成及其裂解产物在卷烟中的释放行为研究

Synthesis and Thermal Degradation Property of β-ionol-β-D-glucoside

  • Received:2011-11-03 Revised:2012-09-13 Online:2012-10-25 Published:2012-11-09

摘要: 采用Koenigs-knorr法进行β-紫罗兰醇-β-D-葡萄苷的合成,优化反应条件,表征产物结构,并对产物进行热重分析(TG)和热裂解产物分析(Py-GC/MS)。结果表明,糖苷化反应适宜的反应条件:以新制备的SiO2担载Ag2CO3为催化剂,用量为1%;以甲苯为反应溶剂;投料比(Br-glucose-tetraacetate/β-ionol)为1.5:1;反应温度为回流温度;反应时间6h。傅里叶变换红外光谱(FT-IR)、电喷雾质谱(ESI-MS)和核磁共振氢谱(1H-NMR)的表征结果确认各产物即为目标化合物。β-紫罗兰醇-β-D-四乙酰葡糖苷的糖苷键断裂温度约为190℃、β-紫罗兰醇-β-D-葡糖苷的糖苷键断裂温度约为160℃。β-紫罗兰醇-β-D-四乙酰葡萄苷和β-紫罗兰醇-β-D-葡萄苷受热裂解能够产生巨豆三烯、β-紫罗兰醇、β-紫罗兰酮、二氢猕猴桃内酯、二氢异佛尔酮、异佛尔酮和3-氧代β-紫罗兰酮等多种香味成分。所合成的β-紫罗兰醇-β-D-葡萄苷具有良好的稳定性,而且受热能够有效释放多种香味成分,因此在食品、烟草和医药等领域具有良好的应用前景。

关键词: β-紫罗兰醇, 糖苷, 合成, 热重分析, 热裂解产物

Abstract: Reaction conditions for the synthesis of β-Ionol-β-D-glucoside by Koenigs-Knorr method were optimized in this study. The resulting products were characterized and analyzed by thermogravimetry (TG) and pyrolysis-GC/MS. The results indicated that the appropriate conditions for this glucosidation reaction were as follows: 1% freshly prepared SiO2 was added to catalyze a reaction between Br-glucose and β-ionol at a ratio of 1.5:1 in toluene allowed to proceed for 6 h at reflux temperature. FT-IR, ESI-MS and 1H-NMR analyses demonstrated that the products obtained were target products. The glucoside bonds in β-ionol-tetra-O-actyl-β-D-glucoside were broken at around 160 ℃. β-Ionol-tetra-O-actyl-β-D-glucoside and β-ionol-β-D-glucoside and β-ionol-β-D-glucoside could be pyrolyzed into several aromatic compounds such as megastigmatriene, β-ionol, β-ionone, dihydroactinidiolide, dihydroisophorone, isophorone, and 3-oxo-β-ionol. The synthesized β-ionol-β-D-glucoside was stable to heat and could be pyrolyzed into aromatic compounds upon heat, thus holding great promise for applications in the food, tobacco and medicinal industries.

Key words: β-ionol, glucoside, synthesis, thermogravimetric analysis, pyrolysis products

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