Page 162 - 《精细化工》2023年第8期

第 40 卷第 8 期 精 细 化 工 Vol.40, No.8
20 23 年 8 月 FINE CHEMICALS Aug. 2023

香精与香料
焦甜香料 2,4-二羟基-2,5-二甲基-3(2H)-

呋喃酮的制备及加香应用

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白 冰，赵明林，何 静，杨 静，张改红，杨 靖
（郑州轻工业大学 食品与生物工程学院，河南 郑州 450000）

摘要：呋喃酮经乙酰氧化反应和 Novozym435 脂肪酶脱乙酰基反应合成了 2,4-二羟基-2,5-二甲基-3(2H)-呋喃酮。
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目标产物结构经 HNMR、 CNMR 和 HRMS 确证，利用热裂解-气相色谱-质谱联用法对其在卷烟中的迁移、裂
解行为进行了模拟测定，并将其添加到卷烟中进行感官评价。结果表明，乙酰氧化反应最优条件为：呋喃酮
10 mmol、甲苯为溶剂、无水四乙酸铅为乙酰氧化试剂、n(无水四乙酸铅)∶n(呋喃酮)=3∶1、反应温度 90 ℃、
反应时间 6 h。脱乙酰基反应的最佳条件为：底物浓度为 0.8 mol/L、Novozym435 脂肪酶用量为底物质量（500 mg）
的 10%、2.8 mL 磷酸盐缓冲溶液（pH 为 8.0）为溶剂、反应温度为 40 ℃、反应时间 12 h。在上述条件下，产
物产率分别为 90%和 79%。目标产物在卷烟中以直接迁移为主，同时可裂解释放出具有焦甜香气的香味物质 2,3-
二氢-3,5-二羟基-6-甲基-4(H)吡喃-4-酮、呋喃酮、麦芽酚等；目标产物以卷烟烟丝质量的 0.002%加入到卷烟中，
可以显著提升焦甜香韵、改善口感；添加目标产物卷烟与对照卷烟烟气危害指数无显著差别，表明其在卷烟中
使用安全。
关键词：2,4-二羟基-2,5-二甲基-3(2H)-呋喃酮；焦甜香；合成；热裂解；Novozym435 脂肪酶；香精与香料
中图分类号：TS264.3 文献标识码：A 文章编号：1003-5214 (2023) 08-1776-07

Synthesis and flavoring application of caramel like

2,4-dihydroxy-2,5-dimethyl-3(2H)-furan-3-one

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BAI Bing, ZHAO Minglin, HE Jing, YANG Jing, ZHANG Gaihong, YANG Jing
（School of Food and Biological Engineering, Zhengzhou University of Light Industry, Zhengzhou 450000, Henan,
China）

Abstract: 2,4-Dihydroxy-2,5-dimethyl-3(2H)-furan-3-one was synthesized from furanone via acetyloxidation
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reaction and Novozym435 lipase deacetylation reaction, and confirmed by HNMR, CNMR and
HRMS. The product obtained was then added into cigarettes, analyzed for its migration and thermal
pyrolysis behavior by simulation using pyrolysis-gas chromatography-mass spectrometry as well as for
sensory appraisal. The results indicated that the optimal reaction conditions were 10 mmol furanone,
toluene as solvent, anhydrous lead tetraacetate as acetyloxidation reagent, n(anhydrous lead
tetraacetate)∶n(furanone)=3∶1, reaction temperature 90 ℃, reaction time 6 h, while the optimal
conditions of deacetylating reaction were as follows: substrate concentration of 0.8 mol/L, dosage of
Novozym435 lipase being 10% of substrate mass (500 mg), 2.8 mL phosphate buffer solution (pH 8.0)
as solvent, reaction temperature 40 ℃, and reaction time 12 h. Under the above conditions, the product
yields reached 90% and 79%, respectively. The target product was distributed in the cigarettes mainly
through direct migration and pyrolyzed into substances with scorching sweet aroma, such as
2,3-dihydro-3,5-dihydroxy-6-methyl-4(H)-furan-4-one, furanone, maltol and other aromatic components.
The target product was added into the cigarette with 0.002% of the mass of cut tobacco, which could

收稿日期：2023-01-06; 定用日期：2023-03-21; DOI: 10.13550/j.jxhg.20230016
基金项目：河南省科技攻关计划项目（192102110212）
作者简介：白 冰（1982—），男，讲师，E-mail：baibing82@163.com。联系人：杨 靖（1972—），男，教授，E-mail：13623810925@
126.com。