2,3-二氢-6-甲基-3,5-二羟基-4H-吡喃-4-酮碳酸酯的合成及热裂解  

Synthesis and pyrolysis of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one carbonates

作　　者：王清福 李蕾 赵嘉鸣 宁一博 王泽宁 席高磊 白冰 陈芝飞 WANG Qingfu;LI Lei;ZHAO Jiaming;NING Yibo;WANG Zening;XI Gaolei;BAI Bing;CHEN Zhifei(Technology Center,China Tobacco Henan Industrial Co.,Ltd.,Zhengzhou 450002,China;College of Tobacco Science and Engineering,Zhengzhou University of Light Industry,Zhengzhou 450001,China)

机构地区：[1]河南中烟工业有限责任公司技术中心,郑州450002 [2]郑州轻工业大学烟草科学与工程学院,郑州450001

出　　处：《烟草科技》2025年第4期20-25,共6页Tobacco Science & Technology

基　　金：河南中烟工业有限责任公司科技项目“吡喃酮类烟草甜味剂开发及应用技术研究”(ZW201810);河南省科技攻关项目“基于抗氧化策略的吡喃酮氧钒的合成及其抑制PTP1B活性研究”(242102310474)。

摘　　要：为解决2,3-二氢-6-甲基-3,5-二羟基-4H-吡喃-4-酮(DDMP)易氧化分解的问题,以DDMP为原料,合成了释香稳定的DDMP碳酸二酯和DDMP碳酸三酯。利用1H NMR、13C NMR和HRMS等技术确定了目标产物的结构,并通过在线裂解气相色谱-质谱连用(Py-GC-MS)技术对DDMP碳酸二酯和DDMP碳酸三酯进行了热重及热裂解分析。结果表明:①在200~300℃范围内,DDMP碳酸二酯和DDMP碳酸三酯均迅速失重,碳酸酯键断裂。②DDMP碳酸二酯和DDMP碳酸三酯的主要裂解产物是DDMP、呋喃和吡喃类化合物。③向未加香卷烟中添加DDMP碳酸二酯和DDMP碳酸三酯化合物后,卷烟主流烟气中DDMP的裂解转移率分别为4.95%和4.69%,且在90 d内裂解转移率基本保持一致。该方法可提高DDMP在卷烟中的释香稳定性。To address the challenge of easy oxidative decomposition of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one(DDMP),two stable tobacco flavor materials,DDMP carbonate diester and DDMP carbonate triester,were synthesized using DDMP as the raw material.The structure of the target products was characterized using 1H NMR,13C NMR and HRMS techniques.Thermal gravimetric and pyrolysis analyses of DDMP carbonate diester and DDMP carbonate triester were performed using on-line pyrolysis gas chromatography/mass spectrometry(Py-GC-MS)technology.The results showed that:1)Between 200-300℃,both DDMP carbonate diester and DDMP carbonate triester rapidly lost weight as a result of broken carbonate bond.2)The main decomposition products of DDMP carbonate diester and DDMP carbonate triester were DDMP,furan and pyran compounds.3)After adding DDMP carbonate diester and DDMP carbonate triester compounds to unflavored cigarettes,the transfer rates of DDMP in the mainstream smoke of the above cigarettes were 4.95%and 4.69%,respectively.In addition,the transfer rates of DDMP remained essentially the same within 90 days.This method could improve the flavor release stability of DDMP in cigarettes.

关 键 词：2 3-二氢-6-甲基-3 5-二羟基-4H-吡喃-4-酮 碳酸酯 前体化合物 热裂解 转移率 

分 类 号：TS411.2[农业科学—烟草工业]