乙基麦芽酚丁二酸双酯的合成、热解及抗氧化研究  

Study on Synthesis,Pyrolysis and Antioxidation of Ethyl Maltol Succinate Diester

作　　者：于兆锦 张展 王海洋 王波[3] 付光明 张瑛 杨晓朋 董爱君[3] 姬小明[1] Yu Zhaojin;Zhang Zhan;Wang Haiyang;Wang Bo;Fu Guangming;Zhang Ying;Yang Xiaopeng;Dong Aijun;Ji Xiaoming(Flavors and Fragrance Engineering&Technology Research Center of Henan Province,College of Tobacco Science,Henan Agricultural University,Zhengzhou 450046;Technology Center,China Tobacco Henan Industrial Co.,Ltd.,Zhengzhou 450000;Technology Center,China Tobacco Hubei Industrial Co.,Ltd.,Wuhan 430030)

机构地区：[1]河南农业大学烟草学院河南省香精香料与调香工程技术研究中心,郑州450046 [2]河南中烟工业有限责任公司技术中心,郑州450000 [3]湖北中烟工业有限责任公司技术中心,武汉430030

出　　处：《有机化学》2024年第5期1526-1534,共9页Chinese Journal of Organic Chemistry

基　　金：湖北中烟工业有限责任公司(No.2021JSXL3JS2C032);河南农业大学博士科研资金(No.30501420)资助项目。

摘　　要：为了开发具有稳定性的焦甜香韵化合物,以丁二酸酐、香味醇和乙基麦芽酚为原料,两步法得到9种乙基麦芽酚丁二酸双酯类化合物2-乙基-4-氧代-4H-吡喃-3-基苯乙基丁二酸酯(5a)~2-乙基-4-氧代-4H-吡喃-3-基(2-甲基烯丙基)丁二酸酯(5i),并对其进行结构鉴定、热稳定性和体外抗氧化性研究.结果表明,化合物5a~5i具有焦甜香韵,同时还兼具其它香韵.化合物5a和2-乙基-4-氧代-4H-吡喃-3-基丁二酸肉桂酯(5b)最大失重率的温度高于原料的温度,热解时能产生大量乙基麦芽酚和香味醇等物质.化合物5a的1,1-二苯基-2-三硝基苯肼(DPPH)和·OH清除能力高于化合物5b~5i和乙基麦芽酚.综上所述,化合物5a具有焦甜香韵,且表现出较高的热稳定性和体外抗氧化能力,为提高香料的稳定性和拓展其多功能应用开辟了新的途径.In order to develop burnt sweet fragrance compounds with stability.In this paper,nine ethyl maltol succinate diester compounds 2-ethyl-4-oxo-4H-pyran-3-yl phenethyl succinate(5a)~2-ethyl-4-oxo-4H-pyran-3-yl(2-methylallyl)succinate(5i)were obtained by a two-step method using succinic anhydride,flavor alcohols and ethyl maltol as raw materials,and were subjected to structural characterization,thermal stability and in vitro antioxidant studies.The results showed that compounds 5a~5i possessed a burnt sweet fragrance as well as other fragrances.Compounds 5a and cinnamyl(2-ethyl-4-oxo-4H-pyran-3-yl)succinate(5b)had a highest weight loss at a temperature higher than that of raw materials,and a large amount of substances such as ethyl maltol and flavor alcohols were produced during pyrolysis.The 1,1-diphenyl-2-picrylhydrazyl(DPPH)and·OH scavenging abilities of compound 5a are higher than those of compounds 5b~5i and ethyl maltol.In summary,compound 5a has a burnt sweet fragrance,and exhibits high thermal stability and in vitro antioxidant capacity.This work may provide a new method to improve the stability of spices and expand their multifunctional application.

关 键 词：乙基麦芽酚 酯化 热裂解 抗氧化 香料香精 

分 类 号：TS264.3[轻工技术与工程—发酵工程]