摘要
为解决巨豆三烯酮合成困难、稳定性差的问题,以α-紫罗兰酮为原料,通过还原、酯化及烯丙位氧化3步反应,合成了4种3-氧代-α-紫罗兰醇碳酸酯类巨豆三烯酮前体物,并对其合成条件进行优化;通过热重分析、在线热裂解-气相色谱-质谱联用技术和卷烟加香释放分析,对合成化合物的热解释放规律进行研究。结果表明:以Cu^(+)为催化剂,在叔丁基过氧化氢的氧化作用下,以中等至较高产率得到了目标化合物;3-氧代-α-紫罗兰醇碳酸酯的失重区间约为160~350℃;在300℃、600℃和900℃温度下,该类化合物均可裂解释放巨豆三烯酮和相应的醇类香味物质;当添加量为0.1%时,4种3-氧代-α-紫罗兰醇碳酸酯释放的巨豆三烯酮的量较空白卷烟提高约6倍;3-氧代-α-紫罗兰醇碳酸酯在受热时,会优先断裂烯丙醇酯键,脱水生成巨豆三烯酮,可增加卷烟烟气的甜润感,并有效掩盖杂气,从而提升卷烟的整体品质。
To solve the problems of difficult synthesis and poor stability of megastigmatrienone,four 3-oxo-α-ionol carbonates were synthesized as precursors of megastigmatrienone withα-ionone as the starting material via a three-step reaction of reduction,esterification,and allylic oxidation.The synthesis conditions were optimized,and the thermal release patterns of the synthesized compounds were studied by thermogravimetric analysis,online pyrolysis-gas chromatography-mass spectrometry,and cigarette flavor release analysis.The results showed that using Cu^(+)as the catalyst and TBHP as the oxidant,the target compounds were obtained in moderate to high yields.The weight loss interval of 3-oxo-α-ionol carbonates was around from 160℃to 350℃.At 300℃,600℃,and 900℃,these compounds could pyrolyze to release megastigmatrienone and corresponding alcoholic flavor substances.At an addition level of 0.1%,the release amount of megastigmatrienone from the four 3-oxo-α-ionol carbonates was 6 times higher than that of blank cigarettes.It was found that upon heating,3-oxo-α-ionol carbonates preferentially cleaved the allylic alcohol ester bond,followed by dehydration to generate megastigmatrienone.This process can enhance the sweetness and smoothness of cigarette smoke,effectively mask off-flavors,and thus improve the overall quality of cigarettes.
作者
廖付
田雨农
李庆祥
李石头
许利平
白冰
赵振杰
何文苗
LIAO Fu;TIAN Yunong;LI Qingxiang;LI Shitou;XU Liping;BAI Bing;ZHAO Zhenjie;HE Wenmiao(Technology Center,China Tobacco Zhejiang Industrial Co.,Ltd.,Hangzhou 310000,China;College of Tobacco Science and Engineering,Zhengzhou University of Light Industry,Zhengzhou 450001,China)
出处
《轻工学报》
北大核心
2025年第5期82-90,共9页
Journal of Light Industry
基金
中国烟草总公司重大科技项目(110202201053(SJ-03))
浙江中烟工业有限责任公司科技项目(ZJZY2022B003)。
