DOI: 10.12187/2025.05.010
Synthesis of megastigmatrienone precursors and their pyrolysis characteristics
LIAO Fu
TIAN Yunong
LI Qingxiang
LI Shitou
XU Liping
BAI Bing
ZHAO Zhenjie
HE Wenmiao
Abstract：To solve the problems of difficult synthesis and poor stability of megastigmatrienone,four 3-oxo-α-ionol carbonates were synthesized as precursors of megastigmatrienone with α-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.
Keywords：3-oxo-α-ionol carbonatemegastigmatrienoneprecursorcigarette flavoringpyrolysis
Publication Date：2025-10-15
Online Publishing Date：2025-10-24(First online date of this platform, not the publication date of the document)
Pages：9( 82-90 )