JOURNAL OF LIGHT INDUSTRY

CN 41-1437/TS  ISSN 2096-1553

Volume 40 Issue 5
October 2025
Article Contents
LIAO Fu, TIAN Yunong, LI Qingxiang, et al. Synthesis of megastigmatrienone precursors and their pyrolysis characteristics[J]. Journal of Light Industry, 2025, 40(5): 82-90. doi: 10.12187/2025.05.010
Citation: LIAO Fu, TIAN Yunong, LI Qingxiang, et al. Synthesis of megastigmatrienone precursors and their pyrolysis characteristics[J]. Journal of Light Industry, 2025, 40(5): 82-90. doi: 10.12187/2025.05.010 shu

Synthesis of megastigmatrienone precursors and their pyrolysis characteristics

  • 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.
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