Synthesis, Pyrolysis, and Antioxidant Activity of Phenylalkenal Odorants

doi:10.6023/cjoc202603005

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苯基烯醛呈香物质的合成、热解及其抗氧化活性研究

许嘉龙^a, 王旭锋^b, 岳亭廷^a, 李媛媛^a, 姬小明^a,*, 程彪^a,*

^a河南农业大学烟草学院郑州 450046;
^b陕西中烟工业有限责任公司技术中心西安 710065

收稿日期:2026-03-04 修回日期:2026-04-24
基金资助:
国家自然科学基金(No. 22301063)、河南农业大学拔尖人才基金(No. 30501288)资助项目.

Synthesis, Pyrolysis, and Antioxidant Activity of Phenylalkenal Odorants

Xv Jialong^a, Wang Xufeng^b, Yue Tingting^a, Li Yuanyuan^a, Ji Xiaoming^a,*, Cheng Biao^a,*

^aCollege of Tobacco Science, Henan Agricultural University, Zhengzhou, 450046;
^bTechnology Center, China Tobacco Shaanxi Industrial Co., Ltd., Xi'an, 710065

Received:2026-03-04 Revised:2026-04-24
Contact: *E-mail: xiaomingji@henau.edu.cn; chengbiao@henau.edu.cn
Supported by:
National Natural Science Foundation of China (No. 22301063), and the Top-Notch Personnel Fund of Henan Agricultural University (No. 30501288).

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Abstract

Phenylalkenal compounds, due to the presence of aroma-contributing groups such as aromatic rings and aldehyde groups in their molecular structure, are a key class of odorants with significant applications in the flavor and fragrance industry. A series of six novel phenylalkenals were synthesized via a cross-aldol condensation of phenylacetaldehyde with various alkyl aldehydes using sodium acetate as a base in anhydrous ethanol. The resulting compounds were characterized by nuclear magnetic resonance (¹H NMR, ¹³C NMR), infrared spectroscopy (IR), and high-resolution mass spectrometry (HRMS). Their odor characteristics were evaluated by a sensory panel. Their thermal behaviors were analyzed by thermogravimetry-derivative thermogravimetry (TG-DTG), and pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS). TG-DTG analysis determined the temperature range corresponding to 90% mass loss and the temperature at the maximum mass loss rate for each compound. The results revealed that, with the exception of compound 3d, the other five compounds satisfied the volatility requirements for flavor compounds in heat-not-burn (HNB) cigarettes. Additionally, Py-GC/MS studies at 400 °C showed that all six compounds underwent partial pyrolysis, generating various aromatic products that contribute to flavor profiles. The antioxidant evaluation revealed that all six compounds exhibited significant antioxidant activity. Notably, 3c demonstrated the strongest scavenging capacity toward ABTS⁺•, while 3e showed the highest scavenging efficiency against DPPH•. This study provides new candidate compounds for the development of novel flavor substances, particularly those suitable for HNB cigarettes, with promising potential in areas such as tobacco product formulation and food additives.

Key words: aldol condensation, phenylalkenal, flavor and fragrance, thermal behavior, antioxidation

Cite this article

Xv Jialong, Wang Xufeng, Yue Tingting, Li Yuanyuan, Ji Xiaoming, Cheng Biao. Synthesis, Pyrolysis, and Antioxidant Activity of Phenylalkenal Odorants[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202603005.

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苯基烯醛呈香物质的合成、热解及其抗氧化活性研究

Synthesis, Pyrolysis, and Antioxidant Activity of Phenylalkenal Odorants

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