4–甲基愈创木酚–β–D–葡萄糖苷的合成及其在卷烟加香中的应用研究
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中国烟草总公司重大科技项目(110202201053(SJ–03));河南省科技攻关计划项目(192102110212);郑州轻工业大学校基础研究基金项目(23XJCYJ032)


Synthesis of 4-methylguaiacol-β-D-glucoside and its application in cigarettes flavoring
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    摘要:

    为了开发热稳定及释香稳定型烟用香料,采用离子液体催化法合成4–甲基愈创木酚–β–D–葡萄糖苷,对合成的4–甲基愈创木酚–β–D–葡萄糖苷进行热稳定及热裂解分析,并考察其加入卷烟后向主流烟气粒相中释放4–甲基愈创木酚的情况。结果表明:以1–丁基–3–甲基–溴化咪唑鎓为离子液体催化剂,合成了4–甲基愈创木酚–2, 3, 4, 6–四–O–乙酰基–β–D–葡萄糖苷,收率为49.3%;脱去乙酰基,得到4–甲基愈创木酚–β–D–葡萄糖苷,收率为87.3%;热重–微商热重(TG–DTG)分析表明4–甲基愈创木酚–β–D–葡萄糖苷的热稳定性优于4–甲基愈创木酚;热裂解–气相色谱–质谱(Py–GC–MS)分析表明4–甲基愈创木酚–β–D–葡萄糖苷在300、600、900 ℃的主要裂解产物均为4–甲基愈创木酚;烟丝加香方式和卷烟纸加香方式下烟气中4–甲基愈创木酚的释放量不同,加香效果不同;添加4–甲基愈创木酚–β–D–葡萄糖苷的加香卷烟燃吸时能释放4–甲基愈创木酚,并且释香更均匀、逐口稳定性更好,效果优于添加4–甲基愈创木酚的;推测4–甲基愈创木酚–β–D–葡萄糖苷可能是一种释香稳定的香料前体。

    Abstract:

    In order to develop thermal and aroma stable tobacco flavorings, 4-methylguaiacol-β-D-glucoside was synthesized using ionic liquid catalytic method, the synthesized 4-methylguaiacol-β-D-glucoside was subjected to thermal stability and pyrolysis analysis, and added to cigarettes to investigate the release of 4-methylguaiacol into mainstream smoke particles. The results showed that 1-Butyl-3-methyl-imidazonium bromide was selected as an ionic liquid catalyst to synthesize 4-methylguaiacol-2,3,4,6-tetra-O-acetyl-β-D-glucoside with a yield of 49.3%. The target 4-methylguaiacol- β-D-glucoside was obtained by deacetylation of 4-methylguaiacol-2,3,4,6-tetra-O-acetyl-β-D-glucoside with a yield of 87.3%. The thermal stability of 4-methylguaiacol-β-D-glucoside was found to be superior to that of 4-methylguaiacol using the thermogravimetric analysis (TG-DTG). Through pyrolysis gas chromatography-mass spectrometry (Py-GC-MS) technology, it was shown that the main cracking product of 4-methylguaiacol-β-D-glucoside at 300, 600 and 900 ℃ was 4-methylguaiacol. The release amount of 4-methylguaiacol in smoke is different between the tobacco flavoring method and the cigarette paper flavoring method, resulting in different flavoring effects. Flavored cigarettes added with 4-methylguaiacol-β-D-glucoside can release 4-methylguaiacol during smoking, and the release of fragrance is more uniform, with better stability per bite, and the effect is better compared to 4-methylguaiacol addition. We speculate that 4-methylguaiacol-β-D-glucoside can be a stable fragrance precursor.

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张改红,杜帅,许航,徐月莹,石栋栋,毛多斌*.4–甲基愈创木酚–β–D–葡萄糖苷的合成及其在卷烟加香中的应用研究[J].湖南农业大学学报(自然科学版),2025,51(2):16-23.

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  • 在线发布日期: 2025-05-08
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