Stability of Guaiacol‐β‐D‐Glucoside and Its Application in Cigarettes Flavoring

doi:10.15933/j.cnki.1004-3268.2025.05.019

Abstract

Abstract: To investigate the availability of guaiacol‐β‐D‐glucoside in cigarette flavoring，a comparative study was conducted on the light stability，thermal stability，thermal cracking behavior and cigarette flavoring application effects of guaiacol and guaiacol‐β‐D‐glucoside. The results showed that the light stability and thermal stability of guaiacol‐β‐D‐glucoside were significantly higher than those of guaiacol；The main thermal decomposition product of guaiacol‐β‐D‐glucoside at different temperatures was guaiacol；Guaiacol‐β‐D‐glucoside in cigarettes had different flavoring effects with different flavoring methods，and the release of guaiacol in mainstream smoke of cigarettes with cut tobacco flavoring method was higher than that of cigarette paper flavoring. Under the tobacco flavoring method，whether it was traditional cigarettes or heated cigarettes，the release amount of guaiacol in the particulate phase of mainstream cigarette smoke with guaiacol‐β‐D‐glucoside addition（traditional cigarettes：16.13 μg/cig；heated cigarettes：6.61 μg/cig）were lower than that of guaiacol addition（traditional cigarette：38.97 μg/cig；heated cigarette：21.47 μg/cig）.However，the uniformity and stability of guaiacol‐β‐D‐glucoside added cigarettes were better than those of guaiacol.Therefore，guaiacol‐β‐D‐glucoside is a stable and uniformly released flavoring precursor，which has certain advantages when used in traditional cigarettes and heated cigarettes.

Key words: Cigarette flavoring, Heated cigarette, Guaiacol?β?D?glucoside, Stability, Thermal cracking

摘要： 为研究愈创木酚-β-D-葡萄糖苷在卷烟加香中的可用性，对愈创木酚和愈创木酚-β-D-葡萄糖苷的光稳定性、热稳定性、热裂解行为、卷烟加香应用效果进行对比研究。结果表明，愈创木酚-β-D-葡萄糖苷的光稳定性和热稳定性均明显高于愈创木酚；愈创木酚-β-D-葡萄糖苷在不同温度下的主要热裂解产物均为愈创木酚；愈创木酚-β-D-葡萄糖苷在卷烟中的加香方式不同，加香效果存在差异，烟丝加香方式下卷烟主流烟气中愈创木酚的释放量高于卷烟纸加香；烟丝加香方式下，不论是传统卷烟还是加热卷烟，添加愈创木酚-β-D-葡萄糖苷的卷烟主流烟气粒相中愈创木酚的释放量（传统卷烟：16.13 μg/支；加热卷烟：6.61 μg/支）均低于添加愈创木酚的卷烟（传统卷烟：38.97 μg/支；加热卷烟：21.47 μg/支），但添加愈创木酚-β-D-葡萄糖苷的卷烟释香均匀性和稳定性均优于愈创木酚。因此，愈创木酚-β-D-葡萄糖苷是一种稳定性及释香均匀性均较好的香料前体物，将其用于传统卷烟及加热卷烟具有一定的优势。

关键词: 卷烟加香, 加热卷烟, 愈创木酚-β-D-葡萄糖苷, 稳定性, 热裂解

CLC Number:

ZHANG Gaihong, XU Hang, DU Shuai, XU Yueying, SHI Dongdong, XUE Jingjing, WANG Mengyao, MAO Duobin. Stability of Guaiacol‐β‐D‐Glucoside and Its Application in Cigarettes Flavoring[J]. Journal of Henan Agricultural Sciences, 2025, 54(5): 172-180.

张改红, 许航, 杜帅, 徐月莹, 石栋栋, 薛晶晶, 王梦瑶, 毛多斌. 愈创木酚-β-D-葡萄糖苷的稳定性及其在卷烟加香中的应用[J]. 河南农业科学, 2025, 54(5): 172-180.

Figures/Tables 11

References

［1］王林，朱金峰，许自成，等.烟草中糖苷类物质研究进展［J］. 中国农业科技导报，2015，17（1）：65‑70.

WANG L，ZHU J F，XU Z C，et al. Research progress on tobacco glycoside substances［J］. Journal of Agricultural Science and Technology，2015，17（1）：65‑70.

［2］卢梦梦. 焦甜香潜香物质糖苷化合物的合成［D］. 合肥：合肥工业大学，2016.

LU M M. Synthesis of glycoside compounds as sweet flavor precurors ［D］. Hefei： Hefei University of Technology，2016.

［3］LIU J，YIN X F，LI Z T，et al. Facile enzymatic synthesis of diverse naturally‑occurring β‑D‑mannopyranosides catalyzed by glycoside phosphorylases［J］. ACS Catalysis，2021，11（5）：2763‑2768.

［4］LI T L，LI T，ZHANG Y Q，et al. Preparation of tea aroma precursor glycosides：An efficient and sustainable approach via chemical glycosidation［J］. Journal of Agricultural and Food Chemistry，2022，70（7）：2320‑2327.

［5］XIE W C，TAN Z C，GI X H，et al. Thermal decomposition of two synthetic glycosides by TG，DSC and simultaneous Py‐GC‐MS analysis ［J］. Journal of Thermal Analysis and Calorimetry，2007，87（2）：505‐510.

［6］陈敏，董惠忠，沈世豪，等. 中心切割反相/反相二维液相色谱-串联质谱法测定烟叶潜香类糖苷［J］. 质谱学报，2021，42（6）：1175‐1182.

CHEN M，DONG H Z，SHEN S H，et al.Determination of three glycosides in tobacco using heart‐cutting Rp/Rp two dimensional liquid chromatography‐tandem mass spectrometry［J］. Journal of Chinese Mass Spectrometry Society，2021，42（6）：1175‐1182.

［7］DING L，WANG X Y，WANG S，et al. Systematic screening and characterization of glycosides in tobacco leaves by liquid chromatography with atmospheric pressure chemical ionization tandem mass spectrometry using neutral loss scan and product ion scan［J］. Journal of Separation Science，2015，38（23）：4029‑4035.

［8］HECKMAN R A，DULE M F，RIVER L D.The role of tobacco leaf precursors in cigarette flavor［J］. Recent Advance of Tobacco Science，1981（7）：107‐153.

［9］任洪涛，周斌. 咖啡豆在烘焙过程中挥发性物质的组成变化及抗氧化活性评价［J］.云南农业大学学报（自然科学），2018，33（6）：1146‑1153.

REN H T，ZHOU B. The compositions change and antioxidant activity of volatile components coffee beans（Coffea Arabica L. ） during the roasting process［J］.Journal of Yunnan Agricultural University（Natural Science），2018，33（6）：1146‑1153.

［10］肖小武，林凯鹏，周志强，等. GC法同时测定鲜竹沥中10种成分［J］. 中成药，2022，44（5）：1506‑1509.

XIAO X W，LIN K P，ZHOU Z Q，et al. Simultaneous determination of ten constituents in Succus Bambusae by GC［J］. Chinese Traditional Patent Medicine，2022，44（5）：1506‑1509.

［11］耿平兰，黄卫红，程化鹏. 白酒中酚类物质及检测方法的研究进展［J］. 酿酒科技，2020（8）：83‑88.

GENG P L，HUANG W H，CHENG H P. Research progress of phenols in Baijiu and their detection methods［J］. Liquor‐Making Science & Technology，2020（8）：83‑88.

［12］黄春霞，周新军. 愈创木酚应用研发进展［J］. 安徽化工，2022，48（6）：16‑21.

HUANG C X，ZHOU X J. Application and research development progress of guaiacol［J］. Anhui Chemical Industry，2022，48（6）：16‑21.

［13］VIJAYAKUMAR G R，DIVAKAR S. Synthesis of guaiacol‑α‑D‑glucoside and curcumin‑bis‑α‑D‑glucoside by an amyloglucosidase from Rhizopus［J］.Biotechnology Letters，2005，27（18）：1411‑1415.

［14］曾世通，刘珊，孙世豪，等. β-紫罗兰醇葡糖苷热裂解产物及其在卷烟主流烟气中的释放行为［J］. 烟草科

技，2013（8）：33‐36.

ZENG S T，LIU S，SUN S H，et al. Pyrolytic products of β‐ionol‐glucoside and their release behavior in mainstream cigarette smoke［J］. Tobacco Science & Technology，2013（8）：33‐36.

［15］张改红，石栋栋，许航，等. 香芹酚-β-D-葡萄糖苷的合成及在卷烟中的应用［J］.烟草科技，2024，57（3）：20‑27.

ZHANG G H，SHI D D，XU H，et al. Synthesis of carvacrol‐β‐D‐glucoside and its use in cigarette flavoring［J］.Tobacco Science & Technology，2024，57 （3）：20‑27.

［16］黎鸿艺.新型糖苷类潜香化合物的合成研究［D］. 上海：上海应用技术大学，2019.

LI H Y. Study on the synthesis of novel glycoside latent aroma compounds［D］. Shanghai：Shanghai Institute of Technology，2019.

［17］张改红，徐月莹，石栋栋，等. 异丁香酚-β-D-葡萄糖苷的合成及热裂解转移率［J］. 精细化工，2024，41（2）：420‐426.

ZHANG G H，XU Y Y，SHI D D，et al. Synthesis and pyrolysis transfer rate of isoeugenol‐β‐D‐glucopyranoside［J］.Fine Chemicals，2024，41（2）：420‐426.

［18］梁德民，张玮，王嘉乐，等. 丁香酚-β-D-葡萄糖苷的合成、热裂解及其在卷烟中的应用［J］. 烟草科技，

2023，56（2）：74‐79.

LIANG D M，ZHANG W，WANG J L，et al. Synthesis and pyrolysis of eugenol‐β‐D‐glucoside and its application to cigarette flavoring［J］. Tobacco Science & Technology，2023，56（2）：74‐79.

［19］许克静，杨泽恩，杨金初，等. 滤棒载香型卷烟中柠檬烯的烟气转移行为及贮存稳定性研究［J］. 河南农业科学，2024，53（1）：162‐171.

XU K J，YANG Z E，YANG J C，et al. Study on smoke transfer behavior and storage stability of limonene in filter rod flavored cigarettes［J］. Journal of Henan Agricultural Sciences，2024，53（1）：162‐171.

［20］张改红，石栋栋，庞登红，等.愈创木酚-β-D-葡萄糖苷的合成及其加香应用［J］.精细化工，2022，39（10）：2099‐2103.

ZHANG G H，SHI D D，PANG D H，et al. Synthesis of guaiacol‐β‐D‐glucopyranoside and its flavoring application［J］. Fine Chemicals，2022，39（10）：2099‐2103.

［21］毛文龙，朱梦薇，饶先立，等. 加热卷烟中酯类香料单体的转移行为［J］.中国烟草学报，2022，28（6）：11‑19.

MAO W L，ZHU M W，RAO X L，et al. Transfer behavior of ester flavor monomers in heated tobacco products［J］. Acta Tabacaria Sinica，2022，28（6）：11‑19.

［22］张磊，陈阳，张雷，等. 三苄糖苷的合成工艺研究［J］. 中国药物化学杂志，2023，33（5）：347‐351.

ZHANG L，CHEN Y，ZHANG L，et al. Improved synthesis of tribenoside ［J］. Chinese Journal of Medicinal Chemistry，2023，33（5）：347‐351.

［23］戴家威，陈翰驰，金晓，等.固定化糖苷酶在糖苷类化合物合成中的应用［J］. 生物工程学报，2021，37（12）：4169‐4186.

DAI J W，CHEN H C，JIN X，et al.Application of immobilized glycosidase in the synthesis of glycoside compounds［J］.Chinese Journal of Biotechnology，2021，37（12）：4169‐4186.

［24］张改红，徐改改，白冰，等. 麦芽酚-β-D-葡萄糖苷的便捷合成及其加香应用［J］.精细化工，2020，37（5）：997‐1001.

ZHANG G H，XU G G，BAI B，et al.Facile preparation of maltol alcohol‐β‐D‐glucopyranoside and its flavoring application［J］. Fine Chemicals，2020，37 （5）：997‐1001.

［25］王让剑，苏德森，吴建衍，等.超高效液相色谱-串联质谱法测定茶树新梢中两种香叶醇糖苷含量［J］.茶叶学报，2020，61（3）：114‐119.

WANG R J，SU D S，WU J Y，et al. UHPLC‐MS/MS determination of geraniol glycosides in tea shoots［J］.Acta Tea Sinica，2020，61（3）：114‐119.

［26］段海波，解万翠，姜黎，等.玫瑰醇-β-D-吡喃葡萄糖苷的卷烟增香及缓释作用［J］.烟草科技，2019，52 （4）：57‐64.

DUAN H B，XIE W C，JIANG L，et al. Application of rhodinol‐β‐D‐glycoside in cigarette flavoring and slow aroma‐releasing［J］. Tobacco Science & Technology，2019，52（4）：57‐64.

［27］韩路，楚文娟，胡少东，等. 两种加香方式下7种葡萄糖苷配基在烟气中的裂解转移规律［J］. 食品与机械，2022，38（2）：16‐20.

HAN L，CHU W J，HU S D，et al. Study on pyrolysis transfer rules of seven aglycones in flue gas under two kinds of flavoring methods［J］. Food & Machinery，2022，38（2）：16‐20.

[1]	LUO Haitao, WANG Shuoying, QI Yating, LI Ruili, CHEN Dong, RAO Chaoqi, ZHANG Junsong, ZOU Enkai. Effect of Different Enzymes on the Quality Improvement Effect of Discarded Tobacco Extract [J]. Journal of Henan Agricultural Sciences, 2025, 54(3): 170-180.
[2]	LI Haolei, HUANG Xianzhang, CUI Jianxin, YU Yi. The Structure and Diversity of Insect Community in Artemisia argyi Fields in Nanyang [J]. Journal of Henan Agricultural Sciences, 2025, 54(2): 99-106.
[3]	ZHANG Bo, WANG Xinhui, KONG Bo, WANG Zhiguo, LI Ruili, LIANG Miao, ZHANG Junsong. Analysis of Separation Products from Alcohol‑Soluble Extract of Burley Tobacco by Different Apertures of Membrane and Cigarette#br# Flavoring Evaluation [J]. Journal of Henan Agricultural Sciences, 2024, 53(8): 165-172.
[4]	XU Kejing, YANG Zeen, YANG Jinchu, CHEN Xiaolong, LIANG Miao, FENG Yingjie, GAO Mingqi, LIU Wenzhao, MA Shengtao, ZHANG Junsong. Study on Smoke Transfer Behavior and Storage Stability of Limonene in Filter Rod Flavored Cigarettes [J]. Journal of Henan Agricultural Sciences, 2024, 53(1): 162-171.
[5]	ZHANG Qiang, WU Limin, LI Pengyan, ZHAO Na, HU Shen’ao, LU Ninghai. Optimization of Fermentation Conditions and Stability Evaluation of Antagonistic Bacteria against Wheat Crown Rot [J]. Journal of Henan Agricultural Sciences, 2023, 52(5): 121-129.
[6]	XIONG Rui, ZHANG Wei, ZHONG Kangyu, ZHOU Wentao, OU Xi, WANG Hongrui, LONG Pan, XU Ying, FU Zhiqiang. Effects of Straw Returning and Rotating Tillage on Soil Physical Characteristics and Carbon and Nitrogen Content in Double‐Cropping Paddy Field [J]. Journal of Henan Agricultural Sciences, 2023, 52(5): 81-90.
[7]	QIN Maomao, LIU Yanxi, WANG Wenfei, CHANG Yang, ZHOU Zhengfu, LEI Zhensheng, WU Zhengqing. Quality and Its Stability of Wheat Variety Zhengmai 119 with High Quality [J]. Journal of Henan Agricultural Sciences, 2023, 52(2): 21-30.
[8]	ZHANG Suyu, JIN Haiyang, CUI Jingyu, QIN Feng, LI Xiangdong, YUE Junqin, SHAO Yunhui, WANG Hanfang, FANG Baoting, ZHANG Deqi, YANG Cheng. Effect of Different Ecological Environments on Yield and Quality of Strong Gluten Wheat [J]. Journal of Henan Agricultural Sciences, 2022, 51(7): 22-30.
[9]	GAO Qiang, MI Wenhai, XIA Siqi, LIU Mingyue, MAO Wei, JU Jing, ZHAO Haitao. Aggregate Composition,Stability and Nutrient Distribution Characteristics in Yellow Clayey Paddy Soil under Long-Term Different Fertilization Measures [J]. Journal of Henan Agricultural Sciences, 2021, 50(6): 70-81.
[10]	ZHU Jiaoning, LI Yongping, PANG Zhenpeng, TANG Yun. Effect of Mechanical Stirring Intensity on Anaerobic Co-digestion of Cattle Manure and Corn Straw [J]. Journal of Henan Agricultural Sciences, 2021, 50(4): 88-95.
[11]	ZHENG Jianqiang, LIU Bin, WANG Xiaofei, JIA Xuewei, XU Chunping. Preparation and Characterization of Nanocellulose from Tobacco Straw [J]. Journal of Henan Agricultural Sciences, 2021, 50(3): 165-173.
[12]	ZHANG Tiantian, LU Yao, LÜ Wenliang, LIN Xianhua, XU Haiyan, GU Wei. Probiotic Properties Assessment of Lactobacillus plantarum with Salmonella Antagonistic Ability [J]. Journal of Henan Agricultural Sciences, 2021, 50(2): 130-137.
[13]	LIU Yanxi, QIN Maomao, ZHOU Zhengfu, ZHANG Kun, ZHAO Mengqi, WU Zhengqing, LEI Zhensheng. Quality and Its Stability of Strong Gluten Wheat Variety Zhengmai 379 [J]. Journal of Henan Agricultural Sciences, 2019, 48(12): 30-36.