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Abstract

In this paper, based on the research references on smoke coolants in recent years, based on its classification and synthesis methods, the paper summarizes the common analysis and detection methods of coolants in cigarettes and their effects on the safety of cigarette smoking, and the future smoke.

Publication Date

9-28-2019

First Page

204

Last Page

210

DOI

10.13652/j.issn.1003-5788.2019.09.039

References

[1] KUIPER N M, GAMMON D, LOOMIS B, et al. Trends in sales of flavored and menthol tobacco products in the united states during 2011-2015[J]. Nicotine & Tobacco Research, 2018, 20(6): 698-796.
[2] BESARATINIA A, TOMMASI S. The lingering question of menthol in cigarettes[J]. Cancer Causes and Control, 2015, 26(2): 165-169.
[3] 陈力. 中国L-薄荷醇市场深度调研报告2018版[R]. 深圳: 深圳市深福源信息咨询有限公司, 2018: 43-70.
[4] 念保义, 林明穗, 黄志华, 等. 合成L-薄荷醇产业化的研究进展[J]. 三明学院学报, 2012, 29(6): 72-77.
[5] 孟彦. 生物法非对映体选择性拆分制备L-薄荷醇[D]. 杭州: 浙江大学, 2010: 2-14.
[6] BRADY D, REDDY S, MBONISWA B, et al. Biocatalytic enantiomeric resolution of L-menthol from an eight isomeric menthol mixture through transesterification[J]. Journal of Molecular Catalysis B Enzymatic, 2012, 75: 1-10.
[7] PAN Jiang, DANG Ngoc-duy, ZHENG Gao-wei, et al. Efficient production of L-menthol in a two-phase system with SDS using an immobilized Bacillus subtilis esterase[J]. Bioresources and Bioprocessing, 2014(1): 12-17.
[8] 李锐, 马洪亮, 吴奇林, 等. 左旋异胡薄荷醇的催化合成[J]. 香料香精化妆品, 2010(2): 1-3.
[9] 谢尚梅, 王三永, 李春荣, 等. 一种不对称合成右旋异胡薄荷醇的方法: 中国, 201510105857[P]. 2015-07-15.
[10] 马洪亮, 吴奇林, 李锐, 等. 凉味剂薄荷甘油醚的合成研究[J]. 食品科学技术学报, 2011, 29(3): 13-15.
[11] 唐功. 印迹脂肪酶催化合成乙酸薄荷酯研究[J]. 粮食与油脂, 2011(4): 22-25.
[12] ZHOU Xiao-yan, BEI Hong-xia, LI Zai-jun, et al. Graphene quantum dot-modified lipase for synthesis of L-menthyl acetate with improv ed activity, stability and thermostability[J]. Synthesis and Catalysis: Open Access, 2016, 1: 1-6.
[13] 张爱华, 肖志红, 刘汝宽, 等. 新型离子液体[Hnmp]+HSO-4对乳酸薄荷酯合成的催化效能[J]. 湖南林业科技, 2011, 38(4): 8-11.
[14] ERMAN M B, SNOW J W.Method for stabilizing menthyl lactate: US, WO/2008/130478A1[P]. 2010-02-02.
[15] 陈芝飞, 芦昶彤, 陈瑨, 等. 戊二酸单薄荷酯的合成和热裂解[J]. 河南科学, 2016, 34(8): 1 245-1 251.
[16] 刘善宇, 李浩亮, 李书芳, 等. 微波辐射法合成单琥珀酸薄荷酯[J]. 烟草科技, 2012(6): 50-53.
[17] 岳海波, 梁娅, 陈义坤, 等. 薄荷基甲酸薄荷酯的合成研究[J]. 日用化学工业, 2014, 44(3): 147-150.
[18] 吴键, 郭春生, 廖付, 等. 单薄荷基甲酸甘油酯的合成及热裂解[J]. 烟草科技, 2013(5): 51-55.
[19] 周军学, 陈清. 一种凉味剂N, 2, 3-三甲基-2-异丙基丁酰胺的合成方法: 中国, 103274959A[P]. 2018-04-24.
[20] LEA R, JULIA M, HARALD H, et al. Analysis of menthol, menthol-like, and other tobacco flavoring compounds in cigarettes and in electrically heated tobacco products[J].Beitrge zur Tabakforschung International, 2018, 28: 93-102.
[21] LEFFINGWELL J C. Cool without menthol & cooler than menthol and cooling compounds as insect repellents[R/OL]. [2018-06-08]. https://leffingwell.com/cooler_than_menthol.htm.
[22] 张文. N-乙基-L-薄荷基甲酰胺的合成技术与工艺[D]. 合肥: 合肥工业大学, 2011: 9-10.
[23] 崔秀明, 邬帅帆. 新型凉味剂的合成及烟草应用研究[J]. 当代化工研究, 2017(2): 20-21.
[24] GUPTE N, SALASKAR A, KULKARNI P.Composition of menthol and menthyl lactate, its preparation and its use as a cooling, flavouring and/or fragrance agent: US, 20150313817[P]. 2017-05-30.
[25] SHIGERU T, KENYA I. Method for producing 3-menthoxy propanol and composition for imparting cooling sensation: US, 2004/0106912 A1[P]. 2014-11-06.
[26] LISKO J G, STANFILL S B, WATSON C H. Quantitation of ten flavor compounds in unburned tobacco products[J]. Analytical Methods, 2014, 6(13): 4 698-4 704.
[27] LI Yong, PANG Tao, GUO Zi-ming, et al. Accelerated solvent extraction for GC-based tobacco fingerprinting and its comparison with simultaneous distillation and extraction[J]. Talanta, 2010, 81(1/2): 650-656.
[28] CHEN Cai, LUO Wen-tai, ISABELLE L M, et al. Thestereoisomers of menthol in selected tobacco products: A brief report[J]. Nicotine & Tobacco Research, 2011, 13(8): 741-745.
[29] YANG Yan-qin, CHU Guo-hai, ZHOU Guo-jun, et al. Rapid determination of the volatile components in tobacco by ultrasound-microwave synergistic extraction coupled to headspace solid-phase microextraction with gas chromatography-mass spectrometry[J]. Journal of Separation Science, 2016, 39(6): 1 173-1 181.
[30] YANG Yan-qin, PAN Yuan-jiang, ZHOU Guo-jun, et al. Multivariate analysis of the volatile components in tobacco based on infrared-assisted extraction coupled to headspace solid-phase microextraction and gas chromatography-mass spectrometry[J]. Journal of Separation Science, 2016, 39(21): 4 192-4 201.
[31] GANN N J, DAMBOLENA J S, MARTINI R, et al. Supercritical carbon dioxide fractionation of peppermint oil with low menthol content： Experimental study and simulation analysis for the recovery of piperitenone[J]. Journal of Supercritical Fluids, 2015, 98: 1-11.
[32] 叶荣飞, 赵瑞峰. 我国烟草香精香料的研究现状[J]. 清远职业技术学院学报, 2011, 4(3): 34-37.
[33] 宫梅, 葛炯, 许建铭, 等. 卷烟及烟气中薄荷醇含量的测定[J]. 烟草科技, 2002(7): 29-31.
[34] 宋瑜冰, 谢建平, 宗永立, 等. 薄荷醇在卷烟中转移行为的控制及检测研究综述[J]. 香料香精化妆品, 2005(3): 25-28.
[35] KIM J H, SEO C S, SHIN H K, et al. Simultaneousdetermination of (-)-menthone and (-)-menthol in menthae herba by gas chromatography and principal component analysis[J]. Natural Product Sciences, 2010, 16(3): 180-184.
[36] MACGREGOR I C, STANFILL S B, GORDON S M, et al. Custommentholation of commercial cigarettes for researchpurposes[J]. Toxicology Reports, 2014, 1: 1 068-1 075.
[37] DING Yu, ZHU Li-jun, LIU Shao-min, et al. Analytical method of free and conjugated neutral aroma components in tobacco by solvent extraction coupled with comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry[J]. Journal of Chromatography A, 2013, 1 280: 122-127.
[38] 曹若明. 食品添加剂的色谱分析方法研究及其应用[D]. 济南: 山东大学, 2009: 12-13.
[39] ASZYK J, WOZNIAK M K, KUBICA P, et al. Comprehensive determination offlavouring additives and nicotine in e-cigarette refill solutions Part I: Liquid chromatography-tandem mass spectrometry analysis[J]. Journal of Chromatography A, 2017, 1 519: 45-54.
[40] KUBICA P, AGATA K W, WASIK A, et al. “Dilute & Shoot” approach for rapid determination of trace amounts of nicotine in zero-level e-liquids by reversed phase liquid chromatography and hydrophilic interactions liquid chromatography coupled with tandem mass spectrometry-electrospray ionization[J]. Journal of Chromatography A, 2013, 1 289: 13-18.
[41] MILLER J H, GARDNER W P, GONZALEZ R R. UHPLC separation with MS analysis for eight carbonyl compounds in mainstream tobacco smoke[J]. Journal of chromatographic science, 2010, 48(1): 12-17.
[42] HSU P C, LAN R, BRASKY T M, et al. Metabolomicprofiles of current cigarette smokers[J]. Molecular Carcinogenesis, 2016, 56(2): 594-606.
[43] ZHONG Yu-jing, GUO Dong, FAN Jun, et al. HPLC Enantioseparation of menthol with non-ultraviolet detectors and effect of chromatographic conditions[J]. Chromatographia, 2018, 81(6): 871-879.
[44] KRYSTYNA S W, MAGDALENA W. Preparative separation of menthol and pulegone from peppermint oil (Mentha piperita L.) by high-performance counter-current chromatography[J]. Phytochemistry Letters, 2014, 10: xcⅳ-xcⅷ.
[45] MIRANDA R J, MARIA T P, ANA N A. Smoking,menthol cigarettes and all-cause, cancer and cardiovascular mortality: Evidence from the national health and nutrition examination survey (NHANES) and a meta-analysis[J]. Plos One, 2013, 8(10): e77941.
[46] WILLIS D N, LIU Bo-yi, HA M A, et al. Menthol attenuates respiratory irritation responses to multiple cigarette smoke irritants[J]. The FASEB Journal, 2011, 25(12): 4 434-4 444.
[47] HECK J D. A review and assessment of menthol employed as a cigarette flavoring ingredient[J]. Food and Chemical Toxicology: An International Journal Published for the British Industrial Biological Research Association, 2010, 48(2): S1-S38.
[48] ROSTRON B. Lung cancer mortality risk for US menthol cigarette smokers[J]. Nicotine & Tobacco Research, 2012, 14(10): 1 140-1 144.
[49] BLOT W J, COHEN SS, ALDRICH M, et al. Lung cancer risk among smokers of menthol cigarettes[J]. Journal of the National Cancer Institute, 2011, 103(10): 810-816.
[50] KEELER C, MAX W, YERGER V, et al. Theassociation of menthol cigarette use with quit attempts, successful cessation, and intention to quit across racial/ethnic groups in the united states[J]. Nicotine & Tobacco Research, 2017, 19(12): 1 450-1 464.
[51] HUNRO H M, TARONE R E, WANG T J, et al. Menthol andnonmenthol cigarette smoking all-cause deaths, cardiovascular disease deaths, and other causes of death among blacks and whites[J]. Circulation, 2016, 133(19): 1 861-1 866.
[52] CHOPYK J, CHATTOPADHYAY S, KULKARNI P, et al. Mentholation affects the cigarette microbiota by selecting for bacteria resistant to harsh environmental conditions and selecting against potential bacterial pathogens[J]. Microbiome, 2017, 5(1): 22-35.
[53] LEFFINGWELL J, ROWSELL D. Wilkinson sword cooling compounds: From the beginning to now[J]. Perfumer & Flavorist, 2014, 39: 34-44.
[54] DIOMEDE L. The soothing effect of menthol, eucalyptol and high-intensity cooling agents[J]. Nutrafoods, 2017, 16: 79-83.
[55] ANDERSON S J. Menthol cigarettes and smoking cessation behaviour: A review of tobacco industry documents[J]. Tobacco Control, 2011, 20(S2): ii49-ii56.
[56] 蔡卫兵. 缓释薄荷香精在滤棒中的应用及释放机理的研究[D]. 上海: 华东理工大学, 2006: 3-5.
[57] 朱亚峰, 胡军, 唐荣成, 等. 卷烟滤嘴加香研究进展[J]. 中国烟草学报, 2011, 17(6): 104-109.
[58] EMOND J A, SONEJI S, BRUNETTE M F, et al. Flavour capsule cigarette use among US adult cigarette smokers[J]. Tobacco Control, 2018, 27(6): 650-655.
[59] DOLKA C, PIADE J J, BELUSHKIN M, et al. Menthol addition to cigarettes using breakable capsules in the filter. impact on the mainstream smoke yields of the health canada list constituents[J]. Chemical Research in Toxicology, 2013, 26(10): 1 430-1 443.
[60] KIM H S, PACK E C, KOO Y J, et al. Quantitative analysis of menthol and identification of other flavoring ingredients in capsule cigarettes marketed in Korea[J]. Regulatory Toxicology and Pharmacology, 2018, 92: 420-428.

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