Page 170 - 《精细化工》2023年第3期

·626· 精细化工 FINE CHEMICALS 第 40 卷

2.4 主流烟气粒相转移率的计算 intermediates: An efficient and sustainable approach via chemical
glycosidation[J]. Journal of Agricultural and Food Chemistry, 2022,
通过 GC/MS 分析发现，主流烟气粒相物组分中 70(7): 2320-2327.
除了酱油酮的量有显著变化外，其他成分几乎没有 [2] LIU J, YIN X F, LI Z T, et al. Facile enzymatic synthesis of diverse
naturally-occurring β-D-mannopyranosides catalyzed by intermediate
变化，这说明在燃吸温度下，酱油酮-β-D-葡萄葡糖 phosphorylases[J]. ACS Catalysis, 2021, 11(5): 2763-2768.
[3] ZHANG G H (张改红), XU G G (徐改改), BAI B (白冰), et al.
苷主要发生了糖苷键的断裂，生成了酱油酮。未加 Facile preparation of maltol alcohol-β-D-glucopyranoside and its
酱油酮-β-D-葡萄糖苷时，空白卷烟烟气中并无酱油 flavoring application[J]. Fine Chemicals (精细化工), 2020, 37(5):
997-1001.
酮；当添加酱油酮-β-D-葡萄糖苷时，每支卷烟烟气 [4] DUAN H B (段海波), XIE W C (解万翠), JIANG L (姜黎), et al.
中酱油酮的量为 0.087 mg，而每支卷烟中添加化合 Application of rhodinol-β-D-intermediate in cigarette flavoring and
slow aroma-releasing[J]. Tobacco Science & Technology (烟草科
物Ⅳ的平均质量为 6 mg，换算后相应酱油酮的量为 技), 2019, 52(4): 57-64.
2.80 mg。因此，化合物Ⅳ裂解为酱油酮的转移率为 [5] LI Y G (李有桂), LU M M (卢梦梦), ZHU C F (朱成峰), et al.
Synthesis and pyrolysis of methylcyclopentenolone-β-D-
3.11%，即卷烟燃吸过程中 100 mg 化合物Ⅳ可裂解 glucopyranoside[J]. Tobacco Science & Technology (烟草科技),
2015, 48(6): 45-51.
并向卷烟主流烟气粒相物中释放 3.11 mg 的酱油酮。 [6] WANG W (王为). Synthesis of intermediate flavor precursors and
化合物Ⅳ裂解转移率较低，分析可能的原因是，在 their application in cigarette flavoring[D]. Shanghai: Shanghai
Institute of Technology (上海应用技术大学), 2016.
卷烟燃烧过程中，随着烟气的转移，一部分烟气会 [7] STEINHAUS P, SCHIEBERLE P. Characterization of the key aroma
挥发至空气中成为侧流烟气，导致热解产生的相应 compounds in soy sauce using approaches of molecular sensory
science[J]. Journal of Agricultural and Food Chemistry, 2007,
[4]
单体（酱油酮）转移至主流烟气中的量减少 ；另 55(15): 6262-6269.
[8] KANEKO S, KUMAZAWA K, NISHIMURA O. Studies on the key
外，由于烟丝及滤嘴的过滤截留作用，也会导致转
aroma compounds in raw (unheated) and heated Japanese soy
[4]
移率下降。段海波等 报道了添加玫瑰醇糖苷的卷 sauce[J]. Journal of Agricultural and Food Chemistry, 2013, 61(14):
3396-3402.
烟，燃吸后产生的玫瑰醇向主流烟气粒相中的转移 [9] LI M (李梅), YANG Z X (杨朝霞), CHEN H L (陈华磊), et al.
率为 2.21%。韩路等 [21] 测定了烟丝加香方式下７种 Determination of sweet flavor compounds in wort and beer by
ultra-high performance liquid chromatography-tandem mass
糖苷配基在主流烟气粒相中的转移率，其中，转移 spectrometry[J]. Chinese Journal of Chromatography (色谱), 2016,
率最高的为 5-甲基糠醇（1.99%），最低的为薄荷 34(3): 258-262.
[10] BLANK I, FAY L B. Formation of 4-hydroxy-2,5-dimethyl-3(2H)-
醇（0.47%）。酱油酮-β-D-葡萄糖苷的转移率略高 furanone and 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone
through Maillard reaction based on pentose sugars[J]. Journal of
于玫瑰醇糖苷的转移率，远高于薄荷醇糖苷的转移 Agricultural and Food Chemistry, 1996, 44(2): 531-536.
率，这可能与酱油酮的结构和性质有关。转移率的 [11] National Health and Family Planning Committee. National food
safety standard for the use of food additives: GB/T 2760—2014[S].
测定对于不同的糖苷在实际加香中的用量有一定的 Beijing: China Standard Press (中国标准出版社), 2015.
指导作用。 [12] KITAO S, SHIMAOKA Y, SEKINE H. Preparation of 4-O-(α-D-
glucopyranosyl)-4-hydroxy-3(2H)-furanone as antitumor and
antimutagenic agents: JP06135987A[P]. 1994-05-17.
3 结论 [13] KITAO S, MATSUDO S T, SASAKI T, et al. Enzymatic synthesis
of stable, odorless, and powdered furanone glucosides by sucrose
phosphorylase[J]. Bioscience, Biotechnology, and Biochemistry,
（1）以乙酰溴-α-D-葡萄糖和酱油酮为初始原 2000, 64(1): 134-141.
料，在银盐和相转移催化剂作用下，合成了酱油酮- [14] TIAN S S ( 田思 思 ). Research progress of Koenigs-Knorr
glycosylation[J]. Chemical Engineer (化学工程师), 2021, 35(6):
2,3,4,6-四-O-乙酰基-β-D-葡萄糖苷和酱油酮-β-D-葡 56-60, 45.
[15] LI T, LI T L, ZHUANG H R, et al. O-Glycosyl trichloroacetimidates
萄糖苷，相转移催化法优于 Koenigs-Knorr 法。 as glycosyl donors and platinum(Ⅳ) chloride as a dual catalyst
Koenigs-Knorr 法收率较低，为 18.0%；相转移催化 permitting stereo- and regioselective glycosidations[J]. ACS
Catalysis, 2021, 11(16): 10279-10287.
法反应条件温和，收率中等，为 44.5%。酱油酮- [16] SIM J, KIM S H, HUR J, et al. Indium(Ⅲ) triflate-catalyzed
2,3,4,6-四-O-乙酰基-β-D-葡萄糖苷在甲醇钠/甲醇体 glycosylation through an ambient activation of glycosyl fluoride[J].
Asian Journal of Organic Chemistry, 2019, 8(1): 107-110.
系中脱去乙酰基，得到目标酱油酮-β-D-葡萄糖苷， [17] SINGH Y, DEMCHENKO A V. Koenigs-Knorr glycosylation
收率 88.0%。 reaction catalyzed by trimethylsilyl trifluoromethanesulfonate[J].
Chemistry-A European Journal, 2019, 25(6): 1461-1465.
（2）将酱油酮-β-D-葡萄糖苷加入卷烟中，燃吸 [18] CUI J L (崔继来). Contribution of glycosidically bound volatiles on
the aroma formation of oolong tea and black tea[D]. Chongqing:
后，卷烟烟气中能够释放出特征香气物质酱油酮， Southwest University (西南大学), 2016.
燃吸后产生的酱油酮向主流烟气粒相中的转移率为 [19] YANG H X (杨洪锡), XIE W C (解万翠), WANG W M (王维民),
et al. Synthesis and characterization of β-D-glucopyranosides flavor
3.11%。因此，酱油酮-β-D-葡萄糖苷可以作为一种 precursors[J]. Food Science (食品科学), 2007, 28(11): 179-182.
烟用香料前体。本研究可为卷烟加香应用提供理论 [20] LIANG J (梁娟), WENG W Z (翁伟智), SONG J (宋健). Synthesis
of (2,3-dimethoxy-6-formyl)phenyl-β-D-glucoside[J]. Fine Chemicals
参考。 (精细化工), 2017, 34(5): 596-600.
[21] HAN L (韩路), CHU W J (楚文娟), HU S D (胡少东), et al. Study
参考文献： on pyrolysis transfer rules of seven aglycones in flue gas under two
kinds of flavoring methods[J]. Food & Machinery (食品与机械),
[1] LI T L, LI T, ZHANG Y Q, et al. Preparation of tea aroma precursor 2022, 38(2): 16-20, 26.