李燕敏,许彬,刘玉平

• 1:北京工商大学食品学院

摘要(Abstract)：

异硫氰酸酯不仅是一类重要的含硫含氮香料化合物,还是重要的有机合成中间体。随着分析技术的不断发展,越来越多的异硫氰酸酯类化合物在食品中被鉴定出来;一些已经被评价认为作为食用香料是安全的。由于这类香料化合物具有典型的刺激性气息和辛辣味道,可用来调配食用香精。目前美国食品香料与萃取物制造者协会(FEMA)对外公布的一般认为安全(GRAS)的异硫氰酸酯类香料有19种,我国GB 2760-2014中允许使用的异硫氰酸酯类香料有15种。对这些异硫氰酸酯类香料化合物的天然存在、香气特征、理化性质、形成机理以及合成方法进行了概括。

关键词(KeyWords)： 异硫氰酸酯类香料;天然存在;香气特征;合成方法

Abstract:

Keywords:

基金项目(Foundation): 北京市自然科学基金(预探索项目)(6153021)

作者(Author): 李燕敏,许彬,刘玉平

参考文献(References)：

• [1]郑元昌.烯丙基异硫氰酸酯[J].化工生产与技术,2000,7(3):17.
• [2]胡俊锋,刘静姿.芳基异硫氰酸酯的合成与应用[J].合成材料老化与应用,2015,44(2):109-116.
• [3]GB 2760-2014,食品添加剂使用标准[S].
• [4]刘玉平.食用合成香料[M].北京:中国质检出版社,2012:168-176.
• [5]George A Burdock.Fenaroli's handbook of flavor ingredients 6th ed.[M].Florida:The CRC Press,2010:58-1642.
• [6]杜喜玲,张芳.气质色谱法测定山葵风味物质的研究[J].食品工业,2012,33(7):154-156.
• [7]Nadhem Aissani,Paola Tedeschi,Annalisa Maietti,et al.Nematicidal activity of allylisothiocyanate from horseradish(armoracia rusticana)roots against meloidogyne incognita[J].Journal of Agricultural and Food Chemistry,2013,61(20):4723-4727.
• [8]谢丽琼,马东建,薛淑媛.维药刺山柑果实挥发油和脂肪酸成分的GC-MS研究[J].食品科学,2007,28(5):262-264.
• [9]阮小云,付廷雄,卢金清.华中碎米荠挥发油化学成分GCMS分析[J].南京中医药大学学报,2013,29(4):379-381.
• [10]Suleiman Afsharypuor,Maryam Suleimany.Volatile oil constituents of brassica oleracea var.gongylodes seeds[J].Journal of Essential Oil Research,2002,14(1):18-19.
• [11]Ivica Blazevic,Ani Radonic,Josip Mastelic,et al.Hedge mustard(sisymbrium officinale):chemical diversity of volatiles and their antimicrobial activity[J].Chemistry&Biodiversity,2010,7(8):2023-2034.
• [12]Suleiman Afsharypuor,Samira Sepehrnejad.Analysis of the volatile constituents of the seeds,roots,leaves and whole flowering plant of Lepidium latifolium L[J].Journal of Essential Oil Research,2006,18(1):106-107.
• [13]姜子涛,张清峰,李荣.异硫氰酸酯的产生、化学性质及测定方法[J].中国调味品,2005(4):9-13.
• [14]梁浩,李瑞敏,袁其朋.天然活性异硫氰酸酯类化合物的研究进展[J].北京化工大学学报(自然科学版),2015,42(2):1-12.
• [15]Henri Ulrich.Preparation of alkyl isothiocyanates[P].US:3404171,19681001.
• [16]Erich Schmidt,Robert Schnegg,Franz Zaller,et al.Organic isothiocyanates[P].DE:952084,19561108.
• [17]Harisadhan Ghosh,Ramesh Yella,Jayashree Nath,et al.Desulfurization mediated by hypervalent iodine(III):a novel strategy for the construction of heterocycles[J].European Journal of Organic Chemistry,2008,36:6189-6196.
• [18]De-guang Li,Yan-an Shu,Ping-liang Li,et al.Synthesis and structure-activity relationships of aliphatic isothiocyanate analogs as antibiotic agents[J].Medicinal Chemistry Research,2013,22(7):3119-3125.
• [19]陈国广,张大永,赵欣,等.对称和非对称取代硫脲的合成[J].精细化工,2006,23(6):605-608.
• [20]Peng-fei Liu,Chun-yan Li,Jing-wei Zhang,et al.Facile and versatile synthesis of alkyl and aryl isothiocyanates by using triphosgene and cosolvent[J].Synthetic Communications,2013,43(24):3342-3351.
• [21]Latonglila Jamir,Alimenla B,Anil Kumar,et al.Synthesis and reactivity studies of a new reagent,ethyltriphenylphosphonium tribromide[J].Synthetic Communications,2011,41(1):147-155.
• [22]Catusse R,El R Gharbi.Synthesis of isothiocyanate compounds in the presence of polymer-supported ions[J].Reactive Polymers,Ion Exchangers,Sorbents,1988,8(1):79-84.
• [23]Valette L,Poulain S,Fernandez X,et al.Efficient and solvent-free microwave-accelerated synthesis of isothiocyanates using Lawesson's reagent[J].Journal of Sulfur Chemistry,2005,26(2):155-161.
• [24]Jae Nyoung Kim,Jong Hwan Song,Eung K Ryu.A Convenient synthesis of isothiocyanates from primary nitroalkanes[J].Synthetic Communications,1994,24(8):1101-1105.
• [25]Shinichi Fujiwara,Tsutomu Shin-Ike.Novel selenium catalyzed synthesis of isothiocyanates from isocyanides and elemental sulfur[J].Tetrahedron Letters,1991,32(29):3503-3506.
• [26]Shinichi Fujiwara,Tsutomu Shinike,Kazuhiro Okada,et al.A marvelous catalysis of tellurium in the formation of isothiocyanates from isocyanides and sulfur[J].Tetrahedron Letters,1992,33(46):7021-7024.
• [27]Waldemar Adam,Rainer M Bargon,Sara G Bosio,et al.Direct synthesis of isothiocyanates from isonitriles by molybdenum-catalyzed sulfur transfer with elemental sulfur[J].Journal of Organic Chemistry,2002,67(20):7037-7041.
• [28]Mieko Arisawa,Masanori Ashikawa,Atsushi Suwa,et al.Rhodium-catalyzed synthesis of isothiocyanate from isonitrile and sulfur[J].Tetrahedron Letters,2005,46(10):1727-1729.