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环境响应型潜香体设计与修饰研究进展

胡静 刘明

胡静,刘明. 环境响应型潜香体设计与修饰研究进展[J]. 应用技术学报,2024,24(1):108-116. doi:  10.3969/j.issn.2096-3424.2024.01.011
引用本文: 胡静,刘明. 环境响应型潜香体设计与修饰研究进展[J]. 应用技术学报,2024,24(1):108-116. doi:  10.3969/j.issn.2096-3424.2024.01.011
HU Jing, LIU Ming. Advances in design and modification of environmentally responsive profragrances[J]. J. Technol, 2024, 24(1): 108-116. doi: 10.3969/j.issn.2096-3424.2024.01.011
Citation: HU Jing, LIU Ming. Advances in design and modification of environmentally responsive profragrances[J]. J. Technol, 2024, 24(1): 108-116. doi: 10.3969/j.issn.2096-3424.2024.01.011

环境响应型潜香体设计与修饰研究进展

doi: 10.3969/j.issn.2096-3424.2024.01.011
基金项目: 国家自然科学基金项目(22078196、22278268和22208218);上海市自然科学基金项目(22ZR1460400);上海应用技术大学引进人才基金项目(YJ2022-16);上海应用技术协同创新基金项目(XTCX2023-07)资助
详细信息
    作者简介:

    胡静:胡 静(1982-),女,教授,博士,主要研究方向为香料香精包覆及应用,潜香体制备及气味调控研究。E-mail:hujing@sit.edu.cn

    通讯作者:

    刘 明(1993-),男,讲师,博士,硕导,主要研究方向为潜香体制备与控释性能研究。E-mail:mingliu@sit.edu.cn

  • 中图分类号: O69

Advances in design and modification of environmentally responsive profragrances

  • 摘要: 潜香体是基于环境响应型共价键而将香料分子与非挥发性基质键连形成的新型香料控释体系,其能够在环境条件下实现香料分子的主动控释,从而延长香料留香时间。该类前体物质使得日益精细化和功能化的高端香料发展趋势成为可能,由此导致基于环境控制的潜香体体系受到广泛关注。综述了基本的反应型潜香体,重点介绍光照控释型、水解控释型以及生物酶控释型潜香体的研究进展;介绍了新型的胶囊潜香体和聚合物潜香体;并对潜香体进一步的开发与应用进行了总结与展望。
  • 图  1  环境响应型潜香体及其香料控释机理[21]

    Figure  1.  Environmentally responsive profragrances and the mechanism of controllable fragrance release[21]

    图  2  基于不同光保护基团的光响应型潜香体

    注:1为丙烯酸酯[22]2为苯甲酸酯[23]3为咕吨酸酯[24]4为2-硝基苄基衍生物[25-26]5为α-酮酯[27]6为烷基苯酮[28]7为蒽醌[29]8为环形缩醛类[30]

    Figure  2.  Photoresponsive profragrances based on different photo-protecting groups

    图  3  基于α-酮酯的光响应型潜香体及其光裂解反应香料控释机理[27]

    Figure  3.  α-oxoacetates-based photoresponsive profragrances and the mechanism of photofragmentation for the controllable fragrance release[27]

    图  4  基于各种不同水解机理的水解型潜香体

    注:9为迈克尔加成型[31]10为缩醛型[32]11为缩醛胺型[33]12为邻键参与型[34]

    Figure  4.  Hydrolytically responsive profragrances based on different hydrolytic mechanism

    图  5  阴阳离子液体混合型潜香体的化学结构[35]

    Figure  5.  Chemical structure of anion and cation liquid-based profragrances[35]

    图  6  基于吡啶盐的潜香体及其水解反应香料控释机理[36]

    Figure  6.  Profragrances on the basis of quaternary pyridinium salts and the mechanism of hydrolysis for the controllable fragrance release[36]

    图  7  基于脂肪酶和光照双重响应构建的潜香体及其控释机理[37]

    Figure  7.  Construction of profragrances based on the double response of lipase and light and the mechanism for controllable fragrance release[37]

    图  8  基于自氧化机理构建的乙烯醚型潜香体及其醛类香料分子的控释[39]

    Figure  8.  Autooxidation-based profragrances for controllable fragment aldehydes release[39]

    图  9  基于聚顺丁烯二酸酐制备的聚合物潜香体[42]

    Figure  9.  Poly (maleic anhydride)-based polymeric profragrances[42]

    图  10  基于壳聚糖制备的聚合物潜香体[43]

    Figure  10.  The fabrication of chitosan-based polymeric profragrances[43]

  • [1] HU Y,ZHANG L,WEN R,et al. Role of lactic acid bacteria in flavor development in traditional Chinese fermented foods:a review[J]. Critical Reviews in Food Science and Nutrition,2022,62(10): 2741-2755. doi:  10.1080/10408398.2020.1858269
    [2] WANG S,CHEN H,SUN B. Recent progress in food flavor analysis using gas chromatography-ion mobility spectrometry (GC-IMS)[J]. Food Chemistry,2020,315: 126158. doi:  10.1016/j.foodchem.2019.126158
    [3] COSTA P,TEIXEIRA M A,LIEVRE Y,et al. Modeling fragrance components release from a simplified matrix used in toiletries and household products[J]. Industrial and Engineering Chemistry Research,2015,54(46): 11720-11731. doi:  10.1021/acs.iecr.5b03852
    [4] COSTA P,VELASCO C V,LOUREIRO J M,et al. Effect of cosmetic matrices on the release and odour profiles of the supercritical CO2 extract of origanum majorana l[J]. International Journal of Cosmetic Science,2016,38(4): 364-374. doi:  10.1111/ics.12297
    [5] AMMAYAPPAN L,PAN N C,CHAKRABORTY S,et al. A study on durability of a fragrance finishing on jute fabric[J]. Journal of Natural Fibers,2019,17(11): 1630-1639.
    [6] MA J, FAN J, XIA Y, et al. Preparation of aromatic β-cyclodextrin nano/microcapsules and corresponding aromatic textiles: a review [J]. Carbohydrate Polymers, 2023: 120661.
    [7] TENTORI F,BRENNA E,CROTTI M,et al. Continuous-flow biocatalytic process for the synthesis of the best stereoisomers of the commercial fragrances leather cyclohexanol (4-isopropylcyclohexanol) and woody acetate (4-(tert-butyl)cyclohexyl acetate)[J]. Catalysts,2020,10(1): 10010102 . doi:  10.3390/catal10010102
    [8] ELIA R,GUO J,BUDIJONO S,et al. Encapsulation of volatile compounds in silk microparticles[J]. Journal of Coatings Technology and Research,2015,12(4): 793-799. doi:  10.1007/s11998-015-9668-1
    [9] VALLS A,CASTILLO A,PORCAR R,et al. Urea-based low-molecular-weight pseudopeptidic organogelators for the encapsulation and slow release of (R)-limonene[J]. Journal of Agricultural and Food Chemistry,2020,68(26): 7051-7061. doi:  10.1021/acs.jafc.0c01184
    [10] MANFREDINI N,ILARE J,INVERNIZZI M,et al. Polymer nanoparticles for the release of fragrances:how the physicochemical properties influence the adsorption on textile and the delivery of limonene[J]. Industrial and Engineering Chemistry Research,2020,59(28): 12766-12773. doi:  10.1021/acs.iecr.0c02075
    [11] ZHANG Y,MA J,XU Q. Polyelectrolyte complex from cationized casein and sodium alginate for fragrance controlled release[J]. Colloids and Surfaces B:Biointerfaces,2019(178): 439-444. doi:  10.1016/j.colsurfb.2019.03.017
    [12] GONÇALVES F,RIBEIRO A,SILVA C,et al. Release of fragrances from cotton functionalized with carbohydrate-binding module proteins[J]. ACS Applied Materials and Interfaces,2019,11(31): 28499-28506. doi:  10.1021/acsami.9b08191
    [13] ZHANG T,LU Z,YANG J,et al. Chitosan‐based nanofragrance with antibacterial function applied to wallpaper[J]. Engineering in Life Sciences,2020,20(11): 541-546. doi:  10.1002/elsc.202000016
    [14] ALI M,MEANEY S P,ABEDIN M J,et al. Graphene oxide-silica hybrid capsules for sustained fragrance release[J]. Journal of Colloid Interface Science,2019(552): 528-539. doi:  10.1016/j.jcis.2019.05.061
    [15] LU Z,WANG J,QU L,et al. Reactive mesoporous silica nanoparticles loaded with limonene for improving physical and mental health of mice at simulated microgravity condition[J]. Bioactive Materials,2020,5(4): 1127-1137. doi:  10.1016/j.bioactmat.2020.07.006
    [16] SLAVOVA T G, RADULOVA G M, KRALCHEVSKY P A, et al. Encapsulation of fragrances and oils by core-shell structures from silica nanoparticles, surfactant and polymer: effect of particle size [J]. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2020, 606(125558): 1-11.
    [17] WU C J,LIU Y F,ZHANG W F,et al. Encapsulation and controlled release of fragrances from MIL-101(Fe)-based recyclable magnetic nanoporous carbon[J]. Colloids Surfaces A:Physicochemical and Engineering Aspects,2022(640): 128453. doi:  10.1016/j.colsurfa.2022.128453
    [18] ZHANG B,HUANG J,LIU K,et al. Biocompatible cyclodextrin-based metal-organic frameworks for long-term sustained release of fragrances[J]. Industrial and Engineering Chemistry Research,2019,58(43): 19767-19777. doi:  10.1021/acs.iecr.9b04214
    [19] LEE H,CHOI C H,ABBASPOURRAD A,et al. Encapsulation and enhanced retention of fragrance in polymer microcapsules[J]. ACS Applied Materials and Interfaces,2016,8(6): 4007-4013. doi:  10.1021/acsami.5b11351
    [20] LIU Y,JIANG J. Preparation of β-ionone microcapsules by gelatin/pectin complex coacervation[J]. Carbohydrate Polymers,2023,312: 120839. doi:  10.1016/j.carbpol.2023.120839
    [21] HERRMANN A. Controlled release of volatiles under mild reaction conditions:from nature to everyday products[J]. Angewandte Chemie International Edition,2007,46(31): 5836-5863. doi:  10.1002/anie.200700264
    [22] DERRER S,FLACHSMANN F,PLESSIS C,et al. Applied photochemistry-light controlled perfume release[J]. Chimia,2007,61(10): 665-669. doi:  10.2533/chimia.2007.665
    [23] KONOSONOKS A,WRIGHT P J,TSAO M L,et al. Photoenolization of 2-(2-methyl benzoyl) benzoic acid,methyl ester:effect of e photoenol lifetime on the photochemistry[J]. The Journal of Organic Chemistry,2005,70(7): 2763-2770. doi:  10.1021/jo048055x
    [24] PLESSIS C,DERRER S. Novel photolactonisation from xanthenoic esters[J]. Tetrahedron Letters,2001,42(37): 6519-6522. doi:  10.1016/S0040-4039(01)01296-5
    [25] IL'ICHEV Y V,SCHWÖRER M A,WIRZ J. Photochemical reaction mechanisms of 2-nitrobenzyl compounds:methyl ethers and caged ATP[J]. Journal of the American Chemical Society,2004,126(14): 4581-4595. doi:  10.1021/ja039071z
    [26] LAGE ROBLES J,BOCHET C G. Photochemical release of aldehydes from α-acetoxy nitroveratryl ethers[J]. Organic Letters,2005,7(16): 3545-3547. doi:  10.1021/ol051280w
    [27] HERRMANN A. Photochemistry of 2-oxoacetates:from mechanistic insights to profragrances and bursting capsules[J]. Chimia,2020,74(1): 39-48.
    [28] LEVRAND B,HERRMANN A. Light induced controlled release of fragrances by Norrish type II photofragmentation of alkyl phrnyl ketones[J]. Photochemical and Photobiological Sciences,2002,1(11): 907-919. doi:  10.1039/b207918f
    [29] LEVRAND B,HERRMANN A. Light-induced controlled release of fragrance aldehydes from 1-alkoxy-9,10-antraquinones for applications in functional perfumery[J]. Flavour and Fragrance Journal,2006,21(3): 400-409. doi:  10.1002/ffj.1728
    [30] TRACHSEL A,BUCHS B,HERRMANN A. Photolabile acetals as profragrances:the effect of structural modifications on the light-induced release of volatile aldehydes on cotton[J]. Photochemial and Photobiological Sciences,2016,15(9): 1183-1203. doi:  10.1039/c6pp00206d
    [31] MADDALENA U,TRACHSEL A,FANKHAUSER P,et al. Thioether profragrances:parameters influencing the performance of precursor-based fragrance delivery in functional perfumery[J]. Chemistry and Biodiversity,2014,11(11): 1700-1733. doi:  10.1002/cbdv.201400023
    [32] BUCHS B,FIEBER W,DRAHOŇOVSKÝ D,et al. Stabilized hemiacetal complexes as precursors for the controlled release of bioactive volatile alcohols[J]. Chemistry and Biodiversity,2012,9(4): 689-701. doi:  10.1002/cbdv.201100383
    [33] TRACHSEL A,BUCHS B,GODIN G,et al. Preparation of imidazolidin-4-ones and their evaluation as hydrolytically cleavable precursors for the slow release of bioactive volatile carbonyl derivatives[J]. European Journal of Organic Chemistry,2012(14): 2837-2854. doi:  10.1002/ejoc.201200081
    [34] TRACHSEL A,GOVONI A,DE SAINT LAUMER J Y,et al. Controlled release of volatile secondary and tertiary alcohols by neighboring group participation:stepwise cyclization and re-opening of 2,2-bis(carbamoyl)dibenzoates at neutral pH[J]. Chemistry and Biodiversity.,2008,5(12): 2621-2639. doi:  10.1002/cbdv.200890217
    [35] BERTON P,SHAMSHINA J L,BICA K,et al. Ionic liquids as fragrance precursors:smart delivery systems for volatile compounds[J]. Industrial and Engineering Chemistry Research,2018,57(47): 16069-16076. doi:  10.1021/acs.iecr.8b02903
    [36] ZHOU X,LIU M,HAN J,et al. Hydrolyzable quaternary pyridinium surfactants:antimicrobial profragrances for controllable perfume release[J]. Industrial and Engineering Chemistry Research,2022,61(12): 4202-4211. doi:  10.1021/acs.iecr.2c00129
    [37] FLACHSMANN F,GAUTSCHI M,BACHMANN J P,et al. Enzyme-triggered and self-cleaving fragrant alcohol precursors[J]. Chemistry and Biodiversity,2008,5(6): 1115-1136. doi:  10.1002/cbdv.200890089
    [38] DUNCAN B,LE N D B,ALEXANDER C,et al. Sensing by smell:nanoparticle-enzyme sensors for rapid and sensitive detection of bacteria with olfactory output[J]. ACS Nano,2017,11(6): 5339-5343. doi:  10.1021/acsnano.7b00822
    [39] INDRADAS B,HANSEN C,PALMER M,et al. Autoxidation as a trigger for the slow release of volatile perfumery chemicals[J]. Flavour and Fragrance Journal,2014,29(5): 313-323. doi:  10.1002/ffj.3207
    [40] PARET N,TRACHSEL A,BERTHIER D L,et al. Controlled release of encapsulated bioactive volatiles by rupture of the capsule wall through the light-induced generation of a gas[J]. Angewandte Chemie International Edition,2015,54(7): 2275-2279. doi:  10.1002/anie.201410778
    [41] PARET N,TRACHSEL A,BERTHIER D L,et al. Developing multi stimuli-responsive core/shell microcapsules to control the release of volatile compounds[J]. Macromolecular Materials and Engineering,2019,304(3): 1-15.
    [42] BERTHIER D L,PARET N,TRACHSEL A,et al. Controlled release of damascone from poly(styrene-co-maleic anhydride)-based bioconjugates in functional perfumery[J]. Polymers,2013,5(1): 234-253. doi:  10.3390/polym5010234
    [43] TREE-UDOM T,WANICHWECHARUNGRUANG S P,SEEMORK J,et al. Fragrant chitosan nanospheres:controlled release systems with physical and chemical barriers[J]. Carbohydrate Polymers,2011,86(4): 1602-1609. doi:  10.1016/j.carbpol.2011.06.074
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  • 收稿日期:  2023-10-31
  • 网络出版日期:  2024-01-26
  • 刊出日期:  2024-03-30

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