环境响应控制潜香分子制备及其释放研究进展
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摘要
潜香体是通过化学键合手段,将香料分子与特定基团链接而形成的香料控释体系,在特定条件下控制化学键断裂而释放香料.潜香体能避免因香料本身的高挥发性而引起的留香时间短等问题,从而满足众多加香产品持久留香的要求;该需求反过来又极大促进了潜香体的研究.大多数加香产品是日常生活中的必需品,故基于环境控制潜香体的香料释放备受关注.本文着重介绍了在温和环境条件下潜香分子制备与释放性能的研究进展,特别是对不同pH响应及光响应的潜香体进行了详细的综述.另外也简单介绍了不常见的氧气响应型潜香体,并对潜香体进一步的设计与研究进行了展望.
Profragrances referred to the controlled release system, in which the fragrance molecules and the specific substrates are linked by the characteristic responsive bonding. Profragrances can release fragrances under mild reaction conditions. The controlled release property of profragrances can prolong the scented perception caused by the high volatility of the fragrance molecules, thereby satisfying the demands of many flavored products, especially in requiring long-lasting odor. Due to most flavored products are used in daily life, the controlled release of fragrances based on environmental conditions is given great attention. This review focuses on the preparation and controlled release of profragrances under mild environmental conditions, especially the profragrances with different pH-response or photoresponse, as well as briefly introduce the unusual oxygen-response profragrances. Furthermore, it gives a new insight into the future direction of the design and research of profragrances.
Profragrances referred to the controlled release system, in which the fragrance molecules and the specific substrates are linked by the characteristic responsive bonding. Profragrances can release fragrances under mild reaction conditions. The controlled release property of profragrances can prolong the scented perception caused by the high volatility of the fragrance molecules, thereby satisfying the demands of many flavored products, especially in requiring long-lasting odor. Due to most flavored products are used in daily life, the controlled release of fragrances based on environmental conditions is given great attention. This review focuses on the preparation and controlled release of profragrances under mild environmental conditions, especially the profragrances with different pH-response or photoresponse, as well as briefly introduce the unusual oxygen-response profragrances. Furthermore, it gives a new insight into the future direction of the design and research of profragrances.
引文
1 Martins IM,Barreiro MF,Coelho M,Rodrigues AE.Chem Eng J,2014,245:191-200
2 Carvalho IT,Estevinho BN,Santos L.Int J Cosmet Sci,2016,38:109-119
3 Rodrigues SN,Martins IM,Fernandes IP,Gomes PB,Mata VG,Barreiro MF,Rodrigues AE.Chem Eng J,2009,149:463-472
4 Pe?a B,Panisello C,ArestéG,Garcia-Valls R,GumíT.Chem Eng J,2012,179:394-403
5 Herrmann A.Angew Chem Int Ed,2007,46:5836-5863
6 Herrmann A.Chimia,2017,71:414-419
7 Maddalena U,Trachsel A,Fankhauser P,Berthier DL,Benczédi D,Wang W,Xi X,Shen Y,Herrmann A.Chem Biodiv,2014,11:1700-1733
8 Fehr C,Galindo J.Helv Chim Acta,2005,88:3128-3136
9 Berthier D,Trachsel A,Fehr C,Ouali L,Herrmann A.Helv Chim Acta,2005,88:3089-3108
10 Paret N,Trachsel A,Berthier DL,Herrmann A.Angew Chem Int Ed,2015,54:2275-2279
11 Griesbeck AG,Hinze O,G?rner H,Huchel U,Kropf C,Sundermeier U,Gerke T.Photochem Photobiol Sci,2012,11:587
12 Trachsel A,Buchs B,Herrmann A.Photochem Photobiol Sci,2016,15:1183-1203
13 Indradas B,Hansen C,Palmer M,Womack GB.Flavour Fragr J,2014,29:313-323
14 Berthier D,Paret N,Trachsel A,Fieber W,Herrmann A.Polymers,2013,5:234-253
15 Berthier DL,Paret N,Trachsel A,Herrmann A.Bioconj Chem,2010,21:2000-2012
16 Buchs B,Fieber W,DrahoňovskyD,Lehn JM,Herrmann A.Chem Biodiv,2012,9:689-701
17 Wang Y,Morinaga H,Sudo A,Endo T.J Polym Sci A,2010,48:3816-3822
18 Godin G,Levrand B,Trachsel A,Lehn JM,Herrmann A.Chem Commun,2010,46:3125-3127
19 Trachsel A,Chapuis C,Herrmann A.Flavour Fragr J,2013,28:280-293
20 Trachsel A,Buchs B,Godin G,Crochet A,Fromm KM,Herrmann A.Eur J Org Chem,2012,2012:2837-2854
21 de Saint Laumer JY,Frérot E,Herrmann A.Helv Chim Acta,2003,86:2871-2899
22 Trachsel A,Govoni A,de Saint Laumer JY,Frérot E,Herrmann A.Chem Biodiv,2008,5:2621-2639
23 Tree-udom T,Wanichwecharungruang SP,Seemork J,Arayachukeat S.Carbohydr Polym,2011,86:1602-1609
24 Herrmann A.Photochem Photobiol Sci,2012,11:446-459
25 Derrer S,Flachsmann F,Plessis C,Stang M.Chimia,2007,61:665-669
26 Jones PB,Pollastri MP,Porter NA.J Org Chem,1996,61:9455-9461
27 Pika J,Konosonoks A,Robinson RM,Singh PND,Gudmundsdóttir AD.J Org Chem,2003,68:1964-1972
28 Konosonoks A,Wright PJ,Tsao ML,Pika J,Novak K,Mandel SM,Krause Bauer JA,Bohne C,Gudmundsdóttir AD.J Org Chem,2005,70:2763-2770
29 Plessis C,Derrer S.Tetrahedron Lett,2001,42:6519-6522
30 Falvey DE,Sundararajan C.Photochem Photobiol Sci,2004,3:831-838
31 Pelliccioli AP,Wirz J.Photochem Photobiol Sci,2002,1:441-458
32 Il'ichev YV,Schw?rer MA,Wirz J.J Am Chem Soc,2004,126:4581-4595
33 Young DD,Deiters A.Org Biomol Chem,2007,5:999-1005
34 Robles JL,Bochet CG.Org Lett,2005,7:3545-3547
35 Charlon M,Trachsel A,Paret N,Frascotti L,Berthier DL,Herrmann A.Polym Chem,2015,6:3224-3235
36 Levrand B,Herrmann A.Photochem Photobiol Sci,2002,1:907-919
37 Levrand B,Herrmann A.Flavour Fragr J,2006,21:400-409
38 Indradas B,Womack GB.Pro-fragrance compounds.(Firmenich&Cie[CH]).US Patent,US 20180016521,2018-01-18
2 Carvalho IT,Estevinho BN,Santos L.Int J Cosmet Sci,2016,38:109-119
3 Rodrigues SN,Martins IM,Fernandes IP,Gomes PB,Mata VG,Barreiro MF,Rodrigues AE.Chem Eng J,2009,149:463-472
4 Pe?a B,Panisello C,ArestéG,Garcia-Valls R,GumíT.Chem Eng J,2012,179:394-403
5 Herrmann A.Angew Chem Int Ed,2007,46:5836-5863
6 Herrmann A.Chimia,2017,71:414-419
7 Maddalena U,Trachsel A,Fankhauser P,Berthier DL,Benczédi D,Wang W,Xi X,Shen Y,Herrmann A.Chem Biodiv,2014,11:1700-1733
8 Fehr C,Galindo J.Helv Chim Acta,2005,88:3128-3136
9 Berthier D,Trachsel A,Fehr C,Ouali L,Herrmann A.Helv Chim Acta,2005,88:3089-3108
10 Paret N,Trachsel A,Berthier DL,Herrmann A.Angew Chem Int Ed,2015,54:2275-2279
11 Griesbeck AG,Hinze O,G?rner H,Huchel U,Kropf C,Sundermeier U,Gerke T.Photochem Photobiol Sci,2012,11:587
12 Trachsel A,Buchs B,Herrmann A.Photochem Photobiol Sci,2016,15:1183-1203
13 Indradas B,Hansen C,Palmer M,Womack GB.Flavour Fragr J,2014,29:313-323
14 Berthier D,Paret N,Trachsel A,Fieber W,Herrmann A.Polymers,2013,5:234-253
15 Berthier DL,Paret N,Trachsel A,Herrmann A.Bioconj Chem,2010,21:2000-2012
16 Buchs B,Fieber W,DrahoňovskyD,Lehn JM,Herrmann A.Chem Biodiv,2012,9:689-701
17 Wang Y,Morinaga H,Sudo A,Endo T.J Polym Sci A,2010,48:3816-3822
18 Godin G,Levrand B,Trachsel A,Lehn JM,Herrmann A.Chem Commun,2010,46:3125-3127
19 Trachsel A,Chapuis C,Herrmann A.Flavour Fragr J,2013,28:280-293
20 Trachsel A,Buchs B,Godin G,Crochet A,Fromm KM,Herrmann A.Eur J Org Chem,2012,2012:2837-2854
21 de Saint Laumer JY,Frérot E,Herrmann A.Helv Chim Acta,2003,86:2871-2899
22 Trachsel A,Govoni A,de Saint Laumer JY,Frérot E,Herrmann A.Chem Biodiv,2008,5:2621-2639
23 Tree-udom T,Wanichwecharungruang SP,Seemork J,Arayachukeat S.Carbohydr Polym,2011,86:1602-1609
24 Herrmann A.Photochem Photobiol Sci,2012,11:446-459
25 Derrer S,Flachsmann F,Plessis C,Stang M.Chimia,2007,61:665-669
26 Jones PB,Pollastri MP,Porter NA.J Org Chem,1996,61:9455-9461
27 Pika J,Konosonoks A,Robinson RM,Singh PND,Gudmundsdóttir AD.J Org Chem,2003,68:1964-1972
28 Konosonoks A,Wright PJ,Tsao ML,Pika J,Novak K,Mandel SM,Krause Bauer JA,Bohne C,Gudmundsdóttir AD.J Org Chem,2005,70:2763-2770
29 Plessis C,Derrer S.Tetrahedron Lett,2001,42:6519-6522
30 Falvey DE,Sundararajan C.Photochem Photobiol Sci,2004,3:831-838
31 Pelliccioli AP,Wirz J.Photochem Photobiol Sci,2002,1:441-458
32 Il'ichev YV,Schw?rer MA,Wirz J.J Am Chem Soc,2004,126:4581-4595
33 Young DD,Deiters A.Org Biomol Chem,2007,5:999-1005
34 Robles JL,Bochet CG.Org Lett,2005,7:3545-3547
35 Charlon M,Trachsel A,Paret N,Frascotti L,Berthier DL,Herrmann A.Polym Chem,2015,6:3224-3235
36 Levrand B,Herrmann A.Photochem Photobiol Sci,2002,1:907-919
37 Levrand B,Herrmann A.Flavour Fragr J,2006,21:400-409
38 Indradas B,Womack GB.Pro-fragrance compounds.(Firmenich&Cie[CH]).US Patent,US 20180016521,2018-01-18