Pro-fragrant ionic liquids with stable hemiacetal motifs: Water-triggered release of fragrances

Chemical Communications

Volumn 51, Issue 21, 2015, Pages 4455-4457

  Gunaratne, H Q Nimal ^a   Nockemann, Peter ^a   Seddon, Kenneth R ^a  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; ALCOHOL DERIVATIVE; DIMETHYL SULFOXIDE; FRAGRANCE; INORGANIC SALT; IONIC LIQUID; MAJANTOL; PERFUME; PHENETHYL ALCOHOL; UNCLASSIFIED DRUG; VOLATILE AGENT; WATER;

ARTICLE; CRYSTAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; TEMPERATURE; X RAY CRYSTALLOGRAPHY;

EID: 84924067508     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c5cc00099h     Document Type: Article

References (53)

1. Chemistry and Technology of Flavors and Fragrances, ed., D. J. Rowe, Blackwell, Oxford, 2005
2. The Chemistry of Fragrances, ed., D. Phybus, and, C. Sell, The Royal Society of Chemistry, Cambridge, 1999
3. P. J. Teisseire, Chemistry of Fragrant Substances, VCH, Weinheim, 1994
4. Perfumes: Art, Science and Technology, ed., P. M. Muller, and, D. Lamparsky, Elsevier Applied Science, 1994
5. H. Surburg and J. Panten, Common Fragrance and Flavor Materials, Wiley-VCH, Weinheim, 5th edn, 2006
6. H. Surburg and J. Panten, Common Fragrance and Flavour Materials, Wiley-VCH, Wienheim, 5th edn, 2006
7. Z. Xiao T. Tian J. Hu M. Wang R. Zhou Flavour Fragrance J. 2014 29 22 34
8. C. Yuan Z. Lu Z. Jin Food Chem. 2014 152 140 145
9. A. V. Sadovoy M. V. Lomova M. N. Antipina N. A. Braun G. B. Sukhorukov M. V. Kiryukhin ACS Appl. Mater. Interfaces 2013 5 8948 8954
10. C. P. Chang T. Dobashi Colloids Surf., B 2003 32 257 262
11. S. Leclercq K. Harlander G. A. Reineccius Flavour Fragrance J. 2009 24 17 24
12. P. Lertsutthiwong P. Rojsitthisak U. Nimmannit Mater. Sci. Eng., C 2009 29 856 860
13. F. Stoddart, Cyclodextrins, Royal Society of Chemistry, Cambridge, 1989
14. D. J. Cram and J. M. Cram, in Container Molecules and their Guests, Monographs in Supramolecular chemistry, ed., J. F. Stoddart, 1994
15. U. Numanoʇlu T. Şen N. Tarimci M. Kartal O. M. Y. Koo H. Önyüksel AAPS PharmSciTech 2007 8 E1 E9
16. W. C. E. Schofield J. P. S. Badyal ACS Appl. Mater. Interfaces 2011 3 2051 2056
17. S. D. Rodriguez D. L. Bernik Appl. Spectrosc. 2013 67 884 891
18. C. Yuan Z. Lu Z. Jin Food Chem. 2014 152 140 145
19. J.-Y. Saint Laumer E. Frerot A. Herrmann Helv. Chim. Acta 2003 86 2871
20. A. D. Headley S. D. Starnes L. Y. Wilson G. R. Famini J. Org. Chem. 1994 59 8040 8046
21. S. Espinosa E. Bosch M. Rosus Anal. Chem. 2002 74 3809 3818
22. J. M. Gardlik and M. R. Sivik, WO 98/07405, 1998
23. D. Anderson and G. Frater, EP 0911315, 1999
24. F. Flachsmann M. Gautschi J.-P. Bachmann G. Brunner Chem. Biodiversity 2008 5 1115 1136
25. D. Anderson and G. Frater, Givaudan Roure SA, EP 0936211, 1999
26. S. B. Lyon et al., U. S. Pat., 9111988, 1991
27. P. Kraft Chimia 2001 55 379 387
28. S. Rochat C. Minardi J.-Y. Saint Laumer A. Herrmann Helv. Chim. Acta 2000 83 1645 1671
29. V. N. R. Pillai Synthesis 1980 1 26
30. C. G. Bochet J. Chem. Soc., Perkin Trans. 1 2002 125 142
31. A. P. Pelliccioli J. Wirz Photochem. Photobiol. Sci. 2002 1 441 458
32. V. Lemieux S. Gauthier N. R. Branda Angew. Chem., Int. Ed. 2006 45 6820 6824
33. J. Lage Robles C. G. Bochet Org. Lett. 2005 7 3545 3547
34. Z. Xiao T. Tian J. Hu M. Wang R. Zhou Flavour Fragrance J. 2014 29 22 34
35. W.-C. Hsieha C.-P. Chang Y. L. Gao Colloids Surf., B 2006 53 209 214
36. R. D. Rogers, D. T. Daly, G. Gurau, D. MacFarlane, J. Turanjanin, P. M. Dean, J. L. Scott, K. Bica and K. R. Seddon, WO 2010/078300A1, 2010
37. M. Blesic H. Q. N. Gunaratne P. Nockemann P. McCarron K. R. Seddon RSC Adv. 2013 3 329 333
38. V. Athawale N. Manjrekar M. Athawale Tetrahedron Lett. 2002 43 4797 4800
39. F. Aulenta M. G. B. Drew A. Foster W. Hayes S. Rannard D. W. Thornthwaite T. G. A. Youngs Molecules 2005 10 8 97
40. H. Kamogawa Y. Haramoto T. Nakazawa H. Sugiura M. Nanasawa Bull. Chem. Soc. Jpn. 1981 54 1577 1578
41. R. M. Boden, W. L. Schreiber, F. Tabak and H. G. M. Reijmer, US 6165452, 2000
42. R. Suffis, M. L. Barr, K. Ishida, K. Sawano, T. Sato and A. G. van Loveren, World Pat., WO 94/06441, 1994
43. A. Harriman Angew. Chem., Int. Ed. 2007 46 5836 5863
44. D. M. Clode Chem. Rev. 1979 79 491 513
45. E. Neuzil J. Josselin J. C. Breton J. L. Gaumet B. Lemanceau Bull. Soc. Pharm. Bordeaux 1979 118 82 90
46. P. M. Lukin A. B. Zolotoi S. V. Konovalikhin S. P. Zil'berg A. Kh. Bulai O. A. D'yachenko L. O. Atovmyan O. E. Nasakin Russ. Chem. Bull. 1986 35 1318 1319
47. J. F. Miller A. Spaltenstein Tetrahedron Lett. 1996 37 2521 2524
48. H. Q. N. Gunaratne P. Nockemann K. R. Seddon Green Chem. 2014 16 2411 2417
49. M. Blesic H. Q. N. Gunaratne J. Jacquemin P. Nockemann S. Olejarz K. R. Seddon C. R. Strauss Green Chem. 2014 16 4115 4121
50. M. D. Soutullo R. A. O'Brien K. E. Gaines J. H. Davis Jr. Chem. Commun. 2009 2529 2531
51. K. Laumen M. P. Schneider Chem. Commun. 2009 598 600
52. K. Powell J. Benkhoff W. Fischer K. Fritzsche Eur. Coat. J. 2006 9 40 49
53. S. J. Coles P. A. Gale Chem. Sci. 2012 3 683 689