Synthesis of alkyl sulfonic acid aldehydes and alcohols, putative precursors to important wine aroma thiols

Tetrahedron Letters

Volumn 56, Issue 13, 2015, Pages 1728-1731

  Duhamel, Nina ^a   Piano, Federico ^a,b   Davidson, Samuel J ^a   Larcher, Roberto ^c   Fedrizzi, Bruno ^a   Barker, David ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b UNIVERSITY OF MILAN   (Italy)

^c RESEARCH AND INNOVATION CENTRE   (Italy)

Author keywords

3 Mercaptohexan 1 ol; 4 Mercapto 4 methylpentan 2 one; Sulfonic acids; Wine thiols

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; SULFONIC ACID DERIVATIVE; THIOL DERIVATIVE;

AROMA; ARTICLE; FILTRATION; MOLECULAR WEIGHT; OXIDATION; PH; PURIFICATION; SYNTHESIS; WINE;

EID: 84924229917     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2015.02.084     Document Type: Article

References (31)

1. J.S. Marais Afr. J. Enol. Vitic. 4 1983 49
2. C. Munoz-Gonzalez, P.J. Martín-Alvarez, M.V. Moreno Arribas, and M.A. Pozo-Bayon J. Agric. Food Chem. 62 2014 66
3. M. Parker, A.P. Pollnitz, D. Cozzolino, I.L. Francis, and M.J. Herderich J. Agric. Food Chem. 55 2007 5948
4. P. Polášková, J. Herszage, and S.E. Ebeler Chem. Soc. Rev. 37 2008 2478
5. C. Coetzee, and W.J. du Toit Food Res. Int. 45 2012 287
6. T. Tominaga, M.L. Murat, and D. Dubourdieu J. Agric. Food Chem. 1044 1998 46
7. T. Tominaga, Y. Niclass, E. Frérot, and D. Dubourdieu J. Agric. Food Chem. 54 2006 7251
8. G. Winter, T. Van Der Westhuizen, V. Higgins, C. Curtin, and M. Ugliano Aust. J. Grape Wine Res. 17 2011 285
9. J.H. Swiegers, D.L. Capone, K.H. Pardon, G.M. Elsey, M.A. Sefton, I.L. Francis, and I.S. Pretorius Yeast 24 2007 561
10. B. Fedrizzi, K.H. Pardon, M.A. Sefton, G.M. Elsey, and D.W. Jeffery J. Agric. Food Chem. 57 2009 991
11. P.A. Grant-Preece, K.H. Pardon, D.L. Capone, A.G. Cordente, M.A. Sefton, D.W. Jeffery, and G.M. Elsey J. Agric. Food Chem. 58 2010 1383
12. A. Roland, R. Schneider, C.L. Guernevé, A. Razungles, and F. Cavelier Food Chem. 121 2010 847
13. T. Tominaga, C. Peyrot des Gachons, and D. Dubourdieu J. Agric. Food Chem. 46 1998 5215
14. D. Dubourdieu, T. Tominaga, I. Masneuf, C.P. des Gachons, and M.L. Murat Am. J. Enol. Vitic. 57 2006 81
15. H. Kobayashi, H. Takase, K. Kaneko, F. Tanzawa, R. Takata, S. Suzuki, and T. Konno Am. J. Enol. Vitic. 61 2010 176
16. M. Subileau, R. Schneider, J.-M. Salmon, and E. Degryse J. Agric. Food Chem. 56 2008 9230
17. T. Allen, M. Herbst-Johnstone, M. Girault, P. Butler, G. Logan, S. Jouanneau, L. Nicolau, and P.A. Kilmartin J. Agric. Food Chem. 59 2011 10641
18. F.R. Pinu, S. Jouanneau, L. Nicolau, R.C. Gardner, and S.G. Villas-Boas Am. J. Enol. Vitic. 63 2012 407
19. R.L. Barker, D.E.F. Gracey, A.J. Irwin, P. Pipasts, and E. Leiska J. Inst. Brew. 89 1983 411
20. F. Fini, M. Nagabelli, and M.F.A. Adamo Adv. Synth. Catal. 352 2010 3163
21. T.J. Johnson, and R.A. Jones Tetrahedron 34 1978 547
22. J.P. Dufour, M. Leus, A.J. Baxter, and A.R. Hayman J. Am. Soc. Brew. Chem. 57 1999 138
23. M. Hori Nippon Nogeik Kaishi 18 1942 155
24. M. Nyborg, H. Outtrup, and T. Dreyer J. Am. Soc. Brew. Chem. 57 1999 24
25. L. Culleré, J. Cacho, and V. Ferreira Anal. Chim. Acta 524 2004 201
26. A. Rapp, and H. Mandery Experientia 42 1986 873
27. R. Schneider, F. Charrier, A. Razungles, and R. Baumes Anal. Chim. Acta 563 2006 58
28. L.C. de Azevedo, M.M. Reis, L.F. Motta, G.O. da Rocha, L.A. Silva, and J.B. de Andrade J. Agric. Food Chem. 55 2007 8670
29. L. Burroughs Am. J. Enol. Vitic. 26 1975 25
30. G. Hoover, K. Hunten, and C. Sankey J. Phys. Chem. 34 1930 1361
31. G. Gellerstedt, J. Gierer, and E. Pettersson Acta Chem. Scand. B 31 1977 735