Evolution of 3-mercaptohexanol, hydrogen sulfide, and methyl mercaptan during bottle storage of Sauvignon blanc wines. Effect of glutathione, copper, oxygen exposure, and closure-derived oxygen

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 6, 2011, Pages 2564-2572

  Ugliano, Maurizio ^a,c   Kwiatkowski, Mariola ^a   Vidal, Stéphane ^b,c   Capone, Dimitra ^a   Siebert, Tracey ^a   Dieval, Jean Baptiste ^c   Aagaard, Olav ^b   Waters, Elizabeth J ^a  

^a AUSTRALIAN WINE RESEARCH INSTITUTE   (Australia)

^b Nomacorc SA   (Belgium)

^c Nomacorc Oxygen Management Research Center   (France)

Author keywords

closures; copper; glutathione; oxygen; Sulfur compounds; wine

Indexed keywords

AMBIENT AIR; CLOSURES; COPPER ADDITIONS; COPPER CONCENTRATION; COPPER SULFATE; EFFECT OF OXYGEN; GLUTATHIONE; GLUTATHIONES; MERCAPTOHEXANOL; METHYL MERCAPTANS; OXYGEN EXPOSURE; WINE COMPOSITION; WINE QUALITY;

CONCENTRATION (PROCESS); COPPER; HYDROGEN; HYDROGEN STORAGE; HYDROGEN SULFIDE; SELF ASSEMBLY; SULFUR; SULFUR DETERMINATION; WINE;

OXYGEN;

3 MERCAPTOHEXANOL; 3-MERCAPTOHEXANOL; COPPER; GLUTATHIONE; HEXANOL; HYDROGEN SULFIDE; METHANETHIOL; OXYGEN; THIOL DERIVATIVE;

ARTICLE; CHEMISTRY; FOOD HANDLING; OXIDATION REDUCTION REACTION; TIME; WINE;

COPPER; FOOD HANDLING; GLUTATHIONE; HEXANOLS; HYDROGEN SULFIDE; OXIDATION-REDUCTION; OXYGEN; SULFHYDRYL COMPOUNDS; TIME FACTORS; WINE;

EID: 79952745081     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf1043585     Document Type: Article

References (41)

1. Godden, P.; Lattey, K.; Francis, L.; Gishen, M.; Cowey, G.; Holdstock, M.; Robinson, E.; Waters, E.; Skouroumounis, G.; Sefton, M.; Capone, D.; Kwiatkowski, M.; Field, J.; Coulter, A.; D'Costa, N.; Bramley, B. Towards offering wine to the consumer in optimal condition - the wine, the closures and other packaging variables: a review of AWRI research examining the changes that occur in wine after bottling Wine Ind. J. 2005, 20, 20-30
2. Ugliano, M.; Kwiatkowski, M. J.; Travis, B; Francis, I. L.; Waters, E. J.; Herderich, M. J.; Pretorius, I. S. Post-bottling management of oxygen to reduce off-flavour formation and optimize wine style Wine Ind. J. 2009, 24, 24-28
3. O'Brien, V.; Francis, L.; Osidacz, P. Packaging choices affect consumer enjoyment of wines Wine Ind. J. 2009, 24, 48-54
4. Lopes, P.; Silva, M. A.; Pons, A.; Tominaga, T.; Lavigne, V.; Saucier, V.; Darriet, P.; Teissedre, P.-L.; Dubourdieu, D. Impact of oxygen dissolved at bottling and transmitted through closures on the composition and sensory properties of a Sauvignon Blanc wine during bottle storage J. Agric. Food Chem. 2009, 57, 10261-10270
5. Cowey, G. Excessive copper fining of wines sealed under screwcaps - identifying and treating reductive winemaking characters Aust. N.Z. Grapegrower Winemaker 2008, 545, 49-56
6. Capone, D.; Sefton, M.; Pretorius, I.; Høj, P. Flavour 'scalping' by wine bottle closures - the 'winemaking' continues post vineyard and winery Aust. N.Z. Wine Ind. J. 2003, 18, 16-20
7. Dimkou, E.; Dieval, J. B.; Vidal, S.; Aagaard, O.; Schüssler, C.; Jung, R. Influence of bottling conditions on the evolution of a Riesling wine. In Proceedings of the Intervitis Interfructa Congress, March 23-28, Stuttgardt, 2010.
8. Skouroumounis, G.; Waters, E. J. Oxygen ingress into bottled wine Prac. Vin. Win. 2008, 29, 6-9
9. Lopes, P.; Saucier, C.; Teissedre, P. L.; Glories., Y. Main routes of oxygen ingress through different closures into wine bottles J. Agric. Food Chem. 2007, 55, 5167-5170 (Pubitemid 47056072)
10. Tominaga, T.; Masneuf, I.; Dubourdieu, D. Powerful aromatic thiols in wines made from several Vitis vinifera grape varieties and their releasing mechanism ACS Symp Ser. 2004, No. 871, 314-337
11. Mateo Vivaracho, L.; Cacho, J.; Ferreira, V. Analysis, occurrence and potential sensory significance of five polyfunctional mercaptans in wine J. Agric. Food Chem. 2010, 58, 10184-10194
12. Quideau, S.; Feldman, K. S.; Appel, H. M. Chemistry of galloyl-derived o -quinones: reactivity toward nucleophiles J. Org. Chem. 1995, 60, 4982-4983
13. Blanchard, L.; Darriet, P.; Dubourdieu, D. Reactivity of 3-mercaptphexanol in red wine: impact of oxygen, phenolic fractions, and sulfur dioxide Am. J. Enol. Vitic. 2004, 55, 115-120 (Pubitemid 38927722)
14. Kilmartin, P. A.; Herbst, M.; Nicolau, L. Aroma stability in Sauvignon Blanc wines. Aust. N.Z. Grapegrower Winemaker 2008, (Annu. Technol. Issue), 66 - 72.
15. 2 levels and aromas in a Sauvignon Blanc Wine J. Agric. Food Chem. 2005, 53, 10006-10011 (Pubitemid 43081210)
16. Darriet, P.; Boucilloux, P.; Poupot, C.; Bugaret, Y.; Clerjeau, M.; Sauris, P.; Medina, B.; Dubourdieu, D. Effects of copper fungicide spraying on volatile thiols of the varietal aroma of Sauvignon blanc, Cabenrnet Sauvignon, and Merlot wines Vitis 2001, 40, 93-99 (Pubitemid 32635700)
17. Roussis, I. G.; Lambropoulos, I.; Tzimas, P. Protection of volatiles in a wine with low sulfur dioxide by caffeic acid or glutathione Am. J. Enol. Vitic. 2007, 58, 274-278 (Pubitemid 47067163)
18. Pardon, K. H.; Graney, S. D.; Capone, D. L.; Swiegers, J. H.; Sefton, M. A.; Elsey, G. M. Synthesis of the individual diastereomers of the cysteine conjugate of 3-mercaptohexanol (3-MH) J. Agric. Food Chem. 2008, 56, 3758-3763 (Pubitemid 351860181)
19. Skouroumounis, G. K.; Kwiatkowski, M. J.; Francis, I. L.; Oakey, H.; Capone, D. L.; Duncan, B.; Sefton, M. A.; Waters, E. J. The impact of closure type and storage conditions on the composition, colour and flavour properties of a Riesling and a wooded Chardonnay wine during five years' storage Aust. J. Grape Wine Res. 2005, 11, 369-384
20. Du Toit, W. J.; Lisjak, K.; Stander, M.; Prevoo, D. Using LC-MSMS to assess glutathione levels in south African white grape juices and wines made with different levels of oxygen J. Agric. Food. Chem. 2007, 55, 2765-2769 (Pubitemid 46668276)
21. Siebert, T. E.; Solomon, M; Pollnitz, A. P.; Jeffery, D. W. Selective determination of volatile sulfur compounds in wine by gas chromatography with sulfur chemiluminescence detection J. Agric. Food Chem. 2010, 58, 9454-9462
22. Cheynier, V. F.; Trousdale, E. K.; Singleton, V. F.; Salgues, M. J.; Wylde, R. Characterization of 2- S -glutathionyl caftaric acid and its hydrolysis in relation to grape wines J. Agric. Food. Chem. 1986, 34, 217-221
23. Danilewicz, J. C.; Seccombe, J. T.; Whelan, J. Mechanism of interaction of polyphenols, oxygen, and sulfur dioxide in model wine and wine Am. J. Enol. Vitic. 2008, 59, 128-136 (Pubitemid 351874266)
24. Tominaga, T.; Baltenweck-Guyot, R.; Des Gachons, C. P.; Dubourdieu, D. Contribution of volatile thiols to the aromas of white wines made from several Vitis vinifera grape varieties Am. J. Enol. Vitic. 2000, 51, 178-181 (Pubitemid 30656749)
25. Dubourdieu, D.; Lavigne, V. The role of glutathione on the aromatic evolution of dry white wine Vinidea.net 2004, 2, 1-9
26. Park, S. K.; Boulton, R.; Noble, A. Formation of hydrogen sulfide and glutathione during fermentation of white grape must Am. J. Enol. Vitic. 2000, 51, 91-97 (Pubitemid 30656739)
27. Pozo Bayon, M. A.; Andújar-Ortiz, I.; Moreno-Arribas, M. V. Scientific evidences beyond the application of inactive dry yeast preparations in winemaking Food Res. Int. 2009, 42, 754-761
28. Jocelyn, P. C. Biochemistry of the SH group; Academic Press: London, U.K., 1972.
29. Smith, R. C.; Reed, V. D.; Hil, W. E. Oxidation of thiols by copper(II) Phosphorus Sulfur Silicon Rel. Elem. 1994, 90, 147-154
30. Danilewicz, J. C. Interaction of sulfur dioxide, polyphenols, and oxygen in a wine-model system: central role of iron and copper Am. J. Enol. Vitic. 2007, 58, 53-60 (Pubitemid 46761184)
31. Nikolantonaki, M.; Chichuc, I.; Teissedere, P.-L.; Darriet, P. Reactivity of volatile thiols with polyphenols in a wine-model medium: impact of oxygen, iron, and sulfur dioxide Anal. Chim. Acta 2010, 660, 102-109
32. Siebert, T.; Bramley, B.; Solomon, M. Hydrogen sulfide: aroma detection threshold study in white and red wines Technol. Rev. 2009, 183, 14-16
33. Mecchi, E. P.; Pippen, E. L.; Lineweaver, H. Origin of hydrogen sulfide in heated chicken muscle J. Food Sci. 1964, 29, 393-399
34. Godden, P.; Francis, L.; Field, J.; Gishen, M.; Coulter, A.; Valente, P.; Hoj, P.; Robinson, E. Wine bottle closures: physical characteristics and effect on composition and sensory properties of a Semillon wine. 1. Performance up to 20 months post-bottling Aust. J. Grape Wine Res. 2001, 7, 64-105
35. Gruenwedel, D.; Patnaik, R. K. Release of hydrogen sulfide and methyl mercaptan from sulfur containing amino acids J. Agric. Food Chem. 1971, 19, 775-779
36. Luh, T.-Y.; Ni, Z.-J. Transition-metal-mediated C-S bond cleavage reactions Synthesis 1990, 89-103
37. Bagiyan, G. A.; Koroleva, I. K.; Soroka, N. V.; Ufimtsev, A. V. Kinetics of the catalytic oxidation reactions of thiol compounds in aqueous solutions in the presence of copper ions Kinet. Catal. 2004, 3, 398-406
38. Solomon, M. R.; Geue, J.; Osidacz, P.; Siebert, T. E. Aroma detection threshold study of methanethiol in white and red wine Technol. Rev. 2010, 186, 7-10
39. Mestres, M.; Busto, O.; Guasch, J. Analysis of organic sulfur compounds in wine aroma J. Chromatogr., A 2000, 881, 569-581 (Pubitemid 30332236)
40. Leppanen, O. A.; Denslow, J.; Ronkainen, P. P. Determination of thioacetates and some other volatile sulfur compounds in alcoholic beverages J. Agric. Food Chem. 1980, 28, 359-362
41. Belancic Majcenovic, A.; Schneider, R.; Lepoutre, J.-P.; Lempeur, V.; Baumes, R. Synthesis and stable isotope dilution assay of ethanethiol and diethyl disulfide in wine using solid phase microextraction. Effect of ageing on their levels in wine J. Agric. Food Chem. 2002, 50, 6653-6658 (Pubitemid 35253152)