Analysis, occurrence, and potential sensory significance of five polyfunctional mercaptans in white wines

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 18, 2010, Pages 10184-10194

  Mateo Vivaracho, Laura ^a   Zapata, Julián ^a   Cacho, Juan ^a   Ferreira, Vicente ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

fruitiness; impact compound; origin; polyfunctional mercaptan; Sauvignon blanc; Thiols; variety; white wine; wine

Indexed keywords

FRUITINESS; IMPACT COMPOUND; ORIGIN; POLYFUNCTIONAL MERCAPTAN; SAUVIGNON BLANC; THIOLS; VARIETY; WHITE WINE;

FAST FOURIER TRANSFORMS;

WINE;

THIOL DERIVATIVE;

ARTICLE; CHEMISTRY; COMPARATIVE STUDY; FOOD HANDLING; HUMAN; SENSATION; VALIDATION STUDY; WINE;

FOOD TECHNOLOGY; HUMANS; SENSATION; SULFHYDRYL COMPOUNDS; WINE;

VITACEAE;

EID: 77956637955     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf101095a     Document Type: Article

References (53)

1. Kerscher, R.; Grosch, W. Quantification of 2-methyl-3-furanthiol, 2-furfurylthiol, 3-mercapto-2-pentanone, and 2-mercapto-3-pentanone in heated meat J. Agric. Food Chem. 1998, 46, 1954-1958
2. Elmore, J. S.; Nursten, H. E. The effect of 2-furanmethanethiol upon the flavor of instant coffee Int. J. Food Sci. Technol. 1993, 28, 531-536
3. Buettner, A.; Schieberle, P. Characterization of the most odor-active volatiles in fresh, hand-squeezed juice of grapefruit (Citrus paradisi Macfayden) J. Agric. Food Chem. 1999, 47, 5189-5193
4. Engel, K. H.; Tressl, R. Identification of new sulfur-containing volatiles in yellow passion fruits (Passiflora edulis f. flavicarpa) J. Agric. Food Chem. 1991, 39, 2249-2252
5. Kumazawa, K.; Kubota, K.; Masuda, H. Influence of manufacturing conditions and crop season on the formation of 4-mercapto-4-methyl-2-pentanone in Japanese green tea (sen-cha) J. Agric. Food Chem. 2005, 53, 5390-5396
6. Granvogl, M.; Christlbauer, M.; Schieberle, P. Quantitation of the intense aroma compound 3-mercapto-2-methylpentan-1-ol in raw and processed onions (Allium cepa) of different origins and in other Allium varieties using a stable isotope dilution assay J. Agric. Food Chem. 2004, 52, 2797-2802
7. Darriet, P.; Tominaga, T.; Lavigne, V.; Boidron, J.-N.; Dubourdieu, D. Identification of a powerful aromatic component of Vitis vinifera L. var. Sauvignon wines: 4-mercapto-4-methylpentan-2-one Flavour Fragrance J. 1995, 10, 385-392
8. Bouchilloux, P.; Darriet, P.; Dubordieu, D. Mise au point d'une méthode de dosage de la 4-mercapto-4-methylpentan-2-one dans les vins de Sauvignon J. Int. Sci. Vigne Vin. 1996, 30, 23-29
9. Guth, H. Quantification and sensory studies of character impact odorants of different white wine varieties J. Agric. Food Chem. 1997, 45, 3027-3032
10. Bouchilloux, P.; Darriet, P.; Henry, R. Identification of volatile and powerful odorous thiols in Bordeaux red wine varieties J. Agric. Food Chem. 1998, 46, 3095-3099
11. Tominaga, T.; Darriet, P.; Dubourdieu, D. Identification de l'acétate de 3-mercaptohexanol, composé à forte odeur de buis, intervenant dans l'arôme des vins de Sauvignon [Identification of 3-mercaptohexyl acetate in Sauvignon wine, a powerful aromatic compound exhibiting box-tree odor] Vitis 1996, 35, 207-210
12. Tominaga, T.; des Gachons, C. P.; Dubourdieu, D. A new type of flavor precursors in Vitis vinifera L cv. Sauvignon blanc: S-cysteine conjugates J. Agric. Food Chem. 1998, 46, 5215-5219
13. Tominaga, T.; Furrer, A.; Henry, R.; Dubourdieu, D. Identification of new volatile thiols in the aroma of Vitis vinifera L. var. Sauvignon blanc wines Flavour Fragrance J. 1998, 13, 159-162
14. Lopez, R.; Ortin, N.; Perez-Trujillo, J. P.; Cacho, J.; Ferreira, V. Impact odorants of different young white wines from the Canary Islands J. Agric. Food Chem. 2003, 51, 3419-3425
15. 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
16. Campo, E.; Do, B. V.; Ferreira, V.; Valentin, D. Aroma properties of young Spanish monovarietal white wines: a study using sorting task, list of terms and frequency of citation Aust. J. Grape Wine Res. 2008, 14, 104-115
17. Campo, E.; Ferreira, V.; Escudero, A.; Cacho, J. Prediction of the wine sensory properties related to grape variety from dynamic-headspace gas chromatography-olfactometry data J. Agric. Food Chem. 2005, 53, 5682-5690
18. Parr, W. V.; Green, J. A.; White, K. G. Wine judging, context and New Zealand Sauvignon Blanc Eur. Rev. Appl. Psychol. 2006, 56, 231-238
19. Parr, W. V.; Green, J. A.; White, K. G.; Sherlock, R. R. The distinctive flavour of New Zealand Sauvignon blanc: sensory characterisation by wine professionals Food Qual. Pref. 2007, 18, 849-861
20. Murat, M.-L.; Tominaga, T.; Dubourdieu, D. Mise en évidence de composés clefs dans l'arôme des vins rosés et clairets de Bordeaux [Impact of some components on Bordeaux roses and clairets aroma] J. Int. Sci. Vigne Vin 2001, 35, 99-105
21. Ferreira, V.; Ortin, N.; Escudero, A.; Lopez, R.; Cacho, J. Chemical characterization of the aroma of Grenache rose wines: aroma extract dilution analysis, quantitative determination, and sensory reconstitution studies J. Agric. Food Chem. 2002, 50, 4048-4054
22. Masson, G.; Schneider, R. Key compounds of provence rose wine flavor Am. J. Enol. Vitic. 2009, 60, 116-122
23. Fretz, C. B.; Luisier, J. L.; Tominaga, T.; Amado, R. 3-Mercaptohexanol: an aroma impact compound of Petite Arvine wine Am. J. Enol. Vitic. 2005, 56, 407-410
24. Bailly, S.; Jerkovic, V.; Marchand-Bryaert, J.; Collin, S. Aroma extraction dilution analysis of Sauternes wines. Key role of polyfunctional thiols J. Agric. Food Chem. 2006, 54, 7227-7234
25. Campo, E.; Cacho, J.; Ferreira, V. The chemical characterization of the aroma of dessert and sparkling white wines (Pedro Ximenez, Fino, Sauternes, and Cava) by gas chromatography-olfactometry and chemical quantitative analysis J. Agric. Food Chem. 2008, 56, 2477-2484
26. Sarrazin, E.; Shinkaruk, S.; Tominaga, T.; Bennetau, B.; Frerot, E.; Dubourdieu, D. Odorous impact of volatile thiols on the aroma of young botrytized sweet wines: identification and quantification of new sulfanyl alcohols J. Agric. Food Chem. 2007, 55, 1437-1444
27. Thibon, C.; Dubourdieu, D.; Darriet, P.; Tominaga, T. Impact of noble rot on the aroma precursor of 3-sulfanylhexanol content in Vitis vinifera L. cv Sauvignon blanc and Semillon grape juice Food Chem. 2009, 114, 1359-1364
28. Fedrizzi, B.; Magno, F.; Moser, S.; Nicolini, G.; Versini, G. Concurrent quantification of light and heavy sulphur volatiles in wine by headspace solid-phase microextraction coupled with gas chromatography/mass spectrometry Rapid Commun. Mass Spectrom. 2007, 21, 707-714
29. Fedrizzi, B.; Versini, G.; Lavagnini, I.; Badocco, D.; Nicolini, G.; Magno, F. Hyphenated gas chromatography-mass spectrometry analysis of 3-mercaptohexan-1-ol and 3-mercaptohexyl acetate in wine-comparison with results of other sampling procedures via a robust regression Anal. Chim. Acta 2008, 621, 38-43
30. Fedrizzi, B.; Versini, G.; Lavagnini, I.; Nicolini, G.; Magno, F. Gas chromatography-mass spectrometry determination of 3-mercaptohexan-1-ol and 3-mercaptohexyl acetate in wine. A comparison of headspace solid phase microextraction and solid phase extraction methods Anal. Chim. Acta 2007, 596, 291-297
31. Lund, C. M.; Thompson, M. K.; Benkwitz, F.; Wohler, M. W.; Triggs, C. M.; Gardner, R.; Heymann, H.; Nicolau, L. New Zealand Sauvignon blanc distinct flavor characteristics: sensory, chemical, and consumer aspects Am. J. Enol. Vitic. 2009, 60, 1-12
32. Schneider, R.; Kotseridis, Y.; Ray, J. L.; Augier, C.; Baumes, R. Quantitative determination of sulfur-containing wine odorants at sub parts per billion levels. 2. Development and application of a stable isotope dilution assay J. Agric. Food Chem. 2003, 51, 3243-3248
33. Escudero, A.; Gogorza, B.; Melus, M. A.; Ortin, N.; Cacho, J.; Ferreira, V. Characterization of the aroma of a wine from Maccabeo. Key role played by compounds with low odor activity values J. Agric. Food Chem. 2004, 52, 3516-3524
34. Pet'ka, J.; Ferreira, V.; Gonzalez-Vinas, M. A.; Cacho, J. Sensory and chemical characterization of the aroma of a white wine made with Devin grapes J. Agric. Food Chem. 2006, 54, 909-915
35. Blanchard, L. Recherche sur la contribution de certains thiols volatils à l'arôme des vins rouges étude. Etude de leur Genèse et de leur Stabilité Université de Bordeaux 2: Bordeaux, France, 2000.
36. Blanchard, L.; Tominaga, T.; Dubourdieu, D. Formation of furfurylthiol exhibiting a strong coffee aroma during oak barrel fermentation from furfural released by toasted staves J. Agric. Food Chem. 2001, 49, 4833-4835
37. Tominaga, T.; Blanchard, L.; Darriet, P.; Dubourdieu, D. A powerful aromatic volatile thiol, 2-furanmethanethiol, exhibiting roast coffee aroma in wines made from several Vitis vinifera grape varieties J. Agric. Food Chem. 2000, 48, 1799-1802
38. Tominaga, T.; Guimbertau, G.; Dubourdieu, D. Role of certain volatile thiols in the bouquet of aged Champagne wines J. Agric. Food Chem. 2003, 51, 1016-1020
39. Tominaga, T.; Guimbertau, G.; Dubourdieu, D. Contribution of benzenemethanethiol to smoky aroma of certain Vitis vinifera L. wines J. Agric. Food Chem. 2003, 51, 1373-1376
40. Tominaga, T.; Dubourdieu, D. A novel method for quantification of 2-methyl-3-furanthiol and 2-furanmethanethiol in wines made from Vitis vinifera grape varieties J. Agric. Food Chem. 2006, 54, 29-33
41. Mateo-Vivaracho, L.; Cacho, J.; Ferreira, V. Improved solid-phase extraction procedure for the isolation and in-sorbent pentafluorobenzyl alkylation of polyfunctional mercaptans. Optimized procedure and analytical applications J. Chromatogr., A 2008, 1185, 9-18
42. Loscos, N.; Hernandez-Orte, P.; Cacho, J.; Ferreira, V. Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions J. Agric. Food Chem. 2007, 55, 6674-6684
43. Howell, K. S.; Swiegers, J. H.; Elsey, G. M.; Siebert, T. E.; Bartowsky, E. J.; Fleet, G. H.; Pretorius, I. S.; de Barros Lopes, M. A. Variation in 4-mercapto-4-methyl-pentan-2-one release by Saccharomyces cerevisiae commercial wine strains FEMS Microbiol. Lett. 2004, 240, 125-129
44. Murat, M. L.; Masneuf, I.; Darriet, P.; Lavigne, V.; Tominaga, T.; Dubourdieu, D. Effect of Saccharomyces cerevisiae yeast strains on the liberation of volatile thiols in Sauvignon blanc wine Am. J. Enol. Vitic. 2001, 52, 136-139
45. Swiegers, J. H.; Kievit, R. L.; Siebert, T.; Lattey, K. A.; Bramley, B. R.; Francis, I. L.; King, E. S.; Pretorius, I. S. The influence of yeast on the aroma of Sauvignon blanc wine Food Microbiol. 2009, 26, 204-211
46. Lopez, R.; Lapena, A. C.; Cacho, J.; Ferreira, V. Quantitative determination of wine highly volatile sulfur compounds by using automated headspace solid-phase microextraction and gas chromatography-pulsed flame photometric detection-critical study and optimization of a new procedure J. Chromatogr., A 2007, 1143, 8-15
47. Munch, P.; Schieberle, P. Quantitative studies on the formation of key odorants in thermally treated yeast extracts using stable isotope dilution assays J. Agric. Food Chem. 1998, 46, 4695-4701
48. 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
49. Suarez, R.; Suarez-Lepe, J. A.; Morata, A.; Calderon, F. The production of ethylphenols in wine by yeasts of the genera Brettanomyces and Dekkera: a review Food Chem. 2007, 102, 10-21
50. Tominaga, T.; Masneuf, I.; Dubourdieu, D. Powerful aromatic volatile thiols in wines made from several Vitis vinifera grape varieties and their releasing mechanism. In Nutraceutical Beverages: Chemistry, Nutrition, and Health Effects; 2004; Vol. 871, pp 314-337.
51. Rodriguez-Bencomo, J. J.; Schneider, R.; Lepoutre, J. P.; Rigou, P. Improved method to quantitatively determine powerful odorant volatile thiols in wine by headspace solid-phase microextraction after derivatization J. Chromatogr., A 2009, 1216, 5640-5646
52. Murat, M. L.; Tominaga, T.; Saucier, C.; Glories, Y.; Dubourdieu, D. Effect of anthocyanins on stability of a key odorous compound, 3-mercaptohexan-1-ol, in Bordeaux rose wines Am. J. Enol. Vitic. 2003, 54, 135-138
53. Tominaga, T.; Murat, M. L.; Dubourdieu, D. Development of a method for analyzing the volatile thiols involved in the characteristic aroma of wines made from Vitis vinifera L. cv. Sauvignon blanc J. Agric. Food Chem. 1998, 46, 1044-1048