Identification of a sotolon pathway in dry white wines

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 12, 2010, Pages 7273-7279

  Pons, Alexandre ^a,b   Lavigne, Valérie ^a,b   Landais, Yannick ^b   Darriet, Philippe ^b   Dubourdieu, Denis ^b  

^a SEGUIN MOREAU France   (France)

^b UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

Ascorbic acid; Oxidation; Pathway; Premature aging; Sauvignon blanc; Sotolon; Wine; Yeast

Indexed keywords

SACCHAROMYCES CEREVISIAE; VITACEAE;

4,5-DIMETHYL-3-HYDROXY-2(5H)-FURANONE; FURAN DERIVATIVE;

ANALYSIS; FERMENTATION; FOOD HANDLING; METABOLISM; MICROBIOLOGY; SACCHAROMYCES CEREVISIAE; WINE;

FERMENTATION; FOOD HANDLING; FURANS; SACCHAROMYCES CEREVISIAE; WINE;

EID: 77953626726     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf100150q     Document Type: Article

References (47)

1. Sulser, H.; Depizzol, J.; Büchi, W. A probable flavoring principle in vegetable-protein hydrolysates J. Food Sci 1967, 32, 611-615
2. Blank, I.; Sen, A.; Grosch, W. Potent odorants of the roasted power and brew of Arabica coffee Z. Lebensm.-Unters. Forsch. 1992, 195, 239-245
3. Kirchoff, E.; Schieberle, P. Determination of key aroma compounds in the crumb of a three-stage sourdough rye bread by stable dilution assays and sensory studies J. Agric. Food Chem. 2001, 49, 4304-4311
4. Tokitomo, Y.; Kobayashi, A.; Yamanishi, T. Studies on the "sugary flavor" of raw cane sugar. III. Key compound of the sugary flavor Proc. Jpn. Acad. 1980, 56B) 457-462
5. Takahashi, K.; Tadenuma, M.; Sato, S. 3-Hydroxy-4,5-dimethyl-2(5 H)-furanone, a burnt flavoring compound from aged sake Agric. Biol. Chem. 1976, 40 (2) 325-330
6. Masuda, M. Identification of sotolon and ethyl 9-hydroxynonanoate in botrytised wine and evaluation of the roles of compounds characteristic of it Agric. Biol. Chem. 1984, 48 (11) 2707-2710
7. Girardon, P.; Sauvaire, Y.; Baccou, J.-C.; Bessière, J.-M. Identification de la 3-hydroxy-4,5-dimethyl-2(5 H)-furanone dans larǒme des graines de fenugrec (Trigonella foenum graecum L.) Lebensm.-Wiss. Technol. 1986, 19, 44-46
8. Martin, B.; Etievant, P.; Le Quéré, J. L.; Schlich, P. More clues about sensory impact of sotolon in some flor sherry wines J. Agric. Food Chem. 1992, 40, 475-478
9. Silva Ferreira, A. C.; Barbe, J. C.; Bertrand, A. 3-Hydroxy-4,5-dimethyl- 2(5 H)-furanone: A key odorant of the typical aroma of oxidative aged port wine J. Agric. Food Chem. 2003, 51, 4356-4363
10. Camara, J. S.; Marques, J. C.; Alves, M. A.; Silva Ferreira, A. C. 4,5-Dimethyl-3-hydroxy-2(5 H)-furanone levels in fortified Madeira wines: Relationship to sugar content J. Agric. Food Chem. 2004, 52, 6765-6769
11. Cutzach, I.; Chatonnet, P.; Dubourdieu, D. Rǒle du sotolon dans larǒme des vins doux naturels, influence des conditions délevage et de vieillissement J. Int. Sci. Vigne Vin 1998, 32 (4) 223-233
12. Escudero, A.; Asensio, E.; Cacho, J.; Ferreira, V. Sensory and chemical changes of young white wines stored under oxygen. An assessment of the role played by aldehydes and some other important odorants Food Chem. 2002, 77 (3) 325-331
13. Lavigne, V.; Pons, A.; Darriet, P.; Dubourdieu, D. Changes in the sotolon content of dry white wines during barrel and bottle aging J. Agric. Food Chem. 2008, 56 (8) 2688-2693
14. Silva Ferreira, A. C.; Hogg, T.; Guedes de Pinho, P. Identification of key odorants related to the typical aroma of oxidation-spoiled white wines J. Agric. Food Chem. 2003, 51, 1377-1381
15. Charpentier, C.; Pham, T. T.; Guichard, E.; Arbault, B. In Production de Sotolon par les Levures Isolées des "Vins Jaunes" du Jura, 5e Symposium DOenologie, Bordeaux, France, 1995; Lavoisier: Bordeaux, France, 1995; pp 179 -182.
16. Pham, T. T.; Guichard, E.; Schlich, P.; Charpentier, C. Optimal conditions for the formation of sotolon from alpha-ketobutyric acid in the French "Vin Jaune" J. Agric. Food Chem. 1995, 43, 2616-2619
17. Kobayashi, A., Sotolon, Identification, Formation, and Effect on Flavor. Flavor Chemistry Trends and Development, ACS Symposium Series, Vol. 388; American Chemical Society: Washington, DC, 1989; pp 49 -59.
18. Cutzach, I.; Chatonnet, P.; Dubourdieu, D. Study of the mechanisms of some volatile compounds during the aging of sweet fortified wines J. Agric. Food Chem. 1999, 47, 2837-2846
19. Dubois, P.; Rigaud, J.; Dekimpe, J. Identification de la diméthyl-4,5-tertrahydrofuranedione-2,3 dans le Vin Jaune du Jura Lebensm.-Wiss. Technol. 1976, 9, 366-368
20. Pisarnitsky, A. K.; Bezzubov, A. A.; Egorov, I. A., Nonenzymatic formation of 4,5-dimethyl-3-hydroxy-2(5 H)-furanone in foodstuffs. Prikl. Biokhim. Microbiol. 1987, 642 -646.
21. Hofmann, T.; Schieberle, P. Evaluation of the key odorants in a thermally treated solution of ribose and cysteine by aroma extract dilution techniques J. Agric. Food Chem. 1995, 43, 2187-2194
22. Hofmann, T.; Schieberle, P. Identification of potent aroma compounds in thermally treated mixtures of glucose/cysteine and rhamnose/cysteine using aroma extract dilution technique J. Agric. Food Chem. 1997, 45, 898-906
23. Hofmann, T.; Schieberle, P., Studies on Intermediates Generating the Flavour Compounds 2-Methyl-3-furanthiol, 2-Acetyl-2-thiazoline and Sotolon by Maillard-Type Reactions. In Flavour Science: Recent Developments; The Royal Society of Chemistry: London, 1996; pp 182 -187.
24. König, T.; Gutsche, B.; Hartl, M.; Hübscher, R.; Schreier, P.; Schwab, W. 3-Hydroxy-4,5-dimethyl-2(5 H)-furanone (sotolon) causing an off-flavor: Elucidation of its formation pathways during storage of citrus soft drinks J. Agric. Food Chem. 1999, 47, 3288-3291
25. Blank, I.; Lin, J.; Furmeaux, R.; Welti, D. H.; Fay, L. B. Formation of sotolone from 4-hydroxy-l -isoleucine and 3-amino-4,5-dimethyl-3,4-dihydro-2(5 H)-furanone J. Agric. Food Chem. 1996, 44, 1851-1856
26. Pons, A.; Lavigne, V.; Landais, Y.; Darriet, P.; Dubourdieu, D. Distribution and organoleptic impact of sotolon enantiomers in dry white wines J. Agric. Food Chem. 2008, 56 (5) 1606-1610 (Pubitemid 351506870)
27. Van Del Dool, H.; Kratz, P. A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography J. Chromatogr. 1963, 11, 463-471
28. Cancalon, P. F. Routine analysis of ascorbic acid in citrus juice using capillary electrophoresis J. AOAC Int. 2001, 84 (3) 987-991
29. Liao, T.; Wu, J. S. B.; Wu, M. C.; Chang, H. M. Epimeric separation of l -ascorbic acid and d -isoascorbic acid by capillary zone electrophoresis J. Agric. Food Chem. 2000, 48, 37-41
30. 2 binding phenomena in musts from botrytized grapes J. Agric. Food Chem. 2002, 50 (22) 6408-6412
31. Ribereau-Gayon, P. Connaissance de la nature des combinaisons de lanhydride sulfureux dans les vins Bull. O.I.V. 1972, 507, 406-413
32. Marullo, P. Génétique Quantitative des Levures de Vinification; Faculté dOenologie, Université Bordeaux 2: Bordeaux, France, 2005.
33. Ribereau-Gayon, P.; Dubourdieu, D.; Lonveau, A.; Maujean, A. Traité dOenologie; Librairie Polytechnique Beranger: Paris, 1998; Vol. 2.
34. Blank, I.; Schieberle, P. Analysis of the seasoning-like flavour substance of a commercial lovage extract (Levisticum officinale Koch.) Flavour Fragrance J. 1993, 8, 191-195
35. Flanzy, C. Oenologie, Fondements Scientifiques et Technologiques; Lavoisier Tec et Doc: Paris, 1998.
36. Bartowsky, E. J.; Henschke, P. A. The "buttery" attribute of wine -diacetyl -desirability, spoilage and beyond Int. J. Food Microbiol. 2004, 96 (3) 235-252
37. Flamini, R.; Dalla Vedova, A. Glyoxal/glycolaldehyde: a redox system involved in malolactic fermentation of wine J. Agric. Food Chem. 2003, 51 (8) 2300-2303
38. Shephard, A. B.; Nichols, S. C.; Braithwaite, A. Moisture induced solid phase degradation of l -ascorbic acid part 2, separation and charaterization of the major degradation products Talanta 1999, 48, 595-606
39. Vernin, G.; Chakib, S.; Rogacheva, S. M.; Obretenov, T. D.; Parkanyl, C. Thermal decomposition of ascorbic acid Carbohydr. Res. 1998, 305, 1-15
40. Blouin, J. Contribution a LEtude des Combinaisons de lAnhydride Sulfureux dans les Moǔts et les Vins; Faculté des Sciences, LUniversité de Bordeaux: Bordeaux, France, 1965.
41. Szöllozi, G.; London, G.; Balàspiri, L.; Somlai, C.; Bartok, M. Enantioselective direct aldol addition of acetone to aliphatic aldehydes Chirality 2003, 15 (Suppl.) S90-S96
42. Raab, T.; Hauck, T.; Knecht, A.; Schmitt, U.; Holzgrabe, U.; Schwab, W. Tautomerism of 4-Hydroxy-2,5-dimethyl-3(2 H)-furanone: Evidence for its enantioselective biosynthesis Chirality 2003, 15 (7) 573-578
43. Van Der Sluis, C.; Rahardjo, Y. S. P.; Smit, B. A.; Kroon, P. J.; Hartmans, S.; Ter Schure, E. G.; Tramper, J.; Wijffels, R. Concomitant extracellular accumulation of alpha-keto acids and higher alcohols by Zygosaccharomyces rouxii J. Bio. Bioeng. 2002, 93 (2) 117-124
44. Masneuf-Pomarède, I.; Mansour, C.; Murat, M.-L.; Tominaga, T.; Dubourdieu, D. Influence of fermentation temperature on volatile thiols concentrations in sauvignon blanc wines Int. J. Food Microbiol. 2006, 108 (3) 385-390
45. Sarrazin, E.; Dubourdieu, D.; Darriet, P. Characterization of key-aroma compounds of botrytized wines, influence of grape botrytization Food Chem. 2007, 103 (2) 536-545
46. Godden, P.; Leigh, F.; 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
47. Sanchez, J.; Aracil, J. M. Gaseous permeability of different obturators Bull. O.I.V. 1998, 71, 279-283