Stereoisomeric distribution of 3-mercaptohexan-1-ol and 3-mercaptohexyl acetate in dry and sweet white wines made from Vitis vinifera (var. Sauvignon blanc and Semillon)

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 19, 2006, Pages 7251-7255

  Tominaga, Takatoshi ^a   Niclass, Yvan ^b   Frérot, Eric ^b   Dubourdieu, Denis ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

^b Analysis and Perception Department   (Switzerland)

Author keywords

3 mercaptohexan 1 ol; 3 mercaptohexyl acetate; Botrytis cinerea; Enantiomeric distribution

Indexed keywords

3 MERCAPTOHEXAN 1 OL; 3 MERCAPTOHEXYL ACETATE; 3-MERCAPTOHEXAN-1-OL; 3-MERCAPTOHEXYL ACETATE; ACETIC ACID DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; CHEMISTRY; FERMENTATION; FRUIT; GRAPE; HUMAN; ODOR; STEREOISOMERISM; VOLATILIZATION; WINE;

ACETATES; FERMENTATION; FRUIT; HUMANS; SMELL; STEREOISOMERISM; SULFHYDRYL COMPOUNDS; VITIS; VOLATILIZATION; WINE;

BOTRYOTINIA FUCKELIANA; BUXACEAE; CITRUS X PARADISI; PASSIFLORA EDULIS; VITACEAE; VITIS SP.; VITIS VINIFERA;

EID: 33749674486     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf061566v     Document Type: Article

References (18)

1. 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.
2. Weber, B.; Maas, B.; Marx, A.; Olk, J.; Mosandl, A. Stereoisomeric flavour compounds. 72. Stereoisomeric distribution of some chiral sulfur-containing trace components of yellow passion fruits. J. Agric. Food Chem. 1995, 43, 2438-2441.
3. Weber, B.; Dietrich, A.; Maas, B.; Marx, A.; Olk, J.; Mosandl, A. Stereoisomeric flavour compounds. LXVI. Enantiomeric distribution of the chiral sulphur-containing alcohols in yellow and purple passion fruits. Z. Lebensm. Unters. Forsch. 1994, 199, 48-50.
4. Weber, B.; Haag, H.-P.; Mosandl, A. Stereoisomere aromastoffe. LIX. 3-mercaptohexyl-und 3-methylthiohexylalkanoate-Strukture und eigenschaften des enantiomeren. Z. Lebensm. Unters. Forsch. 1992, 195, 426-428.
5. 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. Vitis 1996, 35 (4), 207-210.
6. 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.
7. Tominaga, T.; Baltenweck-Guyot, R.; Peyrot des Gachons, C.; 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 (2), 178-181.
8. Murat, M. L.; Tominaga, T.; Dubourdieu, D. Mise en évidence du rôle des thiols volatils dans l'arôme fruité des vins rosés et clairets de Bordeaux. J. Int. Sci. Vigne Vin. 2001, 35 (2), 99-105.
9. Bouchilloux, P.; Darriet, P.; Henry, R.; Lavigne, V.; Dubourdieu, D. Identification of volatile and powerful odorous thiols in Bordeaux red wine varieties. J. Agric. Food Chem. 1998, 46, 3095-3099.
10. López, 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.
11. Fretz, C.; Luisier, J.-L.; Tominaga, T.; Amadò, R. 3-Mercaptohexanol: an aroma impact compound of Petite Arvine Wine. Am. J. Enol. Vitic. 2005, 4, 407-410.
12. 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, 46, 1799-1802.
13. 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.
14. Van de Waal, M.; Niclass, Y.; Snowden, R.; Bernardinelli, G.; Escher, S. Helv. Chim. Acta 2002, 85, 1246-1260.
15. Boidron, J. N.; Chatonnet, P.; Pons, M. Influence du bois sur certaines sur certaines substances odorantes des vins. Conn. Vigne Vin. 1988, 22, 275-294.
16. 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.
17. Tominaga, T.; Peyrot des Gachons, C.; 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.
18. Wakabayashi, H.; Wakabayashi, M.; Eisenreich, W.; Engel, K.-H. Stereochemical course of the generation of 3-mercaptohexanal and 3-mercaptohexanol by β-lyase-catalysed cleavage of cysteine conjugate. J. Agric. Food Chem. 2004, 52, 110-116.