메뉴 건너뛰기




Volumn 58, Issue 19, 2010, Pages 10606-10613

Elucidation of the 1,3-sulfanylalcohol oxidation mechanism: An unusual identification of the disulfide of 3-sulfanylhexanol in sauternes botrytized wines

Author keywords

3,3' disulfanediyldihexan 1 ol; 3 propyl 1,2 oxathiolane; 3 propyl sultine; 3 Sulfanylhexanol; Sauternes wines

Indexed keywords

AIR PURIFICATION; ESSENTIAL OILS; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; ODORS; OXIDATION; SULFUR COMPOUNDS;

EID: 78049277344     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf102022s     Document Type: Article
Times cited : (33)

References (42)
  • 1
    • 11844272619 scopus 로고    scopus 로고
    • Sensorial contribution and formation pathways of thiols in foods: A review
    • Vermeulen, C.; Gijs, L.; Collin, S. Sensorial contribution and formation pathways of thiols in foods: A review. Food Rev. Int. 2005, 21, 69-137.
    • (2005) Food Rev. Int. , vol.21 , pp. 69-137
    • Vermeulen, C.1    Gijs, L.2    Collin, S.3
  • 2
    • 28844455736 scopus 로고    scopus 로고
    • Sulfur-containing odorants in fragrance chemistry
    • Goeke, A. Sulfur-containing odorants in fragrance chemistry. Sulfur Rep. 2002, 23, 243.
    • (2002) Sulfur Rep. , vol.23 , pp. 243
    • Goeke, A.1
  • 3
    • 59849116912 scopus 로고    scopus 로고
    • The role of cysteine and cysteine-S conjugates as odour precursors in the flavour and fragrance industry
    • Starkenmann, C.; Troccaz, M.; Howell, K. The role of cysteine and cysteine-S conjugates as odour precursors in the flavour and fragrance industry. Flavour Frag. J. 2008, 23, 369-381.
    • (2008) Flavour Frag. J. , vol.23 , pp. 369-381
    • Starkenmann, C.1    Troccaz, M.2    Howell, K.3
  • 4
    • 0542441666 scopus 로고
    • Identification of new sulfur-containing volatiles in yellow passionfruit (Passiflora edulis f. flavicarpa)
    • Engel, K. H.; Tressl, R. Identification of new sulfur-containing volatiles in yellow passionfruit (Passiflora edulis f. flavicarpa). J. Agric. Food Chem. 1991, 39, 2249-2252.
    • (1991) J. Agric. Food Chem. , vol.39 , pp. 2249-2252
    • Engel, K.H.1    Tressl, R.2
  • 5
    • 0031825535 scopus 로고    scopus 로고
    • Identification of new volatile thiols in the aroma of Vitis vinifera L. var. Sauvignon blanc wines
    • 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 Frag. J. 1998, 13, 159-162.
    • (1998) Flavour Frag. J. , vol.13 , pp. 159-162
    • Tominaga, T.1    Furrer, A.2    Henry, R.3    Dubourdieu, D.4
  • 6
    • 0033836742 scopus 로고    scopus 로고
    • Contribution of volatile thiols to the aromas of white wines made from several Vitis vinifera grape varieties
    • 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, 178-181.
    • (2000) Am. J. Enol. Vitic. , vol.51 , pp. 178-181
    • Tominaga, T.1    Baltenweck-Guyot, R.2    Peyrot Des Gachons, C.3    Dubourdieu, D.4
  • 8
    • 0002339961 scopus 로고    scopus 로고
    • Mise en évidence de composés cléfs dans l'arôme des vins rosés et clairets de Bordeaux
    • Murat, M. L.; Tominaga, T.; Dubourdieu, D. Mise en évidence de composés clé fs dans l'arôme des vins rosé s et clairets de Bordeaux. J. Int. Sci. Vigne Vin 2001, 35, 99-105.
    • (2001) J. Int. Sci. Vigne Vin , vol.35 , pp. 99-105
    • Murat, M.L.1    Tominaga, T.2    Dubourdieu, D.3
  • 9
    • 29544436906 scopus 로고    scopus 로고
    • 3-Mercaptohexanol: An aroma impact compound of Petite Arvine wine
    • 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.
    • (2005) Am. J. Enol. Vitic. , vol.56 , pp. 407-410
    • Fretz, C.B.1    Luisier, J.L.2    Tominaga, T.3    Amado, R.4
  • 10
    • 34249853306 scopus 로고    scopus 로고
    • Odorous impact of volatile thiols on the aroma of young botrytized sweet wines: Identification and quantification of new sulfanyl alcohols
    • 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.
    • (2007) J. Agric. Food Chem. , vol.55 , pp. 1437-1444
    • Sarrazin, E.1    Shinkaruk, S.2    Tominaga, T.3    Bennetau, B.4    Frerot, E.5    Dubourdieu, D.6
  • 11
    • 22944463115 scopus 로고    scopus 로고
    • Botrytized sweet wines (Sauternes and Tokay)
    • Wiley: New York, The Microbiology of Wine and Vinifications
    • Ribéreau-Gayon, P.; Dubourdieu, D.; Donêche, B.; Lonvaud, A. Botrytized sweet wines (Sauternes and Tokay). In Handbook of Enology; Wiley: New York, 1999; Vol.1: The Microbiology of Wine and Vinifications, pp 410-419.
    • (1999) Handbook of Enology , vol.1 , pp. 410-419
    • Ribéreau-Gayon, P.1    Dubourdieu, D.2    Donêche, B.3    Lonvaud, A.4
  • 14
    • 33847001980 scopus 로고    scopus 로고
    • Characterization of keyaroma compounds of botrytized wines, influence of grape botrytization
    • Sarrazin, E.; Dubourdieu, D.; Darriet, P. Characterization of keyaroma compounds of botrytized wines, influence of grape botrytization. Food Chem. 2007, 103, 536-545.
    • (2007) Food Chem. , vol.103 , pp. 536-545
    • Sarrazin, E.1    Dubourdieu, D.2    Darriet, P.3
  • 15
    • 39149130298 scopus 로고    scopus 로고
    • Analysis of the diastereoisomers of the cysteinylated aroma precursor of 3-sulfanylhexanol in Vitis vinifera grape must by gas chromatography coupled with ion trap tandem mass spectrometry
    • Thibon, C.; Shinkaruk, S.; Tominaga, T.; Bennetau, B.; Dubourdieu, D. Analysis of the diastereoisomers of the cysteinylated aroma precursor of 3-sulfanylhexanol in Vitis vinifera grape must by gas chromatography coupled with ion trap tandem mass spectrometry. J. Chromatogr., A 2008, 1183, 150-157.
    • (2008) J. Chromatogr., A , vol.1183 , pp. 150-157
    • Thibon, C.1    Shinkaruk, S.2    Tominaga, T.3    Bennetau, B.4    Dubourdieu, D.5
  • 16
    • 60249094927 scopus 로고    scopus 로고
    • Impact of noble rot on the aroma precursor of 3-sulfanylhexanol content in Vitis vinifera L. cv Sauvignon blanc and Semillon grape juice
    • 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.
    • (2009) Food Chem. , vol.114 , pp. 1359-1364
    • Thibon, C.1    Dubourdieu, D.2    Darriet, P.3    Tominaga, T.4
  • 17
    • 33749665422 scopus 로고    scopus 로고
    • Aroma extraction dilution analysis of Sauternes wines. Key role of polyfunctional thiols
    • Bailly, S.; Jerkovic, V.; Marchand-Brynaert, J.; Collin, S. Aroma extraction dilution analysis of Sauternes wines. Key role of polyfunctional thiols. J. Agric. Food Chem. 2006, 54, 7227-7234.
    • (2006) J. Agric. Food Chem. , vol.54 , pp. 7227-7234
    • Bailly, S.1    Jerkovic, V.2    Marchand-Brynaert, J.3    Collin, S.4
  • 18
    • 42449089022 scopus 로고    scopus 로고
    • 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
    • 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.
    • (2008) J. Agric. Food Chem. , vol.56 , pp. 2477-2484
    • Campo, E.1    Cacho, J.2    Ferreira, V.3
  • 19
    • 0001265618 scopus 로고    scopus 로고
    • Development of a method for analyzing the volatile thiols involved in the characteristic aroma of wines made from Vitis vinifera L. cv. Sauvignon blanc
    • 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.
    • (1998) J. Agric. Food Chem. , vol.46 , pp. 1044-1048
    • Tominaga, T.1    Murat, M.L.2    Dubourdieu, D.3
  • 20
    • 0347694644 scopus 로고    scopus 로고
    • Simple strategy for the optimization of solid-phase extraction procedures through the use of solid-liquid distribution coefficients application to the determination of aliphatic lactones in wine
    • Ferreira, V.; Jarauta, I.; Ortega, L.; Cacho, J. Simple strategy for the optimization of solid-phase extraction procedures through the use of solid-liquid distribution coefficients application to the determination of aliphatic lactones in wine. J. Chromatogr., A 2004, 1025, 147-156.
    • (2004) J. Chromatogr., A , vol.1025 , pp. 147-156
    • Ferreira, V.1    Jarauta, I.2    Ortega, L.3    Cacho, J.4
  • 21
    • 0001661957 scopus 로고
    • Determination of methoxypyrazines in red wines by stable isotope dilution gas chromatography mass spectrometry
    • Allen, M. S.; Lacey, M. J.; Boyd, S. Determination of methoxypyrazines in red wines by stable isotope dilution gas chromatography mass spectrometry. J. Agric. Food Chem. 1994, 42, 1734-1738.
    • (1994) J. Agric. Food Chem. , vol.42 , pp. 1734-1738
    • Allen, M.S.1    Lacey, M.J.2    Boyd, S.3
  • 22
    • 0037157060 scopus 로고    scopus 로고
    • Impact odorants contributing to the fungus type aroma from grape berries contaminated by powdery mildew (Uncinula necator); incidence of enzymatic activities of the yeast Saccharomyces cerevisiae
    • Darriet, P.; Pons, M.; Henry, R.; Dumont, O.; Findeling, V.; Cartolaro, P.; Calonnec, A.; Dubourdieu, D. Impact odorants contributing to the fungus type aroma from grape berries contaminated by powdery mildew (Uncinula necator); incidence of enzymatic activities of the yeast Saccharomyces cerevisiae. J. Agric. Food Chem. 2002, 50, 3277-3282.
    • (2002) J. Agric. Food Chem. , vol.50 , pp. 3277-3282
    • Darriet, P.1    Pons, M.2    Henry, R.3    Dumont, O.4    Findeling, V.5    Cartolaro, P.6    Calonnec, A.7    Dubourdieu, D.8
  • 23
    • 47849100065 scopus 로고    scopus 로고
    • Identification of volatile compounds responsible for prune aroma in prematurely aged red wines
    • Pons, A.; Lavigne, V.; Eric, F.; Darriet, P.; Dubourdieu, D. Identification of volatile compounds responsible for prune aroma in prematurely aged red wines. J. Agric. Food Chem. 2008, 56, 5285-5290.
    • (2008) J. Agric. Food Chem. , vol.56 , pp. 5285-5290
    • Pons, A.1    Lavigne, V.2    Eric, F.3    Darriet, P.4    Dubourdieu, D.5
  • 24
  • 25
    • 0036114903 scopus 로고    scopus 로고
    • Identification of green note compounds in malt whisky using multidimensional gas chromatography
    • Wanikawa, A.; Hosoi, K.; Kato, T.; Nakagawa, K. Identification of green note compounds in malt whisky using multidimensional gas chromatography. Flavour Frag. J. 2002, 17, 207-211.
    • (2002) Flavour Frag. J. , vol.17 , pp. 207-211
    • Wanikawa, A.1    Hosoi, K.2    Kato, T.3    Nakagawa, K.4
  • 26
    • 66149141897 scopus 로고    scopus 로고
    • Examples of perceptive interactions involved in specific "red-" and "black-berry" aromas in red wines
    • Pineau, B.; Barbe, J. C.; Van Leeuwen,C.;Dubourdieu,D. Examples of perceptive interactions involved in specific "red-" and "black-berry" aromas in red wines. J. Agric. Food Chem. 2009, 57, 3702-3708.
    • (2009) J. Agric. Food Chem. , vol.57 , pp. 3702-3708
    • Pineau, B.1    Barbe, J.C.2    Van Leeuwen, C.3    Dubourdieu, D.4
  • 29
    • 31044444585 scopus 로고    scopus 로고
    • Formation of cyclic sulfinates and sulfinamides through homolytic substitution at the sulfur atom
    • Coulomb, J.; Certal, V.; Fensterbank, L.; Lacôte, E.; Malacria, M. Formation of cyclic sulfinates and sulfinamides through homolytic substitution at the sulfur atom.Angew.Chem., Int. Ed. 2006, 45, 633-637.
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 633-637
    • Coulomb, J.1    Certal, V.2    Fensterbank, L.3    Lacôte, E.4    Malacria, M.5
  • 30
    • 0001323046 scopus 로고    scopus 로고
    • Vacuum headspace method in aroma research: Flavor chemistry of yellow passion fruits
    • Werkhoff, P.; Guntert, M.; Krammer, G.; Sommer, H.; Kaulen, J. Vacuum headspace method in aroma research: Flavor chemistry of yellow passion fruits. J. Agric. Food Chem. 1998, 46, 1076-1093.
    • (1998) J. Agric. Food Chem. , vol.46 , pp. 1076-1093
    • Werkhoff, P.1    Guntert, M.2    Krammer, G.3    Sommer, H.4    Kaulen, J.5
  • 31
    • 0344865651 scopus 로고    scopus 로고
    • Semipreparative reversed-phase liquid chromatographic fractionation of aroma extracts from wine and other alcoholic beverages
    • Ferreira, V.; Hernandez-Orte, P.; Escudero, A.; Lopez, R.; Cacho, J. Semipreparative reversed-phase liquid chromatographic fractionation of aroma extracts from wine and other alcoholic beverages. J. Chromatogr., A 1999, 864, 77-88.
    • (1999) J. Chromatogr., A , vol.864 , pp. 77-88
    • Ferreira, V.1    Hernandez-Orte, P.2    Escudero, A.3    Lopez, R.4    Cacho, J.5
  • 32
    • 0032568066 scopus 로고    scopus 로고
    • Oxidation of 3-sulfanyl-alcohols with sodium metaperiodate: New synthesis of sultines
    • Yolka, S.; Fellous, R.; Lizzani-Cuvelier, L.; Loiseau, M. Oxidation of 3-sulfanyl-alcohols with sodium metaperiodate: New synthesis of sultines. Tetrahedron Lett. 1998, 39, 991-992.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 991-992
    • Yolka, S.1    Fellous, R.2    Lizzani-Cuvelier, L.3    Loiseau, M.4
  • 33
    • 0000655421 scopus 로고
    • A cyclic sulfinate ester. Preparation and reactions of 1,2-benzoxathian-2-oxide
    • Givens, E. N.; Hamilton, L. A. A cyclic sulfinate ester. Preparation and reactions of 1,2-benzoxathian-2-oxide. J. Org. Chem. 1967, 32, 2857-2861.
    • (1967) J. Org. Chem. , vol.32 , pp. 2857-2861
    • Givens, E.N.1    Hamilton, L.A.2
  • 34
    • 0000945646 scopus 로고
    • Oxidative cleavage and cyclization of disulfide carboxylic-acids and alcohols by aqueous iodine-A facile route to 5-membered ring sultines
    • Doi, J. T.; Luehr, G. W.; Musker, W. K. Oxidative cleavage and cyclization of disulfide carboxylic-acids and alcohols by aqueous iodine-A facile route to 5-membered ring sultines. J. Org. Chem. 1985, 50, 5716-5719.
    • (1985) J. Org. Chem. , vol.50 , pp. 5716-5719
    • Doi, J.T.1    Luehr, G.W.2    Musker, W.K.3
  • 35
    • 0000905283 scopus 로고
    • Sulfide oxidation with N-halosuccinimides
    • Harville, R.; Reed, S. F. Sulfide oxidation with N-halosuccinimides. J. Org. Chem. 1968, 33, 3976-3977.
    • (1968) J. Org. Chem. , vol.33 , pp. 3976-3977
    • Harville, R.1    Reed, S.F.2
  • 37
    • 3142713192 scopus 로고    scopus 로고
    • Reactivity of 3-mercaptohexanol in red wine: Impact of oxygen, phenolic fractions, and sulfur dioxide
    • Blanchard, L.; Darriet, P.; Dubourdieu, D. Reactivity of 3-mercaptohexanol in red wine: Impact of oxygen, phenolic fractions, and sulfur dioxide. Am. J. Enol. Vitic. 2004, 55, 115-120.
    • (2004) Am. J. Enol. Vitic. , vol.55 , pp. 115-120
    • Blanchard, L.1    Darriet, P.2    Dubourdieu, D.3
  • 38
    • 70449125995 scopus 로고    scopus 로고
    • Impact of oxygen dissolved at bottling and transmitted through closures on the composition and sensory properties of a Sauvignon Blanc wine during bottle storage
    • Lopes, P.; Silva, M. A.; Pons, A.; Tominaga, T.; Lavigne, V.; Saucier, C.; 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.
    • (2009) J. Agric. Food Chem. , vol.57 , pp. 10261-10270
    • Lopes, P.1    Silva, M.A.2    Pons, A.3    Tominaga, T.4    Lavigne, V.5    Saucier, C.6    Darriet, P.7    Teissedre, P.L.8    Dubourdieu, D.9
  • 39
    • 74549148857 scopus 로고    scopus 로고
    • Reactivity of volatile thiols with polyphenols in a wine-model medium: Impact of oxygen, iron, and sulfur dioxide
    • Nikolantonaki,M.; Chichuc, I.; Teissedre, 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.
    • (2010) Anal.Chim. Acta , vol.660 , pp. 102-109
    • Nikolantonaki, M.1    Chichuc, I.2    Teissedre, P.L.3    Darriet, P.4
  • 40
    • 78049280177 scopus 로고    scopus 로고
    • La vinification des vins liquoreux de pourriture noble
    • Dubourdieu, D. La vinification des vins liquoreux de pourriture noble. Rev. Fr. Oenol. 1999, 176, 32-35.
    • (1999) Rev. Fr. Oenol. , vol.176 , pp. 32-35
    • Dubourdieu, D.1
  • 41
    • 0000409649 scopus 로고
    • Oxidation of grape juice 2-S-glutathionyl caffeol tartaric acid by Botris cinerea laccase and characterization of a new substance 2,5-di-S-glutathionyl caffeoyl tartatic acid
    • Salgues, M.; Cheynier, V.;Günata, Z.; Wylde, R. Oxidation of grape juice 2-S-glutathionyl caffeol tartaric acid by Botris cinerea laccase and characterization of a new substance 2,5-di-S-glutathionyl caffeoyl tartatic acid. J. Food Sci. 1986, 55, 1191-1194.
    • (1986) J. Food Sci. , vol.55 , pp. 1191-1194
    • Salgues, M.1    Cheynier, V.2    Günata, Z.3    Wylde, R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.