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Volumn 64, Issue 20, 2016, Pages 4105-4113

Reaction Mechanisms of Metals with Hydrogen Sulfide and Thiols in Model Wine. Part 2: Iron- and Copper-Catalyzed Oxidation

Author keywords

copper; H2S; iron; oxidation; reaction mechanism; thiols; wine aroma

Indexed keywords

ACETALDEHYDE; AMINO ACIDS; BREWERIES; COPPER; COPPER COMPOUNDS; IRON; ODORS; OXIDATION; REDOX REACTIONS; WINE;

EID: 84973162733     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/acs.jafc.6b00642     Document Type: Article
Times cited : (49)

References (35)
  • 1
    • 0038044732 scopus 로고    scopus 로고
    • Review of reaction mechanisms of oxygen and proposed intermediate reduction products in wine: Central role of iron and copper
    • Danilewicz, J. C. Review of reaction mechanisms of oxygen and proposed intermediate reduction products in wine: Central role of iron and copper Am. J. Enol. Vitic. 2003, 54, 73-85
    • (2003) Am. J. Enol. Vitic. , vol.54 , pp. 73-85
    • Danilewicz, J.C.1
  • 2
    • 34248563026 scopus 로고    scopus 로고
    • Interaction of sulfur dioxide, polyphenols, and oxygen in a wine-model system: Central role of iron and copper
    • 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
    • (2007) Am. J. Enol. Vitic. , vol.58 , pp. 53-60
    • Danilewicz, J.C.1
  • 3
    • 0025095542 scopus 로고
    • Transition metals as catalysts of "autoxidation" reactions
    • Miller, D. M.; Buettner, G. R.; Aust, S. D. Transition metals as catalysts of "autoxidation" reactions Free Radical Biol. Med. 1990, 8, 95-108 10.1016/0891-5849(90)90148-C
    • (1990) Free Radical Biol. Med. , vol.8 , pp. 95-108
    • Miller, D.M.1    Buettner, G.R.2    Aust, S.D.3
  • 4
    • 0002789825 scopus 로고
    • Oxygen with phenols and related reactions in musts, wines, and model systems: Observations and practical implications
    • Singleton, V. Oxygen with phenols and related reactions in musts, wines, and model systems: Observations and practical implications Am. J. Enol. Vitic. 1987, 38, 69-77
    • (1987) Am. J. Enol. Vitic. , vol.38 , pp. 69-77
    • Singleton, V.1
  • 5
    • 33746477240 scopus 로고    scopus 로고
    • Oxidation of wine phenolics: A critical evaluation and hypotheses
    • Waterhouse, A. L.; Laurie, V. F. Oxidation of wine phenolics: A critical evaluation and hypotheses Am. J. Enol. Vitic. 2006, 57, 306-313
    • (2006) Am. J. Enol. Vitic. , vol.57 , pp. 306-313
    • Waterhouse, A.L.1    Laurie, V.F.2
  • 6
    • 76449107209 scopus 로고    scopus 로고
    • Controlling the fenton reaction in wine
    • Elias, R. J.; Waterhouse, A. L. Controlling the fenton reaction in wine J. Agric. Food Chem. 2010, 58, 1699-1707 10.1021/jf903127r
    • (2010) J. Agric. Food Chem. , vol.58 , pp. 1699-1707
    • Elias, R.J.1    Waterhouse, A.L.2
  • 7
    • 84883311051 scopus 로고    scopus 로고
    • Reactions involving iron in mediating catechol oxidation in model wine
    • Danilewicz, J. C. Reactions involving iron in mediating catechol oxidation in model wine Am. J. Enol. Vitic. 2013, 64, 316-324 10.5344/ajev.2013.12137
    • (2013) Am. J. Enol. Vitic. , vol.64 , pp. 316-324
    • Danilewicz, J.C.1
  • 8
    • 84973129977 scopus 로고    scopus 로고
    • Reaction mechanisms of metals with hydrogen sulfide and thiols in model wine. Part 1: Copper-catalyzed oxidation
    • Kreitman, G. Y.; Danilewicz, J. C.; Jeffery, D. W.; Elias, R. J. Reaction mechanisms of metals with hydrogen sulfide and thiols in model wine. Part 1: Copper-catalyzed oxidation J. Agric. Food Chem. 2016, 10.1021/acs.jafc.6b00641
    • (2016) J. Agric. Food Chem.
    • Kreitman, G.Y.1    Danilewicz, J.C.2    Jeffery, D.W.3    Elias, R.J.4
  • 9
    • 66149097306 scopus 로고    scopus 로고
    • Identification of free radical intermediates in oxidized wine using electron paramagnetic resonance spin trapping
    • Elias, R. J.; Andersen, M. L.; Skibsted, L. H.; Waterhouse, A. L. Identification of free radical intermediates in oxidized wine using electron paramagnetic resonance spin trapping J. Agric. Food Chem. 2009, 57, 4359-4365 10.1021/jf8035484
    • (2009) J. Agric. Food Chem. , vol.57 , pp. 4359-4365
    • Elias, R.J.1    Andersen, M.L.2    Skibsted, L.H.3    Waterhouse, A.L.4
  • 10
    • 45749145778 scopus 로고    scopus 로고
    • Mechanism of interaction of polyphenols, oxygen, and sulfur dioxide in model wine and wine
    • 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
    • (2008) Am. J. Enol. Vitic. , vol.59 , pp. 128-136
    • Danilewicz, J.C.1    Seccombe, J.T.2    Whelan, J.3
  • 11
    • 77955778574 scopus 로고    scopus 로고
    • Further studies on the mechanism of interaction of polyphenols, oxygen and sulfite in wine
    • Danilewicz, J. C.; Wallbridge, P. J. Further studies on the mechanism of interaction of polyphenols, oxygen and sulfite in wine Am. J. Enol. Vitic. 2010, 61, 166-175
    • (2010) Am. J. Enol. Vitic. , vol.61 , pp. 166-175
    • Danilewicz, J.C.1    Wallbridge, P.J.2
  • 12
    • 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 10.1016/j.aca.2009.11.016
    • (2010) Anal. Chim. Acta , vol.660 , pp. 102-109
    • Nikolantonaki, M.1    Chichuc, I.2    Teissedre, P.-L.3    Darriet, P.4
  • 13
    • 84865654259 scopus 로고    scopus 로고
    • A method to quantify quinone reaction rates with wine relevant nucleophiles: A key to understanding oxidative loss of varietal thiols
    • Nikolantonaki, M.; Waterhouse, A. A method to quantify quinone reaction rates with wine relevant nucleophiles: A key to understanding oxidative loss of varietal thiols J. Agric. Food Chem. 2012, 60, 8484-8491 10.1021/jf302017j
    • (2012) J. Agric. Food Chem. , vol.60 , pp. 8484-8491
    • Nikolantonaki, M.1    Waterhouse, A.2
  • 14
    • 33847763196 scopus 로고    scopus 로고
    • Chemistry of iron sulfides
    • Rickard, D.; Luther, G. W. Chemistry of iron sulfides Chem. Rev. 2007, 107, 514-562 10.1021/cr0503658
    • (2007) Chem. Rev. , vol.107 , pp. 514-562
    • Rickard, D.1    Luther, G.W.2
  • 15
    • 0005182929 scopus 로고
    • Studies on the reactions of ferric iron with glutathione and some related thiols. Part II. Complex formation in the pH range three to seven
    • Hamed, M. Y.; Silver, J. Studies on the reactions of ferric iron with glutathione and some related thiols. Part II. Complex formation in the pH range three to seven Inorg. Chim. Acta 1983, 80, 115-122 10.1016/S0020-1693(00)91271-4
    • (1983) Inorg. Chim. Acta , vol.80 , pp. 115-122
    • Hamed, M.Y.1    Silver, J.2
  • 16
    • 0041006722 scopus 로고
    • Studies on the reactions of ferric iron with glutathione and some related thiols. Part III. A study of the iron catalyzed oxidation of glutathione by molecular oxygen
    • Hamed, M. Y.; Silver, J.; Wilson, M. T. Studies on the reactions of ferric iron with glutathione and some related thiols. Part III. A study of the iron catalyzed oxidation of glutathione by molecular oxygen Inorg. Chim. Acta 1983, 80, 237-244 10.1016/S0020-1693(00)91289-1
    • (1983) Inorg. Chim. Acta , vol.80 , pp. 237-244
    • Hamed, M.Y.1    Silver, J.2    Wilson, M.T.3
  • 17
    • 0342634259 scopus 로고
    • The oxidation of cysteine by iron and hydrogen peroxide
    • Neville, R. The oxidation of cysteine by iron and hydrogen peroxide J. Am. Chem. Soc. 1957, 79, 2456-2457 10.1021/ja01567a028
    • (1957) J. Am. Chem. Soc. , vol.79 , pp. 2456-2457
    • Neville, R.1
  • 18
    • 84901854097 scopus 로고    scopus 로고
    • Role of tartaric and malic acids in wine oxidation
    • Danilewicz, J. C. Role of tartaric and malic acids in wine oxidation J. Agric. Food Chem. 2014, 62, 5149-5155 10.1021/jf5007402
    • (2014) J. Agric. Food Chem. , vol.62 , pp. 5149-5155
    • Danilewicz, J.C.1
  • 19
    • 84925016230 scopus 로고    scopus 로고
    • Copper(II) addition to white wines containing hydrogen sulfide: Residual copper concentration and activity
    • Clark, A. C.; Grant-Preece, P.; Cleghorn, N.; Scollary, G. R. Copper(II) addition to white wines containing hydrogen sulfide: Residual copper concentration and activity Aust. J. Grape Wine Res. 2015, 21, 30-39 10.1111/ajgw.12114
    • (2015) Aust. J. Grape Wine Res. , vol.21 , pp. 30-39
    • Clark, A.C.1    Grant-Preece, P.2    Cleghorn, N.3    Scollary, G.R.4
  • 20
    • 84858342237 scopus 로고    scopus 로고
    • The multi-element determination and regional discrimination of Australian wines
    • Martin, A. E.; Watling, R. J.; Lee, G. S. The multi-element determination and regional discrimination of Australian wines Food Chem. 2012, 133, 1081-1089 10.1016/j.foodchem.2012.02.013
    • (2012) Food Chem. , vol.133 , pp. 1081-1089
    • Martin, A.E.1    Watling, R.J.2    Lee, G.S.3
  • 21
    • 24144480539 scopus 로고    scopus 로고
    • Metal sulfide cluster complexes and their biogeochemical importance in the environment
    • Luther, G. W.; Rickard, D. T. Metal sulfide cluster complexes and their biogeochemical importance in the environment J. Nanopart. Res. 2005, 7, 389-407 10.1007/s11051-005-4272-4
    • (2005) J. Nanopart. Res. , vol.7 , pp. 389-407
    • Luther, G.W.1    Rickard, D.T.2
  • 22
    • 33748049507 scopus 로고    scopus 로고
    • Metal sulfide complexes and clusters
    • Rickard, D.; Luther, G. W. Metal sulfide complexes and clusters Rev. Mineral. Geochem. 2006, 61, 421-504 10.2138/rmg.2006.61.8
    • (2006) Rev. Mineral. Geochem. , vol.61 , pp. 421-504
    • Rickard, D.1    Luther, G.W.2
  • 23
    • 84906062624 scopus 로고    scopus 로고
    • Quantitative analysis of free and bonded forms of volatile sulfur compouds in wine. Basic methodologies and evidences showing the existence of reversible cation-complexed forms
    • Franco-Luesma, E.; Ferreira, V. Quantitative analysis of free and bonded forms of volatile sulfur compouds in wine. Basic methodologies and evidences showing the existence of reversible cation-complexed forms J. Chromatogr. A 2014, 1359, 8-15 10.1016/j.chroma.2014.07.011
    • (2014) J. Chromatogr. A , vol.1359 , pp. 8-15
    • Franco-Luesma, E.1    Ferreira, V.2
  • 24
    • 84949034814 scopus 로고    scopus 로고
    • Reductive off-odors in wines: Formation and release of H2S and methanethiol during the accelerated anoxic storage of wines
    • Franco-Luesma, E.; Ferreira, V. Reductive off-odors in wines: Formation and release of H2S and methanethiol during the accelerated anoxic storage of wines Food Chem. 2016, 199, 42-50 10.1016/j.foodchem.2015.11.111
    • (2016) Food Chem. , vol.199 , pp. 42-50
    • Franco-Luesma, E.1    Ferreira, V.2
  • 25
    • 33750018633 scopus 로고    scopus 로고
    • Removal of H2S via an iron catalytic cycle and iron sulfide precipitation in the water column of dead end tributaries
    • Ma, S.; Noble, A.; Butcher, D.; Trouwborst, R. E.; Luther, G. W. Removal of H2S via an iron catalytic cycle and iron sulfide precipitation in the water column of dead end tributaries Estuarine, Coastal Shelf Sci. 2006, 70, 461-472 10.1016/j.ecss.2006.06.033
    • (2006) Estuarine, Coastal Shelf Sci. , vol.70 , pp. 461-472
    • Ma, S.1    Noble, A.2    Butcher, D.3    Trouwborst, R.E.4    Luther, G.W.5
  • 26
    • 84872877185 scopus 로고    scopus 로고
    • Investigation of ethyl radical quenching by phenolics and thiols in model wine
    • Kreitman, G. Y.; Laurie, V. F.; Elias, R. J. Investigation of ethyl radical quenching by phenolics and thiols in model wine J. Agric. Food Chem. 2013, 61, 685-692 10.1021/jf303880g
    • (2013) J. Agric. Food Chem. , vol.61 , pp. 685-692
    • Kreitman, G.Y.1    Laurie, V.F.2    Elias, R.J.3
  • 27
    • 84879285119 scopus 로고    scopus 로고
    • Determination of aminothiols by liquid chromatography with amperometric detection at a silver electrode: Application to white wines
    • Sarakbi, A.; Aydogmus, Z.; Dago, A.; Mertens, D.; Dewert, J. Y.; Kauffmann, J. M. Determination of aminothiols by liquid chromatography with amperometric detection at a silver electrode: Application to white wines Anal. Chim. Acta 2013, 786, 22-28 10.1016/j.aca.2013.04.070
    • (2013) Anal. Chim. Acta , vol.786 , pp. 22-28
    • Sarakbi, A.1    Aydogmus, Z.2    Dago, A.3    Mertens, D.4    Dewert, J.Y.5    Kauffmann, J.M.6
  • 28
    • 0035017392 scopus 로고    scopus 로고
    • Automated HPLC method for the measurement of free amino acids including cysteine in musts and wines; First applications
    • Pripis-Nicolau, L.; de Revel, G.; Marchand, S.; Beloqui, A. A.; Bertrand, A. Automated HPLC method for the measurement of free amino acids including cysteine in musts and wines; first applications J. Sci. Food Agric. 2001, 81, 731-738 10.1002/jsfa.871
    • (2001) J. Sci. Food Agric. , vol.81 , pp. 731-738
    • Pripis-Nicolau, L.1    De Revel, G.2    Marchand, S.3    Beloqui, A.A.4    Bertrand, A.5
  • 29
    • 83455219451 scopus 로고    scopus 로고
    • Stability of varietal thiols in commercial sauvignon blanc wines
    • Herbst-Johnstone, M.; Nicolau, L.; Kilmartin, P. a. Stability of varietal thiols in commercial sauvignon blanc wines Am. J. Enol. Vitic. 2011, 62, 495-502 10.5344/ajev.2011.11023
    • (2011) Am. J. Enol. Vitic. , vol.62 , pp. 495-502
    • Herbst-Johnstone, M.1    Nicolau, L.2    Kilmartin, P.A.3
  • 31
    • 77956243390 scopus 로고    scopus 로고
    • Selective determination of volatile sulfur compounds in wine by gas chromatography with sulfur chemiluminescence detection
    • Siebert, T. E.; Solomon, M. R.; 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 10.1021/jf102008r
    • (2010) J. Agric. Food Chem. , vol.58 , pp. 9454-9462
    • Siebert, T.E.1    Solomon, M.R.2    Pollnitz, A.P.3    Jeffery, D.W.4
  • 32
    • 0000656784 scopus 로고    scopus 로고
    • Hydrogen sulfide reactivity with thiols in the presence of copper(II) in hydroalcoholic solutions or cognac brandies: Formation of symmetrical and unsymmetrical dialkyl trisulfides
    • Nedjma, M.; Hoffmann, N. Hydrogen sulfide reactivity with thiols in the presence of copper(II) in hydroalcoholic solutions or cognac brandies: Formation of symmetrical and unsymmetrical dialkyl trisulfides J. Agric. Food Chem. 1996, 44, 3935-3938 10.1021/jf9602582
    • (1996) J. Agric. Food Chem. , vol.44 , pp. 3935-3938
    • Nedjma, M.1    Hoffmann, N.2
  • 34
    • 84953367655 scopus 로고    scopus 로고
    • Wine metabolomics reveals new sulfonated products in bottled white wines, promoted by small amounts of oxygen
    • Arapitsas, P.; Ugliano, M.; Perenzoni, D.; Angeli, A.; Pangrazzi, P.; Mattivi, F. Wine metabolomics reveals new sulfonated products in bottled white wines, promoted by small amounts of oxygen J. Chromatogr. A 2016, 1429, 155-165 10.1016/j.chroma.2015.12.010
    • (2016) J. Chromatogr. A , vol.1429 , pp. 155-165
    • Arapitsas, P.1    Ugliano, M.2    Perenzoni, D.3    Angeli, A.4    Pangrazzi, P.5    Mattivi, F.6
  • 35
    • 84890695008 scopus 로고    scopus 로고
    • Effects of five metals on the evolution of hydrogen sulfide, methanethiol and dimethyl sulfide during anaerobic storage of chardonnay and shiraz wine
    • Viviers, M. Z.; Smith, M. E.; Wilkes, E. N.; Smith, P. A. Effects of five metals on the evolution of hydrogen sulfide, methanethiol and dimethyl sulfide during anaerobic storage of chardonnay and shiraz wine J. Agric. Food Chem. 2013, 61, 12385-12396 10.1021/jf403422x
    • (2013) J. Agric. Food Chem. , vol.61 , pp. 12385-12396
    • Viviers, M.Z.1    Smith, M.E.2    Wilkes, E.N.3    Smith, P.A.4


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