메뉴 건너뛰기




Volumn 76, Issue 6, 2011, Pages

The cysteine reaction with diacetyl under wine-like conditions: Proposed mechanisms for mixed origins of 2-methylthiazole, 2-methyl-3-thiazoline, 2-methylthiazolidine, and 2,4,5-trimethyloxazole

Author keywords

Cysteine; Diacetyl; Flavor; Mechanism; Thiazole

Indexed keywords

2,3 BUTANEDIONE; ACETALDEHYDE; ALKANONE; CYSTEINE; DRUG DERIVATIVE; OXAZOLE DERIVATIVE; THIAZOLE DERIVATIVE; VOLATILE ORGANIC COMPOUND;

EID: 79961127687     PISSN: 00221147     EISSN: 17503841     Source Type: Journal    
DOI: 10.1111/j.1750-3841.2011.02261.x     Document Type: Article
Times cited : (16)

References (40)
  • 2
    • 5444245699 scopus 로고    scopus 로고
    • The buttery' attribute of wine diacetyl desirability, spoilage and beyond
    • Bartowsky EJ, Henschke PA. 2004. The buttery' attribute of wine diacetyl desirability, spoilage and beyond. Int J Food Microbiol 96:235-52.
    • (2004) Int J Food Microbiol , vol.96 , pp. 235-252
    • Bartowsky, E.J.1    Henschke, P.A.2
  • 3
    • 57849164196 scopus 로고    scopus 로고
    • Identification of 5-Hydroxy-3-mercapto-2-pentanone in the Maillard reaction of Thiamine, Cysteine, and Xylose
    • Cerny C, Guntz-Dubini R. 2008. Identification of 5-Hydroxy-3-mercapto-2-pentanone in the Maillard reaction of Thiamine, Cysteine, and Xylose. J Agric Food Chem 56:10679-82.
    • (2008) J Agric Food Chem , vol.56 , pp. 10679-10682
    • Cerny, C.1    Guntz-Dubini, R.2
  • 4
    • 0032841588 scopus 로고    scopus 로고
    • Study of the formation mechanisms of some volatile compounds during the aging of sweet fortified wines
    • Cutzach I, Chatonnet P, Dubourdieu D. 1999. Study of the formation mechanisms of some volatile compounds during the aging of sweet fortified wines. J Agric Food Chem 47:2837-46.
    • (1999) J Agric Food Chem , vol.47 , pp. 2837-2846
    • Cutzach, I.1    Chatonnet, P.2    Dubourdieu, D.3
  • 5
    • 0033917373 scopus 로고    scopus 로고
    • Influence of storage conditions on the formation of some volatile compounds in white fortified wines (Vins Doux Naturels) during the aging process
    • Cutzach I, Chatonnet P, Dubourdieu D. 2000. Influence of storage conditions on the formation of some volatile compounds in white fortified wines (Vins Doux Naturels) during the aging process. J Agric Food Chem 48:2340-5.
    • (2000) J Agric Food Chem , vol.48 , pp. 2340-2345
    • Cutzach, I.1    Chatonnet, P.2    Dubourdieu, D.3
  • 6
    • 0002230878 scopus 로고
    • Dicarbonyl compounds and their reduction products in wine. Identification of wine aldehydes
    • In: Maarse H. and van der Heij DG editors. Pays-Bas: Elsevier.
    • de Revel G, Bertrand A. 1993. Dicarbonyl compounds and their reduction products in wine. Identification of wine aldehydes. In: Maarse H. and van der Heij DG editors. Trends in flavour research. Pays-Bas: Elsevier. p 353-61.
    • (1993) Trends in flavour research , pp. 353-361
    • de Revel, G.1    Bertrand, A.2
  • 7
    • 0001191501 scopus 로고    scopus 로고
    • Investigation of the reaction between ammonium sulfide, aldehydes, and α-hydroxyketones or α-dicarbonyls to form some lipid-Maillard interaction products found in cooked beef
    • Elmore JS, Mottram DS. 1997. Investigation of the reaction between ammonium sulfide, aldehydes, and α-hydroxyketones or α-dicarbonyls to form some lipid-Maillard interaction products found in cooked beef. J Agric Food Chem 45:3595-602.
    • (1997) J Agric Food Chem , vol.45 , pp. 3595-3602
    • Elmore, J.S.1    Mottram, D.S.2
  • 8
    • 33947462103 scopus 로고
    • Kinetics of oxime formation; temperature coefficients of rate of formation of several oximes
    • Fitzpatrick FW, Gettler JD. 1956. Kinetics of oxime formation; temperature coefficients of rate of formation of several oximes. J Am Chem Soc 78:530-6.
    • (1956) J Am Chem Soc , vol.78 , pp. 530-536
    • Fitzpatrick, F.W.1    Gettler, J.D.2
  • 9
    • 30044443861 scopus 로고    scopus 로고
    • Monitoring of the principal carbonyl compounds involved in malolactic fermentation of wine by solid-phase microextraction and positive ion chemical ionization GC/MS analysis
    • Flamini R, Dalla Vedova A, Panighel A, Perchiazzi N, Ongarato S. 2005. Monitoring of the principal carbonyl compounds involved in malolactic fermentation of wine by solid-phase microextraction and positive ion chemical ionization GC/MS analysis. J Mass Spectrom 40:1558-64.
    • (2005) J Mass Spectrom , vol.40 , pp. 1558-1564
    • Flamini, R.1    Dalla Vedova, A.2    Panighel, A.3    Perchiazzi, N.4    Ongarato, S.5
  • 10
    • 84948882698 scopus 로고
    • Generation of Swiss cheese flavor components by the reaction of amino-acids with carbonyl-compounds
    • Griffith R, Hammond EG. 1989. Generation of Swiss cheese flavor components by the reaction of amino-acids with carbonyl-compounds. J Dairy Sci 72:604-13.
    • (1989) J Dairy Sci , vol.72 , pp. 604-613
    • Griffith, R.1    Hammond, E.G.2
  • 11
    • 0004619680 scopus 로고
    • Metal ion oxidative decarboxylations. Kinetics and mechanisms of the oxidation of N-benzyliminodiacetic acid with cerium(IV) in acidic perchlorate and acidic sulfate media
    • Hanna SB, Moehlenkamp ME. 1983. Metal ion oxidative decarboxylations. Kinetics and mechanisms of the oxidation of N-benzyliminodiacetic acid with cerium(IV) in acidic perchlorate and acidic sulfate media. J Organic Chem 48:826-32.
    • (1983) J Organic Chem , vol.48 , pp. 826-832
    • Hanna, S.B.1    Moehlenkamp, M.E.2
  • 12
    • 0001055803 scopus 로고    scopus 로고
    • Quantitative model studies on the effectiveness of different precursor systems in the formation of the intense food odorants 2-furfurylthiol and 2-methyl-3-furanthiol
    • Hofmann T, Schieberle P. 1998. Quantitative model studies on the effectiveness of different precursor systems in the formation of the intense food odorants 2-furfurylthiol and 2-methyl-3-furanthiol. J Agric Food Chem 46:235-41.
    • (1998) J Agric Food Chem , vol.46 , pp. 235-241
    • Hofmann, T.1    Schieberle, P.2
  • 13
    • 0000328328 scopus 로고    scopus 로고
    • Analysis of volatile compounds formed from fish oil heated with cysteine and trimethylamine oxide
    • Horiuchi M, Umano K, Shibamoto T. 1998. Analysis of volatile compounds formed from fish oil heated with cysteine and trimethylamine oxide. J Agric Food Chem 46:5232-7.
    • (1998) J Agric Food Chem , vol.46 , pp. 5232-5237
    • Horiuchi, M.1    Umano, K.2    Shibamoto, T.3
  • 14
    • 0001376676 scopus 로고    scopus 로고
    • Mechanistic studies on the formation of thiazolidine and structurally related thiazines in a cysteamine/2,3-butanedione model system
    • Huang TC, Su YM, Ho CT. 1998. Mechanistic studies on the formation of thiazolidine and structurally related thiazines in a cysteamine/2, 3-butanedione model system. J Agric Food Chem 46:664-7.
    • (1998) J Agric Food Chem , vol.46 , pp. 664-667
    • Huang, T.C.1    Su, Y.M.2    Ho, C.T.3
  • 15
    • 70349314616 scopus 로고    scopus 로고
    • Degradation of glucose: reinvestigation of reactive α-dicarbonyl compounds
    • Jenny G, Glomb MA. 2009. Degradation of glucose: reinvestigation of reactive α-dicarbonyl compounds. J Agric Food Chem 57:8591-7.
    • (2009) J Agric Food Chem , vol.57 , pp. 8591-8597
    • Jenny, G.1    Glomb, M.A.2
  • 16
    • 0001074989 scopus 로고
    • Gas chromatographic characterization of organic substances in the retention index system
    • Kovats E. 1965. Gas chromatographic characterization of organic substances in the retention index system. Adv Chromatogr 1:229-47.
    • (1965) Adv Chromatogr , vol.1 , pp. 229-247
    • Kovats, E.1
  • 17
    • 71349085673 scopus 로고    scopus 로고
    • Evolution of the aroma composition of wines supplemented with grape flavour precursors from different varietals during accelerated wine ageing
    • Loscos N, Hernandez-Orte P, Cacho J, Ferreira V. 2010. Evolution of the aroma composition of wines supplemented with grape flavour precursors from different varietals during accelerated wine ageing. Food Chem 120:205-16.
    • (2010) Food Chem , vol.120 , pp. 205-216
    • Loscos, N.1    Hernandez-Orte, P.2    Cacho, J.3    Ferreira, V.4
  • 18
    • 0011446239 scopus 로고
    • Réaction générale des acides amines sur les sucres: ses concéquences biologiques
    • Maillard LC. 1912. Réaction générale des acides amines sur les sucres: ses concéquences biologiques. Société de Biologie 72:599-601.
    • (1912) Société de Biologie , vol.72 , pp. 599-601
    • Maillard, L.C.1
  • 19
    • 74549147267 scopus 로고    scopus 로고
    • A HPLC fluorescence-based method for glutathione derivatives quantification in must and wine
    • Marchand S, de Revel G. 2009. A HPLC fluorescence-based method for glutathione derivatives quantification in must and wine. Anal Chim Acta 660:158-63.
    • (2009) Anal Chim Acta , vol.660 , pp. 158-163
    • Marchand, S.1    de Revel, G.2
  • 20
    • 0033790025 scopus 로고    scopus 로고
    • Approaches to wine aroma: release of aroma compounds from reactions between cysteine and carbonyl compounds in wine
    • Marchand S, de Revel G, Bertrand A. 2000. Approaches to wine aroma: release of aroma compounds from reactions between cysteine and carbonyl compounds in wine. J Agric Food Chem. 48:4890-5.
    • (2000) J Agric Food Chem. , vol.48 , pp. 4890-4895
    • Marchand, S.1    de Revel, G.2    Bertrand, A.3
  • 21
    • 0037048767 scopus 로고    scopus 로고
    • Possible mechanism for involvement of cysteine in aroma production in wine
    • Marchand S, de Revel G, Vercauteren J, Bertrand A. 2002. Possible mechanism for involvement of cysteine in aroma production in wine. J Agric Food Chem 50:6160-4.
    • (2002) J Agric Food Chem , vol.50 , pp. 6160-6164
    • Marchand, S.1    de Revel, G.2    Vercauteren, J.3    Bertrand, A.4
  • 23
    • 34249857793 scopus 로고    scopus 로고
    • Influence of sulfur amino acids on the volatile and nonvolatile components of cooked salmon (Salmo salar)
    • Methven L, Tsoukka M, Oruna-Concha MJ, Parker JK, Mottram DS. 2007. Influence of sulfur amino acids on the volatile and nonvolatile components of cooked salmon (Salmo salar). J Agric Food Chem 55:1427-36.
    • (2007) J Agric Food Chem , vol.55 , pp. 1427-1436
    • Methven, L.1    Tsoukka, M.2    Oruna-Concha, M.J.3    Parker, J.K.4    Mottram, D.S.5
  • 24
    • 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 PL, Darriet P. 2010. Reactivity of volatile thiols with polyphenols in a wine-model medium: impact of oxygen, iron, and sulfur dioxide. Anal Chim Acta. 660:102-9.
    • (2010) Anal Chim Acta. , vol.660 , pp. 102-109
    • Nikolantonaki, M.1    Chichuc, I.2    Teissedre, P.L.3    Darriet, P.4
  • 25
    • 7244221416 scopus 로고    scopus 로고
    • Origin and mechanistic pathways of formation of the parent furan - a food toxicant
    • Perez Locas C, Yaylayan VA. 2004. Origin and mechanistic pathways of formation of the parent furan - a food toxicant. J Agric Food Chem 52: 6830-6.
    • (2004) J Agric Food Chem , vol.52 , pp. 6830-6836
    • Perez Locas, C.1    Yaylayan, V.A.2
  • 26
    • 0009763888 scopus 로고
    • Volatile products in the reaction of amino acids with diacetyl. Z Lebensm
    • Piloty V, Baltes W. 1979. Volatile products in the reaction of amino acids with diacetyl. Z Lebensm. Unters Forsch 168:374-80.
    • (1979) Unters Forsch , vol.168 , pp. 374-380
    • Piloty, V.1    Baltes, W.2
  • 27
    • 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, Anocibar A, Bertrand A. 2001. Automated HPLC method for the measurement of free amino acids including cysteine in musts and wines: first applications. J Sci Food Agric 81:731-8.
    • (2001) J Sci Food Agric , vol.81 , pp. 731-738
    • Pripis-Nicolau, L.1    de Revel, G.2    Marchand, S.3    Anocibar, A.4    Bertrand, A.5
  • 28
  • 29
    • 0038492797 scopus 로고    scopus 로고
    • 3-Hydroxy-4,5-dimethyl-2(5H)-furanone: a key odorant of the typical aroma of oxidative aged port wine
    • Silva Ferreira AC, Barbe J-C, Bertrand A. 2003. 3-Hydroxy-4, 5-dimethyl-2(5H)-furanone: a key odorant of the typical aroma of oxidative aged port wine. J Agric Food Chem. 51:4356-63.
    • (2003) J Agric Food Chem. , vol.51 , pp. 4356-4363
    • Silva Ferreira, A.C.1    Barbe, J.-C.2    Bertrand, A.3
  • 30
    • 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. 2008. The role of cysteine and cysteine-S conjugates as odour precursors in the flavour and fragrance industry. Flav Frag J 23:369-81.
    • (2008) Flav Frag J , vol.23 , pp. 369-381
    • Starkenmann, C.1    Troccaz, M.2    Howell, K.3
  • 32
    • 0037433122 scopus 로고    scopus 로고
    • Role of certain volatile thiols in the bouquet of aged champagne wines
    • Tominaga T, Guimbertau G, Dubourdieu D. 2003. Role of certain volatile thiols in the bouquet of aged champagne wines. J Agric Food Chem 51:1016-20.
    • (2003) J Agric Food Chem , vol.51 , pp. 1016-1020
    • Tominaga, T.1    Guimbertau, G.2    Dubourdieu, D.3
  • 33
    • 0000932045 scopus 로고
    • Volatile chemicals formed in the headspace of a heated d-glucose/l-cysteine maillard model system
    • Umano K, Hagi Y, Nakahara K, Shyoji A, Shibamoto T. 1995. Volatile chemicals formed in the headspace of a heated d-glucose/l-cysteine maillard model system. J Agric Food Chem 43:2212-8.
    • (1995) J Agric Food Chem , vol.43 , pp. 2212-2218
    • Umano, K.1    Hagi, Y.2    Nakahara, K.3    Shyoji, A.4    Shibamoto, T.5
  • 34
    • 84984268931 scopus 로고
    • La chimie des arômes: les hétérocycles
    • Vernin G, Metzger J. 1981. La chimie des arômes: les hétérocycles. Bull Soc Chim Belg 90:553-83.
    • (1981) Bull Soc Chim Belg , vol.90 , pp. 553-583
    • Vernin, G.1    Metzger, J.2
  • 35
    • 0027111582 scopus 로고
    • Kinetics and thermal-degradation of the fructose methionine amadori intermediates - GC-MC/specma data-bank identification of volatile aroma compounds
    • Vernin G, Metzger J, Boniface C, Murello MH, Siouffi A, Larice JL, Parkanyi C. 1992. Kinetics and thermal-degradation of the fructose methionine amadori intermediates - GC-MC/specma data-bank identification of volatile aroma compounds. Carbohydr Res 230:15-29.
    • (1992) Carbohydr Res , vol.230 , pp. 15-29
    • Vernin, G.1    Metzger, J.2    Boniface, C.3    Murello, M.H.4    Siouffi, A.5    Larice, J.L.6    Parkanyi, C.7
  • 36
    • 0025081420 scopus 로고
    • Recognition of trypsin autolysis products by high-performance liquid chromatography and mass spectrometry
    • Vestling M, Murphy C, Fenselau C. 1990. Recognition of trypsin autolysis products by high-performance liquid chromatography and mass spectrometry. Anal Chem 62:2391-4.
    • (1990) Anal Chem , vol.62 , pp. 2391-2394
    • Vestling, M.1    Murphy, C.2    Fenselau, C.3
  • 37
  • 38
    • 0032854047 scopus 로고    scopus 로고
    • Origin of 2,3-pentanedione and 2,3-butanedione in D-glucose/L-alanine maillard model systems
    • Yaylayan VA, Keyhani A. 1999. Origin of 2, 3-pentanedione and 2, 3-butanedione in D-glucose/L-alanine maillard model systems. J Agric Food Chem 47(8):3280-4.
    • (1999) J Agric Food Chem , vol.47 , Issue.8 , pp. 3280-3284
    • Yaylayan, V.A.1    Keyhani, A.2
  • 39
    • 0000322861 scopus 로고
    • Microwave-induced volatiles of the Maillard model system under different pH conditions
    • Yeo HCH, Shibamoto T. 1991. Microwave-induced volatiles of the Maillard model system under different pH conditions. J Agric Food Chem 39:370-3.
    • (1991) J Agric Food Chem , vol.39 , pp. 370-373
    • Yeo, H.C.H.1    Shibamoto, T.2
  • 40
    • 77949487131 scopus 로고    scopus 로고
    • Aroma compounds generated from thermal reaction of L-ascorbic acid with L-cysteine
    • Yu AN, Zhang AD. 2010. Aroma compounds generated from thermal reaction of L-ascorbic acid with L-cysteine. Food Chem 121:1060-5.
    • (2010) Food Chem , vol.121 , pp. 1060-1065
    • Yu, A.N.1    Zhang, A.D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.