Research-Article| Volume 72, ISSUE 3, P604-613, March 1989

Download started.


Generation of Swiss Cheese Flavor Components by the Reaction of Amino Acids with Carbonyl Compounds1

      This paper is only available as a PDF. To read, Please Download here.


      Previous work has shown that carbonyl-amino acid complexes are important in generating flavors in aqueous extracts of cheeses and Lactobacillus bulgaricus cultures. Glyoxal, methylglyoxal, dihydroxy-acetone, and ethanal were prominant among the carbonyls in such extracts, so the ability of these carbonyls to generate flavors from various amino acids at room temperature was evaluated. Gas chromatography and mass spectrometry of ether extracts of these mixtures were used to identify the particular compounds responsible for the aromas. The amino acids important in the flavor-generating reactions were valine, leucine, isoleucine, methionine, cysteine, phenylalanine, proline, and lysine. Isovaleraldehyde, 2-methylbutanal, isobutanal, phenylacetal-dehyde, and methional, respectively, were formed from leucine, isoleucine, valine, phenylalanine, and methionine via the Strecker degradation. Important flavors in addition to the aldehydes produced by the Strecker degradation were benzaldehyde and acetophenone from phenylalanine, dimethyldisulfide and dimethyltrisulfide from methionine, 2-acetylthiazole from cysteine and methylglyoxal, alkylpyrazines from lysine and dihydroxyacetone, 2-acetyl-1-pyrroline from reaction of certain carbonyls with proline and lysine, 2,5-dimethyl-4-OH-3(2H)-furanone from methylglyoxal, and 2-methylbenzaldehyde from proline and ethanal. Other volatiles identified include isomers of acetyl-methyl-2,3-dihydropyrrolizine from the proline-methylglyoxal and proline-di-hydroxyacetone complexes and δ-valerolactam from the lysine-carbonyl combinations. The reaction products accounted for most of the flavors previously noted in aqueous cheese extracts and cultures of cheese microorganisms.


        • Adda J.
        • Gripon J.
        • Vassal L.
        The chemistry of flavor and texture generation incheese.
        Food Chem. 1982; 9: 115
        • Adda J.
        • Roger S.
        • Dumont J.P.
        Some recent advances in the knowledge of cheese flavors.
        in: Charalambous G. Inglett G. Flavors of food and beverages: chemistry andtechnology. Academic Press, New York, NY1978: 65-74
        • Aston J.W.
        • Dulley J.R.
        Cheddar cheese flavor.
        Aust. J. Dairy Technol. 1982; 37: 59
        • Ballance P.E.
        Production of volatile compounds related to the flavor of foods from the Strecker degradation of DL-methionine.
        J. Sci. Food Agric. 1961; 12: 532
        • Biede S.L.
        • Hammond E.G.
        Swiss cheese flavor: I Chemical analysis.
        J. Dairy Sci. 1979; 62: 227
        • Biede S.L.
        • Hammond E.G.
        Swiss cheese flavor: II Organoleptic analysis.
        J. DairySci. 1979; 62: 238
        • Bosset J.O.
        • Liardon R.
        The aroma composition of Swiss Guyere cheese: II Theneutral volatile components.
        Lebensm. Wiss. Technol. 1984; 17: 359
        • Buttery R.G.
        • Ling L.C.
        • Juliano B.O.
        • Turnbaugh J.G.
        Cooked rice aroma and 2-acetyl-1-pyrroline.
        J. Agric. Food Chem. 1983; 31: 823
        • Hunter I.R.
        • Walden M.K.
        • Scherer J.R.
        • Lundin R.E.
        Preparation and properties of 1,4,5,6-tetrahydro-2-acetopyridine, a cracker odorconstituent of bread aroma.
        Cereal Chem. 1969; 46: 189
        • Keeney M.
        • Day E.A.
        Probable role ofthe Strecker degradation of amino acids in the development of cheese flavor.
        J. Dairy Sci. 1957; 40: 874
        • Kowalewska J.
        • Zelazowska H.
        • Babuchowski A.
        • Hammond E.G.
        • Glatz B.A.
        • Ross F.
        The isolation of aroma bearing material from Lactobacillus bulgaricus culture and cheese.
        J.Dairy Sci. 1985; 68: 2165
        • Langler J.E.
        • Libbey L.M.
        • Day E.A.
        Identification and evaluation of selected compounds in Swiss cheese flavor.
        J. Agric. Food Chem. 1967; 15: 386
        • Langsrud T.
        • Reinbold G.W.
        Flavor development and microbiology of Swiss cheese—areview III. Ripening and flavor production.
        J. Milk Food Technol. 1973; 36: 593
        • Law B.A.
        Microorganisms and enzymes in the maturation of cheeses.
        Prog. Ind. Microbiol. 1984; 19: 245
        • Law B.A.
        • Wigmore A.
        Effect of commercial lipolytic enzymes on flavor developmentin Cheddar cheese.
        J. Soc. Dairy Technol. 1985; 38: 86
        • Lin S.S.
        Alkylpyrazines in processed American cheese.
        J. Agric. Food Chem. 1976; 24: 1252
        • McGugan W.A.
        Cheddar cheese flavor a review of current progress.
        J. Agric. Food Chem. 1975; 23: 1047
        • McGugan W.A.
        • Howsam S.G.
        • Elliott J.A.
        • Emmons D.B.
        • Reiter B.
        • Sharpe M.E.
        Neutral volatile in Cheddar cheese made asepticallywith and without starter culture.
        J. Dairy Res. 1968; 35: 237
        • Ney K.H.
        Recent advances in cheese flavorresearch.
        in: Charalambous G. Inglett G. The quality of foods and beverages:chemistry and technology. Academic Press., NewYork, NY1981: 389-435
        • Parliament T.H.
        • Kolar M.G.
        • Rizzo D.J.
        Volatile components of Limberger cheese.
        J. Agric. Food Chem. 1982; 30: 1006
        • Reps A.
        • Hammond E.G.
        • Glatz B.A.
        Carbonyl compounds produced by the growth of Lactobacillus bulgaricus.
        J. Dairy Sci. 1987; 70: 559
        • Schieberle P.
        • Grosch W.
        Identification of the volatile flavour compounds of wheat bread crust-comparison with rye bread crust.
        Z. Lebensm. Unters. Forsch. 1985; 180: 474
        • Schieberle P.
        • Grosch W.
        Evaluation of the flavour of wheat and rye bread crusts by aroma extract dilution analysis.
        Z. Lebensm. Unters. Forsch. 1987; 185: 111
        • Shaw P.E.
        • Berry R.E.
        Hexose amino acid degradation studies involving formation of pyrroles, furans, and other low molecular weight products.
        J. Agric. Food Chem. 1977; 25: 641
        • Sloot D.
        • Hofman H.J.
        Alkylpyrazinesin Emmental cheese.
        J. Agric. Food Chem. 1975; 23: 358
        • Tressl R.
        • Helak B.
        • Griinewald K.G.
        • Silwar R.
        Formation of flavor components from proline, hydroxyprpline and sulfur containing amino acids.
        J. Chem. Tech. Anal. Colloq. Int. Aromes Alment. 1982; 1982: 207
        • Tressl R.
        • Rewicke D.
        • Helak B.
        • Kamper-schroer H.
        • Martin N.
        Formation of 2,3-dihydro-lH-pyrrolizines as prline specific Maillardproducts.
        J. Agric. Food Chem. 1985; 33: 919
        • Vangtal A.
        • Hammond E.G.
        Correlation of the flavor characteristics of Swiss-typecheeses with chemical parameters.
        J. Dairy Sci. 1986; 69: 2982