Abstract
The Maillard reaction is a type of non-enzymic browning which involves the reaction of carbonyl compounds, especially reducing sugars, with cornpounds which possess a free amino group, such as amino acids, amines and proteins. In most foods, the ε-amino groups of the lysine residues of proteins are the most important source of free amino groups, and the ease with which they take part in the reaction explains why the Maillard reaction is the most important route to nutritional damage of food proteins. 1,2 The Maillard reaction in fact comprises a complex network of intertwining reactions and takes place during food processing, especially when heat treatment is involved, and also on storage. Apart from resulting in nutritional damage, the Maillard reaction is also primarily responsible for the development of aroma and colour, which may be desirable or undesirable, in heated foods. It also results in the formation of potentially toxic compounds and in the development of components with antioxidant properties.3 In addition, it occurs in vivo. The Maillard reaction and its ramifications are so important that four symposia have been devoted to it over the last 12 years.4–7
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References
Hurrell, R. F., Reactions of food proteins during processing and storage and their nutritional consequences. In Developments in Food Proteins, Vol. 3, ed. B. J. F. Hudson. Elsevier, London, 1984, pp. 213–244.
Hurrell, R. F., Food manufacturing processes and their influence on the nutritional quality of foods. In Nutritional Impact of Food Processing, ed. J. C. Somogyi & H. R. Miller. Bibl. Nutr. Dieta. No. 43. Karger, Basel, 1989, pp. 125–139.
Nursten, H. E., Maillard browning reactions in dried foods. In Concentration and Drying of Foods, ed. D. MacCarthy. Elsevier Applied Science, London, 1986, pp. 53–68.
Eriksson, C., ed., Mallard Reactions in Food. Progress in Food and Nutrition Science, Vol. 5 (1–6). Pergamon, Oxford, 1981.
Waller, G. R. & Feather, M. S., ed. The Maillard Reaction in Foods and Nutrition. ACS Symp. Ser. 215, ACS, Washington DC, 1983.
Fujimaki, M., Namiki, M. & Kato, H., ed. Amino-Carbonyl Reactions in Food and Biological Systems. Developments in Food Science, Vol. 13. Elsevier, Amsterdam, 1986.
Finot, P. A., Aeschbacher, H. U., Hurrell, R. F. & Liardon, R., ed. The Maillard Reaction in Food Processing, Human Nutrition and Physiology. Birkhäuser, Basel, 1990.
Hodge, J. E., Chemistry of browning reactions in model systems. J. Agric. Food Chem., 1 (1953) 928–943.
Ellis, G. P., The Maillard reaction. Adv. Carbohydr. Chem., 14 (1959) 63–134.
Reynolds, T. H., Chemistry of nonenzymic browning. I. The reaction between aldoses and amines. Adv. Food Res., 12 (1963) 1–52.
Reynolds, T. H., Chemistry of nonenzymic browning. II. Adv. Food Res., 14 (1965) 167–283.
Nursten, H. E., Recent developments in studies of the Maillard reaction. Food Chem., 6 (1981) 263–277.
Danehy, J. P., Maillard reactions: nonenzymatic browning in food systems with special reference to the development of flavor. Adv. Food Res., 30 (1986) 77–138.
Namiki, M., Chemistry of Maillard reactions: Recent studies on the browning reaction mechanism and the development of antioxidants and mutagens. Adv. Food. Res., 32 (1988) 115–184.
Ledl, F., Chemical pathways of the Maillard reaction. In The Maillard Reaction in Food Processing, Human Nutrition and Physiology, ed. P. A. Finot, H. U. Aeschbacher, R. F. Hurrell & R. Liardon. Birkhäuser, Basel, 1990, pp. 19–42.
Ledl, F. & Schleicher, E., New aspects of the Maillard reaction in foods and in the human body. Angew. Chem. Int. Ed. Engl., 29 (1990) 565–594.
Ames, J. M., Control of the Maillard reaction in food systems. Trends Food Sci. Technol., 1 (1990) 150–154.
Nursten, H. E., Key mechanistic problems posed by the Maillard reaction. In The Maillard Reaction in Food Processing, Human Nutrition and Physiology, ed. P. A. Finot, H. U. Aeschbacher, R. F. Hurrell & R. Liardon. Birkhäuser, Basel, 1990, pp. 145–153.
Hodge, J. E., Origin of flavors in foods: non-enzymatic browning reactions. In Symp. Foods: Chemistry and Physiology of Flavors, ed. H. W. Schultz, E. A. Day & L. M. Libbey. AVI, Westport, Conn., 1967, pp. 465–491.
Mills, F. D., Baker, B. G. & Hodge, J. E., Amadori compounds as nonspecific flavor precursors in processed foods. J. Agric. Food Chem., 17 (1969) 723–727.
Anet, E. F. L. J., Chemistry of non-enzymic browning. II. Some crystalline amino acid-deoxy sugars. Aust. J. Chem., 10 (1957) 193–197.
Baltes, W., Franke, K., Hörtig, W., Otto, R. & Lessig, U., Investigations on model systems of Maillard reactions. In Maillard Reactions in Food, ed. C. Eriksson. Progress in Food and Nutrition Science, Vol. 5 (1–6). Pergamon Press, Oxford, 1981, pp. 137–145.
Heyns, K., Müller, G. & Paulsen, H., Quantitative studies on the reactionsof hexoses with amino acids. Justus Liebigs Ann. Chem., 703 (1967) 202–214.
Hayashi, T., Mase, S. & Namiki, M., Formation of the N,N′-dialkylpyrazine cation radical from glyoxal dialkylimine produced on reaction of a sugar with an amine or amino acid. Agric. Biol. Chem., 49 (1985) 3131–3137.
Hayashi, T., Ohta, Y. & Namiki, M., Electron spin resonance spectral study on the structure of the novel free radical products formed by the reactions of sugars with amino acids or amines. J. Agric. Food Chem., 25 (1977) 1282–1287.
Namiki, M. & Hayashi, T., A new mechanism of the Maillard reaction involving sugar fragmentation and free radical formation. In The Maillard Reaction in Foods and Nutrition, ed. G. R. Waller & M. S. Feather. ACS Symp. Ser. 215, ACS, Washington DC, 1983, pp. 21–46.
Hayashi, T., Mase, S. & Namiki, M., Formation of three-carbon sugar fragment at an early stage of the browning reaction of sugar with amines or amino acids. Agric. Biol. Chem., 50 (1986) 1959–1964.
Hayashi, T. & Namiki, M., Role of sugar fragmentation in an early stage browning of amino-carbonyl reaction of sugar with amino acids. Agric. Biol. Chem., 50 (1986) 1965–1970.
Yano, M., Hayashi, T. & Namiki, M., Formation of free radical products by the reaction of dehydroascorbic acid with amino acid. J. Agric. Food Chem., 24 (1976) 815–819.
Gomyo, T., Haiyan, L., Miura, M., Hayase, F. & Kato, H., Kinetic aspects of the blue pigment formation in a Maillard reaction between D-xylose and glycine. Agric. Biol. Chem., 53 (1989) 949–957.
Yaylayan, V., Jocelyn Pare, J. R., Laing, R. & Sporns, P., Intramolecular nucleophilic substitution reactions of tryptophan and lysine Amadori rearrangement products. In The Maillard Reaction in Food Processing, Human Nutrition and Physiology, ed. P. A. Finot, H. U. Aeschbacher, R. F. Hurrell & R. Liardon. Birkhäuser, Basel, 1990, pp. 115–120.
Anet, E. F. L. J., Formation of furan compounds from sugars. Chem. Ind. (1962) 262.
Beck, J., Ledl, F., Sengl, M. & Severin, T., Formation of acids, lactones and esters through the Maillard reaction. Z. Lebensm. Unters. Forsch., 190 (1990) 212–216.
Ledl, F., Hiebl, J. & Severin, T., Formation of coloured 13-pyranones from hexoses and pentoses. Z. Lebensm. Unters. Forsch., 177 (1983) 353–355.
Kato, H., Chemical studies on amino-carbonyl reaction III. Formation of substituted pyrrole-2-aldehydes by reaction of aldoses with alkylamines. Agric. Biol. Chem. 31 (1967) 1086–1090.
Jurch, G. R. & Tatum, J. H., Degradation of D-glucose with acetic acid and methylamine. Carbohydr. Res., 15 (1970) 233–239.
Pachmayr, O., Ledl, F. & Severin, T., Formation of 1-alky1–3-oxopyridiniumbetaines from sugars. XXI. Investigations relating to the Maillard reaction. Z. Lebensm. Unters. Forsch., 182 (1986) 294–297.
Hayase, F., Nagaraj, R. H., Miyata, S., Njoroge, F. G. & Monnier, V. M., Aging of proteins: immunological detection of a glucose-derived pyrrole formed during Maillard reaction in vivo. J. Biol. Chem., 264 (1989) 3758–3764.
Olsson, K., Pernemalm, P. Å., Popoff, T. & Theander, O., Formation of aromatic compounds from carbohydrates. V. Reaction of D-glucose and methylamine in slightly acidic aqueous solution. Acta Chem. Scand. Ser. B, 31(1977) 469–474.
Shigematsu, H., Kurata, T., Kato, H. & Fujimaki, M., Formation of 2-(5-hydroxymethy1–2-formylpyrrol-1-yl)alkyl acid lactones on roasting alkyl-aamino acid with D-glucose. Agric. Biol. Chem., 35 (1971) 2097–2105.
Olsson, K., Pernemalm, P. Å. & Theander, O., Formation of aromatic compounds from carbohydrates. VII. Reaction of D-glucose and glycine in slightly acidic aqueous solution. Acta Chem. Scand. Ser. B, 32 (1978) 249–256.
Olsson, K., Pernemalm, P. Å. & Theander, O., Reaction products and mechanism in some simple model systems. In Maillard Reactions in Food, ed. C. Eriksson. Progress in Food and Nutrition Science, Vol. 5 (1–6). Pergamon Press, Oxford. 1981, 47–55.
Njoroge, F. G., Sayre, L. M. & Monnier, V. M., Detection of D-glucose-derived pyrrole compounds during Maillard reaction under physiological conditions. Carbohydr. Res., 167 (1987) 211–220.
Miller, R., Olsson, K. & Pernemalm, P. A., Formation of aromatic compounds from carbohydrates. IX. Reaction of D-glucose and L-lysine in slightly acidic, aqueous solution. Acta Chem. Scand. Ser. B, 38 (1984) 689–694.
Tressl, R., Helak, B. & Rewicki, D., Malzoxazin, eine tricyclische Verbindung aus Gerstenmalz. Helv. Chim. Acta., 65 (1982) 483–489.
Ledl, F., Krönig, U., Severin, T. & Lotter, H., Investigations relating to Maillard-reaction XVIII. Isolation of N-containing coloured products. Z. Lebensm. Unters. Forsch., 177 (1983) 267–270.
Njoroge, F. G., Fernandes, A. A. & Monnier, V. M., 3-(D-erythro-Trihydroxypropy1)-1-neopentylpyrrolecarboxaldehyde, a novel nonenzymatic browning product of glucose. J. Carbohydr. Chem., 6 (1987) 553–568.
Farmar, J. G., Ulrich, P. C. & Cerami, A., Novel pyrroles from sulfite-inhibited Maillard reactions: Insight into the mechanism of inhibition. J. Org. Chem., 53 (1988) 2346–2349.
Ledl, F., Fritsch, G., Hiebl, J., Pachmayr, O. & Severin, T., Degradation of Maillard products. In Amino-Carbonyl Reactions in Food and Biological Systems, ed. M. Fujimaki, M. Namiki &. H. Kato. Developments in Food Science, Vol. 13. Elsevier, Amsterdam, 1986, pp. 173–182.
Beck, J., Ledl, F. & Severin, T., Formation of 1-deoxy-D-erythro-2,3-hexodiulose from Amadori compounds. Carbohydr. Res., 117 (1988) 240–243.
Hiebl, J., Ledl, F. & Severin, T., Isolation of 4-hydroxy-2-(hydroxymethyl)-5-methy1–3(2H)-furanone from sugar amino acid reaction mixtures. J. Agric. Food Chem., 35 (1987) 990–993.
Hodge, J. E., Fisher, B. E. & Nelson, E. C., Dicarbonyls, reductones and heterocyclics produced by reactions of reducing sugars with secondary amine salts. Proc. Am. Soc. Brew. Chem. (1963) 84–92.
Ledl, F., Formation of aminoreductones from disaccharides. Z. Lebensm. Unters. Forsch., 179 (1984) 381–384.
Ledl, F. & Fritsch, G., Formation of pyrrolinone reductones by heating hexoses with amino acids. Z. Lebensm. Unters. Forsch., 178 (1984) 41–44.
Mills, F. D., Baker, B. G. & Hodge, J. E., Thermal degradation of 1-deoxy1-piperidino-D-fructose. Carbohydr. Res., 15 (1970) 205–213.
Ledl, F. & Severin, T., Formation of aminoreductones from glucose and primary amines. XIV. Investigations relating to Maillard reaction. Z. Lebensm. Unters. Forsch., 169 (1979) 173–175.
Simon, H., Heubach, G., Bitterlich, W. & Gleinig, H., Reaction of bromodiacetyl and of alicyclic 1-chloro-2,3-diones with primary and secondary amines to reductones and some properties of the products. Chem. Ber., 98 (1965) 3692–3702.
Ledl, F., Ellrich, G. & Klostermeyer, H., Proof and identification of a new Maillard compound in heated milk. Z. Lebensm. Unters. Forsch., 182 (1986) 19–24.
Matsuura, H., Hirao, Y., Yoshida, Y., Kumihiro, K., Fuwa, T., Kasai, R. & Tanaka, O., Study of red ginseng: new glucosides and a note on the occurrence of maltol. Chem. Pharm. Bull., 32 (1984) 4674–4677.
Hodge, J. E. & Nelson, E. C., Preparation and properties of galactosylisomaltol and isomaltol. Cereal Chem., 38 (1961) 207–221.
Patton, S., The formation of maltol in certain carbohydrate-glycine systems. J. Biol. Chem., 184 (1950) 131–134.
Peer H. G., van den Ouweland, G. A. M. & de Groot, C. N., The reaction of aldopentoses and secondary amine salts, a convenient method of preparing 4-hydroxy-5-methyl-2,3-dihydrofuran-3-one. Red. Tray. Chim. Pays-Bas, 87 (1968) 1011–1020.
Severin, T. & Loidl, A., Formation of pyridone derivatives from maltose and lactose. XII. Investigations of the Maillard reaction. Z. Lebensm. Unters. Forsch., 161 (1976) 119–124.
Ledl, F., Osiander, H., Pachmayr, O. & Severin, T., Formation of maltosine, a product of the Maillard reaction with a pyridone structure. Z. Lebensm. Unters. Forsch., 188 (1989) 207–211.
Huber, B. & Ledl, F., Formation of 1-amino-1,4-dideoxy-2,3-hexodiuloses and 2-aminoacetylfurans in the Maillard reaction. Carbohydr. Res., 204 (1990) 215–220.
Huber, B., Ledl, F., Severin, T., Stangl, A. & Pfleiderer, G., Formation of 2-(2-furoy1)-4(5)-(2-fury1)-1H-imidazole in the Maillard reaction. Carbohydr. Res., 182 (1988) 301–306.
Njoroge, F. G., Fernandes, A. A. & Monnier, V. M., Mechanism of formation of the putative advanced glycosylation end product and protein crosslink 2-(2-furoy1)-4,5-(2-furany1)-1H-imidazole. J. Biol. Chem., 263 (1988) 10646–10652.
Estendorfer, S., Ledl, F. & Severin, T., Formation of an aminoreductone from glucose. Angew. Chem. Int. Ed. Engl., 29 (1990) 536–537.
Beck, J., Ledl, F., Sengl, M. & Severin, T., Formation of glucosyl deoxyosones from Amadori compounds of maltose. Z. Lebensm. Unters. Forsch., 188 (1989) 118–121.
Ahmed, M. U., Thorpe, S. R. & Baynes, J. W., Identification of Nϵ-carboxymethyllysine as a degradation product of fructoselysine in glycated protein. J. Biol. Chem., 261 (1986) 4889–4894.
Hayashi, T. & Namiki, M., Role of sugar fragmentation in the Maillard reaction. In Amino-Carbonyl Reactions in Food and Biological Systems, ed. M. Fujimaki, M. Namiki & H. Kato. Developments in Food Science, Vol. 13. Elsevier, Amsterdam, 1986, pp. 29–38.
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., 25 (1977) 641–644.
Nyhammar, T., Olsson, K. & Pernemalm, P. A., In The Maillard Reaction in Foods and Nutrition, ed. G. R. Waller & M. S. Feather. ACS Symp. Ser. 215, ACS, Washington D.C., 1983, pp. 71–82.
Nyhammar, T., Olsson, K. & Pernemalm, P. A., On the formation of 2-acylpyrroles and 3-pyridinols in the Maillard reaction through Strecker degradation. Acta Chem. Scand. Ser. B, 37 (1983) 879–889.
Ames, J. M. & Nursten, H. E., Recent advances in the chemistry of coloured compounds formed during the Maillard reaction. In Trends in Food Science, ed. W. S. Lien & C. W. Foo. Singapore Institute of Food Science and Technology, 1989, pp. 8–14.
Motai, H., Viscosity of melanoidins formed by oxidative browning. Validity of the equation for a relationship between color intensity and molecular weight of melanoidin. Agric. Biol. Chem., 40 (1976) 1–7.
Kato, H. & Tsuchida, H., Estimation of melanoidin structure by pyrolysis and oxidation. In Maillard Reactions in Food, ed. C. Eriksson. Progress in Food and Nutrition Science, Vol. 5 (1–6). Pergamon Press, Oxford, 1981, pp. 147–156.
Barbetti, P. & Chiappini, I., Fractionation and spectroscopic characterization of melanoidic pigments from a glucose-glycine non-enzymic browning system. Ann. Chim. (Rome), 66 (1976) 293–304.
Feather, M. S., Some aspects of the chemistry of non-enzymatic browning (the Maillard reaction). In Chemical Changes in Food During Processing, ed. T. Richardson & J. W. Finley. AVI, Westport, 1985, pp. 289–303.
Feather, M. S. & Nelson, D., Maillard polymers derived from D-glucose, D-fructose, 5-(hydroxymethyl)-2-furaldehyde, and glycine and methionine. J. Agric. Food Chem., 32 (1984) 1428–1432.
Benzing-Purdie, L. M. & Ratcliffe, C. I., A Study of the Maillard reaction by 13C and 15N CP-MAS NMR: Influence of time, temperature and reactants on major products. In Amino-Carbonyl Reactions in Food and Biological Systems, ed. M. Fujimaki, M. Namiki & H. Kato. Developments in Food Science, Vol. 13. Elsevier, Amsterdam, 1986, pp. 193–205.
Feather, M. S. & Huang, R. -D., Some studies on a Maillard polymer derived from L-alanine and D-glucose. In Amino-Carbonyl Reactions in Food and Biological Systems, ed. M. Fujimaki, M. Namiki & H. Kato. Developments in Food Science, Vol 13. Elsevier, Amsterdam, 1986, pp. 183–192.
Kato, H., Kim, S. B. & Hayase, F., Estimation of the partial chemical structures of melanoidins by oxidative degradation and 13C CP-MAS NMR. In Amino-Carbonyl Reactions in Food and Biological Systems, ed. M. Fujimaki, M. Namiki & H. Kato. Developments in Food Science, Vol 13. Elsevier, Amsterdam, 1986, pp. 215–223.
Hayase, F., Kim, S. B. & Kato, H., Analysis of the chemical structures of melanoidins by 13C NMR, 13C and 15N CP-MAS NMR spectrometry. Agric. Biol. Chem., 50 (1986) 1951–1957.
Benzing-Purdie, L. M., Ripmeester, J. A. & Ratcliffe, C. I., Effects of temperature on Maillard reaction products. J. Agric. Food Chem., 33 (1985) 31–33.
Baltes, W., Application of pyrolytic methods in food chemistry. J. Anal. Appl. Pyrol., 8 (1985) 533–545.
Wu, C. H., Russell, G. F. & Powrie, W. D., Paramagnetic behaviour of model system melanoidins. In Amino-Carbonyl Reactions in Food and Biological Systems, ed. M. Fujimaki, M. Namiki & H. Kato. Developments in Food Science, Vol 13. Elsevier, Amsterdam, 1986, pp. 135–144.
Clark, A. V. & Tannenbaum, S. R., Isolation and characterisation of pigments from protein-carbonyl browning systems. Isolation, purification and properties. J. Agric. Food Chem., 18 (1970) 891–894.
Clark, A. V. & Tannenbaum, S. R., Studies on limit-peptide pigments from glucose-casein browning systems using radioactive glucose. J. Agric. Food Chem., 21 (1973) 40–43.
Clark, A. V. & Tannenbaum, S. R., Isolation and characterization of pigments from protein-carbonyl browning systems. Models for two insulinglucose pigments. J. Agric. Food Chem., 22 (1974) 1089–1093.
Henry, K. M., Kon, S. K., Lea, C. H. & White, J. C. D., Deterioration on storage of dried skim milk. J. Dairy Res., 15 (1948) 293–356.
Lea, C. H. & Hannan, R. S., Studies of the reaction between proteins and reducing sugars in the ‘dry’ state. II. Further observations on the formation of the casein-glucose complex. Biochim. Biophys. Acta., 4 (1950) 518–531.
Lea, C. H. & Hannan, R. S., Studies of the reaction between proteins and reducing sugars in the ‘dry’ state. III. Nature of the protein groups reacting. Biochim. Biophys. Acta., 5 (1950) 433–454.
Ludwig, E., Die Verfolgung der Maillard-Reaktion zwischen β-Lactoglobulin und Lactose mittels Isoelektrofocussierung in Polyacrylamidgelen. Nahrung, 18 (1974) 615–620.
Finot, P. A., Deutsch, R. & Bujard, E., The extent of the Maillard reaction during the processing of milk. In Maillard Reactions in Food, ed. C. Eriksson. Progress in Food and Nutrition Science, Vol. 5 (1–6). Pergamon Press, Oxford, 1981, pp. 345–355.
Hurrell, R. F. & Finot, P. A., Food processing and storage as a determinant of protein and amino acid availability. In Nutritional Adequacy, Nutrient Availability and Needs, ed. J. Mauron. Experientia Basel Supplementum. Birkhäuser, Basel, 1983, pp. 135–156.
Erbersdobler, H. F., Protein reactions during food processing and storage -their relevance to human nutrition. In Nutritional Impact of Food Processing, ed. J. C. Somogyi & H. R. Muller. Bibl. Nutr. Dieta. No. 43. Karger, Basel, 1989, pp. 140–155.
Frangne, R. & Adrian, J., The Maillard reaction. VI. Reactivity of various purified proteins. Ann. Nutr. Aliment., 26 (1972) 97–106.
Adrian, J. & Frangne, R., Le comportement des proteolysats au cours de la reaction de Maillard. Ind. Aliment. Agric., 26 (1976) 23–28.
Hurrell, R. F. & Carpenter, K. J., Nutritional significance of cross-link formation during food processing. In Protein Crosslinking. Nutritional and Medical Consequences, ed. M. Friedman. Advances in Experimental Medicine and Biology, Vol. 86B. Plenum Press, New York, 1977, pp. 225–238.
Möller, A. B., Andrews, A. T. & Cheeseman, G. C., Chemical changes in ultra-heat-treated milk during storage. II. Lactuloselysine and fructoselysine formation by the Maillard reaction. J. Dairy Res., 44 (1977) 267–275.
Hurrell, R. F., Influence of the Maillard reaction on the nutritional value of foods. In The Maillard Reaction in Food Processing, Human Nutrition and Physiology, ed. P. A. Finot, H. U. Aeschbacher, R. F. Hurrell & R. Liardon. Birkhäuser, Basel, 1990, pp. 245–258.
Labuza, T. P. & Saltmarch, M., The nonenzymatic browning reaction as affected by water in foods. In Water Activity: Influences on Food Quality, ed. L. B. Rockland & G. F. Stewart. Academic Press, New York, 1981, pp. 605–650.
Ludwig, E., Untersuchungen zur Maillard-Reaktion zwischen β-Lactoglobulin und Lactose. 3. Mitt. Der Einfluß intermolekularer Disulfidbrücken auf die Blockierung von Lysin. Nahrung, 23 (1979) 707–714.
Nielsen, H. K., De Wecke, D., Finot, P. A., Liardon, R. & Hurrell, R. F., Stability of tryptophan during food processing and storage. 1. Comparative losses of tryptophan, lysine and methionine in different model systems. Br. J. Nutr., 53 (1985) 281–292.
Nielsen, H. K., Klein, A. & Hurrell, R. F., Stability of tryptophan during food processing and storage. 2. A comparison of the methods used for the measurement of tryptophan losses in processed foods. Br. J. Nutr., 53 (1985) 293–300.
Möller, A. B., Andrews, A. T. & Cheeseman, G. C., Chemical changes in ultra-heat-treated milk during storage. III. Methods for the estimation of lysine and sugar-lysine derivatives formed by the Maillard reaction. J. Dairy Res., 44 (1977) 277–281.
Hurrell, R. F. & Carpenter, K. J., The estimation of available lysine in foodstuffs after Maillard reactions. In Maillard Reactions in Food, ed. C. Eriksson. Progress in Food and Nutrition Science, Vol. 5 (1–6). Pergamon Press, Oxford, 1981, pp. 159–176.
Carpenter, K. J. & Booth, V. H. Damage to lysine in food processing: its measurement and its significance. Nutr. Abstr. Rev., 43 (1973) 423–451.
Erbersdobler, H., Amino acid availability. In Protein Metabolism and Nutrition, ed. D. J. A. Cole, K. N. Boorman, P. J. Buttery, D. Lewis, R. J. Neale & H. Swan. Butterworths, London, 1976, pp. 139–158.
Tanaka, M., Lee, T. -C. & Chichester, C. O., Effect of browning on chemical properties of egg albumin. Agric. Biol. Chem., 39 (1975) 863–866.
Kato, H., Matsumura, M. & Hayase, F., Chemical changes in casein heated with and without D-glucose in the powdered state or in an aqueous solution. Food Chem., 7 (1981) 159–168.
Holt, C., Muir, D. D. & Sweetsur, A. W. M., The heat stability of milk and concentrated milk containing added aldehydes and sugars. J. Dairy Res., 45 (1978) 47–52.
Nelson, V., Effects of formaldehyde and copper salts on the heat stability of evaporated milk. J. Dairy Sci., 37 (1954) 825–829.
Tybor, P. T., Dill, C. W. & Landmann, W. A., Effect of decolorization and lactose incorporation on the emulsification capacity of spray-dried blood protein concentrates. J. Food Sci., 38 (1973) 4–6.
Morales, M., Dill, C. W. & Landmann, W. A. Effect of Maillard condensation with D-glucose on the heat stability of bovine serum albumin. J. Food Sci., 41 (1976) 234–236.
Back, J. F., Oakenfull, D. and Smith, M. B., Increased thermal stability of proteins in the presence of sugars and polyols. Biochemistry, 18 (1979) 5191–5196.
Lea, C. H., The reaction between milk protein and reducing sugar in the dry state. J. Dairy Res., 15 (1948) 369–376.
Lea, C. H., Hannan, R. S. & Rhodes, D. N. Studies of the reaction between proteins and reducing sugars in the dry state. IV. Decomposition of the amino-sugar complex and the reaction of acetylated casein with glucose. Biochim. Biophys. Acta., 7 (1951) 366–377.
Mohammad, A., Fraenkel-Conrat, H. & Olcott, H. S., The “browning” reaction of proteins with glucose. Arch. Biochim. Biophys., 24 (1949) 157–178.
Shalabi, S. I. & Fox, P. F., Heat stability of milk: synergistic action of urea and carbonyl compounds. J. Dairy Res., 49 (1982) 197–207.
Shalabi, S. I. & Fox, P. F., Heat stability of milk: influence of modification of lysine and arginine on the heat stability-pH profile. J. Dairy Res., 49 (1982) 607–617.
Shalabi, S. I. & Fox, P. F., Effect of diacetyl on the heat stability of concentrated milks. J. Food Technol., 17 (1982) 753–760.
Kato, Y., Watanabe, K. & Sato, Y., Effect of the Maillard reaction on the attributes of egg white proteins. Agric. Biol. Chem., 42 (1978) 2233–2237.
Watanabe, K., Sato, Y. & Kato, Y., Chemical and conformational changes of ovalbumin due to the Maillard reaction. J. Food Process. Preserv., 3 (1980) 263–274.
Kato, Y., Watanabe, K. & Sato, Y., Effect of Maillard reaction on some physical properties of albumin. J. Food Sci., 46 (1981) 1835–1839.
Kato, Y., Watanabe, K. & Sato, Y., Effect of some metals on the Maillard reaction of ovalbumin. J. Agric. Food Chem., 29 (1981) 540–543.
Kato, Y., Watanabe, K. & Sato, Y., Conformational stability of ovalbumin reacted with glucose in a Maillard reaction. Agric. Biol. Chem., 47 (1983) 1925–1926.
Wu, H., Govindarajan, S., Smith, T., Rosen, J. D. & Ho, C.-T., Glucose— lysozyme reactions in a restricted water environment. In The Maillard Reaction in Food Processing, Human Nutrition and Physiology, ed. P. A. Finot, H. U. Aeschbacher, R. F. Hurrell & R. Liardon. Birkhäuser, Basel, 1990, pp. 85–90.
Hull, C. J., Studies on the glycation and Maillard reactions of protein. Ph.D. Dissertation, University of South Carolina, Columbia, South Carolina, 1985.
Baynes, J. W., Ahmed, M. U., Fisher, C. I., Hull, C. J., Lehman, T. A., Watkins, N. G. & Thorpe, S. R., Studies on glycation of proteins and Maillard reactions of glycated proteins under physiological conditions. In Amino-Carbonyl Reactions in Food and Biological Systems, ed. M. Fujimaki, M. Namiki & H. Kato. Developments in Food Science, Vol. 13. Elsevier, Amsterdam, 1986, pp. 421–431.
Cho, R. K., Okitani, A. & Kato, H., Chemical properties and polymerizing ability of the lysozyme monomer isolated after storage with glucose. Agric. Biol. Chem., 48 (1984) 3081–3089.
Cho, R. K., Okitani, A. & Kato, H., Polymerisation of proteins and impairment of their arginine residues due to intermediate compounds in the Maillard reaction. In Amino-Carbonyl Reactions in Food and Biological Systems, ed. M. Fujimaki, M. Namiki & H. Kato. Developments in Food Science, Vol. 13. Elsevier, Amsterdam, 1986, pp. 439–448.
Eble, A. S., Thorpe, S. R. & Baynes, J. W., Nonenzymatic glucosylation and glucose-dependent cross-linking of protein. J. Biol. Chem., 258 (1983) 9406–9412.
Okitani, A., Cho, R. K. & Kato, H., Polymerization of lysozyme and impairment of its amino acid residues caused by reaction with glucose. Agric. Biol. Chem., 48 (1984) 1801–1808.
Cho, R. K., Okitani, A. & Kato, H., Polymerization of acetylated lysozyme and impairment of their amino acid residues due to a-dicarbonyl and a-hydroxycarbonyl compounds. Agric. Biol. Chem., 50 (1986) 1373–1380.
Kato, H., Cho, R. K., Okitani, A. & Hayase, F., Responsibility of 3-deoxyglucosone for the glucose-induced polymerization of proteins. Agric. Biol. Chem., 51 (1987) 683–689.
Igaki, N., Saai, M., Hata, F., Yamada, H., Oimomi, M., Baba, S. & Kato, H., The role of 3-deoxyglucosone in the Maillard reaction. In The Maillard Reaction in Food Processing, Human Nutrition and Physiology, ed. P. A. Finot, H. U. Aeschbacher, R. F. Hurrell & R. Liardon. Birkhäuser, Basel, 1990, pp. 103–108.
Shin, D. B., Hayase, F. & Kato, H., Polymerization of proteins caused by reaction with sugars and the formation of 3—deoxyglucosone under physiological conditions. Agric. Biol. Chem., 52 (1988) 1451–1458.
Kato, H., Yamamoto, M. & Fujimaki, M., Mechanisms of browning degradation of D-fructose in special comparison with D-glucose—glycine reaction. Agric. Biol. Chem., 33 (1969) 939–948.
Sakai, M., Igaki, N., Nakamichi, T., Ohara, T., Masuta, S., Maeda, Y., Hata, F., Oimomi, M. & Baba, S., Acceleration of fructose-mediated collagen glycation. In The Maillard Reaction in Food Processing, Human Nutrition and Physiology, ed. P. A. Finot, H. U. Aeschbacher, R. F. Hurrell & R. Liardon. Birkhäuser, Basel, 1990, pp. 481–486.
Möller, A. B., Chemical changes in ultra heat treated milk during storage. In Maillard Reactions in Food, ed. C. Eriksson. Progress in Food and Nutrition Science, Vol. 5 (1–6). Pergamon Press, Oxford, 1981, pp. 357–368.
Dworschak, E., Nonenzymic browning and its effect on protein nutrition. CRC Crit. Rev. Food Sci. Nutr., 13 (1980) 1–40.
Feeney, R. E., Overview on the chemical deteriorative changes of proteins and their consequences. In Chemical Deterioration of Proteins, ed. J. R. Whitaker & M. Fujimaki. ACS Symp. Ser. 123, ACS, Washington D.C., 1980, pp. 1–47.
Matsumoto, J. J., Chemical deterioration of muscle proteins during frozen storage. In Chemical Deterioration of Proteins, ed. J. R. Whitaker & M. Fujimaki. ACS Symp. Ser. 123, ACS, Washington D.C., 1980, pp. 95–124.
Spark, A. A., Role of amino acids in non-enzymic browning. J. Sci. Food Agric., 20 (1969) 308–316.
Ashoor, S. H. & Zent, J. B., Maillard browning of common amino acids and sugars. J. Food Sci., 49 (1984) 1206–1207.
Lewis, V. M. & Lea, C. H., A note on the relative rates of reaction of several reducing sugars and sugar derivatives with casein. Biochim. Biophys. Acta., 4 (1950) 532–534.
Rao, N. M. & Rao, M. M. Effect of non-enzymatic browning on the nutritive value of casein-sugar complexes. J. Food Sci. Tech. (Mysore), 9 (1972) 66–68.
Kato, Y., Matsuda, T., Kato, N., Watanabe, K. & Nakamura, R., Browning and insolubilisation of ovalbumin by the Maillard reaction with some aldohexoses. J. Agric. Food Chem., 34 (1986) 351–355.
Kato, Y., Matsuda, T., Kato, N., Watanabe, K. & Nakamura, R., Maillard reaction of some aldohexoses with ovalbumin. In Amino-Carbonyl Reactions in Food and Biological Systems, ed. M. Fujimaki, M. Namiki & H. Kato. Developments in Food Science, Vol. 13. Elsevier, Amsterdam, 1986, pp. 115–124.
Kato, Y., Matsuda, T., Kato, N. & Nakamura, R., Browning and protein polymerisation induced by amino-carbonyl reaction of ovalbumin with glucose and lactose. J. Agric. Food Chem., 36 (1988) 806–809.
Bunn, H. F. & Higgins, P. J., Reaction of monosaccharides with protein: possible evolutionary significance. Science, 213 (1981) 222–224.
Hayward, L. D. & Angyal, S. J., A symmetry rule for the circular dichroism of reducing sugars, and the proportion of carbonyl forms in aqueous solutions thereof. Carbohydr. Res., 53 (1977) 13–20.
Kato, Y., Matsuda, T., Kato, N. & Nakamura, R., Maillard reaction in sugar-protein systems. In The Maillard Reaction in Food Processing, Human Nutrition and Physiology, ed. P. A. Finot, H. U. Aeschbacher, R. F. Hurrell & R. Liardon. Birkhäuser, Basel, 1990, pp. 97–102.
O’Brien, J. & Morrissey, P. A., Nutritional and toxicological aspects of the Maillard reaction in foods. CRC. Crit. Rev. Food Sci. Nutr., 28 (1989) 211–248.
Finot, P. A., Hurrell, R. F., Deutsch, R. & Klein, A., 1979. Unpublished data. In Finot, P. A., Deutsch, R. & Bujard, E. The extent of the Maillard reaction during the processing of milk. In Maillard Reactions in Food, ed. C. Eriksson. Progress in Food and Nutrition Science, Vol. 5 (1–6). Pergamon Press, Oxford, 1981, pp. 345–355.
Knipfel, J. E., Nitrogen and energy availabilities in foods and feeds subjected to heating. In Maillard Reactions in Food, ed. C. Eriksson. Progress in Food and Nutrition Science, Vol. 5 (1–6). Pergamon Press, Oxford, 1981, pp. 177–192.
Erbersdobler, H. F., The biological significance of carbohydrate-lysine crosslinking during heat treatment of food proteins. In Protein Crosslinking: Nutritional and Medical Consequences, ed. M. Freidman. Plenum Press, New York, 1977, pp. 367–378.
Hansen, L. P. & Millington, R. J., Blockage of protein enzymatic digestion (carboxypeptidase-B) by heat-induced sugar-lysine reactions. J. Food Sci., 44 (1979) 1173–1177.
Ford, J. E., Hurrell, R. F. & Finot, P. A., Storage of milk powders under adverse conditions. 2. Influence on the content of water-soluble vitamins. Br. J. Nutr., 49 (1983) 355–364.
Nursten, H. E., Aroma compounds from the Maillard reaction. In Developments in Food Flavour, ed. G. G. Birch & M. G. Lindley. Elsevier Applied Science, London, 1986, pp. 173–190.
Parliment, T. H., McGorrin, R. J. & Ho, C.-T., ed. Thermal Generation of Aromas. ACS Symp. Ser. 409, ACS, Washington D.C., 1989.
Tressl, R., Processed flavors-scope and limitations. In Flavour Science and Technology, ed. Y. Bessière & A. F. Thomas. Wiley, Chichester, 1990, pp. 87–104.
Hurrell, R. F., Maillard reaction in flavour. In Food Flavours Part A. Introduction, ed. I. D. Morton & A. J. MacLeod. Developments in Food Science, Vol. 3A. Elsevier, New York, 1982, pp. 399–437.
Ferretti, A. & Flanagan, V. P., The lactose-casein (Maillard) browning system: volatile components. J. Agric. Food Chem., 19 (1971) 245–249.
Ferretti, A., Flanagan, V. P. & Ruth, J. M., Non-enzymic browning in a lactose-casein model system. J. Agric. Food Chem., 18 (1970) 13–18.
Berry, S. K. & Gramshaw, J. W., Influence of starch plus gluten on the nonenzymatic browning reaction of the glucose-glutamic acid system. J. Agric. Food Chem., 36 (1988) 1265–1267.
Tressl, R., Helak, B., Kersten, E. & Rewicki, D., Related ring enlargement reactions of proline, azetidinic acid, arginine and lysine with reducing sugars. In The Maillard Reaction in Food Processing, Human Nutrition and Physiology, ed. P. A. Finot, H. U. Aeschbacher, R. F. Hurrell & R. Liardon. Birkhäuser, Basel, 1990, pp. 121–132.
Apriyantono, A. & Ames, J. M., Volatile compounds produced on heating lysine with xylose. In Flavour Science and Technology, ed. Y. Bessière & A. F. Thomas. Wiley, Chichester, 1990, pp. 117–120.
Pabst, H. M. E., Ledl, F. & Belitz, H.-D., Bitter compounds obtained by heating proline and sucrose. Z. Lebensm. Unters. Forsch., 178 (1984) 356–360.
Schnickels, R. A., Warmbier, H. C. & Labuza, T. P., Effect of protein substitution on nonenzymatic browning in an intermediate moisture food system. J. Agric. Food Chem., 24 (1976) 901–903.
Nursten, H. E. and O’Reilly, R., The complexity of the Maillard reaction as shown by a xylose-glycine model system. In Amino-Carbonyl Reactions in Food and Biological Systems, ed. M. Fujimaki, M. Namiki and H. Kato. Developments in Food Science, Vol. 13. Elsevier, Amsterdam, 1986, pp. 15–28.
Ledl, F. & Severin, T., Formation of coloured compounds from hexoses. XVI. Investigations relating to the Maillard reaction. Z. Lebensm. Unters. Forsch., 175 (1982) 262–265.
Severin, T. & Krönig, U., Maillard reaction IV. Structure of a colored product from pentoses. Chem. Mikrobiol. Technol. Lebensm., 1 1972, 156–157.
Nursten, H. E. & O’Reilly, R., Coloured compounds formed by the interaction of glycine with xylose. In The Maillard Reaction in Foods and Nutrition, ed. G. R. Waller &. M. S. Feather. ACS Symp. Ser. 215, ACS. Washington D.C., 1983, pp. 103–121.
Ledl, F. & Severin, T., Browning reactions of pentoses with amines. Investigation of the Maillard reaction XIII. Z. Lebensm. Unters. Forsch., 167 (1978) 410–413.
Nursten, H. E. & O’Reilly, R., Coloured compounds formed by the interaction of glycine and xylose. Food Chem., 20 (1986) 45–60.
Banks, S. B., Ames, J. M. & Nursten, H. E., Isolation and characterisation of 4-hydroxy-2-hydroxymethy1–3-(2′-pyrroly1)-2-cyclopenten-1-one from a xylose/lysine reaction mixture. Chem. Ind., (1988) 433–434.
Kurata, T., Fujimaki, M. & Sakurai, Y., Red pigment produced by the reaction of dehydro-L-ascorbic acid with a-amino acid. Agric. Biol. Chem., 37 (1973) 1471–1477.
Sakurai, H. & Ishii, K., Structural analysis of ninhydrin-positive substance produced by the reaction of dehydroascorbic acid with glycylleucine. Bull. Coll. Agric. Vet. Med. Nihon Univ., 45 (1988) 50–59.
Lingnert, H. & Hall, G., Formation of antioxidative Maillard reaction products during food processing. In Amino-Carbonyl Reactions in Food and Biological Systems, ed. M. Fujimaki, M. Namiki & H. Kato. Developments in Food Science, Vol. 13. Elsevier, Amsterdam, 1986, pp. 273–279.
Lingnert, H., Development of the Maillard reaction during food processing. In The Maillard Reaction in Food Processing, Human Nutrition and Physiology, ed. P. A. Finot, H. U. Aeschbacher, R. F. Hurrell & R. Liardon. Birkhäuser, Basel, 1990, pp. 171–185.
Chuyen, N. V., Utsunomiya, N., Hidaka, A. & Kato, H., Antioxidative effect of Maillard reaction products in vivo. In The Maillard Reaction in Food Processing, Human Nutrition and Physiology, ed. P. A. Finot, H. U. Aeschbacher, R. F. Hurrell & R. Liardon. Birkhäuser, Basel, 1990, pp. 285–290.
Aeschbacher, H. U., Anticarcinogenic effect of browning reaction products. In The Maillard Reaction in Food Processing, Human Nutrition and Physiology, ed. P. A. Finot, H. U. Aeschbacher, R. F. Hurrell & R. Liardon. Birkhäuser, Basel, 1990, pp. 335–348.
Sugimura, T., Takayama, S., Ohgaki, H., Wakabayashi, K. & Nagao, M., Mutagens and carcinogens formed by cooking meat and fish: heterocyclic amines. In The Maillard Reaction in Food Processing, Human Nutrition and Physiology, ed. P. A. Finot, H. U. Aeschbacher, R. F. Hurrell & R. Liardon. Birkhäuser, Basel, 1990, pp. 323–334.
Nyhammar, T., Grivas, S., Olsson, K. & Jägerstad, M., Isolation and identification of beef mutagens (IQ compounds) from heated model systems of creatinine, fructose and glycine or alanine. In Amino-Carbonyl Reactions in Food and Biological Systems, ed. M. Fujimaki, M. Namiki & H. Kato. Developments in Food Science, Vol. 13. Elsevier, Amsterdam, 1986, pp. 323–327.
Jägerstad, M., Laser Reutersward, A., Olsson, R., Grivas, S., Nyhammar, T., Olsson, K. & Dahlqvist, A., Creatin(in)e and Maillard reaction products as precursors of mutagenic compounds: effects of various amino acids. Food Chem., 12 (1983) 255–264.
Wakabayashi, K., Takahashi, M., Nagao, M., Sato, S., Kinae, N., Tomita, I. & Sugimura, T. Quantification of mutagenic and carcinogenic heterocyclic amines in cooked foods. In Amino-Carbonyl Reactions in Food and Biological Systems, ed. M. Fujimaki, M. Namiki & H. Kato. Developments in Food Science, Vol. 13. Elsevier, Amsterdam, 1986, pp. 363–371.
Jägerstad, M., Laser Reutersward, A., Oste, R., Dahlqvist, A., Grivas, S., Olsson, K. & Nyhammar, T. Creatinine and Maillard reaction products as precursors of mutagenic compounds formed in fried beef. In The Maillard Reaction in Foods and Nutrition, ed. G. R. Waller & M. S. Feather. ACS Symp. Ser. 215, American Chemical Society, Washington D.C., 1983, pp. 507–519.
Monnier, V. M., Sell, D. R., Miyata, S. & Nagaraj, R. H., The Maillard reaction as a basis for a theory of aging. In The Maillard Reaction in Food Processing, Human Nutrition and Physiology. ed. P. A. Finot, H. U. Aeschbacher, R. F. Hurrell & R. Liardon. Birkhäuser, Basel, 1990, pp. 393–414.
Sell, D. R. & Monnier, V. M., Structure elucidation of a senescence crosslink from human extracellular matrix. J. Biol. Chem., 264 (1989) 21597– 21602.
O’Brien, J. M. & Morrissey, P. A., The Maillard reaction in milk products. In Heat-Induced Changes in Milk, ed. P. F. Fox. Bulletin of the IDF, No. 238, 1989, 53–61.
Saltmarch, M. & Labuza, T. P., Nonenzymatic browning via the Maillard reaction in foods. In Proceedings of a Conference on Nonenzymatic Glycosylation and Browning Reactions: Their Relevance to Diabetes Mellitus, ed. C. M. Peterson. Diabetes, Vol. 31, Suppl. 3, Part 2 of 2, 1982, pp. 29–35.
Labuza, T. P. & Schmidl, M. K., Advances in the control of browning reactions in foods. In Role of Chemistry in the Quality of Processed Food, ed. O. R. Fennema, W.-H. Chang & C.-Y. Lii. Food & Nutr. Press Inc., Westport, Conn., 1986, pp. 65–95.
Eichner, K. & Ciner-Doruk, M., Formation and decomposition of browning intermediates and visible sugar-amine browning reactions. In Water Activity: Influences of Food Quality, ed. L. B. Rockland & G. F. Stewart. Academic Press, New York, 1981, pp. 567–603.
Saltmarch, M., Vagnini-Ferrari, M. & Labuza, T. P. Theoretical basis and application of kinetics to browning in spray-dried whey food systems. In Maillard Reactions in Food, ed. C. Eriksson. Progress in Food and Nutrition Science, Vol. 5 (1–6). Pergamon Press, Oxford, 1981, pp. 331–344.
McWeeny, D. J., Sulfur dioxide and the Maillard reaction in food. In Maillard Reactions in Food, ed. C. Eriksson. Progress in Food and Nutrition Science. Pergamon Press, Oxford, Vol. 5 (1–6) (1981) pp. 395–404.
Shu, C.-K. & Ho, C.-T. In Thermal Generations of Aromas, ed. T. H. Parliment, R. J. McGorrin & C.-T. Ho. ACS Symp. Ser. 409. American Chemical Society, Washington D.C., 1989, pp. 229–241.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1992 Springer Science+Business Media Dordrecht
About this chapter
Cite this chapter
Ames, J.M. (1992). The Maillard Reaction. In: Hudson, B.J.F. (eds) Biochemistry of Food Proteins. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-9895-0_4
Download citation
DOI: https://doi.org/10.1007/978-1-4684-9895-0_4
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4684-9897-4
Online ISBN: 978-1-4684-9895-0
eBook Packages: Springer Book Archive