Abstract
Volatile components in the Maillard reaction (1912) have been investigated by a large number of researchers for a long time. Maltol is one of the best known compounds as the sweet aroma during the processing of foods and agricultural products. Sekiwa (1997) reported that 3-hydroxy-2-methyl-4(H)-pyrane-4-one (maltol) was detected in the brew of cooked clams, and the increase in maltol was conspicuous, reaching 4 times the original value within 0–15 min of boiling time. In this study, maltol already existed in the brew of clams before boiling. Therefore, it can be assumed that maltol was produced from other reactions without participation of the amino carbonyl reaction by heating. On the other hand, Ishihara (1996) detected maltol in soybean sauce. 2,3-Dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one was attached through an acetal linkage to the C-22 hydroxyl of the aglycones of soybean saponins (DDMP-conjugated soybean saponins) as detected by Kuduo et al. (1992). Maltol in soybean sauce might be formed form these DDMP-conjugated soybean saponins.
The formation of maltol in a Maillard reaction in a dry system was investigated by the detection of volatile components formed in actual cookies by HPLC and also by the measurement of those formed from the reaction of mono-, di-or trisaccharides added under dry conditions as a model system of cookie processing. 3-Hydroxy-2-methyl-4(H)-pyran-4-one (maltol) is reported to be formed by the decomposition of 2,3-dihydro-3,5-dihydroxy-6-methyl-4(H)pyran-4-one (DDMP). If that is true, DDMP is the prime compound in the pathway to maltol in the Maillard reaction. DDMP was formed in both the actual cookies and model amino carbonyl reactions. However, maltol was not detected in every reaction of these dry systems. Another pathway, not through DDMP, seems to exist in the formation of maltol.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Cutzach, I.; Chattonnet, P.; Henry, R.; Dubourdieu, D. Identification of volatile compounds with a “toasty” aroma in heated oak used in barrelmaking. J Agric. Food Chem. 1997, 45, 2217–2224.
Hodge, J.E.; Mills, F.D.; Fisher, B.E. Compounds of browning flavor derived from sugar-amine reaction. Cereal Chem. 1972, 17, 34–40.
Ishihara, K.; Honma, N.; Matsumoto, I.; Imai, S.; Nakazawa, S.; Iwafuchi, H. Comparison of volatile components in soy sauce (Koikuchi Shoyu) produced using Aspergillus sojae and Aspergillus oryzae. Nippon Shokuhin Kagaku Kogaku Kai.shi. 1996, 48, 1063–1074.
Kim, M.; Baltes, W. On the role of 2,3-dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one in the Maillard Reaction. J. Agric. Food Chem. 1996, 44, 282–289.
Kudou, S.; Tonomura, M.; Tsukamoto, D.; Shimoyamada, M.; Uchida, T.; Okubo, K. Isolation and structural eluci-dation of the major genuine soybean saponin. Biosci. Biotech. Biochem. 1992, 56, 142–143.
Maillard, L.C. Action of amino acids on sugars. Formation of melanoidins in a methodical way. Compt. Rend. 1912, 154, 66–68.
Nishibori, S.; Kawakishi, S. Changes in baking products of cookie dough composed of different materials. Nippon Shokuhin Kogyo Gakkaishi. 1988, 35, 235–241.
Nishibori, S.; Kawakishi, S. Effects of dough materials on flavor formation in baked cookies. J. Food Sci. 1990, 55, 409–412.
Nishibori, S.; Kawakishi, S. Effect of various sugars on the quality of baked cookies. Cereal Chem. 1992, 69, 160–164.
Nishibori, S.; Bernhard, R.A. Model system for cookies; volatile components formed from the reaction of sugar and 3-alanine. J. Agric. Food Chem. 1993, 41, 2374–2377.
Nishibori, S.; Kawakishi, S. Formation of 2,3-dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one from fructose with 0-alanine under condition used for baking. J. Agric. Food Chem. 1994, 42, 1080–1084.
Njoroge, F.G.; Monnier, V.M. The Chemistry of the Maillard reaction under physiological conditions: A Review. In The Maillard Reaction of Aging Diabetes, and Nutri.; Alan R. Liss Inc., 1989, 85–107.
Sekiwa, Y.; Kubota, K.; Kobayashi, A. Characteristic flavor components in the brew of cooked clam (Meretrix Lusoria) and the effect of storage on flavor formation. J. Agric. Food Chem. 1997, 45, 826–830.
Shaw, P.E.; Tatum, J.H.; Berry, R.E. Acid-catalyzed degradation of D-fructose. Carbohyd. Res. 1967, 5, 266–273.
Shaw, P.E.; Tatum, J.H.; Berry, R.E. Base-catalyzed degradation and relation to nonenzymic browning..J. Agric. Food Chem. 1968, 16, 979–982.
Yaylayan, V.A.; Mandeville, S. Structural features of ortho elimination reactions of amadori rearrangement products under electron impact condition. Spectroscopy 1991, 9, 73–78.
Yaylayan, V.A.; Mandeville, S. Stereochemical control of maltol formation in Maillard reaction. J. Agric. Food Chem. 1994, 42, 771–775.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1999 Springer Science+Business Media New York
About this chapter
Cite this chapter
Nishibori, S., Osawa, T., Kawakishi, S. (1999). Volatile Components Formed from Various Sugars with β-Alanine in Actual Cookies. In: Shahidi, F., Ho, CT. (eds) Flavor Chemistry of Ethnic Foods. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-4783-9_23
Download citation
DOI: https://doi.org/10.1007/978-1-4615-4783-9_23
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4613-7166-3
Online ISBN: 978-1-4615-4783-9
eBook Packages: Springer Book Archive