Comparison of key aroma compounds in five different types of Japanese soy sauces by aroma extract dilution analysis (AEDA)

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 15, 2012, Pages 3831-3836

  Kaneko, Shu ^a   Kumazawa, Kenji ^a   Nishimura, Osamu ^a  

^a Flavor System and Technology Laboratory   (Japan)

Author keywords

4 HEMF; aroma extract dilution analysis; Japanese soy sauce; methional; sotolon

Indexed keywords

DILUTION; FINITE DIFFERENCE METHOD;

4-HEMF; AROMA EXTRACT DILUTION ANALYSIS; JAPANESE SOY SAUCES; METHIONAL; SOTOLON;

ODORS;

SOLANUM TUBEROSUM;

EID: 84859892831     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf300150d     Document Type: Article

References (41)

1. Yokotsuka, T.; Sasaki, M. Fermented protein foods in the Orient: shoyu and miso in Japan. In Microbiology of Fermented Foods; Wood, B. J., Ed.; Blackie Academic and Professional: London, U.K., 1998; Vol. 1 and 2, pp 351-415.
2. Isa, T. Seasoning. In Shokuhin-gaku; Kubota, K., Morimitsu, T., Eds.; Tokyo Kagaku Dojin: Tokyo, Japan, 2003; pp 244-253.
3. Nakadai, T. Flavour and taste of soy sauce Koryo 1998, 200, 69-80
4. Nunomura, N.; Sasaki, M.; Asao, Y.; Yokotsuka, T. Isolation and identification of 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2 H)-furanone, as a flavor component in shoyu (soy sauce) Agric. Biol. Chem. 1976, 40, 491-495
5. Monde, K.; Nakahashi, A.; Miura, N.; Yasuchi, Y.; Sugimoto, D.; Emura, M. Stereochemical study of a novel tautomeric furanone, homofuraneol Chirality 2009, 21, E110-E115
6. Blank, I.; Fay, L. B. Formation of 4-hydroxy-2,5-dimethyl-3(2 H)-furanone and 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2 H)-furanone through Maillard reaction based on pentose sugars J. Agric. Food Chem. 1996, 44, 531-536
7. Ohata, M.; Kohama, K.; Morimitsu, T.; Kubota, K.; Sugawara, E. The formation mechanism by yeast of 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2 H)-furanone in Miso Biosci., Biotechnol., Biochem. 2007, 71, 407-413
8. Hayashida, Y.; Nishimura, K.; Slaughter, J. C. Formation mechanism of flavour-active furanones, 4-hydroxy-2,5-dimethyl-3(2 H)-furanone (4-HDMF) and 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2 H)-furanone (4-HEMF), in Mugi-miso, fermented soy-beans paste with barley- Koji J. Brew. Soc. Jpn. 1998, 93, 730-738
9. Steinhaus, P.; Schieberle, P. Characterization of the key aroma compounds in soy sauce using approaches of molecular sensory science J. Agric. Food Chem. 2007, 55, 6262-6269
10. Amano, T. Aromas in soybean miso and tamari soy sauce V. Comparison of aroma components in the head space vapor from various soy sauces Aichi-ken Shokuhin Kogyo Shikensho Nenpo 1974, 15, 20-28
11. Amano, T.; Kudo, H. Studies on aroma in soybean Miso and Tamari soy sauce. Part 6. Changes of components in soy sauce by beating Aichi-ken Shokuhin Kogyo Shikensho Nenpo 1976, 17, 79-85
12. Kumazawa, K.; Wada, Y.; Masuda, H. Characterization of epoxydecenal isomers as potent odorants in black tea (Dimbula) infusion J. Agric. Food Chem. 2006, 54, 4795-4801
13. Kaneko, S.; Kumazawa, K.; Nishimura, O. Studies on the key aroma compounds in soy milk made from three different soybean cultivars J. Agric. Food Chem. 2011, 59, 12204-12209
14. Engel, W.; Bahr, W.; Schieberle, P. Solvent assisted flavour evaporation, a new and versatile technique for the careful and direct isolation of aroma compounds from complex food matrices Eur. Food Res. Technol. 1999, 209, 237-241
15. Schieberle, P. New developments in methods for analysis of volatile flavor compounds and their precursors. In Characterization of Food: Emerging Methods; Goankar, A., Ed.; Elsevier: Amsterdam, The Netherlands, 1995; pp 403-431.
16. Asao, Y.; Sakasai, T.; Yokotsuka, T. Studies of the flavorous substances in Shoyu part XXVI. Flavorous components produced by yeast fermentation J. Agric. Chem. Soc. Jpn. 1967, 41, 434-441
17. Aoki, T.; Uchida, K. Enhanced formation of 2-phenylethanol in Zygosaccharomyces rouxii due to prephenate dehydrogenase deficiency Agric. Biol. Chem. 1990, 54, 273-274
18. Fiddler, W.; Parker, W. E.; Wasserman, A. E.; Doerr, R. C. Thermal decomposition of ferulic acid J. Agric. Food Chem. 1967, 15, 757-761
19. Takahashi, K.; Tadenuma, M.; Sato, S. 3-Hydroxy-4,5-dimethyl-2(5 H)-furanone, a burnt flavoring compound from aged sake Agric. Biol. Chem. 1976, 40, 325-330
20. Pham, T. T.; Guichard, E.; Schlich, P.; Charpentier, C. Optimal conditions for the formation of sotolon from α-ketobutyric acid in the French "Vin Jaune" J. Agric. Food Chem. 1995, 43, 2616-2619
21. Kobayashi, A. Sotolon: identification, formation and effect on flavor. In Flavor Chemistry: Trends and Developments; Teranishi, R., Ed.; American Chemical Society: Wachington, DC, 1989; pp 49-59.
22. Pripis-Nicolau, L.; de Revel, G.; Bertrand, A.; Maujean, A. Formation of flavor components by the reaction of amino acid and carbonyl compounds in mild conditions J. Agric. Food Chem. 2000, 48, 3761-3766
23. Shaw, P. E.; Berry, R. E. Hexose-amino acid degradation studies involving formation of pyrrole, furans, and other low molecular weight products J. Agric. Food Chem. 1977, 25, 641-644
24. Dahlen, T.; Hauck, T.; Wein, M.; Schwab, W. 2,5-Dimethyl-4-hydroxy-3(2 H)-furanone as a secondary metabolite from d -fructose-1,6-diphosphate metabolism by Zygosaccharomyces rouxii J. Biosci. Bioeng. 2001, 91, 352-358
25. Kihara, K. Determination of maltol in soy sauce by liquid-liquid shaking extraction J. Jpn. Soy Sauce Res. Inst. 1987, 13, 211-214
26. Yamada, K.; Ino, M. Shoyu flavor by gas chromatography. II. Flavor components produced by shoyu koji microflora Chomi Kagaku 1969, 16, 15-20
27. Belitz, H. D.; Grosch, W.; Schieberle, P. Aroma compounds. In Food Chemstry, 4 th revised and extended ed.; Belitz, H. D.; Grosch, W.; Schieberle, P., Eds.; Springer-Verlag: Berlin, Germany, 2009; pp 340-402.
28. Higuchi, T.; Aoki, T.; Uchida, K. Esterase activitiy in soy sauce Moromi as a factor hydrolyzing flavor esters J. Ferment. Bioeng. 1991, 71, 163-167
29. Feather, M. S. Amine-assisted sugar dehydration reactions Prog. Food Nutr. Sci. 1981, 5, 37-45
30. Buttery, R. G.; Ling, L. C. Additional studies on flavor components of corn tortilla chips J. Agric. Food Chem. 1998, 46, 2764-2769
31. Akabori, S. Aroma of shoyu (soy sauce) I J. Chem. Soc. Jpn. 1936, 57, 828-831
32. Nunomura, N.; Sasaki, M.; Asao, Y.; Yokotsuka, T. Identification of volatile components in shoyu (soy sauce) by gas chromatography-mass spectrometry Agric. Biol. Chem. 1976, 40, 485-490
33. Sasaki, M.; Nunomura, N. Constituents of top note aroma of soy sauce J. Chem. Soc. Jpn. 1981, 736-745
34. Yokotsuka, T. Flavoring substances in soy sauce. VIII. Flavors with higher boiling points. 3. Benzaldehyde and ethyl benzoate J. Agric. Chem. Soc. Jpn. 1951, 25, 446-450
35. 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 J. Jpn. Soc. Food Sci. Technol. 1996, 43, 1063-1074
36. Nunomura, N.; Sasaki, M.; Yokotsuka, T. Shoyu (soy sauce) flavor components: acidic fractions and the characteristic flavor component Agric. Biol. Chem. 1980, 44, 339-351
37. Kihara, K. The aroma of soy sauce I-III J. Soc. Chem. Ind. Jpn. 1940, 43, 876-883
38. Yokotsuka, T. Flavoring substances in soy sauce IX. Flavors with higher boiling points. 4. Isolation of phenolic flavoring substances J. Agric. Chem. Soc. Jpn. 1953, 27, 276-281
39. Nunomura, N.; Sasaki, M.; Yokotsuka, T. Isolation of 4-hydroxy-5-methyl- 3(2 H)-furanone, a flavor component in shoyu (soy sauce) Agric. Biol. Chem. 1979, 43, 1361-1363
40. Sugawara, E. Formation by yeast of the aroma component specific to miso and soy sauce Food Ingred. J. Jpn. 2001, 193, 57-65
41. Kihara, K. Capillary gas chromatographic pattern of volatile components in shoyu and their relation to quality. I. Preliminary experiment and GC-MS J. Jpn. Soy Sauce Res. Inst. 1986, 12, 12-19