Determination of 4-Hydroxy-2,5-dimethyl-3(2H)-furanone and 2(or 5)-Ethyl-4-hydroxy-5(or 2)-methyl-3(2H)-furanone in Pentose Sugar-Based Maillard Model Systems by Isotope Dilution Assays

Journal of Agricultural and Food Chemistry

Volumn 45, Issue 7, 1997, Pages 2642-2648

  Blank, Imre ^a   Fay, Laurent B ^a   Lakner, Frederick J ^b,c   Schlosser, Manfred ^b  

^a NESTLÉ RESEARCH CENTER   (Switzerland)

^b UNIVERSITY OF LAUSANNE   (Switzerland)

^c UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

1,2 dione; 2(or 5) ethyl 4 hydroxy 5(or 2) methyl 3(2H) furanone; 4 hydroxy 2,5 dimethyl 3(2H) furanone; Alcohol protection; Alkyne oxidation; Furaneol; Homofuraneol; Maillard reaction; Pentose model system; Stable isotope label; Synthesis

Indexed keywords

EID: 0001095738     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf960997i     Document Type: Article

References (22)

1. Beck, J.; Ledl, F.; Severin, T. Formation of 1-deoxy-D-erythro-2,3-hexodiulose from Amadori compounds. Carbohydr. Res. 1988, 177, 240-243.
2. Blank, I.; Fay, L. B. Formation of 4-hydroxy-2,5-dimethyl-3(2H)-furanone and 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone through Maillard reaction based on pentose sugars. J. Agric. Food Chem. 1996, 44, 531-536.
3. Blank, I.; Devaud, S.; Fay, L. B. New aspects on the formation of 3(2H)-furanones through the Maillard reaction. In Flavour Science. Recent Developments; Taylor, A. J., Mottram, D. S., Eds.; The Royal Society of Chemistry: Cambridge, 1996a; pp 188-193.
4. Blank, I.; Lin, J.; Fumeaux, R.; Welti, H. D.; Fay, L. B. Formation of 3-hydroxy-4,5-dimethyl-2(5H)-furanone (sotolone) from 4-hydroxy-L-isoleucine and 3-amino-4,5-dimethyl-3,4-dihydro-2(5H)-furanone. J. Agric. Food Chem. 1996b, 44, 1851-1856.
5. Blank, I.; Sen, A.; Grosch, W. Potent odorants of the roasted powder and brew of Arabica coffee. Z. Lebensm. Unters. Forsch. 1992, 195, 239-245.
6. Eren, D.; Keinan, E. Total synthesis of linear polyprenoids. 3. Syntheses of ubiquinones via palladium-catalyzed oligomerization of monoterpene monomers. J. Am. Chem. Soc. 1988, 110, 4356-4362.
7. Feather, M. S. Amine-assisted sugar dehydration reactions. Prog. Food Nutr. Sci. 1981, 5, 37-45.
8. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991; p 387.
9. Guth, H., Grosch, W. Deterioration of soya-bean oil: Quantification of primary flavour compounds using a stable isotope dilution assay. Lebensm. Wiss. Technol. 1990, 23, 513-522.
10. Hirvi, T.; Honkanen, E.; Pyysalo, T. Stability of 2,5-dimethyl-4-hydroxy-3(2H)-furanone and 2,5-dimethyl-4-methoxy-3(2H)-furanone in aqueous buffer solutions. Lebensm. Wiss. Technol. 1980, 13, 324-325.
11. Hodge, J. E.; Mills, F. D.; Fisher, B. E. Compounds of browned flavor derived from sugar-amine reactions. Cereal Sci. Today 1972, 17, 34-40.
12. Huber, U. A. Homofuronol: A powerful tool to prepare and improve sophisticated high quality flavors. Perfum. Flavor. 1992, 17 (4), 15-19.
13. Ledl, F.; Schleicher, E. New aspects of the Maillard reaction in foods and in the human body. Angew. Chem., Int. Ed. Engl. 1990, 29, 565-594.
14. Mazenod, F.; Delay, F.; Näf, F. 2,5-Dimethyl-4-hydroxy-3(2H)-furanone (Furaneol) from methyl α-D-glucopyranoside. Chimia 1992, 46, 403-405 (and references therein).
15. Olah, G. A.; Arvanaghi, M. Aldehydes by formylation of Grignard or organolithium reagents with N-formylpiperidine. Angew. Chem., Int. Ed. Engl. 1981, 20, 878-879.
16. Pickenhagen, W.; Velluz, A.; Passerat, J.-P.; Ohloff, G. Estimation of 2,5-dimethyl-4-hydroxy-3(2H)-furanone (Furaneol) in cultivate of wild strawberries, pineapples, and mangoes. J. Sci. Food Agric. 1981, 32, 1132-1134.
17. Preininger, M.; Grosch, W. Evaluation of key odorants of the neutral volatiles of Emmentaler cheese by the calculation of odour activity values. Lebensm. Wiss. Technol. 1994, 27, 237-44.
18. Re, L.; Maurer, G; Ohloff, G. Simple access to 4-hydroxy-2,5-dimethyl-3(2H)-furanone (Furaneol), aroma component of the pineapple and strawberry. Helv. Chim. Acta, 1973, 56, 1882-1894 (in German); Chem. Abstr. 1973, 79, 115381y.
19. Re, L.; Maurer, G; Ohloff, G. Simple access to 4-hydroxy-2,5-dimethyl-3(2H)-furanone (Furaneol), aroma component of the pineapple and strawberry. Helv. Chim. Acta, 1973, 56, 1882-1894 (in German); Chem. Abstr. 1973, 79, 115381y.
20. Schieberle, P.; Grosch, W. Quantitative analysis of aroma compounds in wheat and rye bread crusts using stable isotope dilution assay. J. Agric. Food Chem. 1987, 35 252-257.
21. Semmelroch, P.; Laskawy, G.; Blank, I.; Grosch, W. Determination of potent odourants in roasted coffee by stable isotope dilution assays. Flavour Fragrance J. 1995, 10, 1-7.
22. Sen, A.; Schieberle, P; Grosch, W. Quantitative determination of 2,5-dimethyl-4-hydroxy-3(2H)-furanone and its methyl ether using a stable isotope dilution assay. Lebensm. Wiss. Technol. 1991, 24, 364-369.