TY - JOUR
T1 - Characterization of 3,4-dihydroxy-3-hexen-2,5-dione as the first open-chain caramel-like smelling flavor compound
AU - Engel, Wolfgang
AU - Hofmann, Thomas
AU - Schieberle, Peter
PY - 2001
Y1 - 2001
N2 - 3,4-Dihydroxy-3-hexen-2,5-dione (DHHD) was identified in a thermally treated mixture of cysteamine and fructose. GC/MS and 13C-NMR measurements revealed that its flavor activity is present only in the open chain form, while the cyclic species was shown to be completely odorless. The flavor quality of DHHD was similar to that of 4-hydroxy-2,5-dimethyl-3(2H)-furanone (furaneol) and its odor threshold was determined to be 10 μg/l in sunflower oil. NMR measurements, however, showed that the odor-active open chain tautomer is present only in aprotic solvents, such as oils, while the cyclic, odorless tautomer (diacetylformoin) is immediately formed in aqueous solution.
AB - 3,4-Dihydroxy-3-hexen-2,5-dione (DHHD) was identified in a thermally treated mixture of cysteamine and fructose. GC/MS and 13C-NMR measurements revealed that its flavor activity is present only in the open chain form, while the cyclic species was shown to be completely odorless. The flavor quality of DHHD was similar to that of 4-hydroxy-2,5-dimethyl-3(2H)-furanone (furaneol) and its odor threshold was determined to be 10 μg/l in sunflower oil. NMR measurements, however, showed that the odor-active open chain tautomer is present only in aprotic solvents, such as oils, while the cyclic, odorless tautomer (diacetylformoin) is immediately formed in aqueous solution.
KW - 3,4-Dihydroxy-3-hexen-2,5-dione
KW - Diacetylformoin
UR - https://www.scopus.com/pages/publications/2142770299
U2 - 10.1007/s002170100351
DO - 10.1007/s002170100351
M3 - Article
AN - SCOPUS:2142770299
SN - 1438-2377
VL - 213
SP - 104
EP - 106
JO - European Food Research and Technology
JF - European Food Research and Technology
IS - 2
ER -