Characterization of 3,4-dihydroxy-3-hexen-2,5-dione as the first open-chain caramel-like smelling flavor compound

Citation
W. Engel et al., Characterization of 3,4-dihydroxy-3-hexen-2,5-dione as the first open-chain caramel-like smelling flavor compound, EUR FOOD RE, 213(2), 2001, pp. 104-106
Citations number
9
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Food Science/Nutrition
Journal title
EUROPEAN FOOD RESEARCH AND TECHNOLOGY
ISSN journal
1438-2377 → ACNP
Volume
213
Issue
2
Year of publication
2001
Pages
104 - 106
Database
ISI
SICI code
1438-2377(200108)213:2<104:CO3ATF>2.0.ZU;2-5
Abstract
3,4-Dihydroxy-3-hexen-2,5-dione (DHHD) was identified in a thermally treate d mixture of cysteamine and fructose. GC/MS and C-13-NMR measurements revea led 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 (furan eol) and its odor threshold was determined to be 10 mug/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, odorl ess tautomer (diacetylformoin) is immediately formed in aqueous solution.