Chemical and Functional Properties of Food Saccharides

© 2004 by CRC Press LLC
In the presence of certain amino acids, the degradation of 3-deoxyosones yields
specific compounds not formed in other systems. For example, maltoxazine (18.35)
(an important component of malt or beer), tetrahydroindolizinone (18.36), and imidazolinone
(18.37) are formed as proline, hydroxyproline, and arginine specific
compounds, respectively. 44,45
18.6 DEGRADATION OF 1-DEOXY-2,3-DIULOSES
O
CH2 CH CH CH2 OH OH OH
O
N
N
18.35
O
18.36
1-Deoxy-2,3-diuloses are very reactive compounds that up to now were not isolated
as such from foods or from model systems. Only recently, 1-deoxy-D-erythro-hexo-
2,3-diulose was synthesized in a protected form that can be released under mild
conditions and its structure present in aqueous solution was elucidated. 46
Dehydration of 1-deoxy-2,3-diuloses gives rise to 3-furanones of type (18.38)
(Reaction 18.10). 47,48 4-Hydroxy-5-methyl-3(2H)-furanone (18.38b) and 4-hydroxy-
CH3 C O
C O
HC OH
HC OH
R
18.18
Reaction 18.10
2,5-dimethyl-3(2H)-furanone (18.38c) derived from pentoses and methylhexoses,
respectively, are important aroma substances. In the presence of sulfur-containing
O
O
N
NH CH2 CH2 CH2 CH COOH
NH NH2 18.37
HOO HOOH O OH
R O
OH
CH3 R O
OH
CH3 H2O R O CH3 18.38a R=CH 2OH
18.38b R=H
18.38c R=CH 3