2009_Book_FoodChemistry

8.8 Sweeteners 441
pounds with active methylene groups, as exemplified
by 1,3-diketones, 3-oxocarboxylic acids and
3-oxocarboxylic acid esters:
Table 8.10. Comparison of sweetening strengths of
aspartame and saccharose (concentrations of isosweet
aqueous solutions in %)
Saccharose Aspartame f sac, g
0.34 a 0.001 a 340
4.3 0.02 215
10.0 0.075 133
15.0 0.15 100
a Threshold value.
approved for use as a sweetener in North
America (aspartame, “NutraSweet”). It is as
sweet as a number of other dipeptide esters of
L-aspartic acid and D,L-aminomalonic acid. The
relationship between chemical structure and
taste among these compounds was outlined in
more detail in 1.3.3. The sweetening strength
relative to saccharose is concentration dependent
(Table 8.10). Aspartame is used worldwide,
though its stability is not always satisfactory.
Unlike sweetening of drinks (coffee or tea) which
are drunk immediately, problems arise in the
use of aspartame in food which has to be heated
or in sweetened drinks which have to be stored
for longer periods of time. Possible degradation
reactions involve α/β-rearrangement, hydrolysis
Table 8.11. Taste of some dipeptide amides of the type
L-Asp-D-Ala-NHR
R f sac, g (10)
(8.16)
The sweetness of acesulfame is perceived quickly
and this substance is practically stable in foods
under the common processing and storage conditions.
It is used in a large number of different
products.
8.8.15 Dipeptide Esters and Amides
8.8.15.1 Aspartame
A dipeptide, L-aspartyl-L-phenylalanine methyl
ester (L-Asp-L-Phe-OMe), has recently been
Cyclopentyl 50
Cyclohexyl 90
(2,2,5,5-tetramethyl)-cyclopentyl 800
(2,2,6,6-tetramethyl)-cyclohexyl 300
(Diethyl)-methyl 100
(Diisopropyl)-methyl 250
(Di-tert-butyl)-methyl 450
(Di-cyclopropyl)-methyl 1200
(Cyclopropyl)-(tert-butyl)-methyl 1200
(Cyclopropyl)-(methyl)-methyl 100
(2,2,4,4-Tetramethyl)-cyclobutyl 300
(2,2,4,4-Tetramethyl)-cyclobutan-3-onyl 240
(3-Hydroxy-2-2,2,4,4-tetramethyl)-cyclobutyl 125
3-(2,2,4,4-Tetramethyl)-thietanyl
2000 a
3-(1-cis-Oxo-2,2,4,4-tetramethyl)-thietanyl 300
3-(1-trans-Oxo-2,2,4,4-tetramethyl)-thietanyl 350
3-(1,1-Dioxo-2,2,4,4-tetramethyl)-thietanyl 805
a Alitame.