2009_Book_FoodChemistry

8.8 Sweeteners 439
8.8.9 Phyllodulcin
The leaves of Hydrangea macrophylla contain
a 3,4-dihydroisocoumarin derivative, phyllodulcin
(Formula 8.8). Its sweetness matches that of
dihydrochalcones and of licorice root.
(8.8)
The taste perception builds relatively slowly and
also fades away slowly. The sweetening strength
is f sac (5) =250. A study of a number of related
isocoumarin derivatives shows that taste quality
and strength are very much dependent on the substitution
pattern of the molecule (cf. Table 8.7).
Table 8.7. Sensory properties of some 2,3-dihydroisocoumarins
Compound a
X Y Z Taste
OMe OH OH very sweet
OMe OMe OH bitter
OMe OMe OMe no taste
OMe OAc OAc slightly sweet
OH OH OH no taste
OH H OH no taste
OH OH H no taste
OMe OH H very sweet
OH OMe H no taste
a Formula 8.8.
β-neohesperidin dihydrochalcone is f sac, g = 1100
(threshold value) or f sac, g (10) =667 (R = β-
neohesperidosyl in Formula 8.10).
8.8.10 Glycyrrhizin
The active substance from licorice root
(Glycyrrhiza glabra) is a β,β ′ -glucuronidoglucuronide
of glycyrrhetic acid:
(8.9)
The sweetening strength is f sac, g (4) =50. The
compound is utilized for production of licorice
(also spelled as liquorice). Its cortisone-like side
effect limits its wide application.
8.8.11 Dihydrochalcones
Some dihydrochalcones are derived from flavanones
(cf. 18.1.2.5.4) and have a relatively
clean sweet taste that is slowly perceived but persists
for some time. The sweetening strength of
(8.10)
In different countries, this compound is used in
chewing gum, mouthwashes, beverages, and various
types of candy. The quality and strength of
the sweet taste of dihydrochalcone are related particularly
to the substitution pattern in ring B. The
prerequsite for a sweet taste is the presence in ring
B of at least one hydroxy group, but not three adjacent
hydroxy and alkoxy substituents.
8.8.12 Ureas and Guanidines
8.8.12.1 Suosan
Suosan, N-[(p-nitrophenyl)carbamoyl]-β-alanine
(Formula 8.11), f sac, g (2) = 700, is clearly
sweeter than saccharin. The e/n system could
be the NH/COO − system of β-alanine, which
corresponds to the e/n system of aspartame
(cf. 1.3.3 and 8.8.15). The p-cyanophenyl compound
( f sac, g (2) =450), the N-glycine homolog