Food Chemistry

8.8 Sweeteners 439

8.8.9 Phyllodulcin

The leaves ofHydrangea macrophyllacontain
a 3,4-dihydroisocoumarin derivative, phyllodul-
cin (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
isfsac( 5 )=250. A study of a number of related
isocoumarin derivatives shows that taste quality
and strength are very much dependent on the sub-

stitution pattern of the molecule (cf. Table 8.7).

8.8.10 Glycyrrhizin

The active substance from licorice root
(Glycyrrhiza glabra)isaβ,β′-glucuronido-
glucuronide of glycyrrhetic acid:

(8.9)

The sweetening strength isfsac, 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 fla-
vanones (cf. 18.1.2.5.4) and have a relatively
clean sweet taste that is slowly perceived but per-
sists for some time. The sweetening strength of

Table 8.7.Sensory properties of some 2,3-dihydro-

isocoumarins

Compounda

XYZTaste

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

aFormula 8.8.

β-neohesperidin dihydrochalcone isfsac, g= 1100

(threshold value) orfsac, g( 10 )=667 (R=β-

neohesperidosyl in Formula 8.10).

(8.10)

In different countries, this compound is used in

chewing gum, mouthwashes, beverages, and var-

ious types of candy. The quality and strength of

the sweet taste of dihydrochalcone are related par-

ticularly 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 ad-

jacent 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), fsac, g( 2 )=700, is clearly

sweeter than saccharin. The e/n system could

be the NH/COO−system ofβ-alanine, which

corresponds to the e/n system of aspartame

(cf. 1.3.3 and 8.8.15). The p-cyanophenyl com-

pound (fsac, g( 2 )=450), the N-glycine homolog