Title: Alternative Sweeteners

11
Sucralose
Leslie A. Goldsmith and Carolyn M. Merkel
McNeil Specialty Products Company, New Brunswick, New Jersey
I. INTRODUCTION
The high-quality sweetness of sucralose (SPLENDA ® Brand Sweetener) was discovered
as a consequence of a research program conducted at Queen Elizabeth
College at the University of London during the 1970s (1). Hough and his colleagues,
with the support of Tate & Lyle PLC, showed that the selective chlorination
of sugar could result in intensely sweet compounds (2). This discovery led
to a series of studies eventually exposing sucralose (1,6-dichloro-1,6-dideoxy-βd-fructofuranosyl-4-chloro-4-deoxy-α-d-galactopyranoside)
(Fig. 1) as the most
promising candidate as an ideal sweetener.
The selective chlorination of the sucrose molecule produced remarkable
changes to the sweetness intensity and stability of sucrose, without compromising
taste quality. Sucralose has a pleasant sweet taste similar to sucrose and has no
unpleasant aftertaste. Sucralose is a white, crystalline, nonhygroscopic, freeflowing
powder. The sweetener is highly soluble in water, ethanol, and methanol
and has negligible effect on the pH of solutions. The viscosity of sucralose solutions
is similar to that of sugar. Sucralose exerts negligible lowering of surface
tension.
The chlorination of sucrose in the 1 and 6 positions of the fructose moiety
and the inversion and chlorination of the 4 position on the glucose moiety causes
the remarkable stability of sucralose. The resulting glycosidic linkage of sucralose
is significantly more resistant to acid and enzymatic hydrolysis than that of
the parent compound. The resistance of the glycosidic bond is responsible for
the inability of mammalian species to digest the molecule and metabolize it as
an energy source. Therefore, sucralose is noncaloric. This resistant bond is also
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