Other names:
1,2-Benzisothiazol-3(2H)-one 1,1-dioxide
2,3-Dihydro-3-oxobenzisosulfonazole
1,2-Dihydro-2-ketobenzisosulfonazole
Benzosulfimide
o-Sulfobenzimide
Benzoic sulfimide
o-Sulfobenzoic acid imide
Gluside
Glucid
Garantose
Saccharinol
Saccharinose
Saccharol
Saxin
Sykose
Hermestas
Sodium salt:
Soluble saccharin
Saccharin sodium
Kristallose
Crystallose
Dagutan
Sucaryl
Sucromat
Taste:
Saccharin has a sweet taste; many (but
not all) people experience
a bitter-metallic aftertaste. Its onset of sweetness is rapid. The
sweetness potency relative to sucrose is about 300, but depends upon
the concentration of sucrose which is being matched. The concentration vs.
response relationship in water is
shown below (results in
food systems will vary).
This graph is based on data from DuBois, Walters,
Schiffman, Warwick, Booth, Pecore, Gibes, Carr & Brands in
"Sweeteners: Discovery, Molecular Design, and Chemoreception," D.E.
Walters et al., Eds., American Chemical Society, 1991. The equation
allows you to calculate sweetness
response (R) for any
concentration (C). The units of R are percent sucrose equivalent; the
units of C are parts per million (ppm). The
saccharin data were fit to a Hill-type equation (exponential).
Calories:
Saccharin has no calories.
Safety:
Saccharin (as the sodium or calcium salt) is quite water soluble.
It is absorbed in the stomach (the acidic environment in the
stomach neutralizes the salt to the free acid form). It is
rapidly excreted in
the
kidneys. Saccharin has been shown to produce urinary bladder
tumors in rats, and this led to a ban in some countries and a proposed
ban in the US. Rather than banning saccharin, the US
government
required that products containing saccharin must bear a warning label.
The International Agency for Research
on Cancer has
found that a combination of sodium saccharin with high pH, high calcium
phosphate concentration, and high protein concentration (which is
unique to rats) causes formation of a solid material in the rat bladder
[1]. This material damages the rat's bladder
and
provokes overactive regrowth of bladder cells. This
phenomenon
has not been observed in mice or in any other species, including
humans. Thus, it is likely that saccharin carcinogenic only
in
rats, and that it is quite safe for humans. See my essay on
saccharin and cancer.
Chemistry:
Saccharin is an organic acid with a pKa of 1.6
[2]. It is most
commonly used as the sodium salt. The calcium salt and free
saccharin are also used.
Properties:
Saccharin is very stable.
Discovery:
There is some controversy over the discovery of saccharin. Constantine
Fahlberg was working in the laboratory of Ira Remsen at Johns Hopkins
University. According to Fahlberg's account, he accidentally
spilled
some laboratory material on his hand, and noticed the sweet taste later
in the evening when he was eating dinner. Fahlberg and Remsen published
the work jointly
[3]. Later
Fahlberg
patented saccharin without including Remsen on the patent.
Fahlberg
went on to become wealthy. Remsen went on to become the
president of
Johns Hopkins University, and he commented "Fahlberg is a scoundrel. It
nauseates me to hear my name mentioned in the same breath with him."
References:
1. Dybing, E. Development and
implementation of the IPCS conceptual framework for evaluating mode of
action of chemical carcinogens.
Toxicol. 181-182:121-125 (2002).
2. Marvel, J.R.; Lemberger, A.P. An
investigation of solvent effect upon saccharin complexes with
N,N-dimethylacetamide.
J. Amer. Pharm. Assoc. 49:420-422 (1960).
3. Fahlberg, C.; Remsen, I. Ueber die Oxydation des
Orthotoluolsulfamids
. Chem. Ber. 12:469-473 (1879).
Other links:
Saccharin on Wikipedia