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732 URINE.
C.CH3
Skatoxyl-sulphuric Acid, C9H9NSO4, C6H4<^Sc.O.S02.0H, has not
NH
been positively prepared as a constituent of normal urine, but Otto
has once prepared its alkali salt from diabetic urine. Perhaps skatoxyl
occurs in normal urine as a conjugated glucuronate (Mayer and Neu-
berg 1
), and it is believed that the urine contains a skatol-chromogen
from which red and reddish-violet coloring-matters are obtained by
decomposition with strong acids and an oxidizing agent.
Skatoxyl-sulphuric acid originates, if it exists in the urine, from
skatol, which is formed by putrefaction in the intestine, and which is
then conjugated with sulphuric acid after oxidation into skatoxyl. That
skatol introduced into the bodj- passes partly as an ethereal-sulphuric
acid into the urine has been shown by Brieger. Indol and skatol act
differently, at least in dogs, indol producing a considerable amount
of ethereal-sulphuric acid, while skatol gives only a small quantity (Mes-
ter 2
). Reports on this subject are at variance.
The conditions for the formation of indol and skatol by the putrefaction of
proteins in the intestine are decidedly different, according to Herter, as skatol
is produced by other putrefaction bacteria than indol. For example, bacillus coli
communis produces indol, but only traces of skatol, while skatol is formed by
certain anaerobic putrefactive bacteria. An important intermediary step in the
formation of skatol is the indol acetic acid (skatol carboxylic acid, according to
Salkowski) and this can also pass into the urine and is the chromogen of the
urorosein, according to Herter. 3
The potassium salt of skatoxyl-sulphuric acid is crystalline; it dis-
solves in water, but with difficulty in alcohol. A watery solution becomes
deep violet with ferric chloride. The solution becomes red with con-
centrated hydrochloric acid with the separation of a red precipitate.
This precipitate (skatol red) is, after washing with water, insoluble in
ether but soluble in amyl alcohol. On distillation with zinc-dust the
red pigment gives a strong odor of skatol.
Urines containing skatoxyl are colored dark red to violet by Jaffe’s
indican test even on the addition of hydrochloric acid alone; with nitric
acid they are colored cherry red, and red on warming with ferric chloride
and hydrochloric acid. A red coloration of the urine can also be brought
about by the appearance of indigo red (indirubin) and a confusion of
this pigment can also take place. Rosin 4
is of the opinion that no
l
Otto, Pflliger’e Arch., 33; Mayer and Neuberg, Zeitschr. f. physiol. Chem., 29.
2
Brieger, Ber. d. deutsch. chem. Gesellsch., 12, and Zeitschr. f. physiol. Chem.,
4, 414; Mester, ibid., 12.
3
Journ. of biol. Chem., 4.
* Rosin, Virchow’s Arch., 123.
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