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SYNTHESES OF AROMATIC SUBSTANCES. 783
rectly to Keller and Ure. All the numerous aromatic substances which
are converted into benzoic acid in the body are voided partly as hippuric
acid. This statement is not true for all species of animals. According
to the observations of Jaffe, 1
benzoic acid does not pass into hippuric
acid in birds, but after conjugation with ornithin, into the correspond-
ing acid, ornithuric acid, (a-5-dibenzoyldiamino valeric acid). Not only
are the oxybcnzoic acids and the substituted benzoic acids conjugated with
glycocoll, forming corresponding hippuric acids, but also the above-
mentioned acids, toluic, mesitylenic, cumic, and phenylacetic acids. These
acids are voided as toluric, mcsitylcnuric, cuminuric, and phenaceturic
acids.
It must be remarked in regard to the oxybcnzoic acids that a conjugation with
glycocoll has been shown only with salicylic and p-oxybenzoic acid (Bertagnim,
and others), while Baumann and Herter 2
find it only very probable for m-
oxyhenzoic acid. According to Baldoni, 3
in dogs, the salicylic acid docs not pass
into salicyluric acid, and he indeed found two acids which he calls ursalicylic
acid, CuHuOs and uramin-salicylic acid, CieHieNOs. The oxybcnzoic acids are
also in part eliminated as conjugated sulphuric acids, which is especially true for
?/;-oxybenzoic acid. The three aminobenzoic acids, according to the experiments
of Hildebrandt, on rabbits, appeared at least in part unchanged in the urine.
Salkowski found, as was later confirmed by R. Cohn, 4
that in rabbits ///-amino-
benzoic acid passes in part into vmviiiiobenzoic acid, H2 N.CO.HX.C6 H.i.COOH.
It is also in part eliminated as aminohippuric acid.
The behavior of the halogen-substituted compounds of toluene varies in
different animals according to Hildebrandt’s experiments. In dogs they are
converted into the corresponding substituted hippuric acid. In rabbits o-brom-
toluene is completely changed to hippuric acid, the m- and p-bromtoluene only
partly. The three chlortoluenes are converted in rabbits into the corresponding
benzoic acid and are eliminated as such and not as hippuric acid.
The substituted aldehydes are of special interest as substances which
may undergo conjugation with glycocoll. According to the investiga-
tions of R. Cohn 5
on this subject, o-nitrobcnzaldeh]/de when introduced
into a rabbit is only in a very small part converted into nitrobenzoic
acid, and the chief mass, about 90 per cent, is destroyed in the body.
According to Sieber and Smirnowt 6 m-nitrobenzaldchyde passes in dogs
into w-nitrohippuric acid, and according to Cohn into urea-m-nitro-
hippurate, but in rabbits a different action results. In this case not only
does an oxidation of the aldehyde into benzoic acid take place, but the
1
Ber. d. d. chem. Gesellsch., 10 and 11.
2
Zeitschr. f. physiol. Chem., 1, where Bertagnini’s work is also cited. See also-
Dautzenberg, Maly’s Jahresber., 11, 231.
3
Arch. f. exp. Path. u. Pharm., 1908, Suppl. Bd. (Schmiedeberg’s Festschrift).
4
Salkowski, Zeitschr. f. physiol. Chem., 7; Cohn, ibid., 17; Hildebrandt, Hof-
meister’s Beit rage, 3.
6
Zeitschr. f. physiol. Chem., 17.
6
Monatshefte f. Chem., 8.
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