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784 URINE.
nitro-group is also reduced to an amino-group, and finally acetic acid
attaches itself to this with the expulsion of water, so that the final product
is m-acetylaminobenzoic acid, (CH3 .CO).NH.C6H4COOH. The p-nitro-
benzaldehyde acts in rabbits in part like the m-aldehyde and passes in
part into p-acetylaminobenzoic acid. Another part is converted into
p-nitrobenzoic acid, and the urine contains a chemical combination of
equal parts of these two acids. According to Sieber and Smirnow p-
nitrobenzaldehyde yields only urea p-nitrohippurate in dogs. The above-
mentioned pyridine-carboxylic acid, formed from methylpyridine
(a-picoline) passes into the urine after conjugation with glycocoll as
a-pyridinuric acid. 1
To those substances which undergo a conjugation with glycocoll
belongs also furfurol (the aldehyde of pyromucic acid, C4H3O.CHO),
which, when introduced into rabbits and dogs, as shown first by Jaffe
and Cohn,2
and then further shown by Sasaki and Friedmann, is elimi-
nated in two ways from the body. The furfurol can, by a similar synthesis
to Perkin’s reaction, be transformed into the unsaturated Sicidfurfuracrylic
acid C4H3 O.CH:CH.COOH, and also into pyromucic acid C4H3O.COOH.
These two acids pass, after conjugation with glycocoll, into the urine as
furfuracryluric acid and pyromucuric acid. In birds the pyromucic acid
is conjugated with ornithine and is eliminated as pyromucinornithuric acid.
It has not been proved how thiophene, C4H4S, behaves in the animal
body. Of methylthiophene (thiotolene), C4H3S.CH3, a very small part is
oxidized to thiophenic acid, C4H3S.COOH (Levy). This acid, as shown
by Jaffe and Levy,3
is conjugated with glycocoll in the body (rabbits)
and eliminated as thiophenuric acid.
Another very important synthesis of aromatic substances is that of
the ethereal-sulphuric acids. Phenols, and in particular the hydroxylated
aromatic hydrocarbons and their derivatives are voided as ethereal-sul-
phuric acids, according to Baumann, Herter and others.4
A conjugation of aromatic acids with sulphuric acid occurs less often.
The two previously mentioned aromatic acids, p-oxyphenylacetic and
p-oxyphenylpropionic acid, are in part eliminated in this form. Gentisic
acid (hydroquinone-carboxylic acid) also increases, according to Lik-
hatscheff,5
the quantity of ethereal-sulphuric acid in the urine, while
1
In regard to the extensive literature on glycocoll conjugations we refer the reader
to O. Kuhling, Ueber Stoffwechselprodukte aromatischer Korper. Inaug.-Diss.,
Berlin, 1887.
2
Ber. d.d. Chem. Gesellsch., 20 and 21; Sasaki and Friedmann, footnote 1, page 782.
3
Levy, Ueber das Verhalten einiger Thiophenderivate, etc., Inaug.-Diss., Konigs-
berg, 1889; Jaffe and Levy, Ber. d. d. chem. Gesellsch., 21.
* In regard to the literature, see O. Kuhling, 1. c.
6
Zeitschr. f. physiol. Chem., 21.
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