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CONJUGATION OF AROMATIC SUBSTANCES. 785
Rost asserts, contrary to earlier claims, that the same occurs with gallic
acid (trioxybenzoic acid) and tannic acid. 1
Although Nencki and Rekowski 2
have shown that acetophenone (phen-
ylmethylketone), CeH5.CO.CH3, is oxidized to benzoic acid and eliminated
as hippuric acid, the aromatic oxyketones with hydroxyl groups, such as
resacetophenone, 2, 4 dioxacetophenone (HO)2.CcH3.CO.CH3, pass into
the urine as ethereal-sulphuric acids and in part after conjugation with
glucuronic acid. Euxanthon, which is also an aromatic ketone, namely
CO
dioxyxanthon, HO.CoH3< >CeH3.0H, passes into the urine as eux-
x cr
anthic acid after conjugation with glucuronic acid.
A conjugation of other aromatic substances with glucuronic acid,
which last is protected from combustion, occurs rather often. The phenols,
as above stated (page 725), pass in part as conjugated glucuronic acids
into the urine. The same is true for the homologues of the phenols, for
certain substituted phenols, and for many aromatic substances, also
hydrocarbons after previous oxidation and hydration. Thus Hilde-
brandt and Fromm and Clemens 3
have shown that the terpenes and cam-
phors, by oxidation or hydration, or in certain cases by both, are converted
into hydroxyl derivatives when the body in question is not previously
hydroxylized, and that these hydroxyl derivatives are eliminated as con-
jugated glucuronic acids. Conjugated glucuronic acids are detected in
the urine after the introduction of various substances into the organsim,
e.g., therapeutic agents, such as terpenes, borneol, menthol, camphor (cam-
phoglucuronic acid was first observed by Schmiedeberg), naphthalene,
oil of turpentine, oxyquinolines, antipyrine, and many other bodies.4
Orthonitrotoluene in dogs passes first into o-nitrobenzyl alcohol and then
1
In regard to the behavior of gallic and tannic acids in the animal body, see C.
Morner, Zeitschr. f. physiol. Chem., 16, which also contains the earlier literature; also
Harnack, ibid., 24, and Rost, Arch. f. exp. Path. u. Pharm., 38, and Sitzungsber. d.
Gesellsch. zur Beford. d. ges. Naturwiss. zu Marburg, 1898.
2
Arch. d. scienc. biol. de St. Petersbourg, 3, and Ber. d. deutsch. chem.
Gesellsch., 27.
3
Hildebrandt, Arch. f. exp. Path. u. Pharm., 45, 46; Zeitschr. f. physiol. Chem.,
36; with Fromm, ibid., 33; and with Clemens, ibid., 37; Fromm and Clemens, ibid.,
34. Extensive investigations on the behavior of alicylic compounds with the glucuronic
acid conjugation in the organism have been carried out by Hiimalainen, Skand. Arch,
f. Physiol., 27.
4
See O. Kiihling, 1. c, which gives the literature up to 1887; also E. Kiilz, Zeitschr.
f. Biologie, 27; the works of Hildebrandt, Fromm and Clemens, see footnote 3;
Brahm, Zeitschr. f. physiol. Chem., 28; Fenyvessy, ibid., 30; Bonanni, Hofmeister’s
Beitrage, 1; Lawrow, Ber. d. d. chem. Gesellsch., 33.
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