742 URINE. 



by JAFFE and LEVY, 1 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. 2 



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, 3 the quantity of ethereal-sulphuric acid in the urine, while 

 ROST asserts, contrary to earlier claims, that the same occurs with gallic 

 acid (trioxybenzoic acid) and tannic acid. 4 



While acetophenone (phenylmethylketone) , C 6 H 5 .CO.CH 3 , as shown 

 by M. NENCKI, is oxidized to benzoic acid and eliminated as hippuric acid, 

 the aromatic oxyketones with hydroxyl groups, such as resacetophenone, 



C 6 H 3 (OH) (OH) (CO.CH 3 ), paraoxypropiophenone, C 6 H 4 (OH) (COCH 2 .CH 3 ), 



123 4 



and gallacetophenone, C 6 H 2 (OH)(OH)(OH)(CO.CH 3 ), pass into the urine 

 without previous oxidation as ethereal-sulphuric acids and in part after 

 conjugation with glucuronic acid (NENCKI and REKOWSKI 5 ). Euxanthon, 

 which is also an aromatic oxyketone, passes into the urine as euxanthic 

 acid after the conjugation with glucuronic acid previously mentioned. 



A conjugation of other aromatic substances with glucuronic acid, which 

 last is protected from combustion, occurs rather often. The phenols, as 

 above stated (page 689), 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 HILDEBRANDT and FROMM 

 and CLEMENS 6 have shown that the cyclic terpenes and camphors, by oxida- 

 tion or hydration, or in certain cases by both, are converted into hydroxyl 

 derivatives when the body in question is not previously hydroxylized, and 



1 Levy, Ueber das Verhalten einiger Thiophenderivate, etc., Inaug.-Diss., Konigs- 

 berg, 1889; JaffS and Levy, Ber. d. d. chem. Gesellsch., 21. 



2 In regard to the literature, see O. Kiihling, 1. c. 



3 Zeitschr. f. physiol. Chem., 21. 



4 In regard to the action 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. 



5 Arch. d. scienc. biol. de St. Petersbourg, 3, and Ber. d. deutsch. chem. 

 Gesellsch., 27. 



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. 



