782 



URINE. 



this is probably formed from the phenyl-/3-oxypropionic acid by the with- 

 drawal of water: 



C 6 H 5 .CH(OH) .CH 2 .COOH - H 2 = C 6 H 5 .CH :CH.COOH. 



FRIEDMANN has also (in part with SASAKI) 1 studied the decomposition, of 

 furfurpropionic acid and found that pyromucic acid with furfuracrylic 

 acid as intermediary step, was formed: 



The above-mentioned investigators are therefore of the opinion that the 

 demolition takes place in part over the a-/3-unsaturated acids and in part 

 over the 0-keto-acids or /3-alcohol acids. 



According to the investigations of DAKIN and FRIEDMANN and to the schematic 

 illustration which they give, we can consider the demolition of pheaylpropionic 

 acid as follows: 



C 6 H 5 .CH 2 .CH 2 COOH (Phenylpropionic acid) 



(Olnnamlcacid) C 6 H 6 .CH: CH.COOH 



X 

 C 6 H 5 .CO. CH 2 .COOH (Benzoylaceficacid) 



C 6 H 6 .CH (OH). CH ? .COOH 



' (Phenyl-/3-oxypropionic acid) 



C 6 H 6 .COOH 



(Benzoic acid; 



C 6 H 5 .CO .CH 3 



' ( Acetophenone) 



C 6 H 5 .COOH 



(Benzole acid) 



C 6 H 5 .CO. NH.CH 2 .COOH 



(Hippuric acid) 



Reductions may also occur and besides the examples of the reduction 

 of keto-acids to alcohol-acids, we will mention as further examples the 

 conversion, as observed by E. MEYER, 2 of nitrobenzene, CeHsNC^, or of 

 nitrophenol, HO.CeH4.NO2 into aminophenol, HO.CeH4.NH2, and also the 

 behavior of m-nitro-benzaldehyde in the animal body as mentioned below. 



Syntheses of aromatic substances with other atomic groups occur 

 frequently. To these syntheses belongs, in the first place, the conjugation 

 of benzoic acid with glycocoll to form hippuric acid, the discovery of which 

 is generally ascribed to WOHLER, but according to HEFFTER 3 more cor- 



1 Sasaki, Bioch. Zeitschr., 25; Friedmann, ibid., 35. 



2 Zeitschr. f. physiol. Chem., 46. 



1 Die AuBscheidung korperfremder Substanzen im Ham, Ergebnisse der Physiol., 

 4, 252. 



