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782 URINE.
this is probably formed from the phenyl-/3-oxypropionic acid by the with-
drawal of water:
C6H5 .CH (OH) .CH2.COOH - H2 = C6H5 .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:
C4H3 O.CH2CH2COOH-»C4H3 O.CH:CH.COOH^C4H30.COOH.
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 /3-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 phenylpropionic
acid as follows:
C«H=.CH.,.CH,COOH (Phenylpropionic acid)
(Cinnamicacid) C,H,..CH: CH.COOH O.HB .CO. CH .COOH (Benzoylaceticacid)
C6
H5
.CO .CH3
( Acetophenone)
C6
H5
.CH (OH). CH2 .COOH
•
(Phenyl-£-oxypropionic acid)
C6
H5
.COOH
(Benzoic add)
C6
H6
.COOH
(Benzoic acid)
C H5
.CO. NH. CH2 .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, C6H5NO2, or of.
nitrophenol, HO.CfjH4.XO2 into aminophenol, HO.C0H4.NH2, and also the
behavior of ?n-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.
* Zeitschr. f. physiol. Chem., 40.
’ Die Ausscheidung korperfremder Substanzen im Harn, Ergebnisse der Physiol.,
4, 252.
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