PRODUCTS OF I'l'TREFACTION 583 



action of scarlet U and other fat stains (Stoebcr),'*'' but we have no 

 direct evidence that these substances cause similar effects in the human 

 body. 



Other Aromatic Compounds. — Skatole seems to accompany indole in small 

 amounts, Init api)arently in no constant (luantitative relation. Herter" states 

 that skatole is formed under entirely dilTerent conditions from indole, and that 

 B. call does not i)roduce skatole. It is not always present in the contents of the 

 large intestines of healthy persons, and seems to be formed later than indole. 



Indole-acetic acid appears in the normal urine in extremely mimite cpiantities, 

 and is increased in tlie same conditions as skatole. It is the mother substance of 

 urowscin, and can be found in the intestines of patients who show this substance in 

 the urine (Herter).''" Ross^* found indole-acetic acid in the urine in 21 i)er cent, 

 of normal persons, and in 48 per cent, of dementia precox cases, and obtained evi- 

 dence in favor of an endogenous origin in two cases studied especially to determine 

 this point. 



Fheuylacelic acid*^ is formed from phenylalanine on putrefaction, as also are 

 phenylpropionic and benzoic acids. Benzoic acid combines with glycine and is 

 excreted as hii)p\iric acid, and the phenylpropionic acid is excreted as />-hydroxy- 

 hippuric acid. Phenylacetic acid combines with glutamine and is excreted as 

 phenylacetylglutamine. It is but slightly toxic, 5 gm. doses in man causing slight 

 symptoms resembling alcoholic intoxication; 10 gms. not producing serious results. 



PhenoP" appears in the urine normally in very minute quantities — from 0.005 

 to 0.07 grams per day, according to various observers. These figures are undoub- 

 tedly too low, for Folin and Denis^' found the total excretion of phenols to be 

 from 0.2 to 0.4 gm. per day, the amount varying with the protein intake."- They 

 seem to come chiefly, if not entirely, from tyrosine.*' Much more is undoubtedly 

 formed in the intestines, for but a small fraction of phenol given by mouth (2 

 to 3 per cent., according to Munk) appears in the urine as a sulphuric-acid com- 

 pound; part of the rest is oxidized to hydrochinon and pyrocatechin, C6H4(OH)2, 

 and eliminated as ethereal sulphates. These sulphates, although distinctly toxic 

 are much less so than the phenol itself (Metchnikoff).*^ Contrary to prevailing 

 ideas, Folin and Denis found the greater part of the phenols to be excreted uncom- 

 bined. The largest quantities are found in the same conditions as indican ex- 

 cept, of course, in "carbolic-acid" poisoning, when the amounts may be so great 

 that practically all the sulphuric acid in the urine is in this organic combination, 

 much of the phenol under these conditions being also combined with glycuronic 

 acid.*^ This pairing is accomplished chiefly in the liver (Dubin). A small amount 

 of urinary phenol may be of endogenous origin. ^^ Rhein*® ascribes the phenol of 

 intestinal origin to the action of a specific sort of colon bacilli, B. coli phenologenes, 

 which does not produce indole but produces phenol from tyrosine, and also from 

 p-hydroxybenzoic acid which therefore may be an intermediary in tyrosine cleav- 



Blood contains small amounts of free phenols, about one-third being poly- 

 phenols, none being conjugated. In a series of pathological cases Theis and Bene- 

 dict" found from 1.87 to 7.96 mg. per 100 cc. blood, somewhat higher figures being 

 found in sarcoma and hernia cases than in other diseases. 



Cresol (chiefly paracresol), para-oxy phenyl acetic acid, and para-oxy phenyl pro- 



« Mtinch. med. Woch., 19,10 (57), 947. 

 ■"^ Jour. Biol. Chem., 1908 (4), 101; general discussion. 

 '' Jour. Biol. Chem., 1908 (4), 253. 

 ^8 Arch. Int. Med., 1913 (12), 112 and 231. 

 ^^ See Sherwin and Kennard, Jour. Biol. Chem., 1919 (40), 259. 

 ^° Literature given by Dubin, Jour. Biol. Chem., 1916 (26), 69. 

 " Jour. Biol. Chem.,^ 1915 (22), 309. 

 " Moore, Amer. .Jour. Dis. Child., 1917 (13), 15. 

 " Tsudji, Jour. Biol. Chem., 1919 (38), 13. 

 " Ann. Inst. Pasteur, 1910 (24), 755. 



" See the observations of Wohlgemuth and of Blumenthal (Biochem. Zeit- 

 schrift, 1906 (1\ 134), on the detoxication of lysol and similar poisons. 

 56 Biochem. Zeit., 1917 (84), 246. 

 " Jour. Biol. Chem., 1918 (36), 99. 



