152 Report of Schimmel 8j Co. 1922. 



CH 3 OC 6 H 4 CH(NH 2 )GH(OH)CH 3 (m. p. of the acetyl derivative, 111 to 112°), iso- 

 safrole alkamine CH 2 2 :C 6 H 3 -CH(NH 2 )CH(OH)-CH 3 (m.p.79°), hydrochloride (m.p.210 

 to 215°), N-acetyHsosaf role alkamine (m.p.l56°), N-benzoylisosafrole alkamine (m.p.l39°), 

 N-dimethylisosafrole alkamine (m. p. 171 to 173°), methylisoeugenol alkamine (CH 3 0) 2 : 

 C 6 H 3 :CH(NH 2 )-CH(OH)CH 3 (m. p. 95 to 96°), hydrochloride (m.p. 222°), N-benzoate 

 (m. p. 140°), N-methylate (m. p. 90 to 91°). 



Acids, Esters, and Lactones. 



Although the butyric acid fermentation process of the carbohydrates has been in- 

 vestigated extensively and has been explained by assuming a condensation process 

 like that of acetaldol, or crotonaldehyde, the experimental ground for this theory was 

 still missing. The process was slucidated only by the investigations of C. Neuberg 

 and his collaborators. Since Neuberg and Nord 1 ) had shown that in bacterial degrad- 

 ation in the sugar series, just as in the alcoholic fermentation of sugar by means 

 of yeast, acetaldehyde is formed, Neuberg and B. Arinstein 2 ) were now able to per- 

 form successfully their investigations on the character of the butyric acid and the 

 butylic alcohol fermentations. Their experiments proved that when starch syrup is 

 fermented by Bacillus butylicus. Fitz in presence of calcium carbonate, peptone and a 

 solution of nutrient salts, 25.16 percent, butyric acid, 7.20 per cent, acetic acid, 1.7 percent, 

 butylic alcohol, and 2.23 per cent, ethyl alcohol are the result. If under the same con- 

 ditions di-sodium sulphite is added, with the object to "catch off" and eliminate the 

 intermediarily-formed acetaldehyde, the result runs as follows: — per cent, butyric 

 acid, 20.35 per cent, acetic acid, per cent, butylic alcohol, 13.47 percent, ethyl alcohol, 

 and 7.61 percent, acetaldehyde; acetic acid and ethyl alcohol may be regarded as 

 dismutation-products of acetaldehyde. These results prove that the formation of acet- 

 aldehyde depends in a certain manner on the true saccharogenic butyric fermentation 

 process. The authors found also that «-keto-7-valerolactone-/-carboxylic acid, the so- 

 called aldol of pyroracemic acid (see below under b), on fermentation with Bac. butylicus f 

 yields butyric acid in addition to some acetic acid. Pyroracemic acid being considered 

 as the intermediary stage of acetaldehyde 3 ), it may be assumed that the degradation 

 process of sugar, on butyric fermentation, passes off with pyroracemic acid as inter- 

 mediate body, this acid being condensed to the aldol and the latter split up to butyric acid. 



In the authors' opinion, both processes, that of the butyric acid fermentation and of 

 the butylalcoholic fission of sugar, can be expressed by the following rough formula?:— 



Butyric acid fermentation of sugar: 



a) C 6 H 12 6 = 2OVC0-C00H + 4H 



b) 2CH 3 COCOOH = CH 3 C(OH)-COOH 



I 

 CH 2 COCOOH 



c) C 6 H 8 6 = 2C0 2 + C 4 H 8 2 . 



Butylic alcohol fission of sugar: 



a) C 6 H 12 6 = 2OVC0-C00H + 4H 



b) 2CrVCO-COOH = CH 3 C(OH)-COOH 



ovco-cooh 



c) CeHgOe + 4H = 2C0 2 + H 2 + C 4 H 10 O. 



A ) Biochem. Ztsctir. 96 (1919), 133. Cf. Bericht (Germ, ed.) 1920, 140. — 2 ) Biochem. Ztschr. 117 (1921), 

 269. As per a special reprint kindly forwarded to us. — 3 ) Cf. p. 150 of this Report. 



