150 Report of Schimmel § Co. 1922. 



of the alcohols, however, being a purely chemical reaction depends in its speed on the 

 concentration of the alcohol. 



A new optically active <x,/?-ketonic alcohol C 9 Hi O 2 composed of equal molecules 

 of acetaldehyde and benzaldehyde and possessing the constitution C 6 H 6 CO • CHOH • CH 3 

 or C 6 H 5 CHOHCOCH3 has been obtained by C. Neuberg and }. Hirsch 1 ) by means of 

 an enzymatic process. The authors proved with this synthesis, where two, aldehydes 

 unite by a fermentation process and form a ketone, that an enzyme exists capable of 

 linking straight-lined carbon chains. This new enzyme connecting carbon with carbon, 

 was termed "carboligase". However, a direct union of acetaldehyde and benzaldehyde 

 by fermentation could not be effected, but it succeeded when the biological predecessor, 

 carboxyacetaldehyde, i. e. pyruvic acid, or also sugar, was employed. The authors 

 proceeded in the following manner: — A mixture of sugar, or pyruvic acid, yeast (or 

 the juice of macerated yeast), and benzaldehyde was left to stand for three days and 

 was then filtered and extracted with ether, after the fermentation had come to an end. 

 The residue of the ether was a light yellow oil with a pungent odour reminding of 

 benzyl alcohol (b. p. 102 to 156° at 15 mm.) which gave a strong reaction with sodium 

 nitroprusside and which precipitated instantaneously cuprous oxide from cold Fehling's 

 solution. 0.1 ccm. of the oil dissolved in 10 ccm. of absolute alcohol, showed a rotation 

 of —0.75° in a 100 mm. tube. On standing at the air, signs of decomposition, such 

 as a smell of benzaldehyde, were noticed. The authors were unable to obtain a uniform 

 fraction boiling within narrower limits, in spite of repeated distillation, but they were 

 successful in preparing various derivatives of the product: — phenylhydrazone, m. p. 96°; 

 semicarbazone, m. p. 189°; thiosemicarbazone, m. p. 204 to 205°; p-nitrophenylosazone, 

 m. p. 264 to 265° — which served for identifying the product and as a proof for the 

 correctness of the formulae given above. 



It could not be elucidated in which manner the fermentation of sugar or of pyro- 

 racemic acid passes off in presence of benzaldehyde. The authors leave it open for 

 discussion whether a specially reactive fornT of acetaldehyde is formed by the scission 

 of pyroracemic acid with carboxylase, which unites with benzaldehyde, or whether the 

 biological condensation starts already with benzaldehyde and pyroracemic acid. 



Phenols and Phenol Ethers. 



Carvncrol. — According to Gibbs and Phillips 2 ), a good yield of carvacrol is obtained 

 from ^-cymene sulphonic acid only when the process is carried on in an autoclave. 

 With reference to this statement, A. W. Hixson and R. H. Mc.Kee 3 ) claim to have 

 obtained a good yield- (76 per cent.) of carvacrol from p-cymene sulphonic acid when 

 working at ordinary pressure. The carvacrol of Gibbs and Phillips (prepared with or 

 without pressure) is said to contain 6 to 8 per cent, of thymol, which would escape 

 detection by the method of analysis used by Gibbs and Phillips. 



D. C. L. Sherk 4 ) has published a thesis entitled, Thymol and carvacrol problems, of 

 which we discussed some details in our last Bericht (Germ, ed.) 1921, p. 119. In 

 addition to the compounds mentioned there the author prepared the alkali salts of 

 nitrosocarvacrol and nitrosothymol by dissolving the nitrosophenols in the theoretical 



x ) Biochem. Ztschr. 115 (1921), 282. As per a special copy kindly forwarded to us. — 2 ) Cf. Bericht 

 (Germ, ed.) 1920, 147. 3 ) Journ. ind. eng. Chem. 12 (1920), 296. — 4 ) Thesis (Fritzsche Bros. Fellow), 



Madison, Wis., 1920. From a copy kindly forwarded to us. 



