— 186 — 



author deals with the products of conversion of the neutral body C14H22O4 

 which had formed after the said body had been allowed to stand for 

 4 years. These consisted to the extent of 45% of a mixture of two acids 

 of the formula C14H22O5, melting points respectively 201 to 202° and 152°, 

 the latter acid preponderating very considerably. Boiling with highly 

 dilute sulphuric acid yielded the anhydro-acids C14H20O4, melting respecti- 

 vely at 103° and 106°. The author explains the formation of the acids 

 by a primary conversion of the compound C14H22O4, by means of traces 

 of anorganic acid, into an acid of the same formula which, in its turn, is 

 partly oxidised into two acids of the formula C14H22O5 and partly reduced 

 to C14H22O3. The neutral products which had remained behind after- 

 shaking with bicarbonate could not be distilled in vacuo without decom- 

 posing, but the indirect proof of the correctness of the theory referred 

 to above was afforded by oxidising the neutral products, as a result of 

 which two bodies were obtained, viz.: C14H22O4 (neutral glycol, m. p. 120°) 

 and C14H22O5, m. p. 201 to 202°, partly in addition to the isomerous acid, 

 m. p. 162°, which had already been obtained on a previous occasion. 



Oxidation of the acids C14H22O5, m. pts. 201 to 202° and 152°, with 

 strong nitric acid gives rise to two dibasic acids C14H20O5, m. pts. re- 

 spectively 225° and 182°. The transposition and auto-oxidation of the 

 neutral body C14H22O4 — referred to above — was accomplished artifically 

 in two phases, v\z. by heating with traces of sulphuric acid and subse- 

 quent oxidising with permanganate. The yield of the acid melting at 201 

 to 202° was 10°/o, and of that melting at 152°, 80°/ . 



A special examination showed that the original substance C14H22O4 

 was a uniform body, but the aldehyde-like body which had previously 

 been obtained from the aforesaid substance with chromic acid was found 

 to have a m. p. of 167°, and not, as previously stated, of 156 to 157°. 

 Quantitative oxidising-tests showed that caryophyllene contains about 42° 

 of an isomeride, yielding the decomposition-products described above. 



In their fourth paper on sesquiterpenes, Deussen and Philipp 1 ) deal 

 with the constitution and the chemical behaviour of the compound 

 C17H29NO2, ~ formerly described as C15H23NO2 (C15H25NO2) — which 

 was obtained from the mother-liquors in the process of preparing 

 ^-caryophyllene nitrosochloride 2 ). On the basis of the ethoxyl determination 

 according to Zeisel they come to the conclusion that the compound 

 possesses the formula C17H29NO2, which has been confirmed by combustion. 

 The genesis of this body may be explained as follows: — From the caryo- 

 phyllene nitrosochloride in solution hydrogen chloride is split off in the 

 mother liquor by the alcohol when the mixture is left standing for some 

 time, the equation being: 



*) Liebigs Annalen 374 (1910), 111. 



2 ) Ibidem 369 (1909), 46; Comp. Report April 1910, 170. 



