F — 149 — 



passing-in of the reagent being discontinued as soon as separation ceases. 

 After being washed out with ether the precipitate is weighed. By this 

 method, Deussen discovered in Para copaiba balsam oil 5,15 p. c. and in 

 Maracaibo copaiba balsam oil 2 p. c. /^-caryophyllene. The presence of 

 the two caryophyllenes in copaiba balsam oil had already been observed 

 by us some time previously 1 ). In African copaiba balsam oil 0,87 p. c. 

 /tf-caryophyllene was found present. The low -boiling portions of West 

 Indian sandalwood oil also contained /^-caryophyllene. 



Deussen has also examined hop oil, in which distillate, in addition 

 to a-caryophyllene (the presence of which he had already ascertained 

 previously) 2 ), he determined the presence of small quantities of /?-caryo- 

 phyllene. On this occasion he also obtained a nitrosite of «-caryo- 

 phyllene. 



The author next refers to the caryophyllene which has been recovered 

 from caryophyllene dihydrochloride by Semmler and Mayer 3 ). In his 

 opinion it is doubtful whether this caryophyllene is a uniform body. 



In the same paper Deussen discusses the detection of the two double 

 bonds in a- and /^-caryophyllene. Hydrogenation by Paal's method of a 

 mixture of a- and /?-caryophyllene yielded dihydrocaryophyllene (b. p. 129 

 to 130° at 14 mm.; d 19 o 0,8898; « D — 25°; n D20 o 1,49032). The author was not 

 successful in reducing 4 ) the second double bond by hydrogen, although he 

 was able to saturate it with hydrochloric acid, bromine §c. Deussen proved 

 the existence of an ethylene-bond in a-caryophyllene nitrosite by bromina- 

 ting this body in a chloroform -solution, when 2 bromine atoms were 

 absorbed, producing a hydrobromo-nitrosochloride, m. p. 144 to 145°. 

 The fact that /^-caryophyllene nitrosite contains yet another double bond 

 is shown by the generation of /?-hydrochloro-caryophyllene-nitrosite (m. p. 

 137°) when dry hydrochloric acid gas is passed into the ethereal solution 

 of the /3-nitrosite. This compound occurs in the form of deep blue needles. 

 Its sp. rot. is extraordinarily high, viz., +930,4°. ^-Caryophyllene nitrosite 

 also possesses a very high rotation; the values +102,95 and +162,49°, 

 given for this body by Kremers and by Deussen -Lewinsohn have been 

 erroneously calculated, the correct figures being +1029,5 and +1626,0°. 

 Deussen and Vielitz found [« D ] + 1661,1° (0,1713 °/o solution in ligroin). 



According to Haarmann 5 ) the glycol-like compound C15H22O4 which 

 was obtained by Deussen when oxidising caryophyllene with potassium 

 permanganate 6 ), has the structure C14H22O4. Deussen has once again 

 submitted this body to combustion with the result that he again found 



!) Report October 1910, 185. 



2 ) Comp. Report October 1911, 55. 



3 ) Berl. Berichte 43 (1910), 3451. Report April 1911, 171. 

 *) Comp. p. 150. 



6 ) Comp. Report October 1909, 177. 

 «) Comp. Report April 1909, 124. 



