- 4 8 — 



on a commercial scale, about 7O°/ d-linalool was obtained. It may 

 therefore be considered that the linalool content of coriander oil is 

 from 60 to 70 /o- 



In the hydrocarbon fractions, amounting to about 2O°/ of the 

 oil, the following bodies were found present: i-a-pinene, identified by 

 the nitrolbenzylamine, m. p. 123 to 124 , and i-pinonic acid, m. p. 104 

 to 105 ; d-a-pinene, identified by d-pinonic acid, m. p. 68,5 to 70 

 (Hd -|- 89,40°), /?-pinene, identified by oxidation with permanganate 

 solution into nopinic acid, m. p. 125 to 12 7 . Furthermore we isolated 

 p-cymene showing the following constants: d^o 0,8601, «d ± o°, 

 n D20° I >48565. When oxidised with permanganate, the cymol yielded 

 p-hydroxi-w propylbenzoic acid, m. p. 155 to 156 °. Dipentene, 

 which only occurs in the oil in very small proportions, could be 

 identified through the tetrabromide, m. p. 123 to 124°. There were also 

 indications of the occurrence of terpinolene and phellandrene, 

 but they were insufficient to afford absolute certainty of the presence 

 of these terpenes. A considerable part of the hydrocarbon fractions 

 consisted of terpinene, including a- as well as y-terpinene. Treatment 

 with nitrous acid of the fractions boiling at 179 to 180° resulted 

 in the formation of terpinene nitrosite, m. p. 154 to 155°. With 

 hydrochloric acid gas the same fraction yielded a large proportion of 

 terpinene dihydrochloride, m. p. 51 to 52°. The dihydrobromide 

 melted at 58,5 to 59,5°. The hydrochloride, when treated with alkali 

 by Wallach's method 1 ), was readily converted into terpinenol. When 

 the terpinene fractions were oxidised with diluted solution of per- 

 manganate of potassium, the erythritol, m. p. 235 to 236° was formed 

 (which, according to Wallach's researches 2 ) is derived from ^-terpinene) 

 and likewise inactive a, a'- dihydroxy - a, a'- methyl zwpropyladipic acid, 

 m. p. 1 89°. This acid is a derivative of a -terpinene. It was thus 

 evident that both forms of terpinene occur in the natural state. 

 The presence of a-terpinene can readily be shown by means of the nitro- 

 site test, and in some cases this body has already actually been dis- 

 covered in essential oils, but until the more recent researches of Wallach 

 the conditions of isomerism of this terpene were by no means clear. 

 These researches, however, have made it possible to recognize the 

 various terpinenes in mixtures and to identify them positively. 



In the portions of coriander oil of which the boiling points lie above 

 that of linalool, higher aliphatic aldehydes were found, chiefly decylic 

 aldehyde, also geraniol, borneol and the acetic esters of these 

 alcohols. The decylic aldehyde was identified more clearly by con- 

 version into decylic acid and into its semicarbazone, m. p. 102°. In 



*) Liebig's Annalen 350 (1906), 155; Report April 1907, 135. 

 2 ) Liebig's Annalen 362 (1908), 296; Report October 1908, 175. 



