- 136 - 



On further oxidation with chromic acid the glycerol does not yield 

 the ketolactone C 10 H 16 3 melting at 62 ° which is obtained from 

 a-terpineol. In the further course of the examination, Wallach and 

 Boedecker 1 ) were then able to demonstrate that the above-mentioned 

 terpineol of cardamom and sweet marjoram oils, and the alcohol which 

 is formed by shaking sabinene with sulphuric acid (see page 140), 

 are identical with the terpineol which is obtained by the action of 

 aqueous alkali on terpinene dihydrochloride (see above). Wallach 

 designates it as terpinenol, to distinguish it from the known terpineols, 

 and in order to give expression to the relationship between the body 

 and terpinene. All terpinenols of various origin yield with hydrohalogen 

 terpinene hydrohalogenides, with dilute sulphuric acid the new terpin 

 melting at 13 7 , and when treated with oxidising agents the same 

 oxidation products. The glycerol C 10 H 17 (OH) 3 which, in addition to 

 a not yet examined ketone, is formed on treatment with potassium 

 permanganate, is more difficultly soluble in chloroform, and crystallises 

 in a manner different from that of the isomeride prepared from a- 

 terpineol. When distilled with aqueous hydrochloric acid it yields 

 carvenone, besides cymene. The oxidation products of the two isomeric 

 glycerols show a distinct difference. When the glycerol from the 

 terpineol is oxidised, an acid C 10 H 18 6 is obtained, which occurs in 

 two modifications (m. p. 205 to 206 and 188 to 189 respectively). 

 Both are readily converted in crystallised lactones C 10 H 14 4 , volatile 

 with steam, if they are heated by themselves or in solution, under 

 the influence of suitable reagents. The one corresponding to the higher- 

 melting acid melts at 63 to 64 , the one which corresponds to the 

 lower-melting acid, at 72 to 73° The former has nearly the same 

 melting point as the ketolactone C 10 H 16 3 from the glycerol from 

 a-terpineol. Now, as the detection of the latter in oil of sweet marjoram 

 by Biltz is based solely upon an oxidation-product of the m. p. 6i°, 

 which was obtained in a small quantity, might possibly not have been 

 quite pure and for that reason have had a low r er melting point, and 

 which moreover was not analysed, — it is clear that Semmler's 

 opinion that the presence of a-terpineol in oil of sweet marjoram were 

 established beyond doubt, must be accepted only with caution. If the 

 fraction of oil of sweet marjoram which contains the terpineol is shaken 

 with sulphuric acid, there is formed ordinary cis-terpin hydrate, and 

 terpinene terpin melting at 13 7 . For the present Wallach gives to 

 terpinenol the following formula: 



,CH — CH 2 v 

 CH 3 — C<f )C(OH) . C 3 H 7 



\ch -ch/ 



x ) Berl. Berichte 40 (1907), 596. 



