OF ARTS AND SCIENCES. 281 



thalic acid by further oxidation. This observation proves that turmerol 

 contains a benzol ring with a methyl group attached to it. and a long 

 side-chain of six (or seven) atoms of carbon in the para position to the 

 methyl. In regard to the nature of the long side-chain we cannot 

 speak with certainty, but it has been proved that one of the atoms of 

 carbon in it is unsymmetrical, because turmerol shows circular polari- 

 zation, and that the atom of oxygen is attracted to this side-chain. 

 The earlier work of Menke and one of us further seems to indicate 

 that turmerol is an alcohol,* and that it is oxidized by cold potassic 

 permanganate with formation of acetic acid, carbonic dioxide, and two 

 acids, C n H l4 2 (turmeric acid), and C 10 II 12 O 4 ? (apoturmeric acid).f 

 We feel, however, that this earlier work needs revision before these 

 points can be considered definitely settled, as the experiments on the 

 alcoholic nature of turmerol are susceptible of an interpretation differ- 

 ent from that given to them in the paper in which they were described, 

 and the formula of apoturmeric acid is very doubtful. This revision 

 will be undertaken in this Laboratory, it is hoped, during the coming 

 year. 



Although it would be easy to assign a provisional formula to tur- 

 merol in accordance with the facts already observed, we have thought 

 it wiser to postpone doing this until further investigation has given us 

 a more secure foundation for such a formula. 



Purification and Analysis of Turmerol. 



The crude turmeric oil extracted from ground Bengal turmeric with 

 ligroine, as described in an earlier paper, $ was heated to 150° under 

 ordinary pressure for some time to remove as much as possible of the 

 ligroine, and then distilled under a pressure of 11-12 mm. according 

 to the method of Anschiitz, carrying the temperature to 200°. This 

 separated it into a small lower fraction containing ligroine, a larger 

 one consisting principally of turmerol, and a viscous retort residue 

 which formed about one half of the original oil. The large middle 

 portion was repeatedly fractioned at a pressure of 11-12 mm., which 

 divided it into a small lower fraction containing ligroine, an insignifi- 

 cant retort residue, and the principal amount boiling from 158° to 

 163° under 11-12 mm. pressure. To test the purity of this Bubstance 

 it was distilled under the same diminished pressure once more, col- 

 lecting the product in three fractions, the first and last v.tv Bmall in 



* These Proceedings, XVIII. 11. J These Proceedings, XVII. 112, 



t These Proceedings, XIX. 215. 



