3l6 



The crude oil was of a light amber colour, was somewhat uiobile, and had 

 a secondary lemon-like odour not well defined. The oil was a terpene one, and 

 consisted very largely of dextro-rotatory limonene, which had the \ery high 

 specific rotation [a]p = -\- 112-2^. The oil was somewhat insoluble in alcohol, 

 but it formed a clear solution with absolute alcohol in all proportions. Pinene 

 was probably present, but in traces only. A small amount of an ester was found, 

 but sufficient material was not available to enable either the alcohol or the acid 

 to be identified. 



The oil contained a fair amount of a constituent boiling above 270° C. — 

 e\ndently a sesquiterpene or similar body. The reactions for cadinene were not 

 satisfactorily obtained, although some of the results would seem to indicate the 

 presence of that sesquiterpene. 



The specific gravity of the ciaide oil at |j° €. = 0-8765; rotation <?„ =-f 

 74-8°; the refractive index at 16° C. = 1-4905. The saponification nimiber for 

 the esters was 8-6, equal to 3 per cent', of ester as bornyl-acetate. 



Only a small quantity of the oil could be spared for analysis, but this on 

 redistillation gave a very small amount boiling below 174° C. Between 174° and 

 177° C, 47 per cent, distilled; between 177° and 200°, 23 per cent, distilled; the 

 temperature then quickly rose to 275°, and between that and 295° C. 12 per cent, 

 distilled. 



The specific gravity of the first fraction at jf° C. = 0-8446; of the second, 

 = 0-8494; of the third, 0-9373. The rotation of the first fraction, ai,— 4-90-2°; 

 of the second, 4-91-8°; of the third, 4-29-6°. 



On again distilling the first two fractions, 28 per cent, of the total oil came 

 over betw-een 174-175° C, and 18 per cent, between 175-176° C. (cor.). The 

 specific gravity of the first fraction at 19° C. = 0-8427 ; and of the second, 0-8425. 



The rotation of the first fraction rt,, = -\- 91-4°, or specific rotation [«]]>= -H 

 108-5°; of the second, 4-94-5°, or specific rotation [a]i) = + 112-2°. The refrac- 

 tive index of the first fraction at 20° C. = 1-4783; of the second, 1-4785. 



The tetrabromide was readily prepared with both fractions, and this melted 

 at 104° C. 



From the above it is evident that the larger portion of the lower boiling 

 constituents of the oil of this tree is dextro-rotatory limonene. Dipentene does 

 not occur. From the slightly less rotation and boiling point of the first fraction, 

 it is probable that a small amount of pinene was present, but it can only occur 

 in traces. A trace of the sesquiterpene evidently still remained with the oil, as 

 indicated b)' the refractive index, although the results, taken as a whole, are very 

 close to those required for pure limonene. The specific rotations of the limonenes 

 are usually stated to be 105° to 106°, yet, besides the limonene in this oil, others 



