— 74 — 



determine by cultivation experiments whether external conditions, such 

 as mode of cultivation, climate etc., were of influence in causing this 

 difference. The results of his experiments, which have now been 

 published 1 ), are interesting in several respects. Of the French seed, 

 which was supplied by us, a portion was immediately distilled (sample 

 no. i), while the rest was sown at Dahlem in Germany in the spring 

 of 1904. The fruit of this, gathered in the autumn of 1905, was 

 distilled in February 1906 (sample no. 2). As the following table 

 shows, the differences in the composition of the two oils are only 

 slight, but it must be borne in mind that important influences would 

 only be perceptible after repeated cultivation: — 



Sample i Sample 2 



d 15° 1 »o3 T >°7 



Terpene content about 5 % about 5 °/ 



Acid mixture (chiefly palmitic acid) . . . 0,1 746% 0*876 °/ 



Phenols 0,184% 2,51 °/ 



Principal fractions at 15 mm. pressure 



a) 160 to 165 28% 25% 



b) 165 to 170 .-.,;,, 47% 35% 



The determinations of carbon, hydrogen, and methoxyl showed 

 that in both oils the principal fractions possessed approximately the 

 same composition. In all the four fractions the presence of apiol could 

 be detected, and by brominating, myristicin was found in the form of 

 dibromo myristicin dibromide, while the high values obtained for the 

 methoxyl content further indicated the presence of a phenol ether still 

 richer in methoxyl. In order to determine the character of the last- 

 named body, the fraction was first treated with alcoholic potash and 

 afterwards reduced with sodium in alcoholic solution. But neither from 

 the hydrated phenol which had been obtained by this process (b. p. 156 

 to 1 6o° at 1 7 mm. pressure) nor from its methylation product (b. p. 1 60 

 to 165 at 19 mm. pressure) could any solid bodies be isolated by 

 cooling. Both substances, however, yielded a nitro product melting at 

 65 , which proved to be identical with the 1 -propyl 2, 3, 5-trimethoxy 

 4-nitrobenzene already previously obtained from apiol 2 ). Oxidation of 

 the fractions with permanganate, however, threw some light upon the 

 character of the phenol ether in question, for besides yielding myristicinic 

 and apiolic acids, this process resulted in the formation, as the principal 

 product, of 2, 3,4, 5-tetramethoxy benzene carboxylic acid-i, which had 

 already been previously obtained by Bignami and Testoni 3 ) by the 

 oxidation of a fraction of parsley oil. Finally Thorns succeeded, by 

 cooling the fractions with solid carbonic acid, in isolating the phenol- 

 ether itself in solid form. Among its constants the following may be 



x ) Berl. Berichte 41 (1908), 2753. 



2 ) Berl. Berichte 36 (1903), 17 14; Report October 1903, 100. 



8 ) Gazz. chim. ital. 30 (1900), I. 240; Report October 1900, 48. 



