- 65 - 
Nutmeg Oil. As a constituent of this oil, Semmler^) has isolated 
long ago myristicin. At that time he gave to it the formula of a 
(I)-butenyl- (3 , 4 )-methylenedioxy- ( 5 )-methoxybenzene : 
A further examination of this body by Thorns 2), however, showed 
that instead of the butenyl -group, an allyl-group must be accepted 
The myristicin examined had the following constants: boiling point 
149,5° at 15 mm; d^go = 1,1425. By the action of alcoholic potash 
the allyl compound could be changed into the propenyl compound, 
isomyristicin, which, contrary to myristicin, is solid, and melts at 44° 
to 45°. In addition there was formed, by splitting up the methylene 
linking, a very small quantity of a phenol. Myristicin and isomyristicin 
also differ in a marked degree in their behaviour towards bromine. 
The first-named forms an oily product when submitted to the action of 
two atoms bromine, the last-named a crystalline product of the melting 
point 109°, which is identical with the one obtained by Semmler. 
If to the myristicin or isomyristicin dissolved in glacial acetic acid, and 
cooled in ice, bromine is added up to the formation of a permanent 
yellow colour, there are formed in both cases disubstituted dibromides. 
The dibromomyristicin dibromide melts at 130° and the dibromisomyristicin 
dibromide at 156°. By reducing myristicin with sodium in alcoholic 
solution, dihydromyristicin (boiling point 149° to 150° at 17 mm) is 
obtained. In this case, analogous to isosafrol and isoapiol, the methyl- 
en edioxy-group is split up, and there is formed a (i)-propyl-(5)-methoxy- 
(3)-phenol (boiling point 160° to 161° at 17 mm; dgo^ = 1,0598). 
That the oxygen atom situated in para-position towards the propyl- 
group is actually eliminated, is proved by the fact that the methyl 
ether of the phenol (boiling point 136° to I37°at i6mm; d^c|0= 1,0194) 
differs from the dihydromethyl eugenol which ought to have been 
formed if the oxygen atom situated in the meta-position had been 
^) Report October 1890, 41. 
-) Berliner Berichte 36 (1903), 3446. 
^) Semmler has also expressed himself verbally in this sense to the author. 
O — CHg 
C ^ ^2 ^ ^3 
5 
