EUDESMIN AND ITS DERIVATIVES. 451 
give rise to the preferential production of either catechol 
or resorcin derivatives. This is an aspect of the chemistry 
of these trees which appeals to the authors as possessing 
great general significance, and we propose to follow up the 
investigation, and, to this end, a more detailed research 
into the constituents of Hucalyptus kinos is at present in 
progress. ‘ 
The Constitution of Eudesmin. 
The analytical data recorded in the experimental portion 
of the paper show that the substance is C22H26O¢ and that 
it contains four methoxy groups. It is levo-rotatory and 
must, therefore, have one or more asymmetric carbon atoms. 
On treatment with nitric acid a dinitro-derivative is pro- 
duced, and dichlor-, dibromo-, and diiodo eudesmins are as 
readily obtained by treating a glacial acetic acid solution 
of eudesmin with chlorine, bromine, and iodine monochloride 
respectively. These four substitution derivatives are all 
beautifully crystalline and their analyses confirm the 
formula assigned to eudesmin. The physical properties of 
these substances are similar to those of eudesmin, although, 
strange to say, the substitution of two hydrogen atoms in 
eudesmin by bromine, converts the levo-rotatory substance 
into a powerfully dextro-rotatory compound. On boiling 
with concentrated nitric acid eudesmin suffers simultaneous 
oxidation and nitration, and is converted into 4: 5— dinitro- 
veratrol (I) a substance whose constitution has been com- 
pletely proved. Moreover a quantitative determination 
showed that the amount of dinitroveratrol that can be 
obtained from a given quantity of eudesmin, is very much 
greater than that which is theoretically possible on the 
assumption that the molecule contains only one veratrol 
nucleus. Hudesmin contains, therefore,two veratrol nuclei, 
and the four methoxy groups are thus accounted for. The 
manner of connection of the veratrol nuclei to the rest of 
