— 94 — 
esters, ketones etc. If the addition-product is saponified and carbon 
dioxide split off from the acid, there is not formed a 1,5-diketone, as 
might be expected, but (as was recently proved by Rabe and Wei- 
linger^) with the condensation -product from aceto- acetic ester and 
carvone), an isomeric bicyclic ketone alcohol of the formula QsHgQOg, 
which on reduction with zinc and hydrochloric acid yielded a mixture 
of two optically active glycols. A product prepared years ago by Gold- 
schmidt and Kisser 2) by condensation of the above-mentioned bodies 
with hydrochloric acid, in which the isopropenyl-group of the carvone- 
rest is saturated with HQ, was also examined by Rabe and Wei- 
linger^). They obtained on saponification with potassium hydrate, in 
addition to eucarvone, a body C^gHgoOg which is isomeric and possibly 
identic with the ketone alcohol mentioned above. When boiled with 
quinoline the condensation-product split up into acetone, aceto-acetic 
ester and carvacrol. 
The physiological action of camphocarbonic acid and its esters has 
recently been examined by Gottlieb^), in continuation of the previous 
work by Kobert and Lap in. Whilst camphocarbonic acid itself, and 
also its salts, do not act on the heart and the nervous system, and 
pass through the body without change, the esters show in a varying 
degree of strength the typical spasm -provoking effect of camphor, though 
not quite so strongly as the latter. The effect of the amyl ester is 
the most powerful; it was less strong with the ethyl ester, and still 
weaker with the methyl ester. The physiological activity appears to 
be proportionate to the electrolytic dissociation of the ester; the strongly 
dissociated methyl ester has the least powerful action, as contrasted 
with the strongly acting but little dissociated amyl ester. 
Oxides. 
From a trivalent alcohol of the terpene-series there can be formed, 
by splitting off water, a ketone (as with terpineol), or a double unsaturated 
alcohol, or an unsaturated oxide. The latter is the case, as Semmler^) 
has just reported, with the trivalent glycerine ^^20 ^3' which is formed 
by oxidation in the cold of dihydrocarveol with a solution of potassium 
permanganate. Wallach^) had already allowed sulphuric acid to act 
on this compound, and had thus obtained a body C-^QH-j^gO, which 
yielded two nitrogenous derivatives with hydroxylamine. 
^) Berliner Berichte 36 (1903), 225, 227. 
2) Berliner Berichte 20 (1887), 489. 
3) Berliner Berichte 36 (1903), 234. 
^) Berliner Berichte 35 (1902), 3518. 
^) Berliner Berichte 36 (1903), 764. 
^) Liebig's Annalen 277 (1893), 151, and 279 (1894), 386. 
