- COMMERCIAL NOTES AND SCIENTIFIC INFORMATION. 39 
two double bonds were saturated, giving rise to tetrahydrocalamene, Ci5Hoeg, b. p. 123 
to 125° (10 mm.): ds 0,8951, #) +0°, np 1,48480. In the opinion of the authors this 
fact conclusively proves the bicyclical character of the sesquiterpene, and judging 
by its density they class it among those which are derivatives of naphthalene. The 
body could not be reduced with sodium and alcohol, hence the double bonds are 
not in the conjugated position. No solid hydrochloride was afforded; neither was 
any result obtained when hydrating by Bertram and Walbaum’s method. It was 
also found impossible to obtain any characteristic decomposition-products from the 
ozonide. 
The authors further obtained a fraction (b. p. 150 to 160° at 13 mm.; dogo 0,9611; 
Np 1,5098) of which the analysis pointed to the presence of a substance C;;H2O. 
This body appears to be a tertiary alcohol which readily splits off water. Water 
was invariably eliminated from it, when it was boiled with acetanhydride, or treated 
with phthalic anhydride or with zinc dust in a sealed tube. When boiled for a short 
time with concentrated formic acid the body C,;H.sO affords a hydrocarbon, calamenene, 
Ci;He2, b. p. 136 to 143° (15 mm.): ds 0,9324, %) + 6°, np 1,52317. Complete reduction 
with hydrogen in the presence of platinum black gave rise to an inactive substance, 
hexahydrocalamenene, Ci;Hes, b. p. 122 to 124° (9 mm.). 
As a result of these investigations Semmler and Spornitz regard it as highly 
improbable that the hydrocarbon C;;He. described by Thoms and Beckstrom’*) is a 
natural constituent of calamus oil; they rather suspect it to have been produced by 
the splitting-off of water from the body C;;Hs.O. On the other hand they believe the 
hydrocarbon C;;H2, to be a natural constituent of calamus oil, and not a reduction- 
product of calamenene. 
In the course of the examination of a small oil-sample the authors obtained an 
alcohol-fraction with b. p. 150 to 160° (13 mm.), dopo 0,9688, &p + 8°, np 1,51263, which 
contained a sesquiterpene alcohol Ci;H..O, of which the acetic ester boiled between 
155 and 163° (12 mm.). 
As will be observed, Semmler and Spornitz have altered the nomenclature, by 
re-naming the hydrocarbon C,;He. from calamene into calamenene and by calling 
the sesquiterpene C,;H2s., calamene. The body Ci;He,O they call calamenenol, while 
they reserve the name calamenol for the alcohol CisHe.O which still remains to be 
found. 
H. Thoms and R. Beckstr6m?) account for the fact that the outcome of the 
Semmiler-Spornitz research differs in part from their own results by the different 
origin of the oils. They point out that whereas they examined a terpene-free fraction 
of a Japanese calamus oil, Semmler and Spornitz, as stated above, experimented with 
a Russian oil. 
Thoms and Beckstrém do not consider it impossible that the hydrocarbon Cis Hoe 
may be generated from the body Cis;HaO by the elimination of water consequent 
upon the method of treatment (treatment of the fraction in question with concentrated 
aqueous solution of arsenic acid for the removal of the asarone). But in Semmler’s 
work they can find no proof that under the conditions mentioned by the authors the 
arsenic acid splits off water from the body Ci;H..O. 
Camphor Oil. During the winter the Japanese camphor oil market, considered 
as a whole, has remained unchanged. Traffic in this important raw material is made 
1) Berl. Berichte 34 (1901), 1021. — 7%) Berl. Berichte 46 (1913), 3946, 
3% 
