14 _ REPORT OF SCHIMMEL & Co. OCTOBER 1914/ APRIL 1915. 
was obtained. When boiled with alcoholic potash lye, the hydrochloridé was converted 
into an oxide CsoH340, which the author calls isodicitronella oxide. It contains one ~ 
double linkage less than the original oxide. B. p. 176 to 180° (11 mm.); d= 0,9518; eS 
Np 1,49692; molecular refraction found 89,14, calculated for*C29H3,0/7 88,98. The double i. 
linkage could be saturated by heating with sodium and alcohol, resulting in dihydro- 
isodicitronella oxide, m. p. 71°. When dicitronella oxide was ozonized, chiefly neutral 
bodies were obtained after the decomposition of the ozonide. 
The oxide C2oH;,O mentioned on page 85, which Semmler and Jonas mer by 
heating citronellal with anhydrous oxalic acid, is closely related to dicitronella oxide, but — 
it differs from it inasmuch as it does not yield a solid hydrochloride and that the 
hydrogenation product is optically active, whereas the hydrogenation product of the 
natural body has no rotatory power. 
Clove Oil. In its Bulletin of April/June 1914'), the Imperial Institute in London 
describes several distillates obtained from cloves and clove leaves in the island of 
Mauritius. The properties of these oils, which agree approximately with those found 
in London, have already been reported upon in our last Report (page 47), as the 
Imperial Institute had sent us samples of the oils. We may here add that in both 
cases the yield was small, viz., 10,2 and 11,5 p.c. with cloves, and 1,62 p.c. with 
clove leaves. 
Cochlearia (Spoonwort) Oil. For spoonwort oil, obtained to the extent of 
0,007 p.c. from crushed herb, Th. A. van Pienbroek and J. Pinkhof*) give the following 
values: di50 0,959; [«], + 70,4° (3 p.c. solution in 90 p.c. alcohol); nyo 1,4914; soluble 
in 1,9 volume of 90 p.c. alcohol; not clearly soluble in 80 p.c. alcohol. The oil con- 
tained 94 p.c. of butyl mustard oil, determined with ammonia and nitrate of silver. 
When freshly distilled, the oil was yellow, but it soon became darker little by 
little, when in contact with the air. a 
About the oil from Cochlearia danica, L., see page 79 of this Report. 
An experimental cultivation of spoonwort in Austria is dealt with on page 64 of 
this Report. 
Copaiba Balsam Oil. On page 48 of our Report April 1914 we stated that in 
oil of African copaiba balsam a laevo-rotatory sesquiterpene was present, which 
differed materially from cadinene in its physical properties, but which nevertheless 
yielded cadinene hydrochloride. This sesquiterpene has been examined more closely 
by F. W. Semmler and H. Stenzel*) and has been called copaene. Purified by repeated 
distillation the sesquiterpene, upon combustion, furnished values agreeing with the 
formula Cy;H»4.° By reduction with platinum and hydrogen in absolute ethereal solution 
it formed dihydrocopaene, CisHeg (b. p. 118 to 121° at 12 mm.); oxidation with ozone 
led to a very viscid acid, the copaene ketonic acid, the silver salt of which was analysed. 
It had the formula C,;H2,O3 and formed a methyl ester of the b. p. 182 to 185° (14 mm.). 
When oxidized with permanganate of potash in aqueous acetone, copaene also yielded 
copaene ketonic acid; this acid is so strongly viscid that its physical values could not. 
be determined. Being a ketonic acid it forms a semicarbazone melting at 221°; 
1) Bull. Imp. Inst. 12 (1914), 232. — %) Pharm. Weekblad 51 (1914), 995. From a special- reprint kindly 
sent to us. — %) Berl. Berichte 47 (1914), 2555. 
