1o- REPORT OF SCHIMMEL & Co. OCTOBER 1914/APRIL 1915." 
molecular refraction calculated for CisHe2O2/ 66,31, found 66,31. The dihydrocosto- : i 
lactone may be prepared from costic acid by heating with sulphuric acid of 33p.c. 
Upon hydrogenation with platinum and hydrogen, costolactone as well as dihydro- 
costolactone are converted into the same tetrahydrocostolactone Cis;Ho,O2 of the 
b. p. 198 to 202° (13 mm.); daio 1,0451; ep +33°; np 1,50510; molecular refraction 
calculated for Ci;He:O2 66,71, found 66,99. Costolactone, dihydrocostolactone and 
costic acid are therefore in genetical correlation, firstly because costic acid may be 
converted into dihydrocostolactone, and secondly costolactone and dihydrocostolactone 
into the above-mentioned tetrahydrocostolactone. Most likely they belong to the 
bicyclic terpene type of the sesquiterpene class. Costolactone is an isomeride of 
alantolactone. - 
Another fraction (b. p. 175 to 190° at 11 mm.; deio 1,0082; a) +339; np 1,51962) 
contained a doubly unsaturated, bicyclic primary sesquiterpene alcohol Cis;H.O, for 
which the authors suggest the name of costol. It reacts readily with phthalic anhydride, 
and, recovered from the hydrogen phthalate, it boiled at 169 to 171° (11 mm.); dei. 0,9830; 
@y + 13°; np 1,52000; molecular refraction calculated for Cy;HasO/2 67,67, found 67,9. 
By oxidation with chromic acid in glacial acetic solution, costol may be converted into 
an aldehyde which is characterized by a semicarbazone of the m. p. 217 to 218°. 
Theoretically the aldehyde ought to show a density of about 0,99, but in reality it has 
a specific gravity of 0,9541 at 22° (b. p. 164 to%65° at 15mm.; #) + 24°; np 1,50645); 
proving that in the course of oxidation transposition must have taken place. With 
phosphorus pentachloride, costol produced costyl chloride, Ci;HesCl of ab. p. of 160 to 
165° at 13mm., from which, by reduction with sodium and alcohol, the sesquiterpene 
isocostene was obtained: b. p. 130 to 135° (12 mm.); de10 00,9062; ap + 319; np 1,50246; 
molecular refraction calculated for Ci;Hes/2 66,15, found 66,37. Jsocostene appears to 
be a diolefinic sesquiterpene of the caryophyllene type. Costol was obtained by 
reducing the costus acid methyl ester with sodium and alcohol. 
In a fraction boiling at 160 to 175° (11 mm.) (de10 0,9235; ap +149; np 1,49994) . 
a hydrocarbon Ci;Hes (2) was present, which was given the name of aplotaxene. It 
boiled from 154 to 156° (11 mm.) and showed the low specific gravity of 0,8604 (21°). 
It was not possible, however, to obtain it quite free from oxygenous admixtures. By 
reduction with sodium and alcohol it furnished dihydroaplotaxene Cy,Hgo (b. p. 154 to 
157°; doro 0,8177) which, by means of hydrogen and platinum black, was converted into 
octohydroaplotaxene (b. p. 159 to 163° at 11 mm.; di¢ 0,7805). This body is certainly 
identical with n-heptadecane. It follows that aplotaxene is an aliphatic hydrocarbon 
with normal chain, containing four double linkings, two of which are in conjugated 
position. The costus oil fractions of the b. p. 100 to 130° (11 mm.) and 130 to 150° 
(11 mm.) contained two sesquiterpenes which were designated «- and 6-costene. 
a«-Costene boils from 122 to 126° (12 mm.); dei00,9014; e@)p—12°; np 1,49807; 
molecular refraction calculated for C1;Hos/; 66,15, found 66,37. In the process of 
hydration after Bertram and Walbaum an alcohol was formed of the b. p. 150 to 165° 
(14,5 mm.). : 
8-Costene boiled from 144 to 149° (18 mm.); dos 0,8728; ap + 6°; np 1,4905; 
molecular refraction calculated for Ci;H24/3 67,86, found 67,65. 
Finally a fraction of the b. p. 60 to 100° (11 mm.) was examined. It contained 
phellandrene (bisnitrosite, m. p. 106.to 108°), camphene (conversion into isoborneol) and 
probably a terpene alcohol CioHi. O. 
Expressed by percentage the composition of costus oil may be aperosinalee 
given as follows: — 
