f 
Part IV.] Simonsen : Constituents of Indian Essential Oils. 35 
it separated in leaflets melting at 55 — 57°. In methyl alcohol solution 
OAO 
it had [a] — 86-25° 
•- -'D 
0-1007 gave O ^SOCO^ and 0 0776 H 2 O, C=64-7, H=8-5. 
CigHjgOg requires C=65-2, H=8-7 per cent. 
When this acid was oxidised in acid solution with potassium perman- 
ganate a ketone was formed which was probably Z-sabina ketone but it 
has rot up to the present been examined. 
Formation of Terpinene Dihydrochloride. 
Z-Sabinene was dissolved in excess of acetic acid and the well cooled 
solution saturated with hydrogen chloride. After standing overnight 
the solution was mixed with ice when a heavy oil separated which imme- 
diately crystallised. The solid was collected, drained on porous por- 
celain to remove a little adherent oil, and recrystallised from dilute al- 
cohol when it was obtained in beautiful leaflets which melted at 51 — 52° 
and was found to be identical with terpinene dihydrochloride obtained 
from another source. 
Formation of 1 :4 T erf in. 
Z-Sabinene (10 grammes) was mixed with dilute sulphuric acid (5 
per cent) (200cc.) and the mixture shaken on the machine for some days. 
After saturating the acid solution with ammonium sulphate, the reaction 
product was extracted with ether, the ether dried and evaporated and the 
residual oil distilled in steam to remove a little unchanged terpene and 
any terpineol which had been formed. The residue from the steam 
distillate was taken up with ether, the ether dried and evaporated 
when a viscid oil remained which rapidly solidified. After draining on 
porous porcelain it was recrystallised from a mixture of ethyl acetate 
and light petroleum when it was obtained in glistening leaflets melting at 
135 — 136°. It was identified as 1 : 4-terpin. 
0-1054 gave 0-3694 COgand 0-1094 H 2 O, C=69-7, H=ll-5 
C 10 H 20 O 2 requires C=69-8, H=ll-6per cent. 
Fractions II and III. These two fractions which consisted essen- 
tially of Z-sabinene were carefully tested for the presence of other hydro- 
carbons. Dipentene (or limonene) was absent from both fractions but 
from Fraction III (B.P.120 — 150°/ 100mm.) a small quantity of a cryst- 
alline nitrosite was obtained which after crystallisation from alcohol 
melted at 155° and was probably terpinene nitrosite which is stated to 
melt at this temperature. 
[ 146 ] 
