Du Mez—The Galenical Oleoresins. 
1051 
Fat. Schmidt 15 obtained 0.511 per cent, of a semi-solid fat 
from fresh cubebs, 0.408 per cent, from old cubebs. It is stated 
to be of ointment-like consistence, melting at 30 to 32°C. Hot 
alcohol, ether, carbon disulphide, chloroform, benzene and 
petroleum ether dissolve it readily. It is reported to be insoluble 
in cold alcohol. 
Cubebin. 16 Cubebin crystallizes from alcohol in white, odor¬ 
less needles melting at 125 to 126°C (Schmidt), 17 132°C 
(Mameli). 18 The alcoholic solution has a bitter taste. It is 
only slightly soluble in cold alcohol, quite soluble in hot alcohol, 
readily soluble in ether, chloroform, carbon disulphide, glacial 
acetic acid, fatty and volatile oils. The chloroformic solution 
is laevogyrate. Concentrated sulphuric acid dissolves it with a 
purple violet color, a reaction which is used as test for the 
identity of the cubeb fruit and the oleoresin prepared therefrom. 
Cubebin was thought by Heldt 19 to be an oxidation product 
of the sesquiterpene constituent of the volatile oil, 2 C 15 H 24 -f- 18 
O = C 30 H S0 O 9 + 9 H 2 0. Later work on the determination of 
its structure, however, has shown this theory to be untenable. 
The following structural formulas have been brought forward to 
represent its composition. 
HC 
HC 
CCH=CH CH.OH 
/\, 
CH 
C 
c v«. 
Jr 
Formula of Pomeranz 
( 20 ) 
19 Ibid. 
18 Monheim, Buchner’s Repert. f, d. Pharm. (1833), 44, p. 199; Cassola, 
Journ. d. Chim. Med. (1834), 10, p. 685; Soubeiran and Capitaine, Journ. 
de Pharm. et de Chim. (1839), 25, p. 355; Ann. d. Chem. (1840), 34, p. 323; 
Steer, Buchner’s Repert. f. d. Pharm. (1838), 11, p. 88; Ibid. (1840), 20, p. 
119; Schuck, Buchner’s n. Repert. f. d. Pharm. (1852), 1, p. 213; Engel- 
hardt, Ibid. (1854), 3, p. 1; Bernatzik, Ibid. (1865), 14, p. 97; Schmidt, 
Arch. d. Pharm. (1870), 191, p. 1; Weidel, Wien. Akad. Ber. (1878), 74, 
p. 377. 
1T l. c. 
18 Chem. Ztg. (1908), 32, p. 46. 
19 Arch, der Pharm. (1870), 191, p. 23. 
20 Monatsch. f. Chem. (1888), 9, p. 323. 
