CANNABINACE^E 117
tion No. 2 was a liquid of specific gravity -885, and may be geraniol.
fraction No. 3 was a mixture of 2 and 4. Fraction No. 4 was found to
be a sesquiterpene, to whicb the name humulene (q*v.) was given. The
same observer has also published figures for hop oils obtained from
different sources as follows :—
Specific Gravity. Rotation.
Bavarian hops, 1894 .... 0-8676 + 0° 30'
1901 .... 0-8403 - 0° 08'
Californian „ 1899 .... 0-8639 - 0° 20'
On distilling one of these oils he again obtained the " olefenic"
terpene above referred to, which is probably myrcene, and linalol,
together with an acid C 9 H 18 O 2 (probably isononylic acid) in the form of
esters. Dipentene was also detected and probably esters of geraniol.
The sesquiterpene " humulene " and the " olefenic " terpene make up more
than 80 per cent, of the oil. Schimmel & Co. have detected gurjun oil
as an adulterant of this oil.
Deussen,
1
however, has since suggested that the sesquiterpene
"humulene" is in fact «-tt-caryophyllene, with a small amount of
/?-caryophyllene.
Eabak
2
has also isolated free formic, valerianic and heptylic acids,
and also formic, acetic, octylic, nonylic, decylic, cenanthylic, and butyric
acids in the form of esters. Myrcenol was also found in the oil.
Babak considers that hop oil contains 15 to 20 per cent, of sesquiter-
penes and 20 to 40 per cent, of esters of myrcenol. This latter figure
must, however, be accepted with reserve, as the ester value is rarely
high enough to account for this quantity of esters.
Kabak gives the following table of characters of a selected number
of samples of hop oil:—
Origin.CaliforniaOregon.New York.Washington.BohemiaYear.1907
1908
1909
1907
1908
1909
1907
1908
1909
1908
1909
1907
1903
1909
Yield
per Cent.0-24
0-35
0-38
0-20
0-32
0-30
0-16
0-14
0-15
0-36
0-38
0-32
0-23
0-24
Rotation.0-823
0-836
0-839
0-8343
0-838
0-8433
0-862
0-837
0-8777
0-850
0-8464
0-855
0-824
0-861
Refractive
Index.1-4856
1-4738
1-4730
1-4802
1-4730
1-4705
1-4804
1-4756
1-4800
1-4763
1-4734
1-4905
1-4852
1-4829
Acid
No.2-3
1-7
1-8
1-6
1-0
2-8
3-6
2-1
2-5
1-0
1-5
1-5
1-0
3-0
Ester
No.44-4
45-5
46-8
57-0
50-2
56-0
61-0
47-0
51-8
51-8
53-8
52-8
52-8
55-3
Solubility
in 94
per Cent.
Alcohol.5-4 Vols.
4 ,
3-6
4-6
3-3
3
3-5
3-5
3-7
3-5 ,
3-3 ,
4 ,
6 ,
4 ,•OIL OF HEMP.
Hemp Oil.—The flowers of Cannabis sativa, the ordinary hemp,
yield about ^ per cent, of volatile oil of specific gravity about *930.
It is laevo-rotatory to the extent of about - 10° to - 12°. The oil
1
Jour. prakt. Chem., ii. 83 (1911), 483.
2
Jour. Agricult. Eesearcli Dept., Agric., Washington, 2 (1914)? 115.