May 25, 1914 
Aroma of Hops 
149 
Table VIII .—Fractionation of saponified oil of hops, showing physical properties of 
the fractions. 
Frac¬ 
tion. 
Tempera¬ 
ture. 0 
Dis¬ 
tilled 
over. 
Specific 
gravity 
at 22 °C. 
Rota¬ 
tion in 
50-mm. 
tube. 
Refrac¬ 
tion 
ND 
22° C. 
Remarks. 
1 . 
°C. 
Below 160 
Per 
cent. 
4.0 
0.8096 
Minn 
utes. 
— 21. 7 
1.4615 
A large portion of this fraction distilled below ioo° C. 
Strong irritating odor. 
2. 
160 to 165 
15-5 
.8180 
—21.7 
1.4710 
lMild aromatic, pleasant yet peculiar odor, unlike 
3 . 
165 to 170 
15-0 
.8093 
— 23.9 
1-4703 
j any of the common terpenes. ' 
4 . 
170 to 175 
2*7 
.8440 
— 28.0 
1-4750 
Pleasant odor, similar to preceding fraction. 
5 . 
175 to 185 
2.2 
.8504 
— 33*2 
1-4752 
More strongly aromatic, pleasant. 
6. 
185 to 195 
2.1 
.8767 
1.4799 
Distilled largely at 195° C. Pleasant hoplike odor. 
7 . 
195 to 205 
*9 
f 1. 4836 
Distilled uniformly. Pleasant odor, reminding of 
.9060 
—45.6 
hops. 
8 . 
205 to 215 
•7 
[1.4865 
Distilled mostly from 205 9 to 210 0 C. Odor pleas- 
antly aromatic, less fragrant. 
9 . 
215 to 245 
2. 2 
.8680 
— 45*6 
1.4818 
Temperature rose rapidly to 245 0 C. Odor less 
pleasant. 
10. .. . 
24s to 255 
2.7 
.8860 
— 23.9 
I. 4878 
Distilled uniformly. Odor strong and rather dis- 
agreeable. 
11. ,.. 
255 to 265 
5*3 
.8740 
— 2.1 
I. 4871 
Distilled uniformly. Odor strong and unpleasant. 
12.... 
265 to 275 
6.0 
.8850 
+ 10.3 
I* 4947 
Distilled largely between 265° and 270 0 C. Not 
strongly aromatic, disagreeable. 
13.... 
275 to 285 
3*2 
.8870 
+ 6.9 
I. 4948 
Disagreeable odor. 
14.... 
285 to 295 
3*8 
.8930 
+ 7-6 
1-4973 
Heavy oil with rather strong, unpleasant odor. 
is-.-. 
295 to 305 
2.8 
.8940 
+ 8.2 
I. 5000 
Heavy oil with repulsive odor. 
a Residue 305 0 and over. 
aldehyde: constituents 
The initial distillate, which had a most irritating and penetrating 
action upon the nasal passages, was tested for reducing properties. A 
silver mirror was readily produced with silver nitrate, and a decolorized 
solution of fuchsin (magenta solution) became bright red immediately. 
Lebbin’s solution (5 per cent resorcin in a solution of 40 to 50 per cent of 
sodium hydroxid) produced a deep-red color, characteristic of formalde¬ 
hyde. 
IDENTITY OF TERPENE HYDROCARBON WITH MYRCENE 
The boiling points of the second and third fractions signified a ter- 
penic character, but the odor was unlike that of the usual terpenes. An 
elementary analysis gave the following results: 
Fraction 2 .— Carbon, 87.5 per cent; hydrogen, 10.7 per cent. 
Fraction 3 .— Carbon, 86.4 per cent; hydrogen, 11.9 per cent. 
While it must be remembered that these fractions were not pure, the 
percentage of carbon and hydrogen nevertheless points to terpene com¬ 
position, since C 10 H 16 requires 88.1 per cent of carbon and 11.7 per cent 
of hydrogen. 
