56 
cases the crystals were dark colored and resins appeared to be present. 
Kence the dried crystals vers stirred v;ith about 10 cc of ether cooled 
to -10° C., filtered off, washed with 10 cc. more ether, then with 5 cc. 
of nethyl alcohol cooled to -10° C. and finally dried and veis^hed a-^ain. 
The second series of washings gave parer crystals, and no further yield 
could be obtained from the filtrate. 
Cahn, Phipers, and Soam (l_7) in 1938, in briefly discussing the 
method of Takei and coworkers, stated that they had found the reactions 
involved not to be quantitative for pure rotenone and deguelin, and tliat 
tozicirol toheved partly. like deguelin and artificially swelled the re- 
sulting degj.elin contents. 
Jones (£8) in 1939, in using this raethod, renioved the al':<:ali- 
soluble material prior to the oxidation to avoid interference from toxicarol. 
This plan had also been used in tne v;crk of Martin and Tattersiield (84), 
In 1939 C-oodhij.e and Kaller (4l) developed a method for determining 
deguelin in derris and cube based on its raceraisation and the separation of 
the inactive forr. as the carbon t^^trachloride solvate. The method was as 
follovrs: 
A 50-g3i sample is extracted with chloroform in a Soxhlet 
for 7 hours. The chlorofom is renoved and the ejctract dis- 
solved in about 75 cc. of ether. This solution is extracted 
with two 15-cc. portions of 5-percent potassi^jn hydroxide 
saturated with sodium c^iloride. These portions are extracted 
with ether, sjid the combined ether layer is washed or.ce with 
1+ 10 hydrochloric acid and once with a caturated sodium chloride 
solution. The alkali- soluble extract is discarded. 
The ether is removed, the resin dissolv'^d in 40 cc. of carbon 
tetrachloride, and the rotenone solvate crystalli'^ed and separated 
.in the uaual way. The carbon tetrachloride is removed from the 
. ,. • filtrate end the residue is dissolved in 10 to 15 cc. of methanol, 
Vrnile varm. this solution is placed in a 25-cc. Erlemneyer flask 
and 10 drops of 40-percent potassium hydroxide added. The contents 
are swirled and the flask is filled w:.th warm methanol. A one- 
hole stopper carrying a funnel made from a dravm-out test tube is 
immediately inserted so that no air bubbles remain in the flack 
and some of the colorless liquid is forced up into the funnel. 
More methanol is poured in the funnel to allow for contraction on 
cooling and for evaporation. The sol\itlon is kept at about 45° C. 
for an hour to prevent se;-a ration of resin before it is racemized, 
. If deguelin is oresent, crystals soon separate, but rRComization 
is usually not complete until the material has stood overnight. 
The flisk is then cooled nt 0° 3. for 1 ho^r. The icethanol 
is then decanted through a smell filter and the residue allowed 
to drain as completely as possible. For purification the 
degi.ielin crystals are dissolved in a little chloroform, and the 
chloroform is rcol?ced by evaporating to a thick solution twice 
vitli carbon tetrachloride, i'lially, the de.^U'Slin is crystal- 
liz'jo from 5 or 10 cc. of carbon c -trs-.chloride. It is usually 
