Some Constituents of the Poison Ivy Plant (Rhus Toxicodendron)Syme, William Anderson
Science
Some Constituents of the Poison Ivy Plant (Rhus Toxicodendron)
Syme, William Anderson
Poison ivy
It was then thought that perhaps the oil could be converted into an
ester which might be more volatile and could be distilled out. 20 grams
of the original material were dissolved in 100 cc. of absolute alcohol
containing 3 grains of hydrochloric acid gas, and the mixture was heated
10 hours on a water-bath under a return condenser. After the heating,
the mixture had a delightful ethereal odor. The flask was corked and
left standing several weeks while other work was in progress. The ester
solution was then put in a vacuum desiccator over sulphuric acid and the
alcohol evaporated. A black, tarry, solid mass was left having the ester
odor. It was extracted with warm water and filtered from insoluble tar.
The filtrate had a green color and the ethereal odor. It was shaken out
with ether; the ether layer had a blood-red color while the water layer
was deep green. The extraction with ether was continued until the water
layer was no longer green. The combined ether extracts were evaporated
in a desiccator without heat. A black tar-like solid was left very much
like the original material, but it had the ester odor. It was partly
soluble in water and readily soluble in alcohol. The alcoholic solution
was tested on the skin and found to be not poisonous. The ester, or
mixture of esters, was not investigated further in this connection, but
was later shown to give the reactions for gallic acid and methyl
furfurol. These reactions will be referred to in connection with other
experiments.
After a few other preliminary experiments, it became evident that the
original material was a complex mixture of substances and that it would
have to be fractionated by some means and the fractions studied
separately.
A portion of the original substance was treated with 50 per cent.
alcohol and was found to be partly soluble in this medium. The solution
was filtered from insoluble tar. A portion of the yellow filtrate gave a
reddish yellow precipitate with lead acetate. The alcoholic solution was
distilled in an Anschuetze flask under diminished pressure; a yellow
liquid condensed in the arm of the flask while most of the alcohol was
collected in a bottle connected with the arm. The yellow liquid was acid
to litmus. Water was added, the solution was shaken out with ether and
the ether was evaporated. When the small residue was completely dry, it
was a yellow solid soluble in dilute alcohol and acid to litmus. The
substance was not volatile enough to justify the use of this method for
getting it.
Chlorophyll could not be removed from the original substance because the
solvents for chlorophyll such as alcohol, ether, fats, petroleum, and
carbon bisulphide dissolve large quantities of the mixture.
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