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
Gallic acid is distinguished from tannic acid by tests (2) and (3). At
later stages in the work the potassium, barium, and sodium salts of
gallic acid were obtained, and finally the pure acid was made by
decomposing the sodium salt with sulphuric acid and crystallizing from
water. A portion of the acid so obtained was further purified by
dissolving in absolute alcohol and pouring into absolute ether.[20] The
melting point behavior of the acid corresponds with that of gallic acid;
it melted with decomposition at about 230 deg. For further identification,
some of the acid was converted into an ester by the following process:
it was dissolved in 80 per cent. alcohol, hydrochloric acid gas was
passed in, and the solution was heated an hour on the water bath. It was
then evaporated to a small bulk, neutralized with barium carbonate and
extracted with ether. The ether, on evaporation, left the ester which
was crystallized from water and dried in a desiccator over sulphuric
acid. The anhydrous ester agreed in melting point (156 deg. to 159 deg.) and
other properties with the ester of gallic acid described by Grimaux.[21]
For the sake of comparison, an ester was made from gallic acid obtained
from another source and the two agreed in properties. A mixture of the
two esters melted within the limits given for the ester of gallic acid.
While the tests leading to the identification of gallic acid were being
made, another series of experiments was in progress. Eleven and one-half
grams of the resin obtained from lead precipitate A by decomposition
with hydrogen sulphide were treated with 0.1 n. potassium hydroxide
added from a burette until the acid was exactly neutralized. All went
into solution. On shaking with ether, some of the potassium salt
separated out and was saved for examination. The solution became brown
on exposure to air and got darker as the work proceeded. The acid in
solution as a potassium salt was precipitated out in four fractions by
adding for each fraction one-fourth the amount of 0.1 n. sulphuric acid
required to neutralize the potassium hydroxide used. The precipitates
were filtered off and examined. The first was small in amount, gummy and
hard to filter. The solution was shaken with ether after each
precipitate had been filtered off. The succeeding precipitates were in
better condition, but were not pure. All appeared to be impure gallic
acid which had become brown by absorption of oxygen. They were saved,
however, to be tested for poison. After the last fraction had separated,
the filtrate was shaken several times with ether and saved for further
examination, which will be described under "Rhamnose." This filtrate is
designated as B.
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