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
The filtrate B (p. 20) from which gallic acid was precipitated by
sulphuric acid in four fractions was saved to examine for sugar. To
remove gallic acid completely, and other vegetable matter, it was shaken
out several times with ether, and was kept at a low temperature with
salt and ice for a long time. It was left standing for several weeks,
during which time more brown matter separated out and was filtered off.
The filtrate was evaporated to a small bulk, cooled, and filtered from
crystals of potassium sulphate. The filtrate was evaporated to dryness,
the residue taken up in water and filtered through bone-black. Addition
of alcohol caused complete precipitation of potassium sulphate. The
solution then gave the above mentioned characteristic tests for
rhamnose.
All attempts to get the osazone of the sugar by the method of
Fischer[38] failed, probably on account of the small quantity of the
sugar present. The plant, it will be remembered, was originally
extracted with ether in which rhamnose is practically insoluble. The
above described tests, however, can leave no doubt as to the identity of
the sugar.
Additional evidence that the sugar is rhamnose was obtained by a method
described by Maquenne[39] as follows:
"The production of methyl furfurol in the dehydration of
isodulcite furnishes a very simple means of characterizing
this sugar in mixtures which contain it; it is sufficient,
for example, to distil 50 gm. of quercitron wood with as
much sulphuric acid and about 150 gm. of water, then to
rectify the liquid obtained in order to get several drops of
the crude furfurol, which on addition of alcohol and
concentrated sulphuric acid gives immediately the green
coloration characteristic of methyl furfurol. This procedure
is applicable to extracts as well as to entire plants, and
has the advantage that it does not require the separation of
isodulcite, the crystallization of which is often very slow
and at times impossible when it is mixed with other very
soluble substances."
The experiment was tried with the crude ether extract of the plant
according to the directions of Maquenne, and the green color with
alcohol and sulphuric acid was obtained from the thicker oily portion of
the distillate. This test can be made with hydrochloric acid[40] as well
as with sulphuric. Therefore the color test was tried with the ester
mixture prepared in one of the early experiments by boiling the original
plant material with hydrochloric acid and alcohol. Methyl furfurol was
found here also, this method indeed giving better results than that of
Maquenne.
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