Scientific American Supplement, No. 447, July 26, 1884 — John Shaqi
Scientific American Supplement, No. 447, July 26, 1884Various
Science
Scientific American Supplement, No. 447, July 26, 1884
Various
Science -- Periodicals
If we shake up the ether solution of bitter substance with an aqueous
solution of acetate of copper, the ether will assume a green color, and
gradually deposits a green crystalline powder, a cupreous combination
of the bitter acid. It is difficult to obtain in a pure state, as the
solutions are readily subject to slight decomposition, accompanied by a
small deposit of copper oxide. This combination is readily soluble in
alcohol, to a lesser extent in ether, and is insoluble in water.
In the course of analysis, I obtained the following figures:
C 69.4 per cent. 69.3 per cent.
H 7.95 " 7.98 "
Cu 7.20 " 7.18 "
If we suppose that the copper combines with two molecules of hop-bitter
acid, by the decomposition of one of its atoms, H, we obtain the formula
C_{50}H_{68}O_{8}Cu. This combination will contain 69.87 per cent. C,
7.91 per cent. H, and 7.33 per cent. Cu. The figures obtained do not
perfectly coincide with those calculated; it is nevertheless probable
that the formula is correct, and the combined substance analyzed was not
perfectly true.
I have already referred to the fact that solutions of hop-bitter acid,
if left standing too long, assume a yellow color, and on evaporation
leave only a yellow resinous residue. This, as its reaction shows,
evinces a complete analogy with the crystallized acid. The dark-colored
mother solution, from which the crystalline cakes of bitter acid are
obtained, contains a large proportion of this resinous compound, which
can be isolated by treatment with a weak soda-lye; this substance, like
the crystallized acid, is soluble in alkalies, and can be precipitated
from an alkaline solution by an acid. Old hops furnish far less
crystallizable acid than new hops; from some samples I have been able to
obtain only a few crystals; the remainder had been transformed into the
resinous modification.
If pure hop-bitter acid be pulverized and exposed to the atmosphere, it
soon turns yellow and the surface assumes a resinous consistency. At
the same time, a more pronounced odor of fatty acids and aldehydes is
apparent. Still more rapidly will this oxidation occur if a thin layer
of an alcoholic solution of the acid is allowed to evaporate in the air.
On the other hand, we can allow hop-oil to stand for days without its
odor being perceptibly changed; it appears to me more than probable that
the peculiar smell of old hops is due far more to the oxidation of the
bitter substance than to the oxidation of oil.
Hop-bitter acid appears to possess the character of an aldehyde and of
a weak acid; for the present I am not in a position to state its
constitution more clearly. Most of the oxidizing processes have an
energetic effect on it, forming also considerable quantities of
valerianic acid.
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