A New or Improved Manufacture of Guaiacol Compounds.
Year: 1897

page_text: Date of Application, 30th Mar., 1897-Accepted, 13th Nov., 1897
COMPLETE SPECIFICATION,
A New or Improved Manufacture of Guaiacol Compounds.
I, GEORGE LUDWIG SCHAEFER, of 105 North 11th Street, in the City of
Brooklyn, County of Kings, and State of New York, United States of America,
Chemist, do hereby declare the nature of my invention for Improvements in
Chemical Compounds, and in what manner the same is to be performed, to be
particularly described and ascertained in and by the following statement:-
This invention relates to a new chemical compound, intended more particularly
for medicinal purposes, and it consists particularly in a compound wherein the
chemical guaiacol forms a considerable portion, and is compounded or united with
an alkaloid, the compound being intended for internal application and is free
of the objectionable and practically all of the dangerous properties of the guaiacol.
Guaiacol, as is known, is a substance sparingly soluble in water, has a charac-
teristic odor, and very caustic properties. The objectionable odor and caustic offcots
have heretofore limited the use of the substance as a medicine to small or
insignificant amounts or doses.
To obviate and overcome these objections to the substance, guaiacol, and to
render the same susceptible of being administered in large amounts, I form a
union of guaiacol and sulphuric acid, which compound possesses the following
chemical formula:
он
CH, OCH,
HSO
The compound so formed I term "guaiacol-sulphonic-acid." The material is
prepared by heating guaiacol with concentrated sulphuric acid, on a water bath,
diluting the product with water and then neutralizing the mixture with a carbonate
or hydrate such as barium, calcium, or potassium carbonate or hydrate, whereby
barium, calcium or potassium guaiacol sulphonate is formed. These salts are
soluble in water and may be purified by recrystallization, and from the purified
salts "guaiacol sulphonic acid" is obtained by the addition of sulphuric or other
mineral acid.
or
"Guaiacol sulphonic acid" possesses the characteristic medicinal properties
but is free from tho caustic effects or odor of guaiacol. In order to render the
same susceptible of being administered in considerable quantity, I have formed a
substance wherein the saine is compounded with and neutralized by an alkaloid.
This compound can be produced either by double decomposition
by diluting the acid and dissolving the alkaloid therein. The Com-
pounds thus produced, I have found to be free from the objectionable
odor and caustic properties of guaiacol, and has proven a very valuable and power-
ful medicine or remedy, possessing the valued properties of both guaiacol and
the alkaloid.
Tho alkaloid which I preferably employ is quinine, making either the neutral
or acid salt of the guaiacol sulphonic acid,
[Price 8d.1

page_text: The alkaloid of quinine to produce a neutral salt is mixed with the guaiacol
sulphonic acid in about the proportions of two hundred and four (204) parts of
the acid to three hundred and twenty-four (24) parts of the alkaloid, by weight.
This compound which is termed guaiacol sulphonate of quinine," possesses the
following chemical formula:
(CH,O,CHLHSO)CHNO,
The acid salt of quinine is made with the "guaiacol sulphonic acid". in about
the proportion of four hundred and eight (408) parts of the acid to three hundred
and twenty-four (324) parts of the alkaloid. This compound is termed "guaiacol-
bi-sulphonate of quinine" and possesses the following chemical formula:
(CH,O,CH,HSO)2C„INO
1
Guaiacol sulphonate of quinine is a neutral salt sparingly soluble in cold water,
soluble in boiling water, readily soluble in alcohol and diluted acids.
Guaiacol bi-sulphonate of quinino is an acid salt very soluble in cold water and
alcohol and possessing hygroscopic properties.
In these compounds the odors and caustic properties of guaiacol, as stated, are
eliminated and they possess both the antipyretic properties of quinine and the
antiseptic and antifebrile properties of guaiacol, and admit of the administration
of guaiacol in quantities much larger than has heretofore been possible.
I have also found that similar compounds can he prepared from union of
guaiacol sulphonic acid with ciuchonidia, cinchonine and quinidine, which possess
similar chemical and medicinal properties. These and the foregoing quinine salts
may be prepared either directly from the dilute guaiacol sulphonic acid, by
dissolving the various alkaloids therein, or by double decomposition between a
salt of the alkaloid, such as the sulphate, and either calcium barium or potassium
guaiacol sulphonate. The solutions are evaporated over a water bath or in vacuo
and yield the salts above described.
While I have specified certain alkaloids, I desire it understood that the inven-
tion is not limited to such, as other alkaloids or bases may be used with beneficial
effect. I also desire it understood that the stated proportions may be varied.
Having now particularly described and ascertained the nature of my said
invention and in what manner the same is to be performed, I declare that what
I claim is:-
:―
1. A chemical compound being a salt, comprising an alkaloid base (such as
quinino) and guaiacol sulphonic acid.
2. A chemical compound being a salt, comprising quinine and guaiacol
Bulphonic acid.
3. A compound for medicinal purposes consisting of salts of guaiacol sulphonic
acid comprising guaiacol sulphonic acid and an alkaloid or base.
Dated this 30th day of March 1897.