Sodium reduces salicylic acid in boiling amyl alcohol solution to n-pimelic acid (A.
Hydrolysis with baryta water gives acetic and salicylic acids.
Salicylo-salicylic acid O.
Salicylic Acid >>
It is a crystalline solid, which melts at 30° C. and boils at 190 8° C. Fusion with alkalis converts it into salicylic acid.
The more important of those in use to-day are carbolic acid, the perchloride and biniodide of mercury, iodoform, formalin, salicylic acid, &c. Carbolic acid is germicidal in strong solution, inhibitory in weaker ones.
Chromium oxychloride reacts violently on phenol, producing hydroquinone ether, O(C 6 H 4 OH)2; chromic acid gives phenoquinone, and potassium permanganate gives paradiphenol, oxalic acid, and some salicylic acid (R.
Among the principal varieties are those which contain carbolic acid and other ingredients of coal tar, salicylic acid, petroleum, borax, camphor, iodine, mercurial salts, sulphur and tannin.
When fused with caustic potash it yields phenol and salicylic acid.
All four mono-hydroxyxanthones are known, and are prepared by heating salicylic acid with either resorcin, pyrocatechin or hydroquinone; they are yellow crystalline solids, which act as dyestuffs.
Lactic acid and alanine were shown to be oxyand amino-propionic acids respectively; glycollic acid and glycocoll, oxyand amino-acetic acids; salicylic and benzamic acids, oxyand amino-benzoic acids.
This substance readily yields ortho-oxybenzoic acid or salicylic acid, which on nitration yields two mononitro-oxybenzoic acids.
Potassium chlorate and hydrochloric acid oxidize phenol, salicylic acid (o-oxybenzoic acid), and gallic acid ([2.3.4] trioxybenzoic acid) to tri chlorpyroracemic acid (isotrichlorglyceric acid), CC13 C(OH)2 C02H, a substance also obtained from trichloracetonitrile, CC1 3 CO CN, by hydrolysis.
Thus salicylic acid yields n-pimelic acid, [[Hooc (Ch 2) 5 Cooh]], while o-, m-, and p-cresotinic acids, C 6 H 3 (CH 3)(OH)(000H), yield isomeric methylpimelic acids.
SALICYLIC ACID (ortho-hydroxybenzoic acid), an aromatic acid, C 6 H 4 (OH)(CO 2 H), found in the free state in the buds of Spiraea Ulmaria and, as its methyl ester, in gaultheria oil and in the essential oil of Andromeda Leschenaultii.
Hofmann and Schotensack decompose a mixture of phenol (3 molecules) and sodium carbonate (4 mols.) with carbonyl chloride at 140-zoo° C. When 90% of the phenol has distilled over, the residue is dissolved and hydrochloric acid added, any phenol remaining is blown over in a current of steam, and the salicylic acid finally precipitated by hydrochloric acid.
Salicylic acid crystallizes in small colourless needles which melt at 1 55° C. It is sparingly soluble in cold water, but readily dissolves in hot.
When boiled with calcium chloride and ammonia, salicylic acid gives a precipitate of insoluble basic calcium salicylate, C 6 H 4 ‹ 0 2 i Ca, a reaction which serves to distinguish it from the isomeric metaand para-hydroxybenzoic acids.
Ethyl salicylate, C 6 H 4 (OH) CO 2 C 2 H 5j is obtained by boiling salicylic acid with alcohol and a little sulphuric acid, or by dropping an alcoholic solution of salicylic acid into 13-naphthalene sulphonic acid at a temperature of 140-150° C. (German Patent 76,574).
Phenyl salicylate, C6H4(OH) C 02C6H5, or salol, is obtained by heating salicylic acid, phenol and phosphorus oxychloride to 120-125° C.; by heating salicylic acid to 2 =0° C.; or by heating salicyl metaphosphoric acid and phenol to 140-150° C. (German Patent 85,565).
Acetyl-salicylic acid (salacetic acid), C 6 H 4 (O 000H 3) CO 2 H, is obtained by the action of acetyl chloride on the acid or its sodium salt (K.
It is used in medicine under the names aspirin, acetysal, aletodin, saletin, xaxa, &c. It has the same action as salicylic acid and salicylates, but is said to be much freer from objectionable secondary effects.
(C 6 H 4 CO 2 H) 2 is obtained by continued heating of salicylic acid and acetyl chloride to 130140° C. It is an amorphous yellow mass which is easily soluble in alcohol.
The use of salicylic acid as a food preservative, was, however, condemned in the findings of the commission appointed by the government of the United States of America, in 1904.
Salicylic acid is now never given internally, being replaced by its sodium salt, which is much cheaper, more soluble and less irritating to mucous membranes.
As an antiseptic salicylic acid is somewhat less powerful than carbolic acid, but its insolubility renders it unsuitable for general use.
Salicylic acid is a powerful irritant when inhaled or swallowed in a concentrated form, and even when much diluted it causes pain, nausea and vomiting.
It has now been established that, provided the kidneys be healthy, natural salicylic acid, sodium salicylate prepared from the natural acid, and salicin, are not cardiac depressants.
Salicylic acid is used externally for the removal of corns and similar epidermic thickenings.
Salicylism, or salicylic poisoning, occurs in a good many cases of the use of these drugs.
Salicylic aldehyde (ortho-hydroxybenzaldehyde), HO(I)ï¿½ C 6 H 4 ï¿½CHO(2), an aromatic oxyaldehyde, is a colourless liquid of boiling point 196° C. and specific gravity.
Hydrobromic acid is often used to relieve or prevent the headache and singing in the ears that may follow the administration of quinine and of salicylic acid or salicylates.
The valerianic;ester of guaiacol is known as geosote, the benzoic as benzosol,' the salicylic as guaiacolsalol, while the glycerin ether appears as guaiamar.
Of the thirteen or more other ingredients, there may specially be noticed the salicylic and benzoic acids.
Among such dyestuffs are chrysamine or flavophenine, obtained from salicylic acid and diazotized benzidine, and congo red obtained from sodium naphthionate and diazotized benzidine.
The carbon disulphide and salicylic aldehyde products have also been used as means of distinction, as has also the formation of the stilbazonium bases obtained by condensing ortho-semidines with benzil (0.
To remove these salicylic acid dissolved in flexible collodion is now generally employed.
In the remedy just mentioned the salicylic acid forms the basis; but sometimes chloride of zinc or lactic acid is added to it to make it act more quickly, and these are the adjuvants.
Most of these belong to the aromatic group of bodies, although one of them, antipyrin, belongs rather to the furfurol group. Carbolic acid has an antipyretic action, but on account of its poisonous properties it cannot be employed as an antipyretic. Salicylic acid has a strong antipyretic action, and is most commonly used in the form of its sodium salt, which is much more soluble than the acid itself.
For sodii bromidum, iodidum and salicylatum see Bromine, Iodine and Salicylic Acid respectively.
Fischer); by heating salicylic aldehyde with aniline and zinc chloride to 260° C. (R.
Salicylic acid and salicin (q.v.) share the properties common to the group of aromatic acids, which, as a group, are antiseptic without being toxic to man - a property practically unique; are unstable in the body; are antipyretic and analgesic; and diminish the excretion of urea by the kidneys.