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Salicylic Acid is a small aromatic acid whose chemical name is monohydroxybenzoic acid. It is lipophilic in nature. It was first derived from the bark of Willow Tree. It derives its common name from a variety of sources related to it with a similar name, e.g., it is derived as a metabolic product of salicin (an alcoholic Beta- glycoside obtained from plants) and also it is an active metabolite produced from acetylsalicylic acid (aspirin). In nature, it occurs as clear and colourless crystals of an organic acid. The salt and ester derivatives of this compound are also widely used in organic chemistry and are known as salicylates. In plants, it occurs naturally as a growth hormone.
Structure of Salicylic Acid
Its structural formula is C6H4(OH)COOH, which can also be written as C7H6O3 in the condensed form. Its IUPAC name is 2-hydroxybenzoic acid. It contains a hydroxyl group (—OH group) attached at the ortho position with respect to the carboxylic acid functional group(—COOH group) present on the benzene ring. The molecular weight (or molar mass) of Salicylic Acid is 138.12 g/moI. The various forms in which the molecular structure of Salicylic Acid can be represented are given below:
All carbon atoms present in the benzene ring of Salicylic Acid are sp2 hybridized. Salicylic Acid forms an intramolecular hydrogen bond. In aqueous solution, Salicylic Acid, being an organic acid, dissociates to lose a proton from the carboxylic acid functional group. The resulting carboxylate ion (—COO-) undergoes intermolecular interaction with the hydrogen atom of the hydroxyl group (—OH), thereby leading to the formation of an intramolecular hydrogen bond.
The ortho hydroxy benzonic acid is known as salicylic acid, in the commerical terms. In natural sources, free salicylic acid is found in small quantities. It is found in leaves of tulips, hyacinths and voilets. It also occurs as a glycoside “Salicin” in Willow Park. This material has been used for the treatment of malaria from the middle of eighteenth century and the anti puretic effects in rehumatic fever were noted about 100 years later. Salicin has been covated to salicylic acid by hydrolyzis and oxidation:
// \ // \ // \
| || CH2OH | || CH2OH | || CO2H
| || O C5H11 | || OH—– | || OH
\\ / O ——– \\ / \\ /
Salicylic acid
But the increasing demand of this product has made its production possible by synthesis.
Salicylic acid is classified as a fine chemical and is used almost exclusively as a medicinal or as an intermediate in the manufacture of medicinals and pharmaceuticals. Actually, salicylic acid and its derivatives account for about one half the total amount of coal tar medicines produced in the United States chiefly because of the enormous sale of aspir in acetylsalicylic acid. Salicylic acid is usually manufactured by makers of phenol, the chief raw material, who engaged in general line of fine chemical manufacture. Aspirin, the chief product of which salicylic acid is the intermediate, is also commonly manufactured by the same producers, who sell it in bulk to pharmaceutical houses, which tablet and package it from sale.
Salicylic acid is the most important member of phenolic mono carboxylic acids. Its melting point 158*C (degree centigrade). It occurs in the Free State in the flowers of spiracaulmaria and as a methylester in oil of winter green, the essential oil of the ericacia, Cultheria procumbens and in many other essential oils. It’s obtained by general methods.
1. From anthranilic acid
2. O. Sulpho – O – Bromo – Benzonic acids
3. From O -Cresel from saliganing or Salicylaldehyde.
4. From phenoxides by the action of carbon diexide or carbon tetrachloride.
5. From O – bromophenol by treatment with butyl lithium inether followd by puringon to solid carbodioxide (H Gilman and C.E. Aruntzer, J Amer 1947)
It also promed when coumarin or indigo is fused with potash and when copper benzoate is distilled.
Salicylic acid, also known as O-Hydroxy benzonic and occurs in the form of its methyl ester as the chief constitutent of oil winter green from which it is isolated for theapeutic purposes. Salicylic acid finds wide use as an analgesic, antiseptic and in flavours and spices. It also acts as an ultra violet absorber. It is classified as a fine chemican and is used exclusively as a medicinal or as an intermediate in medicines. Aspirin is a widely known pain relieving medicine prepared from salicylid acid. The present production of salicylic acid is insuffinient to meet the demand.
A wide gap exists between its production and demand. The raw materials required for the manufacture of salicylic acid are phenol, caustic soda and sulphuric acid, all of wihc are available indigenously. The plant and machinery is also available indigenously and no foreign help whatsoever is needed for putting up this industry.
Salicylic acid is an old well known organic compound. It is O-hydroxy benzonic acid. It crystalizes out of water in the form of white needless and from alcohol as monoclinic prims.
Salicylic acid is used most exclusively as a medicinal and as an intermediate in the manufacture of medicinals and pharmaceuticals such as aspirin and methyl salicylate, in the manufacture of dyes and in some resin applications. Salicylic acid I.P. is used as an antiseptic and disinfeotant. It is superior to phenol. It is a strong irritant to the skin. Formulations of 10-20% salicylic acid in collodion (solution of nitrated cellulose in ether and alcohol) are used as a wait corn remover. Dusting powders containing 5% salicylic acid in combination with methanol, boric acid and starch are ised for treatment of over per spiration.
I.P grade salicylic acid should contain not less than 99.5% and not more than 101.0% of C7H6O3 calculated on dry basis. The purity of salicylic acid is analysed by titration with standardized alkali for which India pharmacopoeia gives the procedure. Technical salicylic acid assays approx 99% in purity and is generally yellowish tan to off-white in colour.
Systemic poisoning may occur when it is applied to large areas of the skin.
