salicylic acid


salicylic acid
Chem., Pharm.
a white, crystalline, very slightly water-soluble powder, C7H6O3, prepared from salicin or phenol: used as a food preservative, in the manufacture of aspirin, and in medicine chiefly in the form of a salicylate as a remedy for rheumatic and gouty conditions.
[1830-40]

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White, crystalline solid organic compound used chiefly to make aspirin and other pharmaceutical products, including methyl salicylate (oil of wintergreen, for medicines and flavourings), phenyl salicylate (for sunburn creams and pill coatings), and salicylanilide (a cutaneous fungicide).

Its molecular structure, with the formula C6H4(OH)COOH, consists of a six-membered aromatic ring (see aromatic compound) having a hydroxyl group (―OH) and a carboxyl group (―COOH) bonded to adjacent carbon atoms; as such, it is both a phenol and a carboxylic acid. It and certain derivatives occur naturally in some plants, particularly species of Spiraea and Salix (willow). Large amounts are used in producing certain dyes.

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also called  ortho-hydroxybenzoic acid 
 a white, crystalline solid that is used chiefly in the preparation of aspirin and other pharmaceutical products. The free acid occurs naturally in small amounts in many plants, particularly the various species of Spiraea (spirea). The methyl ester also occurs widely in nature; it is the chief constituent of oil of wintergreen. Salicylic acid was first prepared by the Italian chemist Raffaele Piria in 1838 from salicylaldehyde. In 1860 the German chemists Hermann Kolbe (Kolbe, Hermann) and Eduard Lautemann discovered a synthesis based on phenol and carbon dioxide. Today the compound is made from dry sodium phenoxide (sodium phenolate) and carbon dioxide, followed by treatment with acid.

      Most salicylic acid produced commercially is treated with acetic anhydride for the preparation of aspirin.

      Salicylic acid esterified with methanol in the presence of an acid catalyst gives methyl salicylate, synthetic oil of wintergreen, which is used as a flavouring agent. Treatment of salicylic acid with phenol gives phenyl salicylate, which is used for sunburn creams and enteric-coated pills and to make salicylanilide for use as a fungicide and mildew preventive. Salicylic acid is a component of preparations used to combat warts, corns, calluses, and various skin diseases. The sodium salt is used in the manufacture of certain classes of dyes (dye).

      Pure salicylic acid crystallizes from hot water in the form of white needles, which sublime without decomposition at temperatures up to 155 °C (311 °F) and melt at 159 °C (318 °F). Above 200 °C (392 °F), the acid decomposes to phenol and carbon dioxide.

William H. Brown
 

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Universalium. 2010.

Look at other dictionaries:

  • Salicylic acid — Salicylic acid …   Wikipedia

  • salicylic acid — [sal΄ə sil′ik] n. [salicyl (radical of the acid) < Fr salicyle < L salix (see SALICIN) + Fr yle, YL + IC] a white, crystalline compound, HOC6H4COOH, prepared from salicin or phenol and used in the manufacture of aspirin, as a food… …   English World dictionary

  • salicylic acid — sal′i•cyl′ic ac′id [[t]ˌsæl əˈsɪl ɪk[/t]] n. chem. pha a white crystalline substance, C7H6O3, prepared from salicin or phenol: used as a food preservative and in the manufacture of aspirin Etymology: 1830–40; < F salicyl the diatomic radical… …   From formal English to slang

  • salicylic acid — salicilo rūgštis statusas T sritis chemija formulė HOC₆H₄COOH atitikmenys: angl. salicylic acid rus. салициловая кислота ryšiai: sinonimas – 2 hidroksibenzenkarboksirūgštis …   Chemijos terminų aiškinamasis žodynas

  • salicylic acid — A component of aspirin (acetylsalicylic acid), derived from salicin and made synthetically; used externally as a keratolytic agent, antiseptic, and fungicide. * * * sal·i·cyl·ic acid .sal ə .sil ik n a crystalline phenolic acid C7H6O3 that is …   Medical dictionary

  • salicylic acid — noun A white crystalline organic acid, 2 hydroxybenzoic acid, CH(OH)(COOH), used in the production of aspirin and other industrial chemicals …   Wiktionary

  • SALICYLIC ACID —    produced in commercial quantities from carbolic acid; is a white crystalline powder, soluble in water, odourless, of a sweetish acid taste; largely used as an external antiseptic, and internally in the form of salicylate of sodium as a… …   The Nuttall Encyclopaedia

  • salicylic acid — noun Etymology: French salicylique, from salicyle, the group HOC6H4CO, from salicine salicin + yle yl Date: 1840 a crystalline phenolic acid C7H6O3 that is used medicinally especially as an exfoliant and in the form of salts and other derivatives …   New Collegiate Dictionary

  • salicylic acid — white crystalline acid made of from salicin or phenol used in the production of aspirin and dyes and food preservatives …   English contemporary dictionary

  • salicylic acid — [ˌsalɪ sɪlɪk] noun Chemistry a bitter compound present in certain plants, used as a fungicide and in the manufacture of aspirin and dyestuffs. Origin C19: from Fr. salicyle, the radical of the acid, from L. salix, salic willow , + ic …   English new terms dictionary


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