Salicylic Acid
Title: Salicylic Acid
CAS Registry Number: 69-72-7
CAS Name: 2-Hydroxybenzoic acid
Trademarks: Acnisal (Euroderma); Duofilm (Schering); Duoplant (Schering); Keralyt (BMS); Occlusal (Euroderma); Verrugon (Pickles)
Molecular Formula: C7H6O3
Molecular Weight: 138.12
Percent Composition: C 60.87%, H 4.38%, O 34.75%
Literature References: Occurs in the form of esters in several plants, notably in wintergreen leaves and the bark of sweet birch. Manuf by heating sodium phenolate with carbon dioxide under pressure: W. L. Faith et al., Industrial Chemicals (Wiley, New York, 3rd ed., 1965) pp 652-655. Review of prepns, properties, and uses of salicylic acid and derivatives: S. H. Erickson in Kirk-Othmer Encyclopedia of Chemical Technology vol. 20 (John Wiley & Sons, New York, 3rd ed., 1982) pp. 500-524. Toxicity data: K. Sota et al., J. Pharm. Soc. Jpn. 89, 1392 (1969). HPLC determn in foods: B. H. Chen, S. C. Fu, Chromatographia 41, 43 (1995). Clinical evaluation to treat warts: B. J. Bart et al., J. Am. Acad. Dermatol. 20, 74 (1989); M. E. Bender et al., Cutis 47, 199 (1991). Review of use in acne: E. Zander, S. Weisman, Clin. Ther. 14, 247 (1992). Comprehensive description: M. A. Abounassif et al., Anal. Profiles Drug Subs. Excip. 23, 421-470 (1994).
Properties: White crystals, fine needles, or fluffy white crystalline powder, mp 159°; sublimes at 76°. Gradually discolors in sunlight. d420 1.443. bp20 211°. pKa 2.98. n 1.565. Flash point (closed cup): 157°C. uv max (4 mg% in ethanol): 210, 234, 303 nm (e 8343, 5466, 3591). Soly (Wt %): water 0.20 (20°), 2.21 (80°); carbon tetrachloride 0.262 (25°); benzene 0.775 (25°); propanol 27.36 (21°); abs ethanol 34.87 (21°); acetone 396 (23°). pH of satd aq soln 2.4. Keep protected from light. LD50 i.v. in mice: 500 mg/kg (Sota).
Melting point: mp 159°
Boiling point: bp20 211°
Flash point: Flash point (closed cup): 157°C
pKa: pKa 2.98
Index of refraction: n 1.565
Absorption maximum: uv max (4 mg% in ethanol): 210, 234, 303 nm (e 8343, 5466, 3591)
Density: d420 1.443
Toxicity data: LD50 i.v. in mice: 500 mg/kg (Sota)
 
Derivative Type: Sodium salt
CAS Registry Number: 54-21-7
Additional Names: Sodium salicylate
Trademarks: Enterosalicyl (Delalande); Enterosalil (Farmabraz); Idocyl (Ferrosan); Saliglutin (Streuli)
Molecular Formula: C7H5NaO3
Molecular Weight: 160.10
Percent Composition: C 52.51%, H 3.15%, Na 14.36%, O 29.98%
Literature References: Clinical trial in rheumatoid arthritis: S. J. Preston et al., Br. J. Clin. Pharmacol. 27, 607 (1989). Toxicity data: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971).
Properties: White crystalline powder, mp 440°. Soly (g/100 cc): water 125; methanol 17. Protect from light. LD50 i.p. in rats: 780 mg/kg (Goldenthal).
Melting point: mp 440°
Toxicity data: LD50 i.p. in rats: 780 mg/kg (Goldenthal)
 
CAUTION: Ingestion of large amounts can cause vomiting, abdominal pain, increased respiration, acidosis, mental disturbances. May cause skin rashes in sensitive individuals. See: Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) pp 368-375.
Use: In manuf aspirin, methyl salicylate, and other salicylates. Coupling agent for azo dyes. Has been used as food preservative.
Therap-Cat: Keratolytic. Sodium salt as anti-inflammatory, analgesic, antipyretic.
Therap-Cat-Vet: Keratolytic.
Keywords: Keratolytic.

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