905. Azelaic Acid
Nomenclature
CAS number: 123-99-9
Nonanedioic acid; 1,7-heptanedicarboxylic acid; lepargylic acid; anchoic acid; Azelex (Allergan); Finaceae (Schering AG); Skinoren (Schering AG). C9H16O4; mol wt 188.22.
C 57.43%, H 8.57%, O 34.00%.
Description and references
Prepd by disruptive oxidation of ricinoleic acid: Hill, McEwen, Org. Synth. coll. vol. II, 53 (1943). Occurs in rancid oleic acid. Clinical comparison with tetracycline in acne: P. T. Bladon et al., Br. J. Dermatol. 114, 493 (1986). Review of clinical studies in hyperpigmentary disorders: A. S. Breathnach, M. Nazzaro-Porro, ibid. 111, 115-120 (1984); of pharmacology and clinical uses: M. Nazzaro-Porro, J. Am. Acad. Dermatol. 17, 1033-1041 (1987). Clinical comparison with metronidazole, q.v., in rosacea: S. Maddin, J. Am. Acad. Dermatol. 40, 961 (1999).
Properties
Monoclinic prismatic needles, mp 106.5°. Distills above 360° with partial anhydride formation. bp100 286.5°; bp50 265°; bp15 237°; bp10 225°. d4110.6 1.0291. One liter of water dissolves 1.0 g at 1.0°; 2.4 g at 20°; 8.2 g at 50°; 22 g at 65°. Freely sol in boiling water, in alcohol. 1000 g of ether dissolves 18.8 g at 11° and 26.8 g at 15°. pK1 (25°) 4.53; pK2 5.33.Derivative
Dimethyl ester.C11H20O4; mol wt 216.27.
C 61.09%, H 9.32%, O 29.59%.
Properties
Liquid, d420 1.0026. mp 3.9°. bp8 140°.Therapeutic Category
Antiacne.
Keywords
Antiacne