Azelaic Acid

Title: Azelaic Acid
CAS Registry Number: 123-99-9
CAS Name: Nonanedioic acid
Additional Names: 1,7-heptanedicarboxylic acid; lepargylic acid; anchoic acid
Trademarks: Azelex (Allergan); Finaceae (Schering AG); Skinoren (Schering AG)
Molecular Formula: C9H16O4
Molecular Weight: 188.22
Percent Composition: C 57.43%, H 8.57%, O 34.00%
Line Formula: HOOC(CH2)7COOH
Literature 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.
Melting point: mp 106.5°
Boiling point: bp100 286.5°; bp50 265°; bp15 237°; bp10 225°
pKa: pK1 (25°) 4.53; pK2 5.33
Density: d4110.6 1.0291
Derivative Type: Dimethyl ester
Molecular Formula: C11H20O4
Molecular Weight: 216.27
Percent Composition: C 61.09%, H 9.32%, O 29.59%
Properties: Liquid, d420 1.0026. mp -3.9°. bp8 140°.
Melting point: mp -3.9°
Boiling point: bp8 140°
Density: d420 1.0026
Therap-Cat: Antiacne.
Keywords: Antiacne.
Azelastine Azelnidipine Azidamfenicol Azidocillin Azimsulfuron

Azelaic acid
Azelaic acid.png
Azelaic-acid-3D-balls.png
Identifiers
CAS number 123-99-9 YesY
PubChem 2266
ChemSpider 2179 YesY
UNII F2VW3D43YT YesY
DrugBank DB00548
KEGG D03034 YesY
ChEBI CHEBI:48131 YesY
ChEMBL CHEMBL1238 YesY
ATC code D10AX03
Jmol-3D images Image 1
Properties
Molecular formula C9H16O4
Molar mass 188.22 g mol−1
Density 1.443 g/ml
Melting point 109-111 °C[1]
Boiling point 286 °C at 100 mmHg[1]
Solubility in water 2.14 g/L[2]
Acidity (pKa) 4.550, 5.498[2]
Pharmacology
Bioavailability Very low
Routes of
administration
Topical
Elimination
half-life
12 hours
Legal status


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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Azelaic acid is an organic compound with the formula (CH2)7(CO2H)2. This saturated dicarboxylic acid exists as a white powder. It is found in wheat, rye, and barley. It is a component of a number of hair and skin conditioners.