Azelaic acid

Azelaic acid
Skeletal formula of azelaic acid
Ball-and-stick model of the azelaic acid molecule
Names
Preferred IUPAC name
Nonanedioic acid
Identifiers
3D model (JSmol)
1101094
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.246 Edit this at Wikidata
EC Number
  • 204-669-1
261342
KEGG
UNII
  • InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13) checkY
    Key: BDJRBEYXGGNYIS-UHFFFAOYSA-N checkY
  • InChI=1/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)
    Key: BDJRBEYXGGNYIS-UHFFFAOYAK
  • O=C(O)CCCCCCCC(=O)O
Properties
C9H16O4
Molar mass 188.22 g/mol
Appearance white solid
Density 1.443 g/mL
Melting point 109 to 111 °C (228 to 232 °F; 382 to 384 K)[1]
Boiling point 286 °C (547 °F; 559 K) at 100 mmHg[1]
2.14 g/L[2]
Acidity (pKa) 4.550, 5.498[2]
Pharmacology
D10AX03 (WHO)
Topical
Pharmacokinetics:
Very low
12 h
Legal status
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319
P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Azelaic acid (AzA) is an organic compound with the formula HOOC(CH2)7COOH.[3] This saturated dicarboxylic acid exists as a white powder. It is found in wheat, rye, and barley. It is a precursor to diverse industrial products including polymers and plasticizers, as well as being a component of a number of hair and skin conditioners.[4] AzA inhibits tyrosinase.[5]

  1. ^ a b Sigma-Aldrich catalog Archived April 9, 2008, at the Wayback Machine
  2. ^ a b Bretti, C.; Crea, F.; Foti, C.; Sammartano, S. (2006). "Solubility and Activity Coefficients of Acidic and Basic Nonelectrolytes in Aqueous Salt Solutions. 2. Solubility and Activity Coefficients of Suberic, Azelaic, and Sebacic Acids in NaCl(aq), (CH3)4NCl(aq), and (C2H5)4NI(aq) at Different Ionic Strengths and at t = 25 °C". J. Chem. Eng. Data. 51 (5): 1660–1667. doi:10.1021/je060132t.
  3. ^ Del Rosso, James Q. (2006-02-01). "The use of topical azelaic acid for common skin disorders other than inflammatory rosacea". Cutis. 77 (2 Suppl): 22–24. ISSN 0011-4162. PMID 16566285.
  4. ^ Cite error: The named reference Boy was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference TyrosinaseInhibitor was invoked but never defined (see the help page).