Azelaic acid

Azelaic acid
Names
	Preferred IUPAC name Nonanedioic acid
	Other names Azelate
Identifiers
CAS Number	123-99-9 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1101094
ChEBI	CHEBI:48131 ;
ChEMBL	ChEMBL1238 ;
ChemSpider	2179 ;
DrugBank	DB00548 ;
ECHA InfoCard	100.004.246
EC Number	204-669-1;
Gmelin Reference	261342
IUPHAR/BPS	7484;
KEGG	D03034 ;
PubChem CID	2266;
UNII	F2VW3D43YT ;
CompTox Dashboard (EPA)	DTXSID8021640 ;
	InChI InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13) Key: BDJRBEYXGGNYIS-UHFFFAOYSA-N ; 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;
	SMILES O=C(O)CCCCCCCC(=O)O;
Properties
Chemical formula	C9H16O4
Molar mass	188.223 g·mol−1
Appearance	white solid
Density	1.443 g/mL
Melting point	109 to 111 °C (228 to 232 °F; 382 to 384 K)
Boiling point	286 °C (547 °F; 559 K) at 100 mmHg
Solubility in water	2.14 g/L
Acidity (pKa)	4.550, 5.498
Pharmacology
ATC code	D10AX03 (WHO)
Routes of; administration	Topical
	Pharmacokinetics:
Bioavailability	Very low
Biological half-life	12 h
Legal status	AU: S2 (Pharmacy medicine); US: ℞-only;
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319
Precautionary statements	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). verify (what is ?) Infobox references

Azelaic acid (AzA), or nonanedioic acid, 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 several hair and skin conditioners.^[4] AzA inhibits tyrosinase.^[5]

^ ^a ^b Sigma-Aldrich catalog Archived 9 April 2008 at the Wayback Machine
^ ^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.
^ Del Rosso, James Q. (1 February 2006). "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.
^ Cite error: The named reference Boy was invoked but never defined (see the help page).
^ Cite error: The named reference TyrosinaseInhibitor was invoked but never defined (see the help page).

[aldrich-1] Sigma-Aldrich catalog Archived 9 April 2008 at the Wayback Machine

[pka-2] 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. (1 February 2006). "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.

[Boy-4] Cite error: The named reference Boy was invoked but never defined (see the help page).

[TyrosinaseInhibitor-5] Cite error: The named reference TyrosinaseInhibitor was invoked but never defined (see the help page).

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