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: S5 (Caution) / Schedule 4, Schedule 2 Appendix E, clause 3 Appendix F, clause 4; 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
Clinical data
MedlinePlus	a603020
License data	US DailyMed: Azelaic acid;
Identifiers
CompTox Dashboard (EPA)	DTXSID8021640 ;
ECHA InfoCard	100.004.246

Azelaic acid (AzA), or nonanedioic acid, is an organic compound with the formula HOOC(CH₂)₇COOH. 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. In medicine, topical formulations of AzA are used in the treatment of acne vulgaris, where they exert antimicrobial and keratolytic effects that reduce clogged hair follicles and inflammation. In plants, AzA functions as a mobile signaling molecule that primes systemic acquired resistance against pathogens by inducing the accumulation of salicylic acid. AzA also inhibits tyrosinase.