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Record Information
Version	2.0
Creation Date	2012-08-03 14:57:54 -0600
Update Date	2015-09-13 15:15:32 -0600
Secondary Accession Numbers	ECMDB21399
Identification
Name:	Azelaic acid
Description	Azelaic acid (AZA) is a naturally occurring saturated nine-carbon dicarboxylic acid (COOH (CH2)7-COOH). It possesses a variety of biological actions both in vitro and in vivo. Interest in the biological activity of AZA arose originally out of studies of skin surface lipids and the pathogenesis of hypochromia in pityriasis versicolor infection. Later, it was shown that Pityrosporum can oxidize unsaturated fatty acids to C8-C12 dicarboxylic acids that are cornpetitive inhibitors of tyrosinase in vitro. Azelaic acid was chosen for further investigation and development of a new topical drug for treating hyperpigmentary disorders for the following reasons: it possesses a middle-range of antityrosinase activity, is inexpensive, and more soluble to be incorporated into a base cream than other dicarboxylic acids. Azelaic acid is another option for the topical treatment of mild to moderate inflammatory acne vulgaris. It offers effectiveness similar to that of other agents without the systemic side effects of oral antibiotics or the allergic sensitization of topical benzoyl peroxide and with less irritation than tretinoin. Azelaic acid is less expensive than certain other prescription acne preparations, but it is much more expensive than nonprescription benzoyl peroxide preparations. Whether it is safe and effective when used in combination with other agents is not known. (PMID: 7737781, 8961845)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa9a7368c> Close
Synonyms:	1,7-Dicarboxyheptane 1,7-Heptanedicarboxylate 1,7-Heptanedicarboxylic acid 1,9-Nonanedioate 1,9-Nonanedioic acid Anchoate Anchoic acid Azalaate Azalaic acid Azelaate Azelaicacidtech Azelainate Azelainic acid Azelate Azelex Azelic acid Emerox 1110 Emerox 1144 Emery's L-110 Finacea Finevin Heptanedicarboxylate Heptanedicarboxylic acid Lepargylate Lepargylic acid N-Nonanedioate N-nonanedioic acid Nonanedioate Nonanedioate azelaate Nonanedioate homopolymer Nonanedioic acid Nonanedioic acid azelaic acid Nonanedioic acid homopolymer Poly(azelaic anhydride) Polyazelaic anhydride Skinorem Skinoren
Chemical Formula:	C9H16O4
Weight:	Average: 188.2209 Monoisotopic: 188.104859
InChI Key:	BDJRBEYXGGNYIS-UHFFFAOYSA-N
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)
CAS number:	123-99-9
IUPAC Name:	nonanedioic acid
Traditional IUPAC Name:	azelaic acid
SMILES:	OC(=O)CCCCCCCC(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Fatty Acyls
Sub Class	Fatty acids and conjugates
Direct Parent	Medium-chain fatty acids
Alternative Parents	Dicarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	Medium-chain fatty acid Dicarboxylic acid or derivatives Carboxylic acid Carboxylic acid derivative Organic oxygen compound Organic oxide Hydrocarbon derivative Organooxygen compound Carbonyl group Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	alpha,omega-dicarboxylic acid (CHEBI:48131 ) Dicarboxylic acids (C08261 ) Dicarboxylic acids (LMFA01170054 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	106.5 °C
Experimental Properties:	Property Value Source Water Solubility: 2.4 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)] PhysProp LogP: 1.57 [HANSCH,C ET AL. (1995)] PhysProp
Predicted Properties	Property Value Source Water Solubility 2.28 g/L ALOGPS logP 1.37 ALOGPS logP 1.82 ChemAxon logS -1.9 ALOGPS pKa (Strongest Acidic) 4.15 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 74.6 Ų ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 46.54 m³·mol⁻¹ ChemAxon Polarizability 20.5 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Concentration Strain Media Growth Status Growth System Temperature Details 20± 0 uM BW25113 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Stationary Phase, glucose limited Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 37 oC PMID: 17379776 Find out more about how we convert literature concentrations.
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-MS (2 TMS) splash10-0v0r-4920000000-5a3ed693b1c4083f1f15 View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-0v0r-4920000000-5a3ed693b1c4083f1f15 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-00mk-1910000000-83ba58dac4b0698643d0 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-000f-9600000000-24638c458fa83f47c259 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-00y0-9740000000-d157d08c3a7c87244190 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) splash10-000i-0900000000-a118e433f0bd27a95b89 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) splash10-006t-9600000000-93b3a375b722791cb5c9 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) splash10-052k-9500000000-6b069f2fed947651b284 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative splash10-000i-0900000000-7980b5eadcca6ee1eadd View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative splash10-004i-0900000000-462585874f7661d40d5b View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative splash10-004j-4900000000-0f65eeeed8c8a6ff3cc9 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative splash10-0002-9300000000-d654ca3c764066f98358 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative splash10-0002-9000000000-60a08bb384f2b4cbfca8 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-000i-0900000000-7980b5eadcca6ee1eadd View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-004i-0900000000-462585874f7661d40d5b View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-004j-4900000000-0f65eeeed8c8a6ff3cc9 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-0002-9300000000-fcefbd80852c2625bc0e View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-0002-9000000000-60a08bb384f2b4cbfca8 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Linear Ion Trap , negative splash10-004i-0900000000-26216115e75cad833509 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Linear Ion Trap , negative splash10-004i-0900000000-7bef8272c481ea57a60b View in MoNA LC-MS/MS LC-MS/MS Spectrum - Linear Ion Trap , negative splash10-004i-0900000000-751bf479539d4bd2b5e1 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Linear Ion Trap , negative splash10-00di-0900000000-9a056a45b27896966bf9 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Linear Ion Trap , negative splash10-00di-0900000000-3155fd845eec8f32ce93 View in MoNA LC-MS/MS LC-MS/MS Spectrum - , negative splash10-004r-0900000000-544110f97ebc0f97e15b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00dr-0900000000-b1b7c1ab57d58a2405a8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00g3-2900000000-d0ba7fbbe987efa4c818 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-05qd-9100000000-8d65a19b998d18ad08ac View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000i-0900000000-a7edc3ac66d27685b9d1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00kr-1900000000-c56b9d972f88c58dc65b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4l-9300000000-47cbefe19a788d7f36b9 View in MoNA MS Mass Spectrum (Electron Ionization) splash10-06rx-9100000000-6db2acb47ad4c6163063 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
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Pubmed: 16566283 Fitton A, Goa KL: Azelaic acid. A review of its pharmacological properties and therapeutic efficacy in acne and hyperpigmentary skin disorders. Drugs. 1991 May;41(5):780-98. Pubmed: 1712709 Fleischer AB Jr: The evolution of azelaic acid. Cutis. 2006 Feb;77(2 Suppl):4-6. Pubmed: 16566281 Frampton JE, Wagstaff AJ: Azelaic acid 15% gel: in the treatment of papulopustular rosacea. Am J Clin Dermatol. 2004;5(1):57-64. Pubmed: 14979745 Goodman G: Managing acne vulgaris effectively. Aust Fam Physician. 2006 Sep;35(9):705-9. Pubmed: 16969442 Gupta AK, Gover MD, Nouri K, Taylor S: The treatment of melasma: a review of clinical trials. J Am Acad Dermatol. 2006 Dec;55(6):1048-65. Epub 2006 Sep 28. Pubmed: 17097400 Gupta AK, Gover MD: Azelaic acid (15% gel) in the treatment of acne rosacea. Int J Dermatol. 2007 May;46(5):533-8. Pubmed: 17472690 Halder RM, Richards GM: Management of dyschromias in ethnic skin. Dermatol Ther. 2004;17(2):151-7. Pubmed: 15113282 Halder RM, Richards GM: Topical agents used in the management of hyperpigmentation. Skin Therapy Lett. 2004 Jun-Jul;9(6):1-3. Pubmed: 15334278 Hermanns JF, Petit L, Martalo O, Pierard-Franchimont C, Cauwenbergh G, Pierard GE: Unraveling the patterns of subclinical pheomelanin-enriched facial hyperpigmentation: effect of depigmenting agents. Dermatology. 2000;201(2):118-22. Pubmed: 11053913 Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. Pubmed: 8412012 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776 Korman SH, Mandel H, Gutman A: Characteristic urine organic acid profile in peroxisomal biogenesis disorders. J Inherit Metab Dis. 2000 Jun;23(4):425-8. Pubmed: 10896310 Liao DC: Management of acne. J Fam Pract. 2003 Jan;52(1):43-51. Pubmed: 12540312 Lindow KB: Rosacea. An overview of diagnosis and management. Adv Nurse Pract. 2004 Dec;12(12):27-32. Pubmed: 15615217 Liu RH, Smith MK, Basta SA, Farmer ER: Azelaic acid in the treatment of papulopustular rosacea: a systematic review of randomized controlled trials. Arch Dermatol. 2006 Aug;142(8):1047-52. Pubmed: 16924055 Mackrides PS, Shaughnessy AF: Azelaic acid therapy for acne. Am Fam Physician. 1996 Dec;54(8):2457-9. Pubmed: 8961845 Mayer-da-Silva A, Gollnick H, Detmar M, Gassmuller J, Parry A, Muller R, Orfanos CE: Effects of azelaic acid on sebaceous gland, sebum excretion rate and keratinization pattern in human skin. An in vivo and in vitro study. Acta Derm Venereol Suppl (Stockh). 1989;143:20-30. Pubmed: 2475995 Nally JB, Berson DS: Topical therapies for rosacea. J Drugs Dermatol. 2006 Jan;5(1):23-6. Pubmed: 16468288 Nguyen, Q. H., Bui, T. P. (1995). "Azelaic acid: pharmacokinetic and pharmacodynamic properties and its therapeutic role in hyperpigmentary disorders and acne." Int J Dermatol 34:75-84. Pubmed: 7737781 Purdy S: Acne vulgaris. Clin Evid. 2005 Jun;(13):2038-59. Pubmed: 16135322 Purdy S: Acne vulgaris. Clin Evid. 2006 Jun;(15):2183-201. Pubmed: 16973084 Rocamora V, Puig L, Romani J, de Moragas JM: Amelanotic lentigo maligna melanoma: report of a case and review of the literature. Cutis. 1999 Jul;64(1):53-6. Pubmed: 10431675 Roebuck HL: Face up to rosacea. Nurse Pract. 2005 Sep;30(9):24-30, 35; quiz 36-7. Pubmed: 16151303 Russell JJ: Topical therapy for acne. Am Fam Physician. 2000 Jan 15;61(2):357-66. Pubmed: 10670502 Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411 van Zuuren EJ, Graber MA: The rigor of trials evaluating Rosacea treatments. Cutis. 2005 Mar;75(3 Suppl):13-6; discussion 33-6. Pubmed: 15810805 van Zuuren EJ, Gupta AK, Gover MD, Graber M, Hollis S: Systematic review of rosacea treatments. J Am Acad Dermatol. 2007 Jan;56(1):107-15. Epub 2006 Nov 7. Pubmed: 17190628 Webster G: Combination azelaic acid therapy for acne vulgaris. J Am Acad Dermatol. 2000 Aug;43(2 Pt 3):S47-50. Pubmed: 10898830 Wolf JE Jr: Present and future rosacea therapy. Cutis. 2005 Mar;75(3 Suppl):4-7; discussion 33-6. Pubmed: 15810803 Wolf JE Jr: The role of topical metronidazole in the treatment of rosacea. Cutis. 2004 Jan;73(1 Suppl):19-28. Pubmed: 14959942 Worret WI, Fluhr JW: [Acne therapy with topical benzoyl peroxide, antibiotics and azelaic acid] J Dtsch Dermatol Ges. 2006 Apr;4(4):293-300. Pubmed: 16638058 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:	Chen, Song; Yan, Jinlong. Synthesis of azelaic acid by chemical oxidation with oleic acid. Pige Huagong (2003), 20(6), 31-35.
Material Safety Data Sheet (MSDS)	Download (PDF)
Links
External Links:	Resource Link CHEBI ID 48131 HMDB ID HMDB00784 Pubchem Compound ID 2266 Kegg ID C08261 ChemSpider ID 2179 Wikipedia Nonanedioic acid BioCyc ID Not Available Ligand Expo AZ1