Azelaic acid
| Azelaic acid | |
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nonanedioic acid |
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| Identifiers | |
| CAS number | 123-99-9  |
| PubChem | 2266 |
| ChemSpider | 2179 |
| UNII | F2VW3D43YT |
| DrugBank | APRD00812 |
| KEGG | D03034 |
| ChEBI | CHEBI:48131 |
| ChEMBL | CHEMBL1238 |
| ATC code | D10 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C9H16O4 |
| Molar mass | 188.22 g mol−1 |
| 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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 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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.
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[edit] Production
Azelaic acid is industrially produced by the ozonolysis of oleic acid. The side product is nonanoic acid. It is produced naturally by Malassezia furfur (also known as Pityrosporum ovale), a yeast that lives on normal skin. The bacterial degradation of nonanoic acid gives azelaic acid.
[edit] Biological function
In plants, azelaic acid serves as a "distress flare" involved in defense responses after infection.[3] It serves as a signal that induces the accumulation of salicylic acid, an important component of a plant's defensive response.[4]
[edit] Applications
[edit]
Esters of this dicarboxylic acid find applications in lubrication and plasticizers. With hexamethylenediamine azelaic acid forms Nylon-6,9, which finds specialized uses as a plastic.[5]
[edit] Medical
Azelaic acid is used to treat mild to moderate acne, both comedonal acne and inflammatory acne.[6][7] It works in part by stopping the growth of skin bacteria that cause acne, and by keeping skin pores clear.[8] Azelaic acid is also used as a topical gel treatment for rosacea, due to its ability to reduce inflammation.[7] Azelaic acid has been used for treatment of skin pigmentation including melasma and post inflammatory hyperpigmentation, particularly in those with darker skin types. It has been recommended as an alternative to hydroquinone (HQ).[9] As a tyrosinase inhibitor, azelaic acid reduces synthesis of melanin.[10]
[edit] Brand names
AzClear Action (20% lotion, Ego Pharmaceuticals), Azelex (20% cream, Allergan), White Action cream (20% cream,2% glycolic acid), SynCare), Finacea (15% gel, Intendis/Berlex Laboratories, subsidiaries of Bayer AG), Finevin (20% cream, Intendis/Berlex Laboratories), Skinoren (20% cream or 15% gel, Intendis), and Azaclear (azelaic acid and niacinamide, Epikinetics LLC).
[edit] Notes and references
- ^ a b Sigma-Aldrich catalog
- ^ 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.
- ^ Sarah Everts. "Vegetative Warfare". Chemical & Engineering News 89 (5): 53–55.
- ^ Jung, H. W.; Tschaplinski, T. J.; Wang, L.; Glazebrook, J.; Greenberg, J. T. (2009). "Priming in Systemic Plant Immunity". Science 324 (5923): 89. doi:10.1126/science.1170025. PMID 19342588.
- ^ Boy Cornils, Peter Lappe "Dicarboxylic Acids, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a08_523
- ^ Azelaic Acid for Acne, WebMD
- ^ a b Azelaic acid topical, Drugs.com
- ^ Liu R. H., Smith M. K., Basta S. A., Farmer E. R. ( (2006). "Azelaic acid in the treatment of papulopustular rosacea - A systematic review of randomized controlled trials". Archive of Dermatology 142 (8): 1047–1052. doi:10.1001/archderm.142.8.1047. PMID 16924055.
- ^ Draelos Z (Sept-Oct 2007). "Skin lightening preparations and the hydroquinone controversy.". Dermatol Ther 20 (5): 308–313. PMID 18045355.
- ^ Grimes, Pearl E. (2007-07-01). Aesthetics and Cosmetic Surgery for Darker Skin Types. Lippincott Williams & Wilkins. pp. 74–. ISBN 9780781784030. http://books.google.com/books?id=ALt93yGZccQC&pg=PA74. Retrieved 9 August 2011.
[edit] External links
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