Azelaic acid

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Azelaic acid
Azelaic acid.png
Azelaic-acid-3D-balls.png
Identifiers
CAS number 123-99-9 YesY
PubChem 2266
ChemSpider 2179 YesY
UNII F2VW3D43YT YesY
DrugBank DB00548
KEGG D03034 YesY
ChEBI CHEBI:48131 YesY
ChEMBL CHEMBL1238 YesY
ATC code D10AX03
Jmol-3D images Image 1
Properties
Molecular formula C9H16O4
Molar mass 188.22 g mol−1
Density 1.443 g/ml
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


-only(US)

Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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.

Production[edit]

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.

Biological function[edit]

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]

Applications[edit]

Polymers and related materials[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]

Medical[edit]

Azelaic acid is used to treat mild to moderate acne, both comedonal acne and inflammatory acne.[6][7] It belongs to a class of medication called dicarboxylic acids. It works by killing acne bacteria that infect skin pores. It also decreases the production of keratin, which is a natural substance that promotes the growth of acne bacteria[8] Azelaic acid is also used as a topical gel treatment for rosacea, due to its ability to reduce inflammation.[7] It clears the bumps and swelling caused by Rosacea. 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]

Brand names[edit]

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), Melazepam, Strata Dermatologics, 2oz, Mixed Dicarboxylic Acids 20% Azelaic Acid Cream.,and Azaclear (azelaic acid and niacinamide, Epikinetics LLC).

Notes and references[edit]

  1. ^ a b Sigma-Aldrich catalog
  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. ^ Sarah Everts. "Vegetative Warfare". Chemical & Engineering News 89 (5): 53–55. 
  4. ^ Jung, H. W.; Tschaplinski, T. J.; Wang, L.; Glazebrook, J.; Greenberg, J. T. (2009). "Priming in Systemic Plant Immunity". Science 324 (5923): 89–91. doi:10.1126/science.1170025. PMID 19342588. 
  5. ^ Boy Cornils, Peter Lappe "Dicarboxylic Acids, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a08_523
  6. ^ Azelaic Acid for Acne, WebMD
  7. ^ a b Azelaic acid topical, Drugs.com
  8. ^ 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. 
  9. ^ Draelos Z (Sept–Oct 2007). "Skin lightening preparations and the hydroquinone controversy.". Dermatol Ther 20 (5): 308–313. doi:10.1111/j.1529-8019.2007.00144.x. PMID 18045355. 
  10. ^ Grimes, Pearl E. (2007-07-01). Aesthetics and Cosmetic Surgery for Darker Skin Types. Lippincott Williams & Wilkins. pp. 74–. ISBN 978-0-7817-8403-0. Retrieved 9 August 2011. 

External links[edit]