Azelaic acid

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Azelaic acid
Skeletal formula of azelaic acid
Ball-and-stick model of the azelaic acid molecule
Names
IUPAC name
nonanedioic acid
Identifiers
ATC code D10AX03
123-99-9 Yes
ChEBI CHEBI:48131 Yes
ChEMBL ChEMBL1238 Yes
ChemSpider 2179 Yes
DrugBank DB00548 Yes
Jmol-3D images Image
KEGG D03034 Yes
PubChem 2266
UNII F2VW3D43YT Yes
Properties
Molecular formula
 C9H16O4
Molar mass 188.22 g·mol−1
Density 1.443 g/ml
Melting point 109 to 111 °C (228 to 232 °F; 382 to 384 K)[1]
Boiling point 286 °C (547 °F; 559 K) at 100 mmHg[1]
2.14 g/L[2]
Acidity (pKa) 4.550, 5.498[2]
Pharmacology
Bioavailability Very low
Topical
Elimination
half-life
 12 hours
Legal status
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 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.

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.

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]

Applications

Polymers and related materials

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

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. The mechanism of action is thought to be through the inhibition of hyperactive protease activity that converts cathelicidin into the antimicrobial skin peptide LL-37.[9] 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).[10] As a tyrosinase inhibitor, azelaic acid reduces synthesis of melanin.[11]

Brand names

Brand names for azelaic acid include Azepur 99+ (Azeco Cosmeceuticals), Azaclear (azelaic acid and niacinamide, Epikintics), AzClear Action (Ego Pharmaceuticals), Azelex (Allergan), White Action cream (SynCare), Finacea (Intendis/Berlex Laboratories), Finevin (Intendis/Berlex Laboratories), Melazepam (Strata Dermatologics), Skinoren (Intendis), and Ezanic (Intas).

References

  1. ↑ 1.0 1.1 Sigma-Aldrich catalog
  2. ↑ 2.0 2.1 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 (January 31, 2011). "Vegetative Warfare". Chemical & Engineering News 89 (5): 53–55. (subscription required (help)).
  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. Bibcode:2009Sci...324...89W. 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. ↑ 7.0 7.1 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. ↑ Reinholz, M; Ruzicka, T; Schauber, J (2012). "Cathelicidin LL-37: An Antimicrobial Peptide with a Role in Inflammatory Skin Disease". Annals of Dermatology 24 (2): 126–135. doi:10.5021/ad.2012.24.2.126. PMC 3346901. PMID 22577261.
  10. ↑ Draelos Z (Sep–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.
  11. ↑ 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