Azelaic acid

Azelaic acid
Azelaic acid
Identifiers
CAS number 123-99-9 YesY
PubChem 2266
ChemSpider 2179 YesY
UNII F2VW3D43YT YesY
DrugBank APRD00812
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
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, 5.598[2]
Pharmacology
Bioavailability Very low
Routes of
administration
Topical
Elimination
half-life
12 hours
Legal status


-only(US)

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

Contents

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]

Uses in hair and skin treatments

Acne treatment

Azelaic acid is used to treat mild to moderate acne; i.e. both comedonal acne and inflammatory acne. It works in part by stopping the growth of skin bacteria that cause acne, and by keeping skin pores clear.[6]

Rosacea treatment

Azelaic acid is also used as a topical gel treatment for rosacea, due to its ability to reduce inflammation. In some cases, females have reported hair growth on face and neck.

Pigmentation treatment

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), the current gold standard for skin lightening, as countries such as Japan and the EU have questioned the safety of HQ.[7]

It is a Tyrosinase inhibitor. This reduces synthesis of melanin.[8]

Hair loss

Azelaic acid may be useful as a hair growth stimulant. A research report by Stamatiadis in 1988 suggested that azelaic acid (and combinations of it, with zinc ion and vitamin B6) was a strong type I 5-alpha reductase (5-AR) inhibitor.[9] The enzyme, 5-AR (both Types I and II) convert testosterone to dihydrotestosterone (DHT). DHT has been shown to contribute to prostate enlargement (benign prostatic hyperplasia, BPH) and to damage hair follicles. However, no clinical studies have confirmed its efficacy in helping with hair loss.

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).

Notes and references

  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. 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. ^ 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. 
  7. ^ Draelos Z (Sept-Oct 2007). "Skin lightening preparations and the hydroquinone controversy.". Dermatol Ther 20 (5): 308–313. PMID 18045355. 
  8. ^ 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. 
  9. ^ Stamatiadis D, Bulteau-Portois MC, Mowszowicz I (Nov. 1988). "Inhibition of 5 alpha-reductase activity in human skin by zinc and azelaic acid.". Br J Dermatol 119 (5): 627–632. doi:10.1111/j.1365-2133.1988.tb03474.x. PMID 3207614. 

External links

cz:kyselina azelaová


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  • azelaic acid — nonano dirūgštis statusas T sritis chemija formulė HOOC(CH₂)₇COOH atitikmenys: angl. azelaic acid; nonanic acid rus. азелаиновая кислота; нонановая кислота ryšiai: sinonimas – azelaino rūgštis …   Chemijos terminų aiškinamasis žodynas

  • azelaic acid — |azə|lāik. noun Etymology: az + Greek elaion olive oil + English ic more at oil : a crystalline dicarboxylic acid HOOC(CH2)7COOH made usually by the oxidation of oleic acid or the acids from castor oil (as with nitric acid or ozone) and used in… …   Useful english dictionary

  • azelaic acid — noun An aliphatic dicarboxylic acid found in many cereals; it has an antibacterial action and is used in skin creams etc. Syn: nonanedioic acid …   Wiktionary

  • azelaic acid — an antibacterial drug applied externally as a cream in the treatment of acne. Possible side effects include local irritation and light sensitivity. Trade name: Skinoren. * * * az·e·la·ic ac·id (az″ə laґik) a dicarboxylic acid occurring …   Medical dictionary

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  • azelaic — adjective Of or pertaining to azelaic acid or its derivatives …   Wiktionary

  • Кислота Азелаиновая (Azelaic Acid) — антибактериальный лекарственный препарат; применяется наружно в виде крема для лечения угрей. Возможные побочные эффекты: местное раздражение кожи и повышение ее чувствительности к свету. Торговое название: скинорен (Skinoren). Источник:… …   Медицинские термины

  • Dicarboxylic acid — Dicarboxylic acids are organic compounds that contain two carboxylic acid functional groups. In molecular formulae for dicarboxylic acids, these groups are often written as HOOC R COOH, where R may be an alkyl, alkenyl, alkynyl, or aryl group.… …   Wikipedia

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