|Molar mass||188.22 g·mol−1|
|Melting point||109 to 111 °C (228 to 232 °F; 382 to 384 K)|
|Boiling point||286 °C (547 °F; 559 K) at 100 mmHg|
|Acidity (pKa)||4.550, 5.498|
|Legal status||US: ℞-only|
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
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.
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.
In plants, azelaic acid serves as a "distress flare" involved in defense responses after infection. It serves as a signal that induces the accumulation of salicylic acid, an important component of a plant's defensive response.
Azelaic acid is used to treat mild to moderate acne, both comedonal acne and inflammatory acne. 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. Azelaic acid is also used as a topical gel treatment for rosacea, due to its ability to reduce inflammation. 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. 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). As a tyrosinase inhibitor, azelaic acid reduces synthesis of melanin.
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).
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- Sigma-Aldrich catalog
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