Azelaic Acid CAS number 123-99-9 basic information

The IUPAC name is nonanedioic acid

CAS number 123-99-9

PubChem 2266

ChemSpider 2179

Azelaic acid [4]

Azelaic Acid [4]

Azalenic acid [4]

Chemical formula C9H16O4 [4]

Molecular weight 188.22 [1]

CAS login number 123-99-9

[4]EINECS Entry Number 204-669-1 [4]

[5] Melting point 106.5 ℃

[6] Boiling point 357.1 ° C [3]

[7] Density 1.225 g/cm3

[8][1] White to yellowish monoclinic prism, acicular crystal or powder

[9] Flash point 210 ℃

[10][1] Slightly soluble in cold water, soluble in hot water, ether, easily soluble in ethanol

Azelaic acid (also known as Azelaic acid or AzA) is a saturated dicarboxylic acid with the formula HOOC(CH2)7COOH. In the standard state, pure azelaic acid is a white powder. Azelaic acid occurs naturally in grains such as wheat, rye and barley. Azelaic acid can be used as a precursor in chemical products such as polymers and plasticizers, and it is also an ingredient in topical anti-acne medications and certain hair and skin treatments.

preparation

In industry, azelaic acid can be produced by the ozonation of oleic acid, a byproduct of which is azelaic acid. Azelaic acid is a bacterial breakdown product of azelaic acid that is naturally secreted by the fungus Malaxomyces furfura, which lives on normal skin.

Azelaic acid can be produced by oxidizing 9-octadecenoic acid with a strong oxidizing agent, such as potassium permanganate. [3]

Biological action

In plants, azelaic acid is a plant hormone involved in the defense response after infection. [4] It induces the accumulation of salicylic acid, which is an important component of the plant's defense response. [5]

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Polymers and related materials

Azelaic esters are used in lubricants and plasticizers. In the lubricant industry, it can be used as a thickening agent for lithium greases. The copolymer of azelaic acid and hexamethylenediamine is a special plastic polyamide 6,9. [2]

Medical use

Medical content in Wikipedia is for informational purposes only and should not be considered professional advice. For medical help or advice, consult a professional. See medical statement for details.

Azelaic acid 20% topical ointment, sold under the trade name Skinoren

Azelaic acid can be used to treat mild to moderate comedogenic and inflammatory acne. [6][7] Azelaic acid kills acne bacteria that infect pores and also reduces the production of keratin, a natural substance that promotes the growth of acne bacteria. [8] Because of its anti-inflammatory properties, azelaic acid can also be used as a topical drug to treat rosacea. It can treat lumps and swelling caused by rosacea. Azelaic acid acts by inhibiting the overactive protease activity that converts ductin into the antimicrobial peptide LL-37. [9] Azelaic acid can also be used to treat skin pigmentation, including melasma and hyperpigmentation after inflammation, especially for those with darker skin tones. It is also recommended as a substitute for hydroquinone. [10] As a tyrosinase inhibitor, azelaic acid inhibits melanin synthesis. [11]

Similar to the hair loss drugs finasteride and dutasteride, azelaic acid is also a potent 5α reductase inhibitor.