Azelaic acid
[CAS# 123-99-9]

Identification

• Classification: API >> Special medicine >> Dermatology medication
• Name: Azelaic acid
• Synonyms: Nonanedioic acid
• Molecular Formula: C₉H₁₆O₄
• Molecular Weight: 188.22
• CAS Registry Number: 123-99-9
• EC Number: 204-669-1
• SMILES: C(CCCC(=O)O)CCCC(=O)O

Properties

• Solubility: 10 mM (DMSO)
• Density: 1.225
• Melting point: 98-103 °C
• Boiling point: 286 °C (100 mmHg)
• Flash point: 215 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Azelaic acid, a dicarboxylic acid, was first identified in the early 19th century by German chemist Justus von Liebig. It was initially isolated from the oxidation of oleic acid, which is present in various vegetable oils. Its name is derived from "azaleas," the Greek word for "dry," reflecting its source from rancid fats. The compound's chemical structure was determined through further research, leading to the understanding of its versatile properties and potential applications. Azelaic acid's discovery paved the way for its use in dermatological treatments and other industrial processes.

Azelaic acid is widely used in dermatology for treating skin conditions such as acne, rosacea, and hyperpigmentation. It exhibits anti-inflammatory, antibacterial, and keratolytic properties. In acne treatment, it reduces inflammation and bacterial growth in the pores, preventing the formation of comedones and lesions. For rosacea, azelaic acid helps reduce redness and swelling. It also inhibits tyrosinase, an enzyme involved in melanin production, making it effective in treating hyperpigmentation and melasma.

Azelaic acid is incorporated into various skincare products, including creams, gels, and serums, for its benefits in improving skin texture and tone. It is effective in reducing the appearance of blemishes, dark spots, and uneven skin tone. Its gentle exfoliating properties help unclog pores and promote cell turnover, leading to smoother and clearer skin. Azelaic acid is suitable for sensitive skin types due to its mild nature and minimal side effects.

In the food industry, azelaic acid is used as a preservative and flavoring agent. Its antimicrobial properties help preserve food by inhibiting the growth of bacteria and fungi, extending shelf life. Additionally, azelaic acid contributes to flavor development in certain food products, enhancing their taste and quality. Its application in food preservation supports the safety and longevity of packaged foods and beverages.

Azelaic acid serves as a monomer in the production of polymers and resins. It is used in the synthesis of alkyd resins and polyesters, which are employed in coatings, paints, and adhesives. These polymers exhibit good mechanical properties, chemical resistance, and flexibility, making them suitable for industrial applications. Azelaic acid-based resins contribute to the durability and performance of coatings used in automotive, construction, and packaging industries.

In the lubricant industry, azelaic acid is used as a component in the formulation of synthetic lubricants and plasticizers. It helps enhance the lubricity and thermal stability of lubricants, improving their performance in high-temperature and high-pressure environments. Azelaic acid-based lubricants are used in automotive and industrial applications, where they reduce friction and wear on moving parts.

Azelaic acid is also explored for use in agrochemicals as a bio-stimulant and plant growth regulator. It helps improve plant resistance to stress and disease by enhancing their natural defense mechanisms. Azelaic acid is studied for its potential to boost crop yields and promote sustainable agriculture by supporting plant health and resilience.

References

1964. Pimelic Acid as a By-product of Azelaic Acid Degradation by Pseudomonas sp. Nature.
DOI: 10.1038/20439a0

2012. Topical antimicrobial treatment of acne vulgaris: an evidence-based review. American Journal of Clinical Dermatology.
DOI: 10.2165/11597880-000000000-00000

2024. Selected Medium-Chain Dicarboxylic Acid Combinations: Improving the Shelf Life and Quality of Beef During Chilled Storage. Food and Bioprocess Technology.
DOI: 10.1007/s11947-024-03679-4