Azelaic Acid Formula: Structure, Properties & Applications

Azelaic Acid is a naturally occurring dicarboxylic acid found on the skin of yeast Malassezia furfur and found in entire grain oats, rye, grain and creature items. It has antibacterial, keratolytic, and comedolytic properties and is hostile to oxidant action. Azelaic acid is bactericidal against Propionibacterium acnes and Staphylococcus epidermidis because of its inhibitory impact on the combination of microbial cell proteins. It is an organic compound, also known as nonanedioic acid.

Read More: Carboxylic Acids

Key Terms: Azelaic Acid, Dicarboxylic Acid, Bacteria, Yeast, Solid, Saturated, Anti-Inflammatory, Skin, Proteins, Organic Compound

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What is Azelaic Acid?

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Azelaic Acid is a naturally occurring acid with anti-inflammatory properties and can be effective in treating mild to moderate acne. Azelaic acid works by killing the bacteria and by keeping the skin pores clear.

• Azelaic acid works by reducing the growth of skin bacteria and promotes exfoliation, which helps unclog blocked pores.
• Azelaic acid is also effective against pigmentary abnormalities, post-inflammatory hyperpigmentation, and dermatitis.
• Azelaic acid gently exfoliates dead skin cells and they are one of the main contributors to clogged pores.
• It produces hydrogen peroxide when applied to the skin.

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Formula and Structure of Azelaic Acid

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Azelaic acid is a nonanoic acid that can be obtained both naturally and at the industrial level. Naturally, it is found on the yeast Malassezia furfur. At an industry level, one can obtain azelaic acid by the ozonolysis of oleic acid.

• The acid are made through Ozonolysis. It's a nonanoic acid with its molecular formula being C₉H₁₆NO4, while its simplified molecular input line entry system is OC(=O)CCCCCCCC(O)=O.
• Azelaic acid can be referred to as 9-hydroxypentanedioic acid. The structural formula of azelaic acid is HOOC(CH-)COOH.
• At room temperature, azelaic acid is found in a solid state as its most stable conformation type.

Structure of Azelaic Acid

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Properties of Azelaic Acid

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Azelaic acid has some great properties making it useful in different ways. Some of its properties are:

• It is white, waxy, and belongs to the drug class dicarboxylic acids with the structural formula C₉H₁₃NO₃.
• The chemical formula is written as R-CH=CH-CO₂H. The molecular weight of azelaic acid happens to be 161.197 g/mol.
• Specifically, this organic compound has a melting point of 100 °C and a boiling point of 232 °C.
• The compound is made up of carbon, hydrogen, and oxygen.
• Azelaic acid is a saturated dicarboxylic acid. It is a colorless solid with an odor similar to that of butter.
• The compound is available in three different crystalline forms: alpha, beta, and gamma. Alpha-azelaic acid (AzA) and beta-azelaic acid (BA) are two naturally-occurring isomer forms of this compound.
• Azelaic acid is a naturally occurring dicarboxylic acid that possesses potent properties against malarial parasites.

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Applications of Azelaic Acid

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Some of the wide-range applications of Azelaic Acid are:

• Azelaic acid can be found naturally in grains, cereals, and animal products. It has been used as a preservative for cosmetics, foods such as powdered milk, and leather products.
• This compound may also be used as a pesticide for plants.
• Azelaic acid belongs to a class of medication that shows beneficial results in treating mild to moderate acne, both inflammatory acne and comedonal acne.
• It is used to kill the acne bacteria that trigger the skin pores. In addition, it decreases keratin production, which is a natural substance that encourages the growth of acne bacteria.
• Azelaic acid is a substance used extensively in cosmetics and other industries. While in the medical industry, it is used to treat various skin-related ailments.
• Azelaic acid is a dicarboxylic acid that comes from grains and it is used as a thickening agent in polymer industries. It can be further processed as lubricants and plasticizers in the lubricant industry.
• It is also used to treat some other skin conditions like rosacea, dermatitis, general inflammation, and hyperpigmentation.

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Things to Remember

• Azelaic acid is a naturally occurring acid basically produced by a species of fungus usually found on human skin. The name of the yeast is Malassezia furfur (pityrosporum ovale). It is also found in food items such as wheat, rye, and barley.
• The structural formula of azelaic acid is C₉H₁₃NO₃.
• It is commonly used in topical creams at 20% concentration to treat mild to moderate acne.
• Azelaic Acid finds its major applications in treating skin conditions such as acne.
• Even though there is usually no local irritation, topical application of azelaic acid can cause short-term burning, stinging, itching, and dryness, and longer-term skin hyperpigmentation in a small percentage of patients.

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