Azelaic Acid Formula

Azelaic acid is a naturally occurring dicarboxylic acid whose chemical formula is C₉H₁₆O₄, while its simplified molecular input line entry system (SMILES) is OC(=O)CCCCCCCC(O)=O. It exists as a white powder that is made up of 9 carbon atoms, 16 hydrogen atoms, and 4 atoms of oxygen. It is an organic compound that can be found in wheat, rye, and barley. It can be produced naturally by Malassezia furfur, which is a yeast that lives on normal skin, while industrially it is prepared by the ozonolysis of oleic acid. This acid possesses antibacterial, keratolytic, comedolytic, and anti-oxidant properties. Thus, it is used to reduce inflammation associated with acne and rosacea. It also serves as a base for several industrial products, including polymers and plasticizers.

Structure of Azelaic Acid

Azelaic acid has the chemical formula C₉H₁₆O₄ or HOOC(CH₂)₇COOH, while its simplified molecular input line entry system (SMILES) is OC(=O)CCCCCCCC(O)=O. It is a dicarboxylic acid that is made up of 9 carbon atoms, 16 hydrogen atoms, and 4 atoms of oxygen. Its IUPAC name is Nonanedioic acid. 

Azelaic Acid Structure

Production of Azelaic Acid

Azelaic acid is a naturally occurring dicarboxylic acid that can be found in wheat, rye, and barley. It can be produced naturally by Malassezia furfur, which is a yeast that lives on normal skin, while industrially it is prepared by the ozonolysis of oleic acid. Industrially, ozonolysis of oleic acid produces azelaic acid and pelargonic acid (nonanoic acid). Pelargonic acid (nonanoic acid) yields azelaic acid by bacterial degradation.

Preparation of oleic acid

Properties of Azelaic Acid

Chemical Formula	C9H16O4
IUPAC Name	Nonanedioic acid
Molar mass/Molecular Weight	188.22 g/mol
Appearance	White solid
Density	1.443 g/mL
Melting point	109 to 111 °C
Boiling point	286 °C
Flash point	210 °C (closed cup)
Solubility in water	2.14 g/L
Acidity (pKa)	4.550, 5.498
Refractive index	1.4303 at 111℃

Uses of Azelaic Acid

• Azelaic acid can be used to treat mild to moderate acne. It functions by killing the bacteria that are responsible for acne.
• This acid possesses antibacterial, keratolytic, comedolytic, and anti-oxidant properties. Thus, it is used to reduce inflammation associated with acne and rosacea. 
• It is used for the treatment of skin pigmentation and also helps cure mild acne. It also helps to lighten the skin that’s discolored by melanin.
• It is also used to prevent microbial cellular protein synthesis.
• It also serves as a base for several industrial products, including polymers and plasticizers. 
• This acid is used as a thickening agent in polymer industries.
• Esters of azelaic acid are used as plasticizers and lubricants.

Side-Effects of Azelaic Acid

The following are some side-effects of azelaic acid:

• Azelaic acid may cause a burning or tingling sensation on the skin. 
• It may also cause mild skin dryness or redness, or the skin may peel off at the application site. 
• Avoid contact with the eyes as it may cause mild eye irritation. 
• Inhalation of this may cause respiratory tract irritation. 
• The less common adverse effects include fever, difficulty in breathing, blisters, hives, joint pains, lack of appetite, constipation, change in taste, nausea, diarrhoea, etc.

FAQs on Azelaic Acid Formula

Question 1: What is the formula of Azelaic acid?

Answer: 

Azelaic Acid is a naturally occurring dicarboxylic acid whose chemical formula is C₉H₁₆O₄, while its simplified molecular input line entry system (SMILES) is OC(=O)CCCCCCCC(O)=O. It is an organic compound that can be found in wheat, rye, and barley.

Question 2: How is azelaic acid prepared?

Answer:

Azelaic acid is a naturally occurring dicarboxylic acid that can be found in wheat, rye, and barley. It can be produced naturally by Malassezia furfur, which is a yeast that lives on normal skin, while industrially it is prepared by the ozonolysis of oleic acid. Industrially, ozonolysis of oleic acid produces azelaic acid and pelargonic acid (nonanoic acid). Pelargonic acid (nonanoic acid) yields azelaic acid by bacterial degradation.

Question 3: Mention some properties of azelaic acid.

Answer: 

Azelaic acid is a naturally occurring dicarboxylic acid whose chemical formula is C9H16O4. It is a yellowish to white crystalline powder with a molecular weight of 188.223 g/mol. It is soluble in organic solvents, alcohols, and water, and is slightly soluble in benzene and ethyl ether. Its melting point ranges from 109 to 111 °C, while its boiling point is 286 °C.

Question 4: Describe some medical uses of azelaic acid.

Answer: 

Azelaic acid can be used to treat mild to moderate acne. This acid possesses antibacterial, keratolytic, comedolytic, and anti-oxidant properties. Thus, it is used to reduce inflammation associated with acne and rosacea. It is used for the treatment of skin pigmentation and also helps cure mild acne.

Question 5: Mention some side effects of azelaic acid.

Answer: 

Azelaic acid may cause a burning or tingling sensation on the skin. It may also cause mild skin dryness or redness, or the skin may peel off at the application site. Avoid contact with the eyes as it may cause mild eye irritation. Inhalation of this may cause respiratory tract irritation.

Question 6: Brief about the reaction of ozonolysis of oleic acid.

Answer: 

Industrially, ozonolysis of oleic acid produces azelaic acid and pelargonic acid (nonanoic acid). Pelargonic acid (nonanoic acid) yields azelaic acid by bacterial degradation.