Piroctone olamine
[CAS# 68890-66-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: Piroctone olamine
• Synonyms: 1-Hydroxy-4-methyl-6(2,4,4-trimethylpentyl)2-pyridon monoethanolamine salt
• Molecular Formula: C₁₄H₂₃NO₂.C₂H₇NO;C₁₆H₃₀N₂O₃
• Molecular Weight: 298.42
• CAS Registry Number: 68890-66-4
• EC Number: 272-574-2
• SMILES: CC1=CC(=O)N(C(=C1)CC(C)CC(C)(C)C)O.C(CO)N

Properties

• Solubility: 0.632 mg/mL (water)

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS09 Danger
• Risk Statements: H315-H318-H335-H400-H410-H412
• Safety Statements: P261-P264-P264+P265-P271-P273-P280-P302+P352-P304+P340-P305+P354+P338-P317-P319-P321-P332+P317-P362+P364-P391-P403+P233-P405-P501

Discovery and Applications

Piroctone ethanolamine, also known as octypyrone, was first synthesized in the 1960s by scientists at Hoechst AG. It was originally developed as an antifungal agent to treat a variety of fungal infections, including those affecting the skin and scalp. Piroctone ethanolamine is an ethanolamine with broad-spectrum antibacterial properties and low toxicity.

Piroctone ethanolamine is primarily used as an active ingredient in antifungal formulations such as shampoos, creams, lotions and soaps to treat and prevent fungal infections of the skin and scalp. Piroctone ethanolamine works by destroying the cell membrane of fungal cells, thereby inhibiting their growth and proliferation. Piroctone ethanolamine is a key ingredient in anti-dandruff shampoos because of its ability to effectively control and eliminate dandruff-causing fungi, such as Malassezia furfur. It helps reduce scalp itching, flaking and irritation associated with dandruff and relieves scalp problems. Studies have found that piroctone ethanolamine controls the proliferation of Malassezia and restores the balance of the skin microbiota, helping to relieve symptoms and reduce recurrences. In addition to its antifungal properties, piroctone ethanolamine also exhibits antimicrobial activity against certain acne-causing bacteria, such as Propionibacterium acnes. Therefore, it is used as an active ingredient in anti-acne products, including cleansers, toners, and spot care products. Piroctone ethanolamine is used as a preservative in cosmetics and personal care products to inhibit the growth of bacteria, yeasts and molds that can cause product spoilage and degradation, helping to maintain the microbiological stability of formulations. Piroctone ethanolamine is also used in veterinary dermatology to treat dandruff and seborrheic dermatitis in pets such as dogs and cats.

References

2024. Scalp microbiome composition changes and pathway evaluations due to effective treatment with Piroctone Olamine shampoo. International Journal of Cosmetic Science, 46(1).
DOI: 10.1111/ics.12933

2023. Investigation of piroctone olamine delivery to the skin from single, binary and ternary solvent systems. International Journal of Cosmetic Science, 45(6).
DOI: 10.1111/ics.12935

1988. Percutaneous absorption of Octopirox. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 26(1).
DOI: 10.1016/0278-6915(88)90041-5