Piroctone olamine
Chemical compound
From Wikipedia, the free encyclopedia
Piroctone olamine (INN; also known as piroctone ethanolamine) is an organic compound used as an antimicrobial active in anti-dandruff and anti-seborrhoeic dermatitis scalp products. It is the ethanolamine salt of piroctone, a hydroxamic acid derivative. It is described as a white to slightly yellowish-white crystalline powder with a mild characteristic odour, very slightly soluble in water and freely soluble in ethanol, chloroform, and ether.[1] It has been marketed by Clariant under the trade name Octopirox.[2]
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| Names | |
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| IUPAC name
1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-1,2-dihydropyridin-2-one; 2-aminoethan-1-ol | |
| Other names
Piroctone ethanolamine; Octopirox | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.065.957 |
| MeSH | Piroctone+olamine |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C16H30N2O3 | |
| Molar mass | 298.421 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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According to later published sources, piroctone olamine was first synthesized in 1979 by Schwarzkopf-Henkel in Germany.[3]
Uses
Mechanism of action
Piroctone olamine is generally described as an antifungal active associated with suppression of scalp microorganisms, especially species of Malassezia linked to dandruff and seborrhoeic dermatitis.[4][9] Proposed mechanisms in the literature include inhibition of ergosterol synthesis and, alternatively, penetration of the fungal cell membrane followed by chelation of iron ions, with interference in mitochondrial energy metabolism. The exact mechanism of action has not been fully established.[10][7]
Regulation
In the European Union, piroctone olamine is listed in Annex V of Regulation (EC) No 1223/2009 as an allowed preservative in cosmetic products, with a maximum concentration of 1.0% in rinse-off products and 0.5% in other products.[11] The former Scientific Committee on Cosmetic Products and Non-Food Products Intended for Consumers (SCCNFP) also reviewed the safety of piroctone olamine and its monoethanolamine salt for non-preservative uses in leave-on facial products.[12]