ChemicalBook CAS DataBase List 68890-66-4

68890-66-4

Name	Piroctone olamine
CAS	68890-66-4
EINECS(EC#)	272-574-2
Molecular Formula	C16H30N2O3
MDL Number	MFCD01690792
Molecular Weight	298.42
MOL File	68890-66-4.mol

Synonyms

1-hydroxy-4-methyl-6(2,4,4-trimethylpentyl)2-pyridon monoethanolamine salt OCTOPIROX PIROCTONE OLAMINE 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1h)-pyridinoncompd.with2-aminoethanol(1:1) 2(1H)-Pyridinone,1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-,compd.with2-aminoethanol(1:1) 4,4-trimethylpentyl)-1-hydroxy-4-methyl-6-(compd.with2-2(1h)-pyridinon octopiroxolamine PIROCTONE OLEAMINE 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2(1H)-one, compound with 2-aminoethanol (1:1) Piroctone olamine (OCTO) Piorctone Olamine 1-HYDROXY-4-METHYL-6-(2,4,4-TRIMETHYLPENTYL)2(1H)-PYRIDONE. 1-Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2(1H)-on, Verbindung mit 2-Aminoethanol (1:1) 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2-one 1-Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)-pyridone·2-aminoethanol 2-Aminoethanol/1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)-pyridone,(1:1)

Chemical Properties

Melting point	134.0 to 138.0 °C
Boiling point	135-235℃[at 101 325 Pa]
density	1.1[at 20℃]
vapor pressure	0-0Pa at 20-25℃
storage temp.	Inert atmosphere,2-8°C
solubility	Chloroform (Slightly, Sonicated), Methanol (Slightly)
form	neat
pka	5.9-7.4[at 20 ℃]
color	White to Off-White
Water Solubility	400-50000mg/L at 20-25℃
Merck	14,7502
Major Application	agriculture environmental
Cosmetics Ingredients Functions	PRESERVATIVE ANTI-SEBORRHEIC
InChI	InChI=1S/C14H23NO2.C2H7NO/c1-10-6-12(15(17)13(16)8-10)7-11(2)9-14(3,4)5;3-1-2-4/h6,8,11,17H,7,9H2,1-5H3;4H,1-3H2
InChIKey	BTSZTGGZJQFALU-UHFFFAOYSA-N
SMILES	C(N)CO.C(C1=CC(C)=CC(=O)N1O)C(C)CC(C)(C)C
LogP	1.05-3.86 at 20-25℃
CAS DataBase Reference	68890-66-4(CAS DataBase Reference)

Safety Data

Symbol(GHS)	GHS05
Signal word	Danger
Hazard statements	H315-H318-H412
Precautionary statements	P273-P280-P302+P352-P305+P351+P338+P310
WGK Germany	2
RTECS	UU7786150
REACH Registrations	Active
HS Code	2933399090
Storage Class	11 - Combustible Solids
Hazard Classifications	Aquatic Chronic 3 Eye Dam. 1 Skin Irrit. 2

Hazard Information

Uses

Piroctone olamine is used in combination with other substances as a part of shampoo effectively reduced the amount of dandruff and, at the same time, provided hair conditioning advantages. Recently was shown, that piroctone olamine could induce apoptosis and possessed a significant in vivo effect against myeloma.

Definition

ChEBI: An organoammonium salt that is the ethanolamine salt of piroctone.

Brand name

Octopirox (Hoechst AG, Germany).

benefits

Piroctone Olamine is a popular ingredient in hair care products that treat dandruff and other scalp conditions. Controls dandruff: Piroctone Olamine is effective at controlling the growth of Malassezia, a yeast that can contribute to dandruff and other scalp issues. By controlling the growth of this yeast, Piroctone Olamine can help to reduce or eliminate dandruff. Soothes the scalp: Piroctone Olamine has moisturizing properties that can help to soothe and hydrate the scalp. This can help prevent dryness, flakiness, and itching, common symptoms of dandruff and other scalp conditions. Safe for coloured hair: Piroctone Olamine is safe for use on coloured hair and will not cause fading or strip colour. Prevents fungal growth: Piroctone Olamine not only controls the growth of Malassezia, but it also prevents the growth of other fungi that can cause scalp problems. Long-lasting effect: Piroctone Olamine has been shown to have a longer-lasting effect than some other dandruff-fighting ingredients, meaning you may be able to go longer between washes. Gentle on the scalp: Piroctone Olamine is gentle on the scalp, making it suitable for sensitive skin.

Mechanism of action

Piroctone olamine, also known as Octopirox, is an antifungal and antibacterial agent commonly used in cosmetic and personal care products, such as shampoos, conditioners, and lotions. It works by inhibiting the growth of various microorganisms, including yeasts and fungi, by disrupting their cell membranes and interfering with their metabolism. Specifically, piroctone olamine targets the enzymes responsible for synthesizing the cell membrane of microorganisms, inhibiting their growth and causing their eventual death. It also has anti-inflammatory properties that help to reduce redness and itching on the scalp and skin.

Clinical Use

Piroctone olamine has both antifungal and antioxidant properties. It has been reported to be as effective as other antidandruff products at concentrations of 0.5–1% and is considered less toxic than zinc pyrithione when accidentally swallowed. Piroctone olamine products can be used by all patients and at any age. Like zinc pyrithione, they should be used daily. Because of their reduced toxicity, they may be preferred if used around small children.

Side effects

It should be kept in mind that shampoos with Piroctone Olamine should not be used more than twice a week, unlike other daily-use shampoos that don't have this ingredient. One of the biggest side effects of Piroctone Olamine is that it can cause irritation and itchiness on the head.

References

[1] Newby, D., Rutter, P. (2015). Community Pharmacy ANZ - EBook: Symptoms, Diagnosis and Treatment. United States: Elsevier.
[2] Youn, H. J., Kim, S. Y., Park, M., Jung, W. H., Lee, Y. W., Choe, Y. B., & Ahn, K. J. (2016). Efficacy and Safety of Cream Containing Climbazole/Piroctone Olamine for Facial Seborrheic Dermatitis: A Single-Center, Open-Label Split-Face Clinical Study. Annals of dermatology, 28(6), 733–739. https://doi.org/10.5021/ad.2016.28.6.733
[3] Lodén, M., & Wessman, C. (2000). The antidandruff efficacy of a shampoo containing piroctone olamine and salicylic acid in comparison to that of a zinc pyrithione shampoo. International journal of cosmetic science, 22(4), 285–289. https://doi.org/10.1046/j.1467-2494.2000.00024.x

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