68890-66-4

Basic information

• Product Name: Piroctone olamine
• Synonyms: 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;1-hydroxy-4-methyl-6(2,4,4-trimethylpentyl)2-pyridon monoethanolamine salt;OCTOPIROX;PIROCTONE OLAMINE;PIROCTONE OLEAMINE
• CAS NO: 68890-66-4
• Molecular Formula: C₁₄H₂₃NO₂
• Molecular Weight: 298.42
• EINECS: 272-574-2
• Product Categories: OLED materials,pharm chemical,electronic;ARAMINE;bacteriostatic and fungistatic
• Mol File: 68890-66-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 134.0 to 138.0 °C
• Boiling Point: 344.1 °C at 760 mmHg
• Flash Point: 161.9 °C
• Appearance: White or slightly yellow crystalline powder
• Density: 1.1[at 20℃]
• Vapor Pressure: 4.31E-06mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly, Sonicated), Methanol (Slightly)
• PKA: 5.9-7.4[at 20 ℃]
• Water Solubility: 400-50000mg/L at 20-25℃
• Merck: 14,7502
• CAS DataBase Reference: Piroctone olamine(CAS DataBase Reference)
• NIST Chemistry Reference: Piroctone olamine(68890-66-4)
• EPA Substance Registry System: Piroctone olamine(68890-66-4)

Safety Data

• WGK Germany: 2
• RTECS: UU7786150
• Hazardous Substances Data: 68890-66-4(Hazardous Substances Data)

Usage

Description

Piroctone olamine (INN; also known as piroctone ethanolamine; brand name Octopirox) is a compound sometimes used in the treatment of fungal infections.Piroctone olamine is the ethanolamine salt of the hydroxamic acid derivative piroctone.

Appearance

White or slightly yellow crystalline powder.

Solubility

Freely soluble in 10% ethanol in water; soluble in solution containing surfactants in water or in 1%-10% ethanol; slightly soluble in water and in oil. The solubility in water varies by pH value, and is a litter larger in neutral or weak basic solution than in acid solution.

Toxicity

Acute toxicity : Acute oral LD50 –rat 8100mg/kg, practically nontoxic. Subchronic toxicity : NOEL: 100mg//kg/d (rat, orally, 3 months). Chronic toxicity and carcinogencity : Negative. Mutagenicity : Negative. Irritation to skin and eye : Very low.

Uses

Different sources of media describe the Uses of 68890-66-4 differently. You can refer to the following data:
1. 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.
2. Piroctone Olamine is an anti-dandruff agent used in shampoo formulations.

Definition

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

InChI:InChI=1/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

Synthetic route

6-(2,4,4-trimethylpentyl)-1-hydroxy-4-methyl-2(1H)-pyridone (68890-66-4, 50650-76-5) + ethanolamine (141-43-5) → piroctone olamine (68890-66-4)

Conditions	Yield
In ethyl acetate at 40℃;	89.7%
With hydroxylamine hydrochloride In dichloromethane; ethyl acetate at 50℃; Temperature;

Methyl 3,3-dimethylacrylate (924-50-5) → piroctone olamine (68890-66-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: aluminum (III) chloride; tin(IV) chloride / 5 h / 40 °C / Cooling with ice; Reflux 2: sulfuric acid / water / 5 h / Reflux 3: hydroxylamine hydrochloride; dmap / dichloromethane; methanol / 8 h / 40 °C 4: ethyl acetate / 40 °C View Scheme
Multi-step reaction with 4 steps 1.1: anhydrous aluminum chloride, anhydrous lanthanum chloride, anhydrous lithium perchlorate on silica gel catalyst / dichloromethane / 1 h / 0 °C 1.2: 11 h / 25 - 40 °C 2.1: 34 h / 210 °C / Inert atmosphere 3.1: hydroxylamine hydrochloride; sodium methylate; acetic acid / dichloromethane; water / 18 h / 30 °C 4.1: hydroxylamine hydrochloride / dichloromethane; ethyl acetate / 50 °C View Scheme

isononanoyl chloride (36727-29-4) → piroctone olamine (68890-66-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: aluminum (III) chloride; tin(IV) chloride / 5 h / 40 °C / Cooling with ice; Reflux 2: sulfuric acid / water / 5 h / Reflux 3: hydroxylamine hydrochloride; dmap / dichloromethane; methanol / 8 h / 40 °C 4: ethyl acetate / 40 °C View Scheme
Multi-step reaction with 4 steps 1.1: anhydrous aluminum chloride, anhydrous lanthanum chloride, anhydrous lithium perchlorate on silica gel catalyst / dichloromethane / 1 h / 0 °C 1.2: 11 h / 25 - 40 °C 2.1: 34 h / 210 °C / Inert atmosphere 3.1: hydroxylamine hydrochloride; sodium methylate; acetic acid / dichloromethane; water / 18 h / 30 °C 4.1: hydroxylamine hydrochloride / dichloromethane; ethyl acetate / 50 °C View Scheme

3,7,9,9-tetramethyl-2-decen-5-onic acid methyl ester → piroctone olamine (68890-66-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / water / 5 h / Reflux 2: hydroxylamine hydrochloride; dmap / dichloromethane; methanol / 8 h / 40 °C 3: ethyl acetate / 40 °C View Scheme
Multi-step reaction with 3 steps 1: 34 h / 210 °C / Inert atmosphere 2: hydroxylamine hydrochloride; sodium methylate; acetic acid / dichloromethane; water / 18 h / 30 °C 3: hydroxylamine hydrochloride / dichloromethane; ethyl acetate / 50 °C View Scheme

piroctone olamine (68890-66-4) → 6-(2,4,4-trimethylpentyl)-1-hydroxy-4-methyl-2(1H)-pyridone (68890-66-4, 50650-76-5)

Conditions	Yield
With hydrogenchloride In ethanol at 32 - 50℃; for 1.5h; Solvent;	99.1%

piroctone olamine (68890-66-4) → 4-methyl-6-(2,4,4-trimethylpentyl)pyridine-2(1H)-thione

Conditions	Yield
With Lawessons reagent In benzene at 80℃; for 1h;	21%

6A-O-methacryloyl-β-cyclodextrin + piroctone olamine (68890-66-4) → C2H7NO*C14H23NO2*C46H74O36

Conditions	Yield
In ethanol; water at 24.99℃; for 48h; pH=>= 10; Thermodynamic data;

piroctone olamine (68890-66-4) + fipronilβ-cyclodextrin (7585-39-9) → C42H70O35*C2H7NO*C14H23NO2

Conditions	Yield
In water at 24.99℃; for 48h; pH=>= 10; Thermodynamic data;

Upstream product

• 36727-29-4 isononanoyl chloride 
• 924-50-5 Methyl 3,3-dimethylacrylate 
• 68890-66-4 6-(2,4,4-trimethylpentyl)-1-hydroxy-4-methyl-2(1H)-pyridone 
• 141-43-5 ethanolamine 
• 504-29-0 2-aminopyridine 
• 50650-75-4 4-methyl-6-(2,4,4-trimethylpentyl)-2H-pyran-2-one 

Downstream Products

• 68890-66-4 6-(2,4,4-trimethylpentyl)-1-hydroxy-4-methyl-2(1H)-pyridone 

Relevant articles and documents

Preparation process of pyridinone ethanol amine salt

The invention relates to the technical field of pyridone ethanol amine salt processing, and particularly discloses a pyridone ethanol amine salt preparation process, which comprises: carrying out an acylation reaction, a ring-closure reaction, a hydroxyamination reaction and a salt forming reaction on 3,3-dimethyl acrylate and isononyl chloride to obtain pyridone ethanol amine salt; wherein the acylation reaction is carried out in the presence of a supported catalyst, the supported catalyst comprises an active component and a carrier, the carrier is silica gel, the active component comprises anhydrous aluminum chloride, anhydrous lanthanum chloride and anhydrous lithium perchlorate, and the loading capacity of anhydrous aluminum chloride on the carrier is 7-11 wt%; the loading capacity ofanhydrous lanthanum chloride on the carrier is 3-5 wt%; and the loading capacity of anhydrous lithium perchlorate on the carrier is 0.8-1.5 wt%. According to the preparation process of pyridinone ethanol amine salt, the catalytic Friedel-Crafts acylation reaction is realized, the supported catalyst is convenient to recover, and the activity and selectivity of the supported catalyst are improved.

Preparation method of pyridinone ethanolamine salt

The invention discloses a preparation method of a pyridinone ethanolamine salt. The preparation method comprises the reaction steps of Friedel-Crafts acylation, ring closing, hydroxyamination, salification and the like. According to the preparation method, the pyridinone ethanolamine salt can be efficiently prepared under mild conditions, less reaction materials are consumed, the yield and purityof products obtained in the steps are high, and complex purification steps are not needed.

PROCESS FOR FORMING 2-HYDROXYPYRIDINE-1-OXIDE OR DERIVATIVES THEREOF

A process for forming 2-hydroxypyridine-1 -oxide or derivatives thereof, the process comprising inter alia providing a solution comprising at least one compound according to Formula (1) (I) and recovering a compound according to Formula (2) (2) Also related products, uses, methods and compositions.