5501-39-3

Basic information

• Product Name: 3-acetyl-4-hydroxy-6-methyl-2-pyridone
• Synonyms: 3-acetyl-4-hydroxy-6-methyl-2-pyridone;3-Acetyl-4-hydroxy-6-methyl-2(1H)-pyridinone;3-Acetyl-4-hydroxy-6-Methylpyridin-2(1H)-one
• CAS NO: 5501-39-3
• Molecular Formula: C₈H₉NO₃
• Molecular Weight: 167.16196
• EINECS: 226-837-3
• Mol File: 5501-39-3.mol

Chemical Properties

• Boiling Point: 324.4°Cat760mmHg
• Flash Point: 150°C
• Appearance: /
• Density: 1.308g/cm³
• Vapor Pressure: 1.92E-05mmHg at 25°C
• Refractive Index: 1.558
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-acetyl-4-hydroxy-6-methyl-2-pyridone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-acetyl-4-hydroxy-6-methyl-2-pyridone(5501-39-3)
• EPA Substance Registry System: 3-acetyl-4-hydroxy-6-methyl-2-pyridone(5501-39-3)

Safety Data

• Hazardous Substances Data: 5501-39-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
3-acetyl-4-hydroxy-6-methyl-2-pyridone is used as a pharmaceutical agent for its antioxidant and anti-inflammatory properties. Its ability to combat oxidative stress and reduce inflammation makes it a potential candidate for the development of drugs targeting various diseases and conditions.
Used in Cosmeceutical Applications:
In the cosmeceutical industry, 3-acetyl-4-hydroxy-6-methyl-2-pyridone is used as an active ingredient for its skin-friendly properties. Its antioxidant and anti-inflammatory effects can help protect the skin from environmental stressors, reduce inflammation, and promote overall skin health.
Used in Neurodegenerative Disease Treatment:
3-acetyl-4-hydroxy-6-methyl-2-pyridone has shown potential for use in the treatment of neurodegenerative diseases. Its antioxidant properties may help protect neurons from oxidative damage, while its anti-inflammatory effects can reduce neuroinflammation, which is often associated with neurodegenerative conditions.
Used as a Chelating Agent for Metal Ions:
3-acetyl-4-hydroxy-6-methyl-2-pyridone can be used as a chelating agent for metal ions. Its ability to bind with metal ions can help in the detoxification process and removal of harmful metal ions from the body, making it a potential candidate for applications in environmental and industrial settings.
Further research is needed to fully understand the potential uses and applications of 3-acetyl-4-hydroxy-6-methyl-2-pyridone, as well as to optimize its synthesis and formulation for various industries.

InChI:InChI=1/C8H9NO3/c1-4-3-6(11)7(5(2)10)8(12)9-4/h3H,1-2H3,(H2,9,11,12)

Upstream product

• 5977-14-0 acetoacetamido 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 77287-34-4 formamide 
• 82437-52-3 N-formylacetoacetamide 
• 3749-51-7 4-hydroxy-6-methyl-2-pyridone 
• 35287-94-6 4-hydroxy-7-methyl-2H-pyrano[3,2-c]pyridine-2,5(6H)-dione 

Downstream Products

• 79039-83-1 2,4-dichloro-3-ethynyl-6-methylpyridine 
• 79039-84-2 2,4-dichloro-3-(1-chlorovinyl)-6-methylpyridine 
• 7211-76-9 4-hydroxy-6-methyl-3-[(1E)-N-phenylethanehydrazonoyl]pyridine-2(1H)-one 
• 70542-11-9 2-(4-methoxy-phenyl)-7-methyl-6H-pyrano[3,2-c]pyridine-4,5-dione 
• 70542-14-2 6-bromo-2-(4-methoxy-phenyl)-7-methyl-6H-pyrano[3,2-c]pyridine-4,5-dione 
• 70542-09-5 2-(4-methoxy-phenyl)-7-methyl-2,3-dihydro-6H-pyrano[3,2-c]pyridine-4,5-dione 

Relevant articles and documents

Synthesis of functionalized pyrano[3,2-c]pyridines and their transformations to 4-hydroxy-3[(1E)-N-hydroxyalkanimidoyl]pyridones

Reaction of 4-hydroxy-6-methyl-2(1H)-pyridones 1a and 4-hydroxy-1,6- dimethyl-2(1H)-pyridones 1b with diethyl malonates 2a-e leads to the formation of pyrano[3,2-c]pyridines 4a-j. Degradation of 4a-i affords the corresponding ketones 6a-i. Condensation of ketones 6a-i with hydroxyl amine or phenyl hydrazine hydrochloride is described. Copyright Taylor & Francis Group, LLC.

Synthesis of N-Acylacetoacetamide using 2,2,6-Trimethyl-1,3-dioxin-4-one

Diketene-acetone adduct (2,2,6-trimethyl-1,3-dioxin-4-one) 1 reacts with amide NH to give the corresponding N-acetoacetates 2.Formamide and basic amides such as picolinamide, on treatment with the adduct, are transformed to the N-acyl-2,6-dimethyl-4-oxo-4H-pyran-3-carboxamide (4a and 4p) together with the corresponding N-acetoacetates.Keywords--diketene-acetone adduct; 1,3-dioxin-4-one; acetylketene; diketene; acetoacetylation; 4-pyrone derivatives; N-acylacetoacetamide

Synthesis of Methylpyridine Derivatives. XXXIV. Condensation of Acetoacetamide with Ketones to form Pyridone Derivatives

Condensation of acetoacetamide (1) with acetone in polyphosphoric acid (PPA) gave 4,6-dimethyl-2(1H)-pyridone (2a) in 32percent yield.Similarly, the amide 1 was condensed with 2-butanone, 2-pentanone, 3-pentanone, cyclopentanone, cyclohexanone, cycloheptanone, acetophenone, and propiophenone to give the corresponding pyridone derivatives (2b-i) in 13-76percent yields.Condensation of the amide 1 with acetylacetone and ethyl acetoacetate gave 3-acetyl-4,6-dimethyl-2(1H)-pyridone (5) and ethyl 4,6-dimethyl-2(1H)-pyridone-5-carboxylate (6), respectively.Self-condensation of the amide 1 in PPA gave 3-acetyl-4-hydroxy-6-methyl-2(1H)-pyridone (7).