4-Hydroxy-6-methyl-2-pyrone

Base Information

• Chemical Name: 4-Hydroxy-6-methyl-2-pyrone
• CAS No.: 675-10-5
• Molecular Formula: C6H6O3
• Molecular Weight: 126.112
• Hs Code.: 29322980
• Mol file: 675-10-5.mol

Synonyms:2H-Pyran-2-one,4-hydroxy-6-methyl-;Sorbicacid, 3,5-dihydroxy-, d-lactone (6CI,7CI);Triacetic acid lactone;4-Hydroxy-6-methyl-2H-pyran-2-one;4-Hydroxy-6-methyl-a-pyrone;4-Hydroxy-6-methylpyran-2-one;6-Methyl-4-hydroxy-2-pyrone;NSC 34625;

Chemical Property of 4-Hydroxy-6-methyl-2-pyrone

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.000311mmHg at 25°C
• Melting Point: 188-190 °C (dec.)(lit.)
• Refractive Index: 1.56
• Boiling Point: 239.074 °C at 760 mmHg
• PKA: 5.14±0.30(Predicted)
• Flash Point: 108.677 °C
• PSA: 50.44000
• Density: 1.348 g/cm³
• LogP: 0.65380
• Storage Temp.: Store below +30°C.
• Solubility.: 8.6g/l
• Water Solubility.: 8.60 g/L (20 ºC)

Purity/Quality:

99% ^*data from raw suppliers

4-Hydroxy-6-methylpyran-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Hydroxy-6-methylpyran-2-one was used in the synthesis of pyrano[3,2-c]pyridones with antiproliferative and apoptosis inducing activities. It was also used in the design of benzisothiazolone human leukocyte elastase inhibitors.

Technology Process of 4-Hydroxy-6-methyl-2-pyrone

There total 37 articles about 4-Hydroxy-6-methyl-2-pyrone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one (771-03-9) → 4-hydroxy-6-methyl-2-pyron (675-10-5)

Guidance literature:

With sulfuric acid; In water; at 130 ℃; for 0.216667h; Flow reactor;

DOI:10.1002/ejoc.201600222

Reference yield: 94.0%

3,5-dioxohexanoic acid (2140-49-0) → 4-hydroxy-6-methyl-2-pyron (675-10-5)

Guidance literature:

With trifluoroacetic acid; trifluoroacetic anhydride; for 0.5h; Heating;

Reference yield: 92.0%

2,2-dimethyl-6-(2-oxo-2-methylethyl)-4H-1,3-dioxin-4-one (130473-38-0) → 4-hydroxy-6-methyl-2-pyron (675-10-5)

Guidance literature:

In toluene; at 100 ℃; for 0.5h;

DOI:10.3390/molecules24173193

upstream raw materials:

3,5-dioxohexanoic acid

phenyldiazomethane

4-methoxy-6-(phenylthiomethyl)-2H-pyran-2-one

2,2-dimethyl-6-(2-oxo-2-methylethyl)-4H-1,3-dioxin-4-one

Downstream raw materials:

4-methoxy-6-methyl-2H-pyran-2-one

2-methoxy-6-methyl-pyran-4-one

4-Hydroxy-6-methyl-3-(1'-phenyl-propyl)-2-pyrone

2,4-dichloro-6-methyl-3-nitropyridine

Refernces

• 1、 Kurosaki, Fumiya,Mitsuma, Satoru,Arisawa, Munehisa. "Activation of acyl condensation reaction of monomeric 6-hydroxymellein synthase, a multifunctional polyketide biosynthetic enzyme, by free coenzyme A". . p. 597 - 604. Retrieved 2002.
• 2、 Haeusler, Johannes. "Note on the Synthesis of 4-Hydroxy-6-methyl-5,6-dihydro-2H-pyran-2-one". . p. 1213 - 1216. Retrieved 1982.
• 3、 Ruhemann,Wolf. "-". . p. 1384. Retrieved 1896.
• 4、 Marsico, Giulia,Ciccone, Maria Sabrina,Masi, Marco,Freda, Fabrizio,Cristofaro, Massimo,Evidente, Antonio,Superchi, Stefano,Scafato, Patrizia. "Synthesis and Herbicidal Activity against Buffelgrass (Cenchrus ciliaris) of (±)-3-deoxyradicinin". . . Retrieved 2019/09/09.