1073-96-7

Basic information

• Product Name: 4H-Pyran-4-one, 3,5-dihydroxy-2-methyl-
• Synonyms: 4H-Pyran-4-one, 3,5-dihydroxy-2-methyl-;3,5-DIHYDROXY-2-METHYL-4H-PYRAN-4-ONE;3,5-Dihydroxy-2-methyl-4-pyrone;5-Hydroxymaltol
• CAS NO: 1073-96-7
• Molecular Formula: C₆H₆O₄
• Molecular Weight: 142.11
• Mol File: 1073-96-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 158 °C
• Boiling Point: 346.2°C at 760 mmHg
• Flash Point: 154.5°C
• Appearance: /
• Density: 1.605g/cm³
• Vapor Pressure: 3.66E-06mmHg at 25°C
• Refractive Index: 1.639
• PKA: 9.24±0.10(Predicted)
• CAS DataBase Reference: 4H-Pyran-4-one, 3,5-dihydroxy-2-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-Pyran-4-one, 3,5-dihydroxy-2-methyl-(1073-96-7)
• EPA Substance Registry System: 4H-Pyran-4-one, 3,5-dihydroxy-2-methyl-(1073-96-7)

Safety Data

• Hazardous Substances Data: 1073-96-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 1, p. 111, 1971 DOI: 10.1080/00397917108081625

InChI:InChI=1/C6H6O4/c1-3-5(8)6(9)4(7)2-10-3/h2,7-8H,1H3

Upstream product

• 50-99-7 D-glucose 
• 66212-71-3 4-bromo-6-methoxy-2-methyl-2H-pyran-3(6H)-one 
• 66212-70-2 4-chloro-6-methoxy-2-methyl-2H-pyran-3(6H)-one 
• 58-86-6 D-xylose 
• 28564-83-2 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one 
• 56-40-6 glycine 
• 75253-89-3 6-Bromo-2-methoxy-4-methyl-3,7-dioxa-bicyclo[4.1.0]heptan-5-one 
• 144900-15-2 6-Chloro-2-methoxy-4-methyl-3,7-dioxa-bicyclo[4.1.0]heptan-5-one 

Downstream Products

• 144900-21-0 5-Benzyloxy-3-methoxymethoxy-2-methyl-pyran-4-one 
• 144900-20-9 5-benzyloxy-3-hydroxy-2-methyl-4H-pyran-4-one 
• 144900-19-6 3,5-dibenzyloxy-2-methyl-4H-pyran-4-one 

Relevant articles and documents

Isolation and identification of 5-hydroxymaltol, a mutagenic substance in glucose pyrolysate

This paper describes the isolation and identification of a mutagenic compound produced by the pyrolysis of glucose. The mutagenic activity of 5-hydroxymaltol is too weak to explain the mutagenic activity of the glucose pyrolysate. The authors are now attempting to identify other mutagens besides 5-hydroxymaltol in the glucose pyrolysate.

Identifying new volatile compounds in toasted oak

Toasting wood to be used in barrels for aging wine produces a great number of volatile and odiferous compounds. Three new volatile odorous compounds in toasted oak were identified. Analysis by high-performance gas chromatography of toasted oak extracts, combined with olfactory detection, enabled various chromatographic peaks with these specific aromas to be isolated. These same odors were simultaneously studied by heating glucose both with and without proline and phenylalanine. Aromatic compounds of interest were identified thanks to a combination of gas chromatography and both mass and infrared spectrometry. An analysis RMN was also used. Hydroxymaltol, 2,5-furanedicarbaldehyde, and furylhydroxymethyl ketone have been detected in extract of toasted oak wood. These molecules may be formed by direct pyrolysis of sugar or Maillard reactions. The acetylformoine was not detected in extract of toasted oak wood, whereas it was detected in heated extracts of various sugars and sugars mixtures with amino acids.

A CONVENIENT SYNTHESIS OF 3-HYDROXY-4H-PYRAN-4-ONE DERIVATIVES HAVING A HALO OR HYDROXY GROUP AT THE 5-POSITION

The reaction of 4,5-epoxy-4-halo-6-methoxy-2-methyltetrahydropyran-3-ones (4b, 5b) in acidic media was examined and the following results were found: The reaction of 4b or 5b with 1percent sulfuric acid afforded a mixture of 3,5-dihydroxy-4H-pyran-4-one (