2298-99-9

Usage

Uses

Used in Cosmetic Industry:
2,6-Dimethyl-5-hydroxy-4H-pyran-4-one is used as a skin conditioning agent for its ability to improve skin texture and hydration, as well as a fragrance ingredient for its sweet, fruity aroma, enhancing the sensory experience of cosmetic products.
Used in Food Industry:
In the food industry, 2,6-Dimethyl-5-hydroxy-4H-pyran-4-one is used as a flavoring agent to impart a pleasant taste and aroma to various food products, contributing to the overall flavor profile and consumer appeal.
Used in Pharmaceutical Industry:
2,6-Dimethyl-5-hydroxy-4H-pyran-4-one is utilized as an intermediate in the synthesis of various drugs, playing a crucial role in the development of new pharmaceutical compounds.
Used in Antioxidant and Antimicrobial Applications:
Due to its antioxidant and antimicrobial properties, 2,6-Dimethyl-5-hydroxy-4H-pyran-4-one is employed in a wide range of applications to prevent oxidation and microbial growth, ensuring the stability and safety of various products.
It is important to handle 2,6-Dimethyl-5-hydroxy-4H-pyran-4-one with care, as it can be harmful if ingested or inhaled and may cause skin and eye irritation. Proper safety measures should be taken during its use to minimize potential risks.

InChI:InChI=1/C7H8O3/c1-4-3-6(8)7(9)5(2)10-4/h3,9H,1-2H3

Upstream product

• 14003-15-7 2-(1-hydroxyethyl)-5-methylfuran 
• 78139-28-3 6-methoxy-2,6-dimethyl-5,6-dihydropyran-3(4H)-one 
• 644-46-2 allomaltol 
• 7559-81-1 chlorokojic acid 
• 73707-43-4 6,6-ethylenedioxy-3-methyleneheptan-2-ol 
• 67074-01-5 6,6-ethylenedioxy-3-methyleneheptan-2-one 
• 78139-26-1 2-methoxy-2,6-dimethyl-5-methylene-3,4,5,6-tetrahydro-2H-pyran 
• 22639-17-4 2-hydroxymethyl-3-hydroxy-6-methyl-pyran-4(1H)-one 

Relevant academic research and scientific papers

Synthesis of 5,6-Dihydropyran-3(4H)-one

The synthesis and oxidation of the title compound (8b) are described.Attempted cyclization of 3-methyleneheptane-2,6-diol (2a) and 2,6-diacetoxyheptan-3-one (5) afforded furan derivatives (3) and (7), respectively. 6,6-Ethylenedioxy-3-methyleneheptan-2-ol (10) was successively cyclized, methoxylated, and ozonized to give 5,6-dihydropyran-3(4H)-one (8b), which yielded 6-methylmaltol (13) on treatment with selenium dioxide.

Drug for ameliorating brain diseases

The present invention discloses a drug for ameliorating brain diseases which comprises as an active ingredient a compound represented by the following formula (1): STR1 or a salt thereof. Because of inhibiting a decrease in brain neurons and promoting branching of neurites, this drug is efficacious in the prevention and treatment of dementia, etc. in association with degeneration and sloughing of brain neurons.

Synthesis, physicochemical properties, and biological evaluation of hydroxypyranones and hydroxypyridinones: Novel bidentate ligands for cell- labeling

The synthesis of a range of hydroxypyranones and hydroxypyridinones with potential for the chelation of indium(III) is described. The crystal structures of two of the indium complexes are presented. The distribution coefficients of the ligands and the corresponding iron(III), gallium(III), and indium(III) complexes are reported. Good linear relationships between the distribution coefficients of the iron and gallium complexes and iron and indium complexes were obtained. In contrast a nonlinear relationship was obtained between the distribution coefficient of the free ligand and the distribution coefficient of the three groups of complexes. This latter relationship was used to identify compounds with optimal cell labeling properties. Two such compounds both 6-(alkoxymethyl)-3-hydroxy-4H-pyran-4- ones have been compared with tropolone for their ability to label human leucocytes with 111In. The leucocyte labeling efficiencies of the selected ligands were greater and the in-vitro plasma stabilities were similar to that of 111In-tropolonate. These results suggest that the new bidentate ligands may offer advantages over those currently used for cell-labeling.

Tobacco Smoke Chemistry. 4. A Mass Spectral Study of Alkyl 3-Hydroxy-4-pyrones

3-Hydroxy-4-pyrone and a series of C-alkylated 3-hydroxy-4-pyrones have been synthesized and their behaviour under electron impact investigated.The fragmentation pathways were elucidated with the aid of accurate mass measurements, metastable ion analysis and deuterium labelling.All compounds examined gave a detectable molecular ion which undergoes a retro Diels-Alder type process accompanied by hydrogen transfer to give characteristic ions, which in many cases allow differentiation of positional isomers.Loss of carbon monoxide is encountered from several ions, but to any substantial extent from the molecular ions only in the cases of 3-hydroxy-4-pyrone and 5-hydroxy-2-methyl-4-pyrone.Instead, the more general fragmentation routes involve extrusion of a hydrogen or an alkyl radical from the molecular ion prior to the elimination of carbon monoxide.When the alkyl substituent in 2-alkyl-3-hydroxy- or 2-alkyl-5-hydroxy-4-pyrone has three or more consecutive carbons the molecular ion loses an alkene fragment by a McLafferty type of reaction.The even mass ions formed by this process constitute the base peak in most spectra of this type.Another rearrangement reaction giving even mass ions after loss of an alkene fragment, occurs when the alkyl substituent in the 2-alkyl-3-hydroxy-4-pyrones is branched at the α-carbon.Moreover, γ-bond cleavage of the alkyl side chain vicinal to the hydroxy group becomes important due to anchimeric assistance by the hydroxy group.

Preparation of gamma-pyrones

2-METHYL-3-HYDROXY-4H-pyran-4-one is prepared by contacting 1(2-furyl)-1-ethanol in aqueous solution with two equivalents of a halogen oxidant at room temperature and then heating until the hydrolysis of the formed 4-halo-dihydropyran intermediate is substantially complete. Other valuable related gamma-pyrones are prepared in analogous manner from appropriate alcohols.