50405-45-3

Usage

Uses

Used in Flavoring Industry:
4-Hydroxy-5,6-dimethylpyran-2-one is used as a flavoring agent for its vanilla-like aroma, enhancing the taste and appeal of food and beverages.
Used in Perfumery and Fragrance Industry:
4-Hydroxy-5,6-dimethylpyran-2-one is utilized as a fragrance ingredient in perfumes and body care products, adding a pleasant scent that is well-received by consumers.
Used in Biomedical Applications:
4-Hydroxy-5,6-dimethylpyran-2-one is studied for its potential antioxidant properties, which could be beneficial in the development of treatments and therapies that require antioxidant support.
Used in Pharmaceutical Applications:
Due to its antibacterial properties, 4-Hydroxy-5,6-dimethylpyran-2-one is being investigated for its potential use in the development of new antimicrobial drugs or as a component in existing formulations to combat bacterial infections.

Upstream product

• 75950-51-5 methyl 4-methyl-3,5-dioxohexanoate 
• 815-57-6 3-Methyl-2,4-pentanedione 
• 50496-43-0 ethyl 4-methyl-3,5-dioxohexanoate 
• 485-80-3 S-adenosyl-L-methionine 
• 1522-25-4 4-hydroxy-3-methylpent-3-en-2-one 
• 123-54-6 acetylacetone 
• 264881-69-8 5-hydroxy-4-methyl-3-oxo-hexanoic acid methyl ester 
• 30414-53-0 methyl propanoyl acetate 

Downstream Products

• 57103-53-4 colletopyrone 
• 121562-47-8 asnipyrone A 
• 1422048-22-3 6,7-dimethyl-3-methylene-2-phenyl-2H-furo[3,2-c]pyran-4(3H)-one 
• 1422048-34-7 (Z)-3-benzylidene-6,7-dimethyl-2H-furo[3,2-c]pyran-4(3H)-one 
• 1422048-45-0 3,6,7-trimethyl-2-phenyl-4H-furo[3,2-c]pyran-4-one 
• 1422048-42-7 (Z)-3-(2-fluorobenzylidene)-6,7-dimethyl-2H-furo[3,2-c]pyran-4(3H)-one 
• 1422048-30-3 2-(2-fluorophenyl)-6,7-dimethyl-3-methylene-2H-furo[3,2-c]-pyran-4(3H)-one 
• 1422048-41-6 (Z)-3-(4-fluorobenzylidene)-6,7-dimethyl-2H-furo[3,2-c]pyran-4(3H)-one 
• 1422048-29-0 2-(4-fluorophenyl)-6,7-dimethyl-3-methylene-2H-furo[3,2-c]-pyran-4(3H)-one 
• 84953-72-0 5,6-dimethylpyridine-2,4-diol 
• 28354-98-5 2,3,4,4-tetramethylcyclohex-2-en-1-one 

Relevant academic research and scientific papers

Enantiocontrolled total syntheses of breviones A, B, and C

Enantiocontrolled total syntheses of the breviones A, B, and C have been accomplished using a highly diastereoselective oxidative coupling of an α-pyrone with a tricyclic diene prepared from an optically pure Wieland-Miescher ketone derivative through the 7-endo-trig mode of acyl radical cyclization.

Enantioselective total synthesis of (-)-candelalides A, B and C: Potential Kvl.3 blocking immunosuppressive agents

Novel Kv1.3 blocking immunosuppressants, (-)-candelalides A, B and C, were efficiently synthesized for the first time in a convergent and unified manner starting from (+)-5-methyl-Wieland-Miescher ketone. The synthetic method involved the following key steps: i) a strategic [2,3]-Wittig rearrangement of a stannylmethyl ether to install the stereogenic center at C9 and the exo-methylene function at C8 present in the decalin portion; ii) a straightforward coupling of a transdecalin portion (BC ring) and a γ-pyrone moiety through the C16-C3′ bond to assemble the requisite carbon framework; and iii) a construction of a characteristic di or tetrahydropyran ring (A ring) by internal nucleophilic ring closure of a hydroxy aldehyde or a hydroxy epoxide. The present total synthesis has fully established the absolute configuration of these natural products.

Total synthesis of Herbarin A and B, determination of their antioxidant properties and toxicity in zebrafish embryo model

Herbarin A and B were isolated from the fungal strains of Cladosporium herbarum found in marine sponges Aplysina aerophoba and Callyspongia aerizusa. Total synthesis of Herbarin A and B was achieved by carrying out a multi-step synthesis approach, and the antioxidant properties were evaluated using FRAP assay. Toxicity of these compounds was determined using a zebrafish embryo model.

Regioselective functionalization of pyrones: Facile synthesis of 6-styrylpyrones via KHMDS-mediated aldol condensation

Herein, we disclose our efforts directed toward the synthesis of the kavalactone-based natural product penstyrylpyrone and other related 4-OMe-2-pyrones possessing diverse substituents at the 3-, 5-, and 7-positions. Further, a facile approach to access 6-styrylpyrones via the KHMDS-mediated regioselective aldol condensation of 2-pyrones is described with moderate substrate scope and good to high yields (58–80%). The utility of this methodology was exemplified by the stereoselective construction of desmethoxyyangonin, asnipyrone A, and asnipyrone B.

Expanding the structural diversity of polyketides by exploring the cofactor tolerance of an inline methyltransferase domain

A strategy for introducing structural diversity into polyketides by exploiting the promiscuity of an in-line methyltransferase domain in a multidomain polyketide synthase is reported. In vitro investigations using the highly-reducing fungal polyketide synthase CazF revealed that its methyltransferase domain accepts the nonnatural cofactor propargylic Se-adenosyl-l-methionine and can transfer the propargyl moiety onto its growing polyketide chain. This propargylated polyketide product can then be further chain-extended and cyclized to form propargyl-α pyrone or be processed fully into the alkyne-containing 4′-propargyl-chaetoviridin A.

Synthesis of methylenebis(4-hydroxy-2-pyrone) or methylenebis(4- hydroxycoumarin) derivatives by organic solid state reaction

Methylenebis(4-hydroxy-2-pyrone) or methylenebis(4-hydroxycoumarin) derivatives (5) have been synthesized from 4-hydroxy-2-pyrones or 4- hydroxycoumarin (3) with aldehydes (4) by organic solid state reaction.

An Improved Method for γ-Carboxylation of β-Diketones. Synthesis of 4-Alkyl-3,5-dioxohexanoic Acids and 5-Alkyl Derivatives of Triacetic Acid Lactone

γ-Carboxylation of β-diketones, 1, can be improved using samples containing 100percent of ketoenol tautomers, 3, prepared by mild hydrolysis of the corresponding copper(II) complexes 2.Cyclization of the so formed 4-alkyl-3,5-dioxohexanoic acids, 4, affords 5-alkyl-4-hydroxy-6-methyl-2-pyrones, 5.

Total synthesis of (±)-asteltoxin

A convergent synthesis of (±)-asteltoxin has been achieved in 16 steps (3.0% overall yield) from 3,4-dimethylfuran. The attachment of the triene pyrone side chain to the bis(tetrahydrofuran) skeleton proceeds by way of the addition of the Corey equivalent to anion 3 to the aldehyde 2 and a subsequent aldol condensation-dehydration reaction of pyrone 4.

Convenient Syntheses of Alkyl β-Resorcylate Derivatives

Syntheses of methyl 2,4-dihydroxy-6-methyl- (1a) and -3,6-dimethylbenzoates (1b) and methyl 2,4-dihydroxy-6-pentylbenzoate (1c) are described.Condensation reactions of dimethyl sodiomalonate with the dianion derived from pentane-2,4-dione or the dimerisation of the methyl acetoacetate dianion or the acetylation of the trianion derived from methyl 3,5,7-trioxo-octanoate gave (1a) (78percent) after work-up at pH 9.Analogous convenient, short, optimised syntheses of (1b and c) are given in detail.