67116-19-2

Basic information

• Product Name: 4-methyl-2H-Pyran-2,6(3H)-dione
• Synonyms: 4-methyl-2H-Pyran-2,6(3H)-dione;NSC 176171
• CAS NO: 67116-19-2
• Molecular Formula: C₆H₆O₃
• Molecular Weight: 126.11004
• Mol File: 67116-19-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 86 °C
• Boiling Point: 249.3°C at 760 mmHg
• Flash Point: 116.9°C
• Appearance: /
• Density: 1.239g/cm³
• Vapor Pressure: 0.0231mmHg at 25°C
• Refractive Index: 1.486
• CAS DataBase Reference: 4-methyl-2H-Pyran-2,6(3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methyl-2H-Pyran-2,6(3H)-dione(67116-19-2)
• EPA Substance Registry System: 4-methyl-2H-Pyran-2,6(3H)-dione(67116-19-2)

Safety Data

• Hazardous Substances Data: 67116-19-2(Hazardous Substances Data)

Usage

General Description

4-methyl-2H-pyran-2,6(3H)-dione, also known as maltol, is a naturally occurring organic compound found in a variety of plant sources, including pine needles, larch bark, and roasted malt. It is commonly used as a flavor enhancer, providing a sweet, caramel-like aroma and taste. Maltol is often used in the food and fragrance industries to impart a sweet, fruity flavor and aroma to products, such as baked goods, confections, and beverages. Its chemical structure and properties make it valuable as a food additive and fragrance ingredient, as well as in the development of pharmaceuticals and other products.

InChI:InChI=1/C6H6O3/c1-4-2-5(7)9-6(8)3-4/h2H,3H2,1H3

Upstream product

• 372-42-9 3-methylpent-2-enedioic acid 
• 52358-42-6 diethyl allene-1,3-dicarboxylate 
• 1610724-60-1 (E)-ethyl 2-(2-ethoxy-2-oxoethylidene)-4-oxocyclohexanecarboxylate 
• 90473-45-3 ethyl 7-(2-ethoxy-2-oxoethyl)-1,4-dioxaspiro[4.5]dec-7-ene-8-carboxylate 
• 90473-46-4 7-(carboxymethyl)-1,4-dioxaspiro[4.5]dec-7-ene-8-carboxylic acid 
• 105-50-0 diethyl 1,3-acetonedicarboxylate 
• 541-47-9 3-Methylbutenoic acid 
• 124-38-9 carbon dioxide 
• 73489-84-6 3-hydroxy-3-methyl-glutaric acid diethyl ester 
• 3385-34-0 ethyl isodehydroacetate 
• 25201-40-5 1,1-diallylethanol 
• 503-49-1 meglutol 
• 924-59-4 diethyl 3-methylpent-2-enedioate 
• 372-42-9 (E)-3-methylpent-2-enedioic acid 

Downstream Products

• 83860-26-8 13-cis-12-carboxyretinoic anhydride 
• 7470-42-0 3-acetyl-6-hydroxy-4-methyl-2H-pyran-2-one 
• 39149-97-8 (Z)-3-methylpent-2-ene-1,5-diol 
• 109019-19-4 4-(4-chloro-phenylhydrazono)-3-methyl-pentenedioic acid-anhydride 
• 109045-06-9 4-(2,5-dimethoxy-phenylhydrazono)-3-methyl-pentenedioic acid-anhydride 
• 81177-15-3 4-methyl-3-[(Ξ)-3-methyl-5t-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2t,4-dienylidene]-3H-pyran-2,6-dione 
• 481-74-3 Chrysophanol 
• 476-56-2 islandicin 
• 1610724-57-6 (1S,2R)-tert-butyl 5-methyl-2',3-dioxo-1-phenylspiro[cyclohex[4]ene-2,3'-indoline]-1'-carboxylate 
• 6247-73-0 S-(4-carboxy-3-methyl-but-2ξ-enoyl)-coenzyme-A 
• 108757-58-0 4-(2-carboxy-4,6-diiodo-phenylhydrazono)-3-methyl-pentenedioic acid-anhydride 
• 100135-37-3 4-(4-amino-phenylcarbamoyl)-3-methyl-cis-crotonic acid 
• 106270-13-7 3-methyl-4-o-tolylcarbamoyl-crotonic acid 
• 100718-36-3 4-(2,6-dimethyl-phenylcarbamoyl)-3-methyl-crotonic acid 

Relevant articles and documents

Carboxylative Cyclization of 2-Butenoates with Carbon Dioxide: Access to Glutaconic Anhydrides

Cyclic anhydrides are versatile synthons and functional comonomers. Herein, we reported an organic base-promoted carboxylative cyclization of 2-butenoates with carbon dioxide to produce important glutaconic anhydrides in good yields. This metal-free react

A Stereospecific Synthesis of (+/-)-Abscisic Acid

A convenient separation of (E)- and (Z)-3-methylpent-2-enedioic acids was devised, and it was shown that with acetyl chloride or thionyl chloride the (Z)-acid yields the cyclic anhydride while the (E)-acid forms 6-chloro-4-methylpyran-2-one.The chloropyranone by conventional chemistry gave 4-methyl-6-(2'-oxopropyl)pyran-2-one which condensed with 4-methylpent-3-en-2-one in the presence of pyrrolidine, yielding 4-methyl-6-(2',6',6'-trimethyl-4'-oxocyclohex-2'-enyl)pyran-2-one.Oxidation with selenium dioxide or t-butyl chromate then gave 6-(1'-hydroxy-2',6',6'-trimethyl-4'-oxocyclohex-2'-enyl)-4-methylpyran-2-one, which on reduction by lithium aluminium hydride and reoxidation afforded (+/-)-abscisic acid stereospecifically.

Biosynthetic Studies on Tajixanthone and Shamixanthone, Polyketide Hemiterpenoid Metabolites of Aspergillus variecolor

The biosynthesis of tajixanthone and related metabolites of Aspergillus variecolor has been studied by incorporation experiments with simple and advanced precursors labelled with the stable isotopes 13C, 2H and 18O.Tajixanthone is shown to be derived through ring cleavage of an octaketide-derived anthraquinone with introduction of two dimethylallyl moieties.From the results of isotopic labelling experiments and chemical studies on model compounds, an overall biosynthetic pathway is proposed and information on the mechanisms of interconversion of proposed intermediates is obtained.