10449-66-8

Basic information

• Product Name: 5-methoxyfuran-2(5H)-one
• Synonyms: 5-methoxyfuran-2(5H)-one;2(5H)-Furanone, 5-methoxy-;5-Methoxy-2(5H)-furanone;5-Methoxy-2,5-dihydrofuran-2-one
• CAS NO: 10449-66-8
• Molecular Formula: C₅H₆O₃
• Molecular Weight: 114.09934
• EINECS: 233-933-9
• Mol File: 10449-66-8.mol

Chemical Properties

• Boiling Point: 256.2°Cat760mmHg
• Flash Point: 101.2°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 0.0156mmHg at 25°C
• Refractive Index: 1.465
• CAS DataBase Reference: 5-methoxyfuran-2(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methoxyfuran-2(5H)-one(10449-66-8)
• EPA Substance Registry System: 5-methoxyfuran-2(5H)-one(10449-66-8)

Safety Data

• Hazardous Substances Data: 10449-66-8(Hazardous Substances Data)

Usage

Uses

Used in Food Industry:
5-methoxyfuran-2(5H)-one is used as a flavoring agent for its sweet, caramel-like aroma and taste, enhancing the flavor profiles of various food products.
Used in Fragrance Industry:
In the fragrance industry, 5-methoxyfuran-2(5H)-one is utilized for its pleasant aroma, contributing to the creation of various scent compositions.
Used in Natural Preservation:
5-methoxyfuran-2(5H)-one is studied for its potential as a natural preservative in food products due to its antimicrobial properties, helping to extend shelf life and maintain product quality.
Regulatory Approval:
5-methoxyfuran-2(5H)-one is considered safe for use in food products and has received approval for use in the European Union and the United States, ensuring its compliance with safety standards in these regions.

InChI:InChI=1/C5H6O3/c1-7-5-3-2-4(6)8-5/h2-3,5H,1H3

Upstream product

• 98-01-1 furfural 
• 67-56-1 methanol 
• 186581-53-3 diazomethane 
• 1575-59-3 4-oxo-crotonic acid 
• 14032-66-7 5-hydroxy-2-(5H)-furanone 
• 6824-18-6 2,3,7-trioxa-bicyclo-<2.2.1>-hept-5-ene 
• 34171-46-5 (furan-2-yl)methyl benzoate 
• 78389-81-8 (Z)-4-Oxo-but-2-enoic acid methoxymethyl ester 
• 40981-57-5 3-bromo-5-methoxyfuran-2(5H)-one 
• 75-33-2 2-propanethiol 
• 157904-76-2 3,4-diaza-6-methoxy-1-oxa-2-oxo-bicyclo<3.3.0>octene 
• 108858-40-8 (3aS,4R,6aR)-4-Methoxy-3,3a,4,6a-tetrahydro-furo[3,4-c]pyrazol-6-one 
• 108858-40-8 (3aS,4S,6aR)-4-Methoxy-3,3a,4,6a-tetrahydro-furo[3,4-c]pyrazol-6-one 
• 98-00-0 (2-furyl)methyl alcohol 

Downstream Products

• 108858-40-8 (3aS,4R,6aR)-4-Methoxy-3,3a,4,6a-tetrahydro-furo[3,4-c]pyrazol-6-one 
• 108858-40-8 (3aS,4S,6aR)-4-Methoxy-3,3a,4,6a-tetrahydro-furo[3,4-c]pyrazol-6-one 
• 112968-75-9 (5R)-(L-menthyloxy)-2(5H)-furanone 
• 112968-75-9 (+)-(5S)-5-((+)-menthyl)oxy-2<5H>-furanone 
• 122079-46-3 (4S,5S)-4-(2,4-Dimethyl-phenylsulfanyl)-5-methoxy-dihydro-furan-2-one 
• 113003-58-0 6-methoxy-3-phenyl-3a,4,6,6a-tetrahydro-furo<3,4-d>isoxazol-4-one 
• 122079-42-9 5-methoxy-4-phenylthiobutyrolactone 
• 122079-42-9 4-phenylthio-3,4-dihydro-5-methoxy-2(5H)-furanone 
• 132990-36-4 2-((2R,3S,4R)-4-Diphenylphosphanyl-2-methoxy-5-oxo-tetrahydro-furan-3-yl)-2-methyl-propionic acid ethyl ester 
• 113033-28-6 (-)-(R)-5-methoxyfuran-2(5H)-one 
• 122079-44-1 (4R,5R)-4-(4-tert-Butyl-phenylsulfanyl)-5-methoxy-dihydro-furan-2-one 

Relevant articles and documents

(2+4)-Cycloaddition with singlet oxygen. 17O-investigation of the reactivity of furfuryl alcohol endoperoxide

In earlier work, the use of furfuryl alcohol as a specific singlet oxygen acceptor was proposed because of the high ratio between the rate constants of chemical reaction and physical quenching. In contrast to furfuryl aldehyde, a number of products are formed by this type II photooxidation of furfuryl alcohol. These products may be derived from the endoperoxide of furfuryl alcohol as a common intermediate. The present work focuses on the reactivity of this endoperoxide that was marked specifically by the use of 17O2 as a source for singlet oxygen. The analyses of the stable products, their yields and their labeling distribution reveal a strong solvent effect on the primary reaction pathways, and nucleophilic substitution reactions leading to hydroperoxide intermediates are dominant.

Total synthesis of a novel oxa-bowl natural product paracaseolide A via a 'putative' biomimetic pathway

A total synthesis of bioactive tetracyclic natural product paracaseolide A, embodying an architecturally unusual oxa-bowl framework, has been accomplished from commercially available 5-methyl-2-furfural. The key step involving a thermal [4+2]-dimerization of an appropriately crafted 5-methyl-3- alkenylbutenolide is shown to proceed in a stepwise manner.

Total synthesis of novel bioactive natural product paracaseolide A and analogues: Computational evaluation of a 'proposed' biomimetic Diels-Alder reaction

A short and generally applicable synthesis of bioactive tetracyclic natural product paracaseolide A has been accomplished employing a 'proposed' biomimetic Diels-Alder reaction as the key strategic step. The Diels-Alder precursors for this purpose were readily assembled through a versatile Suzuki coupling on preformed α-halo butenolides. The mechanistic aspects of the 'putative' biomimetic Diels-Alder reaction have been probed using computational methods, which suggest that this [4+2]-cycloaddition proceeds through a step-wise process and product profile is thermodynamically governed.

ANOMALOUS OZONOLYSIS PRODUCTS IN THE ADDITION OF SINGLET OXYGEN TO METHOXYMETHYLFURANS

The rearrangement of cyclobutadiene ozonides, related to "anomalous ozonolysis", has been elucidated.

PSEUDOESTERES Y DERIVADOS XXXIII. SINTESIS DE COMPUESTOS CICLOPROPANICOS POR FOTOLISIS DE PIRAZOLINAS OBTENIDAS POR CICLOADICION 1,3-DIPOLAR A LA 5-METOXI-2(5H)-FURANONA

By cycloaddition of 2-diazopropane to 5-methoxy-2(5H)-furanone (1) two regioisomeric 1-pyrazolines 3 and 4 are stereospecifically obtained.Both isomers give by photolysis, as major or sole compound, the same cyclopropane derivative 7.Hydrolysis of the bicyclic compound 7, followed by esterification, leads to cis open chain derivatives, which are appropiately functionalized for the synthesis of pyrethroids. a similar set of reactions, using diazomethane-d2 as dipolarophile, affords selectively deuterated cyclopropane derivatives.Palabras clave: Cicloadicion 1,3-dipolar, pirazolinas, fotolisis, ciclopropanos, piretroides.

AN EFFICIENT PHOTOREACTOR FOR USE OF LINEAR POLYMERIC PHOTOSENSITIZERS WITH PREPARATIVE PURPOSES

A photoreactor specially designed for preparative synthesis in homogeneous phase employing linear polymeric photosensitizers is described.The reactor allows the direct separation and subsequent reuse of the sensitizer by in situ ultrafiltration of the irradiated solution.The photo-oxidation with visible light of furfural, using as polymeric photosensitizer Rose Bengal covalently bound to linear polystyrene, has been chosen for the evaluation of the reactor as well as for the study of the behaviour of this particular photosensitizer when it is repeatedly used.The results of consecutive identical photo-oxidations indicate that, under the experimental conditions used, this sensitizer is photostable and its efficiency remains constant. Key words: Photoreactors, Photooxidations, Furfural, Polymeric photosensitizers.

Asymmetric 1,3-dipolar cycloadditions to 5-(R)-menthyloxy-2(5H)-furanone

Various diazo compounds, nitrile oxides, nitrones and azomethine ylides were examined in 1,3-dipolar cycloadditions to enantiomerically pure 5-(R)-menthyloxy-2(5H)-furanone 1a. Pyrazoline 9 was obtained in 100% c.y. as a mixture of 2 diastereoisomers in ratios up to 72:28, whereas pyrazoline 16 was obtained in 100% c.y. as a single enantiomer. Photochemically pyrazolines 9 and 10 have been converted to cyclopropanes 11 and 13. Under thermal conditions pyrazoline 9 is converted to 4-methyl-5-menthyloxy-2(5H)-furanone. Isoxazoles 21a-24a were obtained enantiomerically pure via nitrile oxide addition to 1a in 64-67% yield. Nitrone addition afforded isoxazolidines 27, 28 and 34 with complete anti-facial- and regiochemistry, but with endo-exo-selectivities up to 76%. Enantiomerically pure isoxazolidines were obtained in 25-75% yield. Pyrrolidine 36 was obtained diastereomerically pure in 81% c.y. Pyrrolidines 42 and 45, however, were obtained as diastereomeric mixtures in 37% resp. 6% yield.

Asymmetric Diels-Alder Reactions with 5-Menthyloxy-2(5H)-furanone

A new class of chiral dienophiles, 5-alkoxy-2(5H)-furanones, has been developed.Both enantiomers of 5-menthyloxy-2(5H)-furanone are readily available in enantiomerically pure form, starting from furfural and d- or l-menthol.Excellent diastereoselectivities (d.e. 99percent) are obtained in thermal Diels-Alder reactions with several cyclic and acyclic dienes.The use of silyl dienol ethers has resulted in new routes to enantiomerically pure cyclohexanones in a highly regioselective manner.

2,3,6-Trioxyfulvenes. Part 1. Synthesis of 1,4-Disubstituted-2,3,6-trioxyfulvenes.

A new strategy for the construction of the fulvene skeleton from acyclic precursors has been developed.The products obtained show three hydroxyl groups at C(2), C(3), and C(6), and two electron-withdrawing groups R (R = CO2Me, CN, NO2, and SO2-C6H4-p-Me) at C(1) and C(4).The keto-enol tautomerism of these compounds is discussed.The enol forms are maintained as methyl ethers.

ASYMMETRIC 1,4-ADDITIONS TO 5-ALKOXY-2(5H)-FURANONES. AN EFFICIENT SYNTHESIS OF (R)- AND (S)-3,4-EPOXY-1-BUTANOL

The synthesis of enantiomerically pure 5-menthyloxy-2(5H)-furanones is described as well as the diastereoselective 1,4-addition of thiols to these butenolides to yield new homochiral C4-synthons.Kinetic resolution of 5-methoxy-2(5H)-furanone, with an enantiomeric excess of 13percent, was achieved by cinchonidine catalysed thiophenol addition. The synthetic utility of the asymmetric thiol additions is illustrated in an efficient route to enantiomerically pure (R)- and (S)-3,4-epoxy-1-butanol.