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
• Article Data: 14

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

General Description

5-methoxyfuran-2(5H)-one, also known as 5-methoxy-2(5H)-furanone, is a chemical compound with the molecular formula C5H6O3. It is a cyclic compound with a furan ring and a methoxy group attached to the 5th position of the ring. This chemical is commonly used as a flavoring agent in the food industry due to its sweet, caramel-like odor and taste. It is also used in the fragrance industry for its pleasant aroma. Additionally, this compound has antimicrobial properties and has been studied for its potential use as a natural preservative in food products. 5-methoxyfuran-2(5H)-one is considered safe for use in food products and has been approved for use in the European Union and the United States.

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

Upstream product

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

Downstream Products

• 34085-09-1 1,5-dihydro-5-hydroxy-2H-pyrrol-2-one 
• 35925-44-1 4,4′-(prop-2-ene-1,2-diyldisulfonyl)bis(methylbenzene) 
• 180576-33-4 4-isopropil-5-metoxi-2(5H)-furanona 
• 174655-89-1 4-formyl-5-methoxyfuran-2(5H)-one 
• 62594-18-7 4-bromo-5-methoxy-5H-furan-2-one 
• 592524-37-3 4-methoxy-3-methyl-3,3a,4,6a-tetrahydro-6H-furo[3,4-c]pyrazol-6-one 
• 592524-37-3 4-methoxy-3-methyl-3,3a,4,6a-tetrahydro-6H-furo[3,4-c]pyrazol-6-one 
• 592524-37-3 4-methoxy-3-methyl-3,3a,4,6a-tetrahydro-6H-furo[3,4-c]pyrazol-6-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 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.

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.