27538-10-9

Basic information

• Product Name: Ethyl furaneol
• Synonyms: 2(or 5)-ethyl-4-hydroxy-5(or 2)-methyl- 3(2H)-furanone (Homofuraneol);2-ethyl-4-hydroxy-5-methyl-3(2h)-furanon;2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone (homofuraneol);3(2H)-Furanone, 2-ethyl-4-hydroxy-5-methyl-;4-hydroxy-2- or 5-ethyl-5- and 2-methyl-3(2H)-furanone;ethyl 4-hydroxy-5-methyl-3(2H)-furanone (homofuraneol);ethylhydroxymethylfuranone;ETHYL FURANEOL
• CAS NO: 27538-10-9
• Molecular Formula: C₇H₁₀O₃
• Molecular Weight: 156.18
• EINECS: 248-514-6
• Product Categories: Furan&Benzofuran;Alphabetical Listings;E-F;Flavors and Fragrances
• Mol File: 27538-10-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 248-249 °C(lit.)
• Flash Point: 184 °F
• Appearance: /
• Density: 1.137 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0121mmHg at 25°C
• Refractive Index: n20/D 1.512(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 9.62±0.40(Predicted)
• CAS DataBase Reference: Ethyl furaneol(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl furaneol(27538-10-9)
• EPA Substance Registry System: Ethyl furaneol(27538-10-9)

Safety Data

• Statements: 22
• Safety Statements: 23-36
• WGK Germany: 3
• RTECS: LU4250000
• Hazardous Substances Data: 27538-10-9(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 27538-10-9 differently. You can refer to the following data:
1. Colorless to light yellow liqui
2. 2-Ethyl-4-hydroxy-5-methyl-3(2H)-furanone has been identified in, for example, coffee and melon. The tautomer mixture is a clear slightly yellowish liquid, bp0.02 kPa 82–83°C, d204 1.137, n20D 1.511 with sweet, caramel, fruity, bread-like odor.

Preparation

One commercially applied synthesis is the condensation of 2-pentene nitrile with ethyl lactate followed by oxidation of the intermediate 4-cyano-5-ethyl-2-methyldihydro-3(2H)-furanone with monoperoxysulfate.

InChI:InChI=1/C7H10O3/c1-3-5-7(9)6(8)4(2)10-5/h4,9H,3H2,1-2H3

Upstream product

• 87-72-9 D-Xylose 
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• 80037-19-0 3-Ethyl-2,2'-dimethoxy-3'-methyl-[2,2']bioxiranyl 
• 948557-13-9 (2E)-2-ethylidene-4-hydroxy-5-methyl-3(2H)-furanone 
• 73920-09-9 2,5-Dibromo-heptane-3,4-dione 
• 56-40-6 glycine 

Relevant articles and documents

Dialkoxydiepoxyalkane: Zur Synthese von 4-Hydroxy-3(2H)-furanonen

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Nicotinamide-dependent Ene reductases as alternative biocatalysts for the reduction of activated alkenes

Four NAD(P)H-dependent non-flavin ene reductases have been investigated for their ability to reduce activated C=C bonds in an asymmetric fashion by using 20 structurally diverse substrates. In comparison with flavin-dependent Old Yellow Enzyme homologues, a higher degree of electronic activation was required, because the best activities were obtained with enals and nitroalkenes rather than enones and carboxylic esters. Although FaEO from Fragaria x ananassa (strawberry) and its homologue SlEO from Solanum lycopersicum (tomato) exhibited a narrow substrate spectrum, progesterone 5β-reductase (At5β-StR) from Arabidopsis thaliana (thale cress) and leukotriene B4 12-hydroxydehydrogenase (LTB4DH/PGR) from Rattus norvegicus (rat) appear to be promising candidates, in particular for the asymmetric bioreduction of open-chain enals, nitroalkenes and α,β-unsaturated γ-butyrolactones. Competing nitro reduction and non-enzymatic Weitz-Scheffer epoxidation were largely suppressed. Electronically activated alkenes have been stereoselectively reduced by using a single-enzyme-cofactor system employing nicotinamide-dependent non-flavin ene reductases. Copyright

Potential of gas chromatography-orthogonal acceleration time-of-flight mass spectrometry (GC-oaTOFMS) in flavor research

Gas chromatography-orthogonal acceleration time-of-flight mass spectrometry (GC-oaTOFMS) is an emerging technique offering a straightforward access to a resolving power up to 7000. This paper deals with the use of GC-oaTOFMS to identify the flavor components of a complex seafood flavor extract and to quantify furanones formed in model Maillard reactions. A seafood extract was selected as a representative example for complex food flavors and was previously analyzed using GC-quadrupole MS, leaving several molecules unidentified. GC-oaTOFMS analysis was focused on these unknowns to evaluate its potential in flavor research, particularly for determining exact masses, N-Methyldithiodimethylamine, 6-methyl-5-hepten-2-one, and tetrahydro-2,4-dimethyl-4H-pyrrolo- [2,1-d]-1,3,5-dithiazine were successfully identified on the basis of the precise mass determination of their molecular ions and their major fragments. A second set of experiments was performed to test the capabilities of the GC-oaTOFMS for quantification. Calibration curves were found to be linear over a dynamic range of 103 for the quantification of furanones. The quantitative data obtained using GC-oaTOFMS confirmed earlier results that the formation of 4-hydroxy-2,5-dimethyl-3(2H)-furanone was favored in the xylose/glycine model reaction and 2(or 5) -ethyl-4-hydroxy-5(or2)-methyl-3(2H)-furanone in the xylose/alanine model reaction. It was concluded that GC-oaTOFMS may become a powerful analytical tool for the flavor chemist for both identification and quantification purposes, the latter in particular when combined with stable isotope dilution assay.