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

Description

Ethyl furaneol, also known as 2-Ethyl-4-hydroxy-5-methyl-3(2H)-furanone, is a colorless to light yellow liquid with a sweet, caramel, fruity, and bread-like odor. It is a tautomer mixture with a boiling point of 82-83°C at 0.02 kPa, a density of 1.137 g/cm3, and a refractive index of 1.511. Ethyl furaneol is commonly found in various natural sources, such as coffee and melon, and is known for its distinct and pleasant aroma.

Uses

Used in Flavor and Fragrance Industry:
Ethyl furaneol is used as a flavoring agent for its sweet, caramel, fruity, and bread-like odor. It is widely utilized in the food and beverage industry to enhance the taste and aroma of various products, such as soft drinks, baked goods, and confectionery items.
Used in Perfumery:
In the perfumery industry, Ethyl furaneol is used as a fragrance ingredient to add a pleasant and complex scent to perfumes and other fragrance products. Its unique aroma profile makes it a valuable addition to the formulation of various perfumes and colognes.
Used in Cosmetics:
Ethyl furaneol is also used in the cosmetics industry as a component in the creation of various cosmetic products, such as lotions, creams, and shampoos. Its pleasant odor and ability to enhance the sensory experience of these products make it a popular choice for cosmetic manufacturers.
Used in the Pharmaceutical Industry:
In the pharmaceutical industry, Ethyl furaneol can be used as an additive to improve the taste and aroma of certain medications, making them more palatable for patients. Additionally, its unique chemical properties may have potential applications in the development of new drugs or drug delivery systems.

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

• 58-86-6 D-xylose 
• 56-41-7 L-alanin 
• 56-40-6 glycine 
• 948557-13-9 (2E)-2-ethylidene-4-hydroxy-5-methyl-3(2H)-furanone 
• 73920-09-9 2,5-Dibromo-heptane-3,4-dione 
• 87-72-9 D-Xylose 
• 80037-19-0 3-Ethyl-2,2'-dimethoxy-3'-methyl-[2,2']bioxiranyl 

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.