27538-09-6

Basic information

• Product Name: Homofuraneol
• Synonyms: homofuronol;FEMA 3623;METHYL FURANEOL;4-HYDROXY-5-ETHYL-2-METHYL-3(2H)-FURANONE;5-ethyl-4-hydroxy-2-methyl-3(2h)-furanone;5-ETHYL-4-HYDROXY-2-METHYL-FURAN-3-ONE;SOY FURANEOL;5-ethyl-4-hydroxy-2-methyl-3(2h)-furanon
• CAS NO: 27538-09-6
• Molecular Formula: C₇H₁₀O₃
• Molecular Weight: 142.15
• EINECS: 248-514-6
• Mol File: 27538-09-6.mol
• Article Data: 3

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.: Inert atmosphere,Room Temperature
• PKA: 9.58±0.40(Predicted)
• CAS DataBase Reference: Homofuraneol(CAS DataBase Reference)
• NIST Chemistry Reference: Homofuraneol(27538-09-6)
• EPA Substance Registry System: Homofuraneol(27538-09-6)

Safety Data

• WGK Germany: 3
• RTECS: LU4250000
• Hazardous Substances Data: 27538-09-6(Hazardous Substances Data)

Usage

Chemical Properties

2-Ethyl-4-hydroxy-5-methyl-3(2H)-furanone has a sweet, fruity, caramel, butterscotch odor.

Occurrence

Reported found in soy sauce, Swiss cheese and melon, coffee, shoyu, strawberry and pineapple.

Aroma threshold values

Detection: 20 ppb

Taste threshold values

Taste characteristics at 20 ppm: burnt, caramellic, sweet and fruity

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

Downstream Products

• 849585-22-4 LACTIC ACID 
• 600-15-7 2-Hydroxybutanoic acid 

Relevant articles and documents

Determination of 4-Hydroxy-2,5-dimethyl-3(2H)-furanone and 2(or 5)-Ethyl-4-hydroxy-5(or 2)-methyl-3(2H)-furanone in Pentose Sugar-Based Maillard Model Systems by Isotope Dilution Assays

The formation of 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF) and 2(or 5)-ethyl-4-hydroxy-5(or 2)-methyl-3(2H)-furanone (EHMF) from pentose sugars was studied in Maillard model systems. The amounts generated at 90°C for 1 h were determined by isotope dilution assay (IDA). The internal standards used for IDA, i.e., [13C2]HDMF and [2H3]EHMF, were prepared in good overall yields in three steps: addition of labeled acetaldehyde or propionaldehyde to tert-butyloxycarbonyl (Boc)-protected and lithiated 3-butyn-2-ol; oxidation of the Boc-protected diol with permanganate to 1,2-dione; and finally cyclization to the target molecules after removal of the protective groups under acidic conditions. Quantitative data confirmed previous findings that HDMF and EHMF are preferentially formed in the presence of glycine and L-alanine, respectively. The yields obtained were 2.6-5.1 μg of HDMF and 6.8-10 μg of EHMF per mmol pentose. Formation of both furanones was favored in phosphate-buffered solutions at pH 7 compared to pH 5, particularly in the presence of an excess of amino acid. These data are well in agreement with the previously proposed formation mechanism of HDMF and EHMF via Strecker-assisted chain elongation of the pentose moiety. However, both furanones were also produced to a lesser extent by sugar fragmentation-condensation reactions.

Process for making furanones

This deals with a process for making furanones having the formula: STR1 wherein R represents a hydrogen atom or the methyl or ethyl group.