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

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

Uses

Used in Flavor and Fragrance Industry:
Homofuraneol is used as a flavoring agent for its sweet, fruity, and caramellic taste characteristics. It is particularly suitable for enhancing the flavor of food products, making them more appealing to consumers.
Used in the Food Industry:
Homofuraneol is used as an additive in the food industry to impart a pleasant and complex flavor profile to various products. Its natural occurrence in several food items makes it a preferred choice for enhancing their taste without the need for artificial additives.
Used in the Beverage Industry:
In the beverage industry, Homofuraneol is used to add a unique and rich flavor to drinks, particularly those that require a caramel or butterscotch taste. Its ability to provide a sweet and fruity aroma makes it an ideal choice for creating innovative and enticing beverage recipes.
Used in the Perfumery Industry:
Homofuraneol's distinct sweet, fruity, and caramellic odor makes it a valuable ingredient in the creation of perfumes and fragrances. It can be used to add depth and complexity to various scent compositions, making them more attractive and long-lasting.
Used in the Cosmetic Industry:
In the cosmetic industry, Homofuraneol can be used as a fragrance component in various products such as lotions, creams, and body washes. Its pleasant and complex aroma can enhance the overall sensory experience of these products, making them more appealing to consumers.

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.

Chemical and Enzymatic Syntheses of 6-Deoxyhexoses. Conversion to 2,5-Dimethyl-4-hydroxy-2,3-dihydrofuran-3-one (Furaneol) and Analogues

6-Deoxy-D-fructose 1-phosphate (6-deoxyF-1-P) forms when a solution containing D-fructose 1,6-diphosphate (FDP) and D-lactaldehyde is treated with the enzymes aldolase and triosephosphate isomerase (Scheme I).This transformation involves three reactions: aldolase-catalyzed cleavage of FDP to a mixture of dihydroxyacetone phosphate and D-glyceraldehyde phosphate, triosephosphate isomerase catalyzed equilibration of dihydroxyacetone phosphate and D-glyceraldehyde phosphate, and aldolase-catalyzed condensation of dihydroxyacetone phosphate and D-lactaldehyde to 6-deoxyF-1-P.An analogous process converts a mixture of FDP and L-lactaldehyde to 6-deoxysorbose 1-phosphate (6-deoxyS-1-P).Aldolase-catalyzed reaction of dihydroxyacetone phosphate, prepared separately, with D-lactaldehyde yields 6-deoxyF-1-P directly; similar reaction of dihydroxyacetone phosphate with α-hydroxybutyraldehyde yields a mixture of 6-methyl-6-deoxyhexose 1-phosphates.Acid-catalyzed hydrolysis of the sugar phosphates releases the corresponding free sugars.A mixture containing 6-deoxyhexoses is formed directly by base-catalyzed aldol condensation of dihydroxyacetone and D,L-lactaldehyde.Treatment of any of the 6-deoxyhexoses with acids generates 2,5-dimethyl-4-hydroxy-2,3-dihydrofuran-3-one (Furaneol, a flavor principle).Furaneol can also be prepared in moderate yields by hydrogenolysis of FDP and other hexose phosphates in alkaline media.

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.