ChemicalBook > Product Catalog > Flavors and fragrances > Synthetic fragrances > Oxygen-containing heterocyclic compounds > Furan and pyran > Furaneol
Furaneol Chemical Properties
- Melting point:73-77 °C(lit.)
- Boiling point:188 °C
- Density 1.049 g/mL at 25 °C
- FEMA 3174 | 4-HYDROXY-2,5-DIMETHYL-3(2H)-FURANONE
- refractive index n
- Flash point:>230 °F
- storage temp. 2-8°C
- form neat
- JECFA Number1446
- BRN 1281357
- CAS DataBase Reference3658-77-3(CAS DataBase Reference)
- NIST Chemistry Reference2,5-Dimethyl-4-hydroxy-3(2h)-furanone(3658-77-3)
- EPA Substance Registry System4-Hydroxy-2,5-dimethyl-3(2H)furanone (3658-77-3)
Furaneol Usage And Synthesis
- DescriptionFuraneol is a very important aroma chemical and is a key flavoring compound found in many kinds of fruits. It can be chemically formed through different carbohydrates during the Mainlard reaction. It can also be synthesized by yeast, bacteria and plants and play some physiological effects. Study has shown that it can suppress the phosphorylation of cAMP response element binding protein, underlying its potential role as an effective inhibitor of hyperpigmentation. It also has the potential to become an effective antimicrobial agent for human beings.
- Chemical PropertiesFuraneol is a constituent of pineapple and strawberry aroma and is also found in other foods. It forms colorless crystals (mp 77–79°C) with a relatively weak, nonspecific odor. Dilute solutions develop a pineapple, strawberrylike odor.
- Chemical Propertieswhite to light yellow crystal powde
- Chemical Properties4-Hydroxy-2,5-dimethyl-3(2H)-furanone has a fruity caramel or "burnt pineapple" aroma. May be synthesized from dimethyl- 3,4-dihyroxyfuran-2,5-dicarboxylate.
- Chemical PropertiesFuraneol has a sweet, fruity, strawberry, hot sugar, fruity caramel or “burnt pineapple” aroma.
- OccurrenceReported found in guava, grapes, pineapple, raspberry, strawberry fruit and jam, rye bread, Swiss cheese, boiled beef, beer, cocoa, coffee, tea, filberts, almonds, oatmeal, Arctic bramble, yellow passion fruit, mango, shoyu, fermented soy sauce, litchi, malt and Cape gooseberry.
- Uses2,5-Dimethyl-4-hydroxy-3(2H)-furanone is a component of meat essence composition. 2,5-Dimethyl-4-hydroxy-3(2H)-furanone is used in the flavor and perfume industry due to its sweet strawberry aroma.
- DefinitionChEBI: A member of the class of furans that is 2,5-dimethylfuran carrying additional oxo and hydroxy groups at positions 3 and 4 respectively. It has been found particularly in strawberries and other such fruits.
- PreparationFuraneol can be prepared by cyclization of hexane-2,5-diol-3,4-dione in the presence of an acidic catalyst.The dione is the ozonization product of 2,5- hexynediol, which is obtained by ethynylation of acetaldehyde.
In another process, a dialkyl ??-methyldiglycolate (formed from an alkyl lactate and an alkyl monochloroacetate) is reacted with dialkyl oxalate in the presence of a sodium alkoxide and dimethylformamide. The reaction product is cyclized, alkylated, hydrolyzed, and decarboxylated.In another process, a dialkyl ??-methyldiglycolate (formed from an alkyl lactate and an alkyl monochloroacetate) is reacted with dialkyl oxalate in the presence of a sodium alkoxide and dimethylformamide. The reaction product is cyclized, alkylated, hydrolyzed, and decarboxylated .
- Aroma threshold valuesDetection: 0.03 to 60 ppb; aroma characteristics at 0.1%: sweet, slightly burnt brown caramellic, cotton candy with a savory nuance
- Taste threshold valuesTaste characteristics at 0.10 to 1.0 ppm: sweet caramellic cooked meaty and fruity nuances
- Synthesis Reference(s)The Journal of Organic Chemistry, 57, p. 5023, 1992 DOI: 10.1021/jo00044a047
Synthesis, p. 377, 1987
- Trade nameFuraneol® (Firmenich).
- Chemical SynthesisFrom dimethyl-3,4-dihydroxyfuran-2,5-dicarboxylate
- ReferencesPickenhagen, Wilhelm, et al. "Estimation of 2,5-dimethyl-4-hydroxy-3(2H)-furanone (FURANEOLA®) in cultivated and wild strawberries, pineapples and mangoes." Journal of the Science of Food & Agriculture 32.11(2010):1132-1134.
Farine, Jean Pierre, et al. "4-Hydroxy-5-methyl-3(2H)-furanone and 4-Hydroxy-2,5-dimethyl-3(2H)-furanone, Two Components of the Male Sex Pheromone of Eurycotis floridana (Walker) (Insecta, Blattidae, Polyzosteriinae)." Bioscience Biotechnology & Biochemistry 57.12(2014):2026-2030.
Schwab, W. "Natural 4-hydroxy-2,5-dimethyl-3(2H)-furanone (Furaneol®). " Molecules 18.6(2013):6936-51.
Furaneol Preparation Products And Raw materials
- 3-Methylfuran WILDSTRAWBERRY Ethyl 3-methyl-3-phenylglycidate Furazolidone Dimethyl sulfide Dimethyl phthalate Dimethyl sulfoxide Fraision butyrate Homofuraneol Furaneol acetate 4-Methoxy-2,5-dimethyl-3(2H)-furanone Furaneol N,N-Dimethylformamide 4'-Hydroxyacetophenone 2,5-Furandicarboxylic acid Acetone oxime ETHANE Dimethyl fumarate
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