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Furaneol Basic information Product Name: Furaneol Synonyms: CARMELAN;FEMA 3174;FURANEOL;HYDROXY DIMETHYL FURANONE;4-HYDROXY-2,5-DIMETHYL-3(2H)-FURANONE;4-HYDROXY-2,5-DIMETHYLFURAN-3(2H)-ONE;4-HYDROXY-2,5-DIMETHYL-FURAN-3-ONE;2,5-DIMETHYL-4-HYDROXY-2,3-DIHYDROFURAN-3-ONE CAS: 3658-77-3 MF: C6H8O3 MW: 128.13 EINECS: 222-908-8 Product Categories: API intermediates;Furan flavors;Furan&Benzofuran;Alphabetical Listings;C-D;Flavors and Fragrances Mol File: 3658-77-3.mol   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 n20/D 1.439 Fp >230 °F storage temp. 2-8°C pka 9.62±0.40(Predicted) form neat JECFA Number 1446 BRN 1281357 InChIKey INAXVXBDKKUCGI-UHFFFAOYSA-N CAS DataBase Reference 3658-77-3(CAS DataBase Reference) NIST Chemistry Reference 2,5-Dimethyl-4-hydroxy-3(2h)-furanone(3658-77-3) EPA Substance Registry System 4-Hydroxy-2,5-dimethyl-3(2H)furanone (3658-77-3)   Safety Information Hazard Codes Xn Risk Statements 22 Safety Statements 36-24/25 WGK Germany 3 RTECS LU3990000 F 10-23 HS Code 29321900 MSDS Information Provider Language 2,5-Dimethyl-4-hydroxy-3[2H]-furanone English SigmaAldrich English ACROS English   Furaneol Usage And Synthesis Description Furaneol 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 Properties Furaneol 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 Properties white to light yellow crystal powde Chemical Properties 4-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 Properties Furaneol has a sweet, fruity, strawberry, hot sugar, fruity caramel or “burnt pineapple” aroma. Occurrence Reported 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. Uses 2,5-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. Definition ChEBI: 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. Preparation Furaneol 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 values Detection: 0.03 to 60 ppb; aroma characteristics at 0.1%: sweet, slightly burnt brown caramellic, cotton candy with a savory nuance Taste threshold values Taste 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 name Furaneol® (Firmenich). Chemical Synthesis From dimethyl-3,4-dihydroxyfuran-2,5-dicarboxylate References Pickenhagen, 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 Raw materials Propylene glycol-->Ethyl lactate-->Crotononitrile (pract)-->4-Hyd