| Identification | More | [Name]
4-Hydroxy-2,5-dimethyl-3(2H)furanone | [CAS]
3658-77-3 | [Synonyms]
2,5-DIMETHYL-4-HYDROXY-2,3-DIHYDROFURAN-3-ONE
2,5-DIMETHYL-4-HYDROXY-3(2H)-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
CARMELAN
FEMA 3174
FURANEOL
HYDROXY DIMETHYL FURANONE
STRAWBERRY FURANONE
2,5-dimethyl-4-hydroxy-(2H)-furan-3-one (furaneol)
2,5-dimethyl-4-hydroxy-2H-furan-3-one
2,5-dimethyl-4-hydroxy-3(2h)-furanon
2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF)
2,5-dimethyl-4-hydroxy-3(2H)-furanone (Furaneol)
3(2H)-Furanone, 2,5-dimethyl-4-hydroxy-
3(2H)-Furanone, 4-hydroxy-2,5-dimethyl-
4-Hydroxy-2,5-dimethyl
4-Hydroxy-2,5-dimethyl-3(2H)-furan-3-one
4-hydroxy-2,5-dimethyl-3(2h)-furanon | [EINECS(EC#)]
222-908-8 | [Molecular Formula]
C6H8O3 | [MDL Number]
MFCD00010706 | [Molecular Weight]
128.13 | [MOL File]
3658-77-3.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [Melting point ]
73-77 °C(lit.)
| [Boiling point ]
188 °C
| [density ]
1.049 g/mL at 25 °C
| [vapor pressure ]
0.81Pa at 25℃ | [FEMA ]
3174 | [refractive index ]
n20/D 1.439
| [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
neat | [pka]
9.62±0.40(Predicted) | [color ]
White | [Odor]
at 1.00 % in propylene glycol. sweet cotton candy caramel strawberry sugar | [Odor Type]
caramellic | [Water Solubility ]
176g/L at 20℃ | [JECFA Number]
1446 | [BRN ]
1281357 | [Stability:]
Light Sensitive, Temperature Sensitive | [InChIKey]
INAXVXBDKKUCGI-UHFFFAOYSA-N | [LogP]
0.95 at 20℃ | [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]
3658-77-3(EPA Substance) |
| Questions and Answers (Q&A) | Back Directory | [Description]
4-Hydroxy-2,5-dimethyl-3(2H) furanone 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.
| [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.
|
| Hazard Information | Back Directory | [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.
| [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 | [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 | [General Description]
4-Hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF, DMHF) is a caramel-like smelling compound, identified in Maillard reaction systems based on pentoses by GC-MS and GCMS/MS. Solubility data of DMHF in six different solvents over the temperature range from 283.15K to 313.15K under atmospheric pressure of 0.10 MPa has been examined by dynamic method. Separation of the enantiomers of DMHF by capillary electrophoretic method has been reported. Commercially it is synthesized from L-rhamnose. DMHF has been identified as acidic odorant in Thai premium fish sauce samples by aroma extract dilution analysis (AEDA). It is identified as key aroma compound in the distiller′s grains (DG) from wheat. It is reported as the main flavor compound in strawberries and its biosynthesis has been reported. HDMF has been found in various fruits such as pineapples strawberries and grapes, as well as in beef broth , roasted coffee, bread crust, roasted beef, roasted sesame seeds and stewed beef. | [Flammability and Explosibility]
Notclassified | [Trade name]
Furaneol® (Firmenich). | [Biochem/physiol Actions]
Taste at 0.10 to 1.0 ppm | [Synthesis]
From dimethyl-3,4-dihydroxyfuran-2,5-dicarboxylate
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