Furaneol
Chemical compound
From Wikipedia, the free encyclopedia
Furaneol, or strawberry furanone, is an organic compound used in the flavor, perfume and cosmetics industry[2]. It is formally a derivative of furan. It is a white or colorless solid that is soluble in water and organic solvents.[3]
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| Names | |
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| IUPAC name
4-Hydroxy-2,5-dimethyl-3-furanone | |
Other names
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| Identifiers | |
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3D model (JSmol) |
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| Abbreviations | DMHF |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.020.826 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C6H8O3 | |
| Molar mass | 128.127 g·mol−1 |
| Melting point | 73 to 77 °C (163 to 171 °F; 346 to 350 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Odor and occurrence
Although possessed of a caramel-like odor at high concentrations, it exhibits a sweet strawberry aroma when dilute.[3] It is found in strawberries[4] and a variety of other fruits and it is partly responsible for the smell of fresh pineapple.[5] It is also an important component of the odours of buckwheat,[6] and tomato.[7] Furaneol accumulation during ripening has been observed in strawberries and can reach a high concentration of 37 μg/g.[8]
Furaneol acetate
The acetate ester of furaneol, also known as caramel acetate and strawberry acetate, is also popular with flavorists to achieve a fatty toffee taste and it is used in traces in perfumery to add a sweet gourmand note.[9]
Stereoisomerism
Furaneol has two enantiomers, (R)-(+)-furaneol and (S)-(−)-furaneol. The (R)-form is mainly responsible for the smell.[10]
-Furanol_V1.svg) (S)-configuration |
-Furanol_V1.svg) (R)-configuration |