Chemistry:Furaneol
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| IUPAC name
4-Hydroxy-2,5-dimethyl-3-furanone
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Other names
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3D model (JSmol)
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| Abbreviations | DMHF |
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PubChem CID
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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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| Infobox references | |
Furaneol, or strawberry furanone, is an organic compound used in the flavor and perfume industry. It is formally a derivative of furan. It is a white or colorless solid that is soluble in water and organic solvents.[2]
Odor and occurrence
Although malodorous at high concentrations, it exhibits a sweet strawberry aroma when dilute.[2] It is found in strawberries[3] and a variety of other fruits and it is partly responsible for the smell of fresh pineapple.[4] It is also an important component of the odours of buckwheat,[5] and tomato.[6] Furaneol accumulation during ripening has been observed in strawberries and can reach a high concentration of 37 μg/g.[7]
Stereoisomerism
Furaneol has two enantiomers, (R)-(+)-furaneol and (S)-(−)-furaneol. The (R)-form is mainly responsible for the smell.[8]
-Furanol_V1.svg) (S)-configuration |
-Furanol_V1.svg) (R)-configuration |
Biosynthesis
It is one of several products from the dehydration of glucose. Its immediate biosynthetic precursor is the glucoside, derived from dehydration of sucrose.[2]
References
- ↑ 4-Hydroxy-2,5-dimethyl-3(2H)-furanone at Sigma-Aldrich
- ↑ 2.0 2.1 2.2 Zabetakis, I.; Gramshaw, J. W.; Robinson, D. S. (1999). "2,5-Dimethyl-4-hydroxy-2H-furan-3-one and its derivatives: analysis, synthesis and biosynthesis - a review". Food Chemistry 65: 139–151. doi:10.1016/S0308-8146(98)00203-9.
- ↑ Ulrich, D.; Hoberg, Edelgard; Rapp, Adolf; Kecke, Steffen (1997). "Analysis of strawberry flavour – discrimination of aroma types by quantification of volatile compounds". Zeitschrift für Lebensmitteluntersuchung und -Forschung A 205 (3): 218–223. doi:10.1007/s002170050154. https://www.researchgate.net/publication/226927264.
- ↑ "Odor-active constituents in fresh pineapple (Ananas comosus [L.] Merr.) by quantitative and sensory evaluation". Biosci. Biotechnol. Biochem. 69 (7): 1323–30. 2005. doi:10.1271/bbb.69.1323. PMID 16041138.
- ↑ "Identification of buckwheat (Fagopyrum esculentum Moench) aroma compounds with GC-MS". Food Chemistry 112: 120–124. 2008. doi:10.1016/j.foodchem.2008.05.048.
- ↑ Buttery, Ron G.; Takeoka, Gary R.; Naim, Michael; Rabinowitch, Haim; Nam, Youngla (2001). "Analysis of Furaneol in Tomato Using Dynamic Headspace Sampling with Sodium Sulfate". Journal of Agricultural and Food Chemistry 49 (9): 4349–4351. doi:10.1021/jf0105236. PMID 11559136.
- ↑ Pérez, A. G. (2008) (in en). Fruit and Vegetable Flavour. Woodhead Publishing. ISBN 978-1-84569-183-7.
- ↑ Leffingwell,:John C. Chirality & Odour Perception – The Furaneols.
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