Coffee furanone (2-methyltetrahydrofuran-3-one) is a pleasant smelling liquid furan derivative which is a volatile constituent of the aroma complex of roasted coffee.[1] Coffee furanone is less odorous than furfuryl mercaptan, which with an odor threshold of 0.005 ppb was the first high impact aroma chemical, but has a very pleasant sweet caramel character, with some nuttiness.[2]
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| Names | |
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| Preferred IUPAC name
2-Methyloxolan-3-one | |
| Other names
2-Methyltetrahydrofuran-3-one; 2-Methyl-3-oxotetrahydrofuran; 2-Methyltetrahydro-3-furanone; Dihydro-2-methyl-3-furanone; 2-Methyldihydrofuran-3(2H)-one
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.019.715 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C5H8O2 | |
| Molar mass | 100.117 g·mol−1 |
| Density | 1.040 g/cm3 (20 °C) |
| Boiling point | 139 °C (282 °F; 412 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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Synthesis
editCoffee furanone was synthesized in 1963 by Wynberg via acid-catalyzed ring closure of β-alkoxy diazoketones.[3] Coffee furanone has also been prepared via the condensation of ethyl lactate and methyl acrylate in DMSO solution[4] and (under phase transfer conditions) in ionic liquids.[5] A related lactic acid synthesis was described as having the advantages of a simple process, high conversion rate, low pollution, and low cost.[6] This compound has also been prepared in acceptable yield via oxidative hydroxylation of the 2-acetylbutyrolactone.[7] Further approaches to the synthesis of coffee furanone involved the hydrolysis of the corresponding dithioketals[8] and the oxidation of 2-methyltetrahydrofuran employing lithium hypochlorite in the presence of ruthenium catalysts.[9]
Applications
editThe synthetic version of this natural flavorant and odorant is used in a variety of food and beverage applications, including coffee, nuts, cocoa, brandy, meat sauces and as a general food flavorant at a typical dosage (about 5-20 ppm), similar to the natural concentration (30 ppm) of coffee furanone in roasted coffee.[10][11]
References
edit- ^ M. A. Gianturco; Friedel, P.; Giammarino, A. S. (1964). "Volatile constituents of coffee. III. Structures of two heterocyclic compounds and the synthesis of tetrahydrofuranones". Tetrahedron. 20 (7): 1763–1772. doi:10.1016/s0040-4020(01)99177-x.
- ^ Nollet, Leo M. L., ed. (2012-07-20). Handbook of Meat, Poultry and Seafood Quality (1 ed.). Wiley. pp. 137–138. doi:10.1002/9781118352434. ISBN 978-0-470-95832-2.
- ^ H. Wynberg (1963). "Tetrahydrofuran-3-one, spirans, and dithienyls". Angewandte Chemie. 75 (10): 453. doi:10.1002/ange.19630751014.
- ^ M. A. Gianturco; Friedel, P.; Giammarino, A. S. (1964). "Volatile constituents of coffee. III. Structures of two heterocyclic compounds and the synthesis of tetrahydrofuranones". Tetrahedron. 20 (7): 1763–1772. doi:10.1016/s0040-4020(01)99177-x.
- ^ Xiaogeng Liu; Chen, Yousheng (2005). "Synthesis of 2-methyltetrafuran-3-one from ethyl lactate and methyl acrylate". Shipin Kexue (Beijing, China). 26 (5): 165–167.
- ^ Cunzhao Cheng "Synthesis method of natural flavoring 2-methyltetrahydrofuran-3-one", Zhuanli Shenging Gonkai Shuomingshu, CN Patent 2009:1544311 (2009)
- ^ Valentine Ragoussis; Lagouvardos, Dimitrios J.; Ragoussis, Nikitas (1998). "A short and efficient synthesis of 2-methyltetrahydrofuran-3-one". Synthetic Communications. 28 (22): 4273–4278. doi:10.1080/00397919809458708.
- ^ Bonkoch Tarnchompoo; Thebtaranonth, Yodhathai (1984). "A condensed synthesis of dihydro-3(2H)-furanone". Tetrahedron Letters. 25 (48): 5567–70. doi:10.1016/s0040-4039(01)81628-2.
- ^ Mario Bressan; Morvillo, Antonino; Romanello, Giorgio (1990). "Selective oxygenation of aliphatic ethers catalyzed by ruthenium(II) complexes". Inorganic Chemistry. 29 (16): 2976–2979. doi:10.1021/ic00341a024.
- ^ M. A. Gianturco; Friedel, P.; Giammarino, A. S. (1964). "Volatile constituents of coffee. III. Structures of two heterocyclic compounds and the synthesis of tetrahydrofuranones". Tetrahedron. 20 (7): 1763–1772. doi:10.1016/s0040-4020(01)99177-x.
- ^ R. Silwar; Kamperschroer, H.; Tressl, R. (1987). "Gas chromatographic-mass spectrometric study of roasted coffee aroma - quantitative determination of steam-volatile aroma constituents". Chemie, Mikrobiologie, Technologie der Lebensmittel. 10 (5–6): 176–187.