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Coffee furanone

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(Redirected from 2-Methyltetrahydrofuran-3-one)
Coffee furanone
Names
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
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.019.715 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H8O2/c1-4-5(6)2-3-7-4/h4H,2-3H2,1H3Key: FCWYQRVIQDNGBI-UHFFFAOYSA-N
  • InChI=1/C5H8O2/c1-4-5(6)2-3-7-4/h4H,2-3H2,1H3Key: FCWYQRVIQDNGBI-UHFFFAOYAD
SMILES
  • O=C1C(OCC1)C
Properties
Chemical formula C5H8O2
Molar mass 100.117 g·mol
Density 1.040 g/cm (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 , 100 kPa). Infobox references
Chemical compound

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. 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.

Synthesis

Coffee furanone was synthesized in 1963 by Wynberg via acid-catalyzed ring closure of β-alkoxy diazoketones. Coffee furanone has also been prepared via the condensation of ethyl lactate and methyl acrylate in DMSO solution and (under phase transfer conditions) in ionic liquids. A related lactic acid synthesis was described as having the advantages of a simple process, high conversion rate, low pollution, and low cost. This compound has also been prepared in acceptable yield via oxidative hydroxylation of the 2-acetylbutyrolactone. Further approaches to the synthesis of coffee furanone involved the hydrolysis of the corresponding dithioketals and the oxidation of 2-methyltetrahydrofuran employing lithium hypochlorite in the presence of ruthenium catalysts.

Applications

The 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.

References

  1. 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.
  2. 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.
  3. H. Wynberg (1963). "Tetrahydrofuran-3-one, spirans, and dithienyls". Angewandte Chemie. 75 (10): 453. doi:10.1002/ange.19630751014.
  4. 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.
  5. 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.
  6. Cunzhao Cheng "Synthesis method of natural flavoring 2-methyltetrahydrofuran-3-one", Zhuanli Shenging Gonkai Shuomingshu, CN Patent 2009:1544311 (2009)
  7. 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.
  8. 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.
  9. 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.
  10. 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.
  11. 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.
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