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== Synthesis ==
== Synthesis ==
Coffee furanone has been prepared via the condensation of ethyl lactate and methyl acrylate in DMSO solution<ref>{{cite journal | author = M. A. Gianturco | title = Volatile constituents of coffee. III. Structures of two heterocyclic compounds and the synthesis of tetrahydrofuranones | journal = Tetrahedron | volume = 20 | pages = 1763–1772| year = 1964 |last2 = Friedel | first2 = P. | last3 = Giammarino | first3 = A. S. | issue = 7}}</ref> and (under phase transfer conditions) in ionic liquids.<ref>{{cite journal | author = Xiaogeng Liu | title = Synthesis of 2-methyltetrafuran-3-one from ethyl lactate and methyl acrylate. | journal = Shipin Kexue (Beijing, China) | volume = 26 | pages = 165–167| year = 2005 |last2 = Chen | first2 = Yousheng | issue = 5}}</ref> A related lactic acid synthesis was described as having the advantages of a simple process, high conversion rate, low pollution, and low cost.<ref> Cunzhao Cheng "Synthesis method of natural flavoring 2-methyltetrahydrofuran-3-one", Zhuanli Shenging Gonkai Shuomingshu, CN Patent 2009:1544311 (2009)</ref> This compound has also been prepared in acceptable yield via oxidative hydroxylation of the 2-acetylbutyrolactone.<ref>{{cite journal | author = Valentine Ragoussis | title = A short and efficient synthesis of 2-methyltetrahydrofuran-3-one | journal = Synthetic Communications | volume = 28 | pages = 4273–4278 | year = 1998 |last2 = Lagouvardos | first2 = Dimitrios J. | last3 = Ragoussis | first3 = Nikitas | issue = 22}}</ref> Further approaches to the synthesis of coffee furanone involved the hydrolysis of the corresponding dithioketals<ref>{{cite journal | author = Bonkoch Tarnchompoo | title = A condensed synthesis of dihydro-3(2H)-furanone | journal = Tetrahedron Letters | volume = 25 | pages = 5567–70 | year = 1984 |last2 = Thebtaranonth | first2 = Yodhathai | issue = 48}}</ref>and the oxidation of [[2-methyltetrahydrofuran]] employing [[lithium hypochlorite]] in the presence of ruthenium catalysts.<ref>{{cite journal | author = Mario Bressan | title = Selective oxygenation of aliphatic ethers catalyzed by ruthenium(II) complexes | journal = Inorganic Chemistry | volume = 29 | pages = 2976–2979 | year = 1990 |last2 = Morvillo | first2 = Antonino | last3 = Romanello | first3 = Giorgio | issue = 16}}</ref>
Coffee furnone was synthesized in 1963 by Wynberg via acid-catalyzed ring closure of β-alkoxy diazoketones.<ref>{{cite journal | author = H. Wynberg| title = Tetrahydrofuran-3-one, spirans, and dithienyls| journal = Angewandte Chemie| volume = 75(10)| pages =453| year = 1963}}</ref> Coffee furanone has also been prepared via the condensation of ethyl lactate and methyl acrylate in DMSO solution<ref>{{cite journal | author = M. A. Gianturco | title = Volatile constituents of coffee. III. Structures of two heterocyclic compounds and the synthesis of tetrahydrofuranones | journal = Tetrahedron | volume = 20 | pages = 1763–1772| year = 1964 |last2 = Friedel | first2 = P. | last3 = Giammarino | first3 = A. S. | issue = 7}}</ref> and (under phase transfer conditions) in ionic liquids.<ref>{{cite journal | author = Xiaogeng Liu | title = Synthesis of 2-methyltetrafuran-3-one from ethyl lactate and methyl acrylate. | journal = Shipin Kexue (Beijing, China) | volume = 26 | pages = 165–167| year = 2005 |last2 = Chen | first2 = Yousheng | issue = 5}}</ref> A related lactic acid synthesis was described as having the advantages of a simple process, high conversion rate, low pollution, and low cost.<ref> Cunzhao Cheng "Synthesis method of natural flavoring 2-methyltetrahydrofuran-3-one", Zhuanli Shenging Gonkai Shuomingshu, CN Patent 2009:1544311 (2009)</ref> This compound has also been prepared in acceptable yield via oxidative hydroxylation of the 2-acetylbutyrolactone.<ref>{{cite journal | author = Valentine Ragoussis | title = A short and efficient synthesis of 2-methyltetrahydrofuran-3-one | journal = Synthetic Communications | volume = 28 | pages = 4273–4278 | year = 1998 |last2 = Lagouvardos | first2 = Dimitrios J. | last3 = Ragoussis | first3 = Nikitas | issue = 22}}</ref> Further approaches to the synthesis of coffee furanone involved the hydrolysis of the corresponding dithioketals<ref>{{cite journal | author = Bonkoch Tarnchompoo | title = A condensed synthesis of dihydro-3(2H)-furanone | journal = Tetrahedron Letters | volume = 25 | pages = 5567–70 | year = 1984 |last2 = Thebtaranonth | first2 = Yodhathai | issue = 48}}</ref>and the oxidation of [[2-methyltetrahydrofuran]] employing [[lithium hypochlorite]] in the presence of ruthenium catalysts.<ref>{{cite journal | author = Mario Bressan | title = Selective oxygenation of aliphatic ethers catalyzed by ruthenium(II) complexes | journal = Inorganic Chemistry | volume = 29 | pages = 2976–2979 | year = 1990 |last2 = Morvillo | first2 = Antonino | last3 = Romanello | first3 = Giorgio | issue = 16}}</ref>


== Applications ==
== Applications ==

Revision as of 16:37, 25 November 2013

Coffee furanone
Names
IUPAC name
2-Methyldihydrofuran-3(2H)-one
Other names
2-Methyltetrahydrofuran-3-one; 2-Methyl-3-oxotetrahydrofuran; 2-Methyltetrahydro-3-furanone; Dihydro-2-methyl-3-furanone; 2-Methyloxolan-3-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.019.715 Edit this at Wikidata
  • InChI=1S/C5H8O2/c1-4-5(6)2-3-7-4/h4H,2-3H2,1H3
    Key: FCWYQRVIQDNGBI-UHFFFAOYSA-N
  • InChI=1/C5H8O2/c1-4-5(6)2-3-7-4/h4H,2-3H2,1H3
    Key: FCWYQRVIQDNGBI-UHFFFAOYAD
  • O=C1C(OCC1)C
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).

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]

Synthesis

Coffee furnone 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

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.[10][11]

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.
  2. ^ Leo M. L. Nollet, Terri Boylston, “Handbook of meat, poultry and seafood quality” page 137-138 (2007)
  3. ^ H. Wynberg (1963). "Tetrahydrofuran-3-one, spirans, and dithienyls". Angewandte Chemie. 75(10): 453.
  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.
  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.
  8. ^ Bonkoch Tarnchompoo; Thebtaranonth, Yodhathai (1984). "A condensed synthesis of dihydro-3(2H)-furanone". Tetrahedron Letters. 25 (48): 5567–70.
  9. ^ Mario Bressan; Morvillo, Antonino; Romanello, Giorgio (1990). "Selective oxygenation of aliphatic ethers catalyzed by ruthenium(II) complexes". Inorganic Chemistry. 29 (16): 2976–2979.
  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.
  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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