Filbertone

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Filbertone
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Names
IUPAC name
(2E)-5-Methyl-2-hepten-4-one
Identifiers
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3D model (JSmol)
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  • InChI=1S/C8H14O/c1-4-6-8(9)7(3)5-2/h4,6-7H,5H2,1-3H3/b6-4+
    Key: ARJWAURHQDJJAC-GQCTYLIASA-N
  • InChI=1/C8H14O/c1-4-6-8(9)7(3)5-2/h4,6-7H,5H2,1-3H3/b6-4+
    Key: ARJWAURHQDJJAC-GQCTYLIABX
  • O=C(/C=C/C)C(C)CC
Properties
C8H14O
Molar mass 126.199 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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Filbertone is the principal flavor compound of hazelnuts.[1] It is used in perfumery and is designated as generally recognized as safe (GRAS) for use in food products.[2]

Because filbertone is found in hazelnut oil, its presence can be used to detect the adulteration of olive oil with less expensive hazelnut oil.[3][4]

The natural compound is a mixture of both enantiomers, and its composition can vary depending on the source.[5][6] Whilst the aroma of the racemate is described as "hazelnut, nutty",[7] the dextro enantiomer (+)-(E,S)-filbertone is described as "hazelnut, metallic, fatty, nutty"[8] and the laevo enantiomer (-)-(E,R)-filbertone is "hazelnut, soft, buttery, chocolate, metallic, nutty".[9]

See also

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content.Jauch, Johann; Schmalzing, Dieter; Schurig, Volker; Emberger, Roland; Hopp, Rudolf; Köpsel, Manfred; Silberzahn, Wilhelm; Werkhoff, Peter (1989). "Isolation, Synthesis, and Absolute Configuration of Filbertone - the Principal Flavor Component of the Hazelnut". Angewandte Chemie International Edition in English. 28 (8): 1022. doi:10.1002/anie.198910221.
  2. ^ Page Module:Citation/CS1/styles.css has no content.Zarbin, Paulo H.G.; Yonashiro, Massami; Perissini Jr, Waldir (1998). "An Alternative Route for the Synthesis of (E)-(+)-5(S)-Methylhept-2-en-4-one (Filbertone)". Journal of the Brazilian Chemical Society. 9 (6): 583. doi:10.1590/S0103-50531998000600011.
  3. ^ Page Module:Citation/CS1/styles.css has no content.Ruiz Del Castillo, María Luisa; Caja, María del Mar; Herraiz, Marta; Blanch, Gracia P. (1998). "Rapid Recognition of Olive Oil Adulterated with Hazelnut Oil by Direct Analysis of the Enantiomeric Composition of Filbertone". Journal of Agricultural and Food Chemistry. 46 (12): 5128. doi:10.1021/jf9807014.
  4. ^ Page Module:Citation/CS1/styles.css has no content.Flores, Gema; Ruiz Del Castillo, Maria Luisa; Herraiz, Marta; Blanch, Gracia Patricia (2006). "Study of the adulteration of olive oil with hazelnut oil by on-line coupled high performance liquid chromatographic and gas chromatographic analysis of filbertone". Food Chemistry. 97 (4): 742. doi:10.1016/j.foodchem.2005.06.008.
  5. ^ Page Module:Citation/CS1/styles.css has no content.Ruiz Del Castillo, M. L.; Gómez Caballero, E.; Blanch, G. P.; Herraiz, M. (2002). "Enantiomeric composition of filbertone in hazelnuts and hazelnut oils from different geographical origins". Journal of the American Oil Chemists' Society. 79 (6): 589. doi:10.1007/s11746-002-0527-1. hdl:10261/241822. S2CID 94014818.
  6. ^ Page Module:Citation/CS1/styles.css has no content.Güntert, Matthias; Emberger, Roland; Hopp, Rudolf; Köpsel, Manfred; Silberzahn, Wilhelm; Werkhoff, Peter (1991). "Chirospecific analysis in flavor and essential oil chemistry Part A. Filbertone ? The character impact compound of hazel-nuts". Zeitschrift für Lebensmittel-Untersuchung und -Forschung. 192 (2): 108. doi:10.1007/BF01202621. S2CID 92237130.
  7. ^ Page Module:Citation/CS1/styles.css has no content."(E)-filbertone". Scents and Flavors. Scents and Flavors. Retrieved 1 April 2026.
  8. ^ Page Module:Citation/CS1/styles.css has no content."(+)-(E,S)-filbertone". Scents and Flavors. Scents and Flavors. Retrieved 1 April 2026.
  9. ^ Page Module:Citation/CS1/styles.css has no content."(-)-(E,R)-filbertone". Scents and Flavors. Scents and Flavors. Retrieved 1 April 2026.
  • Filbertone, Molecule of the Month, University of Bristol
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