Article · Wikipedia archive · Last revised May 28, 2026

Filbertone

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

Last revised
May 28, 2026
Read time
≈ 2 min
Length
467 w
Citations
9
Source
Wikipedia ↗
Filbertone
source ↗
Names
IUPAC name
(2E)-5-Methyl-2-hepten-4-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.133.148
UNII
  • 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).

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.34

The natural compound is a mixture of both enantiomers, and its composition can vary depending on the source.56 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

See also

References

References

  1. 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. 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. 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. 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. 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. 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. "(E)-filbertone". Scents and Flavors. Scents and Flavors. Retrieved 1 April 2026.
  8. "(+)-(E,S)-filbertone". Scents and Flavors. Scents and Flavors. Retrieved 1 April 2026.
  9. "(-)-(E,R)-filbertone". Scents and Flavors. Scents and Flavors. Retrieved 1 April 2026.
External links
  • Filbertone, Molecule of the Month, University of Bristol