Chemistry:Filbertone

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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

  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. 
  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. 
  7. ↑ "(E)-filbertone". Scents and Flavors. https://scentsandflavors.com/database/9dbb5718-5fa8-4b99-b9bf-e0ec65a8753f. 
  8. ↑ "(+)-(E,S)-filbertone". Scents and Flavors. https://scentsandflavors.com/database/9dbb5726-79ec-4925-9350-73e32eb7100e. 
  9. ↑ "(-)-(E,R)-filbertone". Scents and Flavors. https://scentsandflavors.com/database/9dbb5726-70ab-49a5-8ce2-c4d644fb5928. 
  • Filbertone, Molecule of the Month, University of Bristol



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