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 foods.

• ^{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.}
• ^{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.}

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

• ^{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.}
• ^{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}.

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

• ^{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.}
• ^{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.}

Literature

• Filbertone, (2E)-5-methyl-2-hepten-4-one, regulates thermogenesis and lipid metabolism in skeletal muscle of a high-fat diet fed micePublication Name: Applied Biological ChemistryPublication Date: 2023DOI: 10.1186/s13765-023-00783-5
• Effects of enzyme treatment on volatile and non-volatile compounds in dried green tea leavesPublication Name: Food Science and BiotechnologyPublication Date: 2022-03-15PMID: 35529688DOI: 10.1007/s10068-022-01063-6
• RIFM fragrance ingredient safety assessment, 5-methyl-2-hepten-4-one, CAS Registry Number 81925-81-7Publication Name: Food and chemical toxicology : an international journal published for the British Industrial Biological Research AssociationPublication Date: 2022-03PMID: 35218917DOI: 10.1016/j.fct.2022.112879
• Filbertone Protects Obesity-induced Hypothalamic Inflammation by Reduction of Microglia-mediated Inflammatory ResponsesPublication Name: Biotechnology and Bioprocess EngineeringPublication Date: 2021-02-24DOI: 10.1007/s12257-020-0220-5
• Hazelnut (Corylus avellana) OilPublication Name: Fruit Oils: Chemistry and FunctionalityPublication Date: 2019DOI: 10.1007/978-3-030-12473-1_10
• Evolution of potent odorants within the volatile metabolome of high-quality hazelnuts (Corylus avellana L.): evaluation by comprehensive two-dimensional gas chromatography coupled with mass spectrometryPublication Name: Analytical and Bioanalytical ChemistryPublication Date: 2018-01-09PMID: 29313080DOI: 10.1007/s00216-017-0832-6
• Biosynthesis of Plant-Derived OdorantsPublication Name: Springer Handbook of OdorPublication Date: 2017DOI: 10.1007/978-3-319-26932-0_2
• Comprehensive two-dimensional gas chromatography and food sensory properties: potential and challengesPublication Name: Analytical and Bioanalytical ChemistryPublication Date: 2014-10-30PMID: 25354891DOI: 10.1007/s00216-014-8248-z
• Influence of E-smoking liquids on human periodontal ligament fibroblastsPublication Name: Head & Face MedicinePublication Date: 2014-09-15PMID: 25224853DOI: 10.1186/1746-160x-10-39
• Evaluation of Process Parameters Governing the Aroma Generation in Three Hazelnut Cultivars (Corylus avellana L.) by Correlating Quantitative Key Odorant Profiling with Sensory EvaluationPublication Name: Journal of Agricultural and Food ChemistryPublication Date: 2013-05-21PMID: 23663154DOI: 10.1021/jf4008086
• Influence of water on the generation of Strecker aldehydes from dry processed foodsPublication Name: European Food Research and TechnologyPublication Date: 2009-11-05DOI: 10.1007/s00217-009-1169-y
• Determination of filbertone in spiked olive oil samples using headspace-programmed temperature vaporization-gas chromatography–mass spectrometryPublication Name: Analytical and Bioanalytical ChemistryPublication Date: 2009-04-27PMID: 19396589DOI: 10.1007/s00216-009-2795-8
• Aroma CompoundsPublication Name: Food ChemistryPublication Date: 2009DOI: 10.1007/978-3-540-69934-7_6
• AromastoffePublication Name: LebensmittelchemiePublication Date: 2008DOI: 10.1007/978-3-540-73202-0_6
• Free and Esterified 4,4′-dimethylsterols in Hazelnut Oil and their Retention During Refining ProcessesPublication Name: Journal of the American Oil Chemists’ SocietyPublication Date: 2007-01-03DOI: 10.1007/s11746-006-1025-1
• The detection of the presence of hazelnut oil in olive oil by free and esterified sterolsPublication Name: European Food Research and TechnologyPublication Date: 2006-02-24DOI: 10.1007/s00217-005-0249-x
• Sterol fractions in hazelnut and virgin olive oils and 4,4′-dimethylsterols as possible markers for detection of adulteration of virgin olive oilPublication Name: Journal of the American Oil Chemists’ SocietyPublication Date: 2005-10DOI: 10.1007/s11746-005-1133-y
• Ultrasonically assisted solid-phase extraction and GC analysis of filbertone in hazelnut oilPublication Name: Journal of the American Oil Chemists’ SocietyPublication Date: 2003-04DOI: 10.1007/s11746-003-0694-0
• Enantiomeric composition of filbertone in hazelnuts and hazelnut oils from different geographical originsPublication Name: Journal of the American Oil Chemists’ SocietyPublication Date: 2002-06DOI: 10.1007/s11746-002-0527-1
• 4.2 Unsaturated Ketones of General FormulaPublication Name: Densities of Phenols, Aldehydes, Ketones, Carboxylic Acids, Amines, Nitriles, and NitrohydrocarbonsPublication Date: 2002DOI: 10.1007/10757146_11
• Off-line coupling of high-performance liquid chromatography and 1 H nuclear magnetic resonance for the identification of filbertone in hazelnut oilPublication Name: Journal of the American Oil Chemists’ SocietyPublication Date: 2001-12DOI: 10.1007/s11745-001-0423-8
• Detection of pressed hazelnut oil in admixtures with virgin olive oil by analysis of polar componentsPublication Name: Journal of the American Oil Chemists’ SocietyPublication Date: 2001-06DOI: 10.1007/s11746-001-0315-y
• AromastoffePublication Name: Springer-LehrbuchPublication Date: 2001DOI: 10.1007/978-3-662-08302-4_6
• Analysis of volatile compounds in edible oils using simultaneous distillation-solvent extraction and direct coupling of liquid chromatography with gas chromatographyPublication Name: European Food Research and TechnologyPublication Date: 2000-06-05DOI: 10.1007/s002170050587
• A contribution to the study of the enantiomeric composition of a chiral constituent in hazelnut oil used in the detection of adulterated olive oilPublication Name: European Food Research and TechnologyPublication Date: 1999-12-02DOI: 10.1007/s002170050550
• Study of the enantiomeric composition of chiral constituents in edible oils by simultaneous distillation-extraction. Detection of adulterated olive oilsPublication Name: Journal of the American Oil Chemists’ SocietyPublication Date: 1999-09DOI: 10.1007/s11746-999-0200-6
• Development of a Stable Isotope Dilution Assay for the Quantification of 5-Methyl-(E)-2-hepten-4-one: Application to Hazelnut Oils and HazelnutsPublication Name: Journal of Agricultural and Food ChemistryPublication Date: 1999-04-28PMID: 10552493DOI: 10.1021/jf9810214
• Characterization of Key Odorants in ChocolatePublication Name: Flavor ChemistryPublication Date: 1999DOI: 10.1007/978-1-4615-4693-1_13
• Chirospecific analysis in flavor and essential oil chemistry Part A. Filbertone ? the character impact compound of hazel-nutsPublication Name: Zeitschrift f�r Lebensmittel-Untersuchung und -ForschungPublication Date: 1991-02DOI: 10.1007/bf01202621
• Enantiomer Separation on Dissolved Cyclodextrin Derivatives by High-Resolution Gas Chromatography: Thermodynamic Data of Chiral RecognitionPublication Name: Recent Advances in Chiral SeparationsPublication Date: 1991DOI: 10.1007/978-1-4684-8282-9_17
• Analysis of the chiral aroma compound filbertone by inclusion gas chromatograph Publication Name: Zeitschrift f�r Lebensmittel-Untersuchung und -Forschung Publication Date: 1990-07 DOI: 10.1007/bf01202361
• Burdack-Freitag A, Schieberle P. Changes in the key odorants of Italian Hazelnuts ( Coryllus avellana L. Var. Tonda Romana) induced by roasting. J Agric Food Chem. 2010 May 26;58(10):6351-9. doi: 10.1021/jf100692k. PMID: 20426421.
• Rondanelli M, Nichetti M, Martin V, Barrile GC, Riva A, Petrangolini G, Gasparri C, Perna S, Giacosa A. Phytoextracts for Human Health from Raw and Roasted Hazelnuts and from Hazelnut Skin and Oil: A Narrative Review. Nutrients. 2023 May 23;15(11):2421. doi: 10.3390/nu15112421. PMID: 37299385; PMCID: PMC10255299.
• Taş NG, Yılmaz C, Gökmen V. Investigation of serotonin, free and protein-bound tryptophan in Turkish hazelnut varieties and effect of roasting on serotonin content. Food Res Int. 2019 Jun;120:865-871. doi: 10.1016/j.foodres.2018.11.051. Epub 2018 Nov 27. PMID: 31000307.
• Binello A, Giorgis M, Cena C, Cravotto G, Rotolo L, Oliveri P, Malegori C, Cavallero MC, Buso S, Casale M. Chemical modifications of Tonda Gentile Trilobata hazelnut and derived processing products under different infrared and hot-air roasting conditions: a combined analytical study. J Sci Food Agric. 2018 Sep;98(12):4561-4569. doi: 10.1002/jsfa.8984. Epub 2018 Apr 15. PMID: 29505171.
• Squara S, Stilo F, Cialiè Rosso M, Liberto E, Spigolon N, Genova G, Castello G, Bicchi C, Cordero C. Corylus avellana L. Aroma Blueprint: Potent Odorants Signatures in the Volatilome of High Quality Hazelnuts. Front Plant Sci. 2022 Mar 3;13:840028. doi: 10.3389/fpls.2022.840028. PMID: 35310662; PMCID: PMC8929135.
• Salvatore MM, Andolfi A, Nicoletti R. Mycotoxin Contamination in Hazelnut: Current Status, Analytical Strategies, and Future Prospects. Toxins (Basel). 2023 Jan 19;15(2):99. doi: 10.3390/toxins15020099. PMID: 36828414; PMCID: PMC9965003.
• Kabak B. Aflatoxins in hazelnuts and dried figs: Occurrence and exposure assessment. Food Chem. 2016 Nov 15;211:8-16. doi: 10.1016/j.foodchem.2016.04.141. Epub 2016 May 6. PMID: 27283601.
• Ozay G, Seyhan F, Pembeci C, Saklar S, Yilmaz A. Factors influencing fungal and aflatoxin levels in Turkish hazelnuts (Corylus avellana L.) during growth, harvest, drying and storage: a 3-year study. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2008 Feb;25(2):209-18. doi: 10.1080/02652030701711016. PMID: 18286411.
• Valente S, Meloni GR, Prencipe S, Spigolon N, Somenzi M, Fontana M, Gullino ML, Spadaro D. Effect of Drying Temperatures and Exposure Times on Aspergillus flavus Growth and Aflatoxin Production on Artificially Inoculated Hazelnuts. J Food Prot. 2020 Jul 1;83(7):1241-1247. doi: 10.4315/JFP-20-061. PMID: 32221534.

See also

• 2-Octanone
  • 2-Octanone is an organic compound with the formula CH₃C(O)C₆H₁₃. It is a colorless volatile liquid that is produced commercially for use in the fragrance industry. It is produced by the condensation of acetone and pentanal followed by hydrogenation of the alkene. It can also be produced by selective oxidation of 1-octene. It is one of three octanones, the others being 3-octanone and 4-octanone. It is a common if trace component of many cooked foods.
    •  ^{“2-Octanone”. pubchem.ncbi.nlm.nih.gov.}
    • ^{Siegel, Hardo; Eggersdorfer, Manfred (2000). “Ketones”. Ullmann’s Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a15_077. ISBN 9783527306732.}
    • ^{Elmore, J. Stephen; Mottram, Donald S.; Enser, Michael; Wood, Jeffrey D. (1999). “Effect of the Polyunsaturated Fatty Acid Composition of Beef Muscle on the Profile of Aroma Volatiles”. Journal of Agricultural and Food Chemistry. 47 (4): 1619–1625. doi:10.1021/JF980718M. PMID 10564028.}
• 3-Octanone
  • 3-Octanone is an organic compound with the formula C₅H₁₁C(O)C₂H₅. A colorless fragrant liquid, it is classified as a ketone. It is one of three octanones, the others being 2-octanone and 4-octanone.
    • ^{“3-Octanone”. Sigma-Aldrich.}
    • ^{NIOSH Pocket Guide to Chemical Hazards. “#0418”. National Institute for Occupational Safety and Health (NIOSH).}
  • Occurrence 3-Octanone is found in a variety of sources such as plants (such as lavender), herbs (such as rosemary, basil, and thyme), and nectarines. It was also found to be present in Japanese catnip (Schizonepeta tenuifolia) and the pine king bolete (Boletus pinophilus). It is produced by oyster mushrooms as an insecticide to kill roundworms.
    • ^{Opdyke, D.L.J., ed. (1979). Monographs on Fragrance Raw Materials. New York: Pergamon Press. p. 346.}
    • ^{Koedam, A.; et al. (1978). “Freshly Distilled Oil of the Leaves of Rasmarinus Officianalis L Contained 3-Octanone”. Z. Naturforsch. C. 33C (1–2): 144. doi:10.1515/znc-1978-1-226. S2CID 87276514.}
    • ^{Lee, Seung-Joo; Umano, Katumi; Shibamoto, Takayuki; Lee, Kwang-Geun (2005). “Identification of volatile components in basil (Ocimum basilicum L.) and thyme leaves (Thymus vulgaris L.) and their antioxidant properties”. Food Chemistry. 91: 131–137. doi:10.1016/j.foodchem.2004.05.056.}
    • ^{Takeoka GR; et al. (1988). “Nectarine volatiles: vacuum steam distillation versus headspace sampling”. J Agric Food Chem. 36 (3): 553–560. doi:10.1021/jf00081a037.}
    • ^{Yu, S; Chen, Y; Zhang, L; Shan, M; Tang, Y; Ding, A (2011). “Quantitative Comparative Analysis of the Bio-Active and Toxic Constituents of Leaves and Spikes of Schizonepeta tenuifolia at Different Harvesting Times”. International Journal of Molecular Sciences. 12 (10): 6635–44. doi:10.3390/ijms12106635. PMC 3210999. PMID 22072908.}
    • ^{Bozok, Fuat; Zarifikhosroshahi, Mozhgan; Kafkas, Ebru; Taşkin, Hatira; Buyukalaca, Saadet (2015). “Comparison of Volatile Compounds of Fresh Boletus edulis and B. Pinophilus in Marmara Region of Turkey”. Notulae Botanicae Horti Agrobotanici Cluj-Napoca. 43: 192–195. doi:10.15835/nbha4319731.}
    • ^{Li, Huiping; Liu, Junjie; Hou, Ziqiang; Luo, Xin; Lin, Jinsheng; Jiang, Ning; Hou, Lijuan; Ma, Lin; Li, Cuixin; Qu, Shaoxuan (2022). “Activation of mycelial defense mechanisms in the oyster mushroom Pleurotus ostreatus induced by Tyrophagus putrescentiae”. Food Research International. 160: 111708. doi:10.1016/j.foodres.2022.111708. PMID 36076457. S2CID 250931270.}
    • ^{Li, Huiping; Liu, Junjie; Hou, Ziqiang; Luo, Xin; Lin, Jinsheng; Jiang, Ning; Hou, Lijuan; Ma, Lin; Li, Cuixin; Qu, Shaoxuan (2022). “Activation of mycelial defense mechanisms in the oyster mushroom Pleurotus ostreatus induced by Tyrophagus putrescentiae”. Food Research International. 160: 111708. doi:10.1016/j.foodres.2022.111708. PMID 36076457. S2CID 250931270.}
    • ^{Ouellette, Jennifer (18 January 2023). “Carnivorous oyster mushrooms can kill roundworms with “nerve gas in a lollipop””. Ars Technica. Retrieved 26 January 2023.}
  • Uses 3-Octanone is used as a flavor and fragrance ingredient.
    •  ^{“3-octanone”. thegoodscentscompany.com.}
    • ^{Ashford RD (1994). Ashford’s Dictionary of Industrial Chemicals. London, England: Wavelength Publications Ltd. p. 389.}
    • ^{Code of Federal Regulations Title 21}

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.

External links

• Filbertone, Molecule of the Month, University of Bristol

Categories: 

• Enones
• Flavors
• Perfume ingredients