(-)-(E,R)-Filbertone - hazelnut, soft, butter, chocolate, metallic, weaker impact (at 25 ppb in water) Odor Threshold of (-)-(E,R)-Filbertone is about 10 times higher than for (+)-(E,S)-Filbertone Also known as (-)-(E,R)- Hazeltone or (-)-(E,R)-5-methyl-2-hepten-4-one Ref: Guntert, M.; Emberger, R.; Hopp, R.; Kopsel, M.; Silberzahn, W.; Werkhoff, P., Chiral analysis in flavor and essential oil chemistry. Part A, Filbertone, the character impact compound of hazelnuts, Flavour Science and Technology, Y. Bessiere & A. F. Thomas, Editors, John Wiley & Sons, Pub., Chichester, UK, pp. 29-32 (1990); Guntert, M.; Emberger, R.; Hopp, R.; Kopsel, M.; Silberzahn, W.; Werkhoff, P. Chirospecific analysis in flavour and essential oil chemistry. Part A, Filbertones, the character impact compound of hazelnuts. Z. Lebensm. Unters. Forsch., 192, 108-110 (1991); Schurig, V., Jauch, J., Schmalzing, D., Jung, M., Bretschneider, W., . Hopp, R, Werkhoff, P., "Analysis of the Chiral Aroma Compound Filbertone by Inclusion Gas Chromatography", Z. Lebensm. Unters. Forsch., 191, 28 (1990), Jauch, J., Schmalzing, D., Schurig, V., Emberger, R., Hopp, R., Köpsel, M., Silberzahn, W., Werkhoff, P., "Isolierung, Synthese und absolute Konfiguration von Filberton, dem aktiven Prinzip des Haselnußaromas (Isolation, Synthesis, and Absolute Configuration of Filbertone, the Principal Flavor Component of the Hazelnut), Angew. Chem., 101 (8), 1039-1041 (1989); Angew. Chem. Int. Ed. Engl., 28, 1022-1023 (1989); Emberger; Roland; Kopsel, Manfred; Bruning, Jurgen; Hopp, Rudolf; Sand, Theodor; Flavoring with 5-methyl-hept-2-en-4-one, United States Patent 4,563,365, January 7, 1986; Emberger; Roland; Kopsel, Manfred; Bruning, Jurgen; Hopp, Rudolf; Sand, Theodor;, Use of 5-methyl-hept-2-en-4-one as a fragrance and/or flavor, United States Patent 4,654,168, March 31, 1987

(+)-(E,S)-Filbertone - hazelnut, metallic, fatty, pyidine, stronger impact (at 25 ppb in water) Odor Threshold of (+)-(E,S)-Filbertone is about 10 times lower than for (-)-(E,R)-Filbertone Also known as (+)-(E,S)-Hazeltone or (+)-(E,S)-5-methyl-2-hepten-4-one The enantiomeric composition of raw hazelnuts falls in the ratio of 80-85% (+)-(E,S) and 15-20%(-)-(E,R) whereas for roasted hazelnuts the ratio is about 71.5-72.5% (+)-(E,S) and 27.5-28.5% (-)-(E,R). The flavor perception threshold (in 3% sucrose solution) = 0.000005 ppm for the racemic mixture and the recognition threshold is about 0.00003 ppm. At the perception threshold, (racemic) 5-methyl-hept-2-en-4-one produces a taste which can be described as "soft, buttery, full sensation in the mouth" while at and above the recognition threshold the description of the taste is "nutty, hazelnut, soft, buttery, full sensation in the mouth". In addition to its specific characterization in the hazelnut direction in appropriate flavoring compositions, it has, in all non-nut types of compositions, a particularly rounding effect, and provides more naturalness through its buttery soft basic fullness. (United States Patent 4,654,168, March 31, 1987) Ref: Guntert, M.; Emberger, R.; Hopp, R.; Kopsel, M.; Silberzahn, W.; Werkhoff, P., Chiral analysis in flavor and essential oil chemistry. Part A, Filbertone, the character impact compound of hazelnuts, Flavour Science and Technology, Y. Bessiere & A. F. Thomas, Editors, John Wiley & Sons, Pub., Chichester, UK, pp. 29-32 (1990); Guntert, M.; Emberger, R.; Hopp, R.; Kopsel, M.; Silberzahn, W.; Werkhoff, P. Chirospecific analysis in flavour and essential oil chemistry. Part A, Filbertones, the character impact compound of hazelnuts. Z. Lebensm. Unters. Forsch., 192, 108-110 (1991); Schurig, V., Jauch, J., Schmalzing, D., Jung, M., Bretschneider, W., . Hopp, R, Werkhoff, P., "Analysis of the Chiral Aroma Compound Filbertone by Inclusion Gas Chromatography", Z. Lebensm. Unters. Forsch., 191, 28 (1990), Jauch, J., Schmalzing, D., Schurig, V., Emberger, R., Hopp, R., Köpsel, M., Silberzahn, W., Werkhoff, P., "Isolierung, Synthese und absolute Konfiguration von Filberton, dem aktiven Prinzip des Haselnußaromas (Isolation, Synthesis, and Absolute Configuration of Filbertone, the Principal Flavor Component of the Hazelnut), Angew. Chem., 101 (8), 1039-1041 (1989); Angew. Chem. Int. Ed. Engl., 28, 1022-1023 (1989); Emberger; Roland; Kopsel, Manfred; Bruning, Jurgen; Hopp, Rudolf; Sand, Theodor; Flavoring with 5-methyl-hept-2-en-4-one, United States Patent 4,563,365, January 7, 1986; Emberger; Roland; Kopsel, Manfred; Bruning, Jurgen; Hopp, Rudolf; Sand, Theodor;, Use of 5-methyl-hept-2-en-4-one as a fragrance and/or flavor, United States Patent 4,654,168, March 31, 1987

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones

Sesquiterpenoid Related Odorants