:Filbertone

{{Chembox

| ImageFile = Filbertone.svg

| ImageSize = 200px

| IUPACName = (2E)-5-Methyl-2-hepten-4-one

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo = 102322-83-8

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo1 = 135910-94-0

| CASNo1_Ref = {{cascite|correct|CAS}}

| CASNo1_Comment = (R)

| CASNo2 = 122440-59-9

| CASNo2_Ref = {{cascite|correct|CAS}}

| CASNo2_Comment = (S)

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 8K2S58736F

| UNII1 = F91628PI7J

| UNII1_Ref = {{fdacite|correct|FDA}}

| UNII1_Comment = (R)

| UNII2 = Z91CSH86RZ

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2_Comment = (S)

| PubChem = 5362588

| ChemSpiderID = 4515100

| SMILES = O=C(/C=C/C)C(C)CC

| InChI = 1/C8H14O/c1-4-6-8(9)7(3)5-2/h4,6-7H,5H2,1-3H3/b6-4+

| InChIKey = ARJWAURHQDJJAC-GQCTYLIABX

| StdInChI = 1S/C8H14O/c1-4-6-8(9)7(3)5-2/h4,6-7H,5H2,1-3H3/b6-4+

| StdInChIKey = ARJWAURHQDJJAC-GQCTYLIASA-N

}}

|Section2={{Chembox Properties

| C=8 | H=14 | O=1

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

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|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

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}}

Filbertone is the principal flavor compound of hazelnuts.{{Cite journal | doi = 10.1002/anie.198910221 | title = Isolation, Synthesis, and Absolute Configuration of Filbertone - the Principal Flavor Component of the Hazelnut | year = 1989 | last1 = Jauch | first1 = Johann | last2 = Schmalzing | first2 = Dieter | last3 = Schurig | first3 = Volker | last4 = Emberger | first4 = Roland | last5 = Hopp | first5 = Rudolf | last6 = Köpsel | first6 = Manfred | last7 = Silberzahn | first7 = Wilhelm | last8 = Werkhoff | first8 = Peter | journal = Angewandte Chemie International Edition in English | volume = 28 | issue = 8 | pages = 1022}} It is used in perfumery and is designated as generally recognized as safe (GRAS) for use in food products.{{cite journal | doi = 10.1590/S0103-50531998000600011 | title = An Alternative Route for the Synthesis of (E)-(+)-5(S)-Methylhept-2-en-4-one (Filbertone) | year = 1998 | last1 = Zarbin | first1 = Paulo H.G. | last2 = Yonashiro | first2 = Massami | last3 = Perissini Jr | first3 = Waldir | journal = Journal of the Brazilian Chemical Society | volume = 9 | issue = 6 | pages = 583| doi-access = free }}

Because filbertone is found in hazelnut oil, its presence can be used to detect the adulteration of olive oil with less expensive hazelnut oil.{{Cite journal | doi = 10.1021/jf9807014 | title = Rapid Recognition of Olive Oil Adulterated with Hazelnut Oil by Direct Analysis of the Enantiomeric Composition of Filbertone | year = 1998 | last1 = Ruiz Del Castillo | first1 = María Luisa | last2 = Caja | first2 = María del Mar | last3 = Herraiz | first3 = Marta | last4 = Blanch | first4 = Gracia P. | journal = Journal of Agricultural and Food Chemistry | volume = 46 | issue = 12 | pages = 5128}}{{Cite journal | doi = 10.1016/j.foodchem.2005.06.008 | title = Study of the adulteration of olive oil with hazelnut oil by on-line coupled high performance liquid chromatographic and gas chromatographic analysis of filbertone | year = 2006 | last1 = Flores | first1 = Gema | last2 = Ruiz Del Castillo | first2 = Maria Luisa | last3 = Herraiz | first3 = Marta | last4 = Blanch | first4 = Gracia Patricia | journal = Food Chemistry | volume = 97 | issue = 4 | pages = 742}}

The natural compound is a mixture of both enantiomers, and its composition can vary depending on the source.{{cite journal | doi = 10.1007/s11746-002-0527-1 | title = Enantiomeric composition of filbertone in hazelnuts and hazelnut oils from different geographical origins | year = 2002 | last1 = Ruiz Del Castillo | first1 = M. L. | last2 = Gómez Caballero | first2 = E. | last3 = Blanch | first3 = G. P. | last4 = Herraiz | first4 = M. | journal = Journal of the American Oil Chemists' Society | volume = 79 | issue = 6 | pages = 589| s2cid = 94014818 | hdl = 10261/241822 | hdl-access = free }}{{Cite journal | doi = 10.1007/BF01202621 | title = Chirospecific analysis in flavor and essential oil chemistry Part A. Filbertone ? The character impact compound of hazel-nuts | year = 1991 | last1 = Güntert | first1 = Matthias | last2 = Emberger | first2 = Roland | last3 = Hopp | first3 = Rudolf | last4 = Köpsel | first4 = Manfred | last5 = Silberzahn | first5 = Wilhelm | last6 = Werkhoff | first6 = Peter | journal = Zeitschrift für Lebensmittel-Untersuchung und -Forschung | volume = 192 | issue = 2 | pages = 108| s2cid = 92237130 }}