:Fenchone

{{chembox

| Verifiedfields = changed

| verifiedrevid = 444691976

| Name = Fenchone

| Reference =Merck Index, 11th Edition, 3911.

| ImageFile = Fenchone.png

| ImageSize = 150px

| ImageName =

| IUPACName = 1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one

| OtherNames = 1,3,3-Trimethyl-2-norcamphanone

| Section1 = {{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 13869

| PubChem = 14525

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C11387

| InChI = 1/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3

| InChIKey = LHXDLQBQYFFVNW-UHFFFAOYAX

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = LHXDLQBQYFFVNW-UHFFFAOYSA-N

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

| CASNo = 1195-79-5

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

| CASNo2 = 4695-62-9

| CASNo2_Comment = D

| CASNo3_Ref = {{cascite|correct|CAS}}

| CASNo3 = 7787-20-4

| CASNo3_Comment = L

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

| UNII = 4Q6W8568TG

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

| UNII2 = S436YKU51N

| UNII2_Comment = D

| UNII3_Ref = {{fdacite|correct|FDA}}

| UNII3 = K6G5Y2Y3Q2

| UNII3_Comment = L

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 4999

| ChEBI2 = 165

| ChEBI2_Comment = D

| ChEBI3 = 36612

| ChEBI3_Comment = L

| SMILES = O=C1C(C)(C)C2CC1(C)CC2

}}

| Section2 = {{Chembox Properties

| Formula = C₁₀H₁₆O

| MolarMass = 152.23 g/mol

| Density = 0.948 g/cm³

| MeltingPtC = 6.1

| BoilingPtC = 193.5

| RefractIndex = 1.4625

}}

}}

Fenchone is an organic compound classified as a monoterpenoid and a ketone. It is a colorless oily liquid. It has a structure and an odor similar to those of camphor. Fenchone is a constituent of absinthe and the essential oil of fennel. Fenchone is used as a flavor in foods and in perfumery.Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg "Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim: 2002. Published online: 15 January 2003; {{doi|10.1002/14356007.a11_141}}.

Other names for fenchone include dl-fenchone and (±)-fenchone. It is a mixture of the enantiomers d-fenchone and l-fenchone. Other names for d-fenchone include (+)-fenchone and (1S,4R)-fenchone. Other names for l-fenchone include (−)-fenchone and (1R,4S)-fenchone. The d-fenchone enantiomer occurs in pure form in wild, bitter and sweet fennel plants and seeds, whereas the l-fenchone enantiomer occurs in pure form in wormwood, tansy, and cedarleaf.U. Ravid, E. Putievsky, I. Katzir, R. Ikan “Chiral gc analysis of enantiomerically pure fenchone in essential oils” in Flavour and Fragrance Journal, 7: 169-172, John Wiley & Sons: 1992. Published online: June 1992; {{doi|10.1002/ffj.2730070314}}.