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Fenchone

From Wikipedia, the free encyclopedia

Fenchone[1]
Names
IUPAC name
1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one
Other names
1,3,3-Trimethyl-2-norcamphanone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.013.458 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3 checkY
    Key: LHXDLQBQYFFVNW-UHFFFAOYSA-N checkY
  • InChI=1/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3
    Key: LHXDLQBQYFFVNW-UHFFFAOYAX
  • O=C1C(C)(C)C2CC1(C)CC2
Properties
C10H16O
Molar mass 152.23 g/mol
Density 0.948 g/cm3
Melting point 6.1 °C (43.0 °F; 279.2 K)
Boiling point 193.5 °C (380.3 °F; 466.6 K)
1.4625
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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.[2]

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.[3]

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Transcription

References

  1. ^ Merck Index, 11th Edition, 3911.
  2. ^ 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.
  3. ^ 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.


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This page was last edited on 27 October 2022, at 19:32
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