Piperitone

Summary

Piperitone is a natural monoterpene ketone which is a component of some essential oils. Both stereoisomers, the D-form and the L-form, are known. The D-form has a peppermint-like aroma and has been isolated from the oils of plants from the genera Cymbopogon, Andropogon, and Mentha.[1] The L-form has been isolated from Sitka spruce.[1]

Piperitone[1]
Names
IUPAC name
6-Isopropyl-3-methyl-1-cyclohex-2-enone
Other names
3-Carvomenthenone; p-Menth-1-en-3-one
Identifiers
  • 89-81-6 (D/L) checkY
  • 6091-50-5 (D) checkY
  • 4573-50-6 (L) checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:48933 ☒N
ChemSpider
  • 6721 ☒N
ECHA InfoCard 100.001.766 Edit this at Wikidata
  • 6987
UNII
  • 1VZ8RG269R checkY
  • 8ZZ2GU5WBU (D) checkY
  • 8GZY0Q0N20 (L) checkY
  • DTXSID7052604 Edit this at Wikidata
  • InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3 ☒N
    Key: YSTPAHQEHQSRJD-UHFFFAOYSA-N ☒N
  • InChI=1/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3
    Key: YSTPAHQEHQSRJD-UHFFFAOYAC
  • CC1=CC(=O)C(CC1)C(C)C
Properties
C10H16O
Molar mass 152.23 g/mol
Density 0.9331 g/cm3
Melting point 232 to 233 °C (450 to 451 °F; 505 to 506 K)
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 ?)
Infobox references

Piperitone is used as the principal raw material for the production of synthetic menthol and thymol. The primary source of D/L-piperitone is from Eucalyptus dives, produced mainly in South Africa.[2]

References edit

  1. ^ a b c Merck Index, 11th Edition, '7443
  2. ^ Boland, D.J., Brophy, J.J., and A.P.N. House, Eucalyptus Leaf Oils, 1991, ISBN 0-909605-69-6