Piperitone

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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.766
UNII
  • 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).
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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
  1. 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
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