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
CAS Number	89-81-6 (D/L) 6091-50-5 (D) 4573-50-6 (L)
3D model (JSmol)	Interactive image
ChEBI	CHEBI:48933
ChemSpider	6721
ECHA InfoCard	100.001.766
PubChem CID	6987
UNII	1VZ8RG269R 8ZZ2GU5WBU (D) 8GZY0Q0N20 (L)
CompTox Dashboard (EPA)	DTXSID7052604
InChI InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3 Key: YSTPAHQEHQSRJD-UHFFFAOYSA-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
SMILES CC1=CC(=O)C(CC1)C(C)C
Properties
Chemical formula	C10H16O
Molar mass	152.23 g/mol
Density	0.9331 g/cm^3
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