DL-piperitone

Also known as p-Menth-1-en-3-one, 3-Carvomenthenone, 3-methyl-6-(1-methylethyl)-2-cyclohexen-1-one, 6-Isopropyl-3-methylcyclohex-2-enone, 6-Isopropyl-3-methyl-2-cyclohexen-1-one, 3-Methyl-6-(propan-2-yl)cyclohex-2-en-1-one, FEMA 2910

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. The L-form has been isolated from Sitka spruce.

Chemical data

Formula: C10H16O
Molecular weight: 152.23 g/mol
IUPAC name: 3-methyl-6-propan-2-ylcyclohex-2-en-1-one
SMILES: CC1=CC(=O)C(CC1)C(C)C
InChIKey: YSTPAHQEHQSRJD-UHFFFAOYSA-N
XLogP: 2.2
Polar surface area: 17.1 Å²
H-bond donors: 0
H-bond acceptors: 1
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Has part: carbon
Mass: 152.12

Show 5 more facts

canonical SMILES: CC1=CC(=O)C(CC1)C(C)C
chemical formula: C₁₀H₁₆O
boiling point: 233
partition coefficient water/octanol: 2.85
Commons category: Piperitone

Sources (2)

via Wikidata · CC0

~2 min read

Encyclopedic overview

5 sections

Contents

Occurrence
Properties
Production
Reactions
References

== Occurrence == left|thumb|Eucalyptus dives Piperitone is found in many essential oils, including over thirty species of the genus Eucalyptus. High levels are present in certain species of Eucalyptus and Mentha. In the genus Eucalyptus, the highest concentrations are found in Eucalyptus dives. Both enantiomers occur naturally. In Eucalyptus species, (-)-piperitone is present; in mint species, (+)-piperitone is found; and some plants contain racemate piperitone.

Excerpted from Wikipedia’s “DL-piperitone” article, available under the CC BY-SA 4.0 licence.