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Menthone
Sign in to saveAlso known as 2-Isopropyl-5-methylcyclohexanone, trans-p-menthan-3-one
Menthone is a chemical compound of the monoterpene class of naturally occurring organic compounds found in a number of essential oils, one that presents with minty flavor. It is a specific pair of stereoisomers of the four possible such isomers for the chemical structure, 2-isopropyl-5-methylcyclohexanone. Of those, the stereoisoomer '''l-menthone'—formally, the (2S,5R)-trans'' isomer of that structure, as shown at right—is the most abundant in nature. Menthone is structurally related to menthol, which has a secondary alcohol (>C-OH) in place of the carbon-oxygen double bond (carbonyl group) p
Chemical data
- Formula
- C10H18O
- Molecular weight
- 154.25 g/mol
- IUPAC name
- 5-methyl-2-propan-2-ylcyclohexan-1-one
- SMILES
- CC1CCC(C(=O)C1)C(C)C
- InChIKey
- NFLGAXVYCFJBMK-UHFFFAOYSA-N
- XLogP
- 2.7
- Polar surface area
- 17.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 154.135765196
- Image
- (–)-menthone.svg
Show 3 more facts
- chemical formula
- C₁₀H₁₈O
- Commons category
- Menthone
- canonical SMILES
- CC1CCC(C(C)C)C(=O)C1
via Wikidata · CC0
~7 min read
Article
11 sectionsContents
- Occurrence
- Physical and sensory properties
- Structure and stereochemistry
- Interconversion
- Preparation
- Biochemical
- Chemical
- History
- See also
- Further reading
- References
Menthone is a chemical compound of the monoterpene class of naturally occurring organic compounds found in a number of essential oils, one that presents with minty flavor. It is a specific pair of stereoisomers of the four possible such isomers for the chemical structure, 2-isopropyl-5-methylcyclohexanone. Of those, the stereoisoomer '''l-menthone'—formally, the (2S,5R)-trans isomer of that structure, as shown at right—is the most abundant in nature. Menthone is structurally related to menthol, which has a secondary alcohol (>C-OH) in place of the carbon-oxygen double bond (carbonyl group) projecting from the cyclohexane ring.
Menthone is obtained for commercial use after purifying essential oils pressed from Mentha species (peppermint and corn mint). It is used as a flavorant and in perfumes and cosmetics for its characteristic aromatic and minty aroma.