Menthone



Menthone
IUPAC name (2S,5R)-2-Isopropyl-5-methylcyclohexanone
Other names l-Menthone
Identifiers
CAS number 14073-97-3
SMILES C1(=O)[C@H](C(C)C)CC[C@@H](C)C1
Properties
Molecular formula C10H18O
Molar mass 154.25 g/mol
Density 0.895 g/cm³
Melting point

-6 °C

Boiling point

207 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Menthone is a naturally occurring menthol which has a secondary alcohol in place of the carbonyl.

Menthone is a constituent of the essential oils of menthol in 1881 before it was found in essential oils in 1891. It is used in perfumery and cosmetics for its characteristic aromatic and minty odor.

This molecule is at the heart of one of the great mechanistic discoveries in organic chemistry. Ernst Beckmann in 1889 discovered that dissolving menthone in concentrated tautomer in which the asymmetric carbon atom was of trigonal (planar) rather than of tetrahedral geometry. This was an early example of the inference of an (almost) undetectable intermediate in a reaction mechanism accounting for the outcome of the reaction.

Preparation

Menthone may be prepared by dichromate.[1]

References

The references in this article would be clearer with a different or consistent style of citation, footnoting, or external linking.
  1. Merck Index, 12th Edition, 5883.
  2. E. Beckmann (1889). "Untersuchungen in der Campherreihe". Annalen 250: 322. doi:10.1002/jlac.18892500306.
  3. John Read (1930). "Recent Progress in the Menthone Chemistry.". Chemical Reviews 7 (1): 1-50. doi:10.1021/cr60025a001.
  4. M. Moriya (1881). "Contributions from the Laboratory of the University of Tôkiô, Japan. No. IV. On menthol or peppermint camphor". Journal of the Chemical Society, Transactions 39: 77-83. doi:10.1039/CT8813900077.
  5. For a molecular modelling experiment involving menthone, see here.
  1. ^ L. T. Sandborn. "l-Menthone". Org. Synth.; Coll. Vol. 1: 340. 
 
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