Structural Formula Vector Image
Title: l-Menthone
CAS Registry Number: 14073-97-3
CAS Name: (2S-trans)-5-Methyl-2-(1-methylethyl)cyclohexanone
Additional Names: (1R,4S)-(-)-p-menthan-3-one; 1-methyl-4-isopropylcyclohexan-3-one
Molecular Formula: C10H18O
Molecular Weight: 154.25
Percent Composition: C 77.87%, H 11.76%, O 10.37%
Literature References: Of the four optically active isomers of methone, the one occurring most frequently in nature. Found in various volatile oils, such as pennyroyal, peppermint, geranium: Simonsen, The Terpenes vol. I (University Press, Cambridge, 2nd ed., 1947) pp 314-327. Prepd by chromic acid oxidation of l-menthol: Hussey, Baker, J. Org. Chem. 25, 1434 (1960); Brown, Garg, J. Am. Chem. Soc. 83, 2952 (1961).
Properties: Bitter liq; slight peppermint odor. bp 207°. bp41 116-119°. mp -6°. d420 0.895. nD20 1.4505; nD23 1.4490. [a]D20 -24.8°; [a]D27 -28.9°. Slightly sol in water; sol in organic solvents.
Melting point: mp -6°
Boiling point: bp 207°; bp41 116-119°
Optical Rotation: [a]D20 -24.8°; [a]D27 -28.9°
Index of refraction: nD20 1.4505; nD23 1.4490
Density: d420 0.895
Derivative Type: Apinol
Literature References: Obtained by dry distln of wood of Pinus palustris Mill. (P. australis Michx.), Pinaceae is chiefly l-menthone: J. Pharm. Chim. 18, 139, 177, 208 (1918), C.A. 13, 569 (1919).
Properties: Amber-colored oil, bp ~182.2°, d 0.946.
Boiling point: bp ~182.2°
Density: d 0.946
Use: In perfume and flavor compositions.

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