5838. l-Menthone
Nomenclature
CAS number: 14073-97-3
(2S-trans)-5-Methyl-2-(1-methylethyl)cyclohexanone; (1R,4S)-()-p-menthan-3-one; 1-methyl-4-isopropylcyclohexan-3-one. C10H18O; mol wt 154.25.
C 77.87%, H 11.76%, O 10.37%.
Description and 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. [α]D20 24.8°; [α]D27 28.9°. Slightly sol in water; sol in organic solvents.Derivative
Apinol.Description and 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).