5841. Menthyl Isovalerate

Nomenclature

CAS number: 28221-20-7; 89-47-4 (dl-Form) ; 16409-46-4 (unspecified stereo)
3-Methylbutanoic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester; isovaleric acid l-menthyl ester; l-menthyl valerate.
C15H28O2; mol wt 240.38.
C 74.95%, H 11.74%, O 13.31%.

Description and references

Naturally occurring component of peppermint oil. Isoln from American peppermint oil: F. B. Power, C. Kleber, Arch. Pharm. 232, 636 (1894). Prepn from l-menthol and valeryl chloride: H. Rupe, Ann. 369, 311 (1910). Biosynthesis in Mentha piperita L.: H. Rothbcher, Pharmazie 23, 389 (1968) PubMed. Prepn and NMR spectra: A. Ahmad et al., J. Essent. Oil Res. 12, 775 (2000).

Chemical structure

Properties

Colorless liquid; menthol and valerian odor; cooling, faintly bitter taste. bp 241°; bp9 129°. d25 0.910; d15 0.906-0.908. nD20 1.4485-1.4486. [α]D26 58.39°. Insol in water. Freely sol in alcohol, chloroform, ether, oils. Dec by alkalies.

Derivative

Mixture with menthol.

Nomenclature

Validol (Farmak).

Description and references

GLC analysis in tablets: G. B. Golubitskii et al., J. Anal. Chem. 63, 65 (2008).

Use

Pharmaceutic aid (flavor). Flavor in beverages, candies, baked goods.

Therapeutic Category

Mixture with menthol in treatment of angina.