Menthol, menthone, menthyl acetate

Mentha arvensis L. M. haplocalyx Briq. China Menthol, menthone, menthyl acetate.33 Stimulate gastrointestinal tract motility and central nervous system, dilate peripheral blood vessels. Increase sweat gland secretion. 

N.A. Menthol, menthone, menthyl acetate, camphene, limonene, terpenoids." Treat colds, sore throats, sore mouth. 

Some twenty different constituents have been found in American peppermint oil, including menthol, menthone, menthyl acetate, cineol, amyl alcohol, pinene, 1-limonene, phellandrene, dimethyl sulx)hide, menthyl isovalerianate, isovalerianic aldehyde, acetaldehyde, acetic acid, and isovalerianic acid. 

There are considerable differences in the composition of the various mint oils, determined by species and environmental conditions during growth, harvesting, and postharvest handling. It is convenient to consider these oils in two groups (a) peppermint and (b) spearmint. Peppermint (M. piperita) and commint (M. arvensis) oils have much in common, the principle constituents of each being menthol, menthone, menthyl acetate, and other esters. It is the ratio of these components that determines their distinctive profiles. 

Mentha piperita (-)-Menthol, (-)-menthone, (-)-menthyl acetate, (+)-menthofuran, a-pinene, a-phellandrene. 

America, and Japan. The main constituents of the essential oil are a- and p-pinene, limonene, cineol, ethyl amylcarbinol, menthone, menthol, isomenthol, menthyl acetate, and piperitone. It has a strong mint odor with a sweet balsam taste masked by a strong cooling effect. It is widely used in foods, as well as in liquid pharmaceuticals, to 8000 ppm. 

The essential oils of the Mentha species are known to be valuable ingredients of pharmaceutical and cosmetic preparations. Menthone, isomenthone, menthol and menthyl acetate, the most important Mentha oil constituents, are defined by their amounts as substantial parameters of mentha oil quality. Even off-line HPTLC/enan-tio-GC coupling has proved to be a valuable method in authenticity control of mint and peppermint oils. After preseparating by HPTLC (silica gel dichloromethane) the menthyl acetate fraction is isolated and directly injected for stereodifferentiation with permethyl p-cyclodextrin. Racemic menthyl acetate was detected by Kreis et al. as a frequently used adulteration of Mentha oils [20]. 

Carbon dioxide Menthol Menthone glycerin acetal Menthyl lactate J-Menthyl lactate cooling agent, liniments Menthol... 

A cultivar of M. arvensis has been reported to contain high concentrations of menthofuran (42%) and lesser amounts of menthol (21%), menthyl acetate (14%), and menthone (0.71%). ... 

Fig. 2 Fluorescence scan of a chromatogram of peppermint oil menthol (1), cineole (2), menthone (3), menthyl acetate (4), menthofuran/terpenes (5).

Menthol from Dementholized Cornmint Oil. Dementholized cornmint oil, from which (-)-menthol has been removed by crystallization and which still contains 40-50% free menthol, can be reused for producing (-)-menthol. The fairly large quantity of (-)-menthone in the oil (30-50%) is hydrogenated to form a mixture of mainly (-)-menthol and (+)-neomenthol the (-)-menthyl esters present (chiefly (-)-menthyl acetate) are saponified. Additional (—)-menthol is then separated from other components by crystallization, distillation, or via the boric acid esters. 

Composition 30-55% (-)-menthol, 14-32% (-)-menthone, 1.5-10% (-i-)-iso menthone, 2.8-10% menthyl acetate, 3.5-14% 1,8-cineole, 1-9% menthofuran, up to 4% pule-gone [220], as well as 3-octanol, trans-sabinene hydrate, piperitone, viridrflorol, mono- and sesquiterpene hydrocarbons. For further constituents see [221, 222, 223[. On the differentiation between peppermint oils and the detection of dementholised commint oil as a major adulterant see the results of Lawrence et al. [224], The ratio of 1,8-cineole limonene (min. 2) was even implemented in the European Pharmacopoeia. The latter also limits the isopulegol content for Mentha piperita oil to 0.2%. 

The simultaneous optical resolution of menthone, isomenthone, menthol as well as menthyl acetate has already been achieved using a column combination of three different columns, coated with modified cyclodextrins. All four enantiomeric pairs of these compounds were directly stereoanalyzed. Appropriate dilutions of mint and peppermint oils were analyzed by a single chromatographic run and without any preseparation [93]. 

By means of enantio-MDGC analysis using the column combination SE 52 / DIME-P-CD in PS 268 the simultaneous stereodifferentiation of menthone (1,2) neomenthol (3, 4), isomenthone (5, 6) menthol (7, 8), neoisomenthol (9, 10) and menthyl acetate (11, 12) has been verified and applied to various peppermint oils (Fig. 6.35 Fig. 6.36). 

Lane 1 menthol, menthone lane 2 menthyl acetate, menthofuran lanes 3- 8 peppermint oils from different manufacturers... 

As in commint oil, the main component of peppermint oil is (-)-menthol (34— 46%) it also contains (-)-menthone (15-27%) and (-)-menthyl acetate (2.5-7 %). However, peppermint oil, unlike cornmint oil, has a higher content of (+)-menthofuran [17957-94-7] (0.5-6%). These data refer to oils of US type oils of other origins (China, India) may have slightly different compositions [628-6331]. 

Oil of Peppermint. Col perm in Mintec. Steam-distilled, volatile oil from fresh flowering plant Mentha piperita L, Labiatae. The Japanese oil, also known as oil of Poho, is the liq portion remaining after the separation of menthol from the oil of Mentha arvensts L., Labiatae. Constit Not less than 50% total menthol including 5 -9% esters ealed as menthyl acetate menthyl isovalerate, menthone, inactive pinene, /-limonene, cadinene, phellandrene, some acetaldehyde, isovaleric aldehyde, amyl alcohol, dimethyl sulfide. 

Definition Volatile oil from steam distillation of Mentha piperita, contg. menthol, and menthyl esters incl. menthyl acetate, and menthone Properties Colorless to pale yel. liq., strong penetrating peppermint odor, pungent taste producing sensation of cold when air is drawn into mouth sol. in 4 vols 90% alcohol very si. sol. in water dens. 0.896-0.908 ref. index 1.460-1.471 (20 C)... 

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