Mentha piperita from peppermint

Fig. 97. Use of TLC in following the biosynthesis of terpenes in Mentha piperita [43]. Peppermint plants were grown in an atmosphere of COg and radioactive pulegone isolated from the essential oil of these plants, using preparative TLC. This compound was incubated with sections of young leaves from peppermint plant shoots. The autoradiograph of a chromatogram demonstrates formation of menthone (b) and menthofuran (a) from pulegone (c) in this leaf tiussue...

Inoue F, Sugima H, Tabuchi A, Kawasawa DE, Minami M (2003) Plant regoieration of peppermint, Mentha piperita from the hairy roots generated from microsegment infected with Agrobacterium rhizogenes. Plant Biotechnol 20 169-172... 

Peppermint oil is the volatile oil extracted from the fresh leaves of the flowering plant of Mentha piperita via steam distillation. Peppermint oil contains not less than 44% menthol. American peppermint oil contains from 50 to 78% of free /-menthol (Fig. 13.12.1) and from 5 to 20% combined in various es-... 

Natural peppermint contains several components that, if ingested, lead to a cold sensation in the mouth. The best known and best understood is (-)-menthol (IV), which is the dominant component of the peppermint oil extracted from Mentha piperita and M. arvensia. 

Menthol is the isomer that occurs most widely in nature. It is the main component of peppermint and cornmint oils obtained from the Mentha piperita and Mentha arvensis species. Esterified menthol also occurs in these oils (e.g., as the acetate and iso valerate). Other menthol stereoisomers may be present in these oils as well. 

Peppermint (Mentha piperita L.) honey is produced from the nectar of the aromatic flowers of an essential-oil plant, which is widely cultivated in the Soviet Union. Phacelia (Phacelia tanacetifolia Benth.) honey is light green or white and has a delicate aroma and tine, pleasant flavor. 

Therea renumerous species of mint including peppermint, Mcnf/zapipenta, spearmint, Mentha spicata, and cornmint, Mentha arvensis. Mentha piperita is actually a hybrid species bred from spearmint Mentha spicata and watermint Mentha aquatica. They all contain subspecies and chemotypes. Mints have a long tradition of culinary, fragrance, cosmetic and therapeutic applications. 

Crock, J., Wildung, M. and Croteau, R. (1997) Isolation and bacterial expression of a sesquiterpene synthase cDNA clone from peppermint (Mentha x piperita, L.) that produces the aphid alarm pheromone (E)-beta-famesene. Proc. Natl. Acad. Sci. USA, 94, 12833-8. 

PROP From steam distillation of Mentha piperita (Fam. Ljibiatae). Colorless to pale yellow liquid strong odor and taste of peppermint. D 0.896-0.908 25°/25°, reft index 1.459 20°. 

Menthanes, which include menthol, menthonc, terpineol, and carvone, are some of the best known monoterpene-based chiral synthons in organic synthesis. They are all relatively inexpensive and are commercially available in bulk quantities. Menthols and their corresponding ketones, menthones. were first isolated from peppermint oils of various species of Mentha piperita L [30]. Menthones can exist in two diastereomeric forms, each with two enantiomers. The ones with the methyl and isopropyl groups in a Zrans-orientation are termed menthones, whereas those with the two in a cz.s-orientation are isomenthones. /-Menthone (22), also denoted as (7A,4S)-(-)-menthone. is the most abundant stereoisomer and is obtained by the dry distillation of the wood of Finns palustris Me II [31]. It can also be produced chemically by chromic acid oxidation of /-menthol (23) [32]. /-Menthone is commercially available in bulk quantities with optical purities of 90-98% ee [33]. 

Figure 1. Scanning electron micrographs of untreated (A), Soxhlet-extracted (B), and MAP-treated (C) fresh peppermint leaves (Mentha piperita L. Mitchum). The Soxhlet was carried out for 6 hours whereas the MAP treatment consisted of a single irradiation of 20 seconds. Hexane was used as solvent in both cases. Note the loss of structural characteristics of the surface of the Soxhlet-extracted specimen. The secretory gland is much reduced in size with the appearance of a deflated balloon as a result of the permeation and diffusion processes through its walls. Cavities created by the localised explosion of secretory glands characterise the MAP-treated sample (figure adapted from reference [6]).

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. 

Peppermint oil is extracted from the leaves of the peppermint plant, Mentha piperita, by steam distillation, by which various oils in the plant are separated from each other. 

CioHhOj, Mr 166.22, oil, [alg -51.8° (C2H5OH). A constituent and aroma component of peppermint oils from Mentha piperita. 

Menthan-3-ol forms four pairs of enantiomers. The levorotatory (1J ,3R,45)-enantiomer referred to as (-)-menthol represents the most significant. It is the major component of peppermint oil obtained from the fresh-flowering plant Mentha piperita (Labiatae), and is widely used for flavoring and as fragrance in confectionery and perfumery. 

About 50 elemanes known to date comprise p-elemenone from the oil of myrrh, representing the Cope rearrangement product of germacrone, (-)-bicycloelemene from peppermint oils of various provenance (e.g. Mentha piperita or Mentha ar-vensis), and p-elemol which is not only a minor component of Javanese oil of citro-nella but is also found in the elemi oil with an odor like pepper and lemon, expressed from the Manila elemi resin of the tree Canarum luzonicum (Burseraceae). 

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)... 

Enzymes in cell-free systems from carrot Daucus carota, Apiaceae) and peppermint Mentha piperita Lamiaceae) catalyze the reversible formation of nerol and neryl phosphate from geraniol and geranyl phosphate, respectively. Geranyl phosphate appears to have been isomerized directly to the neryl derivative without the intervention of an aldehyde intermediate. The presence of a flavin, thiol, and light was required for the reaction (Croteau, 1984). 

Preparations from Mentha piperita (peppermint, La-miaceae) convert the acyclic precursors geranyl and neryl pyrophosphate into limonene (11). The bulk of the cyclase activity is in the soluble-enzyme fraction (Croteau, 1984). 

The enzymes responsible for the hydroxylation of monoterpenes such as (— )-limonene (11) from peppermint Mentha piperita), spearmint Mentha spicata), and perilla Per-ilia frutescens) have been isolated and characterized (Karp et al., 1987,1990). Microsomal preparations from the epidermal oil glands of these plants catalyze the NADPH and 02-dependent allylic hydroxylation of (- )-(45)-limonene (the major olefinic constituent of each of the three species) at C-3, C-6, and C-7, respectively, to produce (- )-rra j-isopiper-itenol (34), (- )- m 5-carveol (35), and (- )-perillyl alcohol (36) (Fig. 19.9) (Karp et al., 1990). These transformations are the key steps in the biosynthesis of oxygenated monoterpenes in the respective species. The enzymes appear to be... 

Karp, F., C. A. Mihauak, J. L. Harris, and R. Croteau, Monoter-pene biosynthesis Specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves. Arch. Biochem. Biophys., 276, 219-226 (1990). 

Peppermint oil is derived from the dried leaves and flowering tops of Mentha piperita (Lamiaceae). The oil consists of about 50% menthol. The taste and odour of peppermint oil are also influenced by some of its minor components, notably the menthol esters... 

Menthol is a major component of various mint oils. The plant oil, often referred to as peppermint oil (from Mentha piperita) or cornmint oil (from Mentha arvensis), is readily extracted from the plant by steam distillation (Wichtel, 2002). It has a pleasant typical minty odor and taste, and is widely... 

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