Peppermint constituents

Flavor. Dentifrices are used to refresh the oral cavity. Flavor oils and other flavoring materials are key to that function (see Flavors and spices). Generally recognized as safe (GRAS) flavors or flavors from approved lists are used. The most popular flavors are peppermint [8006-90-4], spearmint [8008-79-5], cinnamon [8006-79-9], and mixtures of these. Menthol is a principal constituent of the mint flavors and a source of refreshment and coolness. 

Esters, or salts of alkyl radicles, such as linalyl acetate, etc., are frequently the most important constituents of essential oils. Their importance is especially noteworthy in such cases as lavender , bergamot, peppermint, and wintergreen oils, and their estimation is very frequently necessary. The principle upon which this depends is the fact that most esters are decomposed by solution of caustic alkali (preferably in alcohol) according to the equation—... 

Colorless crystals with a strong characteristic odor. It is the chief constituent of peppermint oil. 

Source Pyridine occurs naturally in potatoes, anabasis, henbane leaves, peppermint (0 to 1 ppb), tea leaves, and tobacco leaves (Duke, 1992). Identified as one of 140 volatile constituents in used soybean oils collected from a processing plant that fried various beef, chicken, and veal products (Takeoka et al., 1996). 

Many food constituents including peppermint, spearmint, and tea contain 4-phenylpyridine, another close relative.775 While administration of L-dopa to replace the deficit in the basal ganglia seemed the ideal treatment for Parkinson disease, mental deterioration is not stopped, and for some patients the drug loses its effectiveness in about three years. Based on the new information about MPTP, treatment with extra vitamin E as an antioxidant along with an MAO inhibitor is being tested as a way to prevent further damage from environmental toxins.776... 

Alcohols occur widely in nature. Methanol is also known as wood alcohol because it can be obtained by distilling wood in the absence of air. It is very poisonous and can cause blindness or death if ingested. Ethanol is consumed in alcoholic beverages. Other simple alcohols, such as 2-phenylethanol from roses and menthol from peppermint, are constituents of natural flavors and fragrances. Alcohols are important intermediates in chemical synthesis. They are also commonly used as solvents for various chemical processes. Ethylene glycol is used in antifreeze and in the preparation of polymers such as Dacron. 

Comparison with terpenoid constituents and peppermint oil. Phytother Res 8 305-307... 

Table VIII shows the dramatic differences between fresh and dried leaves. In this case, as oj sed to peppermint, rosemary and thyme, trans-2-hexenal is more in the fresh than in the dried and aged. The same is true for phenyl ethyl alcohol. Interestingly, trans-cinnamic aldehyde constitutes 50% of the total living headspace volatiles, but it is still less than in the aged leaf and commercial oil. However, cinnaniyl alcohol represents 20% of the fresh volatiles but is only a trace conpcanent of the aged leaf and oil. 4-Methoxy cinnamic aldehyde, identified as a cassia constituent for the first time, also increases 3-fold on drying but has disappeared completely in the comtnercial oil. 2-Methoxy cinnamic aldehyde, sometimes called the character impact component of cassia oil, is present in the headspace of the leaves to only a minor extent but it is the second most abundant component of the oil.

With the advent of hydrophobic cyclodextrin derivatives, many chiral constituents of essential oils became the subject of a detailed investigation of their enantiomeric composition. Several essential oils are used as additives in pharmaceutical formulations, for example, pine needle oil or peppermint oil. They are not only used for their pleasant flavor or fragrance, monoterpene hydrocarbons like a-pinene 18], p-pinene [9], and... 

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 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]. 

Peppermint oil menthol, the principal constituent of peppermint oil, has been shown to have a relaxant action on smooth muscle. The oil acts directly on the colon and is formulated as enteric-coated capsules to prevent dispersal higher up the gastrointestinal canal. It may nevertheless exacerbate heartburn symptoms. 

CgHg02, Mv 136.15, Pl01.3kPa 265.5 °C, 49- 1.0809, occurs in Japanese peppermint oil, in neroli oil, and in traces in rose oils. It is a volatile aroma constituent of many foods (e.g., honey). It forms colorless crystals (mp 78 °C) that have a honey odor. 

Menthane, C6Hlo(CH3)( so-C3H7)(l,4), is hexahydrocy-mene. The hydrocarbon is of interest as many important compounds which occur in nature are derived from it. Menthol, the principal constituent of the oil of peppermint, is a derivative of menthane which contains a hydroxyl group in combination with the carbon atom ortho to the isopropyl radical. 

Cineoly terpineol, and thujone are isomers of borneol which occur in certain essential oils. Mentholy mint-camphor, C10H20O, the chief constituent of the oil of peppermint, has been mentioned (455). 

Professor Rufus T. Firefly of Fredonia State University wanted to stump his ace chemistry student. Sea Water (C-H2O, alias formaldehyde). The professor asked Sea Water to deduce the structure of menthol, the principal flavoring constituent of peppermint, on the basis of the following data the molecular formula of menthol is C10H20O when heated in the presence of sulfuric acid, a dehydration reaction ensues to form compound A ozonolysis of compound A followed by a reductive workup yields 3,7-dimethyl-6-oxo-octanal menthol also reacts with nitric acid and vanadium oxide, when heated, to form 2-isopropyl-5-methyl-hexanedioic acid. 

Composition Genuine essential oils consist exclusively of volatile components with boiling points mainly between 150 and 300 °C. They contain predominantly hydrocarbons or monofunctional compounds such as aldehydes, alcohols, esters, ethers, and ketones. Parent compounds are mono- and sesquiterpenes, phenylpropane derivatives, and longer-chain aliphatic compounds. Accordingly, essential oils are relative non-polar mixtures, i.e., they are soluble in most organic solvents. Often the organoleptic properties are not determined by the main components but by minor and trace compounds such as, e.g., 1,3,5-undecatrienes and pyrazines in galbanum oil. In many of the commercially important oils, the number of identified components exceeds 100. Very many of the constituents are chiral, frequently one isomer predominates or is exclusively present, e. g., (- )-menthol in peppermint oils or (-)-linalyl acetate in lavender oil. 

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

IR-l-0cten-3-ol (Matsutake alcohol). CgH, 0, Mr 128.21, bp. 175 °C, [alg -20.2° LDjo (rat p.o.) 340 mg/kg. A typical mushrooms aroma constituent (olfactory threshold 1 ppb ) with an earthy-fungal odor impact compound in mushroom and Camem-bert flavor (see cheese flavor), but also occurring in many essential oils and flavors, e.g., in lavender, peppermint, rosemary, and thyme oil, as well as seafood flavors. Only the (/ )-enantiomer occurring in 90-97% enantiomeric excess possesses the pure fungus odor, the (S)-compound has a more vegetable-like odor. 

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