Natural wintergreen oil

OIC ACID METHYL-o-HYDROXYBENZOATE METYLESTER KYSELINY SALICYLOVE (CZECH) NATURAL WINTERGREEN OIL OIL OF WINTER-GREEN SAUCYLIC ACID, METHYL ESTER SWEET BIRCH OIL SYNTHETIC WINTERGREEN OIL TEABERRYOIL WINTERGREEN OIL (FCC) WINTERGREEN OIL, SYNTHETIC... 

Results for other aromatic substances are compiled in Table 6.5, but are not discussed in detail, as the available data do not justify a discussion. Methyl salicylate, the main component of natural wintergreen oil is often used in cosmetic products. The quite negative 8 C-values of the natural product (5 C-values from -32.6 to -33.7%o) are probably partially caused by the extreme depletion of the methyl groups (see 6.2.2.4.4) and permit perhaps a discrimination from the nature-identical product (8 C-values from -27.7 to -30.8%o). The 5 H-values of natural methyl salicylate -130 to - 63%o [3, 270[ are, with the exception of one sample (-56%o), in the range of other natural aromatic substances (e.g. benzaldehyde, cinnamic aldehyde, anethole). Nature-identical analogues show more positive 5 H-values. 

Wintergreen Oil. Water distillation of the leaves of Gaultheriaprocumbens L. yields an oil which consists of essentially one chemical constituent, methyl saUcylate. Because of this, the oil has been almost totally replaced by the synthetic chemical. Natural oil of wintergreen [68917-75-9] is a pale yellow to pinkish colored mobile Hquid of intensely sweet-aromatic odor and flavor. The oil or its synthetic replacement find extensive use in pharmaceutical preparations, candy, toothpaste, industrial products, and in rootbeer flavor. In perfumery, it is used in fougnre or forest-type fragrances. 

Essential oils are concentrated extracts or steam distillates of aromatic plants. Oils such as wintergreen or jasmine have been added to enhance the flavor and smell of food for centuries and are key components of perfumes. Chemical analysis of these oils reveals that the overall smell is due to complex mixtures of small molecules, many of which contribute to the smell of the oil. Indole and indolic compounds are common components of these mixtures. Natural jasmine oil typically contains about 2.5% indole. Over time, the increasing cost of raw materials and processing has led to efforts to produce simpler nfixtures that would have the same sensory effect. Reasonable approximations of many of these oils can be made today with completely synthetic components. Despite these advances, the imporl/export market for natural essential oils in 2008 still was a respectable 2.5 billion (See PDF download from http //www.cmm.org/index.php optiOTi=com docman task). 

Wintergreen Oil.—There are two natural sources of this oil, the Gaultheria procunxhens and the Betula lenta. Both oils consist, almost entirely of methyl salicylate and are practically identical in properties, the chief difference being that the former has a slight leevo-rotation, while the latter is inactive. 

Essential oils are obtained from fmits and flowers (61,62). Volatile esters of short- and medium-chain carboxyHc acids or aromatic carboxyHc acids with short- and medium-chain alcohols are primary constituents of essential oils, eg, ethyl acetate in wines, brandy, and in fmits such as pineapple ben2yl acetate in jasmine and gardenia methyl saHcylate in oils of wintergreen and sweet birch. Most of these naturally occurring esters in essential oils have pleasant odors, and either they or their synthetic counterparts are used in the confectionery, beverage, perfume, cosmetic, and soap industries (see Oils, essential). 

Phenols occur widely throughout nature and also serve as intermediates in the industrial synthesis of products as diverse as adhesives and antiseptics. Phenol itself is a general disinfectant found in coal tar methyl salicylate is a flavoring agent found in oil of wintergreen and the urushiols are the allergenic constituents of poison oak and poison ivy. Note that the word phenol is the name both of the specific compound hydroxybenzene and of a class of compounds. 

Some natural products have an aroma, and taste, that derives largely from a single compound. For example, oil of wintergreen is about 99% methyl salicylate ... 

It is commonly asserted that the words aromatic compounds" were introduced at the end of the eighteenth century to distinguish such molecules from their aliphatic homologues because of their pleasant olfactory properties natural products such as oil of wintergreen, aniseed, sassafras, oil of cinnamon and vanilla beans were included at this time in the "aromatic class of compounds. 

Oil of Wintergreen. Methyl Salicylate.— The most interesting natural source of the acid, however, is oil of wintergreen obtained from the wintergreen plant, Gatdtheria procumbens. The chief constituent of this oil is the methyl ester of salicylic acid, methyl salicylate,... 

The phenol structure is widespread in nature as vitamin E, oil of wintergreen, vanillin, the amino acid tyrosine, adrenalin, and tetrahydrocannibinaol (the hallucinogen ingredient of marijuana). Phenol compounds are used as antiseptics and disinfectants, as antioxidants, and to manufacture plastics and aspirin. 

The term aromatic was first applied in the early part of the nineteenth century to compounds having an aromatic odour, which had been isolated from many volatile vegetable oils, for example benz-aldehyde (from oil of bitter almonds), methyl salicylate (from oil of wintergreen), anethole (from aniseed) and many others. Around 1800, substances designated as aromatic also included non-benzenoid compounds, largely consisting of terpenoid natural oils. (For an... 

Phenols and related compounds occur widely in nature. Tyrosine is an amino acid that occurs in proteins. Methyl salicylate is found in oil of wintergreen, eugenol is found in oil of cloves, and thymol is found in thyme. 

Natural (-)-menthol is synthesised commercially on a multi-ton scale from the inexpensive achiral precursor myrcene in an elegant application of the asymmetric 1,3-hydrogen shift (see section 6.4.2). The synthesis is so good that it competes with the traditional isolation method from oil of wintergreen. 

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