Oil of Wintergreen

I. Methyl salicylate test. Heat i ml. of methanol with 0 5 g. of sodium sdicylate (or free salicylic acid) and a few drops of cone. H2SO4 gently for i minute. Cool, pour into a few ml. of cold water in a boiling-tube, and shake. Note the odour of methyl salicylate (oil of wintergreen). 

Salicylic Acid. Ester has strong odour of oil of wintergreen. 

One of the hydroxybenzoic acids is known by the common name salicylic acid Its methyl ester methyl salicylate occurs in oil of wintergreen Methyl salicylate boils over 50°C lower than either of the other two methyl hydroxybenzoates What is the structure of methyl salicylate Why is its boiling point so much lower than that of either of its regioisomers ... 

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 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). 

This alcohol, the lowest of the paraffin series, is found in the distillation waters of a number of essential oils, being soluble in all proportions in water. It does not therefore form a constituent of essential oils in the form in which they are found in commerce. In the form of esters, methyl alcohol is found as a constituent of a number of essential oils, such as, for example, oil of wintergreen, which consists almost entirely of methyl salicylate. Methyl alcohol, CH OH, is a liquid of specific gravity 0 810, boiling at 64°. 

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. 

Salicylic acid is quite useful, its methyl ester has a sharp, characteristic odor and is called oil of wintergreen."... 

OH molecules, reaction between, 282 Oil-drop experiment, 241 Oil of wintergreen, 346 Oleomargarine, 407 Open hearth furnace, 404 Operational definition, 195 Orbital representation of chemical bonding, 278 Orbitals atomic, 262, 263 dand/, 262... 

Salicylic acid reacts with acetic acid to produce acetylsalicylic acid the active ingredient in aspirin. It also reacts with methanol to form methyl salicylate, more commonly known as oil of wintergreen. 

Oil of wintergreen salicylic acid methyl ester methyl sweet birch oil betula oil... 

See also methacrylate odor absorbers, 169 oil drilling mud, 146 oil of wintergreen, 167, 186. See also methyl salicylate... 

The ester you produced has the common name oil of wintergreen. Write a chemical equation using names and structural formulas for the reaction that produced the ester. 

Research the organic compounds that are responsible for the smell and taste of oranges, pineapples, pears, oil of wintergreen, and apples. Find and record the chemical structure of each compound. 

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 ... 

Of the 400 volatiles detected in the tomato, only 17 have a positive impact on the flavor profile. Two of the most important ones are also key players in the aroma of roses p-ionone and p-damascenone. Another player is methyl salicylate, a compound we previously encountered in oil of wintergreen. Some of the most important flavor elements are present in very small concentrations but can be perceived by us at these extremely small concentrations. 

Aspirin is the most widely used medication. Over 10,000 tons of aspirin are used in this country annually, and worldwide the annual consumption is 35,000 tons. The history of acetylsalicylic acid actually goes back thousands of years. Hippocrates (460-377 B.c.) and the ancient Greeks used powdered willow bark and leaves to reduce fever (antipyretic) and as a pain reliever (analgesic). Native American populations also used willow and oil of wintergreen for medication. The chemicals responsible for the medicinal properties in willow and oil of wintergreen are forms of salicylates. Willows (genus Salix) contain salicin and oil of wintergreen contains methyl salicylate. 

Flavouring agents— Flavouring agents e.g. peppermint, spearmint, menthol, cinnamon, oil of wintergreen (methyl salicylate) are used in conjunction with alcohol and humectants to overcome disagreeable taste. 

Problem 19.19 Use phenol and any inorganic or aliphatic reagents to synthesize (a) aspirin (acetyisalicyclic acid), (b) oil of wintergreen (methyl salicylate). Do not repeat the synthesis of any compound. 

Salicylic acid may be obtained (1) from oil of wintergreen, which contains methyl salicylate, or (2) by heating dry sodium phenate C6H ONa plus carbon dioxide under pressure at 130 2 and recovenng from the resulting sodium salicylate by adding dilute sulfuric acid. 

Methyl 2-hydroxybenzoate (methyl salicylate, oil of wintergreen) occurs in many plants, but it also is readily prepared synthetically by esterification of... 

Salicylic acid (m.p. 157-159°C) is a crystalline solid widely used in the General Chemistry laboratory. All but three of the lab manuals examined use salicylic acid, usually for making aspirin or oil of wintergreen. When handled properly, salicylic acid should pose no significant hazard for students in the laboratory. The only appreciable uptake of this compound that might occur would be through inhalation of the tiny particles picked up and carried by the air stream. This can be minimized by avoiding work areas where there is air turbulence or ventilation currents. 

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