Methyl salicylate

Methyl salicylate
Oil of wintergreen
Oil of wintergreen

Yellowish, oily, characteristic smelling liquid

Liquid

1.18 g · cm -3

-8.3 ° C

223 ° C

13 Pa (20 ° C)

Slightly soluble in water ( 0.74 g · l-1 at 30 ° C)
Soluble in ethanol, glacial acetic acid, ethers and fatty and essential oils

1.535 (20 ° C)

Attention

887 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

Methyl salicylate, and methyl salicylate, the methyl ester of salicylic acid. Methyl salicylate is also known as oil of wintergreen or wintergreen oil, because it can be isolated by steam distillation from the leaves of the genera Pyrola ( wintergreen ) and Gaultheria ( false fruits ).

Occurrence

Plants that produce larger ( riechbare ) quantities:

Most species of the family Ericaceae ( heath family), especially those of the genus Pyrola ( wintergreen ).
Some species of Gaultheria ( wintergreen shrubs ) in the family Ericaceae ( heath family).
Some species of Betula ( birch ) in the family Betulaceae (birch family)

Production

Salicylic acid methyl ester is obtained by esterification of salicylic acid with methanol, wherein sulfuric acid is used as the catalyst:

Use

Methyl salicylate is used externally, used in alternative medicine in the form of bath salts together with essential birch oil for rheumatic complaints. In addition, it is used in perfumery, food and cosmetics, because it has a very distinctive smell.

Offer in North America as well as all the chewing gum manufacturer in addition to the classic flavors like peppermint the taste of wintergreen, is contained in the methyl salicylate. In Europe, this flavor in chewing gum has been unable to enforce; many Europeans feel the taste to be clinically similar to dentist and not tasty. Also in the snus flavor in America and Scandinavia is often offered.

That in Germany still most widely known product with wintergreen flavor is the chewing gum brand Bazooka of the U.S. producer Topps Company, which was produced until the late eighties by German confectioner August Storck under license and marketed. Today wintergreen chewing gum and lozenges in Germany are only available as an import of goods, for example, in American outlet stores.

Side Effects and Limitations

Methyl salicylate should not be used during pregnancy. With regular use, the substance that is absorbed through the skin, cause symptoms of overdose. These are manifested by gastrointestinal and / or renal pain. The 17 -year-old athlete Arielle Newman to have died of an overdose of the drug.

Mesotan

Due to intense odors they tried in front of Farbenfabriken. Friedr. Bayer & Co. offer salicylic acid methoxymethyl ester as an alternative. He was introduced by Arthur Green Oak in the pharmaceutical newspaper from 1902 under the trade name Mesotan.

Botanical background

Methyl salicylate can be toxic, especially if ingested. Plants containing methyl salicylate, it could have developed as a deterrent against predators. Methyl salicylate can also be used by plants as a pheromone to warn other plants against pathogens, such as the tobacco mosaic virus. If the plant is infested by insects, methyl salicylate can serve as Anlockstoff for beneficial insects that kill the invading insects. Many plants produce small amounts of methyl salicylate.

Chemical Properties

Methyl salicylate may be nitrated with iron ( III) nitrate. The result is an isomeric mixture of the 3 - and 5-nitro derivative. In the presence of nitric acid is produced mainly 5 - Nitrosalicylsäuremethylester, in a basic medium mainly 3- Nitrosalicylsäuremethylester.

Acetylation of salicylic acid methyl ester with acetic anhydride in the presence of aluminum chloride as the catalyst takes place in very good yields of the 5-position.

By reaction with sodium hypochlorite for up to two chlorine atoms can be introduced into the benzene nucleus, it is produced 3,5- Dichlorsalicylsäuremethylester.

In the reaction with elemental bromine is a bromine atom is attached to the 5-position.