Methyl salicylate

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Methyl salicylate

Methyl salicylate (chemical formula

Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
C₆H₄(HO)COOCH₃; also known as salicylic acid methyl ester, oil of wintergreen, betula oil, methyl-2-hydroxybenzoate) is a natural product of many species of plant

Plant

Plants are Life organisms belonging to the Kingdom Plantae. They include familiar organisms such as trees, herbs, bushes, grasses, vines, ferns, mosses, and green algae....
s. Some of the plants producing it are called wintergreen

Wintergreen

Wintergreen is a group of plants. Wintergreen once commonly referred to plants that continue photosynthesis throughout the winter. The term evergreen is now more commonly used for this characteristic....
s, hence the common name.

ts containing methyl salicylate produce this organic ester

Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
(a combination of an organic acid

Organic acid

An organic acid is an organic compound with acidic properties. The most common organic acids are the carboxylic acids whose acidity is associated with their carboxyl group -COOH....
with an alcohol

Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
) most likely as an anti-herbivore

Herbivore

Herbivory is a form of predation in which an organism, known as an herbivore, heterotrophs principally autotrophs such as plants, algae and photosynthesizing bacteria....
defense.

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Botanical background

Plants containing methyl salicylate produce this organic ester

Ester

Organic acid

Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
) most likely as an anti-herbivore

Herbivore

Herbivory is a form of predation in which an organism, known as an herbivore, heterotrophs principally autotrophs such as plants, algae and photosynthesizing bacteria....
defense. If the plant is infested with herbivorous insects, the release of methyl salicylate may function as an aid in the recruitment of beneficial insects to kill the herbivorous insects. Aside from its toxicity, methyl salicylate may also be used by plants as a pheromone

Pheromone

A pheromone is a chemical that triggers a natural behavioral response in another member of the opposite gender of the same species. There are alarm signal pheromones, food trail pheromones, sex pheromones, and many others that affect behavior or physiology....
to warn other plants of pathogen

Pathogen

A pathogen , infectious agent, or germ, is a biological agent that causes disease or illness to its Host .There are several substrates and pathways whereby pathogens can invade a host; the principal pathways have different episodic time frames, but soil contamination has the longest or most persistent potential for harboring...
s such as tobacco mosaic virus

Tobacco mosaic virus

Tobacco mosaic virus is an RNA virus that infects plants, especially tobacco and other members of the family Solanaceae. The infection causes characteristic patterns on the Leaf ....
. Numerous plants produce methyl salicylate in very small amounts.

Plants producing it in significant amounts (readily detected by scent) include:

Most species of the family Pyrolaceae
Pyrolaceae

Pyrolaceae was a small family of flowering plants under the old Cronquist system of plant classification. It included the four genus Chimaphila, Moneses, Orthilia, and Pyrola, and sometimes also the eight genera formerly usually placed in the family Monotropaceae....
, particularly those in the genus Pyrola
Pyrola

Pyrola is a genus of evergreen herbaceous plants in the family Ericaceae. Under the old Cronquist system it was placed in its own family Pyrolaceae, but genetic research showed it belonged in the family Ericaceae....
.
Some species of the genus Gaultheria
Gaultheria

Gaultheria is a genus of about 170-180 species of shrubs in the family Ericaceae. The name memorializes M. Hugues Gauthier of Quebec, a mis-spelt honour bestowed by the Scandinavian Pehr Kalm in 1748....
in the family Ericaceae
Ericaceae

The plant family Ericaceae are mostly calcium oxide-hating plants that thrive in acid soils. Many well-known plants of the Ericaceae live in temperate climates, such as cranberry, blueberry, Erica, Calluna vulgaris, huckleberry, azalea and rhododendron....
.
Some species of the genus Betula
Birch

Birch is the name of any tree of the genus Betula , in the family Betulaceae, closely related to the beech/oak family, Fagaceae....
in the family Betulaceae
Betulaceae

Betulaceae, or the Birch Family, includes six genera of deciduous nut -bearing trees and shrubs, including the birches, alders, hazels, hornbeams and hop-hornbeams, numbering about 130 species....
, particularly those in the subgenus Betulenta
Betula classification

Subgenus Betulenta - Wintergreen oil birchesBark on twigs rich in methyl salicylate . Female catkins erect.*Diploid .**Sweet Birch - Sweet Birch or Cherry Birch...
.
All species of the family Spiraea
Spiraea

'Spiraea' is a genus of about 80-100 species of shrubs in the Rosaceae, subfamily Spiraeoideae. They are native to the temperate Northern Hemisphere, with the greatest diversity in eastern Asia....
, also called the Meadowsweets.

Also called oil of wintergreen, it is one of several active ingredients in Listerine

Listerine

Listerine is a brand name for antiseptic mouthwash. Its original formula has notoriously strong flavor, although variations have been released that are marketed as tasting milder....
mouthwash produced by the Johnson & Johnson

Johnson & Johnson

Johnson & Johnson is a global United States pharmaceutical, medical devices and consumer packaged goods manufacturer founded in 1886. Its common stock is a component of the Dow Jones Industrial Average and the company is listed among the Fortune 500....
company.

Commercial production

Methyl salicylate can be produced by esterifying

Esterification

Esterification is the general name for a chemical reaction in which two reactants form an ester as the product . Esters are common in organic chemistry and biological materials, and often have a characteristic pleasant, fruity odor....
salicylic acid

Salicylic acid

Salicylic acid is a beta hydroxy acid with the chemical formula C6H4COOH, where the OH group is adjacent to the carboxylic acid....
with methanol

Methanol

Methanol, also known as methyl alcohol, carbinol, wood alcohol, wood naphtha or wood spirits, is a chemical compound with chemical formula carbonhydrogen3oxygenhydrogen ....
. Commercial methyl salicylate is now synthesized, but in the past, it was commonly distilled from the twigs of Sweet Birch (Betula lenta) and Eastern Teaberry (Gaultheria procumbens).

Uses

It is used as a rubefacient

Rubefacient

A rubefacient is a substance for external application that produces redness of the skin e.g. by causing dilation of the capillary and an increase in blood circulation....
in deep heating liniment

Liniment

File:Herb Knudson's Surgical 11.jpgLiniment, from the Latin linere, to anoint, is a medicated topical preparation for application to the skin....
s, and in small amounts as a flavoring agent at no more than 0.04%. It is also used to provide fragrance to various products and as an odor masking agent for some organophosphate

Organophosphate

An organophosphate is the general name for esters of phosphoric acid. Phosphates are probably the most pervasive organophosphorus compounds. Many of the most important biochemicals are organophosphates, including DNA and RNA as well as many cofactor s that are essential for life....
pesticides. If applied in too high quantities it can cause stomach and kidney problems.

It is one of many compounds that is attractive to males of various species of orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.

Methyl salicylate also has the ability to clear plant or animal tissue samples of color, and as such is useful for microscopy and immunohistochemistry when excess pigments obscure structures or block light in the tissue being examined. This clearing generally only takes a few minutes, but the tissue must first be dehydrated in alcohol.

Methyl salicylate, though its source plants are not true mints

Mentha

Mentha is a genus of about 25 species of flowering plants in the Family Lamiaceae . Species within Mentha have a cosmopolitan distribution distribution across Europe, Africa, Asia, Australia, and North America....
, is also used as a mint in some kinds of chewing gum

Chewing gum

Chewing gum is a type of confection traditionally made of chicle, a natural latex product, or synthetic rubber. For reasons of economy and quality, many modern chewing gums use rubber instead of chicle....
and candy, as an alternative to the more common peppermint

Peppermint

Peppermint is a Hybrid Mentha, a cross between the watermint and spearmint . The plant, indigenous to Europe, is now widespread in cultivation throughout all regions of the world....
and spearmint

Spearmint

Mentha spicata is a species of Mentha native to much of Europe and southwest Asia, though its exact natural range is uncertain due to extensive early cultivation....
oils. It can also be found as a flavoring in some formulations of root beer

Root beer

Root beer is a carbonated beverage originally brewed using sassafras. Root beer, popularized in North America, comes in two forms: fermentation and soft drink....
. It is also a potentially entertaining source of triboluminescence

Triboluminescence

Triboluminescence is an optical phenomenon in which light is generated when asymmetrical crystal bonds in a material are broken when that material is scratched, crushed, or rubbed....
; when mixed with sugar and dried, it gains the tendency to build up electrical charge when ground. This effect can be observed by crushing wintergreen Life Savers

Life Savers

Life Savers is an United States brand of ring-shaped mint and artificially fruit-flavored candy. The candy is known for its distinctive packaging, coming in aluminium foil rolls....
candy in a dark room.

Methyl salicylate can also be used as a transfer agent, to produce a manual copy of an image on a surface.

Methyl salicylate is added in small amounts to glacial acetic acid to lower its freezing point while travelling in cold countries.

Methyl salicylate is also used as a simulant or surrogate for the research and investigation of the chemical warfare agent, sulfur mustard

Sulfur mustard

The sulfur mustards, of which mustard gas is a member, are a class of related cytotoxic, vesicant chemical warfare agents with the ability to form large blisters on exposed skin....
due to its similar chemical and physical properties.

Safety

In pure form, methyl salicylate is toxic, especially when taken internally. A single teaspoon of methyl salicylate contains 7g of salicylate, which is equivalent to more than twenty-three 300mg aspirin tablets. The lowest published lethal dose is 101 mg/kg body weight in adult humans. It has proven fatal to small children in doses as small as 4 mL. A 17 year-old cross-country runner at Notre Dame Academy on Staten Island

Staten Island

Staten Island is a borough of New York City, situated almost entirely on the island of the same name in the extreme southwest part of the city....
, died April 3, 2007, after her body absorbed high levels of methyl salicylate through excessive use of topical muscle-pain relief products.

External links

Toxicity:

Methyl salicylate

Botanical background

Commercial production

Uses

Safety

See also

External links