Methyl salicylate
Chemical name	Methyl salicylate
Chemical formula	C8H8O3
Molecular mass	152.1494 g/mol
CAS number	[119-36-8]
Density	1.174 g/cm³
Melting point	-9 °C
Boiling point	220 - 224 °C
Flash Point	101 °C
CAS number	[119-36-8] [1]
SMILES	c1(O)ccccc1C(=O)OC
Disclaimer and references

Methyl salicylate (chemical formula 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 plants. Some of the plants producing it are called wintergreens, hence the common name. Image File history File links Download high resolution version (813x695, 3 KB) Description: Chemical structure of Methyl salicylate. ... Image File history File links Size of this preview: 662 × 599 pixelsFull resolution (1320 × 1195 pixel, file size: 170 KB, MIME type: image/png) File historyClick on a date/time to view the file as it appeared at that time. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... This article or section does not cite any references or sources. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... For other uses, see Density (disambiguation). ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ... Italic text This article is about the boiling point of liquids. ... For other uses, see Flash point (disambiguation). ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... This article or section does not cite any references or sources. ... For other uses, see Plant (disambiguation). ... Wintergreen was originally a term referring to a plant that continues photosynthesis (i. ...

Botanical background

Plants containing methyl salicylate produce this organic ester (a combination of an organic acid with an alcohol) most likely as an anti-herbivore defense. Aside from its toxicity, methyl salicylate may be used by plants as a pheromone to warn other plants of pathogens such as tobacco mosaic virus.^[1] 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.^[2] Numerous plants produce methyl salicylate in very small amounts. A carboxylic acid ester. ... An organic acid is an organic compound that is an acid. ... This article does not cite any references or sources. ... A deer and two fawns feeding on some foliage A herbivore is often defined as any organism that eats only plants[1]. By that definition, many fungi, some bacteria, many animals, about 1% of flowering plants and some protists can be considered herbivores. ... Fanning honeybee exposes Nasonov gland (white-at tip of abdomen) releasing pheromone to entice swarm into an empty hive A pheromone is a chemical that triggers an innate behavioural response in another member of the same species. ... A pathogen or infectious agent is a biological agent that causes disease or illness to its host. ... This article does not cite any references or sources. ... For most people, when they think of insects, they think of pests such as mosquitoes or tomato worms. ...

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

• Most species of the family Pyrolaceae, particularly those in the genus Pyrola.
• Some species of the genus Gaultheria in the family Ericaceae.
• Some species of the genus Betula in the family Betulaceae, particularly those in the subgenus Betulenta.

Genera Chimaphila Moneses Orthilia Pyrola The Pyrolaceae is a small family of plants, closely related to the heather family Ericaceae, and included in it by some botanists. ... Species About 30 species, including: Pyrola americana Pyrola asarifolia Pyrola chlorantha Pyrola elliptica Pyrola grandiflora Pyrola media Pyrola minor Pyrola norvegica Pyrola picta Pyrola rotundifolia Pyrola is a genus of evergreen herbaceous plants in the family Pyrolaceae. ... Species About 170 species, including: Gaultheria adenothrix Gaultheria antarctica Gaultheria antipoda Gaultheria caudata Gaultheria codonantha Gaultheria cumingiana Gaultheria cuneata Gaultheria depressa Gaultheria eriophylla Gaultheria forrestii Gaultheria fragrantissima Gaultheria hirtiflora Gaultheria hispida Gaultheria hispidula Gaultheria hookeri Gaultheria humifusa Gaultheria insana Gaultheria itoana Gaultheria lanceolata Gaultheria macrostigma Gaultheria miqueliana Gaultheria mucronata Gaultheria... Genera See text The plant Family Ericaceae (Heath Family) or ericaceous plants are mostly lime-hating or calcifuge plants that thrive in acid soils. ... Species Many species; see text and classification Birch is the name of any tree of the genus Betula, in the family Betulaceae, closely related to the beech/oak family, Fagaceae. ... Genera Alnus - Alder Betula - Birch Carpinus - Hornbeam Corylus - Hazel Ostrya - Hop-hornbeam Ostryopsis - Hazel-hornbeam 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. ... Subgenus Betulenta - Wintergreen oil birches Bark on twigs rich in methyl salicylate (oil of wintergreen). ...

Commercial production

Methyl salicylate can be produced by esterifiying salicylic acid with methanol. 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). Esterification is the general name for a chemical reaction in which two chemicals (typically an alcohol and an acid) form an ester as the reaction product. ... Methanol, also known as methyl alcohol, carbinol, wood alcohol, wood naptha or wood spirits, is a chemical compound with chemical formula CH3OH. It is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid with a distinctive odor that is somewhat milder and sweeter than ethanol (ethyl alcohol). ... Binomial name Betula lenta L. Sweet Birch (Betula lenta), also known as Cherry Birch or Black Birch, is a species of birch native to eastern North America, from southern Maine west to southernmost Ontario and southern Michigan, and south in the Appalachian Mountains to northern Georgia. ... Binomial name Gaultheria procumbens L. Eastern Teaberry (Gaultheria procumbens), also known as Checkerberry, Boxberry and American Wintergreen, is a small shrub native to northeastern North America. ...

Uses

It is used as a rubefacient in deep heating liniments, and in small amounts as a flavoring agent at no more than 0.04%.^[3] It is also used to provide fragrance to various products. It is also used as an odor masking agent for some organophosphate pesticides. If applied in too high quantities it can cause stomach and kidney problems.^{[citation needed]} Herbal rubefacients are applied externally, causing dilation of the capillaries and an increase in blood circulation. ... Liniment, from the Latin linere, to anoint, is a medicinal preparation meant for external use, but one that is thinner in consistency than an ointment. ... Flavouring (or flavoring) is a product which is added to food in order to change or augment its taste. ... Odor receptors on the antennae of a Luna moth An odor is the object of perception of the sense of olfaction. ... An organophosphate (sometimes abbreviated OP) is the general name for esters of phosphoric acid and is one of the organophosphorus compounds. ... the plane is spreading pesticide. ...

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. ^[4] Genera Aglae Euglossa Eulaema Eufriesea Exaerete Euglossine bees, also called orchid bees, are the only group of corbiculate bees which do not all possess eusocial behavior. ...

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.^{[citation needed]}

Methyl salicylate can also be used as a transfer agent, to produce a manual copy of an image on a surface.^[5]

Safety

In pure form, methyl salicylate is toxic, especially when taken internally. The lowest published lethal dose is 101 mg/kg body weight in adult humans.^[6] It has proven fatal to small children in doses as small as 4 mL.^[7] A 17 year-old cross-country runner at Notre Dame Academy on Staten Island, died April 3, 2007, after her body absorbed high levels of methyl salicylate through excessive use of topical muscle-pain relief products.^[8] US Armed Forces cross country meet Cross-country running is a sport in which teams of runners compete to complete a course over open or rough terrain before other teams. ... Staten Island (IPA: ) is one of the five boroughs of New York City. ...

See also

• Salicylic acid

Salicylic acid is the chemical compound with the formula C6H4(OH)CO2H, where the OH group is adjacent to the carboxyl group. ...

References

1. ^ Vladimir Shulaev, Paul Silverman, Ilya Raskin (20 Feb 1997). "Airborne signalling by methyl salicylate in plant pathogen resistance". Nature 385: 718 - 721. DOI:10.1038/385718a0. 
2. ^ D. G. James, T. S. Price (Aug 2004). "Field-testing of methyl salicylate for recruitment and retention of beneficial insects in grapes and hops". J. Chem. Ecol. 30 (8): 1613-28. DOI:10.1023/B:JOEC.0000042072.18151.6f. PMID 15537163. 
3. ^ Wintergreen at Drugs.com
4. ^ Schiestl, F.P.; Roubik, D.W. (2004). "Odor Compound Detection in Male Euglossine Bees.". Journal of Chemical Ecology 29: 253-257. DOI:10.1023/A:1021932131526. 
5. ^ Image Transfer at Making-greeting-cards.com
6. ^ Safety data for methyl salicylate, Physical & Theoretical Chemistry Laboratory, Oxford University
7. ^ Wintergreen at Drugs.com
8. ^ "Muscle-Pain Reliever Is Blamed For Staten Island Runner’s Death", New York Times, 2007-06-10. Retrieved on 2007-06-09. 

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External links

Toxicity

• MedlinePlus - Methyl salicylate overdose
• MedlinePlus - Sports cream overdose
• CNN - Medical examiner: Sports cream caused teen's death
• NLM Hazardous Substances Databank – Methyl salicylate