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| Methyl salicylate | |
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| IUPAC name | Methyl salicylate |
| Identifiers | |
| CAS number | 119-36-8 |
| SMILES |
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| Properties | |
| Molecular formula | C8H8O3 |
| Molar mass | 152.1494 g/mol |
| Density | 1.174 g/cm³ |
| Melting point |
-9 °C |
| Boiling point |
220 - 224 °C |
| Hazards | |
| Flash point | 101 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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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.
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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. 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.1 Aside from its toxicity, methyl salicylate may also be used by plants as a pheromone to warn other plants of pathogens such as tobacco mosaic virus.2 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, 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.
- All species of the family Spiraea, also called the Meadowsweets.
Also called oil of wintergreen, it is one of several active ingredients in Listerene mouthwash produced by the Johnson Jonhson company. "oil of wintergreen" is produced by the pressing of the wintergreen tree.
Commercial production
Methyl salicylate can be produced by esterifying 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).
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 and as an odor masking agent for some organophosphate pesticides. If applied in too high quantities it can cause stomach and kidney problems.citation needed
Due to its chemical similarities to phosphoryl chloride, Methyl salicylate (oil of wintergreen) is frequently used in the synthesis of LSD. Its inherent psychoactive properties aren't yet fully understood.
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
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 is used in some kinds of chewing gum and candy, as an alternative to the more common peppermint and spearmint oils. It can also be found as a flavoring in some formulations of root beer. It is also a potentially entertaining source of triboluminescence; 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 candy in a dark room.56
Methyl salicylate can also be used as a transfer agent, to produce a manual copy of an image on a surface.7
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 due to its similar chemical and physical properties.8
Safety
In pure form, methyl salicylate is toxic, especially when taken internally. A single teaspoon of methyl salicylate contains 7g of salicylate,9 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.10 It has proven fatal to small children in doses as small as 4 mL.11 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.12
See also
References
- ^ 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:. PMID 15537163.
- ^ Vladimir Shulaev, Paul Silverman, Ilya Raskin (20 Feb 1997). "Airborne signalling by methyl salicylate in plant pathogen resistance". Nature 385: 718–721. doi:.
- ^ Wintergreen at Drugs.com
- ^ Schiestl, F.P.; Roubik, D.W. (2004). "Odor Compound Detection in Male Euglossine Bees". Journal of Chemical Ecology 29: 253–257. doi:.
- ^ E.N. Harvey, "The luminescence of sugar wafers," Science magazine, 14 July 1939: Vol. 90. no. 2324, pp. 35–36.
- ^ "Why do Wint-O-Green Life Savers spark in the dark?", HowStuffWorks.
- ^ Image Transfer at Making-greeting-cards.com
- ^ S. L. Bartlet-Hunt et al. "A Review of Chemical Warfare Agent Simulants for the Study of Environmental Behaviour" Critical Reviews in Environmental Science and Technology, 2008: Vol. 38., pp. 112–136
- ^ Salicylate Poisoning - Patient UK
- ^ Safety data for methyl salicylate, Physical & Theoretical Chemistry Laboratory, Oxford University
- ^ Wintergreen at Drugs.com
- ^ "Muscle-Pain Reliever Is Blamed For Staten Island Runner’s Death", New York Times (2007-06-10). Retrieved on 9 June 2007.
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
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Wikipedia content modification information:
- This page was last modified on 4 December 2008, at 19:55.
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