Methyl salicylate
Organic compound used as flavoring, fragrance, and analgesic.
Last updated
Graeme Campbell · Public domain
It is a colorless, viscous liquid with a sweet, fruity odor reminiscent of root beer.[1] Salicylic acid's methyl ester is the organic compound known as methyl salicylate.[1] Wintergreens are among the many plant species that generate this substance.[1]
Quick Facts
- Chemical formula
- C8H8O3
- First isolated by
- Auguste André Thomas Cahours
- Source plant
- Gaultheria procumbens
- Common names
- oil of wintergreen, wintergreen oil
- Uses
- flavoring
- fragrance
- analgesic
- rubefacient
- antiseptic
Facts from the source article.
Key facts and history
French chemist Auguste André Thomas Cahours first isolated methyl salicylate from the plant Gaultheria procumbens in 1843.[2] Methyl salicylate is used in high concentrations as a rubefacient and analgesic in deep heating liniments to treat joint and muscular pain.[3] A cytochrome P450 enzyme hydroxylates benzoic acid, and then a methyltransferase reacts with the product to biosynthesize methyl salicylate.[4] Pathogen infection is one type of biotic stress that often causes elevated levels of methyl salicylate in plants, which normally produce only small amounts.[5]
The plant hormone salicylic acid is thought to be the active form after methyl salicylate is metabolized.[5] Because methyl salicylate evaporates easily, airborne signals can travel to other parts of the same plant or to nearby plants.[5] Direct defense against herbivores or pathogens is a likely role for methyl salicylate in plants that generate it in substantial amounts.[6]
What the research sources say
Rodriguez-Saona, Kaplan, Braasch, and Chinnasamy published a 2011 meta-analysis in Biological Control on how predaceous arthropods respond to methyl salicylate in the field.[7]
References
- Wikipedia, "Methyl salicylate" (CC BY-SA 4.0), which cites: Markus, "Determination of Methyl Salicylate in Root Beer", Journal of AOAC International, 13 February 2020, p. 1002–1004; "methyl salicylate", scentsandflavors.com (we also read that source) en.wikipedia.org
- Wikipedia, "Methyl salicylate" (CC BY-SA 4.0), which cites: Cahours, "Recherches sur l'huile de Gaultheria procumbens", Comptes Rendus, 1843, p. 853–856; Cahours, "Sur quelques réactions du salicylate de méthylène", Comptes Rendus, 1843, p. 43–47 (original not read by us) en.wikipedia.org
- Wikipedia, "Methyl salicylate" (CC BY-SA 4.0), which cites: "Topical analgesics introduction", Medicine.ox.ac.uk, 2003-05-26; Mason, "Systematic review of efficacy of topical rubefacients containing salicylates for the treatment of acute and chronic pain", British Medical Journal, 2004, p. 995; Tramer, "It's not just about rubbing—topical capsaicin and topical salicylates may be useful as adjuvants to conventional pain treatment", British Medical Journal, 2004, p. 998 (original not read by us) en.wikipedia.org
- Wikipedia, "Methyl salicylate" (CC BY-SA 4.0), which cites: Vogt, "Phenylpropanoid Biosynthesis", Molecular Plant, 2010, p. 2–20 (original not read by us) en.wikipedia.org
- Wikipedia, "Methyl salicylate" (CC BY-SA 4.0), which cites: Shulaev, "Airborne signalling by methyl salicylate in plant pathogen resistance", Nature, 1997, p. 718–721; James, "Field-testing of methyl salicylate for recruitment and retention of beneficial insects in grapes and hops", Journal of Chemical Ecology, 2004, p. 1613–1628; Rodriguez-Saona, "Field responses of predaceous arthropods to methyl salicylate: A meta-analysis and case study in cranberries", Biological Control, November 2011, p. 294–303 (we also read that source) en.wikipedia.org
- Wikipedia, "Methyl salicylate" (CC BY-SA 4.0), which cites: Knudsen, "Trends in floral scent chemistry in pollination syndromes: floral scent composition in moth-pollinated taxa", Botanical Journal of the Linnean Society, 1993, p. 263–284; Cordeiro, "Nocturnal floral scent profiles of Myrtaceae fruit crops", Phytochemistry, 2019, p. 193–198 (we also read that source) en.wikipedia.org
- Cesar Rodriguez‐Saona, "Field responses of predaceous arthropods to methyl salicylate: A meta-analysis and case study in cranberries", Biological Control (2011), doi:10.1016/j.biocontrol.2011.06.017. OpenAlex metadata CC0; paper not read. doi.org
Each numbered sentence above was checked against the source it cites before publication. Sentences citing Wikipedia adapt text from the English Wikipedia article Methyl salicylate (contributors), used under CC BY-SA 4.0; this entry is available under the same licence. Other sources were used for facts only; no text or images are copied from them.
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Sources
Compiled from Wikipedia and the sources listed below. Text from Wikipedia is available under CC BY-SA 4.0; this entry is adapted from it.
- Wikipedia: Methyl salicylate (CC BY-SA 4.0).
- Word definitions: the , each quoted from its Wikipedia article.
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