Methyl salicylate
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Names | |||
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Preferred IUPAC name
Methyl 2-hydroxybenzoate | |||
Other names
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Identifiers | |||
3D model (
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ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard
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100.003.925 | ||
EC Number |
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IUPHAR/BPS |
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KEGG | |||
PubChem CID
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RTECS number
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UNII | |||
CompTox Dashboard (EPA)
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Properties | |||
C8H8O3 | |||
Molar mass | 152.149 g/mol | ||
Appearance | Colorless liquid | ||
Odor | Sweet, rooty | ||
Density | 1.174 g/cm3 | ||
Melting point | −8.6 °C (16.5 °F; 264.5 K) | ||
Boiling point | 222 °C (432 °F; 495 K)[2] Decomposes at 340–350 °C[1] | ||
0.639 g/L (21 °C) 0.697 g/L (30 °C)[1] | |||
Solubility | Miscible in organic solvents | ||
Solubility in acetone | 10.1 g/g (30 °C)[1] | ||
Vapor pressure | 1 mmHg (54 °C)[2] | ||
Acidity (pKa) | 9.8[3] | ||
−8.630×10−5 cm3/mol | |||
Refractive index (nD)
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1.538 | ||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards
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Harmful | ||
GHS labelling: | |||
[2] | |||
Warning | |||
H302[2] | |||
P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P337+P313, P362, P501 | |||
NFPA 704 (fire diamond) | |||
Flash point | 96 °C (205 °F; 369 K)[2] | ||
452.7 °C (846.9 °F; 725.8 K)[2] | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Methyl salicylate (oil of wintergreen or wintergreen oil) is an
Biosynthesis and occurrence
Methyl salicylate was first isolated (from the plant Gaultheria procumbens) in 1843 by the French chemist Auguste André Thomas Cahours (1813–1891), who identified it as an ester of salicylic acid and methanol.[6][7]
The biosynthesis of methyl salicylate arises via the
Methyl salicylate as a plant metabolite
Many plants produce methyl salicylate in small quantities. Methyl salicylate levels are often upregulated in response to biotic stress, especially infection by pathogens, where it plays a role in the induction of resistance. Methyl salicylate is believed to function by being metabolized to the plant hormone salicylic acid. Since methyl salicylate is volatile, these signals can spread through the air to distal parts of the same plant or even to neighboring plants, whereupon they can function as a mechanism of plant-to-plant communication, "warning" neighbors of danger.[9] Methyl salicylate is also released in some plants when they are damaged by herbivorous insects, where they may function as a cue aiding in the recruitment of predators.[10]
Some plants produce methyl salicylate in larger quantities, where it likely involved in direct defense against predators or pathogens. Examples of this latter class include: some species of the genus
Commercial production
Methyl salicylate can be produced by
Uses
Methyl salicylate is used in high concentrations as a
Methyl salicylate is used in low concentrations (0.04% and under)
Methyl salicylate is also used as a bait for attracting male
Additional applications include: used as a simulant or surrogate for the research of chemical warfare agent
Safety and toxicity
Methyl salicylate is potentially deadly, especially for young children who may accidentally ingest preparations containing methyl salicylate such as an
Most instances of human toxicity due to methyl salicylate are a result of overapplication of topical analgesics, especially involving children. Salicylate, the major metabolite of methyl salicylate, may accumulate in
Compendial status
See also
References
- ^ a b c "Methyl salicylate". chemister.ru. Archived from the original on 2014-05-24. Retrieved 2014-05-23.
- ^ a b c d e f Sigma-Aldrich Co., Methyl salicylate.
- .
- ^ .
- ^ "The Good Scents Company - Aromatic/Hydrocarbon/Inorganic Ingredients Catalog information". Archived from the original on 2019-12-06. Retrieved 2019-12-03.
- ^ Cahours, A. A. T. (1843). "Recherches sur l'huile de Gaultheria procumbens" [Investigations into the oil of Gaultheria procumbens]. Comptes Rendus. 16: 853–856. Archived from the original on 2015-11-24. Retrieved 2013-11-19.
- ^ Cahours, A. A. T. (1843). "Sur quelques réactions du salicylate de méthylène" [On some reactions of methyl salicylate]. Comptes Rendus. 17: 43–47. Archived from the original on 2015-11-25. Retrieved 2013-11-19.
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- ^ "Topical analgesics introduction". Medicine.ox.ac.uk. 2003-05-26. Archived from the original on 2012-08-04. Retrieved 2012-11-07.
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- ^ a b Wintergreen Archived 2018-03-19 at the Wayback Machine at Drugs.com
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- ^ "Why do Wint-O-Green Life Savers spark in the dark?". HowStuffWorks. Archived from the original on 2007-08-17. Retrieved 2008-04-27.
- ^ Listerine. "Original Listerine Antiseptic Mouthwash". Archived from the original on 17 February 2015. Retrieved 25 March 2015.
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- ^ Altman, J. S.; Tyrer, N. M. (1980). "Filling selected neurons with cobalt through cut axons". In Strausfeld, N. J.; Miller, T. A. (eds.). Neuroanatomical Techniques. Springer-Verlag. pp. 373–402.
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- ^ "MG Chemicals – Rubber Renue Safety Data Sheet" (PDF). Archived from the original (PDF) on 2015-06-26.
- ^ Modrak, Rebekah and Bill Anthes. "Image Transfer & Rubbing Techniques – Reframing Photography". www.reframingphotography.com. Retrieved 2021-09-07.
- ^ "Salicylate Poisoning – Patient UK". Patient.info. 2011-04-20. Archived from the original on 2015-08-18. Retrieved 2013-07-01.
- ISBN 978-0-07-180184-3.
- ^ "Safety (MSDS) data for methyl salicylate". University of Oxford Department of Chemistry MSDS. 2010-09-15. Archived from the original on 2011-06-07. Retrieved 2023-04-24.
- ^ "Methyl Salicyclate" (PDF). CAMEO Chemicals. June 1999. Archived (PDF) from the original on 29 Dec 2016. Retrieved 24 Apr 2023.
- ^ "Muscle-Pain Reliever Is Blamed For Staten Island Runner's Death". New York Times. 10 June 2007. Archived from the original on 18 January 2018. Retrieved 22 February 2017.
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- ^ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 5 July 2009.
- ^ "NIHS Japan". Moldb.nihs.go.jp. Archived from the original on 2013-02-17. Retrieved 2013-07-01.