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Revision as of 22:36, 18 September 2011 editLarryMorseDCOhio (talk | contribs)2,615 edits →Botanical background: Image of wintergreen plants added; misc. other edits and additions.← Previous edit		Latest revision as of 03:59, 7 October 2024 edit undo100.1.148.217 (talk) →Methyl salicylate as a plant metabolite
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			{{Chembox
	{{lead too short|date=August 2011}}
			| Watchedfields = changed
	{{chembox
	| verifiedrevid = 446251148		| verifiedrevid = 451225512
	| Name = Methyl salicylate		| Name = Methyl salicylate
			| ImageFile1 = Methyl salicylate.svg
	| ImageFileL1 = Salicylic acid methyl ester chemical structure.png
			| ImageSize1 = 150
	| ImageSizeL1 = 120px
			| ImageAlt1 = Skeletal formula
	| ImageFileR1 = Methyl-salicylate-3D-vdW.png
			| ImageFileL2 = Methyl salicylate 3D ball.png
	| ImageSizeR1 = 120px
			| ImageSizeL2 = 120
	| ImageNameR1 = Methyl salicylate in 3D
			| ImageAltL2 = Ball-and-stick model
	| IUPACName = Methyl 2-hydroxybenzoate
			| ImageFileR2 = Methyl salicylate 3D spacefill.png
	| OtherNames = Salicylic acid methyl ester; Oil of wintergreen; Betula oil; Methyl 2-hydroxybenzoate
			| ImageSizeR2 = 120
	| Section1 = {{Chembox Identifiers
			| ImageAltR2 = Space-filling model
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ImageFile3 = Sample of methyl salicylate.jpg
			| ImageSize3 = 120px
			| ImageAlt3 = Sample of a clear liquid
			| PIN = Methyl 2-hydroxybenzoate
			| OtherNames = {{unbulleted list|Salicylic acid methyl ester|Oil of wintergreen|Betula oil}}
			|Section1={{Chembox Identifiers
			| IUPHAR_ligand = 2431
			| PubChem = 4133
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 13848808		| ChemSpiderID = 13848808
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
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	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = D01087		| KEGG = D01087
			| EC_number = 204-317-7
	| SMILES = O=C(OC)c1ccccc1O
			| ChEBI = 31832
	}}
			| RTECS = VO4725000
	| Section2 = {{Chembox Properties
			| SMILES = O=C(OC)c1ccccc1O
	| Formula = C<sub>8</sub>H<sub>8</sub>O<sub>3</sub>
			}}
	| MolarMass = 152.1494 g/mol
			|Section2={{Chembox Properties
	| Density = 1.174 g/cm³
	| MeltingPtC = -9		| C=8 | H=8 | O=3
			| MolarMassUnit = g/mol
	| BoilingPt = 220 - 224 °C
			| Appearance = Colorless liquid
	}}
			| Odor = Sweet, rooty
	| Section7 = {{Chembox Hazards
			| Density = 1.174{{nbsp}}g/cm<sup>3</sup>
	| FlashPt = 101 °C
			| MeltingPtC = −8.6
			| BoilingPtC = 222
			| BoilingPt_ref = <ref name="sigma" /><br> Decomposes at 340–350{{nbsp}}°C<ref name=chemister />
			| RefractIndex = 1.538
			| Solubility = 0.639{{nbsp}}g/L (21{{nbsp}}°C)<br> 0.697{{nbsp}}g/L (30{{nbsp}}°C)<ref name=chemister>{{cite web|url=http://chemister.ru/Database/properties-en.php?dbid=1&id=2994|title=Methyl salicylate|work=chemister.ru|access-date=2014-05-23|archive-date=2014-05-24|archive-url=https://web.archive.org/web/20140524024109/http://chemister.ru/Database/properties-en.php?dbid=1&id=2994|url-status=live}}</ref>
			| Solubility1 = 10.1{{nbsp}}g/g (30{{nbsp}}°C)<ref name=chemister />
			| Solvent1 = acetone
			| SolubleOther = Miscible in organic solvents
			| VaporPressure = 1{{nbsp}}mmHg (54{{nbsp}}°C)<ref name="sigma" />
			| pKa = 9.8<ref>{{cite journal|last1=Scully|first1=F. E.|last2=Hoigné|first2=J.|title=Rate constants for reactions of singlet oxygen with phenols and other compounds in water|journal=Chemosphere|date=January 1987|volume=16|issue=4|pages=681–694|doi=10.1016/0045-6535(87)90004-X|bibcode=1987Chmsp..16..681S}}</ref>
			| MagSus = {{val|-8.630e-5|u=cm<sup>3</sup>/mol}}
			}}
			|Section7={{Chembox Hazards
			| GHSPictograms = {{GHS07}}<ref name="sigma">{{Sigma-Aldrich|id=240826|name=Methyl salicylate|access-date=2013-05-23}}</ref>
			| GHSSignalWord = Warning
			| HPhrases = {{H-phrases|302}}<ref name="sigma" />
			| PPhrases = {{P-phrases|264|270|280|301+312|302+352|305+351+338|321|330|332+313|337+313|362|501}}
			| FlashPtC = 96
			| FlashPt_ref = <ref name="sigma" />
	| MainHazards = Harmful		| MainHazards = Harmful
			| NFPA-H = 2
	}}
			| NFPA-F = 1
			| NFPA-R = 0
			| NFPA-S =
			| AutoignitionPtC = 452.7
			| AutoignitionPt_ref = <ref name="sigma" />
			}}
	}}		}}
			'''Methyl salicylate''' ('''oil of wintergreen''' or '''wintergreen oil''') is an ] with the formula C<sub>8</sub>H<sub>8</sub>O<sub>3</sub>. It is the methyl ] of ]. It is a colorless, ] liquid with a sweet, fruity odor reminiscent of ] (in which it is used as a flavoring),<ref name="rootbeer"/> but often ] called "minty", as it is an ingredient in mint candies.<ref>{{Cite web |url=http://www.thegoodscentscompany.com/data/rw1008472.html |title=The Good Scents Company - Aromatic/Hydrocarbon/Inorganic Ingredients Catalog information |access-date=2019-12-03 |archive-date=2019-12-06 |archive-url=https://web.archive.org/web/20191206205053/http://www.thegoodscentscompany.com/data/rw1008472.html |url-status=live }}</ref> It is produced by many species of ]s, particularly ]s. It is also produced synthetically, used as a ] and as a flavoring agent.
	'''Methyl salicylate''' ('''oil of wintergreen''' or '''wintergreen oil''') is a natural product of many species of ]s. Some of the plants which produce it are called ]s, hence the common name.
			==Biosynthesis and occurrence==
	==Botanical background==
			Methyl salicylate was first isolated (from the plant '']'') in 1843 by the French chemist ] (1813–1891), who identified it as an ] of ] and ].<ref>{{cite journal|last=Cahours|first=A. A. T.|author-link=Auguste André Thomas Cahours|date=1843|url=http://gallica.bnf.fr/ark:/12148/bpt6k29751/f853.image.langEN|title=Recherches sur l'huile de ''Gaultheria procumbens''|trans-title=Investigations into the oil of ''Gaultheria procumbens''|journal=Comptes Rendus|volume=16|pages=853–856|access-date=2013-11-19|archive-date=2015-11-24|archive-url=https://web.archive.org/web/20151124225104/http://gallica.bnf.fr/ark:/12148/bpt6k29751/f853.image.langEN|url-status=live}}</ref><ref>{{cite journal|last=Cahours|first=A. A. T.|author-link=Auguste André Thomas Cahours|date=1843|url=http://gallica.bnf.fr/ark:/12148/bpt6k2976b/f47.image.langEN|title=Sur quelques réactions du salicylate de méthylène|trans-title=On some reactions of methyl salicylate|journal=Comptes Rendus|volume=17|pages=43–47|access-date=2013-11-19|archive-date=2015-11-25|archive-url=https://web.archive.org/web/20151125200032/http://gallica.bnf.fr/ark:/12148/bpt6k2976b/f47.image.langEN|url-status=live}}</ref>
	Plants containing methyl salicylate produce this organic ] (a combination of an ] with an ]) most likely as an anti-] defense. If the plant is infected with herbivorous insects, the release of methyl salicylate may function as an aid in the recruitment of ]s to kill the herbivorous insects.<ref>{{cite journal|author=D. G. James, T. S. Price|title=Field-testing of methyl salicylate for recruitment and retention of beneficial insects in grapes and hops|journal=]|month=August|year=2004|volume=30|issue=8|pages=1613–28|pmid=15537163|doi=10.1023/B:JOEC.0000042072.18151.6f}}</ref> Aside from its toxicity, methyl salicylate may also be used by plants as a ] to warn other plants of ]s such as ].<ref>{{cite journal|journal=]|title=Airborne signalling by methyl salicylate in plant pathogen resistance|author=Vladimir Shulaev, Paul Silverman, Ilya Raskin|volume=385|pages=718–721|date=20 February 1997|doi=10.1038/385718a0|issue=6618}}</ref> Numerous plants produce methyl salicylate in very small amounts.
			The biosynthesis of methyl salicylate arises via the ] of ] by a ] followed by reaction with a ] enzyme.<ref>{{cite journal|journal=Molecular Plant|year=2010|pages=2–20|doi=10.1093/mp/ssp106|title=Phenylpropanoid Biosynthesis|last=Vogt|first=T.|pmid=20035037|volume=3|doi-access=free}}</ref>
	]'')]]
	Plants producing it in significant amounts (readily detected by scent) include:
			== Methyl salicylate as a plant metabolite ==
	*most species of the family ], particularly those in the genus '']'';
			]'')]]
	*some species of the genus '']'' in the family ], including ], the wintergreen or eastern teaberry;
			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 ]. 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 ], "warning" neighbors of danger.<ref>{{cite journal|journal=Nature|title=Airborne signalling by methyl salicylate in plant pathogen resistance|first1=V. |last1=Shulaev |first2=P. |last2=Silverman |first3=I. |last3=Raskin |volume=385|pages=718–721|date=1997|doi=10.1038/385718a0|issue=6618|bibcode = 1997Natur.385..718S |s2cid=4370291}}</ref> 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, notably ], ], and ].<ref>{{cite journal|first1=D. G.|last1=James |first2=T. S.|last2=Price |title=Field-testing of methyl salicylate for recruitment and retention of beneficial insects in grapes and hops|journal=Journal of Chemical Ecology|date=2004|volume=30|issue=8|pages=1613–1628|pmid=15537163|doi=10.1023/B:JOEC.0000042072.18151.6f|s2cid=36124603 }}</ref> <ref>Rodriguez-Saona, C., Kaplan, I., Braasch, J., Chinnasamy, D., & Williams, L. (2011). Field responses of predaceous arthropods to methyl salicylate: A meta-analysis and case study in cranberries. Biological Control, 59(2), 394-303. https://doi.org/10.1016/j.biocontrol.2011.06.017</ref>
	*some species of the genus '']'' in the family ], particularly those in the subgenus ] such as ], the black birch;
	*all species of the genus '']'' in the family ], also called the meadowsweets.
			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 '']'' in the family ], including '']'', the wintergreen or eastern teaberry; some species of the genus '']'' in the family ], particularly those in the subgenus ] such as ], the black birch; all species of the genus '']'' in the family ], also called the meadowsweets; species of the genus '']'' in the family ]. Methyl salicylate can also be a component of ]s, especially in plants dependent on nocturnal pollinators like moths,<ref>{{cite journal|last1=Knudsen |first1=J. T. |first2=L. |last2=Tollsten |date=1993 |title=Trends in floral scent chemistry in pollination syndromes: floral scent composition in moth-pollinated taxa |journal=Botanical Journal of the Linnean Society |volume=113 |issue=3 |pages=263–284 |publisher=Oxford Academic|doi=10.1111/j.1095-8339.1993.tb00340.x }}</ref> scarab beetles, and (nocturnal) bees.<ref>{{cite journal|last1=Cordeiro |first1=G. D. |first2=I. G. |last2=Fernandes dos Santos |first3=C. I. |last3=da Silva |first4=C. |last4=Schlindwein |first5=I. |last5=Alves-dos-Santos |first6=S. |last6=Dötterl |date=2019 |title=Nocturnal floral scent profiles of Myrtaceae fruit crops |journal=Phytochemistry |volume=162 |pages=193–198|doi=10.1016/j.phytochem.2019.03.011 |pmid=30939396 |s2cid=92997657 }}</ref>
	==Commercial production==		==Commercial production==
	Methyl salicylate can be produced by ] ] with ]. Commercial methyl salicylate is now synthesized, but in the past, it was commonly distilled from the twigs of ] and ].		Methyl salicylate can be produced by ] ] with ].<ref>{{Ullmann|doi=10.1002/14356007.a23_477|title=Salicylic Acid|year=2012|last1=Boullard|first1=Olivier|last2=Leblanc|first2=Henri|last3=Besson|first3=Bernard|isbn=3527306730}}</ref> Commercial methyl salicylate is now synthesized, but in the past, it was commonly distilled from the twigs of '']'' (sweet birch) and '']'' (eastern teaberry or wintergreen).
	==Uses==		==Uses==
	] ] that was treated with ] to stain the skeleton, then cleansed with 2 or 3 ] washes, and treated with methyl salicylate to make the surrounding ] transparent]]		] ] that was treated with ] to stain the skeleton, then cleansed with two or three ] washes, and treated with methyl salicylate to make the surrounding ] transparent]]
			Methyl salicylate is used in high concentrations as a ] and ] in deep heating ]s (such as ]) to treat joint and muscular pain. Randomised double blind trials report that evidence of its effectiveness is weak, but stronger for acute pain than chronic pain, and that effectiveness may be due entirely to ]. However, in the body it metabolizes into salicylates, including salicylic acid, a known ].<ref>{{cite web |url=http://www.medicine.ox.ac.uk/bandolier/booth/painpag/topical/Topintro.html |archive-url=https://archive.today/20120804155624/http://www.medicine.ox.ac.uk/bandolier/booth/painpag/topical/Topintro.html |url-status=dead |archive-date=2012-08-04 |title=Topical analgesics introduction |publisher=Medicine.ox.ac.uk |date=2003-05-26 |access-date=2012-11-07 }}</ref><ref>{{cite journal | journal = British Medical Journal | doi = 10.1136/bmj.38040.607141.EE | title = Systematic review of efficacy of topical rubefacients containing salicylates for the treatment of acute and chronic pain | year = 2004 | last1 = Mason | first1 = L. | volume = 328 | issue = 7446 | page = 995 | pmid = 15033879 | last2 = Moore | first2 = R. A. | last3 = Edwards | first3 = J. E. | last4 = McQuay | first4 = H. J. | last5 = Derry | first5 = S. | last6 = Wiffen | first6 = P. J. | pmc = 404501 }}</ref><ref>{{cite journal | journal = British Medical Journal | pmc =404503 | doi =10.1136/bmj.328.7446.998 | title = It's not just about rubbing—topical capsaicin and topical salicylates may be useful as adjuvants to conventional pain treatment | year = 2004 | last1 = Tramer | first1 = M. R. | volume = 328 | issue = 7446 | page = 998 | pmid = 15105325}}</ref>
	Methyl salicylate is used as a ] in deep heating ]s (such as ] ointment), and in small amounts as a ] agent at no more than 0.04%.<ref name="Wintergreen"> at Drugs.com</ref> It is also used to provide ] to various products and as an odor-masking agent for some ] ]. If applied in too high quantities it can cause stomach and kidney problems.<ref></ref>
			Methyl salicylate is used in low concentrations (0.04% and under)<ref name="Wintergreen"> {{Webarchive|url=https://web.archive.org/web/20180319173538/https://www.drugs.com/npp/wintergreen.html |date=2018-03-19 }} at Drugs.com</ref> as a ] agent in ],<ref name="rootbeer">{{cite journal |last=Markus |first=John R. |date=13 February 2020 |title=Determination of Methyl Salicylate in Root Beer |journal=] |volume=57 |issue=4 |pages=1002–1004 |doi=10.1093/jaoac/57.4.1002 |doi-access=free }}</ref> ], ] and ] such as ]. When mixed with sugar and dried, it is a potentially entertaining source of ], for example by crushing Wint-O-Green ] in a dark room. When crushed, sugar crystals emit light; methyl salicylate amplifies the spark because it ], absorbing ] light and re-emitting it in the visible spectrum.<ref>{{cite journal |first=E. N. |last=Harvey |title=The luminescence of sugar wafers |journal=Science |year=1939 |volume=90 |issue=2324 |pages=35–36 |doi=10.1126/science.90.2324.35 |pmid=17798129 |bibcode=1939Sci....90...35N }}</ref><ref>{{cite news | url = http://home.howstuffworks.com/question505.htm | title = Why do Wint-O-Green Life Savers spark in the dark? | publisher = ] | access-date = 2008-04-27 | archive-date = 2007-08-17 | archive-url = https://web.archive.org/web/20070817182812/http://home.howstuffworks.com/question505.htm | url-status = live }}</ref> It is used as an antiseptic in ] mouthwash produced by the ] company.<ref>{{cite web|url=https://www.listerine.com/mouthwash/antiseptic/listerine-original-mouthwash#active-ingredients|title=Original Listerine Antiseptic Mouthwash|author=Listerine|access-date=25 March 2015|author-link=Listerine|archive-date=17 February 2015|archive-url=https://web.archive.org/web/20150217045317/https://www.listerine.com/mouthwash/antiseptic/listerine-original-mouthwash#active-ingredients|url-status=live}}</ref> It provides ] to various products and as an odor-masking agent for some ] ].{{Citation needed|date=March 2012}}
	Methyl salicylate is among the compounds that attract male ]s, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.<ref>{{cite journal | doi = 10.1023/A:1021932131526 | author = Schiestl, F.P.; Roubik, D.W. | year = 2004 | title = Odor Compound Detection in Male Euglossine Bees | journal = ] | volume = 29 | pages = 253–257 | pmid=12647866}}</ref>
			Methyl salicylate is also used as a bait for attracting male ]s for study, which apparently gather the chemical to synthesize pheromones,<ref>{{cite journal | doi = 10.1023/A:1021932131526 |last1=Schiestl |first1=F. P. |last2=Roubik |first2=D. W. | year = 2004 | title = Odor Compound Detection in Male Euglossine Bees | journal = Journal of Chemical Ecology | volume = 29 | pages = 253–257 | pmid=12647866 | issue = 1|s2cid=2845587 | hdl = 20.500.11850/57276 | hdl-access = free }}</ref> and to clear plant or animal tissue samples of color, and as such is useful for microscopy and ] 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.<ref>{{cite book |last1=Altman |first1=J. S. |last2=Tyrer |first2=N. M. | year = 1980 | chapter = Filling selected neurons with cobalt through cut axons | title = Neuroanatomical Techniques | pages = 373–402 |editor1=Strausfeld |editor1-first=N. J. |editor2=Miller |editor2-first=T. A. | publisher = Springer-Verlag}}</ref> It has also been discovered that methyl salicylate works as a ] that attracts some insects, such as the ]. Unlike some other kairomone's, Methyl Salicylate attracts all stages of the spotted lanternflies life. <ref>{{Cite journal|last1=Cooperband|first1=Miriam F.|last2=Wickham|first2=Jacob|last3=Cleary|first3=Kaitlin|last4=Spichiger|first4=Sven-Erik|last5=Zhang|first5=Longwa|last6=Baker|first6=John|last7=Canlas|first7=Isaiah|last8=Derstine|first8=Nathan|last9=Carrillo|first9=Daniel|date=2019-03-21|title=Discovery of three kairomones in relation to trap and lure development for spotted lanternfly (Hemiptera: Fulgoridae)|journal=Journal of Economic Entomology|language=en|volume=112|issue=2|pages=671–682|doi=10.1093/jee/toy412|pmid=30753676|issn=0022-0493|doi-access=free}}</ref>
	Methyl salicylate 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|date=September 2007}}
			Additional applications include: used as a simulant or surrogate for the research of chemical warfare agent ], due to its similar chemical and physical properties,<ref>{{cite journal |first1=S. L. |last1=Bartlet-Hunt |title=A Review of Chemical Warfare Agent Simulants for the Study of Environmental Behaviour |journal=Critical Reviews in Environmental Science and Technology |year=2008 |volume=38 |issue=2 |pages=112–136 |doi=10.1080/10643380701643650 |last2=Knappe |first2=D. R. U. |last3=Barlaz |first3=M. A. |s2cid=97484598 }}</ref> in restoring (at least temporarily) the elastomeric properties of old rubber rollers, especially in printers,<ref>{{cite web|url=http://www.mgchemicals.com/downloads/msds/english/sds-408a-l.pdf|title=MG Chemicals – Rubber Renue Safety Data Sheet|url-status=dead|archive-url=https://web.archive.org/web/20150626182545/http://www.mgchemicals.com/downloads/msds/english/sds-408a-l.pdf|archive-date=2015-06-26}}</ref> as a transfer agent in printmaking (to release toner from photocopied images and apply them to other surfaces),<ref>{{Cite web|last=Modrak|first=Rebekah and Bill Anthes|title=Image Transfer & Rubbing Techniques – Reframing Photography|url=https://www.reframingphotography.com/content/image-transfer-rubbing-techniques|access-date=2021-09-07|website=www.reframingphotography.com|language=en}}</ref> and as a penetrating oil to loosen rusted parts.
	Methyl salicylate, though its source plants are not true ], is used as a mint in some kinds of ] and ], as an alternative to the more common ] and ] oils. It can also be found as a flavoring of ]. It is also a potentially entertaining source of ]; when mixed with sugar and dried, it gains the tendency to build up electrical charge when crushed or rubbed. This effect can be observed by crushing wintergreen ] candy in a dark room.<ref>{{cite journal |first=E. N. |last=Harvey |title=The luminescence of sugar wafers |journal=] |year=1939 |volume=90 |issue=2324 |pages=35–36 |doi=10.1126/science.90.2324.35 |pmid=17798129 |bibcode=1939Sci....90...35N }}</ref><ref>
	{{cite news
	| url = http://home.howstuffworks.com/question505.htm
	| title = Why do Wint-O-Green Life Savers spark in the dark?
	| last =
	| first =
	| date =
	| publisher = ]
	| pages =
	| accessdate =
	| quote =
	}}</ref>
	Methyl salicylate can be used as a transfer agent, to produce a manual copy of an image on a surface.<ref> at Making-greeting-cards.com</ref>
	Methyl salicylate is added in small amounts to ] to lower its freezing point for transport in cold countries.
	Methyl salicylate is used as a simulant or surrogate for the research of chemical warfare agent ], due to its similar chemical and physical properties.<ref>{{cite journal |first=S. L. |last=Bartlet-Hunt |last2=''et al.'' |title=A Review of Chemical Warfare Agent Simulants for the Study of Environmental Behaviour |journal=Critical Reviews in Environmental Science and Technology |year=2008 |volume=38 |issue=2 |pages=112–136 |doi=10.1080/10643380701643650 |pmid= }}</ref>
	Methyl salicylate is one of several antiseptic ingredients in ] mouthwash produced by the ] company. It is also used in the "Dencorub Extra Strength" heat cream, which is used to treat joint and muscular pain and is a product of the Dencorub company.
	==Safety and toxicity==		==Safety and toxicity==
	In pure form, methyl salicylate is toxic, especially when taken internally. A single teaspoon (5ml) of methyl salicylate contains 7g of salicylate,<ref></ref> which is equivalent to more than twenty-three 300&nbsp;mg ] tablets. The lowest published lethal dose is 101&nbsp;mg/kg body weight in adult humans,<ref>, Physical & Theoretical Chemistry Laboratory, Oxford University</ref> (or 7.07&nbsp;grams for a 70-kg adult). It has proven fatal to small children in doses as small as 4 ml.<ref name="Wintergreen"/> A seventeen-year-old ] at ] on ], died in April 2007, after her body absorbed methyl salicylate through excessive use of topical muscle-pain relief products.<ref>{{cite news |title=Muscle-Pain Reliever Is Blamed For Staten Island Runner’s Death |url=http://www.nytimes.com/2007/06/10/nyregion/10cream.html?_r=1&ref=nyregion&oref=slogin | publisher=] |date=10 June 2007}}</ref>		Methyl salicylate is potentially deadly, especially for young children who may accidentally ingest preparations containing methyl salicylate, such as an ] solution. A single teaspoon (5&nbsp;mL) of methyl salicylate contains approximately 6&nbsp;g of salicylate,<ref>{{cite web|url = http://patient.info/doctor/salicylate-poisoning|title = Salicylate Poisoning – Patient UK|publisher = Patient.info|date = 2011-04-20|access-date = 2013-07-01|archive-date = 2015-08-18|archive-url = https://web.archive.org/web/20150818165207/http://patient.info/doctor/salicylate-poisoning|url-status = live}}</ref> which is equivalent to almost twenty 300&nbsp;mg ] tablets (5{{nbsp}}mL × 1.174{{nbsp}}g/mL = 5.87{{nbsp}}g). Toxic ingestions of salicylates typically occur with doses of approximately 150&nbsp;mg/kg body weight. This can be achieved with 1 mL of oil of wintergreen, which equates to 140{{nbsp}}mg/kg of salicylates for a 10{{nbsp}}kg child (22{{nbsp}}lbs).<ref>{{cite book |first=R. |last=Hoffman |title=Goldfrank's Toxicologic Emergencies |edition=10th |publisher=McGraw-Hill |location=New York, NY |year=2015 |pages=915–922 |isbn=978-0-07-180184-3 }}</ref> The lowest published lethal dose is 101&nbsp;mg/kg body weight in adult humans,<ref>{{Cite web |date=2010-09-15 |archive-date=2011-06-07 |title=Safety (MSDS) data for methyl salicylate |url=http://msds.chem.ox.ac.uk/ME/methyl_salicylate.html |url-status=dead |archive-url=https://web.archive.org/web/20110607225158/http://msds.chem.ox.ac.uk/ME/methyl_salicylate.html |access-date=2023-04-24 |website=University of Oxford Department of Chemistry MSDS}}</ref><ref>{{Cite web |date=June 1999 |title=Methyl Salicyclate |url=https://cameochemicals.noaa.gov/chris/MES.pdf |url-status=live |archive-url=https://web.archive.org/web/20161229181651/https://cameochemicals.noaa.gov/chris/MES.pdf |archive-date=29 Dec 2016 |access-date=24 Apr 2023 |website=CAMEO Chemicals}}</ref> (or 7.07&nbsp;grams for a 70&nbsp;kg adult). It has proven fatal to small children in doses as small as 4&nbsp;mL.<ref name="Wintergreen"/> A seventeen-year-old ] at ] on ] died in April 2007 after her body absorbed methyl salicylate through excessive use of topical muscle-pain relief products (using multiple patches against the manufacturer's instructions).<ref>{{cite news |title=Muscle-Pain Reliever Is Blamed For Staten Island Runner's Death |url=https://www.nytimes.com/2007/06/10/nyregion/10cream.html?_r=1&ref=nyregion&oref=slogin |work=New York Times |date=10 June 2007 |access-date=22 February 2017 |archive-date=18 January 2018 |archive-url=https://web.archive.org/web/20180118011031/http://www.nytimes.com/2007/06/10/nyregion/10cream.html?_r=1&ref=nyregion&oref=slogin |url-status=live }}</ref>
	Most instances of human toxicity due to methyl salicylate are a result of over-application of topical analgesics, especially involving children. Some people have intentionally ingested large amounts of oil of wintergreen. Salicylate, the major metabolite of methyl salicylate, may be quantitated in blood, plasma or serum to confirm a diagnosis of poisoning in hospitalized patients or to assist in an ].<ref>{{cite book |first=R. |last=Baselt |title=Disposition of Toxic Drugs and Chemicals in Man |edition=8th |publisher=Biomedical Publications |location=Foster City, CA |year=2008 |pages=1012–1014 |isbn=9780962652370 }}</ref>		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 ], ] or ] which may help professionals to confirm a diagnosis of poisoning in hospitalized patients or to assist in an ].<ref>{{cite book |first=R. |last=Baselt |title=Disposition of Toxic Drugs and Chemicals in Man |edition=8th |publisher=Biomedical Publications |location=Foster City, CA |year=2008 |pages=1012–1014 |isbn=978-0-9626523-7-0 }}</ref>
	==Compendial status==		==Compendial status==
	*]<ref name=ib29>{{cite web		* ]<ref name=ib29>{{cite web
	| last = The British Pharmacopoeia Secretariat		|last=The British Pharmacopoeia Secretariat
			|title=Index, BP 2009
	| first =
			|year=2009
	| authorlink =
			|url=http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf
	| coauthors =
			|access-date=5 July 2009
	| title = Index, BP 2009
			|url-status=dead
	| work =
			|archive-url=https://web.archive.org/web/20090411071437/http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf
	| publisher =
			|archive-date=11 April 2009
	| year = 2009
			}}</ref>
	| url = http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf
			* ]<ref>{{cite web |url=http://moldb.nihs.go.jp/jp/DetailList_en.aspx?submit=Detail(en)&keyword=Methyl+Salicylate |title=NIHS Japan |publisher=Moldb.nihs.go.jp |access-date=2013-07-01 |archive-date=2013-02-17 |archive-url=https://web.archive.org/web/20130217223243/http://moldb.nihs.go.jp/jp/DetailList_en.aspx?submit=Detail(en)&keyword=Methyl+Salicylate |url-status=live }}</ref>
	| format =
	| doi =
	| accessdate = 5 July 2009
	}}</ref>
	*]<ref></ref>
	==See also==		==See also==
			* ] <!--An alternative salicylate in analgesic creams.-->
	*]
	*]
	*]
	==References==		==References==
			{{reflist|30em}}
	<references/>
	==External links==		==External links==
			{{Commons category|Methyl salicylate}}
	;Toxicity:
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	{{Anti-inflammatory and antirheumatic products}}		{{Anti-inflammatory and antirheumatic products}}
	{{NSAIDs}}
	{{Salicylates}}		{{Salicylates}}
			{{Prostanoid signaling modulators}}
			{{Transient receptor potential channel modulators}}
	{{DEFAULTSORT:Methyl Salicylate}}		{{DEFAULTSORT:Methyl Salicylate}}
			]
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