Methyl salicylate
IUPAC name	Methyl salicylate
Identifiers
CAS number	[119-36-8]
SMILES	c1(O)ccccc1C(=O)OC
Properties
Molecular formula	C8H8O3
Molar mass	152. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 1494 g/mol
Density	1. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 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 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. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid The flash point of a flammable liquid is the lowest Temperature at which it can form an ignitable mixture in air In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Plants are living Organisms belonging to the kingdom Plantae. Some of the plants producing it are called wintergreens, hence the common name. Wintergreen is a group of plants Wintergreen once commonly referred to Plants that continue Photosynthesis (remain Green) throughout the Winter

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. Esters are a class of Chemical compounds and Functional groups Esters consist of an inorganic or organic Acid in which at least An organic acid is an Organic compound with Acidic properties In Chemistry, an alcohol is any Organic compound in which a Hydroxyl group ( - O[[hydrogen H]]) is bound to a Carbon Herbivory is a form of Predation in which an Organism, known as a herbivore, consumes principally Autotrophs ref name=Campbell>Campbell 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. Beneficial insects are any of a number of species of insects that perform valued services like Pollination and pest control ^[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. A pheromone (from Greek φέρω phero "to bear" + ‘ορμόνη " Hormone " is a Chemical that triggers a natural A pathogen (from Greek πάθος pathos "suffering passion" and γἰγνομαι (γεν- gignomai (gen- "I give birth to" infectious Tobacco mosaic virus (TMV is an RNA virus that infects Plants especially Tobacco and other members of the family Solanaceae. ^[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. Pyrolaceae was a small family of Flowering plants under the old Cronquist system of plant classification Pyrola ( syn Pirola Necker is a genus of evergreen Herbaceous Plants in the family Ericaceae.
• Some species of the genus Gaultheria in the family Ericaceae. Gaultheria is a genus of about 170-180 species of Shrubs in the family Ericaceae. The Plant family Ericaceae (also called the heath family or ericaceous plants) are mostly lime -hating ( Calcifuge)
• Some species of the genus Betula in the family Betulaceae, particularly those in the subgenus Betulenta. Birch is the name of any Tree of the genus Betula ( Bé-tu-la) in the family Betulaceae, closely related to the Betulaceae, or the Birch Family, includes six genera of Deciduous nut -bearing Trees and Shrubs including the Birches Subgenus Betulenta - Wintergreen oil birches Bark on twigs rich in Methyl salicylate (oil of wintergreen
• All species of the family Spiraea, also called the Meadowsweets. For the European and west Asian herb see Meadowsweet. Spiraea (Meadowsweet is a genus of about 80-100 species

Commercial production

Methyl salicylate can be produced by esterifying salicylic acid with methanol. Esterification is the general name for a Chemical reaction in which two reactants (typically an alcohol and an acid form an Ester as the reaction product Salicylic acid (from the Latin word for the willow tree Salix, from whose bark it can be obtained is a Beta hydroxy acid (BHA with the formula Methanol, also known as methyl alcohol, carbinol, wood alcohol, wood naphtha or wood spirits, is a Chemical compound 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). Betula lenta ( Sweet Birch, also known as Black Birch, Cherry Birch, Mahogany Birch, or Spice Birch) is a species of Gaultheria procumbens ( Eastern Teaberry, Checkerberry, Boxberry or American Wintergreen) is a species of Gaultheria

Uses

Chick embryo that was treated with Methylene blue to stain the skeleton, then cleansed with 2 or 3 ethanol washes, and treated with Methyl salicylate to make the surrounding tissues transparent. The chicken ( Gallus gallus, sometimes G gallus domesticus) is a domesticated Fowl which is traditionally believed to have descended from An embryo (from Greek:, plural, lit "that which grows" from en- "in" + bryein "to swell be full" is a multicellular Methylene blue is a heterocyclic aromatic Chemical compound with Molecular formula: C 16 H 18 Cl[[nitrogen Tissue is a cellular organizational level intermediate between cells and a complete organism

It is used as a rubefacient in deep heating liniments, and in small amounts as a flavoring agent at no more than 0. A rubefacient is a substance for External application that produces redness of the Skin e Liniment, (or embrocation from the Latin linere, to Anoint, is a medicated topical preparation for application to the skin Alternate meanings Seasoning (cast iron; Seasoning (wood; Seasoning (slave Seasoning is the process of imparting or improving 04%. ^[3] It is also used to provide fragrance to various products and as an odor masking agent for some organophosphate pesticides. Perfume is a mixture of fragrant Essential oils and Aroma compounds Fixatives and Solvents used to give the human body animals objects and living An organophosphate (sometimes abbreviated OP) is the general name for Esters of Phosphoric acid. A pesticide is a substance or mixture of substances used to kill a pest. If applied in too high quantities it can cause stomach and kidney problems.

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. Euglossine bees, also called orchid bees, are the only group of corbiculate bees whose non-parasitic members do not all possess eusocial behavior. ^[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.

Methyl salicylate is used in some kinds of chewing gum and candy, as an alternative to the more common peppermint and spearmint oils. For songs called "Chewing Gum" see Chewing Gum (song Chewing gum is a type of Confectionery traditionally made of Chicle This article is about the Candy. See Mint (disambiguation for other meanings Peppermint ( Mentha × piperita) is a hybrid mint, a cross between Watermint ( Mentha aquatica) and Spearmint 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. Triboluminescence is an Optical phenomenon in which Light is generated via the breaking of asymmetrical bonds in a Crystal when that material is scratched This effect can be observed by crushing wintergreen Life Savers candy in a dark room. Life Savers is an American brand of ring-shaped mints and artificially fruit-flavored hard candy. ^[5][6]

Methyl salicylate can also be used as a transfer agent, to produce a manual copy of an image on a surface. ^[7]

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. ^[8] It has proven fatal to small children in doses as small as 4 mL. ^[9] 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. Cross Country running is a Sport of running Compete to complete a course over open or rough terrain faster than other teams Staten Island (ˌstætənˈaɪlənd is a borough of New York City situated primarily on the island of the same name ^[10]

See also

• Salicylic acid
• Wintergreen

References

1. ^ D. Salicylic acid (from the Latin word for the willow tree Salix, from whose bark it can be obtained is a Beta hydroxy acid (BHA with the formula Wintergreen is a group of plants Wintergreen once commonly referred to Plants that continue Photosynthesis (remain Green) throughout the Winter 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. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 15537163.  
2. ^ Vladimir Shulaev, Paul Silverman, Ilya Raskin (20 Feb 1997). "Airborne signalling by methyl salicylate in plant pathogen resistance". Nature 385: 718 - 721. Nature is a prominent Scientific journal, first published on 4 November 1869 doi:10.1038/385718a0. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.  
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. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.  
5. ^ E. N. Harvey, "The luminescence of sugar wafers," Science magazine, 14 July 1939: Vol. 90. no. 2324, pp. 35–36.
6. ^ "Why do Wint-O-Green Life Savers spark in the dark?", HowStuffWorks.  
7. ^ Image Transfer at Making-greeting-cards. com
8. ^ Safety data for methyl salicylate, Physical & Theoretical Chemistry Laboratory, Oxford University
9. ^ Wintergreen at Drugs. com
10. ^ "Muscle-Pain Reliever Is Blamed For Staten Island Runner’s Death", New York Times, 2007-06-10. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 1190 - Third Crusade: Frederick I Barbarossa drowns in the Sally River while leading an army to Jerusalem Retrieved on 2007-06-09. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 53 - Roman Emperor Nero marries Claudia Octavia 62 - Claudia Octavia commits  

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