Methyl salicylate

Source: Wikipedia, the free encyclopedia.
Methyl salicylate
Skeletal formula
Ball-and-stick model
Space-filling model
Sample of a clear liquid
Names
Preferred IUPAC name
Methyl 2-hydroxybenzoate
Other names
  • Salicylic acid methyl ester
  • Oil of wintergreen
  • Betula oil
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.003.925 Edit this at Wikidata
EC Number
  • 204-317-7
IUPHAR/BPS
KEGG
RTECS number
  • VO4725000
UNII
  • InChI=1S/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3 checkY
    Key: OSWPMRLSEDHDFF-UHFFFAOYSA-N checkY
  • InChI=1/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3
    Key: OSWPMRLSEDHDFF-UHFFFAOYAD
  • O=C(OC)c1ccccc1O
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
1.538
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Harmful
GHS labelling:
GHS07: Exclamation mark[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)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
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).
checkY verify (what is checkY☒N ?)

Methyl salicylate (oil of wintergreen or wintergreen oil) is an

fragrance
and as a flavoring agent.

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

methylase enzyme.[8]

Methyl salicylate as a plant metabolite

Wintergreen plants (Gaultheria procumbens)

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

Betulenta such as B. lenta, the black birch; all species of the genus Spiraea in the family Rosaceae, also called the meadowsweets; species of the genus Polygala in the family Polygalaceae. Methyl salicylate can also be a component of floral scents, especially in plants dependent on nocturnal pollinators like moths,[11] scarab beetles, and (nocturnal) bees.[12]

Commercial production

Methyl salicylate can be produced by

esterifying salicylic acid with methanol.[13] Commercial methyl salicylate is now synthesized, but in the past, it was commonly distilled from the twigs of Betula lenta (sweet birch) and Gaultheria procumbens
(eastern teaberry or wintergreen).

Uses

Chick embryo that was treated with methylene blue to stain the skeleton, then cleansed with two or three ethanol washes, and treated with methyl salicylate to make the surrounding tissues transparent

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

orchid bees for study, which apparently gather the chemical to synthesize pheromones,[21] and 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.[22] It has also been discovered that methyl salicylate works as a kairomone that attracts some insects, such as the spotted lanternfly.[23]

Additional applications include: used as a simulant or surrogate for the research of chemical warfare agent

sulfur mustard, due to its similar chemical and physical properties,[24] in restoring (at least temporarily) the elastomeric properties of old rubber rollers, especially in printers,[25] as a transfer agent in printmaking (to release toner from photocopied images and apply them to other surfaces),[26]
and as a penetrating oil to loosen rusted parts.

Safety and toxicity

Methyl salicylate is potentially deadly, especially for young children who may accidentally ingest preparations containing methyl salicylate such as an

cross-country runner at Notre Dame Academy on Staten Island 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).[31]

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

serum which may help professionals to confirm a diagnosis of poisoning in hospitalized patients or to assist in an autopsy.[32]

Compendial status

See also

References

  1. ^ a b c "Methyl salicylate". chemister.ru. Archived from the original on 2014-05-24. Retrieved 2014-05-23.
  2. ^ a b c d e f Sigma-Aldrich Co., Methyl salicylate.
  3. .
  4. ^ .
  5. ^ "The Good Scents Company - Aromatic/Hydrocarbon/Inorganic Ingredients Catalog information". Archived from the original on 2019-12-06. Retrieved 2019-12-03.
  6. ^ 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.
  7. ^ 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.
  8. PMID 20035037
    .
  9. .
  10. .
  11. .
  12. .
  13. .
  14. ^ "Topical analgesics introduction". Medicine.ox.ac.uk. 2003-05-26. Archived from the original on 2012-08-04. Retrieved 2012-11-07.
  15. PMID 15033879
    .
  16. .
  17. ^ a b Wintergreen Archived 2018-03-19 at the Wayback Machine at Drugs.com
  18. PMID 17798129
    .
  19. ^ "Why do Wint-O-Green Life Savers spark in the dark?". HowStuffWorks. Archived from the original on 2007-08-17. Retrieved 2008-04-27.
  20. ^ Listerine. "Original Listerine Antiseptic Mouthwash". Archived from the original on 17 February 2015. Retrieved 25 March 2015.
  21. S2CID 2845587
    .
  22. ^ 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.
  23. PMID 30753676
    .
  24. .
  25. ^ "MG Chemicals – Rubber Renue Safety Data Sheet" (PDF). Archived from the original (PDF) on 2015-06-26.
  26. ^ Modrak, Rebekah and Bill Anthes. "Image Transfer & Rubbing Techniques – Reframing Photography". www.reframingphotography.com. Retrieved 2021-09-07.
  27. ^ "Salicylate Poisoning – Patient UK". Patient.info. 2011-04-20. Archived from the original on 2015-08-18. Retrieved 2013-07-01.
  28. .
  29. ^ "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.
  30. ^ "Methyl Salicyclate" (PDF). CAMEO Chemicals. June 1999. Archived (PDF) from the original on 29 Dec 2016. Retrieved 24 Apr 2023.
  31. ^ "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.
  32. .
  33. ^ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 5 July 2009.
  34. ^ "NIHS Japan". Moldb.nihs.go.jp. Archived from the original on 2013-02-17. Retrieved 2013-07-01.

External links