Methyl salicylate

Methyl salicylate

Names
IUPAC name Methyl 2-hydroxybenzoate
Other names Salicylic acid methyl ester; Oil of wintergreen; Betula oil; Methyl 2-hydroxybenzoate
Identifiers
CAS Number	119-36-8 Y
3D model (Jmol)	Interactive image
ChemSpider	13848808 Y
ECHA InfoCard	100.003.925
IUPHAR/BPS	2431
KEGG	D01087 Y
UNII	LAV5U5022Y Y
InChI InChI=1S/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3 Y Key: OSWPMRLSEDHDFF-UHFFFAOYSA-N Y InChI=1/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3 Key: OSWPMRLSEDHDFF-UHFFFAOYAD
SMILES O=C(OC)c1ccccc1O
Properties
Chemical formula	C8H8O3
Molar mass	152.15 g·mol−1
Density	1.174 g/cm3
Melting point	−8.6 °C (16.5 °F; 264.5 K)
Boiling point	222 °C (432 °F; 495 K) decomposes at 340-350 °C
Solubility in water	0.639 g/L (21 °C) 0.697 g/L (30°C)
Solubility	miscible in diethyl ether, ethanol
Solubility in acetone	10.1 g/g (30 °C)
Vapor pressure	1 mmHg (54 °C)
Acidity (pKa)	9.8
Magnetic susceptibility (χ)	-86.30·10−6 cm3/mol
Refractive index (nD)	1.538
Hazards
Main hazards	Harmful
GHS pictograms
GHS signal word	Warning
GHS hazard statements	H302
EU classification (DSD)	Xn
R-phrases	R22
NFPA 704	1 2 0
Flash point	96 °C (205 °F; 369 K)
Autoignition temperature	452.7 °C (846.9 °F; 725.8 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Methyl salicylate (oil of wintergreen or wintergreen oil) is an organic ester naturally produced by many species of plants, particularly wintergreens. It is also synthetically produced, used as a fragrance, in foods and beverages, and in liniments.

The compound 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.

This compound is probably produced as an anti-herbivore defense. If the plant is infected with herbivorous insects, the release of methyl salicylate may function as an aid in the recruitment of beneficial insects to kill the herbivorous insects. 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.

Numerous plants produce methyl salicylate in very small amounts. Some plants, such as the following, produce more:

Methyl salicylate can be produced by esterifying salicylic acid with methanol. 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).

In pure form, methyl salicylate is harmful, when taken orally. A single teaspoon (5 ml) of methyl salicylate contains approximately 6 g of salicylate, which is equivalent to almost twenty 300 mg aspirin tablets (5 mL * 1.174 g/mL = 5.87 g). The lowest published lethal dose is 101 mg/kg body weight in adult humans, (or 7.07 grams for a 70-kg adult). It has proven fatal to small children in doses as small as 4 ml. A seventeen-year-old 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.