Methyl salicilate

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
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: some species of the genus Gaultheria in the family Ericaceae, including Gaultheria procumbens, the wintergreen or eastern teaberry; some species of the genus Betula in the family Betulaceae, particularly those in the subgenus 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.