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M6752

Sigma-Aldrich

Methyl salicylate

ReagentPlus®, ≥99% (GC)

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Synonym(s):
2-Hydroxybenzoic acid methyl ester, Methyl 2-hydroxybenzoate, Oil of wintergreen, Wintergreen oil
Linear Formula:
2-(HO)C6H4CO2CH3
CAS Number:
119-36-8
Molecular Weight:
152.15
Beilstein:
971516
EC Number:
204-317-7
MDL number:
MFCD00002214
PubChem Substance ID:
24897111
NACRES:
NA.25

vapor density

5.26 (vs air)

Quality Level

200

vapor pressure

1 mmHg ( 54 °C)

product line

ReagentPlus®

Assay

≥99% (GC)

form

liquid

autoignition temp.

847 °F

refractive index

n20/D 1.536 (lit.)

bp

222 °C (lit.)

mp

−8-−7 °C (lit.)

density

1.174 g/mL at 25 °C (lit.)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

SMILES string

COC(=O)c1ccccc1O

InChI

1S/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3

InChI key

OSWPMRLSEDHDFF-UHFFFAOYSA-N

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General description

Methyl salicylate (MeSA) is a natural herbivore-induced plant volatile It is a naturally occurring product in trees, legumes, exotic plants, vegetables, berries, and the primary constituent of the oil of wintergreen. MeSA is produced from salicylic acid.

Application

Methyl salicylate has been used:
  • as a component of clarifying solution for treating Mongolian gerbil cochlea intact for immunofluorescence analysis
  • as a plant elicitor to test its effect on reducing the whitefly population from tomato plants
  • in the hyalinization of tissues for pulmonary angiography
  • in clearing tissues

Biochem/physiol Actions

Methyl salicylate plays an important role in fruit ripening. It is known to attract natural enemies of herbivores. MeSA inhibits the activity of aminocyclopropane-1-carboxylic acid synthase (ACC synthase) and aminocyclopropane-1-carboxylic acid oxidase (ACC oxidase) in plums and tomatoes, it can inhibit fungal infections and reduce chilling injury symptoms in fruits like pomegranates. This oil of wintergreen is of great interest in the tobacco industry as a flavorant. It has counter irritant and anti-inflammatory effects.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Repr. 2 - Skin Sens. 1B

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

204.8 °F - closed cup

Flash Point(C)

96 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Niall J A Conboy et al.
Journal of chemical ecology, 46(11-12), 1090-1104 (2020-10-28)
The glasshouse whitefly (Trialeurodes vaporariorum Westwood) is a polyphagous arthropod pest that is of particular detriment to glasshouse grown tomato (Solanum lycopersicum) across temperate regions of the world. Control of whiteflies with synthetic pesticides has resulted in the evolution of
Airborne signalling by methyl salicylate in plant pathogen resistance
Shulaev V, et al.
Nature, 385(6618), 718-718 (1997)
Aspirin and the Salicylates (2013)
Active Ingredients Used in Cosmetics: Safety Survey (2008)
Properties and physiological function of Ca2+-dependent K+ currents in uniglomerular olfactory projection neurons
Bradler C, et al.
Journal of Neurophysiology, 115(5), 2330-2340 (2016)
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