M6752

Methyl salicylate

ReagentPlus^®, ≥99% (GC)

• 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
• UNSPSC Code: 12191503
• NACRES: NA.25
• PubChem Substance ID: 24897111
• EC Number: 204-317-7
• Beilstein/REAXYS Number: 971516
• MDL number: MFCD00002214

Properties

• vapor density: 5.26 (vs air)
• Quality Segment: 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

Description

General description

Methyl salicylate (MeSA) is a natural herbivore-induced plant volatile[1] It is a naturally occurring product in trees, legumes, exotic plants, vegetables, berries, and the primary constituent of the oil of wintergreen.[2] 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[3]
• as a plant elicitor to test its effect on reducing the whitefly population from tomato plants[4]
• 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.[1] 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.[2] It has counter irritant and anti-inflammatory effects.

Legal Information

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

Safety Information

• pictograms: GHS08,GHS05,GHS07
• signalword: Danger
• hcodes: H302,H317,H318,H361d,H412
• pcodes: P273 - P280 - P301 + P312 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Repr. 2 - Skin Sens. 1B
• Storage Class: 10 - Combustible liquids
• flash_point_f: 204.8 °F - closed cup
• flash_point_c: 96 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter