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Merck

M6752

Methyl salicylate

ReagentPlus®, ≥99% (GC)

Synonym(s):

2-Hydroxybenzoic acid methyl ester, Methyl 2-hydroxybenzoate, Oil of wintergreen, Wintergreen oil

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About This Item

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

Product Name

Methyl salicylate, ReagentPlus®, ≥99% (GC)

InChI key

OSWPMRLSEDHDFF-UHFFFAOYSA-N

InChI

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

SMILES string

COC(=O)c1ccccc1O

vapor density

5.26 (vs air)

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

Quality Level

200

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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.

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.

Legal Information

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

signalword

Danger

Hazard Classifications

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

Storage Class

10 - Combustible liquids

wgk

WGK 2

flash_point_f

204.8 °F - closed cup

flash_point_c

96 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ7599
MKCW9073
MKCV6603
MKCT1643
MKCQ5492

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Excitatory postrhinal projections to principal cells in the medial entorhinal cortex
Koganezawa N, et al.
The Journal of Neuroscience, 35(48), 15860-15874 (2015)
Therapeutic Medications in Athletic Training (2007)
A novel mouse model of high flow-induced pulmonary hypertension-surgically induced by right pulmonary artery ligation
Zhang A, et al.
The Journal of Surgical Research, 208, 132-139 (2017)
Airborne signalling by methyl salicylate in plant pathogen resistance
Shulaev V, et al.
Nature, 385(6618), 718-718 (1997)
Jordano Salamanca et al.
Insects, 10(12) (2019-11-30)
Methyl salicylate (MeSA) is an herbivore-induced plant volatile (HIPV) known to attract the natural enemies of herbivores in agro-ecosystems; however, whether this attraction leads to an increase in natural enemy functioning, i.e., predation, remains largely unknown. Here, we monitored for
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