Methyl Salicylate

Base Information

• Chemical Name: Methyl Salicylate
• CAS No.: 119-36-8
• Deprecated CAS: 8022-86-4,8024-54-2,648434-07-5,8024-54-2
• Molecular Formula: C8H8O3
• Molecular Weight: 152.15
• Hs Code.: H4(HO)COOCH3 MOL WT. 152.15
• European Community (EC) Number: 204-317-7,686-116-8
• NSC Number: 8204
• UNII: LAV5U5022Y
• DSSTox Substance ID: DTXSID5025659
• Nikkaji Number: J1.161.435C,J3.013.287D,J2.915G
• Wikipedia: Methyl_salicylate
• Wikidata: Q407669
• NCI Thesaurus Code: C80564
• RXCUI: 29787
• Metabolomics Workbench ID: 46398
• ChEMBL ID: CHEMBL108545
• Mol file: 119-36-8.mol

Synonyms:Hewedolor;Linsal;methyl salicylate;methyl salicylate sodium salt;methylsalicylate;Metsal Liniment;Rheumabal

Chemical Property of Methyl Salicylate

Chemical Property:

• Appearance/Colour: colourless liquid with an odour of wintergreen
• Vapor Pressure: 1 mm Hg ( 54 °C)
• Melting Point: -8 °C
• Refractive Index: 1.535 - 1.538
• Boiling Point: 222 °C at 760 mmHg
• PKA: pKa 9.90 (Uncertain)
• Flash Point: 86.8 °C
• PSA: 46.53000
• Density: 1.209 g/cm³
• LogP: 1.17880
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Very slightly soluble in water, miscible with ethanol (96 per cent) and with fatty and essential oils.
• Water Solubility.: 0.07 g/100 mL (20 ºC)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 152.047344113
• Heavy Atom Count: 11
• Complexity: 144

Purity/Quality:

99.5%, ^*data from raw suppliers

Gaultherin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/38-36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Sunscreens
• Canonical SMILES: COC(=O)C1=CC=CC=C1O
• Chemical Properties and Occurrence: Methyl salicylate (MeSA) is the methyl ester form of Salicylic acid (SA), characterized by a colorless appearance, sweet odor, low molecular weight (152.149 g/mol), and high boiling point (223 掳C).; Also known as the oil of wintergreen, it is the major component of wintergreen oil and is traditionally isolated from wintergreen plants.
• Biological Role and Uses: Methyl salicylate (MeSA) plays a crucial role as a volatile organic compound (VOC) and is involved in various plant interactions, such as plant-herbivore, plant-predator, plant-pollinator, and plant-plant interactions. It acts as a signal molecule and induces defense mechanisms under different stress conditions in plants. In healthy plant tissues, MeSA stimulates systemic acquired resistance (SAR) responses, triggering salicylic acid production and priming plant defenses against herbivorous attacks.; Widely emitted by plants, MeSA attracts natural enemies of herbivores and serves as a repellent towards certain herbivores. It functions as a common floral scent, attracting pollinating insects and contributing to the reproductive cycle in flowering plants.; Methyl salicylate (MeSA) also exhibits allelopathic effects, interfering with the growth processes of neighboring plants and favoring the emitter in soil nutrient competition.
• Commercial and Regulatory Considerations: Methyl salicylate (MeSA) is found in various over-the-counter products such as creams, ointments, lotions, liniments, and medicated oils, primarily used for topical application to relieve musculoskeletal aches and pains.; Oil of wintergreen, containing approximately 98% methyl salicylate, is a highly potent liquid, with 1 mL equivalent to 1400 mg of aspirin.; Due to its potential for serious toxicity, products containing more than 5% methyl salicylate are regulated by the FDA, with warnings against misuse and keeping them out of reach of children.

Technology Process of Methyl Salicylate

There total 155 articles about Methyl Salicylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

Methyl 2-<(3,4-Dimethoxyphenyl)methoxy>benzoate (73119-94-5) → veratryl acetate (53751-40-9) + methyl salicylate (119-36-8,8024-54-2)

Guidance literature:

With acetic acid; at 90 ℃; for 4h;

DOI:10.1080/00397919408011711

Reference yield: 67.0%

2-methoxybenzoic acid methyl ester (606-45-1) → salicylic acid (69-72-7,25496-36-0,8052-31-1) + methyl salicylate (119-36-8,8024-54-2)

Guidance literature:

With iodine; aluminium; In cyclohexane; at 45 ℃; for 1h; Solvent; Temperature;

DOI:10.1016/j.tetlet.2018.03.010

Reference yield: 65.0%

benzoic acid methyl ester (93-58-3,5705-52-2,80226-58-0) → methyl 2-oxepinecarboxylate (67490-10-2) + benzyl alcohol (100-51-6,185532-71-2) + methyl salicylate (119-36-8,8024-54-2)

Guidance literature:

With Phellinus ribis Karst var. ribis (NCWRF-FPRL 42); at 20 ℃;

DOI:10.1039/b718375e

upstream raw materials:

diazomethane

diethyl ether

salicylic acid

methanol

Downstream raw materials:

2-nicotinoyloxy-benzoic acid methyl ester

methyl acetylsalicylate

benzoic acid phenyl ester

2-amino-3-phenyl-4H-chromen-4-one

Refernces

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• 5、 Cortez-Maya, Sandra,Pedro-Hernández, Luis Daniel,Martínez-Klimova, Elena,Ramírez-ápan, Teresa,Martínez-García, Marcos. "Anticancer activity ofwater-soluble olsalazine-pamam-dendrimer-salicylic acid-conjugates". . . Retrieved 2019.
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• 10、 Lynch, Will E.,Nivens, Delana,Quillian, Brandon,Padgett, Clifford W.,Petrillo, Anthony,Peek, Nathan,Stone, John. "A Copper(II) tris-imidazolylphosphine complex as a functional model of flavonol 2,4-dioxygenase". . p. 99 - 106. Retrieved 2019.