Methyl Salicylate

Methyl Salicylate

Cat Number
API119368
CAS Number
119-36-8

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CAS Number
119-36-8
EINECS
204-317-7
Storage
Store at room temperature
Synonyms
Analgit; Flucarmit; Exagien; Betula; 2-Hydroxybenzoic acid methyl ester; Gaultheriaoel
Molecular Formula
C8H8O3
Molecular Weight
152.15
Smiles
COC(=O)C1=CC=CC=C1O
Appearance
Clear liquid
Melting Point
19.4℃
Boiling Point
237.2℃
Relative Density
0.974
General Description
Methyl salicylate is a natural methyl ester of salicylic acid found in wintergreen oil and other plants, used extensively as a topical analgesic and anti-inflammatory agent. It is a common active ingredient in over-the-counter rubefacient preparations, liniments, and muscle rubs. The compound is readily absorbed through intact skin and exerts its effects locally, though systemic absorption can occur with excessive application.
Mechanism of Action
Methyl salicylate is hydrolyzed by esterases in the skin to salicylic acid, which then reversibly inhibits cyclooxygenase (COX) enzymes, reducing the synthesis of prostaglandins responsible for pain and inflammation. The rubefacient effect—local vasodilation and erythema—produces a sensation of warmth that is thought to contribute to pain relief through counterirritation and stimulation of cutaneous thermoreceptors. This dual mechanism provides symptomatic relief of musculoskeletal discomfort.
Application
It is indicated for the temporary relief of minor aches and pains associated with muscle strains, sprains, arthritis, and backache when applied topically. It is a common ingredient in sports creams, patches, and liniments. Overuse or application under occlusive dressings can lead to salicylate toxicity, particularly in children, and concurrent use with oral anticoagulants may increase bleeding risk. Patients should avoid applying to broken or irritated skin.

Using two‑electrode voltage clamp in frog oocytes expressing GABAA, NMDA, and Nav1.2 channels, the authors showed that L‑carvone and methyl salicylate concentration‑dependently modulated all three targets. Methyl salicylate inhibited GABAA receptors at low concentrations but potentiated them at high concentrations. When formulated in lipid emulsion and given intravenously to rats, both compounds induced general anesthesia at plasma concentrations of 7.9 mM (L‑carvone) and 2.7 mM (methyl salicylate). At these concentrations, NMDA receptors were inhibited ≥53%, Nav1.2 channels ≥78%, and GABAA receptors were potentiated 30% by methyl salicylate. The data support that these mint extracts produce anesthesia through allosteric modulation of canonical anesthetic targets.

Fig. 1 Linear-log plot of the percent current change from baseline of GABAA receptors exposed to L-carvone. (Brosnan RJ, <i>et al</i>., 2022) Fig. 1 Linear-log plot of the percent current change from baseline of GABAA receptors exposed to L-carvone. (Brosnan RJ, et al., 2022)

References

  1. Brosnan RJ, et al. Anesthetic Pharmacology of the Mint Extracts L-Carvone and Methyl Salicylate. Pharmacology. 2022; 107(3-4):167-178.

Microcapsules of gelatin and gum Arabic containing methyl salicylate were prepared by coacervation and applied to 100% cotton and 100% polyamide fabrics. The microcapsules had well‑defined geometry and improved thermal stability of the active ingredient. Release followed the Korsmeyer‑Peppas model with a Fickian mechanism. Higher washing temperature (50°C) caused more pronounced release than 37°C. The textile matrix influenced release kinetics and microcapsule durability. These findings guide the design of functional textiles with controlled release of fragrances or active compounds.

Fig. 2 Micrograph of methyl salicylate microcapsules. (Mendes S, <i>et al</i>., 2021) Fig. 2 Micrograph of methyl salicylate microcapsules. (Mendes S, et al., 2021)

References

  1. Mendes S, et al. Vehiculation of Methyl Salicylate from Microcapsules Supported on Textile Matrix. Materials (Basel). 2021; 14(5):1087.

Does Methyl Salicylate require protection from light during long-term storage?

Yes, it is photosensitive and may discolor upon prolonged light exposure. Store in light-resistant, tightly sealed containers, preferably amber glass.

What is the recommended storage temperature for Methyl Salicylate?

Store at controlled room temperature (15-25°C). Avoid excessive heat, as it is volatile and can evaporate. Keep away from open flames or ignition sources.

Is Methyl Salicylate stable in topical cream and gel formulations?

Yes, it is stable in common topical bases. However, it can hydrolyze to salicylic acid under alkaline conditions. We provide compatibility data for various pH ranges.

How is the impurity salicylic acid monitored during storage?

This primary hydrolysis product is quantified using a validated HPLC method, ensuring it remains below pharmacopoeial limits for topical pharmaceutical use.
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