Ethyl salicylate
[CAS# 118-61-6]

Identification

• Classification: API >> Synthetic anti-infective drugs >> Disinfectant antiseptic
• Name: Ethyl salicylate
• Synonyms: Ethyl 2-hydroxybenzoate
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.18
• CAS Registry Number: 118-61-6
• EC Number: 204-265-5
• FEMA: 2458
• SMILES: CCOC(=O)C1=CC=CC=C1O

Properties

• Density: 1.128 g/mL
• Melting point: 2-3 °C
• Boiling point: 234 °C
• Refractive index: 1.521-1.525
• Flash point: 107 °C
• Water solubility: slightly soluble

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

Ethyl salicylate is an organic ester formed from the esterification of salicylic acid and ethanol. It is a clear, colorless to pale yellow liquid with a characteristic sweet, wintergreen-like odor. This compound is naturally present in several plants, notably in the essential oil of wintergreen (Gaultheria procumbens) and some other species where it contributes to their aroma. It has been known to science and industry for over a century and has found various uses based on its fragrance, mild antiseptic properties, and chemical reactivity.

The discovery and early recognition of ethyl salicylate's fragrance properties can be traced back to the broader study of salicylic acid derivatives in the 19th century. As interest in aromatic compounds and essential oils grew in perfumery and medicinal chemistry, researchers identified ethyl salicylate as one of the pleasant-smelling esters derived from salicylic acid. It was characterized by its relatively low volatility and persistent odor, which made it particularly suitable for use in perfumery.

Ethyl salicylate is produced via a Fischer esterification process, in which salicylic acid reacts with ethanol in the presence of an acid catalyst such as sulfuric acid. The reaction proceeds with the elimination of water, and the product is typically purified through distillation. This synthetic method is straightforward and efficient, making the compound readily available for commercial and industrial applications.

One of the primary uses of ethyl salicylate is in the flavor and fragrance industry. Due to its strong, sweet, and slightly minty aroma, it is employed as a flavoring agent in candies, chewing gums, toothpaste, and pharmaceuticals. It serves as a fragrance component in perfumes and colognes, particularly in formulations intended to emulate natural or herbal scents. Its olfactory characteristics are valued for evoking a sense of freshness and cleanliness.

In pharmaceuticals, ethyl salicylate has been used in topical preparations where its mild anti-inflammatory and analgesic properties can offer relief for minor muscle or joint pain. These properties stem from its relationship to salicylic acid, a known anti-inflammatory agent. However, its use in this context has declined in favor of more potent and better-studied non-steroidal anti-inflammatory drugs (NSAIDs).

Ethyl salicylate also functions as an intermediate in organic synthesis. Its reactive ester group and aromatic hydroxyl moiety make it a useful starting material in the preparation of more complex molecules. It can be involved in hydrolysis, transesterification, and other transformations that exploit its ester functionality. In laboratory settings, it may also serve as a model compound for studying ester hydrolysis or for demonstrating organic reactions in educational contexts.

Although generally considered to be of low toxicity, ethyl salicylate should be handled with care, particularly in industrial settings where prolonged exposure to vapors can occur. As with other salicylate esters, ingestion in significant quantities can lead to salicylate toxicity, with symptoms such as nausea, dizziness, and metabolic disturbances. Appropriate personal protective equipment and ventilation are standard measures in environments where the substance is handled in bulk.

Ethyl salicylate is a stable compound under normal storage conditions and is compatible with a wide range of cosmetic, flavor, and fragrance formulations. It blends well with essential oils and other aromatic esters, which enhances its versatility in product design.

Today, ethyl salicylate continues to be used in industries that require safe, effective, and pleasant-smelling compounds. Its synthesis, properties, and safety profile are well documented in the literature, ensuring that its applications are based on established chemical principles and industrial standards.

References

2021. Characterization of odor-active volatile compounds of jambolan [Syzgium cumini (L.) Skeels] wine. Journal of Food Science and Technology, 59(3).
DOI: 10.1007/s13197-021-05163-9

2023. Antibacterial, antifungal activities and toxicity of new synthetic fatty acid salicylate esters. Medicinal Chemistry Research, 32(4).
DOI: 10.1007/s00044-023-03034-w

2024. Volatile metabolomics and metagenomics reveal the effects of lactic acid bacteria on alfalfa silage quality, microbial communities, and volatile organic compounds. Communications Biology, 7(1).
DOI: 10.1038/s42003-024-07083-8