Ethyl cinnamate
[CAS# 103-36-6]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Carboxylic acid and ester perfume >> Aromatic carboxylic acid ester
• Name: Ethyl cinnamate
• Synonyms: Ethyl 3-phenyl propenoate
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 176.21
• CAS Registry Number: 103-36-6
• EC Number: 203-104-6
• FEMA: 2430
• SMILES: CCOC(=O)/C=C/C1=CC=CC=C1

Properties

• Water solubility: insoluble
• Density: 1.1±0.1 g/mL, Calc.^*, 1.049 g/mL (Expl.)
• Melting point: 6-8 °C (Expl.)
• Index of Refraction: 1.55, Calc.^*, 1.558 (Expl.)
• Boiling Point: 269.4±9.0 °C (760 mmHg), Calc.^*, 271 °C (Expl.)
• Flash Point: 148.6±9.9 °C, Calc.^*, 135 °C (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Discovery and Applications

Ethyl cinnamate is an organic compound with the chemical formula C10H12O2. It is the ethyl ester of cinnamic acid, formed through the esterification of cinnamic acid with ethanol. Ethyl cinnamate is a naturally occurring substance, found in several essential oils, including cinnamon oil, and is known for its pleasant, sweet, and spicy aroma. It is commonly used in the fragrance and flavor industries.

Ethyl cinnamate was first synthesized in the early 19th century, and its presence in natural products, such as cinnamon, has long been known. It has gained significance in various commercial applications due to its characteristic fragrance and its role in providing flavor.

In the fragrance industry, ethyl cinnamate is used in the formulation of perfumes, body care products, soaps, and deodorants. Its sweet and warm aroma makes it a common component of floral, fruity, and oriental fragrance compositions. The compound's pleasant scent, along with its stability, contributes to its widespread use in the creation of commercial fragrances.

Ethyl cinnamate also serves as a flavoring agent in the food industry, where it is used to impart a cinnamon-like flavor to products such as candies, baked goods, and beverages. Its inclusion in food products is regulated by food safety authorities to ensure consumer safety. The compound is considered generally recognized as safe (GRAS) for use in flavoring within specified limits.

Beyond its use in fragrances and food products, ethyl cinnamate has been investigated for its potential biological activities. Studies have shown that it has antioxidant, antimicrobial, and anti-inflammatory properties. These activities have led to its exploration in the development of topical formulations, such as creams and lotions, that may offer therapeutic benefits, including skin protection and wound healing.

In addition to its natural occurrence and commercial applications, ethyl cinnamate is also used as an intermediate in the synthesis of other chemical compounds. Its structure allows it to undergo various chemical reactions, making it valuable in the production of derivatives with potential uses in pharmaceuticals and other industries.

Ethyl cinnamate is generally considered safe for its intended applications in food and cosmetics when used within established guidelines. However, as with many aromatic compounds, some individuals may experience allergic reactions to high concentrations, particularly in cosmetic products.

Overall, ethyl cinnamate is an important compound with diverse applications, particularly in the fragrance and flavor industries. Its pleasant aroma, coupled with its biological properties, makes it a useful substance in both commercial and therapeutic contexts.

References

2024. Chemical Composition and Antioxidant Activity of Petroleum Ether Extract from Kaempferia galanga L. Pharmaceutical Chemistry Journal, 57(12).
DOI: 10.1007/s11094-024-03101-5

2024. Economical and Facile Synthesis of Monolignols. BioEnergy Research, 17(4).
DOI: 10.1007/s12155-024-10779-8

2024. The combination of nanoparticles and endophytes boosts Thyme (Thymus vulgaris L.) resistance to drought stress by elevating levels of phenolic compounds, flavonoids, and essential oils. Chemical and Biological Technologies in Agriculture, 11(1).
DOI: 10.1186/s40538-024-00682-x