Methyl cinnamate
[CAS# 103-26-4]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Carboxylic acid and ester perfume >> Aromatic carboxylic acid ester
• Name: Methyl cinnamate
• Synonyms: Methyl 3-phenyl propenoate; 3-Phenyl-2-propenoic acid methyl ester
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• CAS Registry Number: 103-26-4
• EC Number: 203-093-8
• FEMA: 2698
• SMILES: COC(=O)/C=C/C1=CC=CC=C1

Properties

• Water solubility: insoluble
• Density: 1.1±0.1 g/mL, Calc.^*,1.042 g/mL (Expl.)
• Melting point: 34-38 °C (Expl.)
• Index of Refraction: 1.559, Calc.^*
• Boiling Point: 261.9 °C (760 mmHg), Calc.^*, 260-262 °C (Expl.)
• Flash Point: 141.3±9.9 °C, Calc.^*, >113 °C (Expl.)

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317
• Safety Statements: P261-P272-P280-P302+P352-P321-P333+P317-P362+P364-and

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1B	H317
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

Methyl cinnamate is an organic compound with the chemical formula C9H10O2. It is the methyl ester of cinnamic acid, derived from the esterification of cinnamic acid with methanol. Methyl cinnamate occurs naturally in various essential oils, including cinnamon, and is also a key component in the fragrance and flavor industries. It has a characteristic sweet, floral, and spicy aroma, which is why it is frequently used in perfumes, cosmetics, and food flavorings.

Methyl cinnamate was first synthesized in the laboratory in the 19th century, but it has been known for its presence in cinnamon and other spices much longer. As a synthetic compound, it gained popularity due to its aromatic properties, which are similar to those of cinnamon bark and other cinnamic derivatives.

The main application of methyl cinnamate is in the flavoring and fragrance industries. It is widely used as a flavoring agent in food products, including confectionery, beverages, and baked goods, imparting a sweet and spicy cinnamon-like flavor. The compound is also used extensively in the cosmetic industry, where it is included in perfumes, body lotions, soaps, and other personal care products. Its pleasant aroma and relatively low toxicity make it a popular choice for these applications.

In addition to its use in fragrance and flavoring, methyl cinnamate has been studied for its potential biological and pharmacological effects. Research has indicated that methyl cinnamate exhibits anti-inflammatory, antimicrobial, and antioxidant properties. These properties have led to its exploration in the development of potential therapeutic applications, including its use in creams or lotions for pain relief, as well as in formulations aimed at treating skin conditions such as eczema and psoriasis.

Methyl cinnamate is also a key intermediate in organic synthesis, particularly in the production of various cinnamic acid derivatives. Its chemical structure allows for easy modifications, making it a valuable starting material for the synthesis of other compounds with applications in pharmaceuticals and fine chemicals.

Despite its wide use, methyl cinnamate is generally considered safe for consumption and topical use in regulated quantities. However, some individuals may experience allergic reactions, particularly in products with higher concentrations of the compound. As a result, it is important to follow established safety guidelines for its use in both food and cosmetic products.

Overall, methyl cinnamate is a versatile compound with significant applications in the fragrance, flavor, and pharmaceutical industries. Its aromatic properties, coupled with its biological activity, make it a valuable substance in both commercial and scientific contexts.

References

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2024. Visible light-mediated intermolecular crossed [2+2] cycloadditions using a MOF-supported copper triplet photosensitizer. Nature Catalysis, 7(3).
DOI: 10.1038/s41929-024-01112-9

2024. New frontiers in multicomponent mechanosynthesis for organic molecules: modern marvels. Molecular Diversity, 28(6).
DOI: 10.1007/s11030-024-11053-x