Ethyl 4'-hydroxy-3'-methoxycinnamate
[CAS# 4046-02-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Ethyl ester compound
• Name: Ethyl 4'-hydroxy-3'-methoxycinnamate
• Synonyms: Ethyl ferulate
• Molecular Formula: C₁₂H₁₄O₄
• Molecular Weight: 222.24
• CAS Registry Number: 4046-02-0
• EC Number: 223-745-5
• SMILES: CCOC(=O)/C=C/C1=CC(=C(C=C1)O)OC

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 57 °C (Expl.)
• Index of Refraction: 1.566, Calc.^*
• Boiling Point: 382.3±0.0 °C (760 mmHg), Calc.^*, 164-166 °C (0.5 mmHg)
• Flash Point: 132.5±17.2 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362+P364-P403+P233-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Ethyl 4'-hydroxy-3'-methoxycinnamate is a chemical compound that belongs to the cinnamate family, a group of organic compounds characterized by the presence of a cinnamic acid derivative. It is an ester derivative of 4-hydroxy-3-methoxycinnamic acid, formed by the esterification of the hydroxyl group of the acid with an ethyl group. The compound is recognized for its potential applications in various industries, particularly in cosmetics and pharmaceutical formulations. Its discovery and development are closely linked to the broader research into the uses of cinnamate derivatives, which are valued for their antioxidant, anti-inflammatory, and UV-protective properties.

The discovery of ethyl 4'-hydroxy-3'-methoxycinnamate can be traced to the ongoing exploration of cinnamate esters and their biological activities. Cinnamic acid derivatives have long been studied for their ability to modulate biological systems, with particular attention given to their effects on skin health. The esterification of 4-hydroxy-3-methoxycinnamic acid with ethyl alcohol led to the formation of ethyl 4'-hydroxy-3'-methoxycinnamate, a compound that combines the antioxidant and anti-inflammatory properties of its parent acid with enhanced solubility and stability due to the ethyl ester group.

Ethyl 4'-hydroxy-3'-methoxycinnamate is most commonly used in cosmetic and skincare products, where it functions primarily as a UV filter. As a UV-absorbing compound, it helps protect the skin from the harmful effects of ultraviolet (UV) radiation, which can cause premature aging, DNA damage, and skin cancer. The compound absorbs UVB light effectively, preventing it from penetrating the skin and causing damage. This makes ethyl 4'-hydroxy-3'-methoxycinnamate an important ingredient in sunscreen formulations, where it enhances the product's ability to protect the skin from sunburn and other UV-related skin damage. Due to its stability and safety profile, it is widely incorporated into various types of sunscreens, including those designed for sensitive skin.

In addition to its use as a UV filter, ethyl 4'-hydroxy-3'-methoxycinnamate also exhibits antioxidant properties. The compound has been shown to scavenge free radicals, reducing oxidative stress that can lead to cellular damage. This antioxidant activity is particularly beneficial in preventing signs of skin aging, such as wrinkles and fine lines, which are often caused by the accumulation of oxidative damage over time. As a result, the compound is also incorporated into anti-aging skincare products, where it helps protect the skin from oxidative stress and maintains a youthful appearance.

Beyond the cosmetic industry, ethyl 4'-hydroxy-3'-methoxycinnamate has also been studied for its potential pharmaceutical applications. Its anti-inflammatory properties make it a candidate for use in the treatment of inflammatory skin conditions such as eczema and psoriasis. The compound may help reduce redness, swelling, and irritation associated with these conditions by modulating inflammatory pathways. Additionally, its antioxidant activity could contribute to the prevention of chronic inflammatory diseases, where oxidative stress plays a key role.

The ongoing research into the biological activities of ethyl 4'-hydroxy-3'-methoxycinnamate continues to reveal its versatile properties. It is not only valued for its use in cosmetic formulations but also for its broader potential in therapeutic applications. As interest in natural and effective compounds for skincare and pharmaceutical use grows, ethyl 4'-hydroxy-3'-methoxycinnamate is expected to remain a key ingredient in the development of new products aimed at promoting skin health and preventing damage from environmental stressors.

References

2024. Immobilization of laccase on mesoporous metal organic frameworks for efficient cross-coupling of ethyl ferulate. World Journal of Microbiology and Biotechnology, 40(9).
DOI: 10.1007/s11274-024-04125-5

2024. Economical and Facile Synthesis of Monolignols. BioEnergy Research, 17(3).
DOI: 10.1007/s12155-024-10779-8

2023. Ethyl ferulate suppresses post-myocardial infarction myocardial fibrosis by inhibiting transforming growth factor receptor 1. Phytomedicine, 120.
DOI: 10.1016/j.phymed.2023.155118