Ethyl Ferulate / Ethyl 4-hydroxy-3-methoxycinnamate CAs 4046-02-0

Product Overview

Ethyl ferulate (CAS 4046-02-0) , also known as ethyl 4-hydroxy-3-methoxycinnamate, is the ethyl ester derivative of ferulic acid. It is a naturally occurring phenolic ester found in various plant species and is commonly used as a reference standard and research compound. Chemically, it has the molecular formula C₁₂H₁₄O₄ and a molecular weight of 222.24 g/mol. It is a white to off-white crystalline powder with good solubility in organic solvents such as ethanol, methanol, and DMSO, and limited aqueous solubility. The compound exhibits characteristic UV absorption spectra and is stable under proper storage conditions. This product is supplied at ≥98% purity as determined by HPLC analysis.

Synthetic Process:

Ethyl ferulate is typically prepared via esterification of ferulic acid with ethanol. The synthetic process involves the following steps:

Preparation of Ferulic Acid: Ferulic acid is first prepared through the Knoevenagel condensation of vanillin with malonic acid in the presence of a base catalyst. The reaction mixture is heated under reflux, followed by acidification to precipitate ferulic acid. The crude product is purified by recrystallization.

Esterification: The purified ferulic acid is dissolved in ethanol and treated with a catalytic amount of concentrated sulfuric acid or other suitable acid catalyst. The mixture is heated under reflux for several hours to drive the esterification to completion.

Final Product Isolation: The reaction mixture is cooled, neutralized with sodium bicarbonate solution, and extracted with an organic solvent. The organic layer is washed, dried over anhydrous sodium sulfate, and concentrated. The crude product is purified by column chromatography and recrystallization to yield ethyl ferulate with ≥98% purity. Structural confirmation is performed by NMR and mass spectrometry.

Mechanism of Action

Ethyl ferulate exhibits a range of biological activities relevant to research applications:

• Antioxidant Activity: The phenolic hydroxyl group effectively scavenges free radicals and reactive oxygen species, providing protection against oxidative stress

• Enzyme Inhibition: Acts as an inhibitor of certain metabolic enzymes, including tyrosinase and cyclooxygenase isoforms

• Anti-inflammatory Effects: Modulates inflammatory pathways by suppressing the production of inflammatory mediators and cytokines

• Photoprotective Properties: Exhibits UV-absorbing properties, making it of interest in photoprotection research

Research Applications & Market Significance

Ethyl ferulate is a valuable research compound in multiple fields:

• Natural Product Chemistry: Used as a reference standard for the identification and quantification of ferulic acid derivatives in plant extracts

• Antioxidant Research: Studied for its potential to protect biological systems from oxidative damage

• Cosmetic Research: Investigated for potential applications in skin care and photoprotection formulations

• Pharmaceutical Research: Explored as a lead compound for the development of novel therapeutic agents

Quality Specifications

Our ethyl ferulate is manufactured under strict quality control conditions:

• Purity: ≥98.0% determined by HPLC area normalization

• Identity confirmed by NMR (¹H and ¹³C) and mass spectrometry

• Water content: ≤1.0% determined by Karl Fischer titration

• Residual solvents: Meet ICH Q3C guidelines

• Each batch accompanied by comprehensive Certificate of Analysis (COA)

• Stable for 24 months when stored at 2-8°C in sealed containers protected from light

Packaging & Shipping

We offer flexible packaging options to meet diverse customer needs:

• Research quantities: 20mg, 100mg amber glass vials

• Bulk quantities: 1g amber glass bottles

• Custom packaging available upon request

• Shipped at ambient temperature for routine orders

• International shipping available with proper documentation

• Cold chain shipping available upon request for temperature-sensitive orders