Methyl trans-Ferulate 98% Purity Natural Antioxidant Cosmetic Raw Material Food Additive Pharmaceutical Intermediate CAS 22329-76-6 Research Grade Hig

Product Overview

Methyl trans-ferulate (methyl trans-4-hydroxy-3-methoxycinnamate) is the methyl ester derivative of trans-ferulic acid, representing the naturally occurring trans-isomeric form of the compound. This methyl esterified derivative is found naturally in various plant sources, including certain essential oils and medicinal herbs, and serves as an important flavor and fragrance compound in addition to its antioxidant properties. The methyl ester modification increases the lipophilic character of the molecule, improving its solubility in organic solvents and oils while preserving the beneficial biological activities of the parent trans-ferulic acid.

Chemically, methyl trans-ferulate is designated as methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate, bearing the molecular formula C₁₁H₁₂O₄ and a molecular weight of 208.21 g/mol. It is a white to off-white crystalline powder, soluble in ethanol, methanol, ethyl acetate, and chloroform, with limited aqueous solubility. The trans-configuration is confirmed by NMR coupling constants (J = 15.8-16.0 Hz for the vinylic protons) and characteristic UV absorption maxima at 236 nm and 322 nm in methanol solution.

The trans-isomer represents the thermodynamically preferred configuration and is the biologically active form, exhibiting superior antioxidant activity compared to the cis-isomer. Our product is supplied as the pure trans-isomer with a minimum purity of 98.0% as determined by HPLC with photodiode array detection, with each batch accompanied by comprehensive Certificate of Analysis.

Synthetic Process

Methyl trans-ferulate is synthesized via Fischer esterification of trans-ferulic acid with methanol under acidic conditions:

Step 1 – Esterification: trans-Ferulic acid (1.0 equivalent) is dissolved in anhydrous methanol with catalytic sulfuric acid (1-2 mol%) as the acid catalyst. The mixture is heated under reflux at 64-65°C for 4-8 hours with continuous stirring. The reaction progress is monitored by TLC using a hexane/ethyl acetate (7:3 v/v) mobile phase.

Step 2 – Purification: Upon completion, the reaction mixture is neutralized and the crude product is extracted with ethyl acetate. The organic layer is washed, dried, and concentrated. The crude product is purified by recrystallization from methanol-water (1:1 v/v) to yield pure methyl trans-ferulate as white crystals.

Step 3 – Quality Control: Each batch undergoes rigorous QC testing including HPLC-DAD purity analysis, isomeric purity confirmation by ¹H-NMR, melting point determination (78-80°C), and heavy metal testing.

Mechanism of Action

Methyl trans-ferulate exerts its biological activities through mechanisms comparable to those of trans-ferulic acid, with enhanced lipophilic properties:

• Free Radical Scavenging: The phenolic hydroxyl group provides potent hydrogen-donating capacity for neutralizing reactive oxygen species (ROS). The trans-configuration provides optimal molecular geometry for radical stabilization.

• Lipid Phase Antioxidant Activity: The enhanced lipophilicity of the methyl ester enables effective partitioning into lipid bilayers and oil phases, providing protection against lipid peroxidation.

• UV Radiation Protection: The conjugated π-electron system provides intrinsic UV absorption in the UV-B and UV-A ranges (280-380 nm), enabling photoprotective applications.

• Synergistic Antioxidant Effects: Demonstrates synergistic antioxidant activity when combined with other phenolic antioxidants and vitamins.

Research Applications & Market Significance

Methyl trans-ferulate has significant value across multiple research and industrial applications:

• Cosmetics and Personal Care: Incorporated into anti-aging skincare formulations, sunscreens, and moisturizers with enhanced skin penetration.

• Food Preservation: Utilized as a natural lipophilic antioxidant in oils, fats, and processed foods.

• Serves as a pharmaceutical intermediate and research compound.

• Flavor and Fragrance Industry: Used as a flavoring agent and fragrance component.

• Analytical Standards: Serves as a reference material for HPLC and mass spectrometry analysis.

Quality Specifications

• Purity: ≥98.0% determined by HPLC-DAD

• Isomeric purity: ≥99% trans-isomer (confirmed by ¹H-NMR)

• Melting point: 78-80°C

• Water content: ≤0.5%

• Heavy metals: ≤10 ppm

• Residual solvents: Meets ICH Q3C guidelines

• Stability: 36 months at 2-8°C protected from light

Packaging & Shipping

• Analytical standards: 2mg, 10mg amber glass vials

• Research quantities: 50mg, 100mg amber glass bottles

• Standard shipments at ambient temperature with desiccant

• International shipping with MSDS and COA documentation