Isoferulic Acid 98% Purity Natural Antioxidant Cosmetic Raw Material Pharmaceutical Intermediate Plant Extract CAS 537-73-5 Research Grade High Purity

Product Overview

Isoferulic acid (3-hydroxy-4-methoxycinnamic acid) is a naturally occurring hydroxycinnamic acid and a positional isomer of ferulic acid, distinguished by the relative positions of the hydroxy and methoxy substituents on the aromatic ring. While ferulic acid bears a 4-hydroxy-3-methoxy substitution pattern, isoferulic acid features a 3-hydroxy-4-methoxy arrangement, conferring distinct physicochemical properties and biological activities. This compound is found naturally in various plant sources, including certain medicinal herbs, spices, and essential oils, where it contributes to the plant's antioxidant and antimicrobial defense systems.

Chemically, isoferulic acid is designated as (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid, bearing the molecular formula C₁₀H₁₀O₄ and a molecular weight of 194.18 g/mol. It is a white to pale yellow crystalline powder, exhibiting moderate solubility in ethanol, methanol, and dimethyl sulfoxide (DMSO), with limited aqueous solubility. The compound demonstrates characteristic UV absorption maxima at approximately 240 nm and 320 nm in methanol solution, consistent with the cinnamic acid chromophore.

Isoferulic acid has garnered significant research interest due to its distinct biological activities, including potent antioxidant, anti-inflammatory, and antimicrobial properties, which in some aspects differ from those of its better-known isomer ferulic acid. Our product is supplied at a minimum purity of 98.0% as determined by high-performance liquid chromatography (HPLC) with photodiode array detection, with each batch accompanied by comprehensive Certificate of Analysis.

Synthetic Process

Isoferulic acid can be obtained through natural extraction from plant sources or via chemical synthesis. The synthetic route typically proceeds as follows:

Step 1 – Condensation: Isoferulic acid is synthesized via the Knoevenagel-Doebner condensation between isovanillin (3-hydroxy-4-methoxybenzaldehyde) and malonic acid in the presence of pyridine and piperidine. The reaction is conducted at 80-85°C for 4-6 hours with continuous stirring.

Step 2 – Isolation: Upon completion, the reaction mixture is acidified with dilute hydrochloric acid to precipitate the crude product. The precipitate is collected by filtration, washed with water, and dried.

Step 3 – Purification: The crude product is purified by recrystallization from aqueous ethanol or methanol-water mixture to yield pure isoferulic acid as crystalline solids. The product identity is confirmed by HPLC, NMR, and mass spectrometry.

Mechanism of Action

Isoferulic acid exerts its biological activities through multiple well-characterized mechanisms:

• Free Radical Scavenging: The phenolic hydroxyl group provides potent hydrogen-donating capacity for neutralizing reactive oxygen species (ROS), including superoxide anions, hydroxyl radicals, and peroxyl radicals. The distinct substitution pattern of isoferulic acid influences its radical-scavenging kinetics and efficacy.

• Metal Ion Chelation : The hydroxyl and carboxylate groups facilitate the chelation of transition metal ions such as Fe²⁺ and Cu²⁺, thereby inhibiting Fenton chemistry and subsequent hydroxyl radical generation.

• Enzyme Modulation: Isoferulic acid modulates the activity of key endogenous antioxidant enzymes, including up-regulation of superoxide dismutase (SOD) and catalase (CAT), while inhibiting pro-oxidant enzymes.

• Anti-inflammatory Activity: The compound inhibits the production of pro-inflammatory mediators, including nitric oxide (NO) and prostaglandin E₂ (PGE₂), through suppression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) expression.

• Antimicrobial Activity: Isoferulic acid exhibits antimicrobial properties against various bacterial and fungal strains, contributing to its potential applications in food preservation and pharmaceutical development.

Research Applications & Market Significance

Isoferulic acid holds significant value across multiple research and industrial applications:

• Pharmaceutical Research: Investigated for its anti-inflammatory, antioxidant, and antimicrobial properties, isoferulic acid serves as a lead compound for drug development targeting inflammatory diseases, oxidative stress-related conditions, and infectious diseases.

• Cosmetics and Personal Care: Incorporated into anti-aging skincare formulations and protective products, leveraging its antioxidant and anti-inflammatory properties for skin health benefits.

• Food Preservation: Utilized as a natural preservative and antioxidant in food products, preventing oxidative deterioration and microbial growth.

• Analytical Standards: Serves as a reference material for HPLC and mass spectrometry analysis in quality control and research laboratories.

• Natural Product Chemistry: Used as a reference compound in phytochemical studies and natural product isolation research.

Quality Specifications

Our isoferulic acid is manufactured under controlled conditions with comprehensive quality assurance:

• Purity: ≥98.0% determined by HPLC-DAD (area normalization)

• Structural identity confirmed by FT-IR, UV-Vis, and ¹H-NMR spectroscopy

• Water content: ≤0.5% by Karl Fischer titration

• Residue on ignition: ≤0.2%

• Heavy metals: ≤10 ppm (Pb, As, Hg, Cd) by ICP-MS

• Residual solvents: Meets ICH Q3C guidelines

• Each batch accompanied by comprehensive Certificate of Analysis (COA) with HPLC chromatograms and spectral data

• Stability: 36 months when stored at 2-8°C in sealed containers protected from light and moisture

Packaging & Shipping

We offer diverse packaging options to meet varied application requirements:

• Analytical standards: 20mg amber glass vials with PTFE-lined septa

• Research quantities: 100mg, 500mg amber glass bottles

• Bulk quantities: 1g, 5g HDPE containers with desiccant

• Custom packaging available upon request

• Standard shipments dispatched at ambient temperature with desiccant

• International shipping available with complete documentation (MSDS, COA)

• Temperature-controlled shipping available upon request