Methyl Syringate

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Cat Number

INT884355

CAS Number

884-35-5

For research use only. We do not supply to patients.

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Product Detail Description Scientific Support Customer Q&A

CAS Number

884-35-5

EINECS

429-050-5

Storage

Room temperature

Synonyms

Syringic acid monomethyl ester;4-Hydroxy-3,5-Dimethoxybenzoic Acid Methyl Ester;Benzoic acid, 4-hydroxy-3,5-dimethoxy-, methyl ester

Molecular Formula

C10H12O5

Molecular Weight

212.2

Appearance

White solid

Melting Point

103-107℃

Boiling Point

312.03℃

Relative Density

1.3

pKa

8.38

General Description

Methyl Syringate (methyl 3,5-dimethoxy-4-hydroxybenzoate) is a methyl ester of syringic acid, a natural phenolic compound found in plants, fruits, and wine. As a methyl ester prodrug, it is more lipophilic than the free acid, improving membrane penetration. Its trimethoxy substitution pattern (3,4,5-trimethoxy on the aromatic ring) is shared with several pharmacologically important natural products.

Mechanism of Action

Methyl Syringate exhibits antioxidant activity through multiple mechanisms: it scavenges free radicals (DPPH, ABTS, superoxide), chelates transition metal ions (particularly iron and copper), and induces the expression of endogenous antioxidant enzymes including superoxide dismutase (SOD) and catalase via Nrf2/ARE pathway activation. The methyl ester form is hydrolyzed by plasma and tissue esterases to syringic acid in vivo, and the phenolic hydroxy groups at the 4-position are critical to its antioxidant function.

Application

Methyl Syringate is used in pharmaceutical and nutraceutical research as a natural antioxidant with potential applications in skin protection (UV-induced oxidative damage), anti-inflammatory formulations, and metabolic health. Its methoxy-substituted phenolic structure is of interest in studies of cardiovascular health and neurodegeneration. It is also used as a flavor compound in the food and fragrance industries.

Methyl syringate (MS) is an efficient natural mediator for bacterial and fungal laccases in oxidizing non-phenolic lignin units. Among the syringyl-type phenolics studied (MS, acetosyringone, syringaldehyde), MS is the poorest laccase substrate but yields the highest conversion of veratryl alcohol to veratraldehyde (up to 33% at 1:1 ratio; over 80% at 10:1 mediator/substrate ratio). The efficiency of laccase-mediator systems depends primarily on the stability of the phenoxy radical formed: electron-donating para-substituents stabilize the radical, making MS (with the weakest electron-withdrawing group) superior to acetosyringone and syringaldehyde. Neutral pH (6-7) optimizes the balance between radical reactivity and stability.

Fig. 1 The catalytic cycle of the laccase-mediator systems. (Rosado T.; et al. 2012)

References

Rosado T, et al. Methyl syringate: an efficient phenolic mediator for bacterial and fungal laccases. Bioresource technology, 2012, 124: 371-378.

What is the recommended storage condition for Methyl Syringate?

It should be stored at controlled room temperature in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

What documentation is provided with each batch of Methyl Syringate?

Each batch is accompanied by a Certificate of Analysis (COA) covering identity, potency, and relevant purity tests. Safety Data Sheets (SDS) are available upon request.

Is Methyl Syringate available in high-chemical-purity grade for pharmaceutical synthesis?

Yes, it is supplied in high chemical purity grades suitable for demanding pharmaceutical intermediate applications. Specifications and analytical data are available upon request.

Is Methyl Syringate compatible with common organic solvents used in pharmaceutical synthesis?

Solubility and compatibility information is available in the technical data sheet. For specific solvent compatibility questions, please contact our technical team.

Is Methyl Syringate manufactured under GMP conditions?

It is produced in facilities operating under applicable GMP or equivalent quality standards, ensuring consistent product quality and compliance with pharmaceutical industry requirements.