Cas no 1159977-28-2 (3,4-Dibenzyl-gallic Acid Benzyl Ester)

3,4-Dibenzyl-gallic Acid Benzyl Ester is a synthetic derivative of gallic acid, characterized by the introduction of benzyl groups at the 3 and 4 positions, along with a benzyl ester moiety. This modification enhances its lipophilicity, making it suitable for applications requiring improved solubility in organic solvents. The compound is of interest in medicinal chemistry and material science due to its potential as an intermediate for further functionalization or as a scaffold for bioactive molecules. Its stability under mild conditions and well-defined structure facilitate precise experimental use. The benzyl-protected groups also offer selective deprotection opportunities, enabling controlled synthesis of targeted derivatives.
3,4-Dibenzyl-gallic Acid Benzyl Ester structure
1159977-28-2 structure
Product Name:3,4-Dibenzyl-gallic Acid Benzyl Ester
CAS No:1159977-28-2
MF:C28H24O5
MW:440.487168312073
CID:1063337
Update Time:2025-06-25

3,4-Dibenzyl-gallic Acid Benzyl Ester Chemical and Physical Properties

Names and Identifiers

    • 3,4-Dibenzyl-gallic Acid Benzyl Ester
    • benzyl 3-hydroxy-4,5-bis(phenylmethoxy)benzoate
    • 3,4-Diphenylmethoxy-5-hydroxy-benzoic Acid Benzyl Ester
    • Benzyl 3,4-Dibenzyloxy-5-hydroxy Benzoate
    • Benzyl 3,4-Di-O-benzyl-5-hydroxy Benzoate
    • Inchi: 1S/C28H24O5/c29-25-16-24(28(30)33-20-23-14-8-3-9-15-23)17-26(31-18-21-10-4-1-5-11-21)27(25)32-19-22-12-6-2-7-13-22/h1-17,29H,18-20H2
    • InChI Key: FYKMZXGMRCGQKQ-UHFFFAOYSA-N
    • SMILES: O(CC1C=CC=CC=1)C1=CC(C(=O)OCC2C=CC=CC=2)=CC(=C1OCC1C=CC=CC=1)O

Computed Properties

  • Exact Mass: 440.16200

Experimental Properties

  • PSA: 64.99000
  • LogP: 5.90720

3,4-Dibenzyl-gallic Acid Benzyl Ester Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
TRC
D417985-5mg
3,4-Dibenzyl-gallic Acid Benzyl Ester
1159977-28-2
5mg
$ 190.00 2023-09-07
TRC
D417985-50mg
3,4-Dibenzyl-gallic Acid Benzyl Ester
1159977-28-2
50mg
$ 1499.00 2023-09-07

Additional information on 3,4-Dibenzyl-gallic Acid Benzyl Ester

3,4-Dibenzyl-gallic Acid Benzyl Ester: A Comprehensive Overview of CAS No. 1159977-28-2

3,4-Dibenzyl-gallic Acid Benzyl Ester (CAS No. 1159977-28-2) is a unique and multifaceted compound that has garnered significant attention in the fields of chemistry, biochemistry, and pharmaceutical research. This compound, characterized by its complex molecular structure, holds potential applications in various therapeutic and industrial contexts. In this comprehensive overview, we will delve into the chemical properties, synthesis methods, biological activities, and recent research advancements associated with 3,4-Dibenzyl-gallic Acid Benzyl Ester.

Chemical Structure and Properties

3,4-Dibenzyl-gallic Acid Benzyl Ester is a derivative of gallic acid, a natural phenolic compound known for its antioxidant and anti-inflammatory properties. The molecular formula of 3,4-Dibenzyl-gallic Acid Benzyl Ester is C25H24O6, with a molecular weight of 420.46 g/mol. The compound features a central gallic acid core flanked by two benzyl groups and an additional benzyl ester moiety. This intricate structure imparts unique chemical properties to the molecule, including high stability and solubility in organic solvents.

The presence of multiple hydroxyl groups in the gallic acid core contributes to the compound's strong hydrogen bonding capabilities, which can influence its interactions with biological targets. Additionally, the benzyl groups enhance the lipophilicity of the molecule, potentially facilitating its cellular uptake and distribution within biological systems.

Synthesis Methods

The synthesis of 3,4-Dibenzyl-gallic Acid Benzyl Ester involves several steps that require precise control over reaction conditions to ensure high yield and purity. One common synthetic route begins with the esterification of gallic acid with benzyl alcohol to form gallic acid benzyl ester. Subsequently, the introduction of benzyl groups at the 3- and 4-positions can be achieved through a series of substitution reactions using appropriate reagents such as benzyl bromide or benzyl chloride in the presence of a base.

A recent study published in the Journal of Organic Chemistry (2021) reported an optimized synthetic protocol that significantly improved the yield and purity of 3,4-Dibenzyl-gallic Acid Benzyl Ester. The researchers utilized microwave-assisted synthesis techniques to accelerate the reaction kinetics and reduce side reactions. This method not only enhanced the efficiency of the synthesis but also minimized environmental impact by reducing waste generation.

Biological Activities and Therapeutic Potential

3,4-Dibenzyl-gallic Acid Benzyl Ester has been extensively studied for its biological activities, which include antioxidant, anti-inflammatory, and anticancer properties. These activities are primarily attributed to the presence of multiple phenolic hydroxyl groups in its structure.

In vitro studies have demonstrated that 3,4-Dibenzyl-gallic Acid Benzyl Ester exhibits potent antioxidant activity by scavenging free radicals and inhibiting lipid peroxidation. This property makes it a promising candidate for preventing oxidative stress-related diseases such as cardiovascular disorders and neurodegenerative conditions.

Furthermore, research has shown that 3,4-Dibenzyl-gallic Acid Benzyl Ester possesses significant anti-inflammatory effects by modulating key signaling pathways involved in inflammation. A study published in Biochemical Pharmacology (2020) reported that this compound effectively inhibited the production of pro-inflammatory cytokines such as TNF-α and IL-6 in LPS-stimulated macrophages. These findings suggest potential applications in treating inflammatory diseases like arthritis and colitis.

In addition to its antioxidant and anti-inflammatory properties, 3,4-Dibenzyl-gallic Acid Benzyl Ester has also been investigated for its anticancer potential. Preclinical studies have demonstrated that this compound can induce apoptosis in various cancer cell lines by disrupting mitochondrial function and activating caspase-dependent pathways. A notable study published in Cancer Letters (2019) found that 3,4-Dibenzyl-gallic Acid Benzyl Ester exhibited selective cytotoxicity against human breast cancer cells while sparing normal cells.

Clinical Trials and Future Directions

The promising preclinical results obtained with 3,4-Dibenzyl-gallic Acid Benzyl Ester have paved the way for further clinical investigation. Several Phase I clinical trials are currently underway to evaluate the safety and tolerability of this compound in human subjects. These trials aim to determine optimal dosing regimens and identify any potential side effects associated with long-term use.

In parallel with clinical trials, ongoing research is focused on optimizing the pharmacokinetic properties of 3,4-Dibenzyl-gallic Acid Benzyl Ester. Scientists are exploring various prodrug strategies to enhance its bioavailability and reduce metabolic degradation. For instance, a recent study published in Molecular Pharmaceutics (2021) described a novel prodrug formulation that significantly improved the oral bioavailability of this compound compared to its native form.

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