24093-81-0

Basic information

• Product Name: (4'-O-methyl)methyl gallate
• Synonyms: (4'-O-methyl)methyl gallate
• CAS NO: 24093-81-0
• Molecular Formula: C₉H₁₀O₅
• Molecular Weight: 198.1727
• Mol File: 24093-81-0.mol
• Article Data: 25

Chemical Properties

• Melting Point: 147.0 to 151.0 °C
• Boiling Point: 400.4°C at 760 mmHg
• Flash Point: 164.4°C
• Appearance: /
• Density: 1.337g/cm³
• Vapor Pressure: 5.51E-07mmHg at 25°C
• Refractive Index: 1.567
• PKA: 8?+-.0.15(Predicted)
• CAS DataBase Reference: (4'-O-methyl)methyl gallate(CAS DataBase Reference)
• NIST Chemistry Reference: (4'-O-methyl)methyl gallate(24093-81-0)
• EPA Substance Registry System: (4'-O-methyl)methyl gallate(24093-81-0)

Safety Data

• Hazardous Substances Data: 24093-81-0(Hazardous Substances Data)

Usage

General Description

(4'-O-methyl)methyl gallate is a chemical compound that belongs to the class of organic compounds known as gallates. It is derived from gallic acid, and its structure includes a methyl group attached to the phenolic hydroxyl group at the 4' position. (4'-O-methyl)methyl gallate has been studied for its potential antioxidant and anti-inflammatory effects, as well as for its ability to inhibit the growth of cancer cells. It has also shown promise as a natural preservative for extending the shelf life of food and cosmetic products. Additionally, (4'-O-methyl)methyl gallate has been investigated for its potential use in the development of pharmaceuticals and functional foods due to its beneficial properties. Overall, this compound has garnered interest for its diverse biological activities and potential applications in various industries.

InChI:InChI=1/C9H10O5/c1-13-8-6(10)3-5(4-7(8)11)9(12)14-2/h3-4,10-11H,1-2H3

Upstream product

• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 4319-02-2 4-O-methylgallic acid 
• 99-24-1 methyl galloate 
• 20189-90-6 3,4,5-triacetoxy-benzoic acid methyl ester 
• 13089-97-9 methyl 3,5-diacetoxy-4-methoxy benzoate 
• 75-93-4 methyl bisulfate 
• 186581-53-3 diazomethane 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 60-29-7 diethyl ether 
• 83553-80-4 3,5-Di-O-acetylgallussaeuremethylester 

Downstream Products

• 1916-07-0 3,4,5-trimethoxybenzoic acid methyl ester 
• 83011-43-2 3-hydroxy-4,5-dimethoxybenzoate 
• 63542-40-5 5-(hydroxymethyl)-2-methoxybenzene-1,3-diol 
• 1402404-92-5 1,3-bis(benzyloxy)-5-(bromomethyl)-2-methoxybenzene 
• 79043-20-2 (±)-N-(ethoxycarbonyl)-5'-hydroxynorreticuline 
• 63909-38-6 1-(benzyloxy)-2-methoxy-4-[(E)-2-nitroethenyl]benzene 

Relevant articles and documents

Vanadium-Catalyzed Oxidative Intramolecular Coupling of Tethered Phenols: Formation of Phenol-Dienone Products

A mild and efficient method for the vanadium-catalyzed intramolecular coupling of tethered free phenols is described. The corresponding phenol-dienone products are prepared directly in good yields with low catalyst loadings. Electronically diverse tethered phenol precursors are well tolerated, and the catalytic method was effectively applied as the key step in syntheses of three natural products and a synthetically useful morphinan alkaloid precursor.

Synthesis and in vitro antimalarial activity of alkyl esters of gallate as a growth inhibitor of plasmodium falciparum

This study is aimed to synthesize alkyl esters gallate and determine its in vitro antimalarial activity against parasite Plasmodium falciparum. Fourteen compounds of alkyl esters gallate were synthesized by esterification of the carboxyl group of gallic acid with a series of alkyl alcohols, as well as methoxylation of the hydroxy groups on the aromatic ring of gallic acid. Antimalarial activity of the synthesized alkyl esters gallate were expressed by IC50 value, with gallic acid as an original compound and artemisin as a positive control. Compared to gallic acid, eleven synthesized compounds of alkyl esters gallate, have a greater antimalarial activity against Plasmodium falciparum. On the other hand, three compounds, that are propyl gallate, butyl gallate and trimethoxy methyl gallate, showed a lower antimalarial activity. Moreover, compared to gallic acid (IC50: 194.86 mM) and artemisin (IC50: 0.5 mM), two synthesized compounds of alkyl gallates, namely methyl gallate and hexyl gallate exhibited the stronger antimalarial activity against Plasmodium falciparum, with IC50 value of 0.03 mM and 0.11 mM, respectively. Our result clearly demonstrated that methyl gallate and hexyl gallate as a promising candidate for the new antimalarial agents.

A Regio- and Diastereoselective Anodic Aryl–Aryl Coupling in the Biomimetic Total Synthesis of (?)-Thebaine

The biosynthesis of thebaine is based on the regioselective, intramolecular, oxidative coupling of (R)-reticuline. For decades, chemists have sought to mimic this coupling by using stoichiometric oxidants. However, all approaches to date have suffered from low yields or the formation of undesired regioisomers. Electrochemistry would represent a sustainable alternative in this respect but all attempts to accomplish an electrochemical synthesis of thebaine have failed so far. Herein, a regio- and diastereoselective anodic coupling of 3′,4′,5′-trioxygenated laudanosine derivatives is presented, which finally enables electrochemical access to (?)-thebaine.