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

Description

(4'-O-methyl)methyl gallate is a gallate compound derived from gallic acid, featuring a methyl group attached to the phenolic hydroxyl group at the 4' position. It has been studied for its potential antioxidant, anti-inflammatory effects, and its ability to inhibit cancer cell growth. (4'-O-methyl)methyl gallate also shows promise as a natural preservative and has potential applications in pharmaceuticals and functional foods due to its beneficial properties.

Uses

Used in Antioxidant Applications:
(4'-O-methyl)methyl gallate is used as an antioxidant for its potential to combat oxidative stress and protect cells from damage, which can contribute to various health issues and the aging process.
Used in Anti-inflammatory Applications:
(4'-O-methyl)methyl gallate is used as an anti-inflammatory agent to help reduce inflammation and alleviate symptoms associated with inflammatory conditions.
Used in Cancer Therapy:
(4'-O-methyl)methyl gallate is used as an anticancer agent for its ability to inhibit the growth of cancer cells, offering a potential therapeutic approach for various types of cancer.
Used in Food and Cosmetic Preservation:
(4'-O-methyl)methyl gallate is used as a natural preservative in the food and cosmetic industries to extend the shelf life of products and maintain their quality over time.
Used in Pharmaceutical Development:
(4'-O-methyl)methyl gallate is used in the development of pharmaceuticals due to its potential health benefits and therapeutic properties, offering a promising avenue for creating new treatments and medications.
Used in Functional Food Industry:
(4'-O-methyl)methyl gallate is used in the development of functional foods for its potential to provide health benefits beyond basic nutrition, contributing to the overall wellness of consumers.

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

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

Downstream Products

• 102078-08-0 (3,5-Dihydroxy-4-methoxy-phenyl)-diphenyl-methanol 
• 4319-02-2 4-O-methylgallic acid 
• 13326-69-7 methyl 3,5-bis(benzyloxy)-4-methoxybenzoate 
• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 103929-80-2 methyl 3,5-di-tert-butyldimethylsilyloxy-4-methoxybenzoate 
• 524941-79-5 4-methoxy-3,5-bis-vinyloxy-benzoic acid methyl ester 
• 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 
• 54186-41-3 2-(3,5-bis(benzyloxy)-4-methoxyphenyl)acetonitrile 
• 24093-82-1 3,5-bis(benzyloxy)-4-methoxybenzyl chloride 
• 54186-42-4 2-(3,5-bis(benzyloxy)-4-methoxyphenyl)acetic acid 
• 54186-43-5 N-(3-methoxyphenylethyl)-(3,5-dibenzyloxy-4-methoxyphenyl)acetamide 
• 171738-30-0 methyl 3,5-diisopropoxy-4-methoxybenzoate 

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.

Bioinspired Total Synthesis of Bussealin e

The first total synthesis of bussealin E, a natural product with a unique cycloheptadibenzofuran scaffold, is reported. A strategy inspired by a proposed biosynthesis was employed whereby a diphenylpropane derivative underwent an oxidative phenolic coupling to forge the tetracyclic ring system. The synthesis of the diphenylpropane featured a key sp2-sp3 Hiyama coupling between a vinyldisiloxane and a benzylic bromide.