224434-07-5

Basic information

• Product Name: (-)-EPIGALLOCATECHIN 3-(4''-O-METHYL)GALLATE
• Synonyms: (-)-EPIGALLOCATECHIN 3-(4''-O-METHYL)GALLATE;(-)-Epigallocatechin 3-(4''-O-Methyl)gallate 〔(-)-EGCg-4''-O-Me〕
• CAS NO: 224434-07-5
• Molecular Formula: C23H20O11
• Molecular Weight: 472.4
• Mol File: 224434-07-5.mol
• Article Data: 12

Chemical Properties

• Melting Point: 226-228 °C (decomp)
• Boiling Point: 879.0±65.0 °C(Predicted)
• Appearance: /
• Density: 1.77±0.1 g/cm3(Predicted)
• PKA: 8.55±0.15(Predicted)
• CAS DataBase Reference: (-)-EPIGALLOCATECHIN 3-(4''-O-METHYL)GALLATE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-EPIGALLOCATECHIN 3-(4''-O-METHYL)GALLATE(224434-07-5)
• EPA Substance Registry System: (-)-EPIGALLOCATECHIN 3-(4''-O-METHYL)GALLATE(224434-07-5)

Safety Data

• Hazardous Substances Data: 224434-07-5(Hazardous Substances Data)

Usage

General Description

(-)-Epigallocatechin 3-(4''-O-methyl)gallate, also known as EGCG3''Me, is a natural polyphenol compound found in green tea. It is a methylated derivative of epigallocatechin gallate (EGCG), which is known for its antioxidant and anti-inflammatory properties. EGCG3''Me has been shown to have stronger anti-proliferative and anti-inflammatory effects compared to EGCG. Its potential health benefits include cancer prevention, cardiovascular protection, and neuroprotective effects. Research also suggests that EGCG3''Me may have potential as a therapeutic agent for certain diseases, making it an area of interest for further study in the field of natural medicine and drug development.

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Relevant articles and documents

Identification and characterization of methylated and ring-fission metabolites of tea catechins formed in humans, mice, and rats.

(-)-Epigallocatechin gallate (EGCG), the most abundant tea catechin, has been proposed to be beneficial to human health based on its strong antioxidative and other biological activities in vitro. Inadequate knowledge regarding the bioavailability and biotransformation of EGCG in humans, however, has limited our understanding of its possible beneficial health effects. In this study, 4',4' '-di-O-methyl-EGCG (4',4' '-DiMeEGCG) was detected in human plasma and urine by LC/MS/MS following green tea ingestion. Both 4',4' '-DiMeEGCG and EGCG reached peak plasma values (20.5 +/- 7.7 and 145.4 +/- 31.6 nM, respectively, in 4 subjects) at 2 h after the dose. The half-lives of 4',4' '-DiMeEGCG and EGCG were 4.1 +/- 0.8 and 2.7 +/- 0.9 h, respectively. The cumulative urinary excretion of 4',4' '-DiMeEGCG during a 24 h period was 140.3 +/- 48.6 microg, about 5-fold higher than that of EGCG, but the excreted 4',4' '-DiMeEGCG and EGCG in urine only accounted for about 0.1% of ingested EGCG. (-)-5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone (M4) and (-)-5-(3',4'-dihydroxyphenyl)-gamma-valerolactone (M6), along with another possible ring-fission metabolite, (-)-5-(3',5'-dihydroxyphenyl)-gamma-valerolactone (M6'), were detected in human urine after green tea ingestion. The cumulative excretion of M4, M6', and M6 during a 24 h period ranged from 75 microg to 1.2 mg, 0.6 to 6 mg, and 0.6 to 10 mg, respectively. The combined excretion of all three ring-fission metabolites accounted for 1.5-16% of ingested catechins. M4, M6', and M6 were all observed after the ingestion of pure EGCG or EGC by human subjects, whereas only M6 was produced after EC ingestion. These metabolites as well as monomethylated EGCG were detected in mice and rats after tea or EGCG administration, and the tissue levels reflected the rather low bioavailability of EGCG in rats. The presently characterized methylated EGCG metabolites and ring-fission products exist in substantial quantities and may contribute to the biological activities of tea.

Regioselective synthesis of alkyl EGCG derivatives

The present invention relates to a synthesis method for regioselective alkylation of ((-)-epigallocatechin gallate (-)-EGCG), and in the regioselective alkylation of the (-)-EGCG according to the present invention, EGCG is firstly acetylated and alkylated

A water-soluble enhancer, a method for improving the water soluble, and, a method for preparing aq.

PROBLEM TO BE SOLVED: To provide a water solubility enhancer, a water solubility enhancement method, and an aqueous solution preparation method.SOLUTION: 4"Me-EGCg, 4"Me-GCg, 4"Et-EGCg, or 4"Et-GCg is used as a water solubility enhancer for enhancing solu

Syntheses of methylated catechins and theaflavins using 2-nitrobenzenesulfonyl group to protect and deactivate phenol

An efficient and versatile synthetic method for labile polyphenols was established using 2-nitrobenzenesulfonate (Ns) as a protecting group for phenol. This methodology provides regio-and stereoselective access to a range of methylated catechins, such as methylated epigallocatechin gallates, that are not readily available from natural sources. In addition, biomimetic synthesis of theaflavins from catechins was accomplished using Ns protection to minimize undesired side reactions of electron-rich aromatic rings during oxidation, enabling construction of the complex benzotropolone core in a single-step oxidative coupling reaction. Availability of these compounds will aid detailed structure-biological activity relationship studies of catechins.