224434-07-5

Upstream product

• 485-80-3 S-adenosyl-L-methionine 
• 2596-50-1 (-)-epigallocathechin gallate 
• 74-88-4 methyl iodide 
• 901125-32-4 (-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3',4',5'-tris(benzyloxy)-phenyl]chroman-3-yl 3'',5''-dibenzyloxy-4''-methoxybenzoate 
• 1186527-13-8 5-(2R,3R)-5,7-bis(2-nitrophenylsulfonyloxy)-2-(3,4,5-tris(2-nitrophenylsulfonyloxy)phenyl)chroman-3-yl 4-methoxy-3,5-bis(2-nitrophenylsulfonyloxy)benzoate 
• 14031-35-7 S-Adenosyl-L-methionine 
• 1186527-25-2 5-(2S,3R)-5,7-bis(2-nitrophenylsulfonyloxy)-2-(3,4,5-tris(2-nitrophenylsulfonyloxy)phenyl)chroman-3-yl 4-methoxy-3,5-bis(2-nitrophenylsulfonyloxy)benzoate 
• 989-51-5 (-)-gallocatechin 3-gallate 
• 1186527-08-1 3,5-di(2-nitrobenzenesulfonyloxy)-4-methoxybenzoic acid 
• 1186527-23-0 5-((2S,3R)-3-hydroxy-5,7-bis(2-nitrophenylsulfonyloxy)chroman-2-yl)benzene-1,2,3-triyl tris(2-nitrobenzenesulfonate) 
• 148707-39-5 (-)-epigallocatechin 3-O-galloylperacetate 
• 1004981-53-6 5-((2R,3R)-5,7-diacetoxy-3-((3,5-diacetoxy-4-methoxybenzoyl)oxy)chroman-2-yl)-benzene-1,2,3-triyl triacetate 
• 121-79-9 Propyl gallate 
• 19859-89-3 3,5-bis(benzyloxy)-4-methoxybenzoyl chloride 

Relevant academic research and scientific papers

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.

Purification and characterization of a novel O-methyltransferase from Flammulina velutipes

An enzyme catalyzing the methylation of phenolic hydroxyl groups in polyphenols was identified from mycelial cultures of edible mushrooms to synthesize O-methylated polyphenols. Enzyme activity was measured to assess whether methyl groups were introduced

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

Facile synthesis of 4″-O-alkyl-(–)-EGCG derivatives through regioselective deacetylative alkylation

Therapeutic potential of the D-ring methyl ethers of (–)-epigallocatechin-3-gallate [(–)-EGCG] warrants extensive structure–activity relationship study of various D-ring ethers of (–)-EGCG but, for this purpose, efficient synthetic strategy needs to be de

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.

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

Alkyl derivative manufacturing method

PROBLEM TO BE SOLVED: To provide a new method for producing an alkyl derivative of a polyphenol. SOLUTION: The method for producing an alkyl derivative of a polyphenol includes a step of reacting an acetic acid salt and an alkylating agent with the polyphenol. COPYRIGHT: (C)2013,JPOandINPIT

The synthesis of methylated epigallocatechin gallate

Synthesis of methylated epigallocatechin gallate from (-)-epigallocatechin gallate and propylgallate was accomplished using a benzyl (Bn) group as a protecting group for phenols. This methodology provided (-)-epigallocatechin-3-(4-O-methylgallate), which

Solid-phase synthesis of a combinatorial methylated (±)- epigallocatechin gallate library and the growth-inhibitory effects of these compounds on melanoma B16 cells

We report on the solid-phase synthesis of a combinatorial methylated (±)-epigallocatechin gallate (EGCG) library and its biological evaluation. Epigallocatechin gallate (EGCG) and its methylated derivatives, which are members of the catechin family, exhib

Regioselective synthesis of methylated epigallocatechin gallate via nitrobenzenesulfonyl (Ns) protecting group

Regioselective synthesis of methylated epigallocatechin gallate from epigallocatechin was accomplished using a 2-nitrobenzenesulfonyl (Ns) group as a protecting group for phenols. This methodology provided several methylated catechins, which are naturally