69912-75-0

Basic information

• Product Name: 4'-O-Methylcatechin
• Synonyms: 4'-O-Methylcatechin;(2R,3S)-3,4-Dihydro-2-(3-hydroxy-4-Methoxyphenyl)-2H-1-benzopyran-3,5,7-triol;(2R-trans)-3,4-Dihydro-2-(3-hydroxy-4-Methoxyphenyl)-2H-1-benzopyran-3,5,7-triol
• CAS NO: 69912-75-0
• Molecular Formula: C₁₆H₁₆O₆
• Molecular Weight: 304.29464
• Product Categories: Aromatics;Heterocycles;Metabolites & Impurities
• Mol File: 69912-75-0.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Acetone (Slightly, Sonicated), Methanol (Slightly)
• CAS DataBase Reference: 4'-O-Methylcatechin(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-O-Methylcatechin(69912-75-0)
• EPA Substance Registry System: 4'-O-Methylcatechin(69912-75-0)

Safety Data

• Hazardous Substances Data: 69912-75-0(Hazardous Substances Data)

Upstream product

• 154-23-4 catechin 
• 74-88-4 methyl iodide 
• 52248-03-0 S-adenosyl-L-methionine p-toluenesulfonate salt 
• 128428-19-3 procyanidin B-3 4-O(E)-monomethyl ether 

Downstream Products

• 130878-02-3 (2S,3R,4R,8R,9S)-2-(3,4-Dihydroxy-phenyl)-4-(2,4-dihydroxy-phenyl)-8-(3-hydroxy-4-methoxy-phenyl)-3,4,9,10-tetrahydro-2H,8H-pyrano[2,3-f]chromene-3,5,9-triol 
• 118964-32-2 (2S,3R,4R,7S,8R)-2-(3,4-Dihydroxy-phenyl)-4-(2,4-dihydroxy-phenyl)-8-(3-hydroxy-4-methoxy-phenyl)-3,4,7,8-tetrahydro-2H,6H-pyrano[3,2-g]chromene-3,5,7-triol 
• 119002-92-5 (2R,3S,8R,9S,10S)-10-(2,4-Dihydroxy-phenyl)-8-(3,4-dihydroxy-phenyl)-2-(3-hydroxy-4-methoxy-phenyl)-3,4,9,10-tetrahydro-2H,8H-pyrano[2,3-f]chromene-3,5,9-triol 
• 152675-41-7 (2R,3S,8R,9S,10S)-10-(2,4-Dihydroxy-phenyl)-2-(3-hydroxy-4-methoxy-phenyl)-8-(3,4,5-trihydroxy-phenyl)-3,4,9,10-tetrahydro-2H,8H-pyrano[2,3-f]chromene-3,5,9-triol 
• 130519-76-5 (-)-robinetinidol-(2β-7;4β-8)-(+)-catechin mono-O-methyl ether 
• 118964-34-4 (-)-Fisetinidol-(4α,8)-(+)-catechin 4-O(E)-methyl ether 
• 118964-25-3 (2R,3S,4R,2'R,3'S)-2-(3,4-Dihydroxy-phenyl)-2'-(3-hydroxy-4-methoxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[4,6']bichromenyl-3,7,3',5',7'-pentaol 
• 119065-90-6 (-)-fisetidinol-(4α,6)-(+)-catechin-O-methyl ether 
• 119065-89-3 (-)-fisetidinol-(4β,8)-(+)-catechin-O-methyl ether 
• 123484-75-3 (+)-fisetinidol-(4β,6)-(+)-catechin O-methyl ether 
• 123484-74-2 (+)-fisetinidol-(4α,6)-(+)-catechin O-methyl ether 
• 123484-73-1 (+)-fisetinidol-(4β,8)-(+)-catechin O-methyl ether 
• 123484-72-0 (+)-fisetinidol-(4α,8)-(+)-catechin O-methyl ether 
• 130519-75-4 (-)-robinetinidol-(4β,8)-(+)-catechin mono-O-methyl ether 

Relevant articles and documents

Synthesis and quantitative analysis of plasma-targeted metabolites of catechin and epicatechin

Grape seed polyphenolic extract (GSPE) rich in the flavan-3-ols (+)-catechin and (-)-epicatechin beneficially modulates Alzheimers Disease phenotypes in animal models. The parent molecules in the extract are converted to a series of methylated and glucuronidated derivatives. To fully characterize these metabolites and establish a robust quantitative assay of their levels in biological fluids, we have implemented a partial synthetic approach utilizing chemical methylation followed by enzymatic glucuronidation. Liquid chromatography/time-of-flight mass spectrometry (LC-TOF-MS) and nuclear magnetic resonance (NMR) spectroscopy were used to assign unequivocal structures to the compounds. An analytical method using solid-phase extraction and LC-MS/MS in selective reaction monitoring mode (SRM) was validated for their quantitation in plasma. These studies provide a basis for improvements in future work on the bioavailability, metabolism, and mechanism of action of metabolites derived from dietary flavan-3-ols in a range of interventions.

Enzymatic O-methylation of flavanols changes lag time, propagation rate, and total oxidation during in vitro model triacylglycerol-rich lipoprotein oxidation

3′-O-Methyl derivatives of flavan-3-ols, (+)-catechin (C), (-)-epicatechin (EC), and (-)-catechin gallate (CG) were prepared enzymatically. Hexanal (EC and CG family, 5 mmol/L) and conjugated diene (C and EC family, 0.25-10 mmol/L) formation following CuS

Oligomeric flavanoids. Part 7. Novel base-catalysed pyran rearrangements of procyanidins

Procyanidin B-3 (1) is subject to readily occurring c-ring isomerizations in NaHCO3-Na2CO3 buffer solution to form a novel 8,9-cis-9,10-trans-3,4,9,10-tetrahydro-2H,8H-pyrano[2,3-h;]chromene (3) and a series of 2,3-cis-3,4-trans-4-aryl-2-flavanylbenzopyrans (6), (9), and (12) in which the C-2 pyrocatechol and C-4 ( + )-catechin moieties are interchanged relative to their positions in the biflavanoid (1). These compounds presumably originate via 1,3-aryl migrations in intermediate quinone-methides with concomitant inversion of the absolute configuration at C-3. The lability of the interflavanyl bond at alkaline pH is reflected by the presence of considerable quantities of (+)-catechin as well as high-molecular-mass analogues of precursor (1).