76549-34-3

Basic information

• Product Name: Symplocosidin
• CAS NO: 76549-34-3
• Molecular Weight: 304.299
• Mol File: 76549-34-3.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Symplocosidin(CAS DataBase Reference)
• NIST Chemistry Reference: Symplocosidin(76549-34-3)
• EPA Substance Registry System: Symplocosidin(76549-34-3)

Safety Data

• Hazardous Substances Data: 76549-34-3(Hazardous Substances Data)

Upstream product

• 485-80-3 S-adenosyl-L-methionine 
• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 52248-03-0 S-adenosyl-L-methionine p-toluenesulfonate salt 

Downstream Products

• 51196-02-2 5,7,3',4'-tetra-O-methylepicatechin 

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.

Preparation and characterization of Catechin sulfates, glucuronides, and methylethers with metabolic interest

Catechins are major polyphenols in many plant foods that have been related to health promotion. In the human organism they are largely metabolized to different conjugates (sulfates, glucuronides, and methylethers), which are further found in plasma and would contribute to the biological effects associated with the intake of the parent compounds. Circulating metabolites are likely to possess biological properties different from those of the original compounds, and therefore, it is important to evaluate their activity, for which sufficient amounts of them are required that cannot be obtained by isolation from biological fluids. This paper describes the preparation of the methyl, sulfate, and glucuronide derivatives of catechins using different chemical syntheses and their characterization by HPLC-DAD-ESI/MS. MS2 fragmentation of the compounds was also described that allowed the determination of the location of the different substituents on the catechin aglycones. The procedures optimized allowed the preparation of (epi)catechin sulfates, glucuronides, and methylethers conjugated at positions 3' and 4', as well as the sulfates at positions 5 and 7 with satisfactory yields for their further isolation by semipreparative-HPLC in view of their use in in vitro/ex vivo assays.

Compositions and methods of use of derivatized flavanols

The invention relates to compositions containing derivatized flavanols such as methylated flavanols, and methods of use thereof for prophylactic or therapeutic treatment of a human or a veterinary animal for example as anti-platelet agents.