125136-17-6

Basic information

• Product Name: (2R,3S,4R)-2,3-trans-3,4-trans-4-(2,4-Dihydroxyphenyl)-3',4',5,7-tetrahydroxyflavan-3-ol
• Synonyms: (2R,3S,4R)-2,3-trans-3,4-trans-4-(2,4-Dihydroxyphenyl)-3',4',5,7-tetrahydroxyflavan-3-ol
• CAS NO: 125136-17-6
• Molecular Weight: 398.369
• Mol File: 125136-17-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2R,3S,4R)-2,3-trans-3,4-trans-4-(2,4-Dihydroxyphenyl)-3',4',5,7-tetrahydroxyflavan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4R)-2,3-trans-3,4-trans-4-(2,4-Dihydroxyphenyl)-3',4',5,7-tetrahydroxyflavan-3-ol(125136-17-6)
• EPA Substance Registry System: (2R,3S,4R)-2,3-trans-3,4-trans-4-(2,4-Dihydroxyphenyl)-3',4',5,7-tetrahydroxyflavan-3-ol(125136-17-6)

Safety Data

• Hazardous Substances Data: 125136-17-6(Hazardous Substances Data)

Upstream product

• 69082-77-5 (2R,3S,4S)-2,3-trans-3,4-trans-4-(2,4,6-trihydroxyphenyl)flavan-3,3',4',7-tetraol 
• 1242246-47-4 C₄₉H₄₂O₈ 
• 480-18-2 taxifolin 
• 69256-15-1 (2R,3S,4R)-(+)-3,4,5,7,3',4'-hexahydroxyflavan 
• 108-46-3 recorcinol 
• 480-17-1 (+)-leucocyanidin 
• 78174-80-8 (2R,3S,4R)-2,3-trans-3,4-cis-4-(2,4,6-trihydroxyphenyl)flavan-3,3',4',7-tetraol 

Downstream Products

• 528-58-5 cyanidin chloride 
• 2948-76-7 fisetinidin chloride 
• 78174-76-2 2,3-cis-3,4-cis-3',4',5,7-tetramethoxy-4-(2,4-dimethoxyphenyl)flavan-3-ol 
• 78284-45-4 (2R,3S,4R)-2,3-trans-3,4-trans-3,3',4',5,7-pentamethoxy-4-(2,4-dimethoxyphenyl)flavan 
• 78284-46-5 (2R,3S,4R)-2,3-trans-3,4-trans-3',4',5,7-tetramethoxy-4-(2,4-dimethoxyphenyl)flavan-3-ol 
• 78284-53-4 (2R,3S,4S)-2,3-trans-3,4-cis-3',4',5,7-tetramethoxy-4-(2,4-dimethoxyphenyl)flavan-3-ol 
• 78284-47-6 (2R,3S,4R)-2,3-trans-3,4-trans-3-acetoxy-3',4',5,7-tetramethoxy-4-(2,4-dimethoxyphenyl)flavan 

Relevant articles and documents

Synthesis and ribonuclease A inhibition activity of resorcinol and phloroglucinol derivatives of catechin and epicatechin: Importance of hydroxyl groups

The reported ribonuclease A inhibitory activity of the green tea extracts prompted us to synthesize novel catechin/epicatechin based conjugates with resorcinol and phloroglucinol with the aim to increase the number of phenolic OH groups. These are found to be more effective inhibitors of ribonuclease A as compared to catechin and epicatechin thus indicating the importance of number of phenolic OH groups for the inhibition of ribonucleolytic activity. Fluorescence studies have been carried out to evaluate the binding parameters. The protein-ligand docking studies are also performed to gain insight into the protein-polyphenols interactions. The epicatechin based polyphenols 1 and 2 also showed inhibition of angiogenin-induced angiogenesis, as determined by chorioallantoic membrane (CAM) assay.

OLIGOMERIC FLAVANOIDS.PART 6.EVIDENCE SUPPORTING THE INVERSION OF ABSOLUTE CONFIGURATION AT 3-C ASSOCIATED WITH BASE CATALYSED A-/B-RING INTERCHANGE OF PRECURSORS HAVING 2,3-TRANS-3,4-CIS-FLAVAN-3-OL CONSTITUENT UNITS

Whereas the enantiomeric 2,3-trans-3,4-trans-arylflavan-3-ols (10) and (12) as biflavanoid models are subject to stereospecific C-ring isomerisation under base catalysis, those with 3,4-cis configuration (11) and (13) are transformed stereoselectively via

Synthesis of Condensed Tannins. Part 1. Stereoselective and Stereospecific Syntheses of Optically Pure 4-Arylflavan-3-ols, and Assessment of their Absolute Stereochemistry at C-4 by means of Circular Dichroism

Stereoselective and also stereospecific condensation at C-4 of flavan-3,4-diols of known absolute configuration with phloroglucinol and resorcinol in acid medium proceeds at ambient temperatures with partial retention of configuration for 2,3-trans-isomers and with inversion for 2,3-cis-analogues.Circular dichroism spectra of the resultant 4-arylflavan-3-ols all exhibit multiple Cotton effects.The sign of high intensity Cotton effects to low wavelength, contributed by aryl chromophores at C-4, may almost invariably be correlated with the absolute configuration at this chiral centre of 2,3-trans-3,4-trans, 2,3-trans-3,4-cis, and 2,3-cis-3,4-trans-isomers.