78306-08-8

Basic information

• Product Name: (2R,3S,4S)-2,3-trans-3,4-trans-3,3',4',7-tetrahydroxy-4-<(2R,3R)-2,3-cis-3,3',4',5,7-pentahydroxyflavan-8-yl>flavan
• CAS NO: 78306-08-8
• Molecular Weight: 562.53
• Mol File: 78306-08-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3S,4S)-2,3-trans-3,4-trans-3,3',4',7-tetrahydroxy-4-<(2R,3R)-2,3-cis-3,3',4',5,7-pentahydroxyflavan-8-yl>flavan(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4S)-2,3-trans-3,4-trans-3,3',4',7-tetrahydroxy-4-<(2R,3R)-2,3-cis-3,3',4',5,7-pentahydroxyflavan-8-yl>flavan(78306-08-8)
• EPA Substance Registry System: (2R,3S,4S)-2,3-trans-3,4-trans-3,3',4',7-tetrahydroxy-4-<(2R,3R)-2,3-cis-3,3',4',5,7-pentahydroxyflavan-8-yl>flavan(78306-08-8)

Safety Data

• Hazardous Substances Data: 78306-08-8(Hazardous Substances Data)

Upstream product

• 967-27-1 (+)-mollisacacidin 
• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 

Relevant articles and documents

STRUCTURE AND SYNTHESIS OF PHLOBATANNINS RELATED TO (-)-FISETINIDOL-(-)-EPICATECHIN PROFISETINIDINS

Several members of the class of natural 'phlobaphene' condensed tannins, representing the products of C-ring isomerization of (-)-fisetinidol-(4α,8)-(-)-epicatechin profisetinidins have been characterized.These comprise four functionalized tetrahydropyranochromenes, two -analogues and four -regioisomers.A novel protocol of effecting differentiation between the regio-isomers based on homonuclear NOE difference spectroscopy (1H NMR) is proposed.The structures of some of the natural products were confirmed by synthesis via base-catalysed rearrangement of their presumed precursors.Under these mild alkaline conditions, the biflavanoids are susceptible to epimerization at C-2 (F-ring) hence leading to conversion of a (-)-epicatechin to a (-)-catechin DEF moiety.The natural occurence of pyran rearranged analogues related to both these units presumably reflects similar mechanisms for the in vivo and in vitro processes.