72258-70-9

Basic information

• Product Name: (2R,3S,4R,2'R,3'S,2''R,3''S,4''S)-2,2',2''-Tris-(3,4-dihydroxy-phenyl)-3,4,3',4',3'',4''-hexahydro-2H,2'H,2''H-[4,6';8',4'']terchromene-3,7,3',5',7',3'',7''-heptaol
• CAS NO: 72258-70-9
• Molecular Weight: 834.787
• Mol File: 72258-70-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2R,3S,4R,2'R,3'S,2''R,3''S,4''S)-2,2',2''-Tris-(3,4-dihydroxy-phenyl)-3,4,3',4',3'',4''-hexahydro-2H,2'H,2''H-[4,6';8',4'']terchromene-3,7,3',5',7',3'',7''-heptaol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4R,2'R,3'S,2''R,3''S,4''S)-2,2',2''-Tris-(3,4-dihydroxy-phenyl)-3,4,3',4',3'',4''-hexahydro-2H,2'H,2''H-[4,6';8',4'']terchromene-3,7,3',5',7',3'',7''-heptaol(72258-70-9)
• EPA Substance Registry System: (2R,3S,4R,2'R,3'S,2''R,3''S,4''S)-2,2',2''-Tris-(3,4-dihydroxy-phenyl)-3,4,3',4',3'',4''-hexahydro-2H,2'H,2''H-[4,6';8',4'']terchromene-3,7,3',5',7',3'',7''-heptaol(72258-70-9)

Safety Data

• Hazardous Substances Data: 72258-70-9(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 108-24-7 acetic anhydride 
• 57526-59-7 (2R,3S,4S)-2,3-trans-3,4-trans-3,3',4',7-tetrahydroxy-4-<(2R,3S)-2,3-trans-3,3',4',5,7-pentahydroxyflavan-8-yl>flavan 
• 967-27-1 (+)-mollisacacidin 

Relevant articles and documents

Synthesis of Condensed Tannins. Part 14. Biflavanoid Profisetinidins as Synthons. The Acid-Induced 'Phlobaphene'Reaction

Free phenolic - and -2,3-trans-(-)-fisetinidol-(+)-catechin diastereoisomers of both 3,4-trans and 3,4-cis configuration, which serve as synthons for higher oligomers, are available in improved yields from direct condensation, and also via novel 6-iodo-(+)-catechin as an intermediate substrate.Acid-induced transformations of the predominant -all-trans isomer, illustrative of the well-known 'phlobaphene reaction' of condensed tannins, is shown to include ring-isomerization and fission of the inter-flavanoid bond, followed in the latter instance by the alternatives of anthocyanidin formation, positional rearrangement and self-condensation.

CONDENSED TANNINS: COMPETING NUCLEOPHILIC CENTRES IN BIOMIMETIC CONDENSATION REACTIONS

The relative contributions of nucleophilicity and steric hindrance in determining the course of the reacition during the formation of 'angular' triflavonoids are examined by biomimetic-type condensations involving model compounds.Key Word Index - (4,6)-(-)-fisetinidol-8-(4-hydroxybenzyl)-(+)-catechins; 4-(3-ethyl-2,4,6-trihydroxyphenyl)-3,3',4',7-tetrahydroxyflavans; (4,3:4,5)-bi--ethyl phloroglucinols; condensed tannins; nucleophilicity; steric hindrance.