69127-07-7

Basic information

• Product Name: (2S,3R,4S)-2,3-trans-3,4-cis-3-acetoxy-4-<(2R,3S)-2,3-trans-3-acetoxy-3',4',5,7-tetramethoxyflavan-8-yl>-3',4',7-trimethoxyflavan
• CAS NO: 69127-07-7
• Molecular Weight: 744.793
• Mol File: 69127-07-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2S,3R,4S)-2,3-trans-3,4-cis-3-acetoxy-4-<(2R,3S)-2,3-trans-3-acetoxy-3',4',5,7-tetramethoxyflavan-8-yl>-3',4',7-trimethoxyflavan(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4S)-2,3-trans-3,4-cis-3-acetoxy-4-<(2R,3S)-2,3-trans-3-acetoxy-3',4',5,7-tetramethoxyflavan-8-yl>-3',4',7-trimethoxyflavan(69127-07-7)
• EPA Substance Registry System: (2S,3R,4S)-2,3-trans-3,4-cis-3-acetoxy-4-<(2R,3S)-2,3-trans-3-acetoxy-3',4',5,7-tetramethoxyflavan-8-yl>-3',4',7-trimethoxyflavan(69127-07-7)

Safety Data

• Hazardous Substances Data: 69127-07-7(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 78185-25-8 (2S,3R,4S,2'R,3'S)-2,2'-Bis-(3,4-dimethoxy-phenyl)-7,5',7'-trimethoxy-3,4,3',4'-tetrahydro-2H,2'H-[4,8']bichromenyl-3,3'-diol 
• 78185-17-8 (-)-fisetinidol-(4β,8)-(+)-catechin hepta-O-methyl ether 
• 186581-53-3 diazomethane 
• 69127-11-3 (2R,3S,4R)-2,3-trans-3,4-cis-3,3',4',7-tetrahydroxy-4-<(2R,3S)-2,3-trans-3,3',4',5,7-pentahydroxyflavan-8-yl>flavan 

Downstream Products

• 99260-78-3 Acetic acid (2R,3R)-6-bromo-2-(3,4-dimethoxy-phenyl)-4,4,7-trimethoxy-chroman-3-yl ester 
• 69119-50-2 8-bromo-3-O-acetyl-3',4',5,7-tetra-O-methyl-(+)-catechin 
• 131266-32-5 4β-Hydroxy-tri-O-methyl-3-O-acetyl-(-)-fisetinidol-(4α,8)-tetra-O-methyl-3-O-acetyl-(+)-catechin 
• 99260-77-2 4β-methoxy-tri-O-methyl-3-O-acetyl-(-)-fisetinidol-(4α,8)-tetra-O-methyl-3-O-acetyl-(+)-catechin 

Relevant articles and documents

Oligomeric Flavonoids. Part 16. Novel Prorobinetinidins and the First A-Type Proanthocyanidin with a 5-Deoxy A- and 3,4-cis-C-Ring from the Maiden Investigation of Commercial Wattle Bark Extract

Structural examination of the phenolic metabolites of commercially used wattle bark extract reveals the presence of a range of novel flavonoids comprising (-)-epirobinetinidol 1, the first C-methyl proanthocyanidin, (-)-fisetinidol-(4α,8)-6-methyl-(+)-catechin 3, the first prorobinetinidins with 3,4-cis-C-ring configurations 7 and 9, and the unique A-type prorobinetinidin 11 representing the first entry amongst this class of oligoflavonoids exhibiting a 5-deoxy A- and a 3,4-cis-C-ring.They are accompanied by a range of functionalized prorobinetinidin-type tetrahydropyranochromenes 20, 23, 25 and 28 and the trimeric 'isomerization-intermediate' 32, all exhibiting the characteristic structural features that are essential for the use of 'Mimosa' exctract in cold-setting adhesives and leather-tanning applications.In addition, evidence demonstrating that the dynamic A-E conformational equilibrium of flavan-3-ol moieties in condenced tannins may be influenced by external factors is presented.

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.

Synthesis of Condensed Tannins. Part 4. A Direct Biomimetic Approach to - and -Biflavanoids

The generation of flavanyl-4-carbo-cations from flavan-3,4-diols and their condensation with nucleophilic flavan-3-ols to form - and -biflavanoids at ambient temperatures and mildly acidic aqueous conditions apparently simulates the initial step in condensed tannin formation in a number of natural sources.The stereospecificity (or stereoselectivity) of the reaction is conditioned mainly by the 2,3-cis or 2,3-trans stereochemistry of the parent flavan-3,4-diol, but also by the nuclephilicity of the flavan-3-ol, and its regiospecific (or regioselective) course by steric factors arising from variation in substitution of the receptive A-ring of the flavan-3-ol.