78185-17-8

Basic information

• Product Name: (-)-fisetinidol-(4β,8)-(+)-catechin hepta-O-methyl ether
• CAS NO: 78185-17-8
• Molecular Weight: 660.718
• Mol File: 78185-17-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (-)-fisetinidol-(4β,8)-(+)-catechin hepta-O-methyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-fisetinidol-(4β,8)-(+)-catechin hepta-O-methyl ether(78185-17-8)
• EPA Substance Registry System: (-)-fisetinidol-(4β,8)-(+)-catechin hepta-O-methyl ether(78185-17-8)

Safety Data

• Hazardous Substances Data: 78185-17-8(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 967-27-1 (+)-mollisacacidin 
• 154-23-4 catechin 
• 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

• 58065-35-3 (+)-catechin tetramethyl ether acetate 
• 51079-25-5 (2R,3S)-(+)-catechin 3',4',5,7-tetramethyl ether 
• 62861-00-1 Tri-O-methyl-(-)-fisetinidol 
• 69127-07-7 (2R,3S,4R)-2,3-trans-3,4-cis-3-acetoxy-4-<(2R,3S)-2,3-trans-3-acetoxy-3,3',4',5,7-pentamethoxyflavan-8-yl>-3',4',7-trimethoxyflavan 

Relevant articles and documents

Oligomeric flavanoids. Part 19. Reductive cleavage of the interflavanyl bond in proanthocyanidins

The interflavanyl bond in profisetinidins 1, 4 and 6, and methyl ethers 3, 5, 28 and 29 procyanidins 24 and 26, and their methyl ethers 25 and 27 is readily subject to cleavage with sodium cyanoboranuide in trifluoroacetic acid at 0 deg C.This method will contribute significantly to the structure elucidation of the 5-deoxy (A-ring) proanthocyanidins from important commercial sources.Boltzmann-averaged heterocyclic ring coupling constants as determined by a conformational global search routine (GMMX) and NOE difference spectroscopy were used to assign unequivocally the diastereotopic methylene protons in the 1H NMR spectra of flavan-3-ols, a prerequisite for corroboration of the cleavage mechanism.

Synthesis of Condensed Tannins. Part 17. Oligomeric (2R,3S)-3,3',4',7,8-Pentahydroxyflavans: Atropisomerism and Conformation of Biphenyl and m-Terphenyl Analogues from Prosopis glandulosa ('Mesquite')

(2R,3S)-2,3-trans-3',4',7,8-Tetrahydroxyflavan-3-ol , the predominant metabolite in the heartwood of Prosopis glandulosa, represents a putative precursor of a variety of oligomers, including conventional - and -biflavan-3-ols, a -1,3-diarylpropylflavan-3-ol, - and atropisomeric -biphenyl-type biflavan-3-ols, and -m-terphenyl-type triflavan-3-ols.Other participants in these condensations are mainly (+)-catechin, and also the flavan-3,4-diol analogue of (+)-mesquitol.Oligomeric structures were confirmed by biomimetic oxidative and acid-induced couplings, and by nuclear Overhauser effect difference spectroscopy.These applications enabled correction of previous structural assignments for atropisomeric -(+)-mesquitol-(+)-catechins and -bis--(+)-catechins, and determination of their conformations.