94102-41-7

Upstream product

• 77-78-1 dimethyl sulfate 
• 154-23-4 catechin 
• 130659-29-9 Carbonic acid benzyl ester 2-benzyloxycarbonyloxy-4-((2R,3S)-3-hydroxy-5,7-dimethoxy-chroman-2-yl)-phenyl ester 
• 105330-57-2 procyanidin B-3 7-O-β-D-glucopyranoside 
• 103215-59-4 procyanidin B-1 6-C-β-D-glucopyranoside 
• 103215-58-3 procyanidin B-1 8-C-β-D-glucopyranoside 
• 154-23-4 (+/-)-epicatechin 
• 85443-48-7 (2R,3S)-2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)chroman-3,5,7-triol 
• 300346-49-0 (2R,3S)-2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-5,7-dimethoxychroman-3-ol 
• 105330-67-4 C₂₉H₃₈O₁₆ 

Relevant academic research and scientific papers

An efficient synthesis of the four mono methylated isomers of (+)-catechin including the major metabolites and of some dimethylated and trimethylated analogues through selective protection of the catechol ring

The four monomethylated isomers of (+)-catechin in positions 3′, 4′, 5 and 7, two dimethylated derivatives, the 5,7-dimethylcatechin and the 3′, 4′-dimethylcatechin and two trimethylated isomers of (+)-catechin in positions 3′, 5, 7 and 4′, 5, 7 were synthesized by a new method based on successive and selective protections of the various phenol functions present on (+)-catechin. The key step was the selective protection of the catechol ring with dichlorodiphenylmethane and di-tert-butyldichlorosilane.

Selective protection of catechin gives access to the intrinsic reactivity of the two phenol rings during H-abstraction and photo-oxidation

Selective protection of the catechol ring of catechin has been achieved. From this key compound, catechin analogues protected either on the catechol or the resorcinol rings were synthesized. From these analogues, phenoxyl radicals on the catechol or on the resorcinol rings were produced by photo- oxidation (direct irradiation at 308 nm) of the phenolate and by H- abstraction experiments. Spectra of the radicals were recorded at short times before any further chemical evolution. Investigation of catechin behavior itself and comparison with the reactivity of models show that H-abstraction is unselective, whereas photo-oxidation is selective on the catechol ring monoanion establishing that this ring has the lowest pKa. (C) 2000 Elsevier Science Ltd.

Selective O-methylation of polyhydroxyflavan-3-ols via benzyl carbonates

The flavan-3-ols (+)-catechin and (-)-epicatechin were selectively transformed to their 3′,4′-di-O-methyl- and 5,7-di-Omethyl-ethers respectively via benzyl carbonates. Such a regioselectivity is facilitated by marked differences in the pKa values of the

Degradation of (+)-cyanidanol-3 by sodium sulfite in aqueous solution. II. Reactivity of several (+)-cyanidanol-3 derivatives with sodium sulfite

The reactivity of several (+)-cyanidanol-3 (cianidanol) derivatives with sodium sulfite in aqueous solution was investigated at pH 7.5 and 60°C. 5,7-O-Dimethylcianidanol was degraded by sodium sulfite to yield, a water-soluble degradation product, which w