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InChI:InChI=1/C28H22O6/c29-20-14-22(30)21-16-23(31)27(32-25(21)15-20)17-11-12-24-26(13-17)34-28(33-24,18-7-3-1-4-8-18)19-9-5-2-6-10-19/h1-15,23,27,29-31H,16H2/t23-,27+/m0/s1

Upstream product

• 2051-90-3 Dichlorodiphenylmethane 
• 154-23-4 catechin 

Downstream Products

• 300346-49-0 (2R,3S)-2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-5,7-dimethoxychroman-3-ol 
• 300346-47-8 (2R,3S)-2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-5-methoxychroman-3,7-diol 
• 300346-48-9 (2R,3S)-2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-7-methoxychroman-3,5-diol 
• 89329-08-8 acetic acid 3,5-diacetoxy-2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)chroman-7-yl ester 
• 443926-55-4 (2R,3S)-5,7-bis(benzyloxy)-2-(3',4'-dimethoxyphenyl)chroman-3-yl acetate 
• 443926-56-5 (2R,3S)-5,7-bis(benzyloxy)-2-(3',4'-dimethoxyphenyl)chroman-3-ol 
• 443926-53-2 (2R,3S)-5,7-diacetoxy-2-(3',4'-dimethoxyphenyl)chroman-3-yl acetate 
• 443926-54-3 (2R,3S)-3',4'-dimethoxyphenyl-5,7-dihydroxychroman-3-yl acetate 
• 94102-41-7 (2R,3S)-4-(3-hydroxy-5,7-dimethoxychroman-2-yl)benzene-1,2-diol 
• 69912-76-1 (2R,3S)-2-(3',4'-dimethoxyphenyl)chroman-3,5,7-triol 

Relevant academic research and scientific papers

New lipophenols prevent carbonyl and oxidative stresses involved in macular degeneration

Dry age-related macular degeneration and Stargardt disease undergo a known toxic mechanism caused by carbonyl and oxidative stresses (COS). This is responsible for accumulation in the retinal pigment epithelium (RPE) of A2E, a main toxic pyridinium bis-retinoid lipofuscin component. Previous studies have shown that carbonyl stress in retinal cells could be reduced by an alkyl-phloroglucinol-DHA conjugate (lipophenol). Here, we performed a rational design of different families of lipophenols to conserve anti-carbonyl stress activities and improve antioxidant properties. Five synthetic pathways leading to alkyl-(poly)phenol derivatives, with phloroglucinol, resveratrol, catechin and quercetin as the main backbone, linked to poly-unsaturated fatty acid, are presented. These lipophenols were evaluated in ARPE-19 cell line for their anti-COS properties and a structure-activity relationship study is proposed. Protection of ARPE-19 cells against A2E toxicity was assessed for the four best candidates. Finally, interesting anti-COS properties of the most promising quercetin lipophenol were confirmed in primary RPE cells.

LIPOPHENOLIC FLAVONOID DERIVATIVES USEFUL TO REDUCE CARBONYL AND OXIDATIVE STRESSES (COS)

The invention relates to compound of formula (I): in particular flavonoid derivatives (quercetin and catechin derivatives), for use in the prevention and/or the treatment of a disease or disorder involving both carbonyl and oxidative stresses.

Antiplasmodial phenolic compounds from Piptadenia pervillei

Piptadenia pervillei Vatke (Fabaceae) was selected from a screening programme devoted to the search of naturally-occuring antimalarial compounds from plants of Madagascar. Bioassay-guided fractionation of the ethyl acetate extract of the leaves led to the isolation of four phenolic compounds, (+)-catechin (1), (+)-catechin 5-gallate (2), (+)-catechin 3-gallate (3) and ethyl gallate (4). Structures were determined by NMR and mass spectroscopy. Compounds 2 and 3 displayed the highest in vitro activity against the chloroquine-resistant strain FcB1 of Plasmodium falciparum with IC50 values of 1.2 μM and 1.0 μM, respectively, and no significant cytotoxicity against the human embryonic lung cells MRC-5 was measured (IC50 values > 75 μM). Five analogues (5-9) of (+)-catechin 5-gallate (2) were synthesized and evaluated for their antiplasmodial activity. Georg Thieme Verlag KG Stuttgart.

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.