116973-12-7

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 2-[3,4-bis(phenylmethoxy)phenyl]-3-hydroxy-5,7-bis(phenylmethoxy)-
• CAS NO: 116973-12-7
• Molecular Formula: C43H34O7
• Molecular Weight: 662.739
• Mol File: 116973-12-7.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 2-[3,4-bis(phenylmethoxy)phenyl]-3-hydroxy-5,7-bis(phenylmethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 2-[3,4-bis(phenylmethoxy)phenyl]-3-hydroxy-5,7-bis(phenylmethoxy)-(116973-12-7)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 2-[3,4-bis(phenylmethoxy)phenyl]-3-hydroxy-5,7-bis(phenylmethoxy)-(116973-12-7)

Safety Data

• Hazardous Substances Data: 116973-12-7(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 153-18-4 rutin 

Downstream Products

• 1332833-27-8 5,7-bisbenzyloxy-2-(3,4-bisbenzyloxyphenyl)-3-(β-D-glucopyranosyloxy)-4H-chromen-4-one 
• 22688-79-5 quercetin 3-O-β-D-glucuronopyranoside 
• 1332833-26-7 C₅₇H₅₂O₁₆ 
• 1420045-11-9 3-O-[(3″,4″,5″-tri-O-methoxymethyl)-galloyl]quercetin 
• 700364-44-9 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 3,4,5-trihydroxybenzoate 
• 1420045-10-8 C₅₆H₅₀O₁₄ 
• 1612925-23-1 C₄₅H₃₆O₈ 
• 1486-70-0 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-3-methoxy-chromen-4-on 
• 33429-83-3 3,4'-O-dimethylquercetin 
• 2068-02-2 2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxychromen-4-one 
• 572-32-7 ayanin 
• 143631-97-4 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-ylacetate 
• 39028-59-6 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-3',4',5,7-tetrahydroxyflavonol 

Relevant articles and documents

An expeditious synthesis of quercetin 3-O-β-d-glucuronide from rutin

We report the synthesis of the major human metabolite of quercetin, quercetin 3-O-β-d-glucuronide, from rutin (quercetin-3-rutinoside), which is commercially available at low cost. This straightforward synthesis is based on the key intermediate 3′,4′,5,7-tetra-O-benzyl-quercetin which is obtained in only two steps by the total benzylation of rutin followed by acid hydrolysis of the rutinoside residue. Glycosylation of the free 3 hydroxyl group by 1-bromo-3,4,6-tetra-O-acetyl-α-d-glucopyranoside yields the protected glucoside. TEMPO-mediated oxidation of primary alcohol on the deprotected glucoside gives access to the benzylated glucuronide. Removal of the benzyl groups which protect the quercetin hydroxyl groups by H2 (10% Pd/C) yields quercetin 3-O-β-d-glucuronide.

Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement

Stereoselective glycosylation is challenging in carbohydrate chemistry. Herein, stereoselective thioglycosylation of glycals via palladium-catalyzed allylic rearrangement yields various substituents on α-isomer thioglycosides. Two comprehensive series of aryl and benzyl thioglycosides were obtained via a combination of thiosulfates with glycals derived from glucose, arabinose, galactose, and rhamnose. Furthermore, diosgenyl α-l-rhamnoside and isoquercitrin achieved selectivity via stereospecific [2,3]-sigma rearrangements of α-sulfoxide-rhamnoside and α-sulfoxide-glucoside, respectively.

The first synthesis of 3-O-methylcyanidin and the effect of 3-O-substitution on stability under acidic conditions

The simplest and most common anthocyanin in nature is 3-O-glucosylcyanidin (1), and 3-O-glucosylation is believed to stabilize the chromophore. To clarify the effect of the glucose residue we compared the stability of 1 with its aglycone, cyanidin (2), an