197440-96-3

Basic information

• Product Name: (E)-5-hydroxy-4'-methoxy-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)stilbene
• Synonyms: (E)-5-hydroxy-4'-methoxy-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)stilbene
• CAS NO: 197440-96-3
• Molecular Weight: 572.566
• Mol File: 197440-96-3.mol

Chemical Properties

• CAS DataBase Reference: (E)-5-hydroxy-4'-methoxy-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)stilbene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-5-hydroxy-4'-methoxy-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)stilbene(197440-96-3)
• EPA Substance Registry System: (E)-5-hydroxy-4'-methoxy-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)stilbene(197440-96-3)

Safety Data

• Hazardous Substances Data: 197440-96-3(Hazardous Substances Data)

Upstream product

• 65728-21-4 5-[(E)-2-(4-methoxyphenyl)vinyl]benzene-1,3-diol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 21960-26-9 (4-methoxybenzylidene)triphenylphosphorane 
• 824-94-2 p-methoxybenzyl chloride 
• 187803-40-3 3,5-bis(tert-butyldimethylsilyloxy)benzaldehyde 
• 3462-97-3 (4-methoxybenzyl)triphenylphosphonium bromide 
• 26153-38-8 3,5-dihydroxybenzaldehyde 

Downstream Products

• 30197-14-9 (E)-3-(β-D-glucopyranosyloxy)-5-hydroxy-4'-methoxystilbene 
• 27208-80-6 polydatin 

Relevant articles and documents

Synthesis of biologically active polyphenolic glycosides (combretastatin and resveratrol series)

(E)-3-(β-D-Glucopyranosyloxy)-4',5-dihydroxystilbene (resveratrol 3-β-D-glucoside, piceid), (Z)-2',3'-dihydroxy-3,4,4',5-tetramethoxystilbene (combretastatin A-1), (Z)-3'-hydroxy-3,4,4', 5-tetramethoxystilbene (combretastatin A-4), (Z)-2'-hydroxy-3,4,4',5-tetramethoxystilbene (combretastatin iso-A-4), α,β-dihydro-2',3'-dihydroxy-3,4,4',5-tetramethoxystilbene (combretastatin B-1), the corresponding glucosides, and related compounds have been synthesized via Wittig reactions followed by,glucosylation under phase-transfer catalysis. Most of the compounds synthesized have been tested with respect to biological activity (cytostatic, cytotoxic, antimitotic, neurotoxic, antiplatelet aggregation activity).

Isolation, synthesis, and antiplatelet aggregation activity of resveratrol 3-O-β-D-glucopyranoside and related compounds

Resveratrol 3-O-β-D-glucopyranoside (1) has been isolated from the seeds of Erythrophleum lasianthum (Caesalpinioidae, Leguminosae), a South African plant used in traditional medicine, and has shown antiplatelet aggregation activity. The synthesis of 1, related hydroxystilbenes, and their glucosides has been undertaken to provide larger quantities, for further biological evaluation, and has been accomplished via Wittig reactions followed by glucosylation under phase transfer catalysis.