192710-88-6

Basic information

• Product Name: (Z)-3,5-di-(tert-butyldimethylsilyloxy)-4'-methoxystilbene
• Synonyms: (Z)-3,5-di-(tert-butyldimethylsilyloxy)-4'-methoxystilbene
• CAS NO: 192710-88-6
• Molecular Weight: 470.8
• Mol File: 192710-88-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (Z)-3,5-di-(tert-butyldimethylsilyloxy)-4'-methoxystilbene(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-3,5-di-(tert-butyldimethylsilyloxy)-4'-methoxystilbene(192710-88-6)
• EPA Substance Registry System: (Z)-3,5-di-(tert-butyldimethylsilyloxy)-4'-methoxystilbene(192710-88-6)

Safety Data

• Hazardous Substances Data: 192710-88-6(Hazardous Substances Data)

Upstream product

• 3462-97-3 (4-methoxybenzyl)triphenylphosphonium bromide 
• 187803-40-3 3,5-bis(tert-butyldimethylsilyloxy)benzaldehyde 
• 1530-38-7 ((4-methoxyphenyl)methyl)triphenylphosphonium bromide 
• 26153-38-8 3,5-dihydroxybenzaldehyde 
• 2746-25-0 p-Methoxybenzyl bromide 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 105-13-5 4-Methoxybenzyl alcohol 
• 824-94-2 p-methoxybenzyl chloride 
• 103929-83-5 methyl 3,5-bis(tert-butyldimethylsilyloxy)benzoate 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 103929-84-6 [3,5-di(tert-butyldimethylsilanyloxy)phenyl]methanol 
• 99-10-5 3,5-Dihydroxybenzoic acid 

Downstream Products

• 192710-89-7 cis-5-(4-methoxystyryl)benzene-1,3-diol 
• 192710-87-5 (E)-3,5-di-(tert-butyldimethylsilyloxy)-4'-methoxystilbene 
• 65728-21-4 5-[(E)-2-(4-methoxyphenyl)vinyl]benzene-1,3-diol 

Relevant articles and documents

Unexpected O-alkylation and ester migration in phenolic 2,3-diaryl-2,3-dihydrobenzo[b]furans

O-alkylation of 2-(4-methoxyphenyl)-5-hydroxy-3-[1,3-phenylene-bis(4- nitrobenzoate)]-2,3-dihydrobenzo[b]furan results in the unexpected hydrolysis of the nitrobenzoate esters, transfer of a 4-nitrobenzoic acid group to the 5-hydroxyl group and double alkylation of the newly formed 3,5-diphenol moiety. A range of alkyl halides can be used and give access to O-alkyl analogues of -viniferin.

Quinone reductase induction activity of methoxylated analogues of resveratrol

Agents that induce the activity of phase II enzymes play an important role in intervening with the carcinogenic process at the initiation stage. Resveratrol is well known for its chemopreventive activity against major stages of carcinogenesis. In this study, several methoxylated analogues of resveratrol were synthesized and evaluated for their ability to induce the activity of the phase II enzyme quinone reductase (QR). Methoxy groups serve to increase lipophilicity and improve metabolic stability. Compared to resveratrol, analogues with ortho-methoxy substituents were found to be more potent inducers of QR and to exert their activity in a qualitatively different manner. The greater induction activities associated with these stilbenoids serve as a useful starting point for the design of improved chemopreventive agents.

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).