33626-09-4

Basic information

• Product Name: (E)-3,3',5,5'-tetrahydroxystilbene
• Synonyms: (E)-3,3',5,5'-tetrahydroxystilbene
• CAS NO: 33626-09-4
• Molecular Weight: 244.247
• Mol File: 33626-09-4.mol

Chemical Properties

• CAS DataBase Reference: (E)-3,3',5,5'-tetrahydroxystilbene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3,3',5,5'-tetrahydroxystilbene(33626-09-4)
• EPA Substance Registry System: (E)-3,3',5,5'-tetrahydroxystilbene(33626-09-4)

Safety Data

• Hazardous Substances Data: 33626-09-4(Hazardous Substances Data)

Upstream product

• 80715-09-9 (E)-3,3',5,5'-tetramethoxystilbene 
• 150258-79-0 (E)-1-<3,5-bis(benzyloxy)phenyl>-2-<3,5-bis(benzyloxy)phenyl>ethene 
• 7786-61-0 3-methoxy-4-hydroxystyrene 
• 113231-14-4 1,3-dihydroxy-5-vinylbenzene 
• 2628-17-3 4-Vinylphenol 
• 877-88-3 3,5-dimethoxybenzyl bromide 
• 108957-75-1 diethyl 3,5-dimethoxybenzylphosphonate 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 14615-72-6 3,5-dibenzyloxybenzaldehyde 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 58605-10-0 methyl 3,5-bis(benzyloxy)benzoate 
• 24131-31-5 3,5-dibenzyloxybenzyl alcohol 
• 24131-32-6 3,5-bis(benzyloxy)benzyl bromide 
• 33617-49-1 diethyl <3,5-bis(benzyloxy)benzyl>phosphonate 

Downstream Products

• 150258-79-0 (E)-1-<3,5-bis(benzyloxy)phenyl>-2-<3,5-bis(benzyloxy)phenyl>ethene 
• 69026-25-1 7-hydroxy-5-(1-methyl-4-phenylbutoxy)phthalide 
• 69025-77-0 2,3-dihydro-5-(hydroxymethyl)-2,2-dimethyl-7-(1-methyl-4-phenylbutoxy)-4H-1-benzopyran-4-one 
• 69025-76-9 2,3-dihydro-2,2-dimethyl-7-(1-methyl-4-phenylbutoxy)-4-oxo-2H-1-benzopyran-5-carboxaldehyde 
• 69025-78-1 2,3-dihydro-5-(hydroxymethyl)-3-(hydroxymethylene)-2,2-dimethyl-7-(1-methyl-4-phenylbutoxy)-4H-1-benzopyran-4-one 
• 129657-99-4 C₃₅H₃₈O₆ 
• 69025-75-8 5,5'-(1,2-ethenediyl)bis<2,3-dihydro-2,2-dimethyl-7-(1-methyl-4-phenylbutoxy)-4H-1-benzopyran-4-one> 
• 1383709-07-6 C₆₆H₆₈O₂₀ 

Relevant articles and documents

Intramolecular energy transfer and photoisomerization in stilbene dendrimers

Stilbene dendrimers with energy harvesting chromophores, such as naphthalene and benzophenone, have been prepared and their photochemical and photophysical properties have been examined. These dendrimers underwent trans-cis mutual photoisomerization on excitation of the core stilbene or the peripheral naphthalene and benzophenone chromophores through several energy transfer processes, and photophysical processes such as intersystem crossing finally resulted in cis-trans isomerization of the core stilbene.

Synthesis of?stilbene derivatives with inhibition of?SARS coronavirus replication

Stilbene derivatives have wide range of activities. In an effort to find other potential activities of this kind of compounds, 17 derivatives, including resveratrol, were synthesized. Twelve of them were evaluated for their antiviral potential against severe acute respiratory syndrome (SARS)-CoV-induced cytopathicity in Vero E6 cell culture. The result showed that SARS virus was totally inhibited by compounds 17 and 19 ( ≤ 0.5?mg?ml-1) and no significant cytotoxic effects were observed in vitro.

Stereoselective synthesis of (E)-hydroxystilbenoids by ruthenium-catalyzed cross-metathesis

An efficient and highly stereoselective synthetic procedure is reported for the construction of symmetrical and unsymmetrical (E)-polymethoxystilbene and (E)-polyhydroxystilbene derivatives. The strategy rests on a cross-metathesis reaction catalyzed by stable, well-defined (alkylidene)ruthenium complexes, in particular the second-generation Grubbs catalyst [RuCl2(=CHPh)(SIMes) (PCy3)] [SIMes = 1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2- ylidene]. The metathesis of unprotected phenolic styrenes is illustrated by the synthesis of the important phytoalexins (E)-3,4′,5-trihydroxystilbene (resveratrol) and (E)-3,3′,4,5′-tetrahydroxystilbene (piceatannol). Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

STILBENE DERIVATIVES AND THEIR USE IN MEDICAMENTS

The invention relates to stilbene derivatives of general formula (I), in which at least four of the substituents R1 to R6 do not represent hydrogen. The substituents are effective radical captors, anti-tumour active ingredients and s

Resveratrol analogues as selective cyclooxygenase-2 inhibitors: Synthesis and structure-activity relationship

A series of hydroxylated and methoxylated trans-stilbenes were synthesized and evaluated for their ability to inhibit COX-1 and COX-2. Some of the hydroxylated derivatives are highly selective COX-2 inhibitor with potency comparable or better than clinically established drugs. Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is found in grapes and various medical plants. Among cytotoxic, antifungal, antibacterial cardioprotective activity resveratrol also demonstrates non-selective cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) inhibition. In order to find more selective COX-2 inhibitors a series of methoxylated and hydroxylated resveratrol derivatives were synthesized and evaluated for their ability to inhibit both enzymes using in vitro inhibition assays for COX-1 and COX-2 by measuring PGE2 production. Hydroxylated but not methoxylated resveratrol derivatives showed a high rate of inhibition. The most potent resveratrol compounds were 3,3′,4′,5-tetra-trans-hydroxystilbene (COX-1: IC50 = 4.713, COX-2: IC50 = 0.0113 μM, selectivity index = 417.08) and 3,3′,4,4′,5,5′-hexa-hydroxy-trans-stilbene (COX-1: IC 50 = 0.748, COX-2: IC50 = 0.00104 μM, selectivity index = 719.23). Their selectivity index was in part higher than celecoxib, a selective COX-2 inhibitor already established on the market (COX-1: IC 50 = 19.026, COX-2: IC50 = 0.03482 μM, selectivity index = 546.41). Effect of structural parameters on COX-2 inhibition was evaluated by quantitative structure-activity relationship (QSAR) analysis and a high correlation was found with the topological surface area TPSA (r = 0.93). Docking studies on both COX-1 and COX-2 protein structures also revealed that hydroxylated but not methoxylated resveratrol analogues are able to bind to the previously identified binding sites of the enzymes. Hydroxylated resveratrol analogues therefore represent a novel class of highly selective COX-2 inhibitors and promising candidates for in vivo studies.

Photoisomerization of stilbene dendrimers: The need for a volume-conserving isomerization mechanism

Highly branched stilbene dendrimers were synthesized and their photochemical behavior was studied. Even the stilbene dendrimer with molecular weight over 6500 underwent transcis isomerization in the excited singlet state within the lifetime of 10 ns. The

Bis-, tris-, and tetrakis(squaraines) linked by stilbenoid scaffolds

The oligosquaraines 1-5, with stilbenoid scaffolds, were prepared by multistep syntheses in which the final steps consisted of condensation reactions between the semisquaric acid 21 and multiple resorcinols 12b-15b and 17b. The target compounds exhibit in

Evaluation of resveratrol derivatives as potential antioxidants and identification of a reaction product of resveratrol and 2,2-diphenyl-1- picryhydrazyl radical

Resveratrol (3,4',5-trihydroxy-trans-stilbene), an antioxidant from grapes, and five other polyhydroxystilbenes were synthesized. Their antioxidative properties were evaluated in two model systems [pure lipid oxidation using the Rancimat method and 2,2-diphenyl-1-picryhydrazyl (DPPH) free radical scavenging model.] 3,3',4,5'-Tetrahydroxystilbene, 3,3',4,5,5'- pentahydroxystilbene, and 3,4,4',5-tetrahydroxystilbene were found to be more active than resveratrol in both models. A dimer of resveratrol was identified as the major radical reaction product when resveratrol was reacted with DPPH radicals.

Synthesis and Protein-Tyrosine Kinase Inhibitory Activity of Polyhydroxylated Stilbene Analogues of Piceatannol

A series of hydroxylated trans-stilbene related to the antileukemic natural product trans-3,3',4,5'-tetrahydroxy stilbene (piceatannol) (1) has been prepared and tested for inhibition of the lymphoid cell lineage-specific protein-tyrosine kinase p56lck, which plays an important role in lymphocyte proliferation and immune function.A number of the analogues displayed enhanced enzyme inhibitory activity relative to the natural product.Reduction of the double bond bridging the two aromatic rings and benzylation of the phenolic hydroxyl groups was found to decrease activity significantly.The most potent compounds in the series proved to be trans-3,3',5,5'-tetrahydroxystilbene, trans-3,3',5-trihydroxystilbene, and trans-3,4,4'-trihydroxystilbene.

Synthesis and nematocidal activity of hydroxystilbenes

Various (E)-hydroxystilbenes were synthesized from (E)/(Z) mixtures of methoxystilbenes through a new (Z)-(E) isomerization method followed by demethylation. The nematocidal activity appears when methoxystilbenes are demethylated to hydroxystilbenes. For this activity, a hydroxy group at the C-2 or C-3 position is necessary. Thus, 2-hydroxy-, 3-hydroxy-, 2,6-dihydroxy-, 3,4-dihydroxy-, 3,5-dihydroxy-, 2,2'-dihydroxy-, 3,3'-dihydroxy-, 3,4'dihydroxy-, 2-hydroxy-4-methoxy-, 5-hydroxy-2-methoxy-, 2-hydroxy-6-methoxy-, 6-allyloxy-2-hydroxy-, 3-hydroxy-5-methoxy-, and 5-allyloxy-3-hydroxystilbenes showed rather potent nematocidal activity. The activity of 5-allyloxy-3-hydroxystilbene was the strongest [minimal lethal concentration (MLC) = 30 μM]. The activities of the (E) and (Z) isomers were comparable. The activities were also retained, though they were weaker, in the dihydro derivatives, hydroxybibenzyls.