89946-06-5

Basic information

• Product Name: (E)-3,5,4'-Tribenzyloxystilbene
• Synonyms: (E)-3,5,4'-Tribenzyloxystilbene;1,3-bis(phenylmethoxy)-5-[2-(4-phenylmethoxyphenyl)ethenyl]benzene;1,3-bis(phenylmethoxy)-5-[(E)-2-(4-phenylmethoxyphenyl)ethenyl]benzene
• CAS NO: 89946-06-5
• Molecular Formula: C₃₅H₃₀O₃
• Molecular Weight: 498.6109
• EINECS: 1312995-182-4
• Mol File: 89946-06-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (E)-3,5,4'-Tribenzyloxystilbene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3,5,4'-Tribenzyloxystilbene(89946-06-5)
• EPA Substance Registry System: (E)-3,5,4'-Tribenzyloxystilbene(89946-06-5)

Safety Data

• Hazardous Substances Data: 89946-06-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(E)-3,5,4'-Tribenzyloxystilbene is used as a pharmaceutical agent for its potential health benefits. It is known to be a specific inhibitor of COX-1, an enzyme involved in inflammation and pain, and also inhibits the hydroperoxidase activity of COX-1. (E)-3,5,4'-Tribenzyloxystilbene has been shown to inhibit events associated with tumor initiation, promotion, and progression, making it a potential candidate for cancer prevention and treatment.
Used in Food Industry:
(E)-3,5,4'-Tribenzyloxystilbene is used as a functional ingredient in the food industry due to its correlation with serum lipid reduction and inhibition of platelet aggregation. These properties can contribute to the development of health-promoting food products and supplements that may help in maintaining cardiovascular health and preventing related diseases.

Upstream product

• 4397-53-9 p-benzyloxybenzaldehyde 
• 24082-43-7 [3,5-di(benzyloxy)benzyl]triphenylphosphonium bromide 
• 355407-54-4 (3,5-bis-benzyloxy-benzyl)-phosphonic acid diisopropyl ester 
• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 
• 100-39-0 benzyl bromide 
• 512807-90-8 3,4',5-tribenzyloxydibenzylsulfone 
• 7440-44-0 pyrographite 
• 33617-49-1 diethyl <3,5-bis(benzyloxy)benzyl>phosphonate 
• 5544-60-5 4-(benzyloxy)benzyl bromide 
• 58605-10-0 methyl 3,5-bis(benzyloxy)benzoate 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 836-43-1 4-benzyloxybenzyl alcohol 
• 50513-72-9 (3,5-di-benzyloxy)benzoic acid benzyl ester 
• 24131-32-6 3,5-bis(benzyloxy)benzyl bromide 

Downstream Products

• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 

Relevant articles and documents

NOVEL 1,2-DIPHENYLETHYLENE GLYCOL COMPOUNDS FOR COMBATING AGING OF THE SKIN, AND COSMETIC USE THEREOF

The present invention relates to novel compounds of formula (I) to cosmetic compositions comprising same, and also to the use thereof for preventing and/or cosmetically treating the signs of aging of the skin.

Syntheses of resveratrol and its hydroxylated derivatives as radical scavenger and tyrosinase inhibitor

Eight hydroxylated stilbene derivatives including resveratrol, desoxyrhapontigenin and piceatannol as potential radical scavenger and tyrosinase inhibitor are synthesized using optimized Wittig-Horner reaction for excellent trans-selectivity in good yields. Antioxidant activity was tested against ABTS radical and tyrosinase inhibitory activity was performed with L-tyrosine as the substrate based on previous procedure with some modification. In general, catecholic stilbenes showed stronger activity against ABTS radical and resorcinolic moiety showed stronger tyrosinase inhibitory activity. Synthetic piceatannol which containing both catecholic and resorcinolic moieties showed the strongest activity in both as ABTS radical scavenger and tyrosinase inhibitor with IC50 values of 4.1 and 8.6 μM, respectively.

NOVEL PROCESS FOR THE SYNTHESIS OF (E)-STILBENE DERIVATIVES WHICH MAKES IT POSSIBLE TO OBTAIN RESVERATROL AND PICEATANNOL

A subject-matter of the present invention is a novel process for the synthesis of (E)- stilbene derivatives targeted at obtaining in particular resveratrol and piceatannol.

Resveratrol Derivatives and Their Role as Potassium Channels Modulators

A series of stilbenoid analogues of resveratrol (trans-3,4′ ,5-trihydroxystilbene) with a stilbenic or a bibenzylic skeleton have been prepared by partial synthesis from resveratrol and dihydroresveratrol. The synthesized compounds have been evaluated for their ability to modulate voltage-gated channels.

Synthesis of resveratrol using a direct decarbonylative Heck approach from resorcylic acid

The phytoalexin resveratrol has been made using a decarbonylative Heck reaction. The acid chloride derived from 3,5-dihydroxybenzoic acid was coupled with 4-acetoxystyrene in the presence of palladium acetate and N,N-bis-(2,6-diisopropylphenyl)dihydroimidazolium chloride to give the substituted stilbene in 73% yield as the key step.

Stereoselective route to produce tris-O-substituted-(E)-1-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)ethene, an intermediate in the synthesis of trans-resveratrol

The present invention relates to a new stereoselective method for the preparation of tris-O-substituted-(E)-1-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)ethene derivative of the formula (I) which is a key intermediate in the synthesis of trans-resveratrol (

Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents

Resveratrol 1 (3,4′,5-trihydroxy-trans-stilbene), a phytoalexin present in grapes and other food products, has recently been suggested as a potential cancer chemopreventive agent based on its striking inhibitory effects on cellular events associated with cancer initiation, promotion, and progression. This triphenolic stilbene has also displayed in vitro growth inhibition in a number of human cancer cell lines. In this context, a series of cis- and trans-stilbene-based resveratrols were prepared with the aim of discovering new lead compounds with clinical potential. All the synthesized compounds were tested in vitro for cell growth inhibition and the ability to induce apoptosis in HL60 promyelocytic leukemia cells. The tested trans-stilbene derivatives were less potent than their corresponding cis isomers, except for trans-resveratrol, whose cis isomer was less active. The best results were obtained with compounds 11b and 7b, the cis-3,5-dimethoxy derivatives of rhapontigenin 10a (3,5,3′-trihydroxy-4′methoxy-transstilbene) and its 3′-amino derivative 10b, respectively, which showed apoptotic activity at nanomolar concentrations. The corresponding trans isomers 12b and 8b were less active both as antiproliferative and as apoptosis-inducing agents. Of interest, 11b and 7b were active toward resistant HL60R cells and their activity was higher than that of several classic chemotherapeutic agents. The flow cytometry assay showed that at 50 nM compounds 7b or 11b were able to recruit almost all cells in the apoptotic sub-G0-G1 peek, thus suggesting that the main mechanism of cytotoxicity of these compounds could be the activation of apoptosis. These data indicate unambiguously that structural alteration of the stilbene motif of resveratrol can be extremely effective in producing potent apoptosis-inducing agents.

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.