62218-08-0

Basic information

• Product Name: epsilon-viniferin
• Synonyms: epsilon-viniferin;(-)-5-[[(2R)-2,3-Dihydro-6-hydroxy-2β-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)vinyl]benzofuran]-3α-yl]-1,3-benzenediol;(2R)-2β-(4-Hydroxyphenyl)-3α-(3,5-dihydroxyphenyl)-4-(4-hydroxy-trans-styryl)-2,3-dihydrobenzofuran-6-ol;(2R)-2β-(4-Hydroxyphenyl)-3α-(3,5-dihydroxyphenyl)-4-[(E)-4-hydroxystyryl]-2,3-dihydrobenzofuran-6-ol;[2R,(-)]-2β-(4-Hydroxyphenyl)-3α-(3,5-dihydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydrobenzofuran-6-ol;5-[(2R,3R)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydrobenzofuran-3-yl]benzene-1,3-diol;e-viniferin;epsilion-Viniferin
• CAS NO: 62218-08-0
• Molecular Formula: C₂₈H₂₂O₆
• Molecular Weight: 454.47068
• Mol File: 62218-08-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: approximate 157℃ (dec.)
• Boiling Point: 694.8°Cat760mmHg
• Flash Point: 374°C
• Appearance: /
• Density: 1.45g/cm³
• Vapor Pressure: 6.04E-20mmHg at 25°C
• Refractive Index: 1.777
• CAS DataBase Reference: epsilon-viniferin(CAS DataBase Reference)
• NIST Chemistry Reference: epsilon-viniferin(62218-08-0)
• EPA Substance Registry System: epsilon-viniferin(62218-08-0)

Safety Data

• Hazardous Substances Data: 62218-08-0(Hazardous Substances Data)

Usage

Description

trans-ε-Viniferin is a stilbene polyphenol and dimer of trans-resveratrol that has been found in various red wines and has diverse biological activities. It induces disaggregation of aggregated amyloid-β (1-42) (Aβ42; ) fibrils in a cell-free assay and decreases Aβ42- and IL-1β-induced release of TNF-α and IL-6 in primary mouse neuron and astrocyte cocultures. trans-ε-Viniferin reduces cytotoxicity induced by truncated huntingtin (Htt) in PC12 cells (EC50 = 30 nM). It also reduces production of reactive oxygen species (ROS), mitochondrial dysfunction, and PGC-1α depletion and increases protein levels and deacetylase activity of sirtuin 3 (SIRT3) in cells expressing mutant Htt. trans-ε-Viniferin inhibits calcium-activated chloride channel currents in HT-29 cells (IC50 = ~1 μM). In vivo, trans-ε-viniferin (2 μg per animal) reduces rotavirus-induced secretory diarrhea in mice without affecting the rotaviral infection. Dietary administration of trans-ε-viniferin reduces hepatic triglyceride accumulation and body weight increases in a mouse model of diet-induced obesity.

Uses

ε-Viniferin is a stilbene extract posessing cytotoxic effects and may contain anti-cancer properties.

InChI:InChI=1/C28H22O6/c29-20-7-2-16(3-8-20)1-4-18-11-24(33)15-25-26(18)27(19-12-22(31)14-23(32)13-19)28(34-25)17-5-9-21(30)10-6-17/h1-15,27-33H/b4-1+/t27-,28+/m1/s1

Upstream product

• 253435-07-3 (E)-5-((±)-6-hydroxy-2-(4-hydroxyphenyl)-4-(4-hydroxystyryl)-2,3-dihydrobenzofuran-3-yl)benzene-1,3-diol 
• 1246746-89-3 1-(β-D-glucopyranosyloxy)-5-{(2R,3R)-6-(β-glucopyranosyloxy)-2-(4-hydroxyphenyl)-4-[(E)-4-hydroxystyryl]-2,3-dihydrobenzofuran-3-yl}benzene-3-ol 
• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 

Downstream Products

• 253435-07-3 cis ε-viniferine 
• 253435-07-3 (+)-cis-ε-viniferin 
• 223591-26-2 viniferifuran 
• 1527502-97-1 C₂₁H₁₆O₂ 
• 1527502-99-3 C₂₈H₂₂O 
• 1527503-02-1 C₃₃H₁₇F₁₅O₁₆S₅ 
• 1228291-62-0 resviniferin A 
• 1228291-64-2 resviniferin B 

Relevant articles and documents

Inhibition of Pancreatic α-amylase by Resveratrol Derivatives: Biological activity and molecular modelling evidence for cooperativity between viniferin enantiomers

To improve the current understanding of the role of stilbenoids in the management of diabetes, the inhibition of the pancreatic α-amylase by resveratrol derivatives was investigated. To approach in a systematic way, the mechanistic and structural aspects of the interaction, potential bioactive agents were prepared as single molecules, that were used for the biological evaluation of the determinants of inhibitory binding. Some dimeric stilbenoids—in particular, viniferin isomers— were found to be better than the reference drug acarbose in inhibiting the pancreatic α-amylase. Racemic mixtures of viniferins were more effective inhibitors than the respective isolated pure enantiomers at an equivalent total concentration, and displayed cooperative effects not observed with the individual enantiomers. The molecular docking analysis provided a thermodynamics-based rationale for the measured inhibitory ability and for the observed synergistic effects. Indeed, the binding of additional ligands on the surface of the alpha-amylase was found to decrease the dissociation constant of inhibitors bound to the active site of the enzyme, thus providing a mechanistic rationale for the observed inhibitory synergies.

Applications of Amurensin H derivatives in treating and prevention liver related diseases

The invention discloses applications of Amurensin H derivatives shown as a formula (I) and (II) and pharmaceutically acceptable salt thereof in the preparation of drugs for treating and/or preventingliver related diseases, and also discloses the preparation method of a compound, and applications of the pharmaceutical composition of the compound in the preparation of the drugs for treating and/orpreventing the liver related diseases.

A joint experimental and theoretical investigation on the oxidative coupling of resveratrol induced by copper and iron ions

Currently, a mounting interest exists on the biological activity of polyphenolic compounds, which have been suggested to exert positive effects on the human health. In this paper we report the first electrospray ionization mass spectrometry (ESI-MS) study on the gas-phase production of isomeric δ-viniferin and ε-viniferin dimers in racemic form, starting from acetonitrile/water solutions containing resveratrol and CuSO4 or FeCl3, respectively. Interestingly, the formation of racemic δ-viniferin dehydrodimer is observed in ESI-MS experiments carried out on resveratrol-copper mixtures, while the analogous resveratrol-iron reaction affords the racemic ε-viniferin dehydrodimer. The use of gas-phase techniques and of ab initio calculations, at BHandHLYP/LACV3P + +** level of theory, allowed us to elucidate some important aspects of these reaction mechanisms. In particular, a different stability for the resveratrol radicals involved in the oxidative coupling has been obtained in the presence of copper ion, favoring the formation of δ-viniferin, as proposed for the in vivo mechanism where copper is able to switch the resveratrol from an antioxidant to a prooxidant agent. Finally, the structure-reactivity relationship has been investigated for synthetic analogues of resveratrol, showing the crucial role of the OH group in para position.