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epsilon-viniferin

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epsilon-viniferin 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
  • (-)-trans-epsilon-viniferin
CAS:
62218-08-0
MF:
C28H22O6
MW:
454.47
Mol File:
62218-08-0.mol
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epsilon-viniferin Chemical Properties

Melting point:
approximate 157℃ (dec.)
storage temp. 
Store at -20°C
solubility 
Soluble in methanol;
form 
Powder
color 
Off-white to gray
Water Solubility 
sparingly soluble in water
LogP
3.802 (est)
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epsilon-viniferin Usage And Synthesis

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.

Definition

ChEBI: (-)-trans-epsilon-viniferin is a stilbenoid that is the (-)-trans-stereoisomer of epsilon-viniferin, obtained by cyclodimerisation of trans-resveratrol. It has a role as a metabolite. It is a member of 1-benzofurans, a polyphenol and a stilbenoid. It is functionally related to a trans-resveratrol. It is an enantiomer of a (+)-trans-epsilon-viniferin.

target

5-HT Receptor | MAO | Antifection

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