A stilbene polyphenol with diverse biological activities
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trans-ε-Viniferin

Item No. 25737

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-[(2R,3R)-2,3-dihydro-6-hydroxy-2-(4-hydroxyphenyl)-4-[(1E)-2-(4-hydroxyphenyl)ethenyl]-3-benzofuranyl]-1,3-benzenediol
CAS Number
62218-08-0
Synonyms
  • (–)-ε-Viniferin
Molecular Formula
C28H22O6
Formula Weight
454.5
Purity
≥90%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
λmax
226, 326 nm
SMILES
OC1=CC(/C=C/C2=CC=C(O)C=C2)=C3C(O[C@@H](C4=CC=C(O)C=C4)[C@@H]3C5=CC(O)=CC(O)=C5)=C1
InChi Code
InChI=1S/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
InChi Key
FQWLMRXWKZGLFI-YVYUXZJTSA-N
Origin
Plant/Vitis amurensis
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $69

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    1 mg

    $127

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    trans-ε-Viniferin is a stilbene polyphenol and dimer of trans-resveratrol (Item No. 70675) that has been found in various red wines and has diverse biological activities.1,2,3,4,5 It induces disaggregation of aggregated amyloid-β (1-42) (Aβ42; Item No. 20574) 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.2 trans-ε-Viniferin reduces cytotoxicity induced by truncated huntingtin (Htt) in PC12 cells (EC50 = 30 nM).3 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).4 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.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Vitrac, X., Bornet, A., Vanderlinde, R., et al. Determination of stilbenes (δ-viniferin, trans-astringin, trans-piceid, cis- and trans-resveratrol, ε-viniferin) in Brazilian wines. J. Agric. Food Chem. 53(14), 5664-5669 (2005).

    2. Vion, E., Page, G., Bourdeaud, E., et al. Trans ε-viniferin is an amyloid-β disaggregating and anti-inflammatory drug in a mouse primary cellular model of Alzheimer’s disease. Mol. Cell Neurosci. 88, 1-6 (2018).

    3. Fu, J., Jin, J., Cichewicz, R.H., et al. trans-(−)-ε-Viniferin increases mitochondrial sirtuin 3 (SIRT3), activates AMP-activated protein kinase (AMPK), and protects cells in models of Huntington Disease. The Journal of Biological Chemisty 287(29), 24460-24472 (2012).

    4. Yu, B., Jiang, Y., Zhang, B., et al. Resveratrol dimer trans-ε-viniferin prevents rotaviral diarrhea in mice by inhibition of the intestinal calcium-activated chloride channel. Pharmacol. Res. 129, 453-461 (2018).

    5. Ohara, K., Kusano, K., Kitao, S., et al. ε-Viniferin, a resveratrol dimer, prevents diet-induced obesity in mice. Biochem. Biophys. Res. Commun. 468(4), 877-882 (2015).

    Product Citations

    Ohara, K., Kusano, K., Kitao, S., et al. ε-Viniferin, a resveratrol dimer, prevents diet-induced obesity in mice. Biochem. Biophys. Res. Commun. 468(4), 877-882 (2015).