MedKoo Cat#: 574025 | Name: trans-ε-Viniferin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

trans-ε-Viniferin is a stilbene polyphenol and dimer of trans-resveratrol that has been found in various red wines. It induces disaggregation of aggregated amyloid-β (1-42) (Aβ42) fibrils 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. 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. In vivo, trans-ε-viniferin 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.

Chemical Structure

trans-ε-Viniferin
trans-ε-Viniferin
CAS#62218-08-0

Theoretical Analysis

MedKoo Cat#: 574025

Name: trans-ε-Viniferin

CAS#: 62218-08-0

Chemical Formula: C28H22O6

Exact Mass: 454.1416

Molecular Weight: 454.48

Elemental Analysis: C, 74.00; H, 4.88; O, 21.12

Price and Availability

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1mg USD 275.00
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Synonym
(–)-ε-Viniferin, ε-Viniferin, trans-ε-Viniferin
IUPAC/Chemical Name
5-[(2R,3R)-2,3-dihydro-6-hydroxy-2-(4-hydroxyphenyl)-4-[(1E)-2-(4-hydroxyphenyl)ethenyl]-3-benzofuranyl]-1,3-benzenediol
InChi Key
FQWLMRXWKZGLFI-YVYUXZJTSA-N
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
SMILES Code
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
Appearance
Solid powder
Purity
>90% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
λmax: 226, 326 nm

Preparing Stock Solutions

The following data is based on the product molecular weight 454.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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. J. Biol. Chem. 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. Bioph. 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. Bioph. Res. Commun. 468(4), 877-882 (2015).