EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

epsilon-viniferin
1,3-benzenediol, 5-(2,3-dihydro-6-hydroxy-2(4-hydroxyphenyl)4-(2-(4-hydroxyphenyl)ethenyl)-3-benzofuranyl)-

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CAS Number: 62218-08-0Picture of molecule3D/inchi
FDA UNII: 0K8Z2K6Y7O
Nikkaji Web:J957.611H
XlogP3-AA:5.40 (est)
Molecular Weight:454.47854000
Formula:C28 H22 O6
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 694.00 to 695.00 °C. @ 760.00 mm Hg (est)
Flash Point: 705.00 °F. TCC ( 374.00 °C. ) (est)
logP (o/w): 3.802 (est)
Soluble in:
 water, 0.1319 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
epsilon-Viniferin 0.96
Odor: characteristic
Use: î-Viniferin isolated form the stem of Gnetum montanum Markgr. enzyme inhibitor
Carbosynth
For experimental / research use only.
(-)-e-Viniferin
Coompo
For experimental / research use only.
epsilon-Viniferin from Plants ≥96%
Odor: characteristic
Use: Epsilon-viniferin shows a human cytochrome P450 enzymes inhition activity. Epsilon-viniferin and epsilon-viniferin pentaacetate slightly reduce cell proliferation but might protect from cell degenerescence.
ExtraSynthese
For experimental / research use only.
trans-epsilon-Viniferin
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for epsilon-viniferin usage levels up to:
 not for fragrance use.
 
Recommendation for epsilon-viniferin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5281728
National Institute of Allergy and Infectious Diseases:Data
(3R)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
Chemidplus:0062218080
 
References:
 (3R)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5281728
Pubchem (sid):135191966
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C10289
HMDB (The Human Metabolome Database):HMDB30604
FooDB:FDB002498
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 grape leaf
Search Trop Picture
 wine
Search Picture
 
Synonyms:
1,3-benzenediol, 5-(2,3-dihydro-6-hydroxy-2(4-hydroxyphenyl)4-(2-(4-hydroxyphenyl)ethenyl)-3-benzofuranyl)-
(3R)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
 

Articles:

PubMed:Composition and Tissue-Specific Distribution of Stilbenoids in Grape Canes Are Affected by Downy Mildew Pressure in the Vineyard.
J-Stage:Greater Effectiveness of e-Viniferin in Red Wine Than Its Monomer Resveratrol for Inhibiting Vascular Smooth Muscle Cell Proliferation and Migration
PubMed:Direct and protective effects of single or combined addition of vincristine and ε-viniferin on human HepG2 cellular oxidative stress markers in vitro.
PubMed:Synthesis of ε-Viniferin Glycosides by Glucosyltransferase from Phytolacca americana and their Inhibitory Activity on Histamine Release from Rat Peritoneal Mast Cells.
PubMed:Various extraction methods for obtaining stilbenes from grape cane of Vitis vinifera L.
PubMed:Direct identification and characterization of phenolic compounds from crude extracts of buds and internodes of grapevine (Vitis vinifera cv Merlot).
PubMed:Response of direct or priming defense against Botrytis cinerea to methyl jasmonate treatment at different concentrations in grape berries.
PubMed:Investigation of the absorption of resveratrol oligomers in the Caco-2 cellular model of intestinal absorption.
PubMed:A Huge PVDF Adsorption Difference Between Resveratrol and ε-Viniferin Allows to Quantitatively Purify Them and to Assess Their Anti-Tyrosinase Property.
PubMed:A new symmetrical tetramer oligostilbenoid containing tetrahydrofuran ring from the stem bark of Dryobalanops lanceolata.
PubMed:Antifungal activity of resveratrol derivatives against Candida species.
PubMed:Bacteriostatic antimicrobial combination: antagonistic interaction between epsilon-viniferin and vancomycin against methicillin-resistant Staphylococcus aureus.
PubMed:Identification of resveratrol oligomers as inhibitors of cystic fibrosis transmembrane conductance regulator by high-throughput screening of natural products from chinese medicinal plants.
PubMed:Influence of post-pruning storage on stilbenoid levels in Vitis vinifera L. canes.
PubMed:Preharvest methyl jasmonate and postharvest UVC treatments: increasing stilbenes in wine.
PubMed:Two new oligostilbenes from the stem of Parthenocissus quinquefolia.
PubMed:Resveratrol oligomers inhibit biofilm formation of Escherichia coli O157:H7 and Pseudomonas aeruginosa.
PubMed:Topoisomerase II-targeting properties of a grapevine-shoot extract and resveratrol oligomers.
PubMed:Towards novel anti-tumor strategies for hepatic cancer: É›-viniferin in combination with vincristine displays pharmacodynamic synergy at lower doses in HepG2 cells.
PubMed:Natural stilbenoids isolated from grapevine exhibiting inhibitory effects against HIV-1 integrase and eukaryote MOS1 transposase in vitro activities.
PubMed:Differential induction of antioxidant stilbenoids in hairy roots of Vitis rotundifolia treated with methyl jasmonate and hydrogen peroxide.
PubMed:Comparative analyses of stilbenoids in canes of major Vitis vinifera L. cultivars.
PubMed:Osmotic stress-induced polyamine oxidation mediates defence responses and reduces stress-enhanced grapevine susceptibility to Botrytis cinerea.
PubMed:Bioactive stilbenes from Vitis vinifera grapevine shoots extracts.
PubMed:3D NMR structure of a complex between the amyloid beta peptide (1-40) and the polyphenol ε-viniferin glucoside: implications in Alzheimer's disease.
PubMed:Inhibition of Pseudomonas aeruginosa and Escherichia coli O157:H7 biofilm formation by plant metabolite ε-viniferin.
PubMed:New resveratrol oligomer derivatives from the roots of Rheum lhasaense.
PubMed:Vitis vinifera canes, a new source of antifungal compounds against Plasmopara viticola, Erysiphe necator, and Botrytis cinerea.
PubMed:Effect of trans-ε-viniferin on in vitro porcine oocyte maturation and subsequent developmental competence in preimplantation embryos.
PubMed:Antioxidant activity of selected stilbenoids and their bioproduction in hairy root cultures of muscadine grape (Vitis rotundifolia Michx.).
PubMed:trans-Resveratrol and ε-viniferin decrease glucose absorption in porcine jejunum and ileum in vitro.
PubMed:Profiling of neuraminidase inhibitory polyphenols from the seeds of Paeonia lactiflora.
PubMed:Stilbenoid profiles of canes from Vitis and Muscadinia species.
PubMed:Activity-guided isolation of resveratrol oligomers from a grapevine-shoot extract using countercurrent chromatography.
PubMed:Development of a rapid LC-UV method for the investigation of chemical and metabolic stability of resveratrol oligomers.
PubMed:Ethanolic extracts and isolated compounds from small-leaf grape (Vitis thunbergii var. taiwaniana) with antihypertensive activities.
PubMed:ε-Viniferin is more effective than its monomer resveratrol in improving the functions of vascular endothelial cells and the heart.
PubMed:trans-(-)-ε-Viniferin increases mitochondrial sirtuin 3 (SIRT3), activates AMP-activated protein kinase (AMPK), and protects cells in models of Huntington Disease.
PubMed:Stilbene levels in grape cane of different cultivars in southern Chile: determination by HPLC-DAD-MS/MS method.
PubMed:Evaluation of the Combined Effects of Stilbenoid from Shorea gibbosa and Vancomycin against Methicillin-Resistant Staphylococcus aureus (MRSA).
PubMed:Neuroprotection of the leaf and stem of Vitis amurensis and their active compounds against ischemic brain damage in rats and excitotoxicity in cultured neurons.
PubMed:Effects of elicitors on the production of resveratrol and viniferins in cell cultures of Vitis vinifera L. cv Italia.
PubMed:Greater effectiveness of ε-viniferin in red wine than its monomer resveratrol for inhibiting vascular smooth muscle cell proliferation and migration.
PubMed:Protective effect of ε-viniferin on β-amyloid peptide aggregation investigated by electrospray ionization mass spectrometry.
PubMed:Determination of stilbene derivatives in Burgundy red wines by ultra-high-pressure liquid chromatography.
PubMed:Improved resistance against Botrytis cinerea by grapevine-associated bacteria that induce a prime oxidative burst and phytoalexin production.
PubMed:Anti-inflammatory effects of resveratrol and oligostilbenes from Vitis thunbergii var. taiwaniana against lipopolysaccharide-induced arthritis.
PubMed:Malaysianol A, a new trimer resveratrol oligomer from the stem bark of Dryobalanops aromatica.
PubMed:Leaf and stem of Vitis amurensis and its active components protect against amyloid β protein (25-35)-induced neurotoxicity.
PubMed:In vitro BACE-1 inhibitory activity of resveratrol oligomers from the seed extract of Paeonia lactiflora.
PubMed:Stilbene production in cell cultures of Vitis vinifera L. cvs Red Globe and Michele Palieri elicited by methyl jasmonate.
PubMed:Three new oligostilbenes from the seeds of Paeonia suffruticosa.
PubMed:Vaticanol C, a resveratrol tetramer, activates PPARalpha and PPARbeta/delta in vitro and in vivo.
PubMed:Structures of two novel trimeric stilbenes obtained by horseradish peroxidase catalyzed biotransformation of trans-resveratrol and (-)-epsilon-viniferin.
PubMed:New stilbene dimers against amyloid fibril formation.
PubMed:Quantitative structure-antioxidant activity relationship of trans-resveratrol oligomers, trans-4,4'-dihydroxystilbene dimer, trans-resveratrol-3-O-glucuronide, glucosides: trans-piceid, cis-piceid, trans-astringin and trans-resveratrol-4'-O-beta-D-glucopyranoside.
PubMed:The antimicrobial activity of compounds from the leaf and stem of Vitis amurensis against two oral pathogens.
PubMed:Antidiabetogenic constituents from the Thai traditional medicine Cotylelobium melanoxylon.
PubMed:Bioassay-guided isolation of antiproliferative compounds from grape (Vitis vinifera) stems.
PubMed:Effects of resveratrol analogs on cell cycle progression, cell cycle associated proteins and 5fluoro-uracil sensitivity in human derived colon cancer cells.
PubMed:Stilbenes and oligostilbenes from leaf and stem of Vitis amurensis and their cytotoxic activity.
PubMed:Preparative purification of antiamyloidogenic stilbenoids from Vitis vinifera (Chardonnay) stems by centrifugal partition chromatography.
PubMed:A new specific BACE-1 inhibitor from the stembark extract of Vitis vinifera.
PubMed:Antilisterial activities of polyphenol-rich extracts of grapes and vinification byproducts.
PubMed:Botrytis cinerea Infection in Grape Flowers: Defense Reaction, Latency, and Disease Expression.
PubMed:Chitosan oligomers and copper sulfate induce grapevine defense reactions and resistance to gray mold and downy mildew.
PubMed:Opposite effects of two resveratrol (trans-3,5,4'-trihydroxystilbene) tetramers, vitisin A and hopeaphenol, on apoptosis of myocytes isolated from adult rat heart.
PubMed:Inhibition of human low density lipoprotein and high density lipoprotein oxidation by oligostilbenes from rhubarb.
PubMed:Optimization of solid-liquid extraction of resveratrol and other phenolic compounds from milled grape canes (Vitis vinifera).
PubMed:Antiproliferative activities of resveratrol and related compounds in human hepatocyte derived HepG2 cells are associated with biochemical cell disturbance revealed by fluorescence analyses.
PubMed:Lipoxygenase inhibitory constituents from rhubarb.
PubMed:Inhibitory effects of trans-resveratrol analogs molecules on the proliferation and the cell cycle progression of human colon tumoral cells.
PubMed:Effect of lime-induced leaf chlorosis on ochratoxin A, trans-resveratrol, and epsilon-viniferin production in grapevine (Vitis vinifera L.) berries infected by Aspergillus carbonarius.
PubMed:3-Hydroxy-3-methylglutaryl-CoA (HMG-CoA) reductase inhibitory effect of Vitis vinifera.
PubMed:Evaluation of antitumor effects of two vine stalk oligomers of resveratrol on a panel of lymphoid and myeloid cell lines: comparison with resveratrol.
PubMed:Hopeaphenol: the first resveratrol tetramer in wines from North Africa.
PubMed:Vasorelaxant effect of stilbenes from rhizome extract of rhubarb (Rheum undulatum) on the contractility of rat aorta.
PubMed:Cytotoxic resveratrol oligomers from the tree bark of Dipterocarpus hasseltii.
PubMed:(-)-Trans-epsilon-viniferin, a polyphenol present in wines, is an inhibitor of noradrenaline and 5-hydroxytryptamine uptake and of monoamine oxidase activity.
PubMed:Resveratrol oligomers are potent MRP1 transport inhibitors.
PubMed:Comparison of ozone and UV-C treatments on the postharvest stilbenoid monomer, dimer, and trimer induction in var. 'Superior' white table grapes.
PubMed:Reverse pharmacognosy: application of selnergy, a new tool for lead discovery. The example of epsilon-viniferin.
PubMed:Rapid analysis of stilbenes and derivatives from downy mildew-infected grapevine leaves by liquid chromatography-atmospheric pressure photoionisation mass spectrometry.
PubMed:Polyphenolic compounds from red grapes acutely improve endothelial function in patients with coronary heart disease.
PubMed:Determination of stilbenes (delta-viniferin, trans-astringin, trans-piceid, cis- and trans-resveratrol, epsilon-viniferin) in Brazilian wines.
PubMed:Resveratrol derivatives from the roots of Vitis thunbergii.
PubMed:Viniferin formation by COX-1: evidence for radical intermediates during co-oxidation of resveratrol.
PubMed:Regioselective oxidative coupling of 4-hydroxystilbenes: synthesis of resveratrol and epsilon-viniferin (E)-dehydrodimers.
PubMed:Insulin secretion and cyclooxygenase enzyme inhibition by cabernet sauvignon grape skin compounds.
PubMed:Antitumor effect of stilbenoids from Vateria indica against allografted sarcoma S-180 in animal model.
PubMed:Laminarin elicits defense responses in grapevine and induces protection against Botrytis cinerea and Plasmopara viticola.
PubMed:Delta-viniferin, a resveratrol dehydrodimer: one of the major stilbenes synthesized by stressed grapevine leaves.
PubMed:Differential inhibition of human cytochrome P450 enzymes by epsilon-viniferin, the dimer of resveratrol: comparison with resveratrol and polyphenols from alcoholized beverages.
PubMed:[Studies on chemical constituents of oligostilbenes from Vitis davidii Foex].
PubMed:Phenolic constituents of Gnetum klossii.
PubMed:Comparative antiproliferative and apoptotic effects of resveratrol, epsilon-viniferin and vine-shots derived polyphenols (vineatrols) on chronic B lymphocytic leukemia cells and normal human lymphocytes.
PubMed:Stilbenoids from the stem of Gnetum latifolium (Gnetaceae).
PubMed:Antioxidative activity of resveratrol and its derivatives isolated from seeds of Paeonia lactiflora.
PubMed:Diptoindonesin A, a new C-glucoside of epsilon-viniferin from Shorea seminis (Dipterocarpaceae).
PubMed:Cytotoxic and antimutagenic stilbenes from seeds of Paeonia lactiflora.
PubMed:Antioxidant properties of trans-epsilon-viniferin as compared to stilbene derivatives in aqueous and nonaqueous media.
PubMed:Stilbene content of mature Vitis vinifera berries in response to UV-C elicitation.
PubMed:Isolation and characterization of novel stilbene derivatives from Riesling wine.
PubMed:Oligostilbenoids in stem bark of Vatica rassak.
PubMed:Stilbenoids in the stem bark of Hopea parviflora.
PubMed:Stilbene oligomers in roots of Sophora davidii.
PubMed:Five new stilbene dimers from the lianas of Gnetum hainanense.
PubMed:Changes in the phytoalexin content of various Vitis spp. in response to ultraviolet C elicitation.
PubMed:Flexuosol A, a new tetrastilbene from vitis flexuosa
PubMed:Powerful hepatoprotective and hepatotoxic plant oligostilbenes, isolated from the Oriental medicinal plant Vitis coignetiae (Vitaceae).
 
Notes:
It is a resveratrol dimer.; e-viniferin is a naturally-occurring polyphenol, belonging to the stilbenes family. It is found in grapevines, in wines and in the Oriental medicinal plant Vitis coignetiae.
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