epsilon-Viniferin

ε-Viniferin

IUPAC name 5-[(2R,3R)-6-Hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
Other names Viniferin; epsilon-Viniferin; (-)-epsilon-Viniferin
Identifiers
CAS number	62218-08-0^N
PubChem	5281728
ChemSpider	4445043^Y
ChEMBL	CHEMBL1224875^Y
Jmol-3D images	Image 1
SMILES C1=CC(=CC=C1C=CC2=CC(=CC3=C2C(C(O3)C4=CC=C(C=C4)O)C5=CC(=CC(=C5)O)O)O)O
InChI 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^Y Key: FQWLMRXWKZGLFI-YVYUXZJTSA-N^Y 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 Key: FQWLMRXWKZGLFI-YVYUXZJTBS
Properties
Molecular formula	C₂₈H₂₂O₆
Molar mass	454.47 g mol⁻¹
Exact mass	454.141638 u
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

ε-Viniferin is a naturally occurring phenol, belonging to the stilbenoids family. It is found in grapevines,^[1] in wines,^[2] in the Oriental medicinal plant Vitis coignetiae and in the stem bark of Dryobalanops aromatica.^[3]

Glycosides

^ A new class of phytoalexins from grapevines. P. Langcake and R. J. Pryce, Cellular and Molecular Life Sciences, 1977, Volume 33, Number 2, pp. 151-152, doi:10.1007/BF02124034 PMID 844529
^ Vitrac, Xavier; Bornet, Aurélie; Vanderlinde, Regina; Valls, Josep; Richard, Tristan; Delaunay, Jean-Claude; Mérillon, Jean-Michel; Teissédre, Pierre-Louis (2005). "Determination of Stilbenes (δ-viniferin, trans-astringin, trans-piceid, cis- and trans-resveratrol, ε-viniferin) in Brazilian Wines.". Journal of Agricultural and Food Chemistry 53 (14): 5664–9. doi:10.1021/jf050122g. PMID 15998130.
^ Malaysianol A, a new trimer resveratrol oligomer from the stem bark of Dryobalanops aromatica. Wibowo A, Ahmat N, Hamzah AS, Sufian AS, Ismail NH, Ahmad R, Jaafar FM, Takayama H. Fitoterapia. 2011 Jun, 82(4), pages 676-81, PubMed, doi:10.1016/j.fitote.2011.02.006

Stilbenoids and their glycosides

of resveratrol	Piceid \| Trans-resveratrol-3-O-glucuronide

Oligomeric forms

of resveratrol	Ampelopsin E \| Dimers : ε-viniferin, Parthenocissin A, Quadrangularin A, Pallidol and Amurensin A \| Trimers : α-viniferin, Laevifonol (an ε-viniferin-ascorbic acid hybrid compound), Malaysianol A, trans-diptoindonesin B \| Tetramers : Hopeaphenol \| Vitisins A, B and C

Oligomeric forms glycosides

Diptoindonesin A | Laevifoside (O-glucoside of ampelopsin A)

Misc

Synthetic

Stilbenoid drugs