Ε-Viniferin

Chemical compound From Wikipedia, the free encyclopedia

ε-Viniferin is a naturally occurring polyphenol, belonging to the stilbenoids family. It is a resveratrol dimer.

Quick facts Names, Identifiers ...
ε-Viniferin
(−)-trans-ε-Viniferin
Names
Preferred IUPAC name
5-{(2R,3R)-6-Hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethen-1-yl]-2,3-dihydro-1-benzofuran-3-yl}benzene-1,3-diol
Other names
Viniferin
epsilon-Viniferin
(−)-epsilon-Viniferin
(−)-(E)-epsilon-viniferin
trans-ε-viniferin
(−)-Trans-epsilon-viniferin[1]
Iso-[epsilon]-viniferin[2]
cis-ε-viniferin
Cis-epsilon-viniferin[3]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • 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 checkY
    Key: FQWLMRXWKZGLFI-YVYUXZJTSA-N checkY
  • 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
  • C1=CC(=CC=C1C=CC2=CC(=CC3=C2C(C(O3)C4=CC=C(C=C4)O)C5=CC(=CC(=C5)O)O)O)O
Properties
C28H22O6
Molar mass 454.478 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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It is found in Vitis vinifera[4] grapevines,[5] in wines,[6] in the Oriental medicinal plant Vitis coignetiae and in the stem bark of Dryobalanops aromatica.[7]
Cis-epsilon-viniferin can be found in Paeonia lactiflora.[3]

It shows a human cytochrome P450 enzymes inhibition activity.[8]

Glycosides

Diptoindonesin A is a C-glucoside of ε-viniferin.

See also

References

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