CHEBI:76147 - (2R,3R)-trans-δ-viniferin

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ChEBI Name (2R,3R)-trans-δ-viniferin ChEBI ID CHEBI:76147 ChEBI ASCII Name (2R,3R)-trans-delta-viniferin Definition A stilbenoid that is the (2R,3R)-trans-stereoisomer of δ-viniferin, obtained by cyclodimerisation of trans-resveratrol. Stars This entity has been manually annotated by the ChEBI Team. Supplier Information ChemicalBook:CB21387988, ZINC000006090922 Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Wikipedia License δ-Viniferin is a resveratrol dehydrodimer. It is an isomer of epsilon-viniferin. It can be isolated from stressed grapevine (Vitis vinifera) leaves. It is also found in plant cell cultures and wine. It can also be found in Rheum maximowiczii. It is a grapevine phytoalexin following stresses like fungal infection (by Plasmopara viticola, the agent of downy mildew), UV light irradiation or ozone treatment. Botryosphaeria obtusa, a pathogen responsible for the black dead arm disease of grapevine, has also been shown to be able to oxidise wood δ-resveratrol into delta-viniferin. In cell cultures, the use of methyl jasmonate and jasmonic acid as elicitors stimulates δ-viniferin biosynthesis. Delta-viniferin can also be produced from resveratrol by human PTGS1 (COX-1, cyclooxygenase-1) or from trans-resveratrol and (−)-epsilon-viniferin by horseradish peroxidase. Read full article at Wikipedia Formula C28H22O6 Net Charge 0 Average Mass 454.47070 Monoisotopic Mass 454.14164 InChI InChI=1S/C28H22O6/c29-20-6-4-18(5-7-20)28-27(19-12-23(32)15-24(33)13-19)25-11-16(3-8-26(25)34-28)1-2-17-9-21(30)14-22(31)10-17/h1-15,27-33H/b2-1+/t27-,28+/m1/s1 InChIKey LILPTCHQLRKZNG-CKKRXTSSSA-N SMILES Oc1ccc(cc1)[C@@H]1Oc2ccc(\C=C\c3cc(O)cc(O)c3)cc2[C@H]1c1cc(O)cc(O)c1 ChEBI Ontology Outgoing (2R,3R)-trans-δ-viniferin (CHEBI:76147) has functional parent trans-resveratrol (CHEBI:45713) (2R,3R)-trans-δ-viniferin (CHEBI:76147) is a 1-benzofurans (CHEBI:38830) (2R,3R)-trans-δ-viniferin (CHEBI:76147) is a polyphenol (CHEBI:26195) (2R,3R)-trans-δ-viniferin (CHEBI:76147) is a stilbenoid (CHEBI:26776) (2R,3R)-trans-δ-viniferin (CHEBI:76147) is enantiomer of (2S,3S)-trans-δ-viniferin (CHEBI:76141) Incoming (2S,3S)-trans-δ-viniferin (CHEBI:76141) is enantiomer of (2R,3R)-trans-δ-viniferin (CHEBI:76147) IUPAC Name 5-[(2R,3R)-5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol Synonyms Sources maximol A ChEBI resveratrol (E)-dehydrodimer ChEBI Manual Xref Database Delta-Viniferin Wikipedia View more database links Registry Number Type Source 22933537 Reaxys Registry Number Reaxys Last Modified 05 December 2013