(+)-epsilon-Viniferin

Base Information

• Chemical Name: (+)-epsilon-Viniferin
• CAS No.: 129170-22-5
• Molecular Formula: C₂₈H₂₂O₆
• Molecular Weight: 454.479
• European Community (EC) Number: 802-685-9
• UNII: 0AF07924BM
• Nikkaji Number: J752.909K
• Wikidata: Q27145775
• Metabolomics Workbench ID: 139306
• ChEMBL ID: CHEMBL498439

Synonyms:(+)-epsilon-Viniferin;Trans-E-Viniferin;trans-epsilon-Viniferin;UNII-0AF07924BM;0AF07924BM;129170-22-5;CHEBI:76137;1,3-Benzenediol, 5-((2S,3S)-2,3-dihydro-6-hydroxy-2-(4-hydroxyphenyl)-4-((1E)-2-(4-hydroxyphenyl)ethenyl)-3-benzofuranyl)-;5-[(2S,3S)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol;5-{(2S,3S)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl}benzene-1,3-diol;(+)-trans-epsilon-viniferin;CHEMBL498439;SCHEMBL13004136;TRANS-.EPSILON.-VINIFERIN;(+)-.EPSILON.-VINIFERIN;.EPSILON.-VINIFERIN, (E)-;.EPSILON.-VINIFERIN, (+)-;Q27145775

Chemical Property of (+)-epsilon-Viniferin

Chemical Property:

• XLogP3: 5.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 454.14163842
• Heavy Atom Count: 34
• Complexity: 672

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC2=C3C(C(OC3=CC(=C2)O)C4=CC=C(C=C4)O)C5=CC(=CC(=C5)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1/C=C/C2=C3[C@@H]([C@H](OC3=CC(=C2)O)C4=CC=C(C=C4)O)C5=CC(=CC(=C5)O)O)O

Technology Process of (+)-epsilon-Viniferin

There total 4 articles about (+)-epsilon-Viniferin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

viniferin pentaacetate → trans-ε-viniferin (62218-08-0,62250-12-8,129170-22-5,253435-07-3)

Guidance literature:

With potassium hydroxide; In methanol; at 35 ℃; for 0.5h;

DOI:10.3390/v11100890

Reference yield: 13.5%

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol (501-36-0) → trans-ε-viniferin (62218-08-0,62250-12-8,129170-22-5,253435-07-3)

Guidance literature:

With iron(III) chloride hexahydrate; In methanol; water; at 20 ℃; for 60h;

DOI:10.3390/molecules22050819

Reference yield:

1-(β-D-glucopyranosyloxy)-5-{(2R,3R)-6-(β-glucopyranosyloxy)-2-(4-hydroxyphenyl)-4-[(E)-4-hydroxystyryl]-2,3-dihydrobenzofuran-3-yl}benzene-3-ol (1246746-89-3) → (-)-ε-viniferin (62250-12-8,129170-22-5,62218-08-0,253435-07-3)

Guidance literature:

With water; β-glucosidase; at 37 ℃; for 24h; pH=6; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1021/np1002675

upstream raw materials:

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol

1-(β-D-glucopyranosyloxy)-5-{(2R,3R)-6-(β-glucopyranosyloxy)-2-(4-hydroxyphenyl)-4-[(E)-4-hydroxystyryl]-2,3-dihydrobenzofuran-3-yl}benzene-3-ol

(E)-5-((±)-6-hydroxy-2-(4-hydroxyphenyl)-4-(4-hydroxystyryl)-2,3-dihydrobenzofuran-3-yl)benzene-1,3-diol

Downstream raw materials:

4-hydroxy-benzaldehyde

C₃₃H₁₇F₁₅O₁₆S₅

C₂₈H₂₂O

C₂₁H₁₆O₂

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