3-(3,5-Dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(Z)-4-hydroxystyryl]-2,3-dihydrobenzofuran

Base Information

• Chemical Name: 3-(3,5-Dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(Z)-4-hydroxystyryl]-2,3-dihydrobenzofuran
• CAS No.: 62218-08-0
• Molecular Formula: C₂₈H₂₂O₆
• Molecular Weight: 454.479
• Nikkaji Number: J2.924.683A
• Mol file: 62218-08-0.mol

Synonyms:3-(3,5-Dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(Z)-4-hydroxystyryl]-2,3-dihydrobenzofuran;5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(Z)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol

Chemical Property of 3-(3,5-Dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(Z)-4-hydroxystyryl]-2,3-dihydrobenzofuran

Chemical Property:

• Vapor Pressure: 6.04E-20mmHg at 25°C
• Melting Point: 147 - 149 °C
• Boiling Point: 694.8°Cat760mmHg
• Flash Point: 374°C
• PSA: 110.38000
• Density: 1.45g/cm³
• LogP: 5.65060
• 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:

98%Min ^*data from raw suppliers

ε-Viniferin 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

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=C3C(C(OC3=CC(=C2)O)C4=CC=C(C=C4)O)C5=CC(=CC(=C5)O)O)O
• Description: trans-ε-Viniferin is a stilbene polyphenol and dimer of trans-resveratrol that has been found in various red wines and has diverse biological activities. It induces disaggregation of aggregated amyloid-β (1-42) (Aβ42; ) fibrils in a cell-free assay and decreases Aβ42- and IL-1β-induced release of TNF-α and IL-6 in primary mouse neuron and astrocyte cocultures. trans-ε-Viniferin reduces cytotoxicity induced by truncated huntingtin (Htt) in PC12 cells (EC50 = 30 nM). It also reduces production of reactive oxygen species (ROS), mitochondrial dysfunction, and PGC-1α depletion and increases protein levels and deacetylase activity of sirtuin 3 (SIRT3) in cells expressing mutant Htt. trans-ε-Viniferin inhibits calcium-activated chloride channel currents in HT-29 cells (IC50 = ~1 μM). In vivo, trans-ε-viniferin (2 μg per animal) reduces rotavirus-induced secretory diarrhea in mice without affecting the rotaviral infection. Dietary administration of trans-ε-viniferin reduces hepatic triglyceride accumulation and body weight increases in a mouse model of diet-induced obesity.
• Uses: ε-Viniferin is a stilbene extract posessing cytotoxic effects and may contain anti-cancer properties.

Technology Process of 3-(3,5-Dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(Z)-4-hydroxystyryl]-2,3-dihydrobenzofuran

There total 4 articles about 3-(3,5-Dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(Z)-4-hydroxystyryl]-2,3-dihydrobenzofuran 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

(+)-cis-ε-viniferin

Refernces

• 1、 Lee, Sungjin,Mailar, Karabasappa,Il Kim, Mi,Park, Minkyung,Kim, Jiseon,Min, Dal-Hee,Heo, Tae-Hwe,Bae, Soo Kyung,Choi, Wonjun,Lee, Choongho. "Plant-derived purification, chemical synthesis, and in vitro/in vivo evaluation of a resveratrol dimer, viniferin, as an HCV Replication inhibitor". . . Retrieved 2019/11/11.
• 2、 Zhang, Jian-Qiao,Li, Gan-Peng,Kang, Yu-Long,Teng, Bin-Hao,Yao, Chun-Suo. "Biomimetic synthesis of resveratrol trimers catalyzed by horseradish peroxidase". supporting information. . Retrieved 2017/06/08.