(E)-5-(4-Methoxystyryl)benzene-1,3-diol

Base Information

• Chemical Name: (E)-5-(4-Methoxystyryl)benzene-1,3-diol
• CAS No.: 33626-08-3
• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 242.274
• UNII: RU7RRY3RUW
• DSSTox Substance ID: DTXSID101031720
• Nikkaji Number: J948.177J,J903.868J
• Wikipedia: 4-Methoxyresveratrol
• Wikidata: Q17299987
• Pharos Ligand ID: HB4B3FRAG8PG
• Metabolomics Workbench ID: 130050
• ChEMBL ID: CHEMBL291501
• Mol file: 33626-08-3.mol

Synonyms:3,5-dihydroxy-4'-methoxystilbene;deoxyrhapontigenin;desoxyrhapontigenin;DHMS cpd

Chemical Property of (E)-5-(4-Methoxystyryl)benzene-1,3-diol

Chemical Property:

• Melting Point: 158-166 °C
• Boiling Point: 446.5±14.0 °C(Predicted)
• PKA: 9.19±0.10(Predicted)
• Flash Point: 223.8oC
• PSA: 49.69000
• Density: 1.252
• LogP: 3.27680
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 242.094294304
• Heavy Atom Count: 18
• Complexity: 259

Purity/Quality:

≥98% ^*data from raw suppliers

4'-METHOXYRESVERATROL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C=CC2=CC(=CC(=C2)O)O
• Isomeric SMILES: COC1=CC=C(C=C1)/C=C/C2=CC(=CC(=C2)O)O
• Uses: 4''-O-Methylresveratrol is an impurity of resveratrol (R150000), an anticancer agent that has been shown to inhibit events associated with tumor initiation, promotion and progression. 4'-O-Methylresveratrol is an impurity of resveratrol (R150000), an anticancer agent that has been shown to inhibit events associated with tumor initiation, promotion and progression.

Technology Process of (E)-5-(4-Methoxystyryl)benzene-1,3-diol

There total 35 articles about (E)-5-(4-Methoxystyryl)benzene-1,3-diol 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: 95.0%

(E)-3,5-di-(tert-butyldimethylsilyloxy)-4'-methoxystilbene (192710-87-5) → 5-[(E)-2-(4-methoxyphenyl)vinyl]benzene-1,3-diol (65728-21-4,33626-08-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2013.02.024

Reference yield: 91.0%

(E)-3,5-dibenzyloxy-4'-methoxystilbene (1252932-07-2) → 5-[(E)-2-(4-methoxyphenyl)vinyl]benzene-1,3-diol (65728-21-4,33626-08-3)

Guidance literature:

With hydrogen; In dichloromethane; at 20 ℃; for 5h; under 3750.38 Torr;

Reference yield: 90.0%

cis-3,5-diisopropoxy-4'-methoxystilbene (587870-72-2) → 5-[(E)-2-(4-methoxyphenyl)vinyl]benzene-1,3-diol (65728-21-4,33626-08-3)

Guidance literature:

With boron trichloride; In dichloromethane; at -78 - 0 ℃;

DOI:10.1016/S0040-4020(03)00405-8

upstream raw materials:

(E)-3,5-di-(tert-butyldimethylsilyloxy)-4'-methoxystilbene

cis-3,5-diisopropoxy-4'-methoxystilbene

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

methyl iodide

Downstream raw materials:

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

α,β-dihydro-3,5-dihydroxy-4'-methoxystilbene

(E)-5-hydroxy-4'-methoxy-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)stilbene

(E)-1-(3,5-di-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl)-2-(4'-methoxy-phenyl)ethene

Refernces

• 1、 -. "Resveratrol derivative or medical application thereof in fibrosis resistance". Paragraph 0063-0066. . Retrieved 2020/10/14.
• 2、 -. "Method for synthesizing artificially all-trans-resveratrol and derivative thereof". Paragraph 0064; 0065. . Retrieved 2017/08/31.