5-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol

Base Information

• Chemical Name: 5-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol
• CAS No.: 500-65-2
• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.274
• Nikkaji Number: J3.003.246B
• Wikidata: Q76416112
• Metabolomics Workbench ID: 45144
• ChEMBL ID: CHEMBL333230
• Mol file: 500-65-2.mol

Synonyms:5-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol;3,3',5-trihydroxy-4'-methoxystilbene;(Z)-Rhapontigenin;CHEMBL333230;4'-Methoxy-3,3',5-trihydroxystilbene;3,5,3'-Trihydroxy-4'-methoxy-cis-stilben;1-(3,5-Dihydroxyphenyl)-2-(3-hydroxy-4-methoxyphenyl)ethylene

Chemical Property of 5-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol

Chemical Property:

• Appearance/Colour: White, off grey crystal powder
• Vapor Pressure: 9.12E-11mmHg at 25°C
• Melting Point: 186-187oC
• Refractive Index: 1.722
• Boiling Point: 503.6 °C at 760 mmHg
• PKA: 9.17±0.10(Predicted)
• Flash Point: 258.4 °C
• PSA: 69.92000
• Density: 1.345 g/cm³
• LogP: 2.98240
• Solubility.: ≤30mg/ml in ethanol;30mg/ml in DMSO;30mg/ml in dimethyl formamide
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 258.08920892
• Heavy Atom Count: 19
• Complexity: 295

Purity/Quality:

98%,99%, ^*data from raw suppliers

Rhapontigenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C=CC2=CC(=CC(=C2)O)O)O
• Isomeric SMILES: COC1=C(C=C(C=C1)/C=C\C2=CC(=CC(=C2)O)O)O
• Description: Rhapontigenin is a natural analog of resveratrol and an inhibitor of CYP1A1. Rhapontigenin is a natural analog of resveratrol with antioxidant and anti-cancer activity. It is a mechanism-based, selective inactivator of cytochrome P450 1A1 (IC50 = 400 nM), an aryl hydrocarbon hydroxylase which activates polycyclic aromatic hydrocarbons that act as procarcinogens. At higher concentrations, rhapontigenin inhibits the proliferation of HepG2 and HL-60R cancer cell lines (IC50 = 48 μM).
• Uses: Rhapontigenin is a natural analog of resveratrol with antioxidant and anti-cancer activity. It is a mechanism-based, selective inactivator of cytochrome P450 1A1 (IC50 = 400 nM), an aryl hydrocarbon hydroxylase which activates polycyclic aromatic hydrocarbons that act as procarcinogens. At higher concentrations, rhapontigenin inhibits the proliferation of HepG2 and HL-60R cancer cell lines (IC50 = 48 μM).[Cayman Chemical] Rhapontigenin is a natural analog of resveratrol and an inhibitor of CYP1A1.

Technology Process of 5-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol

There total 11 articles about 5-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]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: 88.0%

(E)-1-(3-benzyloxy-4-methoxyphenyl)-2-(3,5-dibenzyloxyphenyl)ethylene → rhapontigenin (500-65-2,65877-43-2,94425-95-3)

Guidance literature:

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

Reference yield: 8.1%

trans-piceatannol (10083-24-6,106325-86-4) + methyl iodide (74-88-4) → isorhapontigenin (32507-66-7) + (E)-5-[2-(3,4-dimethoxyphenyl)vinyl]benzene-1,3-diol (629643-27-2) + rhapontigenin (500-65-2,65877-43-2,94425-95-3) + 3,4,5′-trihydroxy-3′-methoxy-trans-stilbene

Guidance literature:

With sodium acetate; In N,N-dimethyl-formamide; at 100 ℃; for 0.0833333h;

Reference yield:

[3,5-di(benzyloxy)benzyl]triphenylphosphonium bromide (24082-43-7) → rhapontigenin (500-65-2,65877-43-2,94425-95-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

1.2: 54 percent / tetrahydrofuran; hexane / 20 °C

2.1: 16 percent / AlCl₃; N,N-dimethylaniline / CH₂Cl₂

With n-butyllithium; aluminium trichloride; N,N-dimethyl-aniline; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jm030785u

upstream raw materials:

5-[(2E)-(3,5-dihydroxyphenyl)vinyl]-2-methoxyphenyl-1-O-β-D-glucopyranoside

rhaponticin

[3,5-di(benzyloxy)benzyl]triphenylphosphonium bromide

3-benzyloxy-4-methoxybenzaldehyde

Downstream raw materials:

(E)-tetramethylpiceatannol

1-(4-methoxyphenyl)-2-phenylethane

α,α'-dihydro-3,5,3'-trihydroxy-4-methoxystilbene

5-[(1Z)-2-(3-hydoxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol

Refernces

• 1、 -. "A method for the synthesis of hydroxy [...] composition of the new method (by machine translation)". Paragraph 0073-0074. . Retrieved 2017/08/27.
• 2、 Csuk, Rene,Albert, Sabrina,Kluge, Ralph,Stroehl, Dieter. "Resveratrol derived butyrylcholinesterase inhibitors". . p. 499 - 503. Retrieved 2013/07/26.