500-65-2

Basic information

• Product Name: rhapontigenin
• Synonyms: rhapontigenin;(E)-5-[2-(3-Hydroxy-4-methoxyphenyl)ethenyl]-1,3-benzenediol;3,3',5-Trihydroxy-4'-methoxy-trans-stilbene trans-1-(3,5-Dihydroxyphenyl)-2-(3-hydroxy-4-methoxyphenyl)ethylene;(E)-4'-Methoxy-3,3',5-stilbenetriol;(E)-5-(3-Hydroxy-4-Methoxystyryl)benzene-1,3-diol;-5-(3-Hydroxy-4-methoxystyryl)
• CAS NO: 500-65-2
• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.272
• EINECS: 1312995-182-4
• Mol File: 500-65-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 189.0 to 193.0 °C
• Boiling Point: 503.6 °C at 760 mmHg
• Flash Point: 258.4 °C
• Appearance: White, off grey crystal powder
• Density: 1.345 g/cm³
• Vapor Pressure: 9.12E-11mmHg at 25°C
• Refractive Index: 1.722
• Solubility: ≤30mg/ml in ethanol;30mg/ml in DMSO;30mg/ml in dimethyl formamide
• PKA: 9.17±0.10(Predicted)
• CAS DataBase Reference: rhapontigenin(CAS DataBase Reference)
• NIST Chemistry Reference: rhapontigenin(500-65-2)
• EPA Substance Registry System: rhapontigenin(500-65-2)

Safety Data

• Hazardous Substances Data: 500-65-2(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 500-65-2 differently. You can refer to the following data:
1. Rhapontigenin is a natural analog of resveratrol and an inhibitor of CYP1A1.
2. 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

Different sources of media describe the Uses of 500-65-2 differently. You can refer to the following data:
1. 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]
2. Rhapontigenin is a natural analog of resveratrol and an inhibitor of CYP1A1.

references

[1]. chun yj, ryu sy, jeong tc, et al. mechanism-based inhibition of human cytochrome p450 1a1 by rhapontigenin. drug metab dispos. 2001 apr;29(4 pt 1):389-93.[2]. roberti m1, pizzirani d, simoni d, et al. synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents. j med chem. 2003 jul 31;46(16):3546-54.[3]. roupe ka1, helms gl, halls sc, et al. preparative enzymatic synthesis and hplc analysis of rhapontigenin: applications to metabolism, pharmacokinetics and anti-cancer studies. j pharm pharm sci. 2005 aug 22;8(3):374-86.

InChI:InChI=1/C15H14O4/c1-19-15-5-4-10(8-14(15)18)2-3-11-6-12(16)9-13(17)7-11/h2-9,16-18H,1H3/b3-2+

Upstream product

• 94356-22-6 5-[(2E)-(3,5-dihydroxyphenyl)vinyl]-2-methoxyphenyl-1-O-β-D-glucopyranoside 
• 155-58-8 rhaponticin 
• 24082-43-7 [3,5-di(benzyloxy)benzyl]triphenylphosphonium bromide 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 621-59-0 isovanillin 
• 24131-31-5 3,5-dibenzyloxybenzyl alcohol 
• 29654-55-5 5-(hydroxymethyl)benzene-1,3-diol 
• 29680-76-0 3,5-diacetoxybenzyl-(triphenyl)phosphonium bromide 
• 10083-24-6 trans-piceatannol 
• 74-88-4 methyl iodide 
• 621-58-9 3-hydroxy-4-methoxystyrene 
• 64339-43-1 5-iodoresorcinol 

Downstream Products

• 60640-97-3 α,α'-dihydro-3,5,3'-trihydroxy-4-methoxystilbene 
• 83088-26-0 (E)-tetramethylpiceatannol 
• 94425-95-3 5-[(1Z)-2-(3-hydoxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol 
• 14310-21-5 1-(4-methoxyphenyl)-2-phenylethane 

Relevant articles and documents

Method for synthesizing artificially all-trans-resveratrol and derivative thereof

The invention discloses a method for synthesizing artificially all-trans-resveratrol and a derivative thereof. In the method, the precursors of all-trans-resveratrol and the derivative thereof are prepared by means of constructing a conjugated fused ring, thus the all-trans-spatial structure of resveratrol and the derivative thereof is restricted completely, to prepare all-trans-resveratrol and the derivative thereof. The resulting product of the preparation method of 1,2-stilbene or the derivative thereof in the invention is of all-trans configuration, so as to meet the demand of biologically active substance chemicals. Compared to the previous processes, the method provided by the invention has the advantages of simple processes and mild conditions, thereby meeting the green chemistry concept.

Alkyl derivative manufacturing method

PROBLEM TO BE SOLVED: To provide a new method for producing an alkyl derivative of a polyphenol. SOLUTION: The method for producing an alkyl derivative of a polyphenol includes a step of reacting an acetic acid salt and an alkylating agent with the polyphenol. COPYRIGHT: (C)2013,JPOandINPIT

Syntheses of resveratrol and its hydroxylated derivatives as radical scavenger and tyrosinase inhibitor

Eight hydroxylated stilbene derivatives including resveratrol, desoxyrhapontigenin and piceatannol as potential radical scavenger and tyrosinase inhibitor are synthesized using optimized Wittig-Horner reaction for excellent trans-selectivity in good yields. Antioxidant activity was tested against ABTS radical and tyrosinase inhibitory activity was performed with L-tyrosine as the substrate based on previous procedure with some modification. In general, catecholic stilbenes showed stronger activity against ABTS radical and resorcinolic moiety showed stronger tyrosinase inhibitory activity. Synthetic piceatannol which containing both catecholic and resorcinolic moieties showed the strongest activity in both as ABTS radical scavenger and tyrosinase inhibitor with IC50 values of 4.1 and 8.6 μM, respectively.