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

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

Uses

Used in Pharmaceutical Industry:
Rhapontigenin is used as an anti-cancer agent for its ability to inhibit the proliferation of HepG2 and HL-60R cancer cell lines (IC50 = 48 μM). Its mechanism-based, selective inactivation of cytochrome P450 1A1 (IC50 = 400 nM) helps prevent the activation of polycyclic aromatic hydrocarbons that act as procarcinogens.
Used in Nutraceutical Industry:
Rhapontigenin is used as a dietary supplement for its antioxidant properties, which can help protect the body from oxidative stress and support overall health.

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 
• 621-58-9 3-hydroxy-4-methoxystyrene 
• 64339-43-1 5-iodoresorcinol 
• 10083-24-6 trans-piceatannol 
• 74-88-4 methyl iodide 

Downstream Products

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

A method for the synthesis of hydroxy [...] composition of the new method (by machine translation)

The present invention discloses a new method for the synthesis of hydroxy [...] compound. The claimed method is: in the organic solvent, under a certain temperature, ammonium formate/through the palladium catalytic removal of benzyl protecting group system, to obtain hydroxyl [...] compound. The method has the mild reaction conditions, the operation is simple, small reagent toxicity, safety, high yield, wide range of application, low cost, relatively suitable for mass production and the like. (by machine translation)

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

Resveratrol derived butyrylcholinesterase inhibitors

Novel polyhydroxylated (E)-stilbenes were synthesized by Mizoroki-Heck reactions and tested for their ability to inhibit the enzymes acetyl- and butyrylcholinesterase. Several of them are good inhibitors of butyrylcholinesterase; one of them carrying an extra fluorine substituent is a 94-fold stronger inhibitor of butyrylcholinesterase than of acetylcholinesterase. Novel polyhydroxylated (E)-stilbenes synthesized by Mizoroki-Heck reactions were tested for their ability to inhibit the enzymes acetyl- and butyrylcholinesterase. Several of them were found to be good inhibitors of butyrylcholinesterase. One of them carrying an extra fluorine substituent is a 94-fold stronger inhibitor of butyrylcholinesterase than of acetylcholinesterase.

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.

Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents

Resveratrol 1 (3,4′,5-trihydroxy-trans-stilbene), a phytoalexin present in grapes and other food products, has recently been suggested as a potential cancer chemopreventive agent based on its striking inhibitory effects on cellular events associated with cancer initiation, promotion, and progression. This triphenolic stilbene has also displayed in vitro growth inhibition in a number of human cancer cell lines. In this context, a series of cis- and trans-stilbene-based resveratrols were prepared with the aim of discovering new lead compounds with clinical potential. All the synthesized compounds were tested in vitro for cell growth inhibition and the ability to induce apoptosis in HL60 promyelocytic leukemia cells. The tested trans-stilbene derivatives were less potent than their corresponding cis isomers, except for trans-resveratrol, whose cis isomer was less active. The best results were obtained with compounds 11b and 7b, the cis-3,5-dimethoxy derivatives of rhapontigenin 10a (3,5,3′-trihydroxy-4′methoxy-transstilbene) and its 3′-amino derivative 10b, respectively, which showed apoptotic activity at nanomolar concentrations. The corresponding trans isomers 12b and 8b were less active both as antiproliferative and as apoptosis-inducing agents. Of interest, 11b and 7b were active toward resistant HL60R cells and their activity was higher than that of several classic chemotherapeutic agents. The flow cytometry assay showed that at 50 nM compounds 7b or 11b were able to recruit almost all cells in the apoptotic sub-G0-G1 peek, thus suggesting that the main mechanism of cytotoxicity of these compounds could be the activation of apoptosis. These data indicate unambiguously that structural alteration of the stilbene motif of resveratrol can be extremely effective in producing potent apoptosis-inducing agents.

STILBENE GLYCOSIDES FROM GUIBOURTIA TESSMANNII

(E)-3,4'-Dimethoxy-5-rutinosyl stibene, rhaponticin and piceid have been isolated from the stem bark of Guibourtia tessmannii. - Key words: Guibourtia tessmannii; Cesalpiniaceae; stem bark; chemistry; stilbene glycoside.

Studies on Rhubarb (Rhei Rhizoma). VI. Isolation and Characterization of Stilbenes

Nineteen stilbene derivatives (I-XIX), of which five are novel cis-stilbenes, have been obtained from a rhubarb of low quality (commercial name:, Imo-Daio).Based on chemical and spectroscopic evidence, these compounds have been characterized as rhapontigenin (I), rhaponticin (II), rhapontigenin 3'-O-β-D-glucopyranoside (III), rhaponticin 6''-O-gallate (IV), rhaponticin 2''-O-gallate (V), rhaponticin 2''-O-p-coumarate (VI), piceatannol (VII), piceatannol 3-O-β-D-glucopyranoside (VIII), piceatannol 3'-O-β-D-glucopyranoside (IX), piceatannol 3'-O-β-D-xylopyranoside (X), piceatannol 3-O-β-D-(6''-O-galloyl) glucopyranoside (XI), desoxyrhaponticin (XII), desoxyrhaponticin 6''-O-gallate (XIII), 3,4',5-trihydroxystilbene 4'-O-β-D-(6''-O-galloyl) glucopyranoside (XIV), cis-3,3',5-trihydroxy-4'-methoxystilbene 3-O-β-D-glucopyranoside (XV), cis-3,3',5-trihydroxy-4'-methoxystilbene 3-O-β-D-(6''-O-galloyl) glucopyranoside (XVI), cis-3,5-dihydroxy-4'-methoxystilbene 3-O-β-D-glucopyranoside (XVII), cis-3,3',5-trihydroxy-4'-methoxystilbene 3-O-β-D-(2''-O-galloyl) glucopyranoside (XVIII) and cis-3,3',5-trihydroxy-4'-methoxystilbene (XIX).Keywords - rhubarb; Polygonaceae; trans-stilbene; cis-stilbene; gallic acid ester; p-coumaric acid ester; rhaponticin; desoxyrhaponticin; piceatannol; 3,4',5-trihydroxystilbene