32507-66-7

Basic information

• Product Name: isorhapontigenin
• Synonyms: isorhapontigenin;(E)-3,4',5-Trihydroxy-3'-methoxystilbene;(E)-3'-Methoxystilbene-3,4',5-triol;(E)-3-Methoxy-stilbene-4,3',5'-triol;5-[(E)-2-(4-Hydroxy-3-methoxyphenyl)ethenyl]-1,3-benzenediol;5-[(1E)-2-(4-Hydroxy-3-methoxyphenyl)ethenyl]-1,3-benzenediol;3,4',5-Trihydroxy-3'-methoxy-trans-stilbene;100mg
• CAS NO: 32507-66-7
• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.27
• EINECS: 1312995-182-4
• Mol File: 32507-66-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 180.0 to 184.0 °C
• Boiling Point: 471.8 °C at 760 mmHg
• Flash Point: 239.1 °C
• Appearance: white to light brown/
• Density: 1.345
• Vapor Pressure: 1.6E-09mmHg at 25°C
• Refractive Index: 1.722
• Storage Temp.: room temp
• Solubility: DMSO: soluble15mg/mL, clear
• PKA: 9.16±0.10(Predicted)
• CAS DataBase Reference: isorhapontigenin(CAS DataBase Reference)
• NIST Chemistry Reference: isorhapontigenin(32507-66-7)
• EPA Substance Registry System: isorhapontigenin(32507-66-7)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-41-43-51
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 32507-66-7(Hazardous Substances Data)

Usage

Biochem/physiol Actions

Isorhapontigenin or 4-methoxyresveratrol is a stilbene derivative isolated from a number of plants including Chinese medical herbs Gnetum Cleistostachyum and Iris Domestica (Belamcanda chinensis, leopard lily), and wine grapes. Similarly to resveratrol, isorhapontigenin is a potent antioxidant that attenuates ROS generation. Also, Isorhapontigenin exhibits pro-apoptopic and anti-cancer activities through downregulation of XIAP (X-linked inhibitor of apoptosis protein).

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

Upstream product

• 900515-78-8 C₂₁H₁₉IO₂ 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 58605-10-0 methyl 3,5-bis(benzyloxy)benzoate 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 10083-24-6 trans-piceatannol 
• 74-88-4 methyl iodide 
• 250778-33-7 (E)-1-(3-methoxy-4-benzyloxyphenyl)-2-(3,5-dibenzyloxyphenyl)ethylene 
• 121-33-5 vanillin 
• 29654-55-5 5-(hydroxymethyl)benzene-1,3-diol 
• 24131-31-5 3,5-dibenzyloxybenzyl alcohol 
• 20767-14-0 3,4',5-Triacetoxy-3'-methoxy-stilben-α-carbonsaeure 
• 32727-29-0 3-hydroxy-5-[(1E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]phenyl β-D-glucopyranoside 
• 29680-76-0 3,5-diacetoxybenzyl-(triphenyl)phosphonium bromide 

Downstream Products

• 83088-26-0 (E)-tetramethylpiceatannol 
• 291535-65-4 rac-shegansu B 
• 913556-40-8 rac-lehmbachol D 
• 291535-65-4 5-[2-(3-methoxy-4-hydroxyphenyl)-3-(3,5-dihydroxyphenyl)-7-methoxy-2,3-dihydro-5-benzofuranyl]vinyl-1,3-benzenediol 
• 291535-65-4 cis-shegansu B 
• 865474-98-2 6-hydroxy-3-(3,5-dihydroxyphenyl)-2-(3-methoxy-4-hydroxyphenyl)-4-(E)-(3-methoxy-4-hydroxystyryl)-2,3-dihydrobenzofuran 
• 139101-67-0 Tristin 

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

Antioxidant constituents from rhubarb: Structural requirements of stilbenes for the activity and structures of two new anthraquinone glucosides

The methanolic extracts from five kinds of rhubarb were found to show scavenging activity for DPPH radical and ·O2-. Two new anthraquinone glucosides were isolated from the rhizome of Rheum undulatum L. together with two anthraquinone glucosides, a naphthalene glucoside, and 10 stilbenes. In the screening test for radical scavenging activity of rhubarb constituents, stilbenes and a naphthalene glucoside showed activity, but anthraquinones and sennosides did not. In addition, most stilbenes inhibited lipid peroxidation of erythrocyte membrane by tert-butyl hydroperoxide. Detailed examination of the scavenging effect on various related compounds suggested the following structural requirements; 1) phenolic hydroxyl groups are essential to show the activity; 2) galloyl moiety enhances the activity; 3) glucoside moiety reduces the activity; 4) dihydrostilbene derivatives maintain the scavenging activity for the DPPH radical, but they show weak activity for ·O2-. In addition, several stilbenes with both the 3-hydroxyl and 4′-methoxyl groups inhibited xanthine oxidase.