266997-55-1

Basic information

• Product Name: (2S,3R,4S,5R,6R)-2-{3-[(E)-2-(3,4-Dimethoxy-phenyl)-vinyl]-5-methoxy-phenoxy}-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran
• Synonyms: (2S,3R,4S,5R,6R)-2-{3-[(E)-2-(3,4-Dimethoxy-phenyl)-vinyl]-5-methoxy-phenoxy}-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran
• CAS NO: 266997-55-1
• Molecular Weight: 504.577
• Mol File: 266997-55-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2S,3R,4S,5R,6R)-2-{3-[(E)-2-(3,4-Dimethoxy-phenyl)-vinyl]-5-methoxy-phenoxy}-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4S,5R,6R)-2-{3-[(E)-2-(3,4-Dimethoxy-phenyl)-vinyl]-5-methoxy-phenoxy}-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran(266997-55-1)
• EPA Substance Registry System: (2S,3R,4S,5R,6R)-2-{3-[(E)-2-(3,4-Dimethoxy-phenyl)-vinyl]-5-methoxy-phenoxy}-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran(266997-55-1)

Safety Data

• Hazardous Substances Data: 266997-55-1(Hazardous Substances Data)

Upstream product

• 155-58-8 rhaponticin 
• 74-88-4 methyl iodide 

Downstream Products

• 62502-00-5 3-hydroxy-4,3,5-trimethoxy-trans-stilbene 
• 108957-73-9 NSC₃₈₁₈₆₄ 

Relevant articles and documents

Inhibitors from rhubarb on lipopolysaccharide-induced nitric oxide production in macrophages: Structural requirements of stilbenes for the activity

By bioassay-guided separation, three stilbenes (rhapontigenin, piceatannol, and resveratrol), two stilbene glucoside gallates (rhaponticin 2″-O-gallate and rhaponticin 6″-O-gallate), and a naphthalene glucoside (torachrysone 8-O-β-D-glucopyranoside) with inhibitory activity against nitric oxide (NO) production in lipopolysaccharide-activated macrophages were isolated (IC50=11-69μM). The oxygen functions (-OH, -OCH3) of stilbenes at the benzene ring were essential for the activity. The glucoside moiety reduced the activity, while the α,β-double bond had no effect. Furthermore, the active stilbenes (rhapontigenin, piceatannol, and resveratrol) did not inhibit inducible NO synthase activity, but they inhibited nuclear factor-κB activation following expression of iNOS. Copyright

Effects of stilbene constituents from rhubarb on nitric oxide production in lipopolysaccharide-activated macrophages

Two new anthraquinone glucosides [chrysophanol 8-O-β-D-(6'-galloyl)-glucopyranoside, aloe-emodin 1-O-β-D-glucopyranoside] together with various known stilbenes and their glucosides, anthraquinone glucosides, and a naphthalene glucoside were isolated from the rhizome of Rheum undulatum L. Three stilbenes (rhapontigenin, piceatannol, resveratrol), a naphthalene glucoside (torachrysone 8-O-β-D-glucopyranoside), and two stilbene glucoside gallates (rhaponticin 2'-O-gallate, rhaponticin 6'-O-gallate) showed inhibitory activity of NO production in lipopolysaccharide-activated macrophages. (IC50 = 11-69 μM). The oxygen functions (-OH,-OCH3) at the benzene ring were found to be essential to show the activity. Whereas, the glucoside moiety reduced the activity, while the α,β-double bond did not affect the activity. Furthermore, the active stilbenes (rhapontigenin, piceatannol, resveratrol) inhibited iNOS induction. (C) 2000 Elsevier Science Ltd. All rights reserved.