Rhaponticin

Chemical compound From Wikipedia, the free encyclopedia

Rhaponticin is a stilbenoid glucoside compound. Its aglycone is called rhapontigenin. It can be found in rhubarb rhizomes.[1]

Quick facts Names, Identifiers ...
Rhaponticin
Chemical structure of rhaponticin
Chemical structure of rhaponticin
Names
IUPAC name
3-Hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethen-1-yl]phenyl β-D-glucopyranoside
Systematic IUPAC name
(2S,3R,4S,5S,6R)-2-{3-Hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethen-1-yl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Other names
3',5-Dihydroxy-4'-methoxystilbene 3-O-beta-D-glucopyranoside
Ponticin
Rhapontin
Rhapontigenin glucoside
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.315 Edit this at Wikidata
EC Number
  • 205-845-0
KEGG
UNII
  • InChI=1S/C21H24O9/c1-28-16-5-4-11(8-15(16)24)2-3-12-6-13(23)9-14(7-12)29-21-20(27)19(26)18(25)17(10-22)30-21/h2-9,17-27H,10H2,1H3/b3-2+/t17-,18-,19+,20-,21-/m1/s1 â˜’N
    Key: GKAJCVFOJGXVIA-DXKBKAGUSA-N â˜’N
  • InChI=1/C21H24O9/c1-28-16-5-4-11(8-15(16)24)2-3-12-6-13(23)9-14(7-12)29-21-20(27)19(26)18(25)17(10-22)30-21/h2-9,17-27H,10H2,1H3/b3-2+/t17-,18-,19+,20-,21-/m1/s1
    Key: GKAJCVFOJGXVIA-DXKBKAGUBB
  • COc1ccc(cc1O)/C=C/c2cc(cc(c2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
Properties
C21H24O9
Molar mass 420,39 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa).
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It has beneficial effects on diabetic mice,[1] and in vitro results suggest it may be relevant to Alzheimer's disease with an action on beta amyloid.[2] It is a phytoestrogen and has estrogenic activity.[3][4]

References

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