Isorhapontin
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Names | |
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IUPAC name 3-Hydroxy-5-[(1E)-2-(4-hydroxy-3-methoxyphenyl)ethen-1-yl]phenoxy β-D-glucopyranoside | |
Systematic IUPAC name (2S,3R,4S,5S,6R)-2-{3-Hydroxy-5-[(1E)-2-(4-hydroxy-3-methoxyphenyl)ethen-1-yl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol | |
Other names Isorhapontigenin glucoside | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.230.305 |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C21H24O9 | |
Molar mass | 420.41 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Isorhapontin is a stilbenoid. It is the glucoside of isorhapontigenin. It can be found in mycorrhizal and non-mycorrhizal roots of Norway spruces (Picea abies),[1] in the bark of Picea sitchensis[2][3] or in white spruce (Picea glauca).[4]
References
[edit]- ^ Münzenberger, B; Heilemann, J; Strack, D; Kottke, I; Oberwinkler, F (1990). "Phenolics of mycorrhizas and non-mycorrhizal roots of Norway spruce". Planta. 182 (1): 142–148. doi:10.1007/BF00239996. PMID 24197010. S2CID 43504838.
- ^ Stilbene glucosides in the bark of Picea sitchensis. Masakazu Aritomi, Dervilla M.X. Donnelly, Phytochemistry, Volume 15, Issue 12, 1976, Pages 2006–2008, doi:10.1016/S0031-9422(00)88881-0
- ^ Astringin and isorhapontin distribution in Sitka spruce trees. Claudia D. Toscano Underwood and Raymond B. Pearce, Phytochemistry, Volume 30, Issue 7, 1991, Pages 2183–2189, doi:10.1016/0031-9422(91)83610-W
- ^ Hammerbacher, A.; Ralph, S. G.; Bohlmann, J.; Fenning, T. M.; Gershenzon, J.; Schmidt, A. (2011). "Biosynthesis of the Major Tetrahydroxystilbenes in Spruce, Astringin and Isorhapontin, Proceeds via Resveratrol and is Enhanced by Fungal Infection". Plant Physiology. 157 (2): 876–890. doi:10.1104/pp.111.181420. PMC 3192583. PMID 21865488.