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Isorhapontin

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Isorhapontin
Chemical structure of isorhapontin
Chemical structure of isorhapontin
Names
IUPAC name 3-Hydroxy-5-phenoxy β-D-glucopyranoside
Systematic IUPAC name (2S,3R,4S,5S,6R)-2-{3-Hydroxy-5-phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Other names Isorhapontigenin glucoside
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.230.305 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C21H24O9/c1-28-16-8-11(4-5-15(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/s1Key: KLPUXMNQDCUPNO-DXKBKAGUSA-N
SMILES
  • COC1=C(C=CC(=C1)/C=C/C2=CC(=CC(=C2)O3((((O3)CO)O)O)O)O)O
Properties
Chemical formula C21H24O9
Molar mass 420.41 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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), in the bark of Picea sitchensis or in white spruce (Picea glauca).

References

  1. 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.
  2. 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
  3. 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
  4. 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.
Hydroxystilbenes and their glycosides (monomeric forms)
Dihydroxylated
Trihydroxylated
Tetrahydroxylated
O-methylated
Combretastatins
carboxylated
other acylations
Glycosides
of resveratrol
of rhapontigenin
Oligomeric formsoligostilbenoids


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