Isorhapontin

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]

Isorhapontin

Names
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
CAS Number	32727-29-0
3D model (JSmol)	Interactive image
ChemSpider	4445032
ECHA InfoCard	100.230.305
KEGG	C10266
PubChem CID	5281716
UNII	BNH6WEN5L8 Y
CompTox Dashboard (EPA)	DTXSID701031823
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/s1 Key: KLPUXMNQDCUPNO-DXKBKAGUSA-N
SMILES COC1=C(C=CC(=C1)/C=C/C2=CC(=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](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 [77 °F], 100 kPa). Infobox references

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.