Astringin

Astringin

Chemical structure of astringin
Names
IUPAC name 3-[(E)-2-(2,3-Dihydroxyphenyl)ethen-1-yl]-5-hydroxyphenyl β-D-glucopyranoside
Systematic IUPAC name (2S,3R,4S,5S,6R)-2-{3-[(E)-2-(3,4-Dihydroxyphenyl)ethen-1-yl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Identifiers
CAS Number	29884-49-9^N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:2899^N
ChEMBL	ChEMBL358769^Y
ChemSpider	4445028^Y
PubChem CID	5281712
UNII	4ER6YKM4YL^Y
CompTox Dashboard (EPA)	DTXSID401029689
InChI InChI=1S/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-13-6-11(5-12(22)8-13)2-1-10-3-4-14(23)15(24)7-10/h1-8,16-27H,9H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1^Y Key: PERPNFLGJXUDDW-CUYWLFDKSA-N^Y InChI=1/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-13-6-11(5-12(22)8-13)2-1-10-3-4-14(23)15(24)7-10/h1-8,16-27H,9H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1 Key: PERPNFLGJXUDDW-CUYWLFDKBH
SMILES O(c2cc(O)cc(\C=C\c1ccc(O)c(O)c1)c2)[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)CO
Properties
Chemical formula	C20H22O9
Molar mass	406.387 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Astringin is a stilbenoid, the 3-β-D-glucoside of piceatannol.[1] It can be found in the bark of Picea sitchensis[2][3] and Picea abies (Norway spruce).[4]

It is also present in Vitis vinifera cells cultures[5] and in wine.[6]

See also

• Phenolic compounds in wine

References

1. CID 5281712 from PubChem
2. Aritomi, Masakazu; Donnelly, Dervilla M.X. (1976). "Stilbene glucosides in the bark of Picea sitchensis". Phytochemistry. 15 (12): 2006–2008. Bibcode:1976PChem..15.2006A. doi:10.1016/S0031-9422(00)88881-0.
3. Toscano Underwood, Claudia D.; Pearce, Raymond B. (1991). "Astringin and isorhapontin distribution in Sitka spruce trees". Phytochemistry. 30 (7): 2183–2189. Bibcode:1991PChem..30.2183T. doi:10.1016/0031-9422(91)83610-W.
4. Lindberg, M.; Lundgren, L.; Gref, R.; Johansson, M. (1992). "Stilbenes and resin acids in relation to the penetration of Heterobasidion annosum through the bark of Picea abies". European Journal of Forest Pathology. 22 (2): 95–106. doi:10.1111/j.1439-0329.1992.tb01436.x.
5. Mérillon, J. M.; Fauconneau, B.; Teguo, P. W.; Barrier, L.; Vercauteren, J.; Huguet, F. (1997). "Antioxidant activity of the stilbene astringin, newly extracted from Vitis vinifera cell cultures". Clinical Chemistry. 43 (6 Pt 1): 1092–1093. doi:10.1093/clinchem/43.6.1092. PMID 9191572.
6. Vitrac, Xavier; Bornet, Aurélie; Vanderlinde, Regina; Valls, Josep; Richard, Tristan; Delaunay, Jean-Claude; Mérillon, Jean-Michel; Teissédre, Pierre-Louis (2005). "Determination of Stilbenes (δ-viniferin, trans-astringin, trans-piceid, cis- and trans-resveratrol, ε-viniferin) in Brazilian Wines". Journal of Agricultural and Food Chemistry. 53 (14): 5664–9. doi:10.1021/jf050122g. PMID 15998130.