8158. Resveratrol

Nomenclature

CAS number: 501-36-0
5-[(1E)-2-(4-hydroxyphenyl)ethenyl]-1,3-benzenediol; trans-resveratrol; (E)-5-(p-hydroxystyryl)resorcinol; 3,4′,5-stilbenetriol; 3,5,4′-trihydroxystilbene.
C14H12O3; mol wt 228.24.
C 73.67%, H 5.30%, O 21.03%.

Description and references

Phytoalexin found in a variety of plants; active ingredient of Asian folk medicine “Kojo-Kon” which is the powdered root of the Japanese knotweed. Isoln from white hellebore and structure: M. Takaoka, J. Fac. Sci., Hokkaido Imp. Univ. Ser. 3 3, 1 (1940); C.A. 34, 7887 (1940); from fescue grass: R. G. Powell et al., Phytochemistry 35, 335 (1994). Isoln of monomers, oligomers, isomers and glucosides from wine: F. Mattivi et al., J. Agric. Food Chem. 43, 1820 (1995). GC-MS determn: D. M. Goldberg et al., J. Am. Enol. Viticult. 46, 159 (1995). Produced as stress metabolite in response to fungal infection or injury: G. H. Dai et al., Physiol. Mol. Plant Pathol. 46, 177 (1995); P. Jeandet et al., J. Phytopathol. 143, 135 (1995). Antiplatelet aggregating activity: A. A. E. Bertelli et al., Int. J. Tissue React. 17, 1 (1995); and implications in coronary heart disease: C. R. Pace-Asciak et al., Clin. Chim. Acta 235, 207 (1995).

Chemical structure

Properties

Off-white powder from MeOH, mp 253-255°.

Derivative

3-β-mono-d-glucoside.

Nomenclature

CAS number: 27208-80-6
Polydatin; piceid.
C20H22O8; mol wt 390.38.
C 61.53%, H 5.68%, O 32.79%.

Description and references

Isoln from fresh root of Polygonum cuspidatum Sieb. & Zucc., Polygonaceae, and structure: Nonomura et al., Yakugaku Zasshi 83, 988 (1963).

Derivative

(Z)-Form.

Nomenclature

CAS number: 61434-67-1
cis-Resveratrol.

Description and references

GC-MS determn in wine: D. M. Goldberg et al., J. Agric. Food Chem. 43, 1245 (1995).