5221. Isoquercitrin

Nomenclature

CAS number: 21637-25-2
2-(3,4-Dihydroxyphenyl)-3-(β-d-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one; 3,3′,4′,5,7-pentahydroxyflavone-3-glucoside; quercetin-3-glucoside; isotrifoliin; trifoliin.
C21H20O12; mol wt 464.38.
C 54.31%, H 4.34%, O 41.34%.

Description and references

From flowers of Gossypium herbaceum L., Malvaceae: Perkin, J. Chem. Soc. 95, 2181 (1909); from flowers of Aesculus hippocastanum L., Hippocastanaceae: Hrhammer, Wagner, Arch. Pharm. 290, 224 (1957); from Tropaeolum majus L., Tropaeolaceae: Delaveau, Compt. Rend. 252, 1510 (1961); from Arnica montana L., Compositae: Friedrick, Naturwissenschaften 49, 541 (1962). Structure: Attree, Perkin, J. Chem. Soc. 1927, 234. Identity with trifoliin and isotrifoliin: Hattori et al., J. Chem. Soc. Jpn. 58, 844 (1937), C.A. 32, 219c (1938). Synthesis: Ice, Wender, J. Am. Chem. Soc. 74, 4606 (1952); eidem, US 2727890 (1955 to the USAEC).

Chemical structure

Properties

Yellow needles from water, mp 225-227°. uv max: 257, 369 nm. Practically insol in cold but sparingly sol in boiling water. Sol in alkaline solns with a deep yellow tint.