5274. Kaempferol

Nomenclature

CAS number: 520-18-3
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 3,4′,5,7-tetrahydroxyflavone; nimbecetin; pelargidenolon 1497; populnetin; rhamnolutein; robigenin; swartziol; trifolitin.
C15H10O6; mol wt 286.24.
C 62.94%, H 3.52%, O 33.54%.

Description and references

Plant flavonoid isolated from Delphinium consolida L., Ranunculaceae: A. G. Perkin, E. J. Wilkinson, J. Chem. Soc. 81, 585 (1902); from grapefruit (Citrus paradisi Macf., Rutaceae): Dunlap, Wender, Anal. Biochem. 4, 110 (1962); from stems and seeds of Cuscuta reflexa Roxb., Convolvulaceae: K. W. Gopinath et al., J. Sci. Ind. Res. 21B, 601 (1962), C.A. 58, 7134e (1963). Identity with swartziol: M. R.-R. Paris, L. Bézanger-Beauquesne, Compt. Rend. 242, 1761 (1956). Structure: S. von Kostanecki, A. Rozycki, Ber. 34, 3721 (1901). Total synthesis: Y.-H. Lu et al., Yao Hsueh Hsueh Pao 15, 477 (1980), C.A. 94, 174808a (1981). Convenient synthesis: M. Ichikawa et al., Org. Prep. Proced. Int. 14, 183 (1982). Mutagenicity studies: J. T. MacGregor, L. Jurd, Mutat. Res. 54, 297 (1978); A. A. Hardigree, J. L. Epler, ibid. 58, 231 (1978). HPLC determination in soybean: J. D. Gaynor et al., Chromatographia 25, 1049 (1988).

Chemical structure

Properties

Yellow needles, mp 276-278°; also reported as light yellow powder from ethanol-water, mp 278-280° (dec) (Ichikawa). uv max: 265, 365 nm. Slightly sol in water; sol in hot alcohol, ether or alkalies.

Derivative

3,7-Dirhamnoside.

Nomenclature

Kaemferitrin; lespedin.
C27H30O14; mol wt 578.52.
C 56.05%, H 5.23%, O 38.72%.

Description and references

Isoln from the leaves of Indigo arrecta Benth., Leguminosae: Perkin, J. Chem. Soc. 91, 435 (1907); from leaves of Trichosanthus cucumeroides Maxim., Cucurbitaceae: Nakaoki, Morita, J. Pharm. Soc. Jpn. 77, 108 (1957). Identity with lespedin: Hatlori, Nature 168, 788 (1952).

Properties

Crystals from dil alc, mp 201-203°. Slightly sol in boiling water and cold alcohol.

Derivative

3-Glucoside.

Nomenclature

Astragalin.
C21H20O11; mol wt 448.38.
C 56.25%, H 4.50%, O 39.25%.

Description and references

From Podophyllum peltatum L. and P. emodi Wall., Berberidaceae. Isoln and structure: von Wartburg, Kuhn, Experientia 21, 67 (1965).

Properties

Crystals from methanol, mp 175-178°. [α]D20 16.9° (c = 0.45 in methanol).