4391. Genistein
Nomenclature
Description and references
Phytoestrogen found in soy products; the aglucon of genistin and of sophoricoside. Specific protein kinase inhibitor. Prepn from the glucoside by hydrolysis with emulsin: Charaux, Rabaté, J. Pharm. Chim. [9] 1, 404 (1941); by hydrolysis with HCl in methanol: Walter, J. Am. Chem. Soc. 63, 3273 (1941). Isoln from prunus spp., Rosaceae: Hasegawa ibid. 79, 1738 (1957); from Podocarpus spicata R.Br., Podocarpaceae: Briggs, Cebalo, Tetrahedron 6, 145 (1959). Structure: Baker, Robinson, J. Chem. Soc. 1925, 1981; 1926, 2713; Walz, Ann. 489, 118 (1931). Synthesis: Baker, Robinson, J. Chem. Soc. 1928, 3115; Narasimhachari et al., J. Sci. Ind. Res. 12, 287 (1953); Yoder et al., Proc. Iowa Acad. Sci. 61, 271 (1954); Zemplén et al., Acta Chim. Acad. Sci. Hung. 19, 277 (1959). HPLC determn in biological fluids: J. G. Supko, L. R. Phillips, J. Chromatogr. B 666, 157 (1995); A. A. Franke et al, Proc. Soc. Exp. Biol. Med. 208, 18 (1995). Review of synthesis and isotopic labeling: K. Whl et al., ibid. 27-32. Series of articles on chemopreventive properties and mechanism of action: ibid. 103-115, 120-130; J. Nutr. 125, Suppl. 3, 777S-797S (1995).
Properties
Rectangular or six-sided rods from 60% alcohol. Dendritic needles from ether. mp 297-298° (slight decompn). Sol in the usual organic solvents, in dil alkalies with yellow color. Practically insol in water. uv max: 262.5 nm (ε 138).Derivative
Sophoricoside.Nomenclature
Description and references
From the green pods of Sophora japonica L., Leguminosae: Charaux, Rabate, Bull. Soc. Chim. Biol. 20, 454 (1938). Structure: Zemplén et al., Ber. 76, 267 (1943). Synthesis: Bognár, Szabo, Acta Chim. Acad. Sci. Hung. 4, 383 (1954); Chem. Ind. (London) 1954, 518.
Properties
Crystals from alcohol, mp 298°. [α]D20 47° (pyridine). [α]D20 32° (10% aq pyridine). uv max (abs ethanol): 262 nm. Sparingly sol in water, alc, acetic acid; more sol in hot alc, hot acetic acid; sol in pyridine, dil alkalies. Practically insol in ethyl acetate, acetone.Derivative
Genistin.Nomenclature
Description and references
For isoln and structure see Walter, Hasegawa, Walz, loc. cit. Synthesis: Zemplén, Farkas, Ber. 76B, 1110 (1943).
Properties
Pale yellow plates from 80% ethanol, mp 256°. [α]D21 28° (c = 0.6 in 0.02N NaOH); [α]D26 21.4° (pyridine). uv max (85% ethanol): 262.5 nm (a 90.5). Practically insol in cold water. Slightly sol in hot water, hot ethanol, hot methanol; sol in hot 80% ethanol, hot 80% methanol, hot acetone, pyridine.Derivative
Olmelin.Nomenclature
5,7-Dihydroxy-4′-methoxyisoflavone; biochanin A; 4′-methyl ether.Description and references
Isoln from red clover: Pope et al., Chem. Ind. (London) 1953, 1092; Wong, J. Sci. Food Agric. 13, 304 (1962); from Andira inermis (Swartz) H.B.K., Leguminosae: Crocker et al., J. Chem. Soc. 1962, 4906. Identity with olmelin: Gakhokidze, J. Appl. Chem. USSR 23, 789 (1950), C.A. 46, 9098i (1952). Structure: Bose, Siddiqui, J. Sci. Ind. Res. 9B, no. 1, 25 (1950). Synthesis: Baker et al., Nature 169, 706 (1952).