Title: Kosins
Literature References: Phloroglucinols from flowers of Hagenia abyssinica J. J. Gmel. (Brayera anthelmintica Kunth.), Rosaceae. Isoln and early characterization: M. Leichsenring, Arch. Pharm. 232, 50 (1894); A. Lobeck, ibid. 239, 672 (1901); B. A. Hems, A. R. Todd, J. Chem. Soc. 1937, 562. Structure of a-kosin: W. Riedl, Ber. 89, 2600 (1956). Orginally identified as a- and b-kosins; ultimately shown to be a mixture of compds differing only in their acyl side chains. Structural elucidation of kosins and protokosin: M. Lounasmaa et al., Acta Chem. Scand. B28, 1200 (1974). Mass spectrometry: idem, P. Varenne, Planta Med. 34, 153 (1978). Identificaton and proportions in male and female flowers: T. Z. Woldemariam et al., Anal. Proc. 27, 178 (1990). Antitumor activity: idem, et al., J. Pharm. Biomed. Anal. 10, 555 (1992).
Derivative Type: a-Kosin
Additional Names: 5,5¢-Methylenebis[4,6-dihydroxy-2-methoxy-3-methylisobutyrophenone]
Molecular Formula: C25H32O8
Molecular Weight: 460.52
Percent Composition: C 65.20%, H 7.00%, O 27.79%
Properties: Yellow needles from ethanol, mp 160-160.5°. uv max: 227, 290 nm (e 30800, 24400). Soluble in alcohol, benzene, chloroform, ether, glacial acetic acid, alkalies.
Melting point: mp 160-160.5°
Absorption maximum: uv max: 227, 290 nm (e 30800, 24400)
Derivative Type: Protokosin
CAS Registry Number: 1392-97-8
Literature References: Structurally related phloroglucinol. Exists in several tautomeric forms and is a mixt of isobutyryl, isovaleryl, and 2-methylbutyryl side chain homologues.
Properties: Colorless needles from acetone, mp 181-183°. [a]D25 +13.9° (c = 0.610 in chloroform). uv max (cyclohexane): 224, 285 nm (e 28200, 36400). Practically insol in water. Slightly sol in alcohol, light petroleum; freely sol in ether, acetone, ethyl acetate, chloroform.
Melting point: mp 181-183°
Optical Rotation: [a]D25 +13.9° (c = 0.610 in chloroform)
Absorption maximum: uv max (cyclohexane): 224, 285 nm (e 28200, 36400)
Therap-Cat: Has been used as anthelmintic (Cestodes).
Keywords: Anthelmintic (Cestodes). |