Title: Silymarin
CAS Registry Number: 65666-07-1
Trademarks: Apihepar (Viatris); Laragon (Roemmers); Legalon (Madaus); Pluropon (Boehringer, Ing.); Silarine (Vir); Silepar (Ibirn); Silirex (Lampugnani); Silliver (Abbott); Silmar (Von Boch)
Literature References: Antihepatotoxic principle isolated from the seeds of the milk thistle, Silybum marianum (L.) Gaertn. (Carduus marianus L.). Comprised mainly of three isomers: silidianin, silicristin and the major component, silybin (formerly called silymarin). Characterized as a new class of substances, flavonolignans, almost certainly produced in the plant by a radical coupling of a flavonoid and coniferyl alcohol: Hänsel et al., Dtsch. Apoth. Ztg. 108, 1988 (1968). Isoln and chemistry: Wagner et al., Arzneim.-Forsch. 18, 688 (1968); 24, 466 (1974). Structural work: Janiak, Hänsel, Planta Med. 8, 71 (1960); Hänsel, Schöpflin, Tetrahedron Lett. 1967, 3645; Pelter, Hänsel, ibid. 1968, 2911. Pharmacology and toxicology: Hahn et al., Arzneim.-Forsch. 18, 698 (1968); H. M. Rauen, H. Schriewer, ibid. 23, 148-170 (1973); Halbach, Trost, ibid. 24, 866 (1974).
Derivative Type: Silybin
CAS Registry Number: 22888-70-6
CAS Name: (2R,3R)-2-[(2R,3R)-2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one
Additional Names: silibinin; silybum substance E6; silymarin I
Molecular Formula: C25H22O10
Molecular Weight: 482.44
Percent Composition: C 62.24%, H 4.60%, O 33.16%
Literature References: Revised structure and synthetic studies: R. Hänsel et al., Chem. Commun. 1972, 195; eidem, Ber. 110, 3664 (1977). Total synthesis: L. Merlini et al., Chem. Commun. 1979, 695; eidem, J. Chem. Soc. Perkin Trans. 1 1980, 775.
Properties: Anhydrous subst, mp 158°, dec 180°. [a]D20 +11° (c = 0.25 in acetone + alcohol). uv max (methanol): 288 nm (log e 4.33). Sol in acetone, ethyl acetate, methanol, ethanol; sparingly sol in CHCl3. Practically insol in water. Also occurs as the monohydrate, crystals from acetone + petr ether, mp 167°, dec 180°; from methanol + water, mp 180°.
Melting point: mp 158°; mp 167°; mp 180°
Optical Rotation: [a]D20 +11° (c = 0.25 in acetone + alcohol)
Absorption maximum: uv max (methanol): 288 nm (log e 4.33)
Therap-Cat: Hepatoprotectant.
Keywords: Hepatoprotectant.

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