Structural Formula Vector Image
Title: Scilliroside
CAS Registry Number: 507-60-8
CAS Name: (3b,6b)-6-(Acetyloxy)-3-(b-D-glucopyranosyloxy)-8,14-dihydroxybufa-4,20,22-trienolide
Molecular Formula: C32H44O12
Molecular Weight: 620.68
Percent Composition: C 61.92%, H 7.15%, O 30.93%
Literature References: Glycoside from red squill, the red variety of Urginea maritima (L.) Baker, Liliaceae: Stoll, Renz, Helv. Chim. Acta 25, 43 (1942); Wichtt, Fuchs, Arch. Pharm. 295, 361 (1962). Structure: Stoll et al., Helv. Chim. Acta 26, 648 (1943); von Wartburg, Renz, ibid. 42, 1620 (1959). Toxicity data: F. Dybing et al., Acta Pharmacol. Toxicol. 8, 391 (1952).
Properties: Long prisms from dilute methanol. The crystals are solvated and lose about 8% of their wt in high vacuum, but retain ½ mol H2O. For the hemihydrate, indistinct mp 168-170°, dec 200°. [a]D20 -59 to -60° (methanol). Absorption max (96% ethanol): 300 nm (log e 3.73); (98% H2SO4): 295, 505 nm (E1%1cm 260, 315). Freely sol in the lower alcohols, in ethylene glycol, dioxane, glacial acetic acid. Slightly sol in water, acetone, chloroform, ethyl acetate. Practically insol in ether, petr ether. LD50 in mice (mg/kg): 0.471 s.c.; 0.440 orally (Dybing).
Melting point: mp 168-170°
Optical Rotation: [a]D20 -59 to -60° (methanol)
Absorption maximum: Absorption max (96% ethanol): 300 nm (log e 3.73); (98% H2SO4): 295, 505 nm (E1%1cm 260, 315)
Toxicity data: LD50 in mice (mg/kg): 0.471 s.c.; 0.440 orally (Dybing)
Derivative Type: Tetraacetyl scilliroside
Molecular Formula: C40H52O16
Molecular Weight: 788.83
Percent Composition: C 60.90%, H 6.64%, O 32.45%
Properties: Rosettes of long needles from methanol, mp 199°. Sol in chloroform. The four additional acetyl groups are on the sugar.
Melting point: mp 199°

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