Scillaren
Title: Scillaren
CAS Registry Number: 11003-70-6
Literature References: A mixture of glycosides, scillaren A and B in the proportions in which they occur in fresh squill, Urginea (Scilla) maritima (L.) Baker, Liliaceae, about 2 parts of A to 1 part of B. Isolation of scillaren and separation of A and B: Stoll et al., Helv. Chim. Acta 16, 703 (1933).
Properties: Granular, very bitter powder. On drying in high vacuum at 78° for 15 hrs it loses not more than 6% of its wt. [a]D20 -25 to -35° (0.5 g in 25 ml of 75% w/w alcohol). One gram dissolves in 3000 ml water, in 5 ml abs alcohol, in 5 ml methanol. Practically insol in ether and chloroform. Aq solns are neutral to litmus.
Optical Rotation: [a]D20 -25 to -35° (0.5 g in 25 ml of 75% w/w alcohol)
 
Derivative Type: Scillaren A
CAS Registry Number: 124-99-2
CAS Name: (3b)-3-[(6-Deoxy-4-O-b-D-glucopyranosyl-a-L-mannopyranosyl)oxy]-14-hydroxybufa-4,20,22-trienolide
Additional Names: glucoproscillaridin A; transvaalin
Molecular Formula: C36H52O13
Molecular Weight: 692.79
Percent Composition: C 62.41%, H 7.57%, O 30.02%
Literature References: Characterization and structure: Stoll et al., Z. Physiol. Chem. 222, 24 (1933); Helv. Chim. Acta 17, 641, 1334 (1934); 18, 82, 120, 401, 644, 1247 (1935); 24, 1380 (1941); Zoller, Tamm, ibid. 36, 1744 (1953). Pharmacology: K. K. Chen, F. G. Henderson, J. Pharmacol. Exp. Ther. 111, 365 (1954); G. Vogel, E. Kluge, Arzneim.-Forsch. 11, 848 (1961).
Properties: Very bitter taste. Two crystal modifications from methanol: prisms, mp 184-186°; leaflets, mp 208-211°. [a]D23 -71.9° (c = 1.011 in methanol). Tendency to form solvated crystals. Six-sided plates, tablets contg 1 mol CH3OH + 1 mol H2O from dil methanol, mp 230-240°. Anhydr from 85% alcohol, solvent-free: mp 270°; [a]D20 -72 to -78° (c = 1 to 3 in 75% alcohol), [a]D20 -73.8°. Soluble in 350 parts alcohol, in 80 parts methanol, in 40 parts dil alcohol (4 vols ethanol + 1 vol water). Practically insol in chloroform, ether. Sparingly sol in water. LD50 i.v. in rats: 15.5 mg/kg (Vogel, Kluge).
Melting point: mp 184-186°; mp 208-211°; mp 230-240°; mp 270°
Optical Rotation: [a]D23 -71.9° (c = 1.011 in methanol); [a]D20 -72 to -78° (c = 1 to 3 in 75% alcohol); [a]D20 -73.8°
Toxicity data: LD50 i.v. in rats: 15.5 mg/kg (Vogel, Kluge)
 
Derivative Type: Scillaren B
Properties: An undefined water-sol mixture of glucosides remaining after extraction of scillaren A. Amorphous, granular powder. Very bitter taste. Scillaren B dried in a high vacuum at 78°C for 15 hrs loses not more than 5% of its weight. Completely dried scillaren B contains approx 99.5% active glycosidal substance. [a]D20 +35 to 41° (0.5 g in 25 ml of 75% w/w ethanol). Freely sol in water. Soluble in alcohol, methanol (about 1 in 5); very slightly sol in chloroform (about 1 in 10,000). Practically insol in ether. Aq solns are neutral to litmus.
Optical Rotation: [a]D20 +35 to 41° (0.5 g in 25 ml of 75% w/w ethanol)
 
Therap-Cat: Cardiotonic.
Keywords: Cardiotonic.

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