Title: Diginatin
CAS Registry Number: 52589-12-5
CAS Name: (3b,5b,12b,16b)-3-[(
O-2,6-Dideoxy-b-D-
ribo-hexopyranosyl-(1?4)-
O-2,6-dideoxy-b-D-
ribo-hexopyranosyl-(1?4)-2,6-dideoxy-b-D-
ribo-hexopyranosyl)oxy]-12,14,16-trihydroxy-card-20(22)-enolide
Molecular Formula: C41H64O15
Molecular Weight: 796.94
Percent Composition: C 61.79%, H 8.09%, O 30.11%
Literature References: Cardiac glycoside from
Digitalis lanata Ehrk.,
Scrophulariaceae: Murphy,
J. Am. Pharm. Assoc. Sci. Ed. 44, 719 (1955); Angliker
et al., Ann. 607, 131 (1957); von Wartburg
et al., Experientia 14, 439 (1958). Acid hydrolysis yields 1 mol diginatigenin + 3 mols D-digitoxose. The sugar residue is attached to the hydroxyl group at C-3 of the aglycon.
Properties: Prisms from acetone, mp 251-253°. Somewhat hygroscopic. [a]D20 +20.5 ±2°; [a]20546 +26.3 ±2° (c = 0.6 in methanol). Absorption max (98% w/w H2SO4): 230, 310, 390, 480, 560 nm (E1%1cm 185, 175, 315, 230, 120). Sol in alcohol, dil alcohol, dioxane; slightly sol in acetone. One part sol in 1000 parts water and in 2000 parts chloroform at 25°.
Melting point: mp 251-253°
Optical Rotation: [a]D20 +20.5 ±2°; [a]20546 +26.3 ±2° (c = 0.6 in methanol)
Absorption maximum: Absorption max (98% w/w H2SO4): 230, 310, 390, 480, 560 nm (E1%1cm 185, 175, 315, 230, 120)
Derivative Type: Acetyldiginatin-a
Molecular Formula: C43H66O16
Molecular Weight: 838.97
Percent Composition: C 61.56%, H 7.93%, O 30.51%
Properties: Flat plates from methanol + chloroform+ ether, mp 199-202°. [a]D20 +30.1° (c = 0.6 in pyridine). uv max: 218 nm (log e 4.1).
Melting point: mp 199-202°
Optical Rotation: [a]D20 +30.1° (c = 0.6 in pyridine)
Absorption maximum: uv max: 218 nm (log e 4.1)
