Title: Gitoxigenin
CAS Registry Number: 545-26-6
CAS Name: (3b,5b,16b)-3,14,16-Trihydroxycard-20(22)-enolide
Additional Names: D20,22-3,14,16,21-tetrahydroxynorcholenic acid lactone
Molecular Formula: C23H34O5
Molecular Weight: 390.51
Percent Composition: C 70.74%, H 8.78%, O 20.49%
Literature References: The aglycon of gitoxin. By refluxing gitoxin in a mixture of water + alcohol + HCl: Smith, J. Chem. Soc. 1931, 23. Structure: Jacobs, Elderfield, J. Biol. Chem. 100, 671 (1933); Elderfield, Chem. Rev. 17, 217 (1935); Henderson, Chen, J. Med. Pharm. Chem. 5, 988 (1962). Configuration: Moore, Helv. Chim. Acta 37, 659 (1954); Repke, Klesczewski, Arch. Exp. Pathol. Pharmakol. 239, 131 (1960). Cf. ref under Digoxigenin.
Derivative Type: Sesquihydrate
Properties: Plates from dil alc. After drying at 100° in vacuo mp 234°. [a]54520 +38.5° (c = 0.68 in methanol). Absorption max (96% H2SO4): 310, 485, 520 nm. Slightly sol in alcohol, acetone, ethyl acetate. Treatment with alcoholic HCl yields digitaligenin with loss of 2H2O.
Melting point: mp 234°
Optical Rotation: [a]54520 +38.5° (c = 0.68 in methanol)
Absorption maximum: Absorption max (96% H2SO4): 310, 485, 520 nm
Derivative Type: 3,16-Diacetylgitoxigenin
Properties: mp 249-250°.
Melting point: mp 249-250°
Derivative Type: 3,16-Dibenzoylgitoxigenin
Properties: mp 262°.
Melting point: mp 262°
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