Chemical Properties
light yellow flakes
Uses
Gitoxigenin is a related compound of Digitoxigenin, which has been used in a study to assess its stereochemical effects in cancer cytotoxicity. Digitoxigenin has also been used in a study to investigate the advantage of gold(I)-catalyzed glycosidation of glycosyl o-alkyl benzoates to assemble digitoxin.
Definition
ChEBI: Gitoxigenin is a 3beta-hydroxy steroid, a 14beta-hydroxy steroid and a 16beta-hydroxy steroid. It derives from a hydride of a 5beta-cardanolide.
Biochem/physiol Actions
Structure-activity relationships for 16β-substituted digitoxigenins as inhibitors of Na+/K+ ATPases.
Purification Methods
Recrystallisation of gitoxigenin from aqueous EtOH produces plates of the sesquihydrate which dehydrate on drying at 100o in vacuo. It also recrystallises from Me2CO/MeOH and from EtOAc (the crystals contain 1 mol of EtOAc) with [] D +24.8o (c 1, dioxane). It has UV with max at 310, 485 and 520nm in 96% H2SO4. On heating with ethanolic HCl it yields digitaligenin with loss of H2O. [Smith J Chem Soc 23 1931, Beilstein 8 IV 2456.]
