| Identification | Back Directory | [Name]
GITOXIGENIN | [CAS]
545-26-6 | [Synonyms]
GITOXIGENIN
Gitoxygenin
Gitoxigenin,98%
16β-hydroxydigitoxigenin
16BETA-HYDROXYDIGITOXIGENIN
5β,20(22)-Cardenolide-3β,14,16β-triol
3-beta,14,16-trioxycarden-(20:22)-olid
3-beta,14,16-trioxy-digen-(20:22)-olid
cardogenen-(20:22)-triol-(3-beta,14,16)
3β,14,16β-Trihydroxy-5β,20(22)-cardenolide
5BETA,20[22]-CARDENOLIDE-3BETA,14,16BETA-TRIOL
3β,14,16β-Trihydroxy-5β,14β-card-20(22)-enolide
3BETA,14,16BETA-TRIHYDROXY-5BETA,20[22]-CARDENOLIDE
20(22),5BETA-CARDENOLID-3BETA, 14BETA, 16BETA-TRIOL
3-beta,14,16-beta-trihydroxy-5-beta-card-20(22)-enolid
3β,14,16β,21-Tetrahydroxy-20(22)-norcholenic acid lactone
delta(20,22)-2,14,16,21-tetrahydroxynorcholenicacidlactone
3,14,16-trihydroxy-,(3-beta,5-beta,16-beta)-card-20(22)-enolid
3BETA,14,16BETA,21-TETRAHYDROXY-20(22)-NORCHOLENIC ACID LACTONE
3-beta,14,16-beta-trihydroxy-5-beta,14-beta-card-20(22)-enolide
16β-Hydroxydigitoxigenin, 3β,14,16β-Trihydroxy-5β,20(22)-cardenolide, 5β,20(22)-Cardenolide-3β,14,16β-triol, 3β,14,16β,21-Tetrahydroxy-20(22)-norcholenic acid lactone | [EINECS(EC#)]
208-886-2 | [Molecular Formula]
C23H34O5 | [MDL Number]
MFCD00021174 | [MOL File]
545-26-6.mol | [Molecular Weight]
390.51 |
| Chemical Properties | Back Directory | [Appearance]
light yellow flakes | [Melting point ]
~230 °C
| [Boiling point ]
435.71°C (rough estimate) | [density ]
1.0639 (rough estimate) | [refractive index ]
1.6120 (estimate) | [storage temp. ]
−20°C
| [pka]
14.56±0.70(Predicted) | [Merck ]
13,4445 |
| Hazard Information | Back Directory | [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.] |
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