12-08527. Sarverogenin [Archived]
Nomenclature
CAS number: 22146-03-8
(3β,5β,7β,11α)-7,8-Epoxy-3,11,14-trihydroxy-12-oxo-card-20(22)-enolide. C23H30O7; mol wt 418.48.
C 66.01%, H 7.23%, O 26.76%.
Description and references
The aglycone of sarveroside isolated from seeds of Strophanthus spp, Apocynaceae: von Euw et al., Festschrift Prof. Paul Casparis (Zürich, 1949) p 178; Buzas et al., Helv. Chim. Acta 33, 465 (1950); Rothrock et al., J. Am. Chem. Soc. 72, 3827 (1950); von Euw, Reichstein, Helv. Chim. Acta 33, 1006 (1950); Taylor, J. Chem. Soc. 1952, 4832. Structural studies: Taylor, Chem. Ind. (London) 1953, 62; Schindler, Helv. Chim. Acta 39, 375 (1956); Taylor, J. Chem. Soc. C 1966, 790. Revised structure: Fuhrer et al., Helv. Chim. Acta 52, 616 (1969).
Properties
Crystallizes in various forms with different mps, but [according to Taylor, J. Chem. Soc. 1952, 4832] on recrystn from methanol all of these forms yield the one melting at 232-234°. [α]D15 +44.5 ± 2° (c = 1.1683 in methanol); [α]D23 +49.5° (methanol). uv max: 218, 277.5 nm (log ε 4.2, 1.83). Sol in water, methanol, chloroform.Derivative
Diacetate.Properties
Crystals, mp 254-256° (corr). [α]D22 +24.2° (chloroform).Derivative
Dibenzoate.Properties
Cryst powder from methanol, mp 189° (Taylor, loc. cit.); mp 187-191° (micro-block, Rothrock et al., loc. cit.); [α]D23 +30.7 ± 1° (c = 1.301 in acetone). Sol in acetone; slightly sol in methanol.Status
This monograph has been retired and is no longer subject to revision or update.