C/C=C(/C([O:7][C@@H:8]1[C:69]([CH3:71])([CH3:70])[CH2:68][CH:67]2[C@@:10]([CH2:74][OH:75])([C@H:11]([OH:73])[CH2:12][C@@:13]3([CH3:72])[C@:18]4([CH3:66])[CH2:19][CH2:20][CH:21]5[C@:26]([CH2:28][OH:29])([CH3:27])[CH:25]([O:30][C@@H]6O[C@H](C(O)=O)[C@@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)[CH2:24][CH2:23][C@:22]5([CH3:65])[CH:17]4[CH2:16][CH:15]=[C:14]32)[C@H:9]1[O:76]C(C)=O)=O)\C.C/C=C(\C(O[C@@H:87]1[C:148](C)([CH3:149])[CH2:147][CH:146]2[C@@:89](CO)([C@H:90]([OH:152])[CH2:91][C@@:92]3([CH3:151])[C@:97]4([CH3:145])[CH2:98][CH2:99][CH:100]5[C@:105]([CH2:107][OH:108])([CH3:106])[CH:104]([O:109][C@@H]6O[C@H](C(O)=O)[C@@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)[CH2:103][CH2:102][C@:101]5([CH3:144])[CH:96]4[CH2:95][CH:94]=[C:93]32)[C@H:88]1[O:155]C(C)=O)=O)/C.Cl.[CH2:160]([OH:162])[CH3:161]>>[CH3:70][C:69]1([CH3:71])[CH:8]([OH:7])[CH:9]([OH:76])[C:10]2([CH2:74][OH:75])[CH:67]([C:14]3[C:13]([CH3:72])([CH2:12][CH:11]2[OH:73])[C:18]2([CH3:66])[CH:17]([C:22]4([CH3:65])[CH:21]([CH2:20][CH2:19]2)[C:26]([CH2:28][OH:29])([CH3:27])[CH:25]([OH:30])[CH2:24][CH2:23]4)[CH2:16][CH:15]=3)[CH2:68]1.[CH3:144][C@@:101]12[C@H:96]3[CH2:95][CH:94]=[C:93]4[C@@H:146]5[CH2:147][C:148]([CH3:149])([CH3:87])[C@@H:161]6[O:152][C@@H:90]([C@@:89]5([CH2:88][OH:155])[C@H:160]6[OH:162])[CH2:91][C@@:92]4([CH3:151])[C@:97]3([CH3:145])[CH2:98][CH2:99][C@H:100]1[C@:105]([CH2:107][OH:108])([CH3:106])[C@@H:104]([OH:109])[CH2:103][CH2:102]2In Justus Liebigs Annalen der Chemie 1963, 669, 183-188 Kuhn R. and Loew I. described the hydrolysis of escin in the solution of 4 N hydrochloric acid in ethanol, the separation of the intermediate, and its subsequent hydrolysis under basic conditions with potassium hydroxide in methanol. The hydrolysis products were separated by chromatography on silica gel, yielding protoescigenin and escigenin.
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