Sarsagenin → Spirostan-3-ol

HRID 1683969Notes

Reaction equation

[CH3:1][C@@H:2]1[CH2:30][O:29][C@@:5]2([O:9][C@H:8]3[CH2:10][C@H:11]4[C@@H:16]5[CH2:17][CH2:18][C@@H:19]6[CH2:24][C@@H:23]([OH:25])[CH2:22][CH2:21][C@:20]6([CH3:26])[C@H:15]5[CH2:14][CH2:13][C@:12]4([CH3:27])[C@H:7]3[C@@H:6]2[CH3:28])[CH2:4][CH2:3]1.C[C@H]1CO[C@@]2(O[C@H]3C[C@H]4[C@@H]5CC[C@H]6C[C@@H](O)CC[C@]6(C)[C@H]5CC[C@]4(C)[C@H]3[C@@H]2C)CC1>>[CH3:28][C@@H:6]1[C@:5]2([O:29][CH2:30][CH:2]([CH3:1])[CH2:3][CH2:4]2)[O:9][C@H:8]2[CH2:10][C@H:11]3[C@@H:16]4[CH2:17][CH2:18][CH:19]5[CH2:24][CH:23]([OH:25])[CH2:22][CH2:21][C@:20]5([CH3:26])[C@H:15]4[CH2:14][CH2:13][C@:12]3([CH3:27])[C@@H:7]12

Participants

Reactant 2

HCID 92095Sarsagenin

HCID 99516Tigogenin

Product 1

HCID 3035446Spirostan-3-ol

Procedure

A variety of structurally related saponins are known, the most variable structural feature being the glycosylation pattern. Saponins also may contain additional modifications, such as the sarasaponins which are saponins with asteroid attached, and saponin structure can be modified by any number of enzymatic, chemical and/or mechanical means known in the art. Saponins from Yucca schidigera contain steroidal saponins with the major sapogenins being sarsapogenin and tigogenin. The sarsaponin yields on hydrolysis, sarsasapogenim (sarsasapogenim 5-beta, 20-betaF, 22-deltaF, 25-betaF; also known as spirostan-3-beta-01 and parigenin), glucose and galaclose. The sarasapogenim has a molecular formula of C27H44O3. Nobel, Park S., Agaves, Oxford Univ. Press, New York, 1994.

Sources & evidence

ORD record: ord-b8838151b1c64c14914843b2a298c31a
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05639794

Reaction notes

Loading…