HRID1943576

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：COc1ccc(-c2oc3c(CC=C(C)C)c(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)cc(O)c3c(=O)c2O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)cc1

HCID5318997

Icariin

C33H40O15

PRODUCTS

生成物

结构：COc1ccc(-c2oc3c(CC=C(C)C)c(O)cc(O)c3c(=O)c2O)cc1

HCID5318980

Icaritin

C21H20O6

结构：COc1ccc(-c2oc3c(CC=C(C)C)c(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)cc(O)c3c(=O)c2O)cc1

HCID5745470

Baohuoside-1

C27H30O11

结构：COc1ccc(-c2oc3c(CC=C(C)C)c(O)cc(O)c3c(=O)c2O[C@@H]2O[C@H](C)[C@@H](O)[C@H](O)[C@@H]2O)cc1

HCID44587252

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID313

Hydrochloric Acid

ClH

CONDITIONS

反应条件

温度: 80 °C

PROCEDURE

实验过程

20 g of the extract prepared in Example 1 was taken in 1N HCl-50% methanol solution (v/v) in an amount of 20 times (v/w) of its amount and heated to reflux in a water bath at 80° C. for 8 hours to hydrolyze sugars bonded to icariin. The reaction was concentrated under pressure to remove the solvent. The residue was added to ethanol (200 ml), stirred (3 times) and subjected to filtration to remove precipitated salts. The filtrate was concentrated under pressure to obtain a crude product, which was then separated by silica gel column chromatography (chloroform:methanol=8:1 to 4:1) to give 0.9 g of icaritin, 0.7 g of icariside 1 and 0.5 g of icariside II.

WORKUP

后处理

temperatureheated
concentrationThe reaction was concentrated under pressure
customto remove the solvent
additionThe residue was added to ethanol (200 ml)
filtrationsubjected to filtration
customto remove
customprecipitated salts
concentrationThe filtrate was concentrated under pressure
customto obtain a crude product, which
customwas then separated by silica gel column chromatography (chloroform:methanol=8:1 to 4:1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-4859e76ff2f34a30b74f26320d524274
来源数据集: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08394775B2
来源说明: uspto-grants-2013_03

反应 SMILES

[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C:9]2[C:18](=[O:19])[C:17]3[C:16]([OH:20])=[CH:15][C:14]([O:21][C@@H:22]4[O:27][C@H:26]([CH2:28][OH:29])[C@@H:25]([OH:30])[C@H:24]([OH:31])[C@H:23]4[OH:32])=[C:13]([CH2:33][CH:34]=[C:35]([CH3:37])[CH3:36])[C:12]=3[O:11][C:10]=2[C:38]2[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=2)[C@H:5]([OH:46])[C@H:4]([OH:47])[C@H:3]1[OH:48]>Cl>[CH3:36][C:35]([CH3:37])=[CH:34][CH2:33][C:13]1[C:12]2[O:11][C:10]([C:38]3[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=3)=[C:9]([OH:8])[C:18](=[O:19])[C:17]=2[C:16]([OH:20])=[CH:15][C:14]=1[OH:21].[CH3:36][C:35]([CH3:37])=[CH:34][CH2:33][C:13]1[C:12]2[O:11][C:10]([C:38]3[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=3)=[C:9]([OH:8])[C:18](=[O:19])[C:17]=2[C:16]([OH:20])=[CH:15][C:14]=1[O:21][C@@H:22]1[O:27][C@H:26]([CH2:28][OH:29])[C@@H:25]([OH:30])[C@H:24]([OH:31])[C@H:23]1[OH:32].[CH3:1][C@H:2]1[O:7][C@@H:6]([O:8][C:9]2[C:18](=[O:19])[C:17]3[C:16]([OH:20])=[CH:15][C:14]([OH:21])=[C:13]([CH2:33][CH:34]=[C:35]([CH3:37])[CH3:36])[C:12]=3[O:11][C:10]=2[C:38]2[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=2)[C@@H:5]([OH:46])[C@@H:4]([OH:47])[C@@H:3]1[OH:48]