Icariin → Icaritin

HRID 1943577ノート

反応式

HRID 1943577 の反応式
C[O-].[Na+].[CH3:4][C@@H:5]1[O:10][C@@H:9]([O:11][C:12]2[C:21](=[O:22])[C:20]3[C:19]([OH:23])=[CH:18][C:17]([O:24][C@@H:25]4[O:30][C@H:29]([CH2:31][OH:32])[C@@H:28]([OH:33])[C@H:27]([OH:34])[C@H:26]4[OH:35])=[C:16]([CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39])[C:15]=3[O:14][C:13]=2[C:41]2[CH:42]=[CH:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=2)[C@H:8]([OH:49])[C@H:7]([OH:50])[C@H:6]1[OH:51]>N1C=CC=CC=1>[CH3:39][C:38]([CH3:40])=[CH:37][CH2:36][C:16]1[C:15]2[O:14][C:13]([C:41]3[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=3)=[C:12]([OH:11])[C:21](=[O:22])[C:20]=2[C:19]([OH:23])=[CH:18][C:17]=1[OH:24].[CH3:39][C:38]([CH3:40])=[CH:37][CH2:36][C:16]1[C:15]2[O:14][C:13]([C:41]3[CH:42]=[CH:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=3)=[C:12]([OH:11])[C:21](=[O:22])[C:20]=2[C:19]([OH:23])=[CH:18][C:17]=1[O:24][C@@H:25]1[O:30][C@H:29]([CH2:31][OH:32])[C@@H:28]([OH:33])[C@H:27]([OH:34])[C@H:26]1[OH:35].[CH3:4][C@H:5]1[O:10][C@@H:9]([O:11][C:12]2[C:21](=[O:22])[C:20]3[C:19]([OH:23])=[CH:18][C:17]([OH:24])=[C:16]([CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39])[C:15]=3[O:14][C:13]=2[C:41]2[CH:42]=[CH:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=2)[C@@H:8]([OH:49])[C@@H:7]([OH:50])[C@@H:6]1[OH:51]

参加物

6

反応物 2

HCID 5318997IcariinHCID 10942334Sodium Methoxide

生成物 3

HCID 5318980IcaritinHCID 5745470Baohuoside-1HCID 445872525,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-3-((2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxychromen-4-one

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
80 °C

実験手順

20 g of the extract prepared in Example 1 was taken in dry pyridine (500 ml) and sodium methoxide (powder, 10 g) was added thereto. The solution was 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 0.6 g of icaritin, 0.7 g of icariside 1 and 0.8 g of icariside II.

後処理

  1. temperatureThe solution was heated
  2. concentrationThe reaction was concentrated under pressure
  3. customto remove the solvent
  4. additionThe residue was added to ethanol (200 ml)
  5. filtrationsubjected to filtration
  6. customto remove
  7. customprecipitated salts
  8. concentrationThe filtrate was concentrated under pressure
  9. customto obtain a crude product, which
  10. customwas then separated by silica gel column chromatography (chloroform:methanol=8:1 to 4:1)

出典と根拠

ORDレコード
ord-575a8382b4a746aab3ea7feeb32a2ece
出典データセット
uspto-grants-2013_03
特許番号
US08394775B2

反応ノート

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