Icariin → Icaritin

HRID 1943578ノート

反応式

HRID 1943578 の反応式
[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]>C(O)(=O)C.O>[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]

参加物

6

反応物 1

HCID 5318997Icariin

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 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

反応条件

温度
37 °C

実験手順

20 g of the extract prepared in Example 1 was taken in 100 ml of 0.1M acetic acid buffer solution (pH 4.5) and 2.5 g of enzymes (0.5 g of hesperidinase, 0.5 g of naringinase, 0.5 g of cellulase, 0.2 g of β-glucuronidase, 0.5 g of β-galactosidase, 0.3 g of amyloglucosidase; supplied by Sigma) was added thereto. The solution was stirred in a water bath at 37° C. for 48 hours. When icariin completely disappeared by periodically confirming by thin layer chromatography, the reaction was finished by heating in hot water (80 to 100° C.) for 10 minutes. 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 1.1 g of icaritin, 1.2 g of icariside 1 and 0.9 g of icariside II.

後処理

  1. addition2.5 g of enzymes (0.5 g of hesperidinase, 0.5 g of naringinase, 0.5 g of cellulase, 0.2 g of β-glucuronidase, 0.5 g of β-galactosidase, 0.3 g of amyloglucosidase; supplied by Sigma) was added
  2. concentrationThe reaction was concentrated under pressure
  3. customto remove the solvent
  4. additionThe residue was added to ethanol (200 ml)
  5. stirringstirred (3 times)
  6. filtrationsubjected to filtration
  7. customto remove
  8. customprecipitated salts
  9. concentrationThe filtrate was concentrated under pressure
  10. customto obtain a crude product, which
  11. 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-fb67d5092ed7480a8f73682e002f04c1
出典データセット
uspto-grants-2013_03
特許番号
US08394775B2

反応ノート

読み込み中…