Icariin → Icaritin

HRID 1943577노트

반응식

HRID 1943577 반응식
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]

참가 물질

6

반응물 2

HCID 5318997IcariinHCID 10942334Sodium Methoxide

생성물 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

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-575a8382b4a746aab3ea7feeb32a2ece
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394775B2

반응 노트

불러오는 중…