Icariin → Icaritin

HRID 1943577Notes

Reaction equation

HRID 1943577 reaction equation
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]

Participants

6

Reactant 2

HCID 5318997IcariinHCID 10942334Sodium Methoxide

Product 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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-575a8382b4a746aab3ea7feeb32a2ece
Source dataset
uspto-grants-2013_03
Patent number
US08394775B2

Reaction notes

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