Icariin → Icaritin

HRID 1943579Notes

Reaction equation

HRID 1943579 reaction equation
[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]>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]

Participants

5

Reactant 1

HCID 5318997Icariin2×

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 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

20 g of the extract prepared in Example 1 was taken in ionized water, sterilized at about 121° C. for 30 minutes, cooled to about 30° C., inoculated with Aspergillus niger KCCM 11885, which had been cultured, in an amount of 5 to 10% based of the total amount of the solution and cultivated at 30° C. for 5 days, preferably 5 days. When icariin completely disappeared by confirming the elimination rate of icariin by thin layer chromatography, the reaction was ended. The resulting culture fluid was centrifuged at 5,000 to 10,000 rpm. The precipitation was washed 3 times with distilled water and centrifuged to obtain precipitation. The precipitation was added to ethanol (200 ml), stirred (3 times) and subjected to filtration to remove residue. 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 0.8 g of icaritin, 0.7 g of icariside 1 and 0.8 g of icariside II.

Workup

  1. waitcultivated at 30° C. for 5 days, preferably 5 days
  2. customThe precipitation
  3. washwas washed 3 times with distilled water
  4. customto obtain
  5. customprecipitation
  6. customThe precipitation
  7. additionwas added to ethanol (200 ml)
  8. filtrationsubjected to filtration
  9. customto remove residue
  10. concentrationThe filtrate was concentrated under pressure
  11. customto obtain a crude product, which
  12. customwas then separated by silica gel column chromatography (chloroform:methanol=8:1 to 4:1)

Sources & evidence

ORD record
ord-6203bed4110248508c7f6471618130cb
Source dataset
uspto-grants-2013_03
Patent number
US08394775B2

Reaction notes

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