(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → 5,7-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

HRID 40491Notes

Reaction equation

HRID 40491 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]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)=[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].P([O-])(O)(O)=O.[Na+].P([O-])([O-])(O)=O.[Na+].[Na+].O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O>>[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

4

Reactant 3

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 5318997IcariinHCID 86630341Sodium phosphate (Na3(PO4)2)

Product 1

HCID 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

Conditions

Temperature
40 °C

Procedure

Fifty grams icariin were added into sodium dihydrogen phosphate-disodium hydrogen phosphate buffer (pH5.5) and 100 ml β glucose. 100 ml of β glucosidase was added and the solution was heated to 40° C. with stirring for 24 hours in order to remove glucoside. Then stop heating and repeatedly extract with ethyl acetate. The ethyl acetate layer was pooled and dried. Then repeatedly extract with methanol. The HPLC analysis confirmed that the content of pure icariside II 50.1%. Thus extract comprising icariside II is obtained.

Workup

  1. customto remove glucoside
  2. temperatureThen stop heating
  3. extractionrepeatedly extract with ethyl acetate
  4. customdried
  5. extractionThen repeatedly extract with methanol

Sources & evidence

ORD record
ord-28b9f6fe397143c3afbbfc2187eacc8c
Source dataset
uspto-grants-2013_09
Patent number
US08530433B2

Reaction notes

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