Icariin → Icaritin

HRID 1943576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943576
[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]>Cl>[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]

Komponenten

5

Edukt 1

HCID 5318997Icariin

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

20 g of the extract prepared in Example 1 was taken in 1N HCl-50% methanol solution (v/v) in an amount of 20 times (v/w) of its amount and 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 0.9 g of icaritin, 0.7 g of icariside 1 and 0.5 g of icariside II.

Aufarbeitung

  1. temperatureheated
  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)

Quellen und Nachweise

ORD-Eintrag
ord-4859e76ff2f34a30b74f26320d524274
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394775B2

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