Daidzin → Malonylgenistin

HRID 847346

Reaktionsgleichung

Reaktionsgleichung von HRID 847346
[CH:1]1[C:6]([C:7]2[C:16](=[O:17])[C:15]3[C:14]([OH:18])=[CH:13][C:12]([O:19][C@@H:20]4[O:25][C@H:24]([CH2:26][OH:27])[C@@H:23]([OH:28])[C@H:22]([OH:29])[C@H:21]4[OH:30])=[CH:11][C:10]=3[O:9][CH:8]=2)=[CH:5][CH:4]=[C:3]([OH:31])[CH:2]=1.C1C(C2C(=O)C3C=CC([O:49][C@@H:50]4[O:55][C@H](CO)[C@@H](O)[C@H:52]([OH:59])[C@H:51]4O)=CC=3OC=2)=CC=C(O)C=1>C(O)C>[CH:5]1[C:6]([C:7]2[C:16](=[O:17])[C:15]3[CH:14]=[CH:13][C:12]([O:19][C@@H:20]4[O:25][C@H:24]([CH2:26][OH:27])[C@@H:23]([OH:28])[C@H:22]([OH:29])[C@H:21]4[OH:30])=[CH:11][C:10]=3[O:9][CH:8]=2)=[CH:1][CH:2]=[C:3]([OH:31])[CH:4]=1.[C:50]([O-:49])(=[O:55])[CH2:51][C:52]([O-:59])=[O:9].[CH:5]1[C:6]([C:7]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][C:12]([O:19][C@@H:20]4[O:25][C@H:24]([CH2:26][O:27][C:52]([CH2:51][C:50]([OH:55])=[O:49])=[O:59])[C@@H:23]([OH:28])[C@H:22]([OH:29])[C@H:21]4[OH:30])=[CH:13][C:14]=3[OH:18])[O:9][CH:8]=2)=[CH:1][CH:2]=[C:3]([OH:31])[CH:4]=1

Komponenten

5

Edukt 2

HCID 107971DaidzinHCID 5281377Genistin

Produkt 2

HCID 15934091MalonylgenistinHCID 86746093Daidzin malonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A chromatography column containing a gel (Sephadex LH-20) 3 cm in diameter and 50 cm tall is prepared. 2.4 g of the impure extract obtained in step iii) diluted with ethanol is introduced into the column. The impure extract is eluted with ethanol at a rate of 2 ml per minute. A total of 17 fractions are obtained, 6 of these fractions containing the malonates of genistin and daidzin. These 6 fractions are subjected to a second chromatography in a column containing octadecyl silane groups attached to silica (Lobar RP-18). A 10% aqueous ethanol solution is used as the eluent at a rate of 2 ml per minute. Two fractions each containing a different product are finally obtained. These fractions are dried under reduced pressure in an evaporator at a temperature of 40° C. 25 mg daidzin malonate and 80 mg genistin malonate, both highly pure (92-98%), are obtained in the form of amorphous solids, the first white in colour and the second pale yellow in colour.

Aufarbeitung

  1. additioncontaining octadecyl silane groups
  2. customTwo fractions each containing a different product are finally obtained
  3. customThese fractions are dried under reduced pressure in an evaporator at a temperature of 40° C

Quellen und Nachweise

ORD-Eintrag
ord-b3bd0190666f4bdaac1acb189c0499d2
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05141746

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