Methanol → Genipin

HRID 1089629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1089629
[CH3:1][O:2][C:3]([C:5]1[C@H:10]2[CH2:11][CH:12]=[C:13]([CH2:14][OH:15])[C@H:9]2[C@H:8]([O:16][C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[O:7][CH:6]=1)=[O:4].C(Cl)(Cl)Cl.CO.S(=O)(=O)(O)O>O>[CH3:1][O:2][C:3]([C:5]1[C@H:10]2[CH2:11][CH:12]=[C:13]([CH2:14][OH:15])[C@H:9]2[C@H:8]([OH:16])[O:7][CH:6]=1)=[O:4]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 6212ChloroformHCID 107848Geniposide

Produkt 1

HCID 442424GenipinAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of geniposide (6.5 g) dissolved in distilled water (65 ml), was added β-glucosidase (No.G-0395, β-D-glucoside glucohydrase EC 3.2.1.21) (316.55 mg, 1677.72 units) the mixture was incubated at 37° C. for 4.5 hours. The progress of the reaction was monitored by TLC (chloroform:methanol=8:2, visualized with 50%-sulfuric acid). After the reaction was complete, the reaction solution was extracted several times with ethyl acetate, and subsequently the ethyl acetate layer was concentrated to give genipin as white needles (2.55 g, yield 67.3%).

Aufarbeitung

  1. extractionthe reaction solution was extracted several times with ethyl acetate
  2. concentrationsubsequently the ethyl acetate layer was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-dfa9eb9e0d0049099466fed33b18ae6f
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05078750

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