Methanol → Genipin

HRID 1089629Notes

Reaction equation

HRID 1089629 reaction equation
[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]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 6212ChloroformHCID 107848Geniposide

Product 1

HCID 442424GenipinYield 67.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-dfa9eb9e0d0049099466fed33b18ae6f
Source dataset
uspto-grants-1992_01
Patent number
US05078750

Reaction notes

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