A kind of preparation method of 5,7-dihydroxyflavanone
A technology of naringin and catalyst, applied in the field of preparation of 5,7-dihydroxyflavanone, which can solve the problems of complex steps, expensive raw materials, and increased synthesis costs
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[0026] The invention provides a kind of preparation method of 5,7-dihydroxyflavanone, comprising the following steps:
[0027] Naringin is subjected to a ring-opening reaction in an alkaline solution to obtain acetophenone-4'-neohesperidin from the root bark;
[0028] Under inert gas protection conditions, the root bark acetophenone-4'-neohesperidin, benzaldehyde and catalyst are subjected to ring-closing condensation reaction in an alcohol solvent to obtain naringin analogs; the catalyst is acetic acid and pyrrole a mixture of alkanes;
[0029] The naringin analogue and deglycosylation enzyme are deglycosylated in a buffer solution to obtain 5,7-dihydroxyflavanone.
[0030] In the invention, the naringin is subjected to ring-opening reaction in an alkaline solution to obtain the root bark acetophenone-4'-neohesperidin. In the present invention, the naringin is a dihydroflavonoid compound, which can be extracted from the peels and fruits of pomelo, grapefruit and sour orange...
Embodiment 1
[0058] (1) Add 20g (0.042mol) of naringin into a dry 500mL three-neck flask, add 300mL of 15% KOH (0.805mol) solution, stir until naringin is completely dissolved, and heat to 100°C for ring-opening reaction (heat to reflux start timing when the reaction time is 2 hours, the reaction time is 2 hours, after the reaction is completed, cool to room temperature, adjust the pH of the product system to 6.0 with 36% hydrochloric acid, then heat to above 70°C until all the solids are dissolved, and place it at room temperature to cool and crystallize to obtain a crystal system. The crystalline system was suction-filtered under reduced pressure, the filter cake was washed several times with ice water until the color was off-white, and vacuum-dried at 60°C for 6 hours to obtain 13.13 g of a yellow-white solid with a yield of 80%.
[0059] Gained yellow-white solid is carried out proton nuclear magnetic resonance spectrum detection, and gained data is:
[0060] Yellow-white crystal, m.p....
Embodiment 2
[0075] (1) Add 40g (0.0484mol) of naringin into a dry 1000mL three-necked flask, add 600mL of 15% KOH (1.61mol) solution, stir until naringin is completely dissolved, and heat to 100°C for ring-opening reaction (heat to reflux start timing), the reaction time is 2h, after the reaction is completed, cool to room temperature, adjust the pH of the product system to 6.5 with 36% hydrochloric acid, then heat to above 70°C until all the solids are dissolved, and cool to crystallize at room temperature to obtain a crystal system. The crystalline system was suction-filtered under reduced pressure, the filter cake was washed several times with ice water until the color was off-white, and vacuum-dried at 70° C. for 6.5 h to obtain 26.26 g of a yellow-white solid, with a yield of 80%.
[0076] Gained yellow-white solid is carried out proton nuclear magnetic resonance spectrum detection, and gained data is:
[0077] Yellow-white crystal, m.p.155~159℃
[0078] 1 H-NMR(DMSO,600MHz)δ:12.36...
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