Selective deacylation method for polyphenol esters
A deacylation and selective technology, applied in the field of functional food and medicine, can solve the problems of inability to achieve directional regulation and potential environmental harm, and achieve the effects of avoiding toxic and corrosive reagents, strong selectivity, and mild reaction conditions.
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Embodiment 1
[0031] Weigh phloroglucinol triacetate (CAS number: 2999-40-8, 252.0mg / 1mmoL) in a round bottom flask, add alanine (100.0mg / 1.12mmoL) and N,N-dimethyl formamide / water (2mL / 2mL), and stir on a magnetic stirrer to dissolve the sample. Slowly add NaHCO with stirring 3 (113.0 mg / 1.35 mmoL). The reaction was placed at a constant temperature of 30° C. to react overnight, and the progress of the reaction was detected on a thin-layer silica gel plate. The end of the reaction was extracted with ethyl acetate, and washed three times with water, and the resulting organic phase was washed with anhydrous MgSO 4 The powder was dried, and the organic solvent was evaporated and removed under reduced pressure with a rotary evaporator to obtain a yield of phloroglucinol mono-deesterification product of 82%.
[0032] Phloroglucinol mono-deesterification product structure determination data: 1 H NMR (400MHz, CDCl 3 ) δ6.84 (d, J=0.9Hz, 1H), 6.45(s, 2H), 2.28 (d, J=0.7Hz, 6H). The results of...
Embodiment 2
[0038] Weigh resorcinol diacetate (CAS number: 108-58-7, 194.0mg / 1mmoL) in a round bottom flask, add alanine (115.0mg / 1.29mmoL) and N,N-dimethyl Acetamide / water (2mL / 2mL), and stir on a magnetic stirrer to dissolve the sample. Slowly add Na with stirring 2 CO 3 (140.0 mg / 1.32 mmoL). The reaction was placed at a constant temperature of 30° C. to react overnight, and the progress of the reaction was detected on a thin-layer silica gel plate. The end of the reaction was extracted with ethyl acetate, and washed three times with water, and the resulting organic phase was washed with anhydrous MgSO 4 The powder was dried, and the organic solvent was evaporated under reduced pressure with a rotary evaporator to obtain a yield of resorcinol mono-deesterification product of 85%.
[0039] Structural determination data of resorcinol mono-deesterification product: 1 H NMR (400MHz, CDCl 3 )δ7.22 (m, 1H), 6.73 (m, 3H), 2.29 (s, 3H). The results of mass spectrometry showed that its mo...
Embodiment 3
[0041] Weigh phloroglucinol triacetate (252.0mg) into a round bottom flask, add glycine (95.0mg) and N,N-dimethylformamide / water (2mL / 2mL), and place on a magnetic stirrer Stir to dissolve the sample. Slowly add NaHCO with stirring 3(104.0 mg). The reaction was placed at a constant temperature of 30° C. to react overnight, and the progress of the reaction was detected on a thin-layer silica gel plate. The end of the reaction was extracted with ethyl acetate, and washed three times with water, and the resulting organic phase was washed with anhydrous MgSO 4 The powder was dried, and the organic solvent was evaporated under reduced pressure with a rotary evaporator to obtain a phloroglucinol mono-deesterified product with a yield of 90%.
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