Coumarin Compounds - Extraction and Separation Coumarin Compound Extraction and Separation Technology Extraction and Separation Technology Extraction and Separation Chromatographic Separation Method Solvent Extraction Method Solvent Extraction Method Steam Distillation Method Alkali Dissolution Acid Precipitation Method 1. Extraction method - Solvent method often uses ethanol to extract coumarin glycosides or aglycones. Strongly lipophilic aglycones: have greater solubility in chloroform, diethyl ether or ethyl acetate. Highly polar glycosides: soluble in methanol or hot water. Medicinal materials contain a variety of coumarins with different polarities: a systematic solvent extraction method can be used, such as petroleum ether, benzene, diethyl ether, ethyl acetate, acetone and ethanol for sequential extraction. Systemic solvent extraction method. Petroleum ether reflux extraction. Petroleum ether liquid is recovered to a small volume of concentrated liquid. Place and crystallize the coarse crystals. Cold petroleum ether washes and crystallizes (if possible, a mixture is mixed). Further separate the monomer residue ether liquid. Ether reflux extraction recovers and separates the monomer residue ethanol. Extract the ethanol liquid to recover and separate the coarse powder of coumarin glycoside medicinal materials (lipophilic coumarin) (weakly lipophilic coumarin). Some small-molecule coumarin compounds are volatile and can be combined with non-volatile ones by steam distillation. Separation of sexual components. For example: Separation of hesperiolein from orange oil 1. Extraction method - steam distillation method. The residual oil of the orange peel distillate is heated and dissolved in ethanol. The crude product is placed in the ethanol liquid and recrystallized with ethanol, ether or petroleum ether (orange peel oil 1. Extraction method - Principle of alkali solution and acid precipitation method: The lactone ring nature of coumarin is saponified into salt in alkali solution and restored to lactone after adding acid. Note: 1. When heating the alkali solution to open the ring, pay attention to the concentration of the alkali solution and the heating time, otherwise it will cause a degradation reaction and destroy the coumarin, or cause the coumarin to open the ring and fail to ring. 2. Coumarin that is sensitive to acid and alkali may obtain secondary products by this method. 2. Separation method Solvent extraction method Chromatographic separation method Taking advantage of the different polarity characteristics of coumarin glycosides and aglycones, use solvents with different polarities to extract them sequentially and divide them into parts with different polarities. Coumarins with similar structures are separated and purified using silica gel column chromatography. Component A Component F Coumarins Component B Component C Component E Component D