Synthesis Of A Novel Chiral Stationary Phase Based On Dehydroabietic Acid And Its Application

Dehydroabietic acid is a tricyclic diterpenoid compound,isolated from dehydrogenated rosin.It contains a rigid framework incorporating an aromatic ring and three chiral centers:C-4,C-5,C-10.There is a carboxyl group at the C-4 position,which is a quaternary carbon atom.For the rigid structure and the chiral recognition of the carboxyl group at the quaternary of dehydroabietic acid,it has been successfully applied to the resolution of the chiral compounds and it is an excellent chiral resolution reagent.In recent years,chromatography spilt method has become the hot spots and cutting-edge of the chiral separation field and the chiral stationary phases(CSP)for high-performance liquid chromatography(HPLC)develops rapidly.A part of the CSPs is prepared through the chiral resolving agent bonding to the silica gel's surface by chemical bonds.From this angle,the experiment studies how to prepare the dehydroabietic acid-silica gel chiral resolving agent by the bonding of dehydroabietic acid and silica gel.In this experiment,extracting isolated dehydroabietic acid from disproportionated rosin with the method of amination.The isolated dehydroabietic acid is raw material making up four CSPs.Dehydroabietic chloride aminopropyl chiral stationary phase(DA-CSP),dehydroabietic chlorobutyric aminopropyl chiral stationary phase(DChA-CSP),dehydroabietic butanone chloride aminopropyl chiral stationary phase(DBA-CSP),dehydroabietic benzyl chloride aminopropyl chiral stationary phase(DBeA-CSP),and the effect of various factors,such as solvent system and reaction time,on the synthesis experiment was investigated,the optimization of experimental condition has been optimized.Two CSPs(DA-CSP and DChA-CSP)with higher load rate have been characterized by a variety of methods.Dehydroabietic chloride aminopropyl chiral stationary phase(DA-CSP)with the highest load rate was tested.Experimental results demonstarted that this CSP has chiral selectivity of the Propranolol enantiomer,that is,the adsorption of he R-propranolol is easily.Packing dehydroabietic chloride aminopropyl chiral stationary phase(DA-CSP)and dehydroabietic chlorobutyric aminopropyl chiral stationary phase(DChA-CSP)respectively,the performance of the chromatographic column and preliminary resolution of chiral drugs and was studied.The results show that this CSP has good column efficiency,and has certain chiral separation effect on bupivacaine enantiomer.