Synthesis of calixarenes and their extraction performance for ester catechins

Abstract

A series of extractants (tert-butylcalix[6]arene, tert-butylcalix[8]arene and octeacetate of tert-butylcalix[8]arene) were synthesized, and their structures were identified by IR and ¹H-NMR. The distribution behavior of ester catechins monomer in the aqueous and chloroform two-phase system containing one of calixarene was studied. The influences of different extractants, concentration of tert-butylcalix[8]arene and extraction temperature on the partition coefficients and the separation factors were investigated. The experiment results show that tert-butylcalix[8]arene is the best extractant that forms a more stable supramolecular compound with gallocatechin gallate (GCG) than with epigallocathechin gallate (EGCG) or epicatechin gallate (ECG). When the concentration of p-tert-butylcalix[8]arene is 3.79 mmol/L, the extraction temperature is 4 °C, the partition coefficients of K_GCG, K_ECG, K_EGCG are 0.987, 0.629, 0.449, the separation factors of a₁ and a₂ are 1.450 and 1.596, respectively. The important factors influencing the extraction properties of calixarene are discovered to be its cavity size and hydrogen bonding.

Keywords

calixarene / synthesis / ester catechin monomer / extraction

References

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