Advertisement

Journal of Central South University of Technology

, Volume 14, Issue 6, pp 798–802 | Cite as

Synthesis of calixarenes and their extraction performance for ester catechins

  • Yi Jian-min  (易健民)
  • Huang Sai-jin  (黄赛金)
  • Tang Ke-wen  (唐课文)Email author
  • Huang Ke-long  (黄可龙)
Article

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 KGCG, KECG, KEGCG 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.

Key words

calixarene synthesis ester catechin monomer extraction 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. [1]
    ATWOOD J L, KOUTSANTNIS G A, RASTON C L. Purification of C60 and C70 by selective complexation with calixarenes[J]. Nature, 1994, 368: 229–231.CrossRefGoogle Scholar
  2. [2]
    BARALAT N, BURGARD M, ASFARI Z, et al. Solevnt extraction of alkaline-earth ions by dicarboxylated calix[4]arenes[J]. Polyhedron, 1998, 17(20): 3649–3656.CrossRefGoogle Scholar
  3. [3]
    SHIMOJO K, OSHIMA T, GOTO M. Calix[6]arene acid extraction spicificity with respect to nucleaobases[J]. Analytica Chimica Acta, 2004, 521: 163–171.CrossRefGoogle Scholar
  4. [4]
    LIU Yu, YANG En-cui, CHEN Yong, et al. Molecular selective binding of pyridinium guest ions by water-soluble calix[4]arenas eur[J]. J Org Chem, 2005, 21: 4581–4588.Google Scholar
  5. [5]
    SHIMOJO K, GOTO M, Synergistic extraction of nucleobase by the combination of calixarene and D2EHPA[J]. Separation and Purification Technology, 2005, 44: 175–180.CrossRefGoogle Scholar
  6. [6]
    OSHIMA T, GOTO M, FURUSAKI S. Extraction behavior of amino acids by calix[6]arene carboxylic acid derivatives[J]. J Inclusion Phenom Macrocyclic Chem, 2002, 43: 77–86.CrossRefGoogle Scholar
  7. [7]
    MUTIHAC L, TUDORESCU A, BUSCHMANN J H, et al. Some aspects of extract ability and transport of amino acid esters by calixarenes[J]. J Inclusion Phenom Macrocyclic Chem, 2003, 47: 123–128.CrossRefGoogle Scholar
  8. [8]
    OSHIMA T, GOTO M, FURUSAKI S. Complex formation of cytochrome with a calixarene carboxylic acid derivative: A novel solubilization method for biomolecules in organic media[J]. Biomacromolecules, 2002, 3: 438–444.CrossRefGoogle Scholar
  9. [9]
    STONER G D, MUKHTAR H. Polyphenols as cancer chemopreventive agent[J]. J Cell Biochem, 1995, 22: 169–180.CrossRefGoogle Scholar
  10. [10]
    SAIJIO R. Isolation and chemical structure of two new catechins[J]. Nippon Kaishi Nigeikagaku, 1989, 63(4): 870–880.Google Scholar
  11. [11]
    CAO Xue-li, TIAN Yu, ZHANG Tian-you. Preparation of ester catechins monomer by high-speed counter current chromatography: CN, 99109031.4[P]. 2000-12-20. (in Chinese)Google Scholar
  12. [12]
    ZHONG Shi-an, ZHOU Chun-shan, YANG Juan-yu. Separation and preparation of ester catechins by high performance liquid chromatography[J]. Chemical World, 2003(5): 237–249. (in Chinese)Google Scholar
  13. [13]
    YI Jian-min, LI Bao-rong, TANG Ke-wen, et al. Extraction of ester catechins with gallate ester[J]. J Cent South Univ: Science and Technology, 2006, 37(6): 1127–1131. (in Chinese)Google Scholar
  14. [14]
    TANG Ke-wen, ZHOU Chun-shan, ZHONG Shi-an, et al. Study on adsorption of tea polyphenol and caffine with polyamide resin[J]. Chinese J Spectroscopy and Spectral Analysis, 2003, 23(1): 143–145. (in Chinese)Google Scholar
  15. [15]
    GUTSCHE C D, DHAWAN B. Calixarene. 4. The synthesis characterization, and properties of the calixarene from p-tert-butylphenol[J]. J Am Chem Soc, 1981, 103(13): 3782–3792.CrossRefGoogle Scholar
  16. [16]
    IWAMOTO K, SHINKAI S. Syntheses and ion selectivity of an conformational isomers of tetrakis ((ethoxycarbonyl) methoxy) calix[4]arene[J]. J Org Chem, 1992, 57: 7066–7073.CrossRefGoogle Scholar
  17. [17]
    SHINKAI S. Bioorganic Chemistry Fronties 1[M]. DUGAS H. Berlin: Springer-Verlag Heidelberg, 1990.Google Scholar
  18. [18]
    TANG Ke-wen, ZHOU Chun-shan. Enantoselective extraction of terbutaline enantiomers by lipophilic tartaricacid[J]. J Cent South Univ Technol, 2003, 10(1): 44–48.CrossRefGoogle Scholar

Copyright information

© Published by: Central South University Press, Sole distributor outside Mainland China: Springer 2007

Authors and Affiliations

  • Yi Jian-min  (易健民)
    • 1
    • 2
  • Huang Sai-jin  (黄赛金)
    • 2
  • Tang Ke-wen  (唐课文)
    • 1
    Email author
  • Huang Ke-long  (黄可龙)
    • 2
  1. 1.Department of Chemistry and Chemical EngineeringHunan Institute of Science and TechnologyYueyangChina
  2. 2.School of Chemistry and Chemical EngineeringCentral South UniversityChangshaChina

Personalised recommendations