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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Efficient Synthesis of Ellagic Acid Salts Using Distillable Ionic Liquids

Shahana A. Chowdhury A , Pamela M. Dean A , R. Vijayaraghavan A and D. R. MacFarlane A B
+ Author Affiliations
- Author Affiliations

A School of Chemistry, Monash University, Clayton Campus, Victoria 3800, Australia.

B Corresponding author. Email: douglas.macfarlane@monash.edu

Australian Journal of Chemistry 64(12) 1624-1627 https://doi.org/10.1071/CH11236
Submitted: 9 June 2011  Accepted: 23 August 2011   Published: 16 September 2011

Abstract

A direct, one pot synthesis of an ellagic acid salt was achieved at room temperature by dimerization of ethyl gallate using N,N-dimethylammonium N′,N′-dimethylcarbamate, a distillable ionic liquid, as solvent.


References

[1]  E. C. Bate-Smith, Phytochemistry 1972, 11, 1153.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE38Xht1ersrY%3D&md5=39e740bf607e62ceb7499abe9b4b6761CAS |

[2]  E. Haslam, Recent Adv. Phytochem. 1979, 12, 475.

[3]  E. M. Daniel, A. S. Krupnick, Y. H. Hew, J. A. Blinder, R. Nims, G. D. Stoner, J. Food Compost. Anal. 1989, 2, 338.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXkvFKgtr0%3D&md5=2ef213aeaafd8f624c45033976b7f93eCAS |

[4]  E. Haslam, in Plant Polyphenols, Vegetable Tannins Revisited (Ed. E. Haslam) 1989 (Cambridge University Press: Cambridge).

[5]  D. A. Vattem, K. Shetty, J. Food Biochem. 2005, 29, 234.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXnslynsLw%3D&md5=6c5a168873b6aaa6d3316ee8b6df794fCAS |

[6]  R. K. Y. Zee-Cheng, C. C. Cheng, Drugs Future 1986, 11, 1029.

[7]  A. U. Rahman, F. N. Ngounou, M. I. Choudhary, S. Malik, T. Makhmoor, M. N. Alam, S. Zareen, D. Lontsi, J. F. Ayafor, B. L. Sondengam, Planta Med. 2001, 67, 335.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  Z. Chen, U. Gundimeda, R. Gopalakrishna, Proc. Annu. Meet. Am. Assoc. Cancer Res. 1997, 38, A1395.

[9]  A. Castonguay, H. U. Gali, E. M. Perchellet, X. M. Gao, M. Boukhar, G. Jalbert, T. Okuda, T. Yoshida, T. Hatano, T. Perchellet, Int. J. Oncol. 1997, 10, 367.
         | 1:CAS:528:DyaK2sXhsVCit7o%3D&md5=75356310d06d87143694cf9593d1dea1CAS |

[10]  D. H. Barch, C. C. Fox, Cancer Res. 1988, 48, 7088.
         | 1:CAS:528:DyaL1MXltVyksw%3D%3D&md5=766c63ceaac301958bac05d240fb8212CAS |

[11]  D. Ahn, D. Putt, L. Kresty, G. D. Stoner, D. Fromm, P. F. Hollenberg, Carcinogenesis 1996, 17, 821.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XislCgtr0%3D&md5=4b795907019c808955c3e58a93130460CAS |

[12]  S. Mandal, G. D. Stoner, Carcinogenesis 1990, 11, 55.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXhtFeqtr0%3D&md5=260cfc9ad3223039595073c331874c0fCAS |

[13]  E. M. Daniel, G. D. Stoner, Cancer Lett. 1991, 56, 117.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXhsFKktLw%3D&md5=6a399ad8b76ee19bfeeb7e663eeab33dCAS |

[14]  J. C. Siglin, D. H. Barch, G. D. Stoner, Carcinogenesis 1995, 16, 1101.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXlvFSku7w%3D&md5=8045a6e01158ff3c4c29fced6890b9e0CAS |

[15]  E. Haslam, Phytochemistry 2007, 68, 2713.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtlykurnJ&md5=6ee3f4857b2c9121cb38287a2b7b3044CAS |

[16]  N. C. Mishra, B. Gold, J. Labelled Comp. Radiopharm. 1990, 28, 927.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXkt1elsw%3D%3D&md5=ed035c8dfaa17cf2194be0110697c74dCAS |

[17]  W. Zeng, Y. H. Heur, T. H. Kinstle, G. D. Stoner, J. Labelled Comp. Radiopharm. 1991, 29, 657.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXkslWhtLg%3D&md5=47463669ba9c976766079042799f4992CAS |

[18]  A. Alam, S. Tsuboi, Tetrahedron 2007, 63, 10454.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtVSku7zF&md5=9fbb8a1a2fc63fc211acdd57713501e0CAS |

[19]  U. P. Kreher, A. E. Rosamilia, C. L. Ratson, J. L. Scott, C. R. Strauss, Org. Lett. 2003, 5, 3107.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXlslKntLY%3D&md5=644e76623579c3e3a951a78ddb87a72cCAS |

[20]  U. P. Kreher, A. E. Rosamilia, C. L. Ratson, J. L. Scott, C. R. Strauss, Molecules 2004, 9, 387.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXntlWltbc%3D&md5=33122d7240595a5aec985538cf552fc7CAS |

[21]  G. Sridhar, T. Gunasundari, R. Raghunathan, Tetrahedron Lett. 2007, 48, 319.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xhtlahu77E&md5=55093d4d90f23e21f6d500f3935e1459CAS |

[22]  S. A. Chowdhury, R. Vijayaraghavan, D. R. MacFarlane, Green Chem. 2010, 12, 1023.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXntVyiurw%3D&md5=3d9352d0289b49487ac4fde9e5b40015CAS |

[23]  W. Schroth, J. Andersch, H. D. Schandler, R. Spitzner, Chem.-Ztg. 1989, 113, 261.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXhsFOlsr4%3D&md5=521ff5317c9d69e9e62b7293996c3574CAS |

[24]  G. M. Sheldrick, Acta Crystallogr. A 2008, 64, 112.
         | Crossref | GoogleScholarGoogle Scholar |