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

Improved Extraction Yield of Citral from Lemon Myrtle Using a Cellulose-Dissolving Ionic Liquid

Koki Munakata A , Masahiro Yoshizawa-Fujita A , Masahiro Rikukawa A and Toyonobu Usuki A B
+ Author Affiliations
- Author Affiliations

A Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan.

B Corresponding author. Email: t-usuki@sophia.ac.jp

Australian Journal of Chemistry 70(6) 699-704 https://doi.org/10.1071/CH16460
Submitted: 4 August 2016  Accepted: 7 October 2016   Published: 4 November 2016

Abstract

Lemon myrtle is the richest natural source of citral, which has potential medicinal applications. In this study, citral was extracted from lemon myrtle using cellulose-dissolving ionic liquids (ILs), 1-ethyl-3-methylimidazolium methylphosphonate ([C2mim][(MeO)(H)PO2]), N,N-diethyl-N-methyl-N-(2-methoxyethyl)ammonium chloride ([DEME]Cl), and N,N-diethyl-N-methyl-N-(2-methoxyethyl)ammonium 2-methoxyacetate ([DEME][MOAc]). The extraction yield of citral obtained using ILs was up to 2.1 times higher than that obtained using ethanol. The ILs could be recycled and reused nine times for the extraction of citral. The present method provides a greener process when compared with conventional approaches and may be applicable for the extraction of other natural products.


References

[1]  A. Buchaillot, N. Caffin, B. Bhandari, Drying Technol. 2009, 27, 445.
         | CrossRef | 1:CAS:528:DC%2BD1MXjtF2ktb0%3D&md5=0d8910d5dc968f4dde80231c396c3292CAS |

[2]  T. Horn, A. Barth, M. Rühle, A. Häser, G. Jürges, P. Nick, Eur. Food Res. Technol. 2012, 234, 853.
         | CrossRef | 1:CAS:528:DC%2BC38XlsFeqtrc%3D&md5=6e9b8436dd3f1751d49cd258c8e14f13CAS |

[3]  For example, lemon myrtle leaves are used to make tea: Chikiriya, http://www.kyo-chikiriya.com/english/ (accessed 4 August 2016).

[4]  E. V. Lassak, Revision of Backhousia citriodora Essential Oil Standard. RIRDC Publication 11, No. 11/137 2012 (Rural Industries Research and Development Corporation: ACT)

[5]  B. E. Burke, J. E. Baillie, R. D. Olson, Biomed. Pharmacother. 2004, 58, 245.
         | CrossRef | 1:CAS:528:DC%2BD2cXks1Wksrg%3D&md5=96bc38ffe0ec293a498a311c9373a2f8CAS | 15183850PubMed |

[6]  S. Pattnaik, V. R. Subramanyam, M. Bapaji, C. R. Kole, Microbios 1997, 89, 39.
         | 1:CAS:528:DyaK2sXkt1emtbw%3D&md5=0a6962d2f0af984ba25d1df4dc1162d5CAS | 9218354PubMed |

[7]  W. Chaouki, D. Y. Leger, B. Liagre, J. L. Beneytout, M. Hmamouchi, Fundam. Clin. Pharmacol. 2009, 23, 549.
         | CrossRef | 1:CAS:528:DC%2BD1MXht1SrtL7M&md5=ebf3f272b1d9791262084d7ce51b8fdaCAS | 19656204PubMed |

[8]  H. Xia, W. Liang, Q. Song, X. Chen, X. Chen, J. Hong, Cytotechnology 2013, 65, 49.
         | CrossRef | 1:CAS:528:DC%2BC3sXkvVersQ%3D%3D&md5=92c36a53ea121dcc5df74c0d566f66f2CAS | 22573288PubMed |

[9]  H. Ohno, Y. Fukaya, Chem. Lett. 2009, 38, 2.
         | CrossRef | 1:CAS:528:DC%2BD1MXht1Wms78%3D&md5=671be3b75b623b3ec07494975be10af8CAS |

[10]  N. Sun, H. Rodríquez, M. Rahman, R. D. Rogers, Chem. Commun. 2011, 47, 1405.
         | CrossRef | 1:CAS:528:DC%2BC3MXot1Ciuw%3D%3D&md5=f66516235eadef60eb02408bc0a01e40CAS |

[11]  Y. Dai, J. van Spronsen, G.-J. Witkamp, R. Verpoorte, Y. H. Choi, J. Nat. Prod. 2013, 76, 2162.
         | CrossRef | 1:CAS:528:DC%2BC3sXhslaksb7O&md5=093b73d6e566a89523212e55035118c3CAS | 24188074PubMed |

[12]  Y. Fukaya, K. Hayashi, M. Wada, H. Ohno, Green Chem. 2008, 10, 44.
         | CrossRef | 1:CAS:528:DC%2BD1cXhtlCruw%3D%3D&md5=c5fc65eac35ccb1547b9bf0736053e09CAS |

[13]  T. Usuki, N. Yasuda, M. Yoshizawa-Fujita, M. Rikukawa, Chem. Commun. 2011, 47, 10560.
         | CrossRef | 1:CAS:528:DC%2BC3MXhtFyqtLzE&md5=27e31f0087e516a60c6d5f8090792344CAS |

[14]  S. Onda, T. Usuki, M. Yoshizawa-Fujita, M. Rikukawa, Chem. Lett. 2015, 44, 1461.
         | CrossRef | 1:CAS:528:DC%2BC28Xjt1GhsLY%3D&md5=7860243a2dd8978723d7987f8ce5ec69CAS |

[15]  K. Bica, P. Gaertner, R. D. Rogers, Green Chem. 2011, 13, 1997.
         | CrossRef | 1:CAS:528:DC%2BC3MXpslGiu7w%3D&md5=d5cefd0642ac5faef44430484436fb54CAS |

[16]  T. Liu, X. Sui, R. Zhang, L. Yang, Y. Zu, L. Zhang, Y. Zhang, Z. Zhang, J. Chromatogr. A 2011, 1218, 8480.
         | CrossRef | 1:CAS:528:DC%2BC3MXhtl2rtrnI&md5=56009f27f2bfe0f566c26c5a3f12d9ccCAS | 21999917PubMed |

[17]     (a) G. Masuda, Y. Kubota, Y. Oshima, WIPO Patent WO2007049485A1 2007.
         (b) K. Iwasaki, T. Ito, Japanese Patent JP2013194147A 2013.

[18]  Y. Koga, S. Sakugawa, US Patent US2016009669A1 2016.

[19]  Tomy Green Farm For information on lemon myrtle see: http://www.geocities.jp/tomi19930410/index.html (accessed 4 August 2016).

[20]  H. Wen, N. Aoki, R. Ohsugi, Trop. Agr. Dev. 2012, 56, 14.
         | 1:CAS:528:DC%2BC38XovVWhsLk%3D&md5=aa879361c6b49a1979d59c5e6dcc086bCAS |

[21]  B. T. Schaneberg, I. A. Khan, J. Agric. Food Chem. 2002, 50, 1345.
         | CrossRef | 1:CAS:528:DC%2BD38XptVOmsg%3D%3D&md5=2e7368911c5b3abd13de0b45708cc126CAS | 11879000PubMed |

[22]  B. González, N. Calvar, E. Gómez, Á. Domínguez, J. Chem. Thermodyn. 2007, 39, 1578.
         | CrossRef |



Rent Article (via Deepdyve) Export Citation Cited By (2)