Phosphate and Phosphonate-Based Ionic Liquids as New Additives in Foeniculum vulgare Essential Oil Extraction
Luisa Pistelli A , Rose Vanessa Bandeira Reidel A B , Piero Margari A and Cinzia Chiappe AA Dipartimento di Farmacia, Università di Pisa, Via Bonanno 33, 56126, Pisa, Italy.
B Corresponding author. Email: rvanessa.reidel@gmail.com
Australian Journal of Chemistry 71(3) 127-132 https://doi.org/10.1071/CH17406
Submitted: 19 July 2017 Accepted: 31 October 2017 Published: 22 November 2017
Abstract
The effect of the addition of four different halide-free ionic liquids (ILs) during the maceration step on Foeniculum vulgare essential oil (EO) extraction by hydrodistillation was investigated. The EO yields and their chemical composition were also evaluated, as well as the possibility of reusing the IL aqueous solutions. Although all the investigated ILs were able to increase EO yields, 1,3-dimethylimidazolium dimethylphosphate (IL1) showed the best performance. In particular, the 1 : 1 IL1–water mixture increased the EO yield by ~40 %, even after three reuses, maintaining practically the same volatile profile.
References
[1] M. Gross, E. Lewinsohn, Y. Tadmor, E. Bar, N. Dudai, Y. Cohen, J. Friedman, Biochem. Syst. Ecol. 2009, 37, 308.| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtFagtb7J&md5=450ad962fc2554a84cf893e03274e684CAS |
[2] A. Romojaro, M. A. Botella, C. Obòn, M. T. Pretel, Int. J. Food Sci. Nutr. 2013, 64, 944.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhslarsL7I&md5=189b100a2da1f66b34b8bd80b090ff6eCAS |
[3] S. Badgujar, V. V. Patel, A. H. Bandivdekar, BioMed. Res. Int. 2014, 2014, 842674.
[4] M. Licata, T. Tuttolomondo, C. Leto, G. Virga, G. Bonsangue, I. Cammalleri, M. C. Gennaro, S. La Bella, J. Ethnobiol. Ethnomed. 2016, 12, 12.
| Crossref | GoogleScholarGoogle Scholar |
[5] A. R. Bilia, M. Fumarola, G. Mazzi, F. F. Vincieri, J. Agric. Food Chem. 2000, 48, 4734.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXlsVShu7k%3D&md5=ddab3bc5dde9ec951d91c8b7d0d86cd3CAS |
[6] K. Gupta, K. K. Thakral, V. K. Gupta, S. K. Arora, J. Sci. Food Agric. 1995, 68, 73.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXmtVaqur0%3D&md5=ec15285b19e21ae4d4de54bd7d323260CAS |
[7] V. Sarafis, H. Rumpel, J. Pope, W. Kuhn, Protoplasma 1990, 159, 70.
| Crossref | GoogleScholarGoogle Scholar |
[8] P. V. Gersbach, N. Reddy, Ann. Bot. 2002, 90, 253.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XntVGrurc%3D&md5=7deff49d2c67e837ece0439d9b2d3e0fCAS |
[9] L. A. Sousa, J. C. R. Albuquerque, M. N. Leite, M. B. Stefanini, Rev. Bras. Farmacogn. 2005, 15, 155.
| Crossref | GoogleScholarGoogle Scholar |
[10] O. Cioanca, M. Hancianu, C. Mircea, A. Trifan, L. Hritcu, Ind. Crops Prod. 2016, 88, 51.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC28Xks1enurs%3D&md5=9d0cc971f85a7455890158b7f6463d33CAS |
[11] B. A. Sheikh, L. Pari, A. Rathinam, R. Chandramohan, Biochimie 2015, 112, 57.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXjtlCrurg%3D&md5=04abf994ce3bf4c0bfa9b4ce47d99bdfCAS |
[12] C. B. Oliveira, Y. S. Meurer, T. L. Medeiros, A. M. Pohlit, M. V. Silva, T. W. Mineo, V. F. Andrade-Neto, J. Parasitol. 2016, 102, 369.
| Crossref | GoogleScholarGoogle Scholar |
[13] A. A. Carvalho, L. N. Andrade, E. B. V. de Souza, D. P. de Sousa, BioMed Res. Int. 2015, 2015, 392674.
[14] S. Beddini, H. H. Bougherra, G. Flamini, F. Cosci, K. Belhamel, R. Ascrizzi, B. Conti, Bull. Insectology 2016, 69, 149.
[15] A. A. Shahat, A. Y. Ibrahim, S. F. Hendawy, E. A. Omer, F. M. Hammouda, F. H. Abdel-Rahman, M. A. Saleh, Molecules 2011, 16, 1366.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhvFans7g%3D&md5=07353b9043e2d0b556ee8703f813b240CAS |
[16] F. Senatore, F. Oliviero, E. Scandolera, O. Taglialatela-Scafati, G. Roscigno, M. Zaccardelli, E. De Falco, Fitoterapia 2013, 90, 214.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhsFGjsrvL&md5=b52dbf3f4da98b8687734bc648781513CAS |
[17] K. A. L. Wakabayashi, N. I. Melo, D. P. Aguiar, P. F. da Oliveira, M. Groppo, A. A. da Silva Filho, V. Rodrigues, W. R. Cunha, D. C. Tavares, L. G. Magalhaes, A. E. M. Crotti, Chem. Biodivers. 2015, 12, 1105.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXhtFCjt7bO&md5=b0224dba7d07753cd4cbe8f1af0887f8CAS |
[18] S. Zoubiri, A. Baaliouamer, N. Saba, N. Chamouni, Arab. J. Chem. 2014, 7, 480.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhtlahtr3K&md5=267bc5926316e85e8ce53e92cabe33bfCAS |
[19] International Trade Centre, Essentials Oils and Oleoresins 2015. Available at: http://www.intracen.org/itc/market-insider (accessed 10 January 2016).
[20] P. Rubiolo, B. Sgorbini, E. Liberto, C. Cordero, C. Bicchi, Flavour Fragrance J. 2010, 25, 282.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtlemsbfE&md5=bd7a315da85f8fa6714176db8bf2a908CAS |
[21] A. Capuzzo, M. E. Maffei, A. Occhipinti, Molecules 2013, 18, 7194.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtVOhsLvE&md5=c7228c8ece7663b923b01fad3faa37b6CAS |
[22] F. M. Hammouda, M. A. Saleh, N. S. Abdel-Azim, K. A. Shams, S. I. Ismail, A. Shalat, I. A. Saleh, Afr. J. Tradit. Complement. Altern. Med. 2014, 11, 277.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXmvFynur0%3D&md5=039b4a53e6880bbd923dab1e3979cd5aCAS |
[23] C. Chiappe, D. Pieraccini, J. Phys. Org. Chem. 2005, 18, 275.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXivVCksL4%3D&md5=f98b9bbb1d16d5945829ace53e2ed2a2CAS |
[24] F. Chemat, M. A. Vian, G. Cravotto, Int. J. Mol. Sci. 2012, 13, 8615.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtV2mtr7I&md5=8e5b254438d4d8f7037f32f6edd62081CAS |
[25] A. A. C. Toledo Hijo, G. J. Maximo, M. C. Costa, E. A. Batista, A. J. A. Meirelles, ACS Sustainable Chem. Eng. 2016, 4, 5347.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC28XhtlaktLjM&md5=5e479e4c55204fab3d8fe2cb63258abdCAS |
[26] M. Bhan, Int. J. Adv. Res. Dev. 2017, 2, 10.
[27] G. Flamini, B. Melai, L. Pistelli, C. Chiappe, RSC Adv. 2015, 5, 69894.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXhtlSntLzK&md5=70c836efdf4803687a4b65c50d54a68fCAS |
[28] L. Pistelli, S. Giovanelli, P. Margari, C. Chiappe, RSC Adv. 2016, 6, 52421.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC28XoslWkurw%3D&md5=4760092a3d69c99057bd2d3ac4339ffeCAS |
[29] S. P. M. Ventura, F. A. Silva, M. V. Quental, D. Mondal, M. G. Freire, J. A. P. Coutinho, Chem. Rev. 2017, 117, 6984.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2sXhvFeqsrs%3D&md5=0144c9d6b6456ce67d5b9184b142072dCAS |
[30] G. Cevasco, C. Chiappe, Green Chem. 2014, 16, 2375.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXmsFaht7w%3D&md5=f3d16da98e0c8e30f14128c225e533f6CAS |
[31] P. Manini, P. Margari, C. Pomelli, P. Franchi, G. Gentile, A. Napolitano, L. Valgimigli, C. Chiappe, V. Ball, M. D’Ischia, J. Phys. Chem. B 2016, 120, 11942.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC28XhvVSjur7I&md5=094e8f3d255312f908d42703746659aaCAS |
[32] K. Kuroda, H. Kunimura, Y. Fukaya, N. Nakamura, Thermochim. Acta 2014, 494, 94.
[33] C. Chiappe, G. C. Demontis, V. Di Bussolo, M. J. Douton Rodriguez, F. Rossella, C. S. Pomelli, S. Sartini, S. Caporali, Green Chem. 2017, 19, 1028.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC28XitVKrsr7I&md5=39ccb64e2c94e7d76a69df907fa53734CAS |
[34] E. Kuhlmann, S. Himmler, H. Giebelhaus, Green Chem. 2007, 9, 233.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXitlKltLY%3D&md5=a1ea358c6e43f7b9018b43877a9ce9adCAS |
[35] National Institute of Standards and Technology, PC Version 1.7 of the NIST/EPA/NIH Mass Spectral Library 2014 (Perkin Elmer: Norwalk, CT).
[36] R. P. Adams, Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry 1995 (Allured Publish Corp.: Carol Stream, IL).
[37] E. Schmidt, in Handbook of Essential Oils: Science, Technology, and Applications (2nd edn) (Eds K. H. C. Baser, G. Buchbauer) 2016, Ch. 5, pp. 127–162 (CRC Press: Boca Raton, FL).
[38] M. Koşar, T. Özek, M. Kürkçüoglu, K. H. C. Başer, J. Essent. Oil Res. 2007, 19, 426.
| Crossref | GoogleScholarGoogle Scholar |
[39] J. González-Rivera, C. Duce, D. Falconieri, C. Ferrari, L. Ghezzi, A. Piras, M. R. Tine, Innovative Food Sci. Emerging Technol. 2016, 33, 308.
[40] A. Piras, D. Falconieri, S. Porcedda, B. Marongiu, M. J. Gonçalves, C. Cavaleiro, L. Salgueiro, Nat. Prod. Res. 2014, 28, 1819.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhtlOjsLfJ&md5=22d2ee2cb1c5051d6a9c0d002a890204CAS |