Liquid–liquid extraction of hydroxytyrosol, tyrosol, and oleuropein using ionic liquids

References

• Rodis, P.S.; Karathanos, V.T.; Mantzavinou, A. (2002) Partitioning of olive oil antioxidants between oil and water phases. Journal of Agricultural and Food Chemistry, 50 (3): 596. doi:10.1021/jf010864j
   PubMed Web of Science ®Google Scholar
• Covas, M.I.; De La Torre, K.; Farré-Albaladejo, M.; Kaikkonen, J.; Fitó, M.; López-Sabater, C.; Pujadas-Bastardes, M.A.; Joglar, J.; Weinbrenner, T.;, et al. (2006) Postprandial LDL phenolic content and LDL oxidation are modulated by olive oil phenolic compounds in humans. Free Radical Biology & Medicine, 40 (4): 608. doi:10.1016/j.freeradbiomed.2005.09.027
   PubMed Web of Science ®Google Scholar
• Esti, M.; Cinquanta, L.; Notte, E.L. (1998) Phenolic compounds in different olive varieties phenolic compounds in different olive varieties. Journal of Agricultural and Food Chemistry, 46 (1): 32.
   PubMed Web of Science ®Google Scholar
• Chandramohan, R.; Pari, L. (2016) Anti-inflammatory effects of tyrosol in streptozotocin-induced diabetic Wistar rats. Journal of Functional Foods, 27: 17. doi:10.1016/j.jff.2016.08.043
   Web of Science ®Google Scholar
• González-Santiago, M.; Martín-Bautista, E.; Carrero, J.J.; Fonollá, J.; Baró, L.; Bartolomé, M.V.; Gil-Loyzaga, P.; López-Huertas, E. (2006) One-month administration of hydroxytyrosol, a phenolic antioxidant present in olive oil, to hyperlipemic rabbits improves blood lipid profile, antioxidant status and reduces atherosclerosis development. Atherosclerosis, 188 (1): 35. doi:10.1016/j.atherosclerosis.2005.10.022
   PubMed Web of Science ®Google Scholar
• Vilaplana-Pérez, C.; Auñón, D.; García-Flores, L.; Gil-Izquierdo, A. (2014) Hydroxytyrosol and potential uses in cardiovascular diseases, cancer, and AIDS. Frontiers in Nutrition, 27 (1): 1.
   Google Scholar
• Bazoti, F.N.; Bergquist, J.; Markides, K.E.; Tsarbopoulos, A. (2006) Noncovalent interaction between amyloid-β-peptide (1-40) and oleuropein studied by electrospray ionization mass spectrometry. Journal of the American Society for Mass Spectrometry, 17 (4): 568. doi:10.1016/j.jasms.2005.12.013
   PubMed Web of Science ®Google Scholar
• Grasso, S.; Siracusa, L.; Spatafora, C.; Renis, M.; Tringali, C. (2007) Hydroxytyrosol lipophilic analogues: enzymatic synthesis, radical scavenging activity and DNA oxidative damage protection. Bioorganic chemistry, 35 (2): 137. doi:10.1016/j.bioorg.2006.09.003
   PubMed Web of Science ®Google Scholar
• Young, I.S.; Woodside, J.V. (2001) Antioxidants in health and disease Antioxidants in health and disease. Journal of Clinical Pathology, 176. doi:10.1136/jcp.54.3.176
   PubMed Web of Science ®Google Scholar
• Bernini, R.; Mincione, E.; Crisante, F.; Barontini, M.; Fabrizi, G. (2009) A novel use of the recyclable polymer-supported IBX: an efficient chemoselective and regioselective oxidation of phenolic compounds. The case of hydroxytyrosol derivatives. Tetrahedron Letters, 50 (12): 1307. doi:10.1016/j.tetlet.2009.01.037
   Web of Science ®Google Scholar
• De Lucia, M.; Panzella, L.; Pezzella, A.; Napolitano, A.; D’Ischia, M. (2006) Oxidative chemistry of the natural antioxidant hydroxytyrosol: hydrogen peroxide-dependent hydroxylation and hydroxyquinone/o-quinone coupling pathways. Tetrahedron, 62 (6): 1273. doi:10.1016/j.tet.2005.10.055
   Web of Science ®Google Scholar
• Gambacorta, A.; Tofani, D.; Bernini, R.; Migliorini, A. (2007) High-yielding preparation of a stable precursor of hydroxytyrosol by total synthesis and from the natural glycoside oleuropein. Journal of Agricultural and Food Chemistry, 55 (9): 3386. doi:10.1021/jf063353b
   PubMed Web of Science ®Google Scholar
• Briante, R.; Patumi, M.; Febbraio, F.; Nucci, R. (2004) Production of highly purified hydroxytyrosol from Olea europaea leaf extract biotransformed by hyperthermophilic β-glycosidase. Journal of Biotechnology, 111 (1): 67. doi:10.1016/j.jbiotec.2004.03.011
   PubMed Web of Science ®Google Scholar
• Azaizeh, H.; Halahlih, F.; Najami, N.; Brunner, D.; Faulstich, M.; Tafesh, A. (2012) Antioxidant activity of phenolic fractions in olive mill wastewater. Food Chemistry, 134 (4): 2226. doi:10.1016/j.foodchem.2012.04.035
   PubMed Web of Science ®Google Scholar
• Kalogerakis, N.; Politi, M.; Foteinis, S.; Chatzisymeon, E.; Mantzavinos, D. (2013) Recovery of antioxidants from olive mill wastewaters: A viable solution that promotes their overall sustainable management. Journal of Environmental Management, 128: 749. doi:10.1016/j.jenvman.2013.06.027
   PubMed Web of Science ®Google Scholar
• Geankoplis, C.J.;. (2003) Transport Processes and Separation Process Principles (Includes Unit Operations), 4th; Prentice Hall; Edición: 1056. Upper Saddler River, New Jersey, USA.
   Google Scholar
• Ray, S.K.; Sawant, S.B.; Joshi, J.B.; Pangarkar, V.G. (1997) Perstraction of phenolic compounds from aqueous solution using a nonporous membrane. Separation Science and Technology, 32 (16): 2669. doi:10.1080/01496399708006963
   Web of Science ®Google Scholar
• Jiao, J.; Gai, Q.Y.; Fu, Y.J.; Zu, Y.G.; Luo, M.; Zhao, C.J.; Li, C.Y. (2013) Microwave-assisted ionic liquids treatment followed by hydro-distillation for the efficient isolation of essential oil from Fructus forsythiae seed. Separation and Purification Technology, 107: 228. doi:10.1016/j.seppur.2013.01.009
   Web of Science ®Google Scholar
• Pereiro, A.B.; Araújo, J.M.M.; Esperança, J.M.S.S.; Marrucho, I.M.; Rebelo, L.P.N. (2012) Ionic liquids in separations of azeotropic systems - A review. Journal of Chemical Thermodynamics, 46: 2. doi:10.1016/j.jct.2011.05.026
   Web of Science ®Google Scholar
• Visser, A.E.; Jensen, M.P.; Laszak, I.; Nash, K.L.; Choppin, G.R.; Rogers, R.D. (2003) Uranyl coordination environment in hydrophobic ionic liquids: an in situ investigation. Inorganic Chemistry, 42 (7): 2197. doi:10.1021/ic020405f
   PubMed Web of Science ®Google Scholar
• Belhocine, T.; Forsyth, S.A.; Gunaratne, H.Q.N.; Nieuwenhuyzen, M.; Puga, A.V.; Seddon, K.R.; Srinivasan, G.; Whiston, K. (2011) New ionic liquids from azepane and 3-methylpiperidine exhibiting wide electrochemical windows. Green Chemistry, 13 (1): 59. doi:10.1039/C0GC00534G
   Web of Science ®Google Scholar
• Tian, Y.H.; Goff, G.S.; Runde, W.H.; Batista, E.R. (2012) Exploring electrochemical windows of room-temperature ionic liquids: A computational study. Journal of Physical Chemistry B, 116 (39): 11943. doi:10.1021/jp303915c
   PubMed Web of Science ®Google Scholar
• Stojanovic, A.; Morgenbesser, C.; Kogelnig, D.; Krachler, R.; Keppler, B.K. (2011) Quaternary ammonium and phosphonium ionic liquids in chemical and environmental engineering. In: Alexander Kokorin (ed), Ionic Liquids: Theory, Properties, New Approaches. pp. 657–681. IntechOpen Limited: London, UK.
   Google Scholar
• Merlet, G.; Uribe, F.; Aravena, C.; Rodríguez, M.; Cabezas, R.; Quijada-Maldonado, E.; Romero, J. (2017) Separation of fermentation products from ABE mixtures by perstraction using hydrophobic ionic liquids as extractants. Journal of Membrane Science, 537 (May): 337. doi:10.1016/j.memsci.2017.05.045
   Google Scholar
• Edge, R.M.; Grant, C.D. (1971) The terminal velocity and frequency of oscillation of drops in pure systems. Chemical Engineering Science, 26 (7): 1001. doi:10.1016/0009-2509(71)80013-1
   Web of Science ®Google Scholar
• Wegener, M.; Paul, N.; Kraume, M. (2014) Fluid dynamics and mass transfer at single droplets in liquid/liquid systems. International Journal of Heat and Mass Transfer, 71: 475. doi:10.1016/j.ijheatmasstransfer.2013.12.024
   Web of Science ®Google Scholar
• Zambra, C.E.; Muñoz, J.F.; Moraga, N.O. (2015) A 3D coupled model of turbulent forced convection and diffusion for heat and mass transfer in a bioleaching process. International Journal of Heat and Mass Transfer, 85: 390. doi:10.1016/j.ijheatmasstransfer.2015.01.135
   Web of Science ®Google Scholar
• Romero, C.; Brenes, M. (2012) Analysis of total contents of hydroxytyrosol and tyrosol in olive oils. Journal of Agricultural and Food Chemistry, 60 (36): 9017. doi:10.1021/jf3026666
   PubMed Web of Science ®Google Scholar
• Al-Rimawi, F.;. (2014) Development and validation of a simple reversed-phase HPLC-UV method for determination of oleuropein in olive leaves. Journal of Food and Drug Analysis, 22 (3): 285. doi:10.1016/j.jfda.2013.10.002
   PubMed Web of Science ®Google Scholar
• Kumar, A.; Hartland, S. (1999) Correlations for prediction of mass transfer coefficients in single drop systems and liquid-liquid extraction columns. Chemical Engineering Research and Design, 77 (5): 372. doi:10.1205/026387699526359
   Web of Science ®Google Scholar
• Wilke, C.R.; Chang, P. (1955) Correlation of Diffusion Coefficients in Dilute:264. AIChE Journal, 1 (2):264. doi.wiley.com/10.1002/aic.690010222
   Google Scholar
• Perry, R.H.; Green, D.W. (2008) Perry’s Chemical Engineers’ Handbook, McGraw-Hill: New York. 750.
   Google Scholar
• Cammarata, L.; Kazarian, S.G.; Salter, P.A.; Welton, T. (2001) Molecular states of water in room temperature ionic liquidsElectronic supplementary information available. Physical Chemistry Chemical Physics, 3 (23): 5192. doi:10.1039/b106900d See http://www.rsc.org/suppdata/cp/b1/b106900d/.
   Web of Science ®Google Scholar