Solubility, Solution Thermodynamics, and Preferential Solvation of Amygdalin in Ethanol + Water Solvent Mixtures
Se informó la solubilidad en equilibrio de la amigdalina en mezclas de [etanol (1) + agua (2)] a 293,15 K a 328,15 K. Las propiedades termodinámicas (entalpía estándar Δ soln H °, entropía estándar Δ soln S ° y energía de Gibbs estándar de la solución Δ solnG °) se calcularon utilizando los datos de...
- Autores:
-
Aydi, Abdelkarim
Ayadi, Cherifa
Ghachem, Kaouther
Al-Khazaal, Abdulaal Z.
Delgado, Daniel Ricardo
Alnaief, Mohammad
Kolsi, Lioua
- Tipo de recurso:
- Article of journal
- Fecha de publicación:
- 2020
- Institución:
- Universidad Cooperativa de Colombia
- Repositorio:
- Repositorio UCC
- Idioma:
- OAI Identifier:
- oai:repository.ucc.edu.co:20.500.12494/28273
- Palabra clave:
- Amigdalina
Integral de Kirkwood-Buff inversa
Termodinámica
Van't Hoff
Ecuación de Gibbs
Solubilidad
Jouyban – Acree
Buchowski – Ksiazczak
Amygdalin
Gibbs equation
Van’t Hoff
Thermodynamics
Solubility
Jouyban–Acree
Buchowski–Ksiazczak
Inverse Kirkwood–Buff integral
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- openAccess
- License
- Atribución
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dc.title.spa.fl_str_mv |
Solubility, Solution Thermodynamics, and Preferential Solvation of Amygdalin in Ethanol + Water Solvent Mixtures |
title |
Solubility, Solution Thermodynamics, and Preferential Solvation of Amygdalin in Ethanol + Water Solvent Mixtures |
spellingShingle |
Solubility, Solution Thermodynamics, and Preferential Solvation of Amygdalin in Ethanol + Water Solvent Mixtures Amigdalina Integral de Kirkwood-Buff inversa Termodinámica Van't Hoff Ecuación de Gibbs Solubilidad Jouyban – Acree Buchowski – Ksiazczak Amygdalin Gibbs equation Van’t Hoff Thermodynamics Solubility Jouyban–Acree Buchowski–Ksiazczak Inverse Kirkwood–Buff integral |
title_short |
Solubility, Solution Thermodynamics, and Preferential Solvation of Amygdalin in Ethanol + Water Solvent Mixtures |
title_full |
Solubility, Solution Thermodynamics, and Preferential Solvation of Amygdalin in Ethanol + Water Solvent Mixtures |
title_fullStr |
Solubility, Solution Thermodynamics, and Preferential Solvation of Amygdalin in Ethanol + Water Solvent Mixtures |
title_full_unstemmed |
Solubility, Solution Thermodynamics, and Preferential Solvation of Amygdalin in Ethanol + Water Solvent Mixtures |
title_sort |
Solubility, Solution Thermodynamics, and Preferential Solvation of Amygdalin in Ethanol + Water Solvent Mixtures |
dc.creator.fl_str_mv |
Aydi, Abdelkarim Ayadi, Cherifa Ghachem, Kaouther Al-Khazaal, Abdulaal Z. Delgado, Daniel Ricardo Alnaief, Mohammad Kolsi, Lioua |
dc.contributor.author.none.fl_str_mv |
Aydi, Abdelkarim Ayadi, Cherifa Ghachem, Kaouther Al-Khazaal, Abdulaal Z. Delgado, Daniel Ricardo Alnaief, Mohammad Kolsi, Lioua |
dc.subject.spa.fl_str_mv |
Amigdalina Integral de Kirkwood-Buff inversa Termodinámica Van't Hoff Ecuación de Gibbs Solubilidad Jouyban – Acree Buchowski – Ksiazczak |
topic |
Amigdalina Integral de Kirkwood-Buff inversa Termodinámica Van't Hoff Ecuación de Gibbs Solubilidad Jouyban – Acree Buchowski – Ksiazczak Amygdalin Gibbs equation Van’t Hoff Thermodynamics Solubility Jouyban–Acree Buchowski–Ksiazczak Inverse Kirkwood–Buff integral |
dc.subject.other.spa.fl_str_mv |
Amygdalin Gibbs equation Van’t Hoff Thermodynamics Solubility Jouyban–Acree Buchowski–Ksiazczak Inverse Kirkwood–Buff integral |
description |
Se informó la solubilidad en equilibrio de la amigdalina en mezclas de [etanol (1) + agua (2)] a 293,15 K a 328,15 K. Las propiedades termodinámicas (entalpía estándar Δ soln H °, entropía estándar Δ soln S ° y energía de Gibbs estándar de la solución Δ solnG °) se calcularon utilizando los datos de solubilidad generados mediante las ecuaciones de van't Hoff y Gibbs. El proceso de disolución de la amigdalina es endotérmico y el mecanismo impulsor de todas las mezclas es la entropía. La solubilidad máxima se logró en 0,4 moles de fracción de etanol a 328,15 K y la mínima en etanol puro a 293,15 K. Se utilizaron modelos de Van't Hoff, Jouyban-Acree-van't Hoff y Buchowski-Ksiazczak para simular la solubilidad obtenida datos. Las solubilidades calculadas se desvían razonablemente de los datos experimentales. Los parámetros de solvatación preferenciales de amigdalina en mezclas de disolventes se analizaron utilizando el método de integrales inversas de Kirkwood-Buff (IKBI). La amigdalina se solvata preferentemente con agua en mezclas ricas en etanol, mientras que en mezclas ricas en agua, |
publishDate |
2020 |
dc.date.accessioned.none.fl_str_mv |
2020-11-25T19:52:38Z |
dc.date.available.none.fl_str_mv |
2020-11-01 2020-11-25T19:52:38Z |
dc.date.issued.none.fl_str_mv |
2020-11-14 |
dc.type.none.fl_str_mv |
Artículo |
dc.type.coar.fl_str_mv |
http://purl.org/coar/resource_type/c_2df8fbb1 |
dc.type.coar.none.fl_str_mv |
http://purl.org/coar/resource_type/c_6501 |
dc.type.coarversion.none.fl_str_mv |
http://purl.org/coar/version/c_970fb48d4fbd8a85 |
dc.type.driver.none.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.version.none.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
http://purl.org/coar/resource_type/c_6501 |
status_str |
publishedVersion |
dc.identifier.issn.spa.fl_str_mv |
14248247 |
dc.identifier.uri.spa.fl_str_mv |
https://doi.org/10.3390/ph13110395 |
dc.identifier.uri.none.fl_str_mv |
https://hdl.handle.net/20.500.12494/28273 |
dc.identifier.bibliographicCitation.spa.fl_str_mv |
Aydi, A.; Ayadi, C.; Ghachem, K.; Al-Khazaal, A.Z.; Delgado, D.R.; Alnaief, M.; Kolsi, L. Solubility, Solution Thermodynamics, and Preferential Solvation of Amygdalin in Ethanol + Water Solvent Mixtures. Pharmaceuticals 2020, 13, 395. |
identifier_str_mv |
14248247 Aydi, A.; Ayadi, C.; Ghachem, K.; Al-Khazaal, A.Z.; Delgado, D.R.; Alnaief, M.; Kolsi, L. Solubility, Solution Thermodynamics, and Preferential Solvation of Amygdalin in Ethanol + Water Solvent Mixtures. Pharmaceuticals 2020, 13, 395. |
url |
https://doi.org/10.3390/ph13110395 https://hdl.handle.net/20.500.12494/28273 |
dc.relation.isversionof.spa.fl_str_mv |
https://www.mdpi.com/1424-8247/13/11/395 |
dc.relation.ispartofjournal.spa.fl_str_mv |
Pharmaceuticals |
dc.relation.references.spa.fl_str_mv |
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The enzymic hydrolysis of Amygdalin. Biochem. J. 1967, 103, 528–534. Bolarinwa, I.F.; Orfila, C.; Morgan, M.R. Amygdalin content of seeds, kernels and food products commercially-available in the UK. Food Chem. 2014, 52, 133–139. Krieble, V.K. The amygdalins and their inter-reactions with emulsin. J. Am. Chem. Soc. 1912, 34, 716–735. Boháčová, I.; Procházková, S.; Halko, R. Separation and determination of Amygdalin and unnatural neoAmygdalin in natural food supplements by HPLC-DAD. Food Addit. Contam. Part A 2019, 36, 1445–1452. Thapa, R.K.; Choi, H.G.; Kim, J.O.; Yong, C.S. Analysis and optimization of drug solubility to improve pharmacokinetics. J. Pharm. Investig. 2017, 47, 95–110. Pacheco, D.P.; Martínez, F. Thermodynamic analysis of the solubility of naproxen in ethanol + water cosolvent mixtures. Phys. Chem. Liq. 2007, 45, 581–595. Di, L.; Fish, P.V.; Mano, T. Bridging solubility between drug discovery and development. Drug Discov. Today 2012, 17, 486–495. 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In Fluctuation Theory of Solutions: Applications in Chemistry, Chemical Engineering, and Biophysics; CRC Press: Boca Raton, FL, USA, 2013; pp. 65–92 Marcus, Y. Preferential solvation of drugs in binary solvent mixtures. Pharm. Anal. Acta 2017, 8, 537. Yalkowsky, S.H. Solubility and Solubilization in Aqueous Media; American Chemical Society: New York, USA, 1999. Williams, R.O., III; Watts, A.B.; Miller, D.A. Formulating Poorly Water Soluble Drugs; American Association of Pharmaceutical Scientists: Austin, TX, USA, 2016. Delgado, D.R.; Rodríguez, G.A.; Martínez, F. Thermodynamic study of the solubility of sulfapyridine in some ethanol + water mixtures. J. Mol. Liq. 2013, 177, 156–161. Muñoz, M.d.; Delgado, D.R.; Peña, M.Á.; Jouyban, A.; Martínez, F. Solubility and preferential solvation of sulfadiazine, sulfamerazine and sulfamethazine in propylene glycol + water mixtures at 298.15 K. J. Mol. Liq. 2015, 204, 132–136. Barton, A. CRC Handbook of Solubility Parameters and Other Cohesion Parameters, 2nd ed.; CRC Press: New York, NY, USA, 1991. Delgado, D.R.; Mogollon-Waltero, E.M.; Ortiz, C.P.; Peña, M.; Almanza, O.A.; Martínez, F.; Jouyban, A. Enthalpy-entropy compensation analysis of the triclocarban dissolution process in some {1,4-dioxane (1) + water (2)} mixtures. J. Mol. Liq. 2018, 271, 522–529. Hildebtand, J.H.; Prausnitz, J.M.; Scott, R.L. Regular and Related Solutions: The Solubility of Gases, Liquids, and Solids; Van Nostrand Reinhold Company: New Tork, NY, USA, 1970. Grant, D.J.W.; Mehdizadeh, M.; Chow, A.H.L.; Fairbrother, J.E. Non-linear van’t Hoff solubility-temperature plots and their pharmaceutical interpretation. Int. J. Pharm. 1984, 18, 25–38. Jouyban, A.; Acree, W.E. Mathematical derivation of the Jouyban-Acree model to represent solute solubility data in mixed solvents at various temperatures. J. Mol. Liq. 2018, 256, 541–547. Ruidiaz, M.; Delgado, D.R.; Martínez, F. Correlating the solubility of indomethacin in 1,4-dioxane + water mixtures by means of the Jouyban-Acree model. Rev. Colomb. Cienc. Químico Farm. 2010, 39, 211–226. Acree, W.; Jouyban, A.; Acree, W.E. In silico prediction of drug solubility in water-ethanol mixtures using Jouyban-Acree model. J. Pharm Pharm. Sci. 2006, 9, 262–269. Nieto, A.M.R.; Cerquera, N.E.; Delgado, D.R. Measurement and correlation of solubility of ethylparaben in pure and binary solvents and thermodynamic properties of solution. Rev. Colomb. Cienc. Químico Farm. 2019, 48, 332–347. Ksia̧ẑczak, A.; Kosinski, J.J. Vapour pressure of binary, three-phase (S-L-V) systems and solubility. Fluid Phase Equilibria 1988, 44, 211–236. Ksiazczak, A.; Moorthi, K.; Nagata, I. Solid-solid transition and solubility of even n-alkanes. Fluid Phase Equilibria 1994, 95, 15–29. Krajangsod, S.; Chotikamas, S.; Tawai, A.; Sriariyanun, M. Measurement and thermodynamic modelling of erythritol solubility in aqueous solvents. Orient. J. 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Liq. 2020, 310, 113148. Perlovich, G.L.; Strakhova, N.N.; Kazachenko, V.P.; Volkova, T.V.; Tkachev, V.V.; Schaper, K.J.; Raevsky, O.A. Sulfonamides as a subject to study molecular interactions in crystals and solutions: Sublimation, solubility, solvation, distribution and crystal structure. Int. J. Pharm. 2008, 349, 300–313. Bustamante, P.; Escalera, B. Enthalpy and Entropy Contributions to the Solubility of Sulphamethoxypyridazine in Solvent Mixtures Showing Two Solubility Maxima. J. Pharm. Pharmacol. 1995, 47, 550–555. Bustamante, E.P.; Ochoa, R.; Reillo, A.; Escalera, J.-B. Chameleonic Effect of Sulfanilamide and Sulfamethazine in Solvent Mixtures. Solubility Curves with Two Maxima. Chem. Pharm. Bull. 1994, 42, 1129–1133. Ben-Naim, A. Theory of preferential solvation of nonelectrolytes. Cell Biophys. 1988, 12, 255–269. Ben-Naim, A. Theoretical aspects of self-assembly of proteins: A Kirkwood-Buff-theory approach. J. Chem. Phys. 2013, 138, 06B609_1. Ben-Naim, A.; Navarro, A.M.; Leal, J.M. A Kirkwood-Buff analysis of local properties of solutions. Phys. Chem. Chem. Phys. 2008, 10, 2451–2460. Marcus, Y. Solvent Mixtures: Properties and Selective Solvation; CRC Press: New York, NY, USA, 2002. Marcus, Y. On the preferential solvation of drugs and PAHs in binary solvent mixtures. J. Mol. Liq. 2008, 140, 61–67. Delgado, D.R.; Vargas, E.F.; Martínez, F. Preferential solvation of xylitol in ethanol + water co-solvent mixtures according to the IKBI and QLQC methods. Rev. Colomb. Quim. 2013, 42, 125–133. Marcus, Y. Preferential solvation in mixed solvents. 16. Mixtures of N,N-dimethylformamide or propylene carbonate with organic solvents. J. Chem. Thermodyn. 2020, 140, 105903. Delgado, D.R.; Peña, M.A.; Martínez, F. Preferential solvation of acetaminophen in ethanol + water solvent mixtures according to the inverse Kirkwood-Buff integrals method. Rev. Colomb Cienc. Químico Farm. 2013, 42, 298–314. Marcus, Y. Preferential solvation in mixed solvents. 15. Mixtures of acetonitrile with organic solvents. J. Chem. Thermodyn. 2019, 135, 55–59. Castro, J.J.S.; Ortiz, C.P.; Rodríguez-Rubiano, J.D.; Rodríguez-Rodríguez, G.A.; Delgado, D.R. Preferential solvation of tricin in {ethanol (1) + water (2)} mixtures at several temperatures. Rev. Colomb. Cienc. Químico Farm. 2018, 47, 135–148. Marcus, Y. Preferential solvation. Part 3.—Binary solvent mixtures. J. Chem. Soc. Faraday Trans. 1 Phys. Chem. Condens. Phases. 1989, 85, 381–388. Marcus, Y. The Properties of Solvents; John Wiley & Sons Ltd.: New York, NY, USA, 1999. Jiménez, J.; Manrique, J.; Martínez, F. Effect of temperature on some volumetric properties for ethanol + water mixtures. Rev. Colomb. Cienc. Químico Farm. 2004, 33, 145–155. Aldana, G.A.d.A.; Rubio, D.I.C.; Rodríguez, G.A.R.; Lozano, A.C.; Mehrdad, A.; Delgado, D.R.; Carmona, N.A.P. Solution thermodynamics and preferential solvation of 3-chloro-N-phenyl-phthalimide in acetone + methanol mixtures. Rev. Colomb. Cienc. Químico Farm. 2016, 45, 256. Taft, R.W.; Kamlet, M.J. The Solvatochromic Comparison Method. 2. The α-Scale of Solvent Hydrogen-Bond Donor (HBD) Acidities. J. Am. Chem. Soc. 1976, 98, 2886–2894. Noubigh, A. Stearic acid solubility in mixed solvents of (water + ethanol) and (ethanol + ethyl acetate): Experimental data and comparison among different thermodynamic models. J. Mol. Liq. 2019, 296, 112101. Noubigh, A.; Aydi, A.; Abderrabba, M. Experimental measurement and correlation of solubility data and thermodynamic properties of protocatechuic acid in four organic solvents. J. Chem. Eng. Data 2017, 60, 514–518. Noubigh, A.; Akremi, A. Solution thermodynamics of trans-Cinnamic acid in (methanol + water) and (ethanol + water) mixtures at different temperatures. J. Mol. Liq. 2019, 274, 752–758. |
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Aydi, AbdelkarimAyadi, CherifaGhachem, KaoutherAl-Khazaal, Abdulaal Z.Delgado, Daniel RicardoAlnaief, MohammadKolsi, Lioua132020-11-25T19:52:38Z2020-11-012020-11-25T19:52:38Z2020-11-1414248247https://doi.org/10.3390/ph13110395https://hdl.handle.net/20.500.12494/28273Aydi, A.; Ayadi, C.; Ghachem, K.; Al-Khazaal, A.Z.; Delgado, D.R.; Alnaief, M.; Kolsi, L. Solubility, Solution Thermodynamics, and Preferential Solvation of Amygdalin in Ethanol + Water Solvent Mixtures. Pharmaceuticals 2020, 13, 395.Se informó la solubilidad en equilibrio de la amigdalina en mezclas de [etanol (1) + agua (2)] a 293,15 K a 328,15 K. Las propiedades termodinámicas (entalpía estándar Δ soln H °, entropía estándar Δ soln S ° y energía de Gibbs estándar de la solución Δ solnG °) se calcularon utilizando los datos de solubilidad generados mediante las ecuaciones de van't Hoff y Gibbs. El proceso de disolución de la amigdalina es endotérmico y el mecanismo impulsor de todas las mezclas es la entropía. La solubilidad máxima se logró en 0,4 moles de fracción de etanol a 328,15 K y la mínima en etanol puro a 293,15 K. Se utilizaron modelos de Van't Hoff, Jouyban-Acree-van't Hoff y Buchowski-Ksiazczak para simular la solubilidad obtenida datos. Las solubilidades calculadas se desvían razonablemente de los datos experimentales. Los parámetros de solvatación preferenciales de amigdalina en mezclas de disolventes se analizaron utilizando el método de integrales inversas de Kirkwood-Buff (IKBI). La amigdalina se solvata preferentemente con agua en mezclas ricas en etanol, mientras que en mezclas ricas en agua,The equilibrium solubility of amygdalin in [ethanol (1) + water (2)] mixtures at 293.15 K to 328.15 K was reported. The thermodynamic properties (standard enthalpy ΔsolnH°, standard entropy ΔsolnS°, and standard Gibbs energy of solution ΔsolnG°) were computed using the generated solubility data via van’t Hoff and Gibbs equations. The dissolution process of amygdalin is endothermic and the driving mechanism in all mixtures is entropy. Maximal solubility was achieved in 0.4 mole fraction of ethanol at 328.15 K and the minimal one in neat ethanol at 293.15 K. Van’t Hoff, Jouyban–Acree–van’t Hoff, and Buchowski–Ksiazczak models were used to simulate the obtained solubility data. The calculated solubilities deviate reasonably from experimental data. Preferential solvation parameters of amygdalin in mixture solvents were analyzed using the inverse Kirkwood–Buff integrals (IKBI) method. Amygdalin is preferentially solvated by water in ethanol-rich mixtures, whereas in water-rich mixtures, there is no clear evidence that determines which of water or ethanol solvents would be most likely to solvate the molecule.1. Introduction. -- 2. Results and Discussion. -- 3. Experimental procedures. --4. 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Liq. 2019, 274, 752–758.AmigdalinaIntegral de Kirkwood-Buff inversaTermodinámicaVan't HoffEcuación de GibbsSolubilidadJouyban – AcreeBuchowski – KsiazczakAmygdalinGibbs equationVan’t HoffThermodynamicsSolubilityJouyban–AcreeBuchowski–KsiazczakInverse Kirkwood–Buff integralSolubility, Solution Thermodynamics, and Preferential Solvation of Amygdalin in Ethanol + Water Solvent MixturesArtículohttp://purl.org/coar/resource_type/c_6501http://purl.org/coar/resource_type/c_2df8fbb1http://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionAtribucióninfo:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2PublicationORIGINAL2020_Solubility_thermodynamics.Preferential.pdf2020_Solubility_thermodynamics.Preferential.pdfArtículo científicoapplication/pdf2479436https://repository.ucc.edu.co/bitstreams/989499b7-22ab-48b0-b297-f134df0d18f7/downloadef979fcc34aed0f15b865cce3634a93eMD51LICENSElicense.txtlicense.txttext/plain; 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