Comprehensive Characterization of Linalool-HP-β-Cyclodextrin Inclusion Complexes
Abstract
:1. Introduction
2. Results and Discussion
2.1. Complexation of Linalool with CDs
2.2. Obtaining Solid Inclusion Complexes Linalool-HP-β-CDs
Stability of Solid Complexes
2.3. Characterization of Linalool-HP-β-CDs Inclusion Complexes
2.3.1. 1H and 2D NMR Spectroscopy
2.3.2. Molecular Docking
2.3.3. Differential Scanning Calorimetry (DSC) and Thermogravimetric Analysis (TG)
2.3.4. Fourier Transform Infrared Spectroscopy (FTIR)
3. Materials and Methods
3.1. Materials
Reagents and Standards
3.2. Preparation of Inalool-Cyclodextrin Inclusion Complexes
3.2.1. Solubility Studies
3.2.2. Complexation Process by Using Microwave Irradiation (MWI)
3.2.3. Quantification of Linalool by GC-MS Analysis
3.2.4. Complexation Constant (KC) and Complexation Efficiency (CE) Calculation
3.3. Preparation of Linalool-HP-β-Cyclodextrin Inclusion Complexes by Spray Dryer
Field Emission Scanning Electron Microscope (FESEM) Images
3.4. Characterization of Linalool-HP-β-CDs Inclusion Complexes
3.4.1. 1H and 2D NMR Spectroscopy
3.4.2. Molecular Docking
3.4.3. Differential Scanning Calorimetry (DSC) and Thermogravimetric Analysis (TG)
3.4.4. Fourier Transform Infrared Spectroscopy (FTIR)
4. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Cyclodextrin | pH | S0 (mmol L−1) | KC (L mol−1) | CE | Molar Ratio linalool:CDs |
---|---|---|---|---|---|
α-CDs | 3.5 | 9.34 ± 0.20 | 17 ± 6 | 0.159 | 1:7 |
5.5 | 9.05 ± 0.16 | 25 ± 4 | 0.226 | 1:5 | |
6.5 | 8.16 ± 0.11 | 121 ± 9 | 0.987 | 1:2 | |
7.0 | 7.37 ± 0.03 | 148 ± 12 | 1.090 | 1:2 | |
8.5 | 9.33 ± 0.13 | 105 ± 8 | 0.979 | 1:2 | |
β-CDs | 3.5 | 9.34 ± 0.20 | 28 ± 4 | 0.261 | 1:5 |
5.5 | 9.05 ± 0.16 | 74 ± 5 | 0.670 | 1:2 | |
6.5 | 8.16 ± 0.11 | 91 ± 4 | 0.743 | 1:2 | |
7.0 | 7.37 ± 0.03 | 241 ± 26 | 1.776 | 1:2 | |
8.5 | 9.33 ± 0.13 | 16 ± 5 | 0.149 | 1:7 | |
HP-β-CDs | 3.5 | 9.34 ± 0.20 | 44 ± 6 | 0.411 | 1:3 |
5.5 | 9.05 ± 0.16 | 49 ± 7 | 0.443 | 1:3 | |
6.5 | 8.16 ± 0.11 | 225 ± 14 | 1.836 | 1:1 | |
7.0 | 7.37 ± 0.03 | 921 ± 21 | 6.788 | 1:1 | |
8.5 | 9.33 ± 0.13 | 559 ± 17 | 5.215 | 1:1 |
H-Atom | δ ppm−1 (Free) | δ ppm−1 (Complexed) | Δδ ppm−1 (Complexed-Free) | |
---|---|---|---|---|
Linalool | H-C (3) | 6.566 | 6.577 | −0.011 |
H-C (4) | 6.619 | 6.611 | 0.008 | |
H-C (6) | 6.917 | 6.929 | −0.012 | |
H-C (2′) | 2.740 | 2.758 | −0.018 | |
H-C (5′) | 2.126 | 2.124 | 0.002 | |
H-C (2′’) | 1.176 | 1.195 | −0.019 | |
HP-𝛽-CDs | H-C (1) | 5.074 | 5.121 | −0.047 |
H-C (2) | 3.723 | 3.730 | −0.007 | |
H-C (3) | 3.947 | 3.952 | −0.005 | |
H-C (4) | 3.418 | 3.417 | 0.001 | |
H-C (5) | 3.534 | 3.533 | 0.001 | |
H-C (6) | 3.821 | 3.815 | 0.006 | |
H-C (9) | 1.126 | 1.125 | 0.001 |
Sample Availability: Samples of the compounds Linalool-HP-β-Cyclodextrin Inclusion Complexes are available from the authors. | |
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Rodríguez-López, M.I.; Mercader-Ros, M.T.; Lucas-Abellán, C.; Pellicer, J.A.; Pérez-Garrido, A.; Pérez-Sánchez, H.; Yáñez-Gascón, M.J.; Gabaldón, J.A.; Núñez-Delicado, E. Comprehensive Characterization of Linalool-HP-β-Cyclodextrin Inclusion Complexes. Molecules 2020, 25, 5069. https://doi.org/10.3390/molecules25215069
Rodríguez-López MI, Mercader-Ros MT, Lucas-Abellán C, Pellicer JA, Pérez-Garrido A, Pérez-Sánchez H, Yáñez-Gascón MJ, Gabaldón JA, Núñez-Delicado E. Comprehensive Characterization of Linalool-HP-β-Cyclodextrin Inclusion Complexes. Molecules. 2020; 25(21):5069. https://doi.org/10.3390/molecules25215069
Chicago/Turabian StyleRodríguez-López, María Isabel, María Teresa Mercader-Ros, Carmen Lucas-Abellán, José Antonio Pellicer, Alfonso Pérez-Garrido, Horacio Pérez-Sánchez, María Josefa Yáñez-Gascón, José Antonio Gabaldón, and Estrella Núñez-Delicado. 2020. "Comprehensive Characterization of Linalool-HP-β-Cyclodextrin Inclusion Complexes" Molecules 25, no. 21: 5069. https://doi.org/10.3390/molecules25215069