Journal of Inclusion Phenomena and Macrocyclic Chemistry

Bioactive microparticles (10):

Thermal and oxidative stability of nicotine and its complex with βcyclodextrin

(SupplementaryMaterial)

Daniel Ioan Hădărugă, Ph.D.a,*, Nicoleta Gabriela Hădărugă, Ph.D.b,

Gallia Butnaru, Ph.D.c, Călin Tatu, Ph.D.d, Alexandra Gruia, Ph.D.St.d

a “Politehnica” University of Timişoara, Faculty of Industrial Chemistry and Environmental Engineering, Organic Chemistry and Technology Department, 300006-Timişoara, P-ţa Victoriei 2, Romania

b Banat’s University of Agricultural Sciences and Veterinary Medicine, Faculty of Food Processing Technology, Food Quality Department, 300645-Timişoara, C. Aradului 119, Romania

c Banat’s University of Agricultural Sciences and Veterinary Medicine, Faculty of Horticulture and Forestry, Genetic Engineering in Agriculture Department, 300645-Timişoara, C. Aradului 119, Romania

d County Hospital Timişoara, Regional Centre of Immunology and Transplant, 300736-Timişoara, Bv. Iosif Bulbuca 10, Romania

GC-MS analysis of the raw and degraded nicotine samples and of the extracts recovered from non-degraded and degraded bCD complexes

Figure S1.MS spectraof the GC-MS analysis (up) and from the NIST database (down) for myosmine

Figure S2.MS spectraof the GC-MS analysis (up) and from the NIST database (down) for nicotyrine

Figure S3.MS spectraof the GC-MS analysis (up) and from the NIST database (down) for isonicoteline

Figure S4.Chromatogram from the GC-MS analysis of thedegraded nicotine sample (at 30ºC, in the presence of air for 2 h; code N-O-t1)

Figure S5.Chromatogram from the GC-MS analysis of thedegraded nicotine sample (at 90ºC, in the presence of air for 2 h; code N-O-t3)

Figure S6.Chromatogram from the GC-MS analysis of thedegraded nicotine sample (at 30ºC, in the presence of air for 6 h; code N-O-t4)

Figure S7.Chromatogram from the GC-MS analysis of thedegraded nicotine sample (at 90ºC, in the presence of air for 6 h; code N-O-t6)

Figure S8.Chromatogram from the GC-MS analysis of therecovered nicotine and relatives from the NbCDE_r1 complex (peak from 13.4 min comes from the solvent used for extraction)

Figure S9.Chromatogram from the GC-MS analysis of therecovered nicotine and relatives from the NbCDE_r2 complex (peak from 13.4 min comes from the solvent used for extraction)

Figure S10.Chromatogram from the GC-MS analysis of therecovered nicotine and relatives from the NbCDE_r3 complex (peak from 13.4 min comes from the solvent used for extraction)

Figure S11.Chromatogram from the GC-MS analysis of therecovered nicotine and relatives from the NbCDE_t1 complex

Figure S12.Chromatogram from the GC-MS analysis of therecovered nicotine and relatives from the NbCDE_t2 complex (peak from 13.4 min comes from the solvent used for extraction)

Figure S13.Chromatogram from the GC-MS analysis of therecovered nicotine and relatives from the NbCDM_r1 complex (peak from 13.4 min comes from the solvent used for extraction)

Figure S14.Chromatogram from the GC-MS analysis of therecovered nicotine and relatives from the NbCDP_r1 complex

Figure S15.Chromatogram from the GC-MS analysis of therecovered nicotine and relatives from the degraded NbCDE-O-t4 complex (at 30ºC, in the presence of air for 6 h)

Figure S16.Chromatogram from the GC-MS analysis of therecovered nicotine and relatives from the degraded NbCDE-O-t5 complex (at 60ºC, in the presence of air for 6 h)

Figure S17.Chromatogram from the GC-MS analysis of therecovered nicotine and relatives from the degraded NbCDE-O-t6 complex (at 90ºC, in the presence of air for 6 h)

Thermogravimetry (TG) analysis for commercial βcyclodextrin and for nicotine/βcyclodextrin microparticles obtained in different conditions

Figure S18. Superimposed TG diagrams for β-cyclodextrin (red), nicotine (blue) and nicotine/β-cyclodextrin microparticles (1:1 ratio for nicotine:cyclodextrin, temperature of 50ºC) obtained by using the ethanol-water system (code NbCDE_r1)

Figure S19. Superimposed TG diagrams for β-cyclodextrin (red), nicotine (blue),and nicotine/β-cyclodextrin microparticles (2:1 ratio for nicotine:cyclodextrin, temperature of 50ºC) obtained by using the ethanol-water system (code NbCDE_r2)

Figure S20. Superimposed TG diagrams for β-cyclodextrin (red), nicotine (blue), and nicotine/β-cyclodextrin microparticles (3:1 ratio for nicotine:cyclodextrin, temperature of 50ºC) obtained by using the ethanol-water system (code NbCDE_r3)

Figure S21. Superimposed TG diagrams for β-cyclodextrin (red), nicotine (blue), and nicotine/β-cyclodextrin microparticles (1:1 ratio for nicotine:cyclodextrin, temperature of 30ºC) obtained by using the ethanol-water system (code NbCDE_t1)

Figure S22. Superimposed TG diagrams for β-cyclodextrin (red), nicotine (blue), and nicotine/β-cyclodextrin microparticles (1:1 ratio for nicotine:cyclodextrin, temperature of 70ºC) obtained by using the ethanol-water system (code NbCDE_t2)

Figure S23. Superimposed TG diagrams for β-cyclodextrin (red), nicotine (blue), and nicotine/β-cyclodextrin microparticles (1:1 ratio for nicotine:cyclodextrin, temperature of 50ºC, 2:1 ethanol:water ratio) obtained by using the ethanol-water system (code NbCDE_c1)

Figure S24. Superimposed TG diagrams for β-cyclodextrin (red), nicotine (blue), and nicotine/β-cyclodextrin microparticles (1:1 ratio for nicotine:cyclodextrin, temperature of 50ºC) obtained by using the methanol-water system (code NbCDM_r1)

Figure S25. Superimposed TG diagrams for β-cyclodextrin (red), nicotine (blue), and nicotine/β-cyclodextrin microparticles (1:1 ratio for nicotine:cyclodextrin, temperature of 50ºC) obtained by using the propanol-water system (code NbCDP_r1)

Karl Fischer water titration (KFT) for commercial βcyclodextrin and for nicotine/βcyclodextrin microparticles obtained in different conditions

Figure S26.Superimposed Karl Fischer water titration curves (V/m vs. Time) for commercial βCyclodextrin (bCD) and for Nicotine/βCyclodextrin complexes obtained by using ethanol-water solution method at nicotine: cyclodextrin ratio between 1:1 and 3:1 (codes NbCDE_r1,2,3)

Figure S27.Superimposed Karl Fischer water titration curves (V/m vs. Time) for commercial βCyclodextrin (bCD) and for Nicotine/βCyclodextrin complexes obtained by using ethanol-water solution method at different complexation temperatures (codes NbCDE_t1,2)

Figure S28.Superimposed Karl Fischer water titration curves (V/m vs. Time) for commercial βCyclodextrin (bCD) and for Nicotine/βCyclodextrin complexes obtained by using ethanol-, methanol, or propanol-water solution method (codes NbCDE_r1, NbCDM_r1,and NbCDP_r1)

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