Capecitabine is a widely used anticancer prodrug of 5-fluorouracil, but up to the present time there is no solubility data reported other than in supercritical carbon dioxide . In this paper, by the polythermal method, the solubility data of capecitabine in fifteen pure lower alcohols and water with methanol mixture solvents were measured from 278.15 K to 323.15 K under atmospheric pressure. The results show that the solubility of capecitabine in linear lower alcohols are bigger than that in corresponding branch chain lower alcohols, and decrease with the increasing of carbons in alkyl of alcohols. Moreover, the solubility of capecitabine increases with the increasing of temperature and mole fraction of methanol in the binary solvent mixtures of water + methanol. To expand industrial application of experimental solubility data of capecitabine in recrystallization, the values measured in selected pure lower alcohols are correlated using the modified Apelblat equation, the Buchowski-Ksiazczak-pletrzyk equation, the van't Hoff equation, the Wilson model and the NRTL model; And for the binary solvent system, the modified Apelblat equation and Jouyban-Acree model are used to correlate the solubility data. By evaluating the deviations between experimental and correlated data, all the correlated data by six models used in this research show comparable precision to those attained by careful experimental measurement. Moreover, some apparent thermodynamic quantities (Δ S d o , Δ H d o , Δ G d o , % ζ H and % ζ TS ) of the dissolution processes of capecitabine in selected solvents and temperature range studied were calculated by the parametric van't Hoff equation. According to the calculation, the dissolution of capecitabine in lower alcohols and water with methanol mixture solvents is an endothermic and entropy-driven process. The solubility and apparent dissolution characteristics of capecitabine in this paper would provide basic support for industrial design and further studies.
Kemeng Shi,Christian Marcus Pedersen,Zhaohui Guo,Yanqiu Li,Hongyan Zheng,Yan Qiao,Tuoping Hu,Yingxiong Wang
The tautomer distributions of d ‑fructose, a popular model compound for biorefinery , in various lower alcohols and DMSO‑ d 6 (ROHs/DMSO‑ d 6 ) mixtures at 298 K were investigated by quantitative 13 C NMR. The tautomer distributions of d ‑fructose in ethanol/DMSO‑ d 6 and methanol/DMSO‑ d 6 with different volume ratios of alcohols to DMSO‑ d 6 were also examined. For these normal alcohols (methanol, ethanol, n ‑propanol and n ‑butanol)/DMSO‑ d 6 , the tautomer distribution of d ‑fructose in methanol/DMSO‑ d 6 exhibited the shortest equilibration time (46 h) and the lowest concentration of β‑furanose (39.0%) at equilibrium. The fraction of fructofuranose (α‑furanose and β‑furanose) at equilibrium and time needed to reach equilibrium in branched chain alcohols/DMSO‑ d 6 obey the following order: 2‑propanol/DMSO‑ d 6 (62.2%, 320 h) > tert ‑butanol/DMSO‑ d 6 (61.6%, 307 h) > 2‑butanol/DMSO‑ d 6 (60.6%, 216 h) > isobutanol/DMSO‑ d 6 (57.8%, 134 h). For the diols/DMSO‑ d 6 , the time for the tautomer distribution of d ‑fructose to reach the equilibrium was found to be: 1,4‑butanediol/DMSO‑ d 6 (113 h) > 1,2‑propanediol/DMSO‑ d 6 (38 h) > ethylene glycol/DMSO‑ d 6 (36 h). For ethanol/DMSO‑ d 6 and methanol/DMSO‑ d 6 with respectively different volume ratios, the experimental results showed that the high concentration of ethanol or methanol increases the conversion rate of tautomers.
Lower alcohols (C1–C7) have a close relationship with our lives and some of them are harmful to our body's health. For example, liquor mixed with a tiny amount of methanol is harmful to our health. Much of this study is about identifying one or two low-level alcohols. How to detect low-level alcohol and high-throughput and distinguish between analogues of alcohol remains a tremendous challenge. In this study, a new large ring Schiff base Sm(III) complex (Sm-2r) is synthesized with a double emission matrix using the template method. Its dynamic imine bond (CN) and organic ligands (H2L2r) with molecular rotor properties can respond to changes in viscosity and polarity in external environments. The PCA method is used to turn the data matrix into a fingerprint spectrum to distinguish different alcohols (C1–C7). Sm-2r enables the quantization of cyclopropyl and glycerol. Linear ranges of cyclopropanol and glycerol are 0–9.0% and 0–3.0% (v/v), respectively. In addition, Sm-2r has an excellent ability to distinguish the mixtures of n-PrOH and i-PrOH, C5H9OH and C6H11OH, n-PeOH and n-HeOH, 1,3-PDO and 1,2-PDO, MeOH and EtOH, 1,2-EG and 1,2-PDO at different volume ratios. We have provided a way to distinguish alcohol species based on their molecular polarity and viscosity.
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