Solubilities of Betulinic Acid in Thirteen Organic Solvents at Different Temperatures
Abstract
The solubilities of betulinic acid in methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 1-pentanol, 1-hexanol, ethyl formate, ethyl acetate, butyl acetate, acetone, and tetrahydrofuran were measured by an analytical method in the temperature range of (278.2 to 318.2) K. The experimental data were correlated with a three-parameter empirical equation and UNIQUAC model, respectively. The calculated solubilities showed good agreement with the experimental data over this temperature range. Furthermore, the relation of the solubilities and the crystal habit were discussed.
Cited By
This article is cited by 56 publications.
- Zilong Cui, Jingling Ye, Liang Yao, Zhi Wang, Ting Wang, Yonghong Hu. Determination and Analysis of Solubility of l-Prolinamide in Ten Pure Solvents and Three Binary Solvent Mixtures at Different Temperatures (T = 278.15–323.15 K). Journal of Chemical & Engineering Data 2021, 66
(2)
, 1172-1184. https://doi.org/10.1021/acs.jced.0c00961
- Yuanyun Gu, Wenge Yang, Aixiang Hao, Qiang Xu, Yonghong Hu. Determination and Analysis of Solubility of 3-Bromo-2-Methylbenzoic Acid in Different Solvent Systems at Different Temperatures (T = 278.15–328.15 K). Journal of Chemical & Engineering Data 2020, 65
(4)
, 1571-1582. https://doi.org/10.1021/acs.jced.9b01007
- Yuanyun Gu, Wenge Yang, Aixiang Hao, Qiang Xu, Yonghong Hu. Determination and Analysis of Solubility of 2-Chloromethyl-4-methylquinazoline in Different Solvent Systems at Different Temperatures (T = 281.15–331.15 K). Journal of Chemical & Engineering Data 2020, 65
(4)
, 1736-1746. https://doi.org/10.1021/acs.jced.9b01068
- Li Wang, Wenge Yang, Yiyi Song, Yuanyun Gu. Solubility Measurement, Correlation, and Molecular Interactions of 3-Methyl-6-nitroindazole in Different Neat Solvents and Mixed Solvents from T = 278.15 to 328.15 K. Journal of Chemical & Engineering Data 2019, 64
(8)
, 3260-3269. https://doi.org/10.1021/acs.jced.8b01256
- Behnaz Asadzadeh, Jialun Zhong, Weidong Yan. Solid–Liquid Equilibrium of Rebaudioside A in Pure and Binary Mixed Solvents at T = (288.15 to 328.15) K. Journal of Chemical & Engineering Data 2018, 63
(11)
, 4269-4276. https://doi.org/10.1021/acs.jced.8b00780
- Rongjie Wang, Benxian Shen, Hui Sun, Jigang Zhao. Measurement and Correlation of the Solubilities of Sulfur S8 in 10 Solvents. Journal of Chemical & Engineering Data 2018, 63
(3)
, 553-558. https://doi.org/10.1021/acs.jced.7b00699
- Dong-Fang Zhao, Li-Sheng Wang, Jian Sun, and Chuan-Ming Chen . Measurement and Correlation of Solubility of Resorcinol Bis(cyclic 2,2-dimethyl-1,3-propanediol phosphate) in Selected Solvents from T = 293.15 to 333.15 K. Journal of Chemical & Engineering Data 2017, 62
(12)
, 4327-4336. https://doi.org/10.1021/acs.jced.7b00695
- Dong-Fang Zhao, Li-Sheng Wang, Jian Sun, and Chuan-Ming Chen . Solid–Liquid Phase Equilibrium of N,N′-Piperazinebis(neopentylglycol)phosphoramidate in Selected Solvents from T = (293.15 to 333.15) K. Journal of Chemical & Engineering Data 2017, 62
(7)
, 2101-2109. https://doi.org/10.1021/acs.jced.7b00206
- Jianfeng Hao, Wenge Yang, Hongjie Li, Shimin Fan, Wangdan Zhao, and Yonghong Hu . Solubility of 4-Methylsulfonylacetophenone in Nine Pure Solvents and (Ethyl Acetate + n-Hexane) Binary Solvent Mixtures from 278.15 K to 328.15 K. Journal of Chemical & Engineering Data 2017, 62
(1)
, 236-242. https://doi.org/10.1021/acs.jced.6b00617
- Kangli You, Baohe Wang, Shuang Chen, and Dongwei Wei . Measurement and Correlation of the Solubility of Antioxidant 626 in Alcohols. Journal of Chemical & Engineering Data 2016, 61
(3)
, 1205-1209. https://doi.org/10.1021/acs.jced.5b00823
- Ning Tang, Wei Shi, and Weidong Yan . Modified Method for Measuring the Solubility of Pharmaceutical Compounds in Organic Solvents by Visual Camera. Journal of Chemical & Engineering Data 2016, 61
(1)
, 35-40. https://doi.org/10.1021/acs.jced.5b00122
- Gang Wu, Yonghong Hu, Pengfei Gu, Wenge Yang, Zhiwen Ding, Chunxiao Wang, and Yonggen Qian . Solubility and Solution Thermodynamics of Gibberellin A4 in Different Organic Solvents from 278.15 K to 333.15 K. Journal of Chemical & Engineering Data 2015, 60
(7)
, 2104-2109. https://doi.org/10.1021/acs.jced.5b00190
- Qi Zhang, Yonghong Hu, Yang Yang, Cuicui Cao, Limin Cheng, Yonglan Li, and Wenge Yang . Thermodynamic Models for Determination of the Solubility of the (1:1) Complex of (Urea + l-Malic Acid) in (Methanol + Acetonitrile) Binary Solvent Mixtures. Journal of Chemical & Engineering Data 2015, 60
(6)
, 1608-1613. https://doi.org/10.1021/je500991b
- Bianhua Wu, Youwei Cheng, and Xi Li . Thermodynamic Properties and Crystal Structures of the Adductive 2,6-Naphthalenedicarboxylic Acid Crystallization with N,N-Dimethyl Acetamide and N-Methyl Pyrrolidone. Journal of Chemical & Engineering Data 2012, 57
(2)
, 406-411. https://doi.org/10.1021/je2009973
- Altynaray T. Takibayeva, Gulistan K. Zhumabayeva, Abdigali A. Bakibaev, Olga V. Demets, Maria V. Lyapunova, Elena A. Mamaeva, Rakhmetulla Sh. Yerkassov, Rymchan Z. Kassenov, Marat K. Ibrayev. Methods of Analysis and Identification of Betulin and Its Derivatives. Molecules 2023, 28
(16)
, 5946. https://doi.org/10.3390/molecules28165946
- Ivo S. Azenha, Mário M. Q. Simões, Adélio Mendes, Carlos M. Silva. Adsorbents, mobile phases, and strategies for the chromatographic separation of betulinic, oleanolic, and ursolic acids. Biomass Conversion and Biorefinery 2023, 14 https://doi.org/10.1007/s13399-022-03723-3
- Jinlu Qu, Yuan Zhang, Dingqiang Lu, Xinxian Wang. Solubility parameter and solution thermodynamic properties of Form I Trimebutine maleate in six mono-solvents and three binary mixed solvents at different temperatures. Journal of Molecular Liquids 2022, 367 , 120503. https://doi.org/10.1016/j.molliq.2022.120503
- Ming Liu, Wen-dong Liu, Yong-xiang Li. Solubility, Hansen solubility parameter, molecular simulation and apparent thermodynamic analysis of 5-Fluorouracil in four binary solvents. Journal of Molecular Liquids 2022, 362 , 119759. https://doi.org/10.1016/j.molliq.2022.119759
- Wen-dong Liu. Solubility, Hansen solubility parameter, molecular simulation and thermodynamic analysis of N-methyl-3,4,5-trinitropyrazole at various temperatures. Journal of Molecular Liquids 2022, 360 , 119572. https://doi.org/10.1016/j.molliq.2022.119572
- Kalyani Pathak, Manash P. Pathak, Riya Saikia, Urvashee Gogoi, Jon J. Sahariah, James H. Zothantluanga, Abhishek Samanta, Aparoop Das. Cancer Chemotherapy
via
Natural Bioactive Compounds. Current Drug Discovery Technologies 2022, 19
(4)
https://doi.org/10.2174/1570163819666220331095744
- Wen-dong Liu, Yong-xiang Li, Duan-lin Cao, Zi-yang Li. Solubility and thermodynamic properties of an energetic intermediate in four binary solvents (water + n-butanol, n-pentanol, isobutanol and isoamyl alcohol). Journal of Molecular Liquids 2021, 342 , 117195. https://doi.org/10.1016/j.molliq.2021.117195
- Wen-Dong Liu, Yong-Xiang Li, Duan-Lin Cao, Heng-Jie Guo, Zi-Yang Li. Solubility determination and correlation for 3-nitropyrazole in four binary solvents (water + methanol, ethanol, 1-propanol and acetone) from 283.15 K to 323.15 K. Journal of Molecular Liquids 2021, 342 , 117332. https://doi.org/10.1016/j.molliq.2021.117332
- Zilong Cui, Zhiruo Zhao, Liang Yao, Yonghong Hu. Determination and analysis of solubility of brassinolide in different solvent systems at different temperatures (T = 278.15–323.15 K). Journal of Molecular Liquids 2021, 340 , 117316. https://doi.org/10.1016/j.molliq.2021.117316
- Zilong Cui, Liang Yao, Jingling Ye, Zhi Wang, Yonghong Hu. Solubility measurement and thermodynamic modelling of curcumin in twelve pure solvents and three binary solvents at different temperature (T = 278.15–323.15 K). Journal of Molecular Liquids 2021, 338 , 116795. https://doi.org/10.1016/j.molliq.2021.116795
- Hao-qi Guo, Yong-xiang Li, Yu-lin Yang, Zi-yang Li. Solubility, thermodynamic modeling and Hansen solubility parameter of a new type of explosive in four binary solvents (benzene + ethanol, n-propanol, n-butanol and isoamyl alcohol) from 283.15 K to 323.15 K. Journal of Molecular Liquids 2021, 328 , 114842. https://doi.org/10.1016/j.molliq.2020.114842
- Cristian Suárez-Rozas, Bruce K. Cassels. Betulinic acid. 2021, 117-142. https://doi.org/10.1016/B978-0-12-822923-1.00007-8
- Asim Halder, Megha Jethwa, Pritha Mukherjee, Subarna Ghosh, Suvadra Das, A. B. M. Helal Uddin, Arup Mukherjee, Urmi Chatterji, Partha Roy. Lactoferrin-tethered betulinic acid nanoparticles promote rapid delivery and cell death in triple negative breast and laryngeal cancer cells. Artificial Cells, Nanomedicine, and Biotechnology 2020, 48
(1)
, 1362-1371. https://doi.org/10.1080/21691401.2020.1850465
- Asim Halder, Divanshu Shukla, Suvadra Das, Partha Roy, Arup Mukherjee, Bhaskar Saha. Lactoferrin-modified Betulinic Acid-loaded PLGA nanoparticles are strong anti-leishmanials. Cytokine 2018, 110 , 412-415. https://doi.org/10.1016/j.cyto.2018.05.010
- Naga Sai Visweswar Kambhampati, Swayamsiddha Kar, Sai Siva Kumar Pinnepalli, Janardhana Chelli, Mukesh Doble. Microbial cyclic β-(1 → 3),(1 → 6)-glucans as potential drug carriers: Interaction studies between cyclic β-glucans isolated from Bradyrhizobium japonicum and betulinic acid. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2018, 203 , 494-500. https://doi.org/10.1016/j.saa.2018.05.106
- Ankit Saneja, Divya Arora, Robin Kumar, Ravindra Dhar Dubey, Amulya K. Panda, Prem N. Gupta. Therapeutic applications of betulinic acid nanoformulations. Annals of the New York Academy of Sciences 2018, 1421
(1)
, 5-18. https://doi.org/10.1111/nyas.13570
- Heng-jie Guo, Xin Dang, Feng Yang, Duan-lin Cao, Yong-xiang Li, Wang-hua Hu, Zhen-ming Jiang, Zhi-hua Li, Zi-yang Li, Luo-wen Zhang. Solubility and thermodynamic properties of a kind of explosives in four binary solvents. Journal of Molecular Liquids 2017, 247 , 313-327. https://doi.org/10.1016/j.molliq.2017.09.097
- Eik Czarnotta, Mariam Dianat, Marcel Korf, Fabian Granica, Juliane Merz, Jérôme Maury, Simo A. Baallal Jacobsen, Jochen Förster, Birgitta E. Ebert, Lars M. Blank. Fermentation and purification strategies for the production of betulinic acid and its lupane‐type precursors in
Saccharomyces cerevisiae. Biotechnology and Bioengineering 2017, 114
(11)
, 2528-2538. https://doi.org/10.1002/bit.26377
- Xinxin Zhao, Wenge Yang, Wangdan Zhao, Hongjie Li, Shimin Fan, Jianfeng Hao, Jian Zhang, Huace Sheng. Apparent thermodynamic models for determination of the solubility of N-acetyl-1,3-phenylenediamine in eight pure solvents and two different miscible systems at T= (278.15–323.15) K. Journal of Molecular Liquids 2017, 243 , 187-195. https://doi.org/10.1016/j.molliq.2017.08.030
- Tianhua Huang, Dingqiang Lu, Xiuquan Ling, Xinxian Wang, Tongqi Liu, Fangfang Shen, Kefei He. Thermodynamic models for determination of the solid-liquid equilibrium of istradefylline in ethyl acetate plus (isopropanol, tetrahydrofuran, acetone) binary solvent mixtures. The Journal of Chemical Thermodynamics 2017, 111 , 31-40. https://doi.org/10.1016/j.jct.2017.03.015
- Chen Yang, Qi Li, Yong Wu. Thermodynamic models for determination of solid-liquid equilibrium of the 4-methylbenzoic acid in pure and binary organic solvents. Journal of Molecular Liquids 2017, 238 , 432-439. https://doi.org/10.1016/j.molliq.2017.05.046
- Tao Li, Renlun Deng, Gang Wu, Pengfei Gu, Yonghong Hu, Wenge Yang, Yemin Yu, Yuhao Zhang, Chen Yang. Thermodynamic models for determination of solid–liquid equilibrium of the 6-benzyladenine in pure and binary organic solvents. The Journal of Chemical Thermodynamics 2017, 106 , 208-215. https://doi.org/10.1016/j.jct.2016.12.002
- Fangfang Shen, Dingqiang Lu, Xiuquan Ling, Xinxian Wang, Tongqi Liu, Tianhua Huang, Kefei He. Thermodynamic analysis and calculation of solubility of Memantine hydrochloride in ethanol plus (acetonitrile, water, ethyl acetate) binary solvent mixtures. Journal of Molecular Liquids 2017, 229 , 58-66. https://doi.org/10.1016/j.molliq.2016.12.051
- Yong Chen, Xin Xu, Li Xie. Thermodynamic parameters on corresponding solid-liquid equilibrium of hydroxyapatite in pure and mixture organic solvents. Journal of Molecular Liquids 2017, 229 , 189-197. https://doi.org/10.1016/j.molliq.2016.12.082
- Maicon Roberto Kviecinski, Isabela Machado Barbosa David, Flávia de Souza Fernandes, Marina dos Reis Correa, Morgana Miranda Clarinda, Amanda Fernandes Freitas, Jane da Silva, Marta Gava, Simony Davet Müller, Drielly Florentino, Fabrícia Petronilho, Diego Moterle, Luiz Alberto Kanis, Rozangela Curi Pedrosa. Healing effect of
Dillenia indica
fruit extracts standardized to betulinic acid on ultraviolet radiation-induced psoriasis-like wounds in rats. Pharmaceutical Biology 2017, 55
(1)
, 641-648. https://doi.org/10.1080/13880209.2016.1266672
- Wenzhe Ji, Dingqiang Lu, Shaoning Yang, Tongqi Liu, Xinxian Wang, Xiuquan Ling. Solubility and solution thermodynamics of cetilistat in water and (acetone, isopropyl alcohol, acetonitrile) binary solvent mixtures. Journal of Molecular Liquids 2016, 224 , 1380-1387. https://doi.org/10.1016/j.molliq.2016.10.127
- Gang Wu, Yonghong Hu, Pengfei Gu, Wenge Yang, Chunxiao Wang, Zhiwen Ding, Renlun Deng, Tao Li, Housheng Hong. Determination and correlation thermodynamic models for solid–liquid equilibrium of the Nifedipine in pure and mixture organic solvents. The Journal of Chemical Thermodynamics 2016, 102 , 333-340. https://doi.org/10.1016/j.jct.2016.07.035
- Tongqi Liu, Dingqiang Lu, Shaoning Yang, Xiuquan Ling, Wenzhe Ji. Solubility and solution thermodynamics of Meldrum's adduct in ethyl acetate plus (acetonitrile, ethanol, hexane) binary solvent mixtures. Journal of Molecular Liquids 2016, 220 , 354-363. https://doi.org/10.1016/j.molliq.2016.04.096
- Yonghong Hu, Gang Wu, Pengfei Gu, Wenge Yang, Chunxiao Wang, Zhiwen Ding, Yang Cao. Thermodynamic models for determination of the solubility of omeprazole in pure and mixture organic solvents from T=(278.15 to 333.15)K. The Journal of Chemical Thermodynamics 2016, 94 , 177-185. https://doi.org/10.1016/j.jct.2015.11.005
- Hongjie Li, Wenge Yang, Jianfeng Hao, Shimin Fan, Shouhai Yang, Qirun Guo. Experimental measurement and thermodynamic models for solid–liquid equilibrium of 3-amino-1-adamantanol in different pure solvents and in (H2O + ethanol) binary solvent mixtures. Journal of Molecular Liquids 2016, 215 , 127-134. https://doi.org/10.1016/j.molliq.2015.12.052
- Qi Zhang, Yonghong Hu, Yang Yang, Cuicui Cao, Limin Cheng, Ying Shi, Wenge Yang. Thermodynamic analysis for determination of solid–liquid equilibrium of dibenzothiophene in a binary solvent of formic acid and butan-1-ol between (278.15 and 333.15) K. Fluid Phase Equilibria 2016, 408 , 94-99. https://doi.org/10.1016/j.fluid.2015.08.023
- Qi Zhang, Yang Yang, Limin Cheng, Cuicui Cao, Zhiwen Ding, Chunxiao Wang, Wenge Yang, Yonghong Hu, Yonglan Li. Thermodynamic models for determination of the solubility of dl-malic acid in methanol plus (acetonitrile, N,N-dimethylformamide, isopropyl alcohol) binary solvent mixtures. The Journal of Chemical Thermodynamics 2015, 85 , 148-154. https://doi.org/10.1016/j.jct.2015.02.002
- Qi Zhang, Yang Yang, Cuicui Cao, Limin Cheng, Ying Shi, Wenge Yang, Yonghong Hu. Thermodynamic models for determination of the solubility of dibenzothiophene in (methanol+acetonitrile) binary solvent mixtures. The Journal of Chemical Thermodynamics 2015, 80 , 7-12. https://doi.org/10.1016/j.jct.2014.08.012
- Wei Shi, Yong Cheng, Yundong Shao, Weidong Yan. Thermodynamic properties of betulinic acid in THF+water mixed solvents at different temperatures. Thermochimica Acta 2014, 598 , 1-6. https://doi.org/10.1016/j.tca.2014.10.026
- Xiaoying Wang, Ningbo Gong, Shiying Yang, Guanhua Du, Yang Lu. Studies on Solvatomorphism of Betulinic Acid. Journal of Pharmaceutical Sciences 2014, 103
(9)
, 2696-2703. https://doi.org/10.1002/jps.23853
- Yang Yang, Qi Zhang, Cuicui Cao, Limin Cheng, Ying Shi, Wenge Yang, Yonghong Hu. Solubility and solution thermodynamics of 2,5-thiophenedicarboxylic acid in (water + ethanol) binary solvent mixtures. Thermochimica Acta 2014, 592 , 52-57. https://doi.org/10.1016/j.tca.2014.08.002
- Yonghong Hu, Wenbiao Zhi, Mengmeng Liang, Zheng Cao, Wenge Yang. Solubility and solution thermodynamics of myo-inositol in (water+acetic acid) binary solvent mixtures. Fluid Phase Equilibria 2014, 365 , 58-63. https://doi.org/10.1016/j.fluid.2013.11.045
- Jie-Ping Fan, Chun-Fang Xie, Yun-Song Luo, Fa-tian Song, Xiao-Ying Liu, Jian-Hang Zhu, Xue-Hong Zhang. Solubilities of betulin and betulinic acid in sodium hydroxide aqueous solutions of varied mole fraction at temperatures from 283.2K to 323.2K. The Journal of Chemical Thermodynamics 2013, 67 , 1-4. https://doi.org/10.1016/j.jct.2013.07.014
- Wenbiao Zhi, Yonghong Hu, Wenge Yang, Yumei Kai, Zheng Cao. Measurement and correlation of solubility of d-sorbitol in different solvents. Journal of Molecular Liquids 2013, 187 , 201-205. https://doi.org/10.1016/j.molliq.2013.07.014
- V. A. Drebushchak, M. A. Mikhailenko, Tatyana P. Shakhtshneider, Svetlana A. Kuznetsova. Melting of orthorhombic betulin. Journal of Thermal Analysis and Calorimetry 2013, 111
(3)
, 2005-2008. https://doi.org/10.1007/s10973-012-2235-4
- Jie-Ping Fan, Yan-Long Xie, Ze-You Tian, Rui Xu, Yu Qin, Lie Li, Jian-Hang Zhu. Solubilities of evodiamine in twelve organic solvents from T= (283.2 to 323.2) K. The Journal of Chemical Thermodynamics 2013, 58 , 288-291. https://doi.org/10.1016/j.jct.2012.11.021
- René Csuk, Ronny Sczepek, Bianka Siewert, Christoph Nitsche. Cytotoxic betulin-derived hydroxypropargylamines trigger apoptosis. Bioorganic & Medicinal Chemistry 2013, 21
(2)
, 425-435. https://doi.org/10.1016/j.bmc.2012.11.016