Research Article
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Year 2024, Volume: 28 Issue: 6, 1982 - 1988, 28.06.2025
https://doi.org/10.29228/jrp.872

Abstract

References

  • [1] Xu D, Hu MJ, Wang YQ, Cui YL. Antioxidant activities of quercetin and its complexes for medicinal application. Molecules. 2019; 24(6): 1123. https://dx.doi.org/10.3390/molecules24061123.
  • [2] Harwood MA. Critical review of the data related to the safety of quercetin and lack of evidence of in vivo toxicity, including lack of genotoxic carcinogenic properties. Food Chem Toxicol. 2007; 45(11): 2179-205. https://dx.doi.org/10.1016/j.fct.2007.05.015.
  • [3] Gao L, Liu G, Wang X, Liu F, Xu Y, and Ma J. Preparation of a chemically stable quercetin formulation using nanosuspension technology. Int JPharm. 2011; 404(1–2): 231–237. https://dx.doi.org/10.1016/j.ijpharm.2010.11.009.
  • [4] Smith AJ, Kavuru P, Wojtas L, Zaworotko MJ, Shytle RD. Cocrystals of quercetin with improved solubility and oral bioavailability. Mol Pharmaceutics. 2011; 8(5): 1867–1876. https://dx.doi.org/10.1021/mp200209j.
  • [5] Bruni G, Maietta M, Maggi L, Mustarelli P, Ferrara C, Berbenni V, Milanese C, Girella A, Marini A. Preparation and physicochemical characterization of acyclovir cocrystals with improved dissolution properties. J Pharm Sci. 2013; 102(11): 4079–4086. https://dx.doi.org/10.1002/jps.23721.
  • [6] Krishnaiah YS. Pharmaceutical technologies for enhancing oral bioavailability of poorly soluble drugs. J Bioequiv Bioavailab. 2010; 2(2): 28–36. https://dx.doi.org/10.4172/jbb.1000027
  • [7] Wisudyaningsih B, Sallama S, Siswandono, Setyawan D. The effect of pH and cocrystal quercetin-isonicotinamide on quercetin solubility and its thermodynamic. Res J Pharm Technol. 2021; 14(9): 4657–4661. https://dx.doi.org/10.52711/0974-360X.2021.00809.
  • [8] Kakran M, Sahoo NG, Li L. Dissolution enhancement of quercetin through nanofabrication, complexation, and solid dispersion. Colloids Surf. B. 2011; 88(1): 121-130. https://dx.doi.org/10.1016/j.colsurfb.2011.06.020.
  • [9] Huang Y, Dai WG. Fundamental aspects of solid dispersion technology for poorly soluble drugs. Acta Pharm Sin B. 2014; 4(1): 18–25. https://dx.doi.org/10.1016/j.apsb.2013.11.001.
  • [10] Santos OMM, Reis MED, Jacon JT, Lino MES, Simões JS, Doriguetto AC. Polymorphism : An evaluation of the potential risk to the quality of drug products from the farmácia popular rede própria. Braz J Pharm Sci. 2014; 50 (1): 1–24. http://dx.doi.org/10.1590/S1984-82502011000100002.
  • [11] Wicaksono Y, Setyawan D, Siswandono. Formation of ketoprofen-malonic acid cocrystal by solvent evaporation method. Indones J Chem. 2017; 17(2): 161–166. https://dx.doi.org/10.22146/ijc.24884.
  • [12] Setyawan D, Oktavia IP, Farizka R, Sari R. Physicochemical Characterization and In Vitro Dissolution Test of Quercetin-Succinic Acid Co-crystals Prepared Using Solvent Evaporation. Turk J Pharm Sci. 2017. 14(3): 280–284. https://dx.doi.org/10.4274/tjps.16362.
  • [13] Wisudyaningsih B, Setyawan D, Siswodihardjo S. Co-crystallization of quercetin and isonicotinamide using solvent evaporation method. Trop J Pharm Res. 2019; 18 (4): 697-702. https://dx.doi.org/10.4314/tjpr.v18i4.3.
  • [14] Lucida H, Febriyenti F, Pradana R, Rahmatika L. Preparation of quercetin nanocrystals by planetary ball mill to increase the solubility and the dissolution profile. Der Pharm Lett. 2016; 8 (18): 53-58.
  • [15] Sahoo NG, Kakran M, Shaal LA, Li L, Muller RH, Pal M, Tan LP. Preparation and characterization of quercetin nanocrystals. J Pharm Sci. 2011; 100(6): 2379-2390. https://dx.doi:10.1002/jps.22446.
  • [16] Gozali D, Bahti HH, Soewandhi SN. Cocrystal formation between atorvastatin calcium and isonicotinamide and its characterization. J Indones Material Sci. 2012: 103–110. https://dx.doi.org/10.17146/jsmi.2014.15.2.4364.

Quercetin-maleic acid co-crystal engineering using solvent evaporation to ıncrease quercetin solubility

Year 2024, Volume: 28 Issue: 6, 1982 - 1988, 28.06.2025
https://doi.org/10.29228/jrp.872

Abstract

This study aims to produce quercetin-maleic acid cocrystals with an increase in solubility properties. The preparation of quercetin-maleic acid cocrystal (CQAM) was carried out by solvent evaporation method using ethanol as a solvent. The quercetin-maleic acid cocrystal preparation was formed with two different stoichiometric ratios, namely quercetin-maleic acid (1:1 and 1:3). Solubility tests on quercetin-maleic acid cocrystals were carried out in 50 mL citrate buffer pH 5 at 37±0.5°C. The characterization tests used were DSC, PXRD, FTIR, and SEM, while for the evaluation, solubility tests were carried out. The results of DSC, PXRD, FTIR and SEM showed the formation of a new solid with the type of crystalline solid, so it was concluded as a cocrystalline solid. The results of the solubility test showed that the solubility value of quercetin-maleic acid cocrystal (1:1 and 1:3) was greater than that of pure quercetin. Solubility result of pure quercetin, CQAM 1:1 and CQAM 1:3 were 0.545 ± 0.0351 mg/L; 2.237 ± 0.0258 mg/L; and 6.352 ± 0.0258 mg/L, respectively. Quercetin–maleic acid cocrystals (1:1) and (1:3) experienced an increase in solubility of 4.11 and 11.65 times, respectively, from pure quercetin.

References

  • [1] Xu D, Hu MJ, Wang YQ, Cui YL. Antioxidant activities of quercetin and its complexes for medicinal application. Molecules. 2019; 24(6): 1123. https://dx.doi.org/10.3390/molecules24061123.
  • [2] Harwood MA. Critical review of the data related to the safety of quercetin and lack of evidence of in vivo toxicity, including lack of genotoxic carcinogenic properties. Food Chem Toxicol. 2007; 45(11): 2179-205. https://dx.doi.org/10.1016/j.fct.2007.05.015.
  • [3] Gao L, Liu G, Wang X, Liu F, Xu Y, and Ma J. Preparation of a chemically stable quercetin formulation using nanosuspension technology. Int JPharm. 2011; 404(1–2): 231–237. https://dx.doi.org/10.1016/j.ijpharm.2010.11.009.
  • [4] Smith AJ, Kavuru P, Wojtas L, Zaworotko MJ, Shytle RD. Cocrystals of quercetin with improved solubility and oral bioavailability. Mol Pharmaceutics. 2011; 8(5): 1867–1876. https://dx.doi.org/10.1021/mp200209j.
  • [5] Bruni G, Maietta M, Maggi L, Mustarelli P, Ferrara C, Berbenni V, Milanese C, Girella A, Marini A. Preparation and physicochemical characterization of acyclovir cocrystals with improved dissolution properties. J Pharm Sci. 2013; 102(11): 4079–4086. https://dx.doi.org/10.1002/jps.23721.
  • [6] Krishnaiah YS. Pharmaceutical technologies for enhancing oral bioavailability of poorly soluble drugs. J Bioequiv Bioavailab. 2010; 2(2): 28–36. https://dx.doi.org/10.4172/jbb.1000027
  • [7] Wisudyaningsih B, Sallama S, Siswandono, Setyawan D. The effect of pH and cocrystal quercetin-isonicotinamide on quercetin solubility and its thermodynamic. Res J Pharm Technol. 2021; 14(9): 4657–4661. https://dx.doi.org/10.52711/0974-360X.2021.00809.
  • [8] Kakran M, Sahoo NG, Li L. Dissolution enhancement of quercetin through nanofabrication, complexation, and solid dispersion. Colloids Surf. B. 2011; 88(1): 121-130. https://dx.doi.org/10.1016/j.colsurfb.2011.06.020.
  • [9] Huang Y, Dai WG. Fundamental aspects of solid dispersion technology for poorly soluble drugs. Acta Pharm Sin B. 2014; 4(1): 18–25. https://dx.doi.org/10.1016/j.apsb.2013.11.001.
  • [10] Santos OMM, Reis MED, Jacon JT, Lino MES, Simões JS, Doriguetto AC. Polymorphism : An evaluation of the potential risk to the quality of drug products from the farmácia popular rede própria. Braz J Pharm Sci. 2014; 50 (1): 1–24. http://dx.doi.org/10.1590/S1984-82502011000100002.
  • [11] Wicaksono Y, Setyawan D, Siswandono. Formation of ketoprofen-malonic acid cocrystal by solvent evaporation method. Indones J Chem. 2017; 17(2): 161–166. https://dx.doi.org/10.22146/ijc.24884.
  • [12] Setyawan D, Oktavia IP, Farizka R, Sari R. Physicochemical Characterization and In Vitro Dissolution Test of Quercetin-Succinic Acid Co-crystals Prepared Using Solvent Evaporation. Turk J Pharm Sci. 2017. 14(3): 280–284. https://dx.doi.org/10.4274/tjps.16362.
  • [13] Wisudyaningsih B, Setyawan D, Siswodihardjo S. Co-crystallization of quercetin and isonicotinamide using solvent evaporation method. Trop J Pharm Res. 2019; 18 (4): 697-702. https://dx.doi.org/10.4314/tjpr.v18i4.3.
  • [14] Lucida H, Febriyenti F, Pradana R, Rahmatika L. Preparation of quercetin nanocrystals by planetary ball mill to increase the solubility and the dissolution profile. Der Pharm Lett. 2016; 8 (18): 53-58.
  • [15] Sahoo NG, Kakran M, Shaal LA, Li L, Muller RH, Pal M, Tan LP. Preparation and characterization of quercetin nanocrystals. J Pharm Sci. 2011; 100(6): 2379-2390. https://dx.doi:10.1002/jps.22446.
  • [16] Gozali D, Bahti HH, Soewandhi SN. Cocrystal formation between atorvastatin calcium and isonicotinamide and its characterization. J Indones Material Sci. 2012: 103–110. https://dx.doi.org/10.17146/jsmi.2014.15.2.4364.
There are 16 citations in total.

Details

Primary Language English
Subjects Pharmacy Management
Journal Section Research Article
Authors

Budipratiwi Wisudyaningsih This is me 0000-0002-1156-3808

Yudi Wicaksono 0000-0003-2302-8148

Elvina Herawati 0009-0001-4223-8063

Submission Date October 15, 2023
Acceptance Date March 6, 2024
Publication Date June 28, 2025
Published in Issue Year 2024 Volume: 28 Issue: 6

Cite

APA Wisudyaningsih, B., Wicaksono, Y., & Herawati, E. (2025). Quercetin-maleic acid co-crystal engineering using solvent evaporation to ıncrease quercetin solubility. Journal of Research in Pharmacy, 28(6), 1982-1988. https://doi.org/10.29228/jrp.872
AMA Wisudyaningsih B, Wicaksono Y, Herawati E. Quercetin-maleic acid co-crystal engineering using solvent evaporation to ıncrease quercetin solubility. J. Res. Pharm. July 2025;28(6):1982-1988. doi:10.29228/jrp.872
Chicago Wisudyaningsih, Budipratiwi, Yudi Wicaksono, and Elvina Herawati. “Quercetin-Maleic Acid Co-Crystal Engineering Using Solvent Evaporation to ıncrease Quercetin Solubility”. Journal of Research in Pharmacy 28, no. 6 (July 2025): 1982-88. https://doi.org/10.29228/jrp.872.
EndNote Wisudyaningsih B, Wicaksono Y, Herawati E (July 1, 2025) Quercetin-maleic acid co-crystal engineering using solvent evaporation to ıncrease quercetin solubility. Journal of Research in Pharmacy 28 6 1982–1988.
IEEE B. Wisudyaningsih, Y. Wicaksono, and E. Herawati, “Quercetin-maleic acid co-crystal engineering using solvent evaporation to ıncrease quercetin solubility”, J. Res. Pharm., vol. 28, no. 6, pp. 1982–1988, 2025, doi: 10.29228/jrp.872.
ISNAD Wisudyaningsih, Budipratiwi et al. “Quercetin-Maleic Acid Co-Crystal Engineering Using Solvent Evaporation to ıncrease Quercetin Solubility”. Journal of Research in Pharmacy 28/6 (July2025), 1982-1988. https://doi.org/10.29228/jrp.872.
JAMA Wisudyaningsih B, Wicaksono Y, Herawati E. Quercetin-maleic acid co-crystal engineering using solvent evaporation to ıncrease quercetin solubility. J. Res. Pharm. 2025;28:1982–1988.
MLA Wisudyaningsih, Budipratiwi et al. “Quercetin-Maleic Acid Co-Crystal Engineering Using Solvent Evaporation to ıncrease Quercetin Solubility”. Journal of Research in Pharmacy, vol. 28, no. 6, 2025, pp. 1982-8, doi:10.29228/jrp.872.
Vancouver Wisudyaningsih B, Wicaksono Y, Herawati E. Quercetin-maleic acid co-crystal engineering using solvent evaporation to ıncrease quercetin solubility. J. Res. Pharm. 2025;28(6):1982-8.