Skip to main content

Advertisement

SpringerLink
Log in

Solubility and Solution Thermodynamic Properties of 4-(4-Hydroxyphenyl)-2-butanone (Raspberry Ketone) in Different Pure Solvents

  • Published:
Journal of Solution Chemistry Aims and scope Submit manuscript

Abstract

The solubility of 4-(4-hydroxyphenyl)-2-butanone (raspberry ketone) in six pure solvents was experimentally determined at temperatures ranging from 283.15 to 313.15 K under the pressure 0.10 MPa by employing a gravimetrical method. The experimental results indicate that the solubility of raspberry ketone in all studied solvents is temperature dependent, a rise in temperature brings about an increase in solubility. The experimental solubility data of raspberry ketone in six pure solvents (acetone, ethanol, ethyl acetate, n-propyl alcohol, n-butyl alcohol, and distilled water) was correlated by using several commonly used thermodynamic models, including the Apelblat, van’t Hoff and λh equations. The results of the error analysis indicate that the van’t Hoff equation was able to give more accurate and reliable predictions of solubility with root-mean-square deviation less than 0.56%. Furthermore, the changes of dissolution enthalpies (Δdiss H°), dissolution entropies (Δdiss S°) and dissolution Gibbs energies (Δdiss G°) of raspberry ketone in the solvents studied were estimated by the van’t Hoff equation. The positive value of Δdiss H°, Δdiss S°, and Δdiss G° indicated that these dissolution processes of raspberry ketone in the solvents studied were all endothermic and enthalpy-driven.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Ogawa, Y., Akamatsu, M., Hotta, Y., Hosoda, A., Tamura, H.: Effect of essential oils, such as raspberry ketone and its derivatives, on antiandrogenic activity based on in vitro reporter gene assay. Med. Chem. Lett. B 20, 2111–2114 (2010)

    Article  CAS  Google Scholar 

  2. Kosjek, B., Stampfer, W., Deursen, R.V., Faber, K., Kroutil, W.: Efficient production of raspberry ketone via ‘green’ biocatalytic oxidation. Tetrahedron 59, 9517–9521 (2003)

    Article  CAS  Google Scholar 

  3. Harada, N., Okajima, K., Narimatsu, N., Kurihara, H., Nakagata, N.: Effect of topical application of raspberry ketone on dermal production of insulin-like growth factor-I in mice and on hair growth and skin elasticity in humans. Growth Horm IGF Res. 18, 335–344 (2008)

    Article  CAS  Google Scholar 

  4. Larsen, M., Poll, L.: Odour thresholds of some important aroma compounds in raspberries. Z. Lebensm Unters Forsch. 191, 129–131 (1990)

    Article  CAS  Google Scholar 

  5. Bredsdorff, L., Wedebye, E.B., Nikolov, N.G., Hallas-Møller, T., Pilegaard, K.: Raspberry ketone in food supplements – High intake, few toxicity data – a cause for safety concern? Regul. Toxicol. Pharm. 73, 196–200 (2015)

    Article  CAS  Google Scholar 

  6. Hoelderich, W.F., Ritzerfeld, V.: Preparation of a raspberry ketone precursor in the presence of rare earth oxide catalysts. Appl. Catal. A: General 504, 654–663 (2015)

    Article  CAS  Google Scholar 

  7. Shimoda, K., Harada, T., Hamada, H., Nakajima, N., Hamada, H.: Biotransformation of raspberry ketone and zingerone by cultured cells of Phytolacca americana. Phytochemistry. 68, 487–492 (2007)

    Article  CAS  Google Scholar 

  8. Takiyama, H.: Supersaturation operation for quality control of crystalline particles in solution crystallization. Adv. Powder Technol. 23, 273–278 (2012)

    Article  CAS  Google Scholar 

  9. Parimaladevi, P., Srinivasan, K.: Influence of supersaturation level on the morphology of a-lactose monohydrate crystals. Int. Dairy J. 39, 301–311 (2014)

    Article  CAS  Google Scholar 

  10. Jiang, L.K., Wang, L.S., Du, C.J., Sun, G.Q., Qi, C.M.: Measurement and correlation of the solubilities of tetra(5,5-dimethyl-1,3-dioxaphosphorinanyl-2-oxy) neopentane in different pure solvents. Fluid Phase Equilib. 367, 117–124 (2014)

    Article  CAS  Google Scholar 

  11. Matsuda, H., Mori, K., Tomioka, M., Kariyasu, N., Fukami, T., Kurihara, K., Tochigi, K., Tomono, K.: Determination and prediction of solubilities of active pharmaceutical ingredients in selected organic solvents. Fluid Phase Equilib. 406, 116–123 (2015)

    Article  CAS  Google Scholar 

  12. Liu, Z.K., Yin, Q.X., Zhang, X.W., Zhang, H., Gong, J.B., Wang, J.K.: Measurement and correlation of the solubility of 4,4-oxydianiline in different organic solvents. Fluid Phase Equilib. 356, 38–45 (2013)

    Article  CAS  Google Scholar 

  13. Zhu, L., Wang, L.Y., Li, X.C., Sha, Z.L., Wang, Y.F., Yang, L.B.: Experimental determination and correlation of the solubility of 4-hydroxy-2,5-dimethyl-3(2H)-furanone (DMHF) in six different solvents. J. Chem. Thermodyn. 91, 369–377 (2015)

    Article  CAS  Google Scholar 

  14. Xiao, L.P., Wang, Y.L., Yang, J.X., Yuan, F.H., Jiang, C., Hou, B.H., Xie, C.: Determination and correlation of solubility of 4′-bromomethyl-2-cyanobiphenyl in acetone + (ethanol, n-propanol, n-butanol) mixtures. J. Chem. Thermodyn. 102, 199–210 (2016)

    Article  CAS  Google Scholar 

  15. Apelblat, A., Manzurola, E.: Solubilities of o-acetylsalicylic, 4-aminosalicylic, 3,5-dinitrosalicylic, and p-toluic acid, and magnesium-DL-aspartate in water from T = (278 to 348) K. J. Chem. Thermodyn. 31, 85–91 (1999)

    Article  CAS  Google Scholar 

  16. Kai, Y.M., Hu, Y.H., Liu, Y., Liang, M.M., Yang, W.G., Xi, Y.: The solubility of mercaptosuccinic acid in water + (methanol, ethanol, acetone) mixtures from (278.15 to 333.15 K). Fluid Phase Equilib. 361, 282–288 (2014)

    Article  CAS  Google Scholar 

  17. Wang, G., Wang, Y.L., Ma, Y.G., Hao, H.X., Luan, Q.H., Wang, H.H.: Determination and correlation of cefuroxime acid solubility in (acetonitrile + water) mixtures. J. Chem. Thermodyn. 77, 144–150 (2014)

    Article  CAS  Google Scholar 

  18. Sunsandee, N., Hronec, M., Štolcová, M., Leepipatpiboon, N., Pancharoen, U.: Thermodynamics of the solubility of 4-acetylbenzoic acid in different solvents from 303.15 to 473.15 K. J. Mol. Liq. 180, 252–259 (2013)

    Article  CAS  Google Scholar 

  19. Buchowski, H., Ksiazczak, A., Pietrzyk, S.: Solvent activity along a saturation line and solubility of hydrogen-bonding solids. J. Phys. Chem. 84, 975–979 (1980)

    Article  CAS  Google Scholar 

  20. Soltanpour, S., Gharagozlu, A.: Piroxicam Solubility in binary and ternary solvents of polyethylene glycols 200 or 400 with ethanol and water at 298.2 K: experimental data report and modeling. J. Solution Chem. 44, 1407–1423 (2015)

    Article  CAS  Google Scholar 

  21. Morimoto, C., Satoh, Y., Hara, M., Inoue, S., Tsujita, T., Okuda, H.: Anti-obese action of raspberry ketone. Life Sci. 77, 194–204 (2005)

    Article  CAS  Google Scholar 

  22. Koeduka, T., Watanabe, B., Suzuki, S., Hiratake, J., Mano, J., Yazaki, K.: Characterization of raspberry ketone/zingerone synthase, catalyzing the alpha, beta-hydrogenation of phenylbutenones in raspberry fruits. Biochem. Biophys. Res. Commun. 412, 104–108 (2011)

    Article  CAS  Google Scholar 

  23. Meng, Z.B., Hu, Y.H., Kai, Y.M., Yang, W.G., Cao, Z., Shen, F.: Thermodynamics of solubility of thiomalic acid in different organic solvents from 278.15 K to 333.15 K. Fluid Phase Equilib. 352, 1–6 (2013)

    Article  CAS  Google Scholar 

  24. Moodley, K., Rarey, J., Ramjugernath, D.: Experimental solubility for betulin and estrone in various solvents within the temperature range T = (293.2 to 328.2) K. J. Chem. Thermodyn. 98, 42–50 (2016)

    Article  CAS  Google Scholar 

  25. Ha, E.S., Kim, J.S., Kuk, D.H., Ha, D.H., Baek, I.H., Kim, M.S.: Determination and correlation of solubility of Pranlukast hemihydrate in five organic solvents at different temperatures and its dissolution properties. J. Mol. Liq. 225, 231–234 (2017)

    Article  CAS  Google Scholar 

  26. Pawar, R.R., Aher, C.S., Pagar, J.D., Nikam, S.L., Hasan, M.: Solubility, density and solution thermodynamics of NaI in different pure solvents and binary mixtures. J. Chem. Eng. Data 57, 3563–3572 (2012)

    Article  CAS  Google Scholar 

  27. Tao, M.Y., Sun, H., Wang, Z., Cui, P.L., Wang, J.K.: Correlation of solubility of pioglitazone hydrochloride in different binary solvents. Fluid Phase Equilib. 352, 14–21 (2013)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The financial supports of the Tianjin Research Program of Application Foundation and Advanced Technology (No. 14JCZDJC40900), The Training Program for Changjiang Scholars and Innovative Research Team in University ([2013]373) and the Innovative Research Team of Tianjin Municipal Education Commission (TD12-5004) are gratefully acknowledged.

Author information

Authors and Affiliations

  1. Tianjin Key Laboratory of Marine Resources and Chemistry, College of Material Science and Chemical Engineering, Tianjin University of Science & Technology, Tianjin, 300457, People’s Republic of China

    Min Shu, Liang Zhu, Liyu Wang, Yanfei Wang, Libin Yang & Zuoliang Sha

  2. Tianjin Academy of Environmental Science, Tianjin, 300191, People’s Republic of China

    Min Yuan & Meng Zeng

Authors
  1. Min Shu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Liang Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Min Yuan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Liyu Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yanfei Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Libin Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Zuoliang Sha
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Meng Zeng
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Liang Zhu or Min Yuan.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shu, M., Zhu, L., Yuan, M. et al. Solubility and Solution Thermodynamic Properties of 4-(4-Hydroxyphenyl)-2-butanone (Raspberry Ketone) in Different Pure Solvents. J Solution Chem 46, 1995–2013 (2017). https://doi.org/10.1007/s10953-017-0681-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10953-017-0681-0

Keywords

Search

Navigation