Solubility of Fullerenes in Fatty Acids Esters: A New Way to Deliver In Vivo Fullerenes. Theoretical Calculations and Experimental Results

  • Franco Cataldo
Part of the Carbon Materials: Chemistry and Physics book series (CMCP, volume 1)


The biological effects of fullerenes and, in particular, of C60 have been recognized since long time. One of the problems which hindered the application of fullerenes in medicinal chemistry regards their insolubility in water and water-based fluids. In the present chapter it is reported that C60 and C70 fullerenes are soluble in vegetable oils, in general, in esters of fatty acids and in free fatty acids. These results pave the way in the utilization of vegetable oils as vehicles in the delivery of fullerenes for both topical applications and internal use (e.g., intramuscular injection).

It is shown that the solubility of fullerenes in vegetable oils can be predicted and justified on the basis of the solubility parameters of C60 and C70 and of the glycerol esters of fatty acids. A detailed procedure for the calculation of the solubility parameters of fullerenes and vegetable oils by group increment is reported.

The solubility of C60 and C70 in a series of vegetable oils, namely: olive, sunflower, peanut, soybean, linseed and castor oil, has been determined quantitatively spectrophotometrically. Additionally, the solubility of C60 and C70 has been determined quantitatively in the methyl esters of brassica oilseed and only qualitatively in molten cow butter, molten stearic acid and molten behenamide. The experimental results show that the solubility of fullerenes appears to be dependent on the unsaturation level of the fatty acids composing the vegetable oils being lower in oils with higher unsaturation level. The solubility has been found dependent also on the polarizability parameter of the vegetable oils.

The stability of C60 and C70 solutions in vegetable oils has been studied in air and under inert atmosphere, after thermal processing and under the action of UV radiation. In all cases it has been found that C60 and C70 are prone to form adducts with the fatty acid chains of the vegetable oils. The adducts are formed both by radical and Diels-Alder mechanisms. The pharmaceutical valency and potential of such adducts has also been discussed.


Adducts C60 C70 esters of fatty acid excipients fatty acids fullerenes glycerol esters of fatty acids grafting group increment method solubility solubility parameter vehicles for drug delivery vegetable oils triglycerides 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Adami E (1960) Pharmacology and Pharmacotherapy. Istituto Editoriale Cisalpino, Milan, p. 1124.Google Scholar
  2. Beck MT, Mandi G (1997) Solubility of C60. Fullerene Sci. Technol. 4:509-515.Google Scholar
  3. Beckhaus HD, Verevkin S, Ruchardt C, Diederich F, Thilgen C, ter Meer HU, Mohn H, Muller W (1994) C70 is more stable than C60: experimental determination of the heat of formation of C70. Angew. Chem. Int. Ed. Engl. 33:996-998.CrossRefGoogle Scholar
  4. Bicerano J (1996) Prediction of Polymer Properties, 2nd ed. Marcel Dekker, New York.Google Scholar
  5. Braun T, Mark L, Ohmacht R, Sharma U (2007) Olive oil as biocompatible solvent for pristine C60. Fullerenes Nanotechnol. Carbon Nanostruct. 15:311-314.CrossRefGoogle Scholar
  6. Braun T, Buvári-Barcza A, Barcza L, Konkoly-Thege I, Fodor M, Migali B (1994) Mechanochemistry: a novel approach to the synthesis of fullerene compounds. Water soluble Buckminster fullerene - gamma- cyclodextrin inclusion complexes via solid-solid reaction. Solid State Chem. 74:47-51.Google Scholar
  7. Catalan JS, Laynez JL, Jagerovic N, Elguero J (1995) The colors of C60 solutions. Angew. Chem. Int. Ed. Engl. 34:105-107.CrossRefGoogle Scholar
  8. Cataldo F, Braun T (2007) Solubility of C60 fullerene in long chain fatty acid esters. Fullerenes Nanot. Carbon Nanostruct. 15:331-339.CrossRefGoogle Scholar
  9. Cataldo F (2002) Encapsulation of C60 fullerene in γ-cyclodextrine. Polym. Degrad. Stabil. 77:111-120.CrossRefGoogle Scholar
  10. Dugan LL, Lovett E, Cuddihy S, Ma BW, Lin TS, Choi DW (2000) Carboxyfullerenes as neuroprotective antioxidants. Chapter 11 in Fullerenes: Chemistry, Physics and Technology, edited by Kadish K.M. and Ruoff, R.S. Wiley-Interscience, New York.Google Scholar
  11. Guanti G, Banfi L, Basso A, Riva R (2005) From natural to rationally designed artificial enediynes: towards new anticancer antibiotics activable at will. Chapter 19 in Polyynes: Synthesis, Properties and Applications, edited by Cataldo, F. Taylor & Francis/CRC Press, Boca Raton, FL.Google Scholar
  12. Hansen CM, Smith AL (2004) Using Hansen solubility parameters to correlate solubility of C60 fullerene in organic solvents and in polymers. Carbon 42:1591-1597.CrossRefGoogle Scholar
  13. Hansen CM (2007) Hansen Solubility Parameters: A User’s Handbook. CRC press/Taylor & Francis, Boca Raton, FL.Google Scholar
  14. Heymann D (1996a) Solubility of fullerenes C60 and C70 in seven n-alcohols and their deduced solubility in water. Fullerene Sci. Technol. 5:291-310.Google Scholar
  15. Heymann D (1996b) Solubility of C60 in alcohols and alkanes. Carbon 34:627-631.CrossRefGoogle Scholar
  16. Hildebrand JH, Scott RL (1950) The Solubility of Non-Electrolytes. Reinhold, New York.Google Scholar
  17. Huang JC (2005) Multiparameter solubility model of fullerene C60. Fluid Phase Equil. 237:186-192.CrossRefGoogle Scholar
  18. Korobov MV, Smith AL (2000) Solubility of the fullerenes. In: Kadish KM, Ruoff RS (eds.) Fullerenes: Chemistry, Physics and Technology. Wiley-Interscience, New York.Google Scholar
  19. Liu H, Tao G, Evans DG, Kou Y (2005) Solubility of C60 in ionic liquids. Carbon 43:1782-1785.CrossRefGoogle Scholar
  20. Makitra RG, Pristanskii RE, Flyunt RI (2003) Solvent effects on the solubility of C60 fullerene. Russ. J. General Chem. 73:1227-1232.CrossRefGoogle Scholar
  21. Marcus Y, Smith AL, Korobov MV, Mirakyan AL, Avramenko NV, Stukalin EB (2001) Solubility of C60 fullerene. J. Phys. Chem. B 105:2499-2506.CrossRefGoogle Scholar
  22. Martinenghi GB (1963) Tecnologia Chimica Industriale degli Oli Grassi e Derivati, 3rd ed. Ulrico Hoepli, Milan (in italian).Google Scholar
  23. Murthy CN, Geckeler KE (2001) Solubility correlation of C60 fullerene in different solvents. Fullerenes Nanotechnol. Carbon Nanostruct. 9:477-486.CrossRefGoogle Scholar
  24. Ruoff RS, Tse DS, Malhotra R, Lorents DC (1993) Solubility of C60 in a variety of solvents. J. Phys. Chem. 97:3379-3383.CrossRefGoogle Scholar
  25. Sayes CM, Gobin AM, Ausman KD, Mendez J, West JL, Colvin VL (2005) Nano-C60 cytotoxicity is due to lipid peroxidation. Biomaterials 26:7587-7595.CrossRefGoogle Scholar
  26. Sivaraman N, Dhamodaran R, Kaliappan I, Srinivasan TG, Vasudeva Rao PR, Mathews CK (1994) Solubility of C70 in organic solvents. Fullerene Sci. Technol. 2:233-246.Google Scholar
  27. Sivaraman N, Srinivasan TG, Vasudeva Rao PR, Natarajan R (2001) QSPR modelling for solubility of fullerene (C60) in organic solvents. J. Chem. Inf. Comput. Sci. 41:1067-1074.Google Scholar
  28. Tabata Y, Murakami Y, Ikada Y (1997) Antitumor effect of poly(ethylene glycol)-modified fullerene. Fullerene Sci. Technol. 5:989-1007.Google Scholar
  29. Taylor R (1999) Lecture Notes on Fullerene Chemistry. A Handbook for Chemists. Imperial College Press, London.Google Scholar
  30. Van Krevelen DW (1990) Properties of Polymers. Their correlation with chemical structure, their numerical estimation and prediction from additive group contributions, 3rd ed. Elsevier, Amsterdam.Google Scholar
  31. Wilson SR (2000) Biological aspects of fullerenes. Chapter 10 in Fullerenes: Chemistry, Physics and Technology, edited by Kadish K.M. and Ruoff, R.S. Wiley-Interscience, New York.Google Scholar

Copyright information

© Springer Science + Business Media B.V 2008

Authors and Affiliations

  • Franco Cataldo
    • 1
    • 2
  1. 1.Tor Vergata UniversityRomeItaly
  2. 2.Actinium Chemical ResearchRomeItaly

Personalised recommendations