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Solubilization Behavior of Phorbol Esters from Jatropha Oil in Surfactant Micellar Solutions

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Journal of Surfactants and Detergents

Abstract

Phorbol esters (PEs) are important toxic compounds found in Jatropha curcas oil and pressed seeds. These compounds are tumor promoters; thus, their removal prior to further utilization of the pressed seed is important. This work aimed to investigate the solubilization behavior of PEs and Jatropha oil in nonionic [effect of the ethylene oxide number (EON), carbon-chain length and temperature] and anionic (NaCl addition) surfactant systems. The results reveal that an increase in the EON of the nonionic surfactant molecules, rather than an increase in the carbon-chain length, enhances PE solubilization. The hydrophile-lipophile balance (HLB) value was correlated with PE solubilization for nonionic surfactant solutions. The solubilization of PEs decreased slightly with increasing temperature, in contrast to solubilization of the oil. Moreover, the mole fraction of PE solubilized in the micelle decreased with increasing electrolyte concentration in anionic surfactant solutions. The solubilization behavior of PEs in both nonionic and anionic solutions indicates that PE acts more like a polar compound than a nonpolar compound. In addition, the PEs in nonionic micelles are likely located in the palisade region (i.e., between the head group and the first few carbon atoms of the tail), whereas those in anionic micelles are likely near the outer core of the head group. This finding suggests that a nonionic surfactant with a higher EON has a greater potential to extract PE from Jatropha seeds. If an anionic surfactant is combined as co-surfactant, a small amount of electrolyte should be added to increase PE solubilization.

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Acknowledgments

We would like to express gratitude to the Graduate School of Chulalongkorn University for the Chulalongkorn University Graduate Scholarship to commemorate the 72nd Anniversary of His Majesty King Bhumibol Adulyadej and the 90th Anniversary of Chulalongkorn University Fund (Ratchadaphiseksomphot Endowment Fund). We would also like to thank the Center of Excellence on Hazardous Substance Management (HSM) for supporting the scholarship and providing research funding during the study.

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Authors and Affiliations

  1. International Program in Hazardous Substance and Environmental Management, Graduate School, Chulalongkorn University, Bangkok, 10330, Thailand

    Naphatsarnan Phasukarratchai

  2. Center of Excellence for Hazardous Substance Management (HSM), Chulalongkorn University, Bangkok, 10330, Thailand

    Naphatsarnan Phasukarratchai & Chantra Tongcumpou

  3. Environmental Research Institute, Chulalongkorn University, Pathumwan, Bangkok, 10330, Thailand

    Seelawut Damrongsiri & Chantra Tongcumpou

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  1. Naphatsarnan Phasukarratchai
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  2. Seelawut Damrongsiri
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  3. Chantra Tongcumpou
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Correspondence to Chantra Tongcumpou.

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Phasukarratchai, N., Damrongsiri, S. & Tongcumpou, C. Solubilization Behavior of Phorbol Esters from Jatropha Oil in Surfactant Micellar Solutions. J Surfact Deterg 19, 29–37 (2016). https://doi.org/10.1007/s11743-015-1758-7

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  • DOI: https://doi.org/10.1007/s11743-015-1758-7

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