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Purification of ethyl docosahexaenoate by selective alcoholysis of fatty acid ethyl esters with immobilized Rhizomucor miehei lipase

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Journal of the American Oil Chemists' Society

Abstract

Ethyl docosahexaenoate (E-DHA) is efficiently enriched by the selective alcoholysis of ethyl esters originating from tuna oil with lauryl alcohol using immobilized lipase. Alcoholysis of ethyl esters by immobilized Rhizopus delemar lipase raised the E-DHA content in the unreacted ethyl ester fraction from 23 to 49 mol% in 90% yield. However, the content of ethyl eicosapentaenoate (E-EPA) was higher than the initial content. Hence we attempted to screen for a suitable lipase to decrease the E-EPA content, and chose Rhizomucor miehei lipase. Several factors affecting the alcoholysis of ethyl esters were investigated, and the reaction conditions were determined. When alcoholysis was performed at 30°C with shaking in a mixture containing ethyl esters/lauryl alcohol (1:3, mol/mol) and 4 wt% of the immobilized R. miehei lipase, the E-DHA content in the ethyl ester fraction was increased and the E-EPA content was decreased. By alcoholyzing ethyl esters in which the E-DHA content was 45 mol% (E-tuna-45) for 26 h, the E-DHA content was increased to 74 mol% in 71% yield and the E-EPA content was decreased from 12 to 6.2 mol%. To investigate the stability of the immobilized lipase, batch reactions were carried out continually by replacing the reaction mixture with fresh E-tuna-45/lauryl alcohol (1:3, mol/mol) every 24 h. The decrease in the alcoholysis extent was only 17% even after 100 cycles of reaction. It was found that increasing the proportion of lauryl alcohol increased the conversion of E-EPA to lauryl-EPA. When an ethyl ester mixture in which the E-DHA content was 60 mol% (E-tuna-60) was alcoholyzed for 24 h with 7 molar equivalents of lauryl alcohol, the E-DHA content was raised to 93 mol% with 74% yield and the E-EPA content was reduced from 8.6 to 2.9 mol%.

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Authors and Affiliations

  1. Osaka Municipal Technical Research Institute, 1-6-50 Morinomiya, Joto-ku, 536-8553, Osaka, Japan

    Yuji Shimada, Akio Sugihara & Yoshio Tominaga

  2. Maruha Corporation, 300-4295, Ibaraki, Japan

    Kazuaki Maruyama, Takashi Baba & Shigeru Moriyama

  3. Department of Agricultural Chemistry, School of Agriculture, Kinki University, 631-8505, Nara, Japan

    Sadao Komemushi

Authors
  1. Yuji Shimada
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  2. Kazuaki Maruyama
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  3. Akio Sugihara
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  4. Takashi Baba
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  5. Sadao Komemushi
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  6. Shigeru Moriyama
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  7. Yoshio Tominaga
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Correspondence to Yuji Shimada.

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Shimada, Y., Maruyama, K., Sugihara, A. et al. Purification of ethyl docosahexaenoate by selective alcoholysis of fatty acid ethyl esters with immobilized Rhizomucor miehei lipase. J Amer Oil Chem Soc 75, 1565–1571 (1998). https://doi.org/10.1007/s11746-998-0095-7

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  • DOI: https://doi.org/10.1007/s11746-998-0095-7

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