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Selective Synthesis of Diacylglycerols of Conjugated Linoleic Acid

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Journal of the American Oil Chemists' Society

Abstract

Quasi-quantitative selective production of diacylglycerols (DAG) rich in polyunsaturated fatty acids (PUFA) was demonstrated using a Penicillium camembertii lipase. Under optimal initial conditions [60 °C, 10% (w/w) biocatalyst based on total reactants, 5:1 molar ratio of free conjugated linoleic acid (CLA) to hydroxyl groups in partial glycerides consisting of ca. 90% (w/w) monoacylglycerols (MAG) and ca. 10% (w/w) diacylglycerols (DAG)], reaction for only 4.5 h gave 98.62% DAG and 1.38% MAG. The DAG contained >95% unsaturated fatty acid residues. Predominant DAG were LnLn, LnL and LL, although LO and LP were also significant (Ln = linolenic; L = linoleic; O = oleic; P = palmitic). Effects of the acylating agent (free CLA), solvent, and temperature on undesirable side reactions were determined. Reaction selectivities were similar in n-hexane and solvent-free media. The re-esterified products contained less than 7% saturated fatty acids and a higher ratio of unsaturated to saturated fatty acid residues (19.00) than the precursor soybean oil (5.22). The biocatalyst retained 55% of its initial activity after use in three consecutive reaction/extraction cycles.

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Acknowledgments

This work was supported by the Spanish CICYT (MAT2007-6666-C02-02). A predoctoral fellowship for E. Hernández-Martín was provided by the Spanish Research Council, CSIC.

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Authors and Affiliations

  1. Departamento de Biocatálisis, Instituto de Catálisis y Petroleoquímica, CSIC, C/Marie Curie 2, Cantoblanco, 28049, Madrid, Spain

    Estela Hernández-Martín & Cristina Otero

  2. Department of Chemical and Biological Engineering, University of Wisconsin, Madison, WI, 53706-1691, USA

    Charles G. Hill Jr

Authors
  1. Estela Hernández-Martín
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  2. Charles G. Hill Jr
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  3. Cristina Otero
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Correspondence to Cristina Otero.

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Hernández-Martín, E., Hill, C.G. & Otero, C. Selective Synthesis of Diacylglycerols of Conjugated Linoleic Acid. J Am Oil Chem Soc 86, 427–435 (2009). https://doi.org/10.1007/s11746-009-1372-9

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  • DOI: https://doi.org/10.1007/s11746-009-1372-9

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