Design and synthesis of 1,3-dicapryloyl-2-acetylglycerol as molecular probe for triacylglycerol metabolism study

Authors

  • Qiong Lei,

    Corresponding author
    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore
    • Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore Fax: (65) 6791 1961
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  • Wilson Liangwei Lee,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore
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  • Tianhu Li

    Corresponding author
    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore
    • Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore Fax: (65) 6791 1961
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Abstract

The increasing number of health issues caused by obesity and lack of healthy and efficient fat substitutes require development on new fat substitute. This study proposes a new potential reduced-calorie structured triacylglycerol (TAG) of “1,3-medium-chain, 2-short-chain triglycerides (MSM)” configuration, and the fat substitution method is based on the suppression of 2-monoacylglycerol absorption into intestinal cells, which would decrease the recombination of TAG and reduce lipid absorption in the digestive tract. A molecular probe, 1,3-dicapryloyl-2-acetylglycerol, is offered for nutritionists to conduct further study on its metabolism in human body. The synthesis method for this structured TAG starts from the lipase-catalyzed esterification between glycerol and caprylic acid, yielding 1,3-dicapryloylglycerol, and is followed by direct esterification with acetic anhydride to form 1,3-dicapryloyl-2-acetylglycerol. Its structure is characterized by FTIR,1H NMR,13C NMR, and LC-ESI-MS.

Practical application: This kind of pure structured triglyceride can function as a molecular probe for nutritionists to test its metabolism in human body and conduct further evaluation on their fat substitute potential. The synthesis method can also be easily adopted by food industry since it involves only two simple reaction steps.

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