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1,3-Diferuloyl-sn-glycerol from the biocatalytic transesterification of ethyl 4-hydroxy-3-methoxy cinnamic acid (ethyl ferulate) and soybean oil

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Abstract

1,3-Diferuloyl-sn-glycerol is found ubiquitously throughout the plant kingdom, possessing ultraviolet adsorbing and antioxidant properties. Diferuloyl glycerol was synthesized and isolated as a byproduct in up to 5% yield from a pilot plant scale packed-bed, biocatalytic transesterification of ethyl ferulate with soybean oil or mono- and diacylglycerols from soybean oil. The yield of the diferuloyl glycerol byproduct was directly proportional to the overall water concentration of the bioreactor. The isolated diferuloyl glycerol exhibited good ultraviolet adsorbing properties, 280–360 nm with a λmax 322 nm, and compared well to the efficacy of commercial sunscreen active ingredients. The antioxidant capacity of diferuloyl glycerol (0.25–2.5 mM) was determined by its ability to scavenge 2,2-diphenyl-1-picrylhydrazyl radicals and was comparable to that of ferulic acid. At current pilot plant scale production capacity, 120 kg diferuloyl glycerol byproduct could be isolated per year.

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Acknowledgements

The authors thank Steven Grall (Grall Co., iSoy Technologies Corp.) for development and implementation of the pilot plant scale backed-bed bioreactor used for the feruloyl soy glycerol production. Additionally, the authors thank Judy Blackburn, Leslie Smith, Nathan Applegren, and Emily Carlson for their excellent technical assistance and Karl Vermillion for obtaining all NMR spectra.

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Authors and Affiliations

  1. New Crops and Processing Technology Research Unit, Agricultural Research Service, National Center for Agricultural Utilization Research, U.S. Department of Agriculture, 1815 N. University St., Peoria, IL, 61604, USA

    David L. Compton & Joseph A. Laszlo

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  1. David L. Compton
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  2. Joseph A. Laszlo
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Correspondence to David L. Compton.

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Product names are necessary to report factually on available data; however, the USDA neither guarantees nor warrants the standard of the product, and the use of the name by the USDA implies no approval of the product to the exclusion of others that may be suitable.

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Compton, D.L., Laszlo, J.A. 1,3-Diferuloyl-sn-glycerol from the biocatalytic transesterification of ethyl 4-hydroxy-3-methoxy cinnamic acid (ethyl ferulate) and soybean oil. Biotechnol Lett 31, 889–896 (2009). https://doi.org/10.1007/s10529-009-9952-1

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  • DOI: https://doi.org/10.1007/s10529-009-9952-1

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