Synthesis, chemical characterization, and economical feasibility of poly-phenolic-branched-chain fatty acids: Synthesis of poly-phenolic-branched-chain fatty acids

Authors: Ngo, Helen; Wagner, Karen; YAN, ZONGCHENG - South China University Of Technology; Nunez, Alberto; Yee, Winnie; Fan, Xuetong; Moreau, Robert

Submitted to: European Journal of Lipid Science and Technology
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 12/6/2016
Publication Date: 1/1/2017
Publication URL: http://handle.nal.usda.gov/10113/5700737
Citation: Lew, H.N., Wagner, K., Yan, Z., Nunez, A., Yee, W.C., Fan, X., Moreau, R.A. 2017. Synthesis, chemical characterization, and economical feasibility of poly-phenolic-branched-chain fatty acids: Synthesis of poly-phenolic-branched-chain fatty acids. European Journal of Lipid Science and Technology. doi: 10.1002/ejit.201600380.

Interpretive Summary: Listeria monocytogenes is a common foodborne pathogen which can cause disease in humans. It is also one of the most virulent foodborne pathogens with a mortality rate of 20 to 30%. The continued outbreaks of L. monocytogenes in foods imply that current antimicrobial products are not sufficient to control pathogen contamination. Thus, ARS scientists aim to develop novel antimicrobials with hydrophobic and hydrophilic properties from natural phenolic compounds and vegetable oils. This paper describes the discovery of the hybrid molecules that result by conjugating these electron-rich aromatic rings (phenol) to soybean fatty acids. The results show that a highly efficient ARS arylation process has been developed to make these phenolic branched-chain fatty acid products. These products are found to bear close resemblance to antimicrobial compounds that are receiving a great deal of attention for biomedical and/or materials applications. To the best of our knowledge, our own work in this area is the only such example of producing these phenolic branched-chain fatty acid products efficiently. This finding is highly encouraging because the phenolic products are odorless which should make them appealing for possible food applications to kill the harmful Listeria monocytogenes.

Technical Abstract: New poly-phenolic branched-chain fatty acid (poly-PBC-FA) products were synthesized from a combination of soybean fatty acids and phenolic materials through a highly efficient zeolite catalyzed arylation method. These poly-PBC-FAs are liquid at room temperature and do not have the unpleasant odor like the parent phenol reagent. They were found to be comprised of various numbers of phenol rings on the fatty acid chain, and this is important because compounds with a higher number of hydroxyl groups are expected to have better antimicrobial activities. Detailed characterization using gas chromatography and high performance liquid chromatography coupled to a quadrupole-time of flight mass spectrometer techniques were used to measure the number of phenol groups on the alkyl fatty acid chains. A cost process modeling technique was used to determine the economic feasibility of this arylation process to make these important poly-PBC-FA products.