Catalytic synthesis and characterization of phenol‐branched‐chain fatty acid isomers*

Ngo, Helen L.; Fox, Pamela S.; Núñez, Alberto; Moreau, Robert A.; Haas, Michael J.

doi:10.1002/ejlt.201300227

Cited by 10 publications

(15 citation statements)

References 15 publications

(17 reference statements)

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“…The yield of the dimer phenolic product with these detectors was consistent with the obtained with the mass spectrometer (between 4 and 6%). This result is also consistent with the previously published study of the phenol products of OLA, where a similar dimer was identified [10]. This finding is important because we can utilize these dimer products for future antimicrobial studies.…”

Section: Analysis Of Pbc-fas Derived From These Arylation Reactionssupporting

confidence: 92%

“…The MS/MS spectra of phenol products (monomers and dimers, spectra not shown) have a common fragment ion at m/z 107.05 (see fragment ion in Fig. 2B), similar to the one observed in the GC-MS analysis as reported previously [10]. Using a collision energy of 15 eV, the intensity of this ion is enhanced, allowing the plotting of the extracted ion chromatogram at m/z 107 as it is shown in Fig.…”

Section: Analysis Of Pbc-fas Derived From These Arylation Reactionssupporting

confidence: 79%

“…Previously, we reported a catalytic process to produce mono-phenolic branched chain fatty acids from oleic acid [10]. In the current study, poly-phenolic branched-chain fatty acid products were successfully synthesized for the first time and thoroughly characterized by mass spectroscopy.…”

Section: Discussionmentioning

confidence: 94%

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

Ngo

Wagner

Yan

et al. 2017

Euro J Lipid Sci & Tech

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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. Practical applications: The continued outbreaks of Listeria monocytogenes in foods imply that current antimicrobial products are not sufficient to control pathogen contamination. These new phenolic branched‐chain fatty acid products contain hydrophobic and hydrophilic properties. They are found to bear close resemblance to antimicrobial compounds that are receiving a great deal of attention for biomedical and/or materials applications. 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. New poly‐phenolic branched‐chain fatty acid products were synthesized from a combination of soybean fatty acids and phenol materials through a highly efficient zeolite catalyzed arylation method. These isolated phenolic fatty acid materials are liquid at room temperature and do not have the unpleasant odor like the parent phenol reagent. Mass spectroscopy results confirmed more than one phenol group is on the alkyl chain due to the polyunsaturated fatty acid materials used. The cost model indicated that the process is feasible at the industrial scale.

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Section: Analysis Of Pbc-fas Derived From These Arylation Reactionssupporting

confidence: 92%

Section: Analysis Of Pbc-fas Derived From These Arylation Reactionssupporting

confidence: 79%

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

Ngo

Wagner

Yan

et al. 2017

Euro J Lipid Sci & Tech

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“…Our group has also developed a highly efficient one‐step arylation reaction to form a covalently bound phenol‐oleic branched‐chain fatty acid product (PBC‐FA, Fig. c), which was composed of a hydrophobic aliphatic long chain with the hydrophilic phenolic group (Ngo et al, ). The compound was generated through the formation of the covalent carbon–carbon bond using highly refined oleic acid (fatty acid with one double bond on the alkyl chain) and phenol (aromatic group with one hydroxy group on the ring).…”

Section: Introductionmentioning

confidence: 99%

“…Although this product has the same phenol component as the free phenol itself, it does not have the same physical properties. While free phenol is solid at room temperature and has a very unpleasant odor, the PBC‐FA is liquid at room temperature, is not volatile, and has absolutely no odor (Ngo et al, ). Interestingly, this PBC‐FA product was found to be potent against a number of Gram‐positive bacteria with minimum inhibitory concentrations (MIC) of 1.8–3.6 μg mL −1 (Fan et al, ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anti‐Listeria Properties of Odorless Hybrid Bio‐Based n‐Phenolic Vegetable Branched‐Chain Fatty Acids

Ngo

Wagner

Yan

et al. 2019

J Americ Oil Chem Soc

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Consumers are becoming concerned about the impact of synthetic chemicals on human health and environments, and demanding natural compounds to reduce risk of antibiotic resistance of microorganisms. However, natural compounds are often less effective than synthetic antimicrobials. This challenge may be addressed with the development of bio-based antimicrobial agents. In this study, bio-based n-phenolic branched-chain fatty acids (n-phenolic-branched chain fatty acid [BCFA]) were synthesized from vegetable oil (soybean and safflower) fatty acids and four natural phenolics (phenol, thymol, carvacrol, and creosote), and tested against Listeria innocua. Results revealed that the newly synthesized products in crude form had minimum inhibitory concentrations (MIC) against L. innocua ranging from 3.6 to 116.4 μg mL −1 , with phenol-BCFA products having the lowest MIC (3.6 μg mL −1 ) and minimum bactericidal concentration (MBC) (7.3 μg mL −1 ). The precursors (unsaturated free fatty acids and phenolics) and noncovalently bound mixture of free fatty acids and phenolics had MIC above 232.7 μg mL −1 . After purification by molecular fractionation, n-phenolic-BCFA in the free fatty acid/monomer form were shown to be responsible for the anti-Listeria activity with MIC of 3.6-7.3 μg mL −1 and MBC of 7.3-29.1 μg mL −1 . These promising results pave the road for further study of this new class of bio-based compounds, which may lead to their widespread use.

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Bio-based phenolic branched-chain fatty acid in wash water reduced populations of Listeria innocua on apple fruit

Ryu,

Chuesiang,

Uknalis

et al. 2024

Heliyon

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Catalytic synthesis and characterization of phenol‐branched‐chain fatty acid isomers*

Cited by 10 publications

References 15 publications

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

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

Synthesis and Anti‐Listeria Properties of Odorless Hybrid Bio‐Based n‐Phenolic Vegetable Branched‐Chain Fatty Acids

Bio-based phenolic branched-chain fatty acid in wash water reduced populations of Listeria innocua on apple fruit

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