Acid-promoted reactions of ethyl linoleate with nitrite ions: formation and structural characterization of isomeric nitroalkene, nitrohydroxy, and novel 3-nitro-1,5-hexadiene and 1,5-dinitro-1, 3-pentadiene products.

doi:10.1021/JO000090Q

Paper

Acid-promoted reactions of ethyl linoleate with nitrite ions: formation and structural characterization of isomeric nitroalkene, nitrohydroxy, and novel 3-nitro-1,5-hexadiene and 1,5-dinitro-1, 3-pentadiene products.

Published Aug 11, 2000 · A. Napolitano, E. Camera, M. Picardo

The Journal of organic chemistry

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51

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Abstract

The reaction of ethyl linoleate (1) with NO(2)(-) in different air-equilibrated acidic media resulted in the formation of complex patterns of products, some of which could be isolated by repeated TLC fractionation and were formulated as the nitroalkenes 2-5, the novel (1E, 5Z)-3-nitro-1,5-hexadienes 6/7, the novel (E,E)-1, 5-dinitro-1,3-pentadiene derivatives 8 and 9, and the nitro alcohols 10/11 and 12/13 by extensive GC-MS and 2D NMR analysis, as aided by 1D Hartmann-Hahn proton mapping experiments. Similar reaction of methyl oleate gave mainly nitroalkene (14/15) and allylic nitro derivatives (16/17). Formation of 2-13 may be envisaged in terms of HNO(2)-mediated nitration pathways in which regioisomeric beta-nitroalkyl radical intermediates derived from attack of NO(2) to the 1,4-pentadiene moiety of 1 evolve through competitive H-atom abstraction and free radical combination routes.

Study Snapshot

Acid-promoted reactions of ethyl linoleate with nitrite ions result in complex formation of isomeric nitroalkenes, nitrohydroxy, and novel 3-nitro-1,5-hexadienes and 1,5-dinitro-1,3-pent

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Acid-promoted reactions of ethyl linoleate with nitrite ions: formation and structural characterization of isomeric nitroalkene, nitrohydroxy, and novel 3-nitro-1,5-hexadiene and 1,5-dinitro-1, 3-pentadiene products.

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References

Citations

The Octadecanoids: Synthesis and Bioactivity of 18-Carbon Oxygenated Fatty Acids in Mammals, Bacteria, and Fungi

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Nitro Fatty Acids (NO2-FAs): An Emerging Class of Bioactive Fatty Acids

NO2-FAs show potential as a therapeutic agent against various diseases due to their ability to inhibit NF-B and activate Nrf2, promoting antioxidant signaling pathways.

Endogenous generation of nitro-fatty acid hybrids having dual nitrate ester (RONO2) and nitroalkene (RNO2) substituents

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Discovery of bioactive nitrated lipids and nitro-lipid-protein adducts using mass spectrometry-based approaches

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The discovery of nitro-fatty acids as products of metabolic and inflammatory reactions and mediators of adaptive cell signaling.

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