NMR properties of conjugated linoleic acid (CLA) methyl ester hydroperoxides

Pajunen, Taina I.; Koskela, Harri; Hase, Tapio; Hopia, Anu

doi:10.1016/j.chemphyslip.2008.05.001

Cited by 20 publications

(21 citation statements)

References 36 publications

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“…As shown in Figure , new compounds were formed in the 1 H NMR spectral region between 5.45 and 6.60 ppm from oxidation of linoleic acyl group and these were assigned to ( Z,E ) and ( E,E ) conjugated dienic systems in chains with hydroperoxy groups. Furthermore, these assignments agreed with the findings of previous studies (Neff and others ; Pajunen and others ; Guillén and Goicoechea ; Goicoechea and Guillén ; Wang and others ). The 4 protons of the ( Z,E ) conjugated dienic system generated 4 different multiplets located near 5.55, 6.55, 6.00, and 5.50 ppm, whereas the 4 multiplets of the ( E,E ) conjugated dienic system were at 5.75, 6.25, 6.05, and 5.45 ppm.…”

Section: Resultssupporting

confidence: 92%

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Antioxidant Properties of Caffeic acid Phenethyl Ester and 4‐Vinylcatechol in Stripped Soybean Oil

Jia

Wang

et al. 2015

Journal of Food Science

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Caffeic acid was used to synthesize 4-vinylcatechol (4-VC) by thermal decarboxylation and to prepare caffeic acid phenethyl ester (CAPE) by esterification reaction. The identities of synthesized products were confirmed by (1)H NMR. Antioxidative activities of 4-VC and CAPE were compared with α-tocopherol and BHT in stripped soybean oil at 60 °C under the dark. To evaluate the degrees of oxidation at different concentrations and combinations, peroxide value (PV) and (1)H NMR were performed. From the results of PV, the formation of primary oxidation products (i.e., hydroperoxides) in stripped soybean oil containing 200 ppm CAPE was the slowest. The relative oxidation degree of 200 ppm CAPE (9.5%) was lower than other samples on 9 d. Similar results were obtained by (1)H NMR analysis. After 15 d of storage, levels of conjugated diene forms and aldehydes of 200 ppm CAPE sample (57.3 and 0.9 mmol/mol oil) were also lower than other treatments. In addition, 4-VC and α-tocopherol were found to have a synergistic antioxidant effect.

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Section: Resultssupporting

confidence: 92%

“…These assignments agreed with the Ref. (Neff and others ; Pajunen and others ; Goicoechea and others ; Wang and others ).…”

Section: Resultssupporting

confidence: 89%

Antioxidant Properties of Caffeic acid Phenethyl Ester and 4‐Vinylcatechol in Stripped Soybean Oil

Jia

Wang

et al. 2015

Journal of Food Science

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“…Figure illustrates the structures and 13 C NMR data of the four major isomeric hydroperoxides of methyl linoleate. Table S1 presents a comparison of the 13 C NMR data of the present work with the literature data for isolated hydroxyperoxides and hydroperoxides . The agreement of the present 13 C NMR data with those of isolated hydroperoxides is excellent.…”

Section: Resultsmentioning

confidence: 99%

¹H–¹³C HMBC NMR experiments as a structural and analytical tool for the characterization of elusive trans/cis hydroperoxide isomers from oxidized unsaturated fatty acids in solution

Ahmed

Siddiqui

Choudhary

et al. 2019

Magnetic Reson in Chemistry

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The radical‐dependent oxidation of unsaturated fatty acids is a fundamental reaction in lipid chemistry, biochemistry, and technology. We report herein the first successful application of 1H–13C HMBC NMR experiment for the identification and quantification of complex and minor (3.9% to 0.85%) components of cis and trans primary hydroperoxide isomers of oxidized oleate and linoleate methyl esters in solution, without the need of laborious isolation of the individual components.

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“…Some of the protons of these compounds give signals in the 1 H NMR spectra that do not overlap with those of acyl groups, thus making their identification and also their quantification possible. The identification of these signals has been based on previous studies carried out with standard compounds (Neff and others ; Frankel and others, ; Porter and others ; Neff and El‐Agaimy ; Kuklev and others ; Jie and Lam ; Lin and others ; Pajunen and others ). Table gives the chemical shifts of the signals of the protons of the above‐mentioned primary oxidation compounds.…”

Section: H Nmr As a Tool For The Study Of Food Lipid Thermo‐oxidatiomentioning

confidence: 99%

A Review of Thermo‐Oxidative Degradation of Food Lipids Studied by ¹H NMR Spectroscopy: Influence of Degradative Conditions and Food Lipid Nature

Martínez‐Yusta

Goicoechea

Guillén

2014

Comp Rev Food Sci Food Safe

145

153

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This review summarizes present-day knowledge provided by proton nuclear magnetic resonance ( 1 H NMR) concerning food lipid thermo-oxidative degradation. The food lipids considered include edible oils and fats of animal and vegetable origin. The thermo-oxidation processes of food lipids of very different composition, occurring at low, intermediate, or high temperatures, with different food lipid surfaces exposed to oxygen, are reviewed. Mention is made of the influence of both food lipid nature and degradative conditions on the thermo-oxidation process. Interest is focused not only on the evolution of the compounds that degrade, but also on the intermediate or primary oxidation compounds formed, as well as on the secondary ones, from both qualitative and quantitative points of view. Very valuable qualitative and quantitative information is provided by 1 H NMR, which can be useful for metabolomic and lipidomic studies. The chemical shift assignments of spectral signals of protons of primary (hydroperoxides and hydroxides associated with conjugated dienes) and secondary, or further (aldehydes, epoxides, among which 9,10-epoxy-12-octadecenoate [leukotoxin] can be cited, alcohols, ketones) oxidation compounds is summarized. It is worth noting the ability of 1 H NMR to detect toxic oxygenated α,β-unsaturated aldehydes, like 4-hydroperoxy-, 4,5-epoxy-, and 4-hydroxy-2-alkenals, which can be generated in the degradation of food lipids having omega-3 and omega-6 polyunsaturated groups in both biological systems and foodstuffs. They are considered as genotoxic and cytotoxic, and are potential causative agents of cancer, atherosclerosis, and Parkinson's and Alzheimer's diseases.

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NMR properties of conjugated linoleic acid (CLA) methyl ester hydroperoxides

Cited by 20 publications

References 36 publications

Antioxidant Properties of Caffeic acid Phenethyl Ester and 4‐Vinylcatechol in Stripped Soybean Oil

Antioxidant Properties of Caffeic acid Phenethyl Ester and 4‐Vinylcatechol in Stripped Soybean Oil

¹H–¹³C HMBC NMR experiments as a structural and analytical tool for the characterization of elusive trans/cis hydroperoxide isomers from oxidized unsaturated fatty acids in solution

A Review of Thermo‐Oxidative Degradation of Food Lipids Studied by ¹H NMR Spectroscopy: Influence of Degradative Conditions and Food Lipid Nature

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NMR properties of conjugated linoleic acid (CLA) methyl ester hydroperoxides

Cited by 20 publications

References 36 publications

Antioxidant Properties of Caffeic acid Phenethyl Ester and 4‐Vinylcatechol in Stripped Soybean Oil

Antioxidant Properties of Caffeic acid Phenethyl Ester and 4‐Vinylcatechol in Stripped Soybean Oil

1H–13C HMBC NMR experiments as a structural and analytical tool for the characterization of elusive trans/cis hydroperoxide isomers from oxidized unsaturated fatty acids in solution

A Review of Thermo‐Oxidative Degradation of Food Lipids Studied by 1H NMR Spectroscopy: Influence of Degradative Conditions and Food Lipid Nature

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Product

Resources

About

¹H–¹³C HMBC NMR experiments as a structural and analytical tool for the characterization of elusive trans/cis hydroperoxide isomers from oxidized unsaturated fatty acids in solution

A Review of Thermo‐Oxidative Degradation of Food Lipids Studied by ¹H NMR Spectroscopy: Influence of Degradative Conditions and Food Lipid Nature