13C NMR spectroscopy for determining the acylglycerol positional composition of lampante olive oils. Chemical shift assignments and their dependence on sample concentration

Vlahov, Giovanna; Giuliani, Angela; Re, Paolo Del

doi:10.1039/c0ay00028k

Cited by 25 publications

(24 citation statements)

References 28 publications

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“…Table compares the chemical shifts of soybean oil with those of HMMS. The chains esterified at the sn ‐2 position are 0.4 ppm lower in chemical shift compared to those esterified at the sn ‐1,3 positions in both soybean and HMMS oils, a finding that is in agreement with other studies conducted on diacylglycerol‐enriched (DAG) oil and lampante olive oil (Hatzakis et al, ; Vlahov et al, ). In each position, the highest shift belongs to SFA, while the lower frequency is related to the linoleic acid (LO) and linolenic acid (LN) chains (Table ).…”

Section: Resultssupporting

confidence: 90%

“…These data provide information on FA composition of HMMS and the different positions of the esterified chains. The 13 C NMR spectrum of the carbonyl carbons of different oils was used to identify the acyl positional distribution ( sn ‐1,3 vs sn ‐2) of the SFA and UFA groups (Gouk et al, ) and also to provide information on the length and unsaturation pattern of the FA (Vlahov et al, ).…”

Section: Resultsmentioning

confidence: 99%

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Nuclear Magnetic Resonance Spectroscopy: A Versatile Tool for Qualitative and Quantitative Analysis of an Emulsifier Mixture of Soybean Oil

Vafaei

Marat

Eskin

et al. 2019

J Americ Oil Chem Soc

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Finding a fast, reliable, and reproducible approach for an accurate analysis of complex lipid mixtures of emulsifiers is crucial for the food and beverages, pharmaceuticals, personal care products, cosmetics, and agrochemicals industries. In the current study, a comprehensive qualitative and quantitative nuclear magnetic resonance (NMR) spectroscopy analysis of a high monoester mixture of soybean oil (HMMS) was conducted using 1 H, 13 C, and 31 P NMR of 2-chloro-4,-4,5,5-tetramethyl-1,3,2-dioxaphospholane (CTDP) derivatives. The HMMS was produced by enzymatic alcoholysis of soybean oil and 1.2-propanediol in a supercritical CO 2 system. Compositional distribution analysis, quantified by aliphatic carbons with 13 C NMR, showed that HMMS is composed of more unsaturated fatty acids, comprised of polyunsaturated fatty acids (PUFA) (60 AE 1.1%) and monounsaturated fatty acids (MUFA) (22 AE 0.8%), than saturated fatty acids (18 AE 0.9%). The 31 P NMR quantification of HMMS demonstrated that, out of the total amount of monoacylglycerols (MAG), they are composed of 21 AE 2.9% of 2-MAG and 4 AE 0.3% of 1-MAG. Among the three techniques, 31 P NMR spectroscopy proved to be a practical methodology with high reproducibility for the precise detection and quantification of partially esterified glycerols and free fatty acids in complex lipid mixtures.Keywords 1 H NMR Á 13 C NMR Á 31 P NMR Á Enzymatic alcoholysis Á Propylene glycol monoester Á Monoacylglycerols J Am Oil Chem Soc (2020) 97: 125-133.Supporting information Additional supporting information may be found online in the Supporting Information section at the end of the article.

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Section: Resultssupporting

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Nuclear Magnetic Resonance Spectroscopy: A Versatile Tool for Qualitative and Quantitative Analysis of an Emulsifier Mixture of Soybean Oil

Vafaei

Marat

Eskin

et al. 2019

J Americ Oil Chem Soc

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“…5a illustrates for the first time cross-peaks which correlate the protons of the glycerol segment with the carboxyl carbons of the attached fatty acid chains. Earlier assignments of these carbon signals for vegetable oils were explained by taking into consideration the double bonds inductive effect on the carbonyl groups [8,33] . The second and third cluster involves two sets of signals at low and high frequencies (Fig.…”

Section: C-nmr Spectramentioning

confidence: 99%

“…Two NMR techniques were to be compared regarding the quantification of fatty acids. Acids concentration using 31 C NMR could be obtained by integration of the appropriate carbonyl and olefinic signals (Table 2) [8,29,33,35,40]. In 1 H NMR, most of the signals are assigned to nonequivalent groups of protons that are common to fatty acyl chains.…”

Section: C-nmr Spectramentioning

confidence: 99%

High‐Resolution NMR Spectroscopy: An Alternative Fast Tool for Qualitative and Quantitative Analysis of Diacylglycerol (DAG) Oil

Hatzakis

Agiomyrgianaki

Kostidis

et al. 2011

J Americ Oil Chem Soc

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Multinuclear ( 1 H, 13 C, 31 P) and multidimensional NMR spectroscopy was employed for the analysis of diacylglycerol (DAG) oil and the quantification of its acylglycerols and acyl chains composition. A number of gradient selected two dimensional NMR techniques (TOCSY, HSQC-DEPT, HSQC-TOCSY, and HMBC) facilitated the assignment of the complex one dimensional 1 H-and 13 C-NMR spectra. In several cases, the aforementioned 2D-NMR techniques offered solid proof of earlier assignments based on chemical shift changes induced by the presence and relative positions of double bonds within the acyl chains. Integration of the appropriate signals in the NMR spectra of the three nuclei allowed the determination of DAG oil composition, which was found to be within the limits accepted for this oil, namely 1-monoacylglycerols 0.40-0.60%; 2-monoacylglycerols 0.40-0.50%; 1,3-diacylglycerols 57-62%; 1,2-diacylglycerols 28-32%; triacylglycerols 9-11%; saturated fatty acids 3-5%; oleic acid 37-45%; linoleic acid 49-53%; and linolenic acid 5-6.5%; tocopherols 0.24-0.27%. The compositional results obtained from the NMR spectra of the three nuclei were compared and discussed in terms of repeatability and ease of performance.

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“…After integrating the internal reference peak and the 13 C NMR peaks of the glycerol backbone of MAG, DAG and TAG, the concentrations were predicted with the previously prepared calibration model. In the same manner, the residual FFA concentrations were also measured using the carboxylic peak [30] at 179 ppm. To verify the reliability of the method, the FFA concentrations obtained by 13 C NMR were compared with those measured by NaOH titration.…”

Section: Quantificationmentioning

confidence: 99%

¹³C NMR quantification of mono and diacylglycerols obtained through the solvent‐free lipase‐catalyzed esterification of saturated fatty acids

Fernandes

Souza

Azeredo

2012

Magnetic Reson in Chemistry

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In the present investigation, we studied the enzymatic synthesis of monoacylglycerols (MAG) and diacylglycerols (DAG) via the esterification of saturated fatty acids (stearic, palmitic and an industrial residue containing 87% palmitic acid) and glycerol in a solvent-free system. Three immobilized lipases (Lipozyme RM IM, Lipozyme TL IM and Novozym 435) and different reaction conditions were evaluated. Under the optimal reaction conditions, esterifications catalyzed by Lipozyme RM IM resulted in a mixture of MAG and DAG at high conversion rates for all of the substrates. In addition, except for the reaction of industrial residue at atmospheric pressure, all of these products met the World Health Organization and European Union directives for acylglycerol mixtures for use in food applications. The products were quantified by (13)C NMR, with the aid of an external reference signal which was generated from a sealed coaxial tube filled with acetonitrile-d3. After calibrating the area of this signal using the classical external reference method, the same coaxial tube was used repeatedly to quantify the reaction products.

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13C NMR spectroscopy for determining the acylglycerol positional composition of lampante olive oils. Chemical shift assignments and their dependence on sample concentration

Cited by 25 publications

References 28 publications

Nuclear Magnetic Resonance Spectroscopy: A Versatile Tool for Qualitative and Quantitative Analysis of an Emulsifier Mixture of Soybean Oil

Nuclear Magnetic Resonance Spectroscopy: A Versatile Tool for Qualitative and Quantitative Analysis of an Emulsifier Mixture of Soybean Oil

High‐Resolution NMR Spectroscopy: An Alternative Fast Tool for Qualitative and Quantitative Analysis of Diacylglycerol (DAG) Oil

¹³C NMR quantification of mono and diacylglycerols obtained through the solvent‐free lipase‐catalyzed esterification of saturated fatty acids

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13C NMR spectroscopy for determining the acylglycerol positional composition of lampante olive oils. Chemical shift assignments and their dependence on sample concentration

Cited by 25 publications

References 28 publications

Nuclear Magnetic Resonance Spectroscopy: A Versatile Tool for Qualitative and Quantitative Analysis of an Emulsifier Mixture of Soybean Oil

Nuclear Magnetic Resonance Spectroscopy: A Versatile Tool for Qualitative and Quantitative Analysis of an Emulsifier Mixture of Soybean Oil

High‐Resolution NMR Spectroscopy: An Alternative Fast Tool for Qualitative and Quantitative Analysis of Diacylglycerol (DAG) Oil

13C NMR quantification of mono and diacylglycerols obtained through the solvent‐free lipase‐catalyzed esterification of saturated fatty acids

Contact Info

Product

Resources

About

¹³C NMR quantification of mono and diacylglycerols obtained through the solvent‐free lipase‐catalyzed esterification of saturated fatty acids