Analytical Methods. NMR Spectroscopy, a Rapid Method for Any Lipid Analysis. ASAGA World Congress, Rosario Argentina, November2015
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1 Analytical Methods NMR Spectroscopy, a Rapid Method for Any Lipid Analysis ASAGA World Congress, Rosario Argentina, November2015 Bernd W.K. Diehl, Yulia Monakhova, Elina Zailer Spectral Service
2 Analytical Methods Holistic control of edible oils based on NMR spectroscopy NMR for fast quality control of edible oils, 10 minutes measuring time, no reverence material Easy and fast sample preparation o o o o o o o o o o POZ Peroxide AV Aldehyde AV FFA 1,2 and 1,3-DAG 1- and 2-MAG Omega-3 Tocopherol Polyphenol Sterole Additives Identity test using statistical methods o PCA (Principle Component Analysis) o DA (Discriminant analyses) o PLS (Partial Least Squares) Contamination or adulteration Provenience of Olive Oil Spectral Service
3 Alternative: qnmr of Lipids Quality parameter Peroxides (PV) Aldehydes (AV) TOTOX Free Fatty Acids (TAV) Saturated FA Unsaturated FA Omega-3 Iodine Value (JV) 1,2-Diglycerides 1,3-Diglycerides Sterols Cis/Trans-conjugation Tocopherols Spectral Service
4 Internal Reference! CH 3 at chain end = 9H per MOL 1.0 ppm Spectral Service
5 Internal Reference! Glycerol CH 2 = 4H per MOL 4.2 ppm Spectral Service
6 Internal Reference! α CH 2 = 6H per MOL 2.3 ppm Spectral Service
7 Internal Reference! Glycerol CH = 1H per MOL 5.20 ppm 10,00 9,00 8,00 7,00 6,00 5,00 4,00 3,00 2,00 1,00 Internal Reference TAG/FA y = 0,9964x R² = 1 0,00 0,00 2,00 4,00 6,00 8,00 10,00 Spectral Service
8 Jodine Value % DOBI vs Jodine Value JV y = 1,1489x R² = 1 Trilinolenat 5.3 ppm Trioleat Trilinoleat 0 Tristearat Spectral Service
9 Jodine Value JV 5.3 ppm y = 1,1489x R² = 1 Butter % DOBI vs Jodine Value Sesame Oil Olive Oil Walnut Oil Spectral Service
10 Jodine Value Saturated Unsaturated JV unsat. 5.3 ppm 79.5 % unsat 20.5 % sat. 2.1 ppm Spectral Service
11 W-3, 18:2, 18:3 18:3 18:2 ω ppm 1.0 ppm Spectral Service
12 Peroxide Value POV ppm Spectral Service
13 Anisidine Value AV 9.8 ppm Spectral Service
14 TOTOX POV ppm + AV 9.8 ppm + FA ppm Spectral Service
15 1,2 DAG 1,3 DAG 1,2 DAG 1,3 DAG Ratio of 1,2 to 1,3 DAG Is essential for Olive oil quality 4.9 ppm 3.6 ppm Spectral Service
16 Free Fatty Acids FFA 2.20 ppm Spectral Service
17 Secondary Compound α Toc. 7.4 ppm Squalene 5.1 ppm Sterols 0.70 ppm Spectral Service
18 Complete Analysis JV FFA Sterols 5.3 ppm 2.20 ppm 0.70 ppm unsat. POV 1,3 DAG 1,2 DAG 18:3 18:2 2.1 ppm ppm 4.9 ppm 3.6 ppm 2.8 ppm ω-3 AV 9.8 ppm α Toc. 7.4 ppm Squalene 5.1 ppm 1.0 ppm Spectral Service
19 NMR of Olive Oils Quality parameter By 1 H NMR in 5 min Peroxides (PV) Aldehydes (AV) Free Fatty Acids (TAV) Iodine Value (JV) Saturated Unsaturated FA Omega-3 1,2- and1,3-diglycerides Sterols, Tocopherols, Polyphenols Origin and Provenience By 1 H NMR in 5 min Identity and origin of Olive oil by targeted Analysis of the Polyphenol and Sterol composition By 13 C NMR in 30 min Regioselective FA distribution Spectral Service
20 Internal Calibration Integral CH=CH = Iodine Number 2 CH 2 = 4 CH = ppm Spectral Service
21 Fatty Acid Composition 18:2 α-ch 2 = 6 H Allylic = unsat. 18:3 18:3 β-ch 2 = 6 H 2.8 ppm ppm ppm Spectral Service
22 NMR vs GC Spectral Service
23 NMR vs GC Spectral Service
24 Validation Validation data are published: POV C. Skiera, B.W.K. Diehl et al: J Am Oil Chem Soc AV C. Skiera, B.W.K. Diehl, et al 1. Euro Food Res Tech, 2012 TOTOX B.W.K. Diehl, EJLST, sub 2014 IV Y. Miyake et al, JOFI, 12/1998 FFA C. Skiera, B.W.K. Diehl, et al, JPBA, 2013 Tocopherol Spectral Service intern Vitamins B.W.K. Diehl, Y. Monakhova, J. Eiff, JAFC, 2015 DAG MAG Spectral Service intern Fa Composition Spectral Service vs. GC/MS and HPLC/MS intern Egg liquor M. Hohmann, B.W.K. Diehl,et al, JAFC, 2015 Spectral Service
25 Statistical Test A by-product Spectral Service
26 Statistical Test Spectral Service
27 Lipid Oxidation Hydroperoxides of FA FFA Hydroperoxides of Squalene Hexanal ppm Spectral Service
28 60 Spectroscopy 1 H NMR, Oxidation of vegetable Oils PV [meq/kg] NMR [mmol/kg] sunflower oil thisle oil nut oils rapeseed oil corn oil olive oil black seed oil pumpkin seed oil further oils Spectral Service
29 1,2 vs 1,3 DAG Test of Aging Squalene * 64 1,2 DAG 1,3 DAG ppm Spectral Service
30 1,2 vs 1,3 DAG Test of Aging Glycerol Carbons TAG sn2 TAG sn1/3 1,2 DAG sn2 1,3 DAG sn1/3 1,2 DAG sn1 1,2 DAG sn3 Sterol 1,3 DAG sn 2 Sterol ppm Spectral Service
31 1,2 vs 1,3 DAG Test of Aging Carbonyl 1,3 DAG 1,2 DAG 18:1 TAG sn1/3 sn1 sn 2 sat 18:1 sn1/3 sn 2 18:2 20:1 18: ppm Spectral Service
32 1,2 vs 1,3 DAG Test of Aging 1,3 DAG 1,2 DAG sn1/3 sn1 TAG sn1/ ppm ppm ppm Spectral Service
33 13 C NMR Regiospecivity 18:2 1/2 hour additional measuring time on 600 MHz cqnp 18:3 18:3 Squalene ppm ppm Spectral Service
34 13 C NMR Regiospecivity Walnut ppm Spectral Service
35 13 C NMR Regiospecivity 18:2 18:2 Hazelnut 18:3 18: ppm Spectral Service
36 13 C NMR Regiospecivity 18:2 18:2 Linseed Oil 18:3 18:3 sn2 sn1/ ppm Spectral Service
37 Phenols Dialdehydic, hemiaacetal and aldehydic forms of oleuropein, ligstroside and elenoic acid. Spectral Service
38 Polyphenols Spectral Service
39 Sterols Spectral Service
40 Sterols Spectral Service
41 Statistical Methods Spectral Service
42 Chia Seed Program V.Y. Ixtaina, M.L. Martínez,, V. Spotorno, C.M. Mateo,, D.M. Maestri, B.W.K. Diehl, S.M. Nolasco, M.C. Tomás, Characterization of chia seed oils obtained by pressing and solvent extraction. Journal of Food Composition and Analysis, volume 24, issue 2, year 2011, pp Muchas Gracias Spectral Service
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