Analysis of MCPD- and Glycidyl- Esters in edible oils
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1 Analysis of MCPD- and Glycidyl- Esters in edible oils Dubois Mathieu Nestlé Research Center Lausanne Switzerland
2 Extraction methods Direct vs Indirect method comparison Analytical standard management LC-MS of MEs and s Background Agenda 2
3 MCPD- and glycidyl-esters Esters of Mono-Chloro-Propane-Diol ccurrence: thermally processed foods vegetable fats/oils (Highest amounts in refined palm oil) R R R Cl 3-MCPD diesters Concern: intrinsic toxicity release of 3-MCPD: - carcinogen - TDI of 2 µg/kg bw (EC, JECFA) - regulatory limit (EC): 2 µg/kg in HVP and soy sauce (CDEX limit of 4 µg/kg) release of 2-MCPD R H H R = alkyl Cl Cl 3-MCPD monoesters currence: refined fats and oils (Highest amounts in refined palm oil) Concern: Esters of glycidol intrinsic toxicity (unknown) release of glycidol: - genotoxic carcinogen - no safety limit H 2 C H 2 C CH R R= alkyl Walburga Seefelder NRC-QS 3
4 Indirect analysis for MEs and s Hydrolysis Derivatization Analysis Free- MCPD MCPDesters 2-MCPD 3-MCPD MCPD derivatized Glycidyl esters Ease of use Already in place nly 2 chemical standards Precision impaired by: Hydrolysis Derivatisation Internal standards (labeled ME) 4
5 7 indirect methods for MCPD and glycidyl-esters analysis 5
6 Extraction methods Direct vs Indirect method comparison Analytical standard management LC-MS of MEs and s Background Agenda 6
7 MCPD and glycidyl esters are very similar in nature to TAG/DAG and MAG MCPD MCPD mono-esters mono-esters Cl H Cl H n n Sn1-3-MCPDmono-esters Sn2-3-MCPDmono-esters MCPD MCPD di-esters di-esters Cl Cl n1 n2 n1 n2 3-MCPDdi-esters 2-MCPDdi-esters Matrix Matrixesters of of glycerol glycerol H n1 n3 n1 n2 n=? CH n=? 3 n2 TAG DAG Cl H n Sn1-2-MCPDmono-esters glycidyl-esters glycidyl-esters () () n H H n1 MAG Seefelder et al. Eur. J. Lipid Sci. Technol 113 (3), (211)
8 Which standards to match fatty acid composition of oils % 6% 8% 2 Rational approach for glycidyl- and MCPD-mono-esters 8 Sunflower oil Safflower oil Palm Kernel oil live oil Grape seed oil Corn oil Coconut oil Canola oil Soybean oil Palm oil Linolenic acid Linoleic Acid leic acid Stearic acid Palmitic acid Myristic acid Lauric acid Capric acid Caprylic acid % Not available as s and MCPD mono-esters analytical standards
9 Which standards to match fatty acid composition of oils 8 % Sunflower oil Soybean oil Safflower oil Palm Kernel oil Palm oil live oil Grape seed oil Corn oil Coconut oil Canola oil Linolenic acid Linoleic Acid leic acid Stearic acid Palmitic acid Myristic acid Lauric acid Capric acid Caprylic acid Glycidyl- esters: Glycidyl laurate (C12:) Glycidyl myristate (C14:) Glycidyl palmitate (C16:) Glycidyl stearate (C18:) Glycidyl oleate (C18:1) Glycidyl linoleate (C18:2) Glycidyl linolenate (C18:3) Same rational 7+7 standards 3-MCPD- mono- esters: 1-lauryl-3-MCPD (C12:) 1-myristyl-3-MCPD (C14:) 1-palmityl-3-MCPD (C16:) 1-stearyl-3-MCPD (C18:) 1-oleyl-3-MCPD (C18:1) 1-linoleyl-3-MCPD (C18:2) 1-linolenyl-3-MCPD (C18:3) 9
10 il samples follow this simple model s distribution in 13 palm oil samples measured theory 1% 9% 8% 7% 6% 5% 4% 3% 2% 1% % Simple approach allow: laurate myristate palmitate stearate oleate linoleate linolenate - Identifiy distribution trend s distribution in 4 coconut oil samples measured theory - Check of standard scope 1% 9% 8% 7% 6% 5% 4% 3% 2% 1% % But does not consider: - Natural position preferences - Variability within oil type laurate myristate palmitate stearate oleate linoleate linolenate 1
11 Situation is even more complex with 3-MCPD diesters Theoretical example of palm oil: 3-MCPD-di-esters chemical standards to cover all possibilities: 49 standards 1% 3-MCPD di-ester content (Theory) 25 2 Theoretical distribution % 15 n1 1 5 Cl n2 Lauric acid Myristic acid Palmitic acid sn 1 FA Stearic acid leic acid Linoleic Acid Linolenic acid Linolenic acid Linoleic Acid leic acid Stearic acid Palmitic acid Lauric acid Myristic acid 11
12 Situation is even more complex with 3-MCPD diesters Theoretical example of palm oil: 3-MCPD-di-esters chemical standards to cover all possibilities: 49 standards 1% 3-MCPD di-ester content (Theory) 28 standards 1% 3-MCPD di-ester content (Experimental) 4 Theoretical distribution n1 % Cl n2 Lauric acid Myristic acid Pamitic acid Stearic acid sn 1 FA leic acid Linoleic Acid Linolenic acid Linolenic acid Linoleic Acid leic acid Stearic acid Palmitic acid Lauric acid Myristic acid 12
13 Situation is even more complex with 3-MCPD diesters Theoretical example of palm oil: 3-MCPD-di-esters chemical standards to cover all possibilities: 49 standards 1% 3-MCPD di-ester content (Theory) 28 standards 1% 3-MCPD di-ester content (Experimental) 1 standards 98% 3-MCPD di-ester content (Pragmatic) 4 Theoretical distribution 35 il 3-MCPD di-esters coverage (1 standards included ) canola oil 93% corn oil 98% cotton seed il 96% grape seed oil 99% olive oil 95% palm oil 98% palm lein 96% safflower oil 99% soybean oil 9% % Lauric acid Myristic acid Pamitic acid Stearic acid sn 1 FA leic acid Linoleic Acid Linolenic acid Linolenic acid Linoleic Acid leic acid Stearic acid Palmitic acid Lauric acid Myristic acid 13
14 Situation is even more complex with 3-MCPD diesters Theoretical example of palm oil: 3-MCPD-di-esters chemical standards to cover all possibilities: 49 standards 1% 3-MCPD di-ester content (Theory) 28 standards 1% 3-MCPD di-ester content (Experimental) 1 standards 98% 3-MCPD di-ester content (Rational) 6% Measured in 22 palm oil samples Theoretical in Palm oil 5% 4% 3% 2% 1% Approach confirmed by samples analysis % +LS PP LL+Ln L S PL P PS 14
15 Issues with palm kernel and coconut oil Current available standards do not fit with: - Palm kernel oil 7.8% 3-MCPD di-ester coverage - Coconut oil 3.9% 3-MCPD di-ester coverage Theoretical distribution in palm kernel oil 25 2 Not available: custom synthesis required 15 % 1 5 Caprylic acid Capric acid Lauric acid Myristic acid Palmitic acid sn 1 FA Stearic acid 2.4 leic acid Linoleic Acid Linolenic acid Linolenic acid Linoleic Acid leic acid Stearic acid Palmitic acid Myristic acid Lauric acid Capric acid Caprylic acid 15
16 Quantitation requires standard addition or labeled standards Standard addition: control matrix effect External calibration: IS mandatory (custom synthesis) Relative Abundance * * ** n Relative Abundance * * * Cl * H n Relative Abundance * * * Cl * * n1 n m/z m/z m/z m/z m/z m/z 16
17 Standard addition (on extracts) vs external calibration (labeled standards) Comparison if standard addition vs external calibration on Ges: 4 s with corresponding 4 s IS ( 13 C 3/4 ) 5 palm oil samples 1 Std addition on extracts (value in µg/kg) y = 1.66x R² = Glycidyl-palmitate Glycidyl-stearate Glycidyl-oleate Glycidyl-linoleate Glycidyl-linolenate Tolerance int. (95%) Linear (Y = X) Ext. Calib with IS (value in µg/kg) Conclusion: Few IS to check recoveries in each sample Standard addition on extracts 17
18 Extraction methods Direct vs Indirect method comparison Analytical standard management LC-MS of MEs and s Background Agenda 18
19 LC-MS of MCPD- and glycidyl- esters Solubilization + IS (if available) Extraction Liquid chromatography Mass spectrometry Solvent compatible with extraction IS: check recoveries SEC (GPC) SPE (Si, C18) Preparative/ MPLC C18 column Mobile phases TF, QTF: identification, method development QqQ: routine analysis 19
20 Chromatographic separation ToF detection Column: Waters Acquity HSS T3 (5x2.1mm, 1.8µm) Elution: A MeH:H2 75:25 (1mM ammonium formate,.1% HCH ) B: Isopropanol (1mM ammonium formate,.1% HCH) Run time: 15 min between injection glycidyl-esters MCPDmono-esters MCPDdi-esters glycidyl-laurate glycidyl-myristate glycidyl-linolenate glycidyl-linoleate glycidyl-palmitate glycidyl-oleate glycidyl-stearate 1 myristoyl-3-chloropropanediol 1 lauroyl-3-chloropropanediol 1 palmitoyl-3-chloropropanediol 1 stearoyl-3-chloropropanediol 1 oleyl-3-chloropropanediol 1 linoleoyl-3-chloropropanediol 1 linolenoyl-3-chloropropanediol 1,2-bis-palmitoyl-3-chloropropanediol 1-palmitoyl-2-stearoyl-3-chloropropanediol 1,2-dilinoleoyl-3-chloropropanediol 1-oleoyl-2-stearoyl-3-chloropropanediol 1-linoleoyl-2-stearoyl-3-chloropropanediol 1-oleoyl-2-linolenoyl-3-chloropropanediol 1-oleoyl-2-linoleoyl-3-chloropropanediol 1-palmitoyl-2-linoleoyl-3-chloropropanediol 1,2-bis-oleoyl-3-chloropropanediol 1-oleyl-2-palmitoyl-3-chloropropanediol 2
21 MCPD mono-esters: what is detected? 2.95 Sn1-3-MCPD mono-esters H Cl 2.98 Sn1-2-MCPD mono-esters Cl H H 2.98 Sn2-3-MCPD mono-esters Cl MCPD mono-esters: No separation of isomers (2-,3-MCPD, Sn1 and Sn2) Different MS response (e.g. 2-palmitoyl-3-MCPD is 4% less than Sn1) 21
22 MCPD di-esters: what is detected? Cl Cl di-stearoyl-3-mcpd di-stearoyl-2-mcpd Mix 1:1 MCPD di-esters: No separation of isomers (2- and 3-MCPD) Different MS response (e.g. Di-stearoyl-2-MCPD is 3% less) 22
23 Extraction methods Direct vs Indirect method comparison Analytical standard management LC-MS of MEs and s Background Agenda 23
24 Low level determination and high throughput "Dilute and shoot" Sample prep. Common chromatographic conditions Rapid Instrument stability Matrix effect Less maintenance Sensitivity Sensitivity Method robustness High frequency Instrument cleaning Sensitivity (µg/kg) Sensitivity (µg/kg) Inj. Inj. 24
25 Method n 1: Gel Permeation Chromatography (GPC) for purification Weißhaar et al. Eur. J. Lipid Sci. Technol. 21, 112, Conditions: 1g oil in 1mL (Clyclohexane : Ethyl Acetate 1:1) 4 ml injected on SX3 BioBeads (Bio-Rad), flow at 5 ml/min Collect 9-13mL Dry under vacuum Area 2.E+8 2.E+8 1.E+8 5.E+7 Palm oil elution profile DAG TAG s collection -laurate -linoleate -linolenate -myristate -oleate -palmitate -stearate E Elution Volume (ml) Additional clean up for high MAG/DAG content SPE Si cartridges (5mg) CH2Cl2 (1 ml) elution LQ =.5 mg/kg 25
26 s: Indirect vs Direct method 1 palm oil samples analysed by: Nestlé (Direct Method: GPC, SPE, QqQ analysis) External laboratory (Indirect Method : alkaline hydrolysis, PBA derivatization, GC-MS analysis) Indirect vs direct -1 palm oil samples Tolerance int. (95%) Y=X Linear (Indirect vs Direct) External Indirect method glycidol in µg/g y = x R² =.9916 Systematic Bias:.3µg/g Proportional Bias : Direct method glycidol in µg/g 26
27 MCPD esters are not separated from TAG and DAG by GPC MCPD monoesters MCPD di-esters Method 1: GPC Method 2: C18+Si Method 3: Si Lack of resolution: TAG MCPD-di-esters DAG MCPD-di-esters DAG MCPD-mono-esters Material tested: SX1; SX3; SX8 Area Area 2.5E+8 2.5E+8 TAG 2.E+8 TAG 2.E+8 1.5E+8 1.5E+8 1.E+8 1.E+8 5.E+7 5.E+7 MCPD MCPD mono-esters MCPD DAG MCPD mono-esters di-esters DAG di-esters Glycidyl esters Glycidyl esters.e+.e Elution Volume (ml) Elution Volume (ml) No extension of GPC method for MCPD-esters 27
28 Method n 2 for MEs (mono-esters) and s Masukawa et al. J. leo Sci. 59, (2) (21) Shimizu et al. J. leo Sci. 59 (1), (21) Masukawa et al. JACS 88 (1), (211) 1st SPE: C18: 2g C18,1mg oil, 25ml ACN 1.E+7 s MCPD-mono DAG TAG 8.E+6 s MCPD-mono DAG TAG 8.E+6 6.E+6 Area 6.E+6 4.E+6 Area 4.E+6 2.E+6 2.E+6.E+.E ml (Methanol) ml (Acetonitrile) 2nd SPE: Si: 5mg, 25ml CH 2 Cl 2 s MCPD mono 1.E+7 1.E+6 Area s 1.E+7 8.E+6 6.E+6 4.E+6 2.E+6.E+ 1.E+6 1.E+6 8.E+5 6.E+5 4.E+5 2.E+5.E ml CH2Cl2 Area MCPD mono Less co-extracted matrix with ACN (SPE C18) MCPD di-esters coelute with TAG (SPE C18) No DAG after Si-SPE 28
29 Method n 2: recoveries 2 g C mg silica gel SPE 6 palm oil sample spiked at.5 µg/g and 1µg/g. MCPD monoesters MCPD di-esters Method 1: GPC Method 2: C18+Si Method 3: Si 16% 14% 12% 1% 8% 6% 4% 2% % Spiking.5µg/g Spiking 1µg/g 29
30 Method n 3 for MEs (di-esters) Silica gel chromatography column SiH 3g, 4mg oil in in hexane 65ml CH2Cl2 4% in in hexane Area Area MPLC :1g Snap, 1mg palm oil MPLC :1g Snap, 1mg palm oil 1.4E E E+7 1.2E E E+7 8.E E E E E+6 4.E E E+6.E+.E Elution volume (ml) 4 5 Elution volume (ml) isocratic CH 2 Cl 2 % Diethyl-ether in hexane % Diethyl-ether in hexane MCPD di MCPD di MCPD mono MCPD mono DAG (area/5) DAG (area/5) TAG (area/5) TAG (area/5) % Diethyl-ether in hexane % Diethyl-ether in hexane MCPD di-esters Area MCPD di-esters Area m SiH /m oil > 75 MCPD mono-esters : DAG interference s: high volume 3.E+ 3.E+ 2.5E+ 2.5E+ 2.E+ 2.E+ 1.5E+ 1.5E+ 1.E+ 1.E+ 5.E-1 5.E-1 Method n 3 : 3g SiH, 4 mg oil Method n 3 : 3g SiH, 4 mg oil collect.e+.e Elution volume (ml) Elution volume (ml) 1-palmitoyl-2- stearoyl-3-1-palmitoyl-2- chloropropanediol stearoyl-3- bis-palmitoyl-3- chloropropanediol chloropropanediol bis-palmitoyl-3- chloropropanediol di-oleate-3- chloropropanediol di-oleate-3- chloropropanediol oleate-palmitate-3- chloropropanediol oleate-palmitate-3- chloropropanediol TAG TAG 3
31 Method n 3: recoveries 3 g silica gel 6 palm oil sample spiked at.5 µg/g and 1µg/g. MCPD monoesters MCPD di-esters Method 1: GPC Method 2: C18+Si Method 3: Si 18% 16% 14% 12% 1% 8% 6% 4% 2% % Spiking.5 µg/g Spiking 1 µg/g 31
32 MEs: Direct vs Indirect method 32 oil samples analysed by: Direct Method: MCPD mono-esters (2x SPE) + MCPD di-esters (silica) LC-ToF Indirect Method : acidic hydrolysis, HFBI derivatization GC-MS Σ 7 MEs (mono) + Σ 1 MEs (di) direct indirect 2-MCPD + 3-MCPD Direct method, MCPD in µg/g (Sum MCPD mono- and di-esters) y =.9747x R² =.9639 Total MCPD in µg/g Direct vs Indirect method Indirect method,mcpd in µg/g (Sum 3- and 2-MCPD ) palm oil Palm olein sunflower coconut oil Palm kernel oil Y = X 1% 8% 6% 4% 2% % 29 palm oil samples 65% 3-MCPD (Indirect) 9% MCPD di-esters (Direct) Comparable results 32
33 Conclusion No detection issue for direct determination: LC-HRMS or MS/MS fit for purpose Sample preparation highly required for better sensitivity and robustness Method Convenience (Quick, easy, cheap, robust) Direct GPC 7 Standards automated MCT oils 2 Standards all matrices analyte transformation Indirect 2- and 3-MCPD3 Recommendation 14 Standards 2 extractions s recoveries Direct Silica Column s Direct 2x SPE (C18 (C18 + SiH) MCPD mono-esters all matrices standards availability MCPD di-esters Compound class 33
34 Alfred Donaubauer Walburga Seefelder Till Goldmann Adrienne Tarres Aknowledgements
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