Analysis & occurrence of bound glycidol and MCPD in oil containing foods SGS Germany GmbH J. Kuhlmann

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1 Analysis & occurrence of bound glycidol and MCPD in oil containing foods SGS Germany GmbH J. Kuhlmann 1

2 Introduction 2-MCPD, 3-MCPD & Glycidol: Glycerolderivates + HCl - H 2 O 3-MCPD (3-Chloropropane-1,2-diol) 2-MCPD (2-Chloropropane-1,3-diol) Glycerol - HCl + HCl - H 2 O Glycidol 2

3 (fatty acid) bound Glycidol & MCPD in oils & fats Introduction crude oil refining refined oil Bound MCPD & Glycidol are generated mainly during deodorisation. The formation of these process contaminants depends upon the oil composition and process control. 3

4 Introduction Generation of bound Glycidol & MCPD from natural oil components Mono- & Diacylglycerides (Glycerol mono- & di-fatty acid esters = bound glycerol ) Deo-Temp. > 200 C Glycidyl ester fatty acid mono-esters representative to fatty acid composition low boiling points reactive epoxy-funktion; limited stability starting at Temp. < 200 C natural (!) HCl-sources: e.g. FeCl x, chlorinated phytosphingosides 1) 2- & 3-MCPD-ester fatty acid 1-/2-Mono- & 1,2-/1,3-Di-esters high boiling points ; persistant compounds Glycidylpalmitate 3-MCPD-1,2-bis-pamitoyl-ester 1) K. Nagy et al.: Mass-defect filtering of isotope signatures to reveal the source of chlorinated palm oil contaminants; Food Addit. Contam. 2011, 28,

5 Introduction Toxicological impact of MCPD free 3-MCPD Some in-vivo studies indicated toxic effects especially to kidneys and testes after oral uptake. MRL (Maximum Residue Limit): 20 µg/kg in HVP & HVP-products EU Commission Regulation N 466/2001 bound 3-MCPD TDI (Tolerably Daily Intake): 2 µg/kg bw d Recent in-vivo studies have shown that the majority of 3-MCPD is released from its bound form during digestion. In-vivo released 3-MCPD causes similar toxic effects like the uptake of free 3-MCPD 2) free & bound 2-MCPD Same story as last year: still very little analytical and almost no toxicological data available 2) EFSA (2011). Scientific report submitted to EFSA Comparison between 3-MCPD and its palmitic esters in a 90-day toxicological study prepared by E. Barocelli, A. Corradi, A. Mutti and P.G. Petronini, University of Parma, Parma, Italy. CFP/EFSA/CONTAM/2009/01. 5

6 Introduction Toxicological impact of glycidol free glycidol Epoxides are highly reactive an combine with many chemical groups Several serious toxic effects have been proven in in-vitro & in-vivo studies Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP] Acute toxicity, Oral (Category 4) Acute toxicity, Inhalation (Category 3) Acute toxicity, Dermal (Category 4) Skin irritation (Category 2) Eye irritation (Category 2) Germ cell mutagenicity (Category 2) Carcinogenicity (Category 1B) Reproductive toxicity (Category 1B) Specific target organ toxicity - single exposure (Category 3) Classification according to EU Directives 67/548/EEC or 1999/45/EC Toxic by inhalation. May cause cancer. May impair fertility. Harmful in contact with skin and if swallowed. Possible risk of irreversible effects. Irritating to eyes, respiratory system and skin. Bound glycidol So far no data available (actual studies by the German Federal Institute of Risk Assessment (BfR) in progress) The release of free glycidol from its bound form excerpt material safety data sheed Sigma-Aldrich Co. G

7 Direct analysis; determination of the original esters Analytics glycidol 3-MCPD 2-MCPD Fatty acid(s) Hypothetic oil Contains only 3 relevant fatty acids This yields up to 3 Glycidyl ester 9-MCPD-mono-ester 15 MCPD-di ester maybe Matrix-clean-up LC-MS Chromatogram displays up to 27 analytes! 7

8 Hypothetic oil Contains only 3 relevant fatty acids This yields up to 3 Glycidyl ester 9-MCPD-mono-ester 15 MCPD-di -ester Analytics Indirect analysis; determination of the released analytes Ester cleavage Matrix removal 3-MCPD Derivatisation GC-MS glycidol 2-MCPD Chromatogram displays up to 3 analytes! 8

9 EFSA (2011). Scientific report submitted to EFSA Comparison between 3-MCPD and its palmitic esters in a 90-day toxicological study prepare Analytics Indirect analysis; different methods acidic ester cleavage; 2- & 3-MCPD are stable; glycidol is instable bound 2- & 3- MCPDester Glycidylester H + ca. 16 h shorter (Unilever) 2-MCPD 3-MCPD Glycidol alkaline ester cleavage; glycidol is stable but 3-MCPD reacts to glycidol A) acidic reaction stop in presence of chloride; original and induced glycidol reacts to 3-MCPD. free A bound 2- & 3- MCPDester Glycidylester OH min 2-MCPD 3-MCPD Tf Glycidol free H + / Cl - 2-MCPD 3-MCPD A: Sum 3-MCPD & Glycidol (A-B)xTf = Glycidol DGF C-VI 18 (10) A,B B H + / chloride free 2-MCPD 3-MCPD Glycidol B: True 3- MCPD- value B) acidic reaction stop in absence of chloride 9

10 Analytics Indirect analysis - SGS method 3-in-1 Bound 3- & 2- MCPD Mild alkaline ester cleavage Free 3- & 2- MCPD Glycidoltransformation with H + / Br - Free 3- & 2- MCPD Matrix removal Derivatisation with PBA* * Phenyl Boronic Acid GC/MS-Analysis Bound Glycidol ca. 16 h Free Glycidol Free 3- & 2- MBPD 3-MCPD* 2-MCPD* Glycidol as 3-MBPD* Mild reaction conditions minimize the undesired transformation of 3-MCPD into glycidol (artefact minimisation, high MCPD sensitivity) The transformation of the instable glycidol into 3-MBPD generates a highly stable derivative with excellent gas chromatographic performance (robust & sensitive glycidol determination) Isotopic labelled & esterified analytes for internal standard purposes are commercially available (best quantification approach) Micro size sample preparation results in low organic solvent consumption of approximately 8 ml/sample (sustainable laboratory practise) 10

11 Occurrence Vegetable baking & frying fats Determination of bound glycidol & MCPD in vegetable baking & frying fats from the local German market 18,00 mg/kg g 15,00 12,00 9,00 6,00 3,00 0,00 bound glycidol bound 3-MCPD bound 2-MCPD 70 kg 0,9 0,3 0,1 N 1 N 2 3-MCPD = 3.7 mg/kg N 3 0,2 0,4 N 4 N 5 N 6 Fat N kg TDI 140 µg/d = 38 g fat/d Σ analytes = 16.3 mg/kg if assumed as 3-MCPD impact = 8.6 g fat/d 0,6 1,5 0,9 0,3 0,9 1,5 2,5 3,7 N 7 0,7 1,1 N 8 N 9 2,3 N 10 N 11 11,1 1,5 2,6 N 12 N 13 0,3 5,5 11

12 Occurrence Occurrence of bound Glycidol & MCPD in other foodstuff Infant formula Coffee creamer French fries, fried potatoes, chips, mayonnaise Spreads, dressings, margarine Almost all foods containing refined oils and fats may contain bound glycidol and MCPD Positive findings are frequently in the middle µg/kg up to the low mg/kg range (German market products) Chocolate & nut- nougat spreads Cookies, cakes, cruller ω-3 Dietary supplement oils Instant soups Tofu meals vegetarian sausage/lard/etc. Chocolates 12

13 Occurrence Influence of customary frying Olive oil extra virgin Olive oil in parts refined Butter Liquid paraffine frying oil bound 2-MCPD bound 3-MCPD bound glycidol x 3! analyte mg/kg f start start afo: after frying of m.t.: moderate temperature h.t.: high temperature 13

14 Summary Bound MCPD & glycidol are toxicologically relevant process contaminants; bound glycidol can be assumed to be more hazardous. The analysis of these compounds is sophisticated but feasible. SGS has developed two methods for the determination of bound MCPD & glycidol (DGF C-VI 18 (10) and 3-in-1 ). Bound MCPD & glycidol may occur widespread in foods containing refined oils and fats. Bound 2-MCPD and glycidol together with 3-MCPD should be taken into account to evaluate toxicological relevant over-all exposure. Very first preliminary results of frying experiments indicate that bound MCPD may be generated during the frying of meat and fish with edible oils or fats. 14

15 Many thanks to the lab team: Svetlana Barantseva Laetitia Marchal Juliane Dircks Lan Ly & Alexandra Reisig SGS Germany GmbH Dr. Jan Kuhlmann Weidenbaumsweg 137 D Hamburg Tel.: +49 (0) mobile: +49 (0) Thank you for your kind attention! 15

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