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The occurrence of 3-monochloropropane-1,2-diol esters and glycidyl esters in vegetable oils during frying

Ahmad Tarmizi AH, Kuntom A

Crit Rev Food Sci Nutr, 2021 Jan 05.
PMID: 33397128 DOI: 10.1080/10408398.2020.1865264

3-monochloropropane-1,2-diol esters (3-MCPDE) and glycidyl esters (GE) are processed-developed contaminants presence in vegetable oils after undergo refining process under excessive heat. Refined oils are extensively used in various frying applications, nevertheless, the reservation against their quality and safety aspects are of major concern to consumers and food industry. Realizing the importance to address these issues, this article deliberates an overview of published studies on the manifestation of 3-MCPDE and GE when vegetable oils undergo for frying process. With the modest number of published frying research associated to 3-MCPDE and GE, we confined our review from the perspectives of frying conditions, product properties, antioxidants and additives, pre-frying treatments and frying oil management. Simplicity of the frying process is often denied by the complexity of reactions occurred between oil and food which led to the development of unwanted contaminants. The behavior of 3-MCPDE and GE is closely related to physico-chemical characteristics of oils during frying. As such, relationships between 3-MCPDE and/or GE with frying quality indices - i.e. acidity in term of free fatty acid or acid value); secondary oxidation in term of p-anisidine value, total polar compounds and its fractions, and refractive index - were also discussed when oils were subjected under intermittent and continuous frying conditions.
Development of palm-based reference materials for the quantification of fatty acids composition

Tarmizi AH, Lin SW, Kuntom A

J Oleo Sci, 2008;57(5):275-85.
PMID: 18391476

Characterisation of fatty acids composition of three palm-based reference materials was carried out through inter-laboratory proficiency tests. Twelve laboratories collaborated in these tests and the fatty acids compositions of palm oil, palm olein and palm stearin were determined by applying the MPOB Test Methods p3.4:2004 and p3.5:2004. Determination of consensus values and their uncertainties were based on the acceptable statistical agreement of results obtained from the collaborating laboratories. The consensus values and uncertainties (%) for each palm oil reference material produced are listed as follows : 0.20% (C12:0), 1.66+/-0.05% (C14:0), 43.39+/-0.39% (C16:0), 0.14+/-0.06% (C16:1), 3.90+/-0.11% (C18:0), 40.95+/-0.23% (C18:1), 9.68+/-0.21% (C18:2), 0.16+/-0.07% (C18:3) and 0.31+/-0.08% (C20:0) for fatty acids composition of palm oil; 0.23+/-0.04% (C12:0), 1.02+/-0.04% (C14:0), 39.66+/-0.19% (C16:0), 0.18+/-0.07% (C16:1), 3.81+/-0.04% (C18:0), 44.01+/-0.08% (C18:1), 10.73+/-0.08% (C18:2), 0.20+/-0.06% (C18:3) and 0.34+/-0.04% (C20:0) for fatty acids composition of palm olein; and 0.20% (C12:0), 1.14+/-0.05% (C14:0), 49.42+/-0.25% (C16:0), 0.16+/-0.08% (C16:1), 4.15+/-0.10% (C18:0), 36.14+/-0.77% (C18:1), 7.95+/-0.29% (C18:2), 0.11+/-0.07% (C18:3) and 0.30+/-0.08% (C20:0) for fatty acids composition of palm stearin.
Palm-based standard reference materials for iodine value and slip melting point

Tarmizi AH, Lin SW, Kuntom A

Anal Chem Insights, 2008 Sep 22;3:127-33.
PMID: 19609396

This work described study protocols on the production of Palm-Based Standard Reference Materials for iodine value and slip melting point. Thirty-three laboratories collaborated in the inter-laboratory proficiency tests for characterization of iodine value, while thirty-two laboratories for characterization of slip melting point. The iodine value and slip melting point of palm oil, palm olein and palm stearin were determined in accordance to MPOB Test Methods p3.2:2004 and p4.2:2004, respectively. The consensus values and their uncertainties were based on the acceptability of statistical agreement of results obtained from collaborating laboratories. The consensus values and uncertainties for iodine values were 52.63 +/- 0.14 Wijs in palm oil, 56.77 +/- 0.12 Wijs in palm olein and 33.76 +/- 0.18 Wijs in palm stearin. For the slip melting points, the consensus values and uncertainties were 35.6 +/- 0.3 degrees C in palm oil, 22.7 +/- 0.4 degrees C in palm olein and 53.4 +/- 0.2 degrees C in palm stearin. Repeatability and reproducibility relative standard deviations were found to be good and acceptable, with values much lower than that of 10%. Stability of Palm-Based Standard Reference Materials remained stable at temperatures of -20 degrees C, 0 degrees C, 6 degrees C and 24 degrees C upon storage for one year.
High Throughput Residue Analysis of Indaziflam and its Metabolites in Palm Oil Using Liquid Chromatography-Tandem Mass Spectrometry

Halim N, Kuntom A, Shinde R, Banerjee K

J AOAC Int, 2020 Sep 01;103(5):1237-1242.
PMID: 33241391 DOI: 10.1093/jaoacint/qsaa041

BACKGROUND: Indaziflam (IND) is a herbicide that is used in palm oil plantations for broad spectrum management of weeds. Until now, no validated method has been available for residue estimation of this herbicide in palm oil products.
OBJECTIVE: In this study, we report a rapid method for the residue analysis of IND and its metabolites, viz., IND-carboxylic acid, diaminotriazine, and triazine indanone in a wide range of palm oil matrices using liquid chromatography-tandem mass spectrometry (LC-MS/MS).
METHOD: The optimized sample preparation workflows included two options: (1) acetonitrile extraction (QuEChERS workflow), followed by freezing at -80°C and (2) acetonitrile extraction, followed by cleanup through a C18 solid phase extraction (SPE) cartridge. The optimized LC runtime was 7 min. All these analytes were estimated by LC-MS/MS multiple reaction monitoring.
RESULTS: Both sample preparation methods provided similar method performance and acceptable results. The limit of quantification (LOQ) of IND, IND-carboxylic acid, and triazine indanone was 0.001 mg/kg. For diaminotriazine, the LOQ was 0.005 mg/kg. The method accuracy and precision complied with the SANTE/12682/2019 guidelines of analytical quality control.
CONCLUSIONS: The potentiality of the method lies in a high throughput analysis of IND and its metabolites in a single chromatographic run with high selectivity and sensitivity. Considering its fit-for-purpose performance, the method can be implemented in regulatory testing of IND residues in a wide range of palm oil matrices that are consumed and traded worldwide.
HIGHLIGHTS: This work has provided a validated method for simultaneous residue analysis of indaziflam and its metabolites in crude palm oil and its derived matrices with high sensitivity, selectivity, and throughput.
Study on the downward movement of carbofuran in two Malaysian soils

Farahani GH, Sahid IB, Zakaria Z, Kuntom A, Omar D

Bull Environ Contam Toxicol, 2008 Sep;81(3):294-8.
PMID: 18587522 DOI: 10.1007/s00128-008-9468-8

The downward movement of carbofuran in two Malaysian soil types was studied using soil columns. The columns were filled with disturbed and undisturbed soils of either the Bagan Datoh soil (clay) or the Labu soil (sandy clay). The average total percentage of carbofuran in the leachate of the undisturbed Labu soil after 14 days of watering (80.8%) was approximately similar to that of the total amount from the disturbed soil (81.4%). However, carbofuran leaching was observed in the disturbed soil after the fourth day of watering whereas for the undisturbed soil, leaching occurred after the first watering. A similar trend was observed in the Bagan Datoh soil where the residue of carbofuran was detected after the first day of watering in the undisturbed soil column but only at the eighth day of watering in the disturbed soil column. The total percentage carbofuran in the leachate of disturbed and undisturbed soil columns from Bagan Datoh after 14 days of watering was 3.6% and 41.7%, respectively. The study showed that less leaching occurred in soil columns with high organic content such as the Bagan Datoh soil and especially so in disturbed soils where the organic matter was homogeneously mixed in all layers.
Other factors to consider in the formation of chloropropandiol fatty esters in oil processes

Ramli MR, Siew WL, Ibrahim NA, Kuntom A, Abd Razak RA

Food Addit Contam Part A Chem Anal Control Expo Risk Assess, 2015;32(6):817-24.
PMID: 25798697 DOI: 10.1080/19440049.2015.1032368

This paper examines the processing steps of extracting palm oil from fresh fruit bunches in a way that may impact on the formation of chloropropandiol fatty esters (3-MCPD esters), particularly during refining. Diacylglycerols (DAGs) do not appear to be a critical factor when crude palm oils are extracted from various qualities of fruit bunches. Highly hydrolysed oils, in spite of the high free fatty acid (FFA) contents, did not show exceptionally high DAGs, and the oils did not display a higher formation of 3-MCPD esters upon heat treatment. However, acidity measured in terms of pH appears to have a strong impact on 3-MCPD ester formation in the crude oil when heated at high temperatures. The differences in the extraction process of crude palm oil from current commercial processes and that from a modified experimental process showed clearly the effect of acidity of the oil on the formation of 3-MCPD esters. This paper concludes that the washing or dilution step in palm oil mills removes the acidity of the vegetative materials and that a well-optimised dilution/washing step in the extraction process will play an important role in reducing formation of 3-MCPD esters in crude palm oil upon further heat processing.
Verification and evaluation of monochloropropanediol (MCPD) esters and glycidyl esters in palm oil products of different regions in Malaysia

Abd Razak RA, Ahmad Tarmizi AH, Abdul Hammid AN, Kuntom A, Ismail IS, Sanny M

Food Addit Contam Part A Chem Anal Control Expo Risk Assess, 2019 Nov;36(11):1626-1636.
PMID: 31437078 DOI: 10.1080/19440049.2019.1654139

This study was conducted to investigate on the effect of different sampling regions of palm-refined oils and fats on the 2- and 3-monochloropropanediol fatty acid esters (MCPDE) and glycidol fatty acid esters (GE) levels. The American Oil Chemists' Society (AOCS) Official Method Cd 29a-13 on the determination of MCPDE and GE in edible oils and fats by acid transesterification was successfully verified and optimised, with slight modification using 7890A Agilent GC system equipped with 5975C quadrupole detector. The determined limits of detection (LOD) for MCPDE were 0.02 mg kg-1 and 0.05 mg kg-1 for GE. The method performance has showed good recovery between 80% and 120% for all pertinent compounds with seven replicates assayed in three separate days. Round robin test with two European laboratories, i.e. Eurofins and SGS, has shown compliance results with those of the present study. Among the sampling regions, only one refinery located in the central region of Malaysia showed a significant increment of the MCPDE and GE levels after refining process. The GE level averaging at 2.5 mg kg-1 was slightly higher than that of 3-MCPDE averaging at 1.3 mg kg-1. Both esters were preferentially partitioned into the liquid phase rather than the solid phase after fractionation. However, the overall results exhibited no direct correlation between the esters content and the different sampling locations of the palm oil products in Malaysia. Analysis of total chlorine content also displayed significant variations between sampling locations which clearly show its effect on the chlorine content in the CPO samples.
Fulltext Changes in oxidation indices and minor components of low free fatty acid and freshly extracted crude palm oils under two different storage conditions

Tan CH, Ariffin AA, Ghazali HM, Tan CP, Kuntom A, Choo AC

J Food Sci Technol, 2017 Jun;54(7):1757-1764.
PMID: 28720930 DOI: 10.1007/s13197-017-2569-9

This article reports on the changes of oxidation indices and minor components of low free fatty acid (FFA) and freshly extracted crude palm oils after storage at ambient (28 ± 1 C) and 60 C for 77 days. The changes in peroxide value (PV), FFA, extinction coefficient at 233 and 269 nm (K233 and K269), bleachability index (DOBI), carotene and vitamin E contents were monitored. PV, FFA, K233 and K269 of both oil samples increased as storage progressed while the values of carotene and vitamin E contents decreased. At the end of storage period at 60 °C, the carotene content of low FFA crude palm oil was 4.24 ppm. The storage conditions used led to the loss of entire vitamin E fractions of both oil samples as well as a reduction in DOBI values except for freshly extracted crude palm oil stored at ambient temperature.
Fulltext Preliminary Large Scale Mitigation of 3-Monochloropropane-1, 2-diol (3-MCPD) Esters and Glycidyl Esters in Palm Oil

Ramli MR, Tarmizi AHA, Hammid ANA, Razak RAA, Kuntom A, Lin SW, et al.

J Oleo Sci, 2020 Aug 06;69(8):815-824.
PMID: 32641608 DOI: 10.5650/jos.ess20021

Approximately 900 tonne of crude palm oil (CPO) underwent washing using 5 to 10% hot water (90 to 95°C) at a palm oil mill. The aim of the CPO washing was to eliminate and/or reduce total chlorine content present in the conventional CPO, as it is known as the main precursor for the formation of 3-monochloropropane-1, 2-diol esters (3-MCPDE). By a simple hot water washing, more than 85% of the total chlorine was removed. However, washing did not have significant (p > 0.05) effect on other oil quality parameters such as the deterioration of bleachability index (DOBI), free fatty acid (FFA) content and diacylglycerol (DAG) content of the oil. The latter has been established as the main precursor for glycidyl esters (GE) formation. The treated CPO was then transported using tankers and further refined at a commercial refinery. Refining of washed CPO resulted in significantly (p < 0.05) lower formation of 3-MCPDE, but GE content remained slightly high. Post-treatment of refined oil significantly reduced the GE content (p < 0.05) to an acceptable level whilst almost maintaining the low 3-MCPDE level. The study has proven that water washing of CPO prior to refining and subsequent post-refining is so far the most effective way to produce good quality refined oil with considerably low 3-MCPDE and GE contents. Dry fractionation of refined palm oil showed these contaminants partitioned more into the liquid olein fraction compared to the stearin fraction.