Food Control 149 (2023) 109699

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Food Control
journal homepage: www.elsevier.com/locate/foodcont

The effects of quality changes in vegetable oils on the formation and

absorption of monochloropropanediol esters (MCPDE) and glycidyl esters
(GE) during deep-frying of potato chips
Wei Ping Quek a, b, Yi Hui Ong b, c, Michelle Khai Khun Yap a, Yee Ying Lee a, b,
Nur Azwani Ab Karim d, Chien Lye Chew b, Eng-Seng Chan b, c, *
a
School of Science, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, 47500, Subang Jaya, Selangor, Malaysia
b
Monash-Industry Plant Oils Research Laboratory (MIPO), Monash University Malaysia, Jalan Lagoon Selatan, 47500, Bandar Sunway, Selangor, Malaysia
c
Chemical Engineering Discipline, School of Engineering, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, 47500, Subang Jaya, Selangor, Malaysia
d
Sime Darby Plantation Research (formerly known as Sime Darby Research), R&D Centre – Carey Island, Lot 2664 Jalan Pulau Carey, 42960, Pulau Carey, Selangor,
Malaysia

A R T I C L E I N F O A B S T R A C T

Keywords: Monochloropropanediol esters (MCPDE) and glycidyl esters (GE) are probably carcinogenic compounds found in
Vegetable oils refined vegetable oils and deep-fried foods. However, there was a lack of studies on the absorption of MCPDE and
Deep-frying GE by food system fried with different types of oils. In this study, four major types of vegetable oils, i.e. palm
Potato chips
olein (PO), canola (CNL), soybean (SBO), and sunflower oils (SFO) were used to fry potato chips for 40 cycles.
Oil absorption
3-Monochloropropane-1,2-diol esters
The potatoes were pre-soaked in 5% NaCl before frying. The 3-MCPDE contents in soft oils (CNL, SBO, SFO) were
Glycidyl esters found to increase across the frying cycles owing to the release of unsaturated FFA (lower pKa value) which was
likely to dissociate and increase the acidity of the oil. In contrast, the 3-MCPDE content in PO decreased with
frying cycles since saturated FFA (higher pKa value) has a less tendency to dissociate. After 40 frying cycles, the
3-MCPDE content in potato chips fried with PO (0.14 μg/g of chips) was found to be lower than CNL (0.25 μg/g
of chips) and SBO (0.17 μg/g of chips), but slightly higher than SFO (0.12 μg/g of chips). On the other hand, the
initial GE content in PO was found to be significantly higher (3.49 μg/g of oil) than the soft oils (≤0.1 μg/g). The
GE content in potato chips did not change significantly across the frying cycles regardless of the vegetable oil
used. In conclusion, the physicochemical properties of vegetable oil have been found to influence the 3-MCPDE
level in fried food and it is critical to produce frying oil with low initial levels of contaminants (especially GE) to
improve food safety.

Hajjul, 2020), giving rise to various undesirable compounds such as lipid

1. Introduction
Deep-frying is a popular method of cooking as it produces foods with
desired sensory characteristics such as savoury flavour, crispy texture
and golden brown colour. There are different types of vegetable oils
available in the market that can be used for deep-frying, e.g. palm olein
(PO), canola oil (CNL), soybean oil (SBO), sunflower oil (SFO), etc..
During deep-frying, the foods are partially or completely immersed in a
hot oil in the presence of oxygen. Intense bubbling occurs simulta­
neously due to the evaporation of water from the food system (Choe &
Min, 2007), which results in many complex chemical reactions including
hydrolysis, oxidation, and polymerisation (Asokapandian, Swamy, &
hydroperoxides, aldehydes and polymerised triacylglycerols. A consid­
erable amount of oil containing these compounds can be absorbed by the
food to replace the moisture lost during and after deep-frying (Anio­
łowska & Kita, 2015). Therefore, the quality of frying oil may eventually
reach a point where the deep-fried food is no longer safe for
consumption.
In addition, food processing contaminants such as 2-, 3-monochloro­
propanediol ester (2- and 3-MCPDE) and glycidyl ester (GE) can also
form during deep-frying (Wong et al., 2020). The 3-MCPDE and GE are
classified as possible and probably carcinogenic compounds, respec­
tively by the International Agency for Research on Cancer (IARC) after
the 3-MCPDE was reported to cause nephrotoxicity in rats while the GE

* Corresponding author. Monash-Industry Plant Oils Research Laboratory (MIPO), Monash University Malaysia, Jalan Lagoon Selatan, 47500, Bandar Sunway,
Selangor, Malaysia.
E-mail address: chan.eng.seng@monash.edu (E.-S. Chan).

https://doi.org/10.1016/j.foodcont.2023.109699
Received 16 September 2022; Received in revised form 2 February 2023; Accepted 19 February 2023
Available online 21 February 2023
0956-7135/© 2023 Elsevier Ltd. All rights reserved.
W.P. Quek et al.
Abbreviations
CNL Canola oil
DAG Diacylglycerol
FFA Free fatty acid
GE Glycidyl ester
MAG Monoacylglycerol
MCPDE Monochloropropanediol esters
MUFA Monounsaturated fatty acid
PO Palm olein
PUFA Polyunsaturated fatty acid
SFA Saturated fatty acid
SBO Soybean oil
SFO Sunflower oil
TAG Triacylglycerol
was found to increase the incidence of tumours in rat tissues via geno­
toxic mechanism (EFSA, 2016; Lampen, 2022; Scholz & Schilter, 2022;
Yang et al., 2020). As a result, the Joint FAO/WHO Expert Committee on
Food Additives (JECFA) has established a provisional maximum toler­
able daily intake (PMTDI) of 4 μg/kg body weight (bw) for 3-MCPDE to
avoid excessive dietary exposure (Joint FAO/WHO Expert Committee on
Food Additives, 2016). Since establishing a health-based guidance value
for substances that are both genotoxic and carcinogenic is not appro­
priate, the margin of exposure (MOE) approach is chosen for GE (Joint
FAO/WHO Expert Committee on Food Additives, 2016). The MOE was
calculated by dividing the reference point of 10.2 mg/kg bw per day
with the exposure level (mg/kg). An MOE of 25,000 or higher is
considered of low health concern (Joint FAO/WHO Expert Committee
on Food Additives, 2016). In addition, the European Commission has set
the maximum levels of 3-MCPDE permitted in soft oils (e.g. CNL, SBO,
SFO = 1.25 ppm) and other vegetable oils (e.g. PO = 2.5 ppm). For GE,
the maximum permissible level is 1 ppm for all refined vegetable oils
(EFSA, 2020).
Many studies have examined the formation of 3-MCPDE and GE in
different types of vegetable oils (i.e. PO, CNL, SBO, SFO, etc.) during
deep-frying (Abd Razak, Ahmad Tarmizi, Kuntom, Sanny, & Ismail,
2021; Ahmad Tarmizi, Abd Razak, Abdul Hammid, & Kuntom, 2019;
Ben Hammouda, Zribi, Ben Mansour, Matthäus, & Bouaziz, 2017; Wong,
Muhamad, et al., 2017; Xu et al., 2020). However, it is worth high­
lighting that these works have overlooked the absorption of decomposed
oil and toxic compounds (e.g. 3-MCPDE and GE) by the deep-fried foods.
There were also recent papers that studied the levels of MCPDE and GE
in food products across the frying cycles. For instance, Merkle, Oster­
meyer, Rohn, Karl, and Fritsche (2018) found increasing levels of 2- and
3-MCPDE, but a decreasing level of GE in salted fish fingers (0.16%,
1.5% NaCl) after frying with SFO over 7 h at 185 ◦ C. On the other hand,
Wong et al. (2020) performed frying of salted and non-salted potato
chips (0%, 1%, 3%, 5% NaCl) in PO at 180 ◦ C for 8.3 h over 5 days
without replenishing fresh oil. The researchers found that the 3-MCPDE
level decreases, but the GE level increases in all potato chips with
increasing frying duration. Hence, the mixed findings found between
previous studies could be attributed to the inconsistent experimental
protocols (i.e. type of food system, salt level, presence of antioxidants,
etc.), making it difficult to directly compare the contaminants levels in
the food frying using different types of vegetable oils.
To the best of our knowledge, there are still very limited works that
compare the absorption of MCPDE and GE by the foods frying with
different types of oils under standardised experimental conditions. Since
vegetable oil with different chemical composition degrades at different
rate, it is hypothesized that different degree of unsaturation of fatty
acids could influence the formation and absorption of MCPDE and GE
during deep-frying. Therefore, this research aimed to evaluate the
2
Food Control 149 (2023) 109699
quality changes of four major types of vegetable oils i.e. PO, CNL, SBO
and SFO on the formation and absorption of MCPDE and GE during
deep-frying of potato chips. These four types of oils were selected in this
study because they are the major vegetable oils produced globally, ac­
counting for up to 85% of world production of vegetable oils (Mielke,
2019; Pilorgé, 2020). In addition, a synthetic antioxidant, TBHQ, was
added into all types of oils at 200 ppm before deep-frying to standardise
the synthetic oxidant content in the cooking oils.
2. Materials and methods
2.1. Materials
Refined palm olein, canola oil, soybean oil, and sunflower oil
without antioxidants were supplied by local refineries. Fresh potatoes
(Russet var.) were purchased from a local supermarket (Mydin Whole­
sale Hypermarket, Selangor). F.A.M.E. Mix, C8-C24 was purchased from
Supelco (Dorset, UK). 1,2-dipalmitoyl-3-chloropropanediol, 1,2-dipal­
mitoyl-3-chloropropanediol-d5, 1,3-dipalmitoyl-2-chloropropanediol,
glycidyl palmitate, glycidyl palmitate-d5 were purchased from Lar­
odan (Solna, Sweden). Acetone and n-heptane of HPLC grades were
purchased from Merck (Darmstadt, Germany). All reagents and solvents
used were of analytical grade unless otherwise specified.
2.2. Deep-frying protocols
Briefly, 5 L of vegetable oil (PO, CNL, SBO, SFO) was poured into an
EF-102V Baker electric deep-fryer (ESM Machinery (KL) Sdn Bhd,
Malaysia) equipped with thermostat function and heated to 180 ◦ C ±
5 ◦ C. 200 ppm of TBHQ was added during heating to better represent the
commercial cooking oils. Fresh potatoes were peeled, sliced into a
thickness of 2 mm, and soaked in 5% salt water for 30 min. 5% of NaCl
concentration was chosen based on the experimental procedure
described in previous studies (Wong et al., 2020; Wong, Lai, et al., 2017;
Wong, Muhamad, et al., 2017). Once the oil reached set temperature,
200 g of sliced potatoes were blotted dried with paper towel before
adding into the oil and fried for 1.5 min. After the frying process, the
potato chips were taken out of the oil and let drained. The oil was heated
for 12 min to original temperature. Frying temperature was monitored
using 62 MAX + handheld infrared laser thermometer (Fluke Corpora­
tion, Washington, USA). The fryer was not covered during the whole
frying process. The frying step was repeated for 40 cycles (20 cycles per
day) and sampling was conducted at every 10th cycle. After the 20th
cycle, the fryer was switched off and covered by a lid and the remaining
20 cycles were continued the next day without oil replenishment. The
deep-fried oils were filtered through Whatman No. 1 filter paper to
remove suspended food particles and stored at − 20 ◦ C prior to being
analysed for their physicochemical properties and MCPDE and GE
levels.
2.3. Acylglycerol composition
The acylglycerol composition of fresh and deep-fried oils was
determined based on the carbon number following the method
described by (Chew et al., 2021). Around 0.05 g of oil sample was dis­
solved in 5 mL of n-hexane and injected into gas chromatography
(Model: Clarus 500; Perkin, Elmer, Waltham, Massachusetts, USA)
equipped with a flame ionization detector (GC-FID). The acylglycerols
were separated using a SP2380 (Supelco; Bellefonte, Pa., U.S.A.) capil­
lary column (0.25 cm i.d. × 30 cm × 0.2 μm). The temperature setting
was as follows: 120 ◦ C to 290 ◦ C for 25 ◦ C/min, then heated from 290 ◦ C
to 340 ◦ C for 10 ◦ C/min and from 340 ◦ C to 360 ◦ C for 15 ◦ C/min (hold
for 2 min). The injector and detector temperatures were set at 100 ◦ C
and 370 ◦ C. Nitrogen was used as a carrier gas at 45 mL/min. The in­
jection volume was 1 μL.
W.P. Quek et al.
2.4. Fatty acid composition
The preparation of fatty acid methyl ester (FAME) was based on
AOCS official method Ch 1-91 with some minor modifications. Oil
sample (200 mg) was weighed into a 15 mL centrifuge tube together
with 2 mL of toluene. 0.1 mL 2 M methanolic KOH was added for
transesterification. The tube was mixed by shaking vigorously for 30 s
and incubated for 1 h at 50 ◦ C, followed by centrifugation. The upper
layer containing FAME was extracted into a chromatography vial before
injecting into an Agilent GC-7890A gas chromatography equipped with
Flame Ionization Detector (GC-FID) (Agilent Technologies, USA). GC
operating conditions were based on European standard method –
EN14103, and separation was carried out using an HP-INNOWAX
capillary column (30 m × 0.25 mm I.D. × 0.25 μm film thickness)
(Agilent Technologies, USA). The FAMEs were identified by comparing
the retention time with commercial standards (F.A.M.E. Mix, C8-C24;
Supelco, Dorset, UK). The FAMEs were calculated based on the peak
areas and expressed as percentage of fatty acid.
2.5. Free fatty acid content
The free fatty acid (FFA) content in fresh and deep-fried oil samples
was determined based on AOCS method Ca 5a-40. In brief, the oil was
dissolved in neutralised isopropanol (99%) and phenolphthalein indi­
cator solution (1% in 99% isopropanol) followed by titrating against 0.1
M sodium hydroxide solution until the appearance of the first permanent
pink colour, of which can persist for 30 s.
2.6. Total chlorine content
Analysis of total chlorine content was performed using an Elemental
Analyzer, NSX-2100H (Mitsubishi Chemical Analytech, Japan). 50–60
mg of oil sample was first be combusted in argon and oxygen at 1000 ◦ C
and the resulting hydrogen chloride (HCl) gases were titrated against
silver ions generated coulometrically. The amount of chlorine (in ppm)
was calculated from the quantity of electricity required for the titration.
2.7. pH of water extract
The pH of fresh and deep-fried oils was measured using a pH meter to
determine their acidity. 30 g of oil was poured into a 50 mL centrifuge
tube containing 10 mL of ultra-pure water. The sample was vortexed for
2 min followed by centrifuging at 4500 rpm for 10 min. The aqueous
phase was transferred to a 15 mL centrifuge tube and the pH of water
extract was measured using a calibrated pH meter.
2.8. Contact angle
PO was pre-conditioned at 80 ◦ C for 20 min to melt any crystals
formed and then kept at 50 ◦ C until analysis. The soft oils were together
heated at 50 ◦ C before measurement. 5 μL of oil droplet was dispensed
onto a soda-lime glass slide using a micropipette and the baseline was
adjusted to measure the static contact angle using a ramé-hart goni­
ometer (ramé-hart Instrument Co., Succasunna, USA) at room temper­
ature. Soda-lime glass slide was chosen due to its hydrophilicity, making
the measurements feasible. The digital images and contact angles of oils
were processed and calculated using DropImage Advanced software.
2.9. Viscosity
The viscosity of fresh and deep-fried oils was measured using MCR
302 rheometer equipped with concentric cylinder systems (Anton Paar,
Austria). A stainless-steel stirrer was submerged into a stainless-steel cup
containing 20 g of oil and the force required to overcome the resistance
of the viscosity to the rotation was measured. The viscosity of oil was
determined at 180 ◦ C (frying temperature) under a constant shear rate of
3
Food Control 149 (2023) 109699
100 s− 1. A total of 20 data points were collected, and the viscosity (cP)
was obtained by averaging the 20 data points.
2.10. Moisture and oil contents of potato chips
Potato chips were dried at 90 ◦ C for 8 h and their moisture contents
were measured by the gravimetric method. The potato chips were finely
ground, and the oils were extracted via Soxhlet extraction with hexane
according to the AOAC method 920.39 (Romano, Giordano, Vitiello,
Grottaglie, & Musso, 2012). During the extraction process, the round
bottom flasks containing hexane were placed on top of hot water bath.
The hexane evaporated and condensed upon contacting with cold
running water. The solvent accumulated in the extraction chamber
(sample held in thimble) for 5–10 min and then siphoned back to the
boiling flask. The oils were extracted from potato chips by repeated
washing of hexane for 5 h. The dissolved oil was isolated by evaporating
the organic solvent with a rotary evaporator and then cooled in a
desiccator before weighing for extract percentage calculation.
2.11. 2- and 3-monochloropropanediol esters and glycidyl esters
The 2- and 3-MCPDE and GE contents of frying oils as well as the oils
extracted from potato chips were determined based on the AOCS official
method Cd 29a-13. Briefly, 100–110 mg of sample was measured and
spiked with 50 μL of mixed internal standard solution, 1,2-dipalmitoyl-
3-chloropropanediol-d5 (40 μg/mL) and glycidyl palmitate-d5 (50 μg/
mL). The solution was then added with 30 μL of sodium bromide in 5%
sulphuric acid, vigorously shaken and allowed to incubate at 50 ◦ C for
15 min. The process was terminated by the addition of 3 mL, 0.6% so­
dium hydrogen carbonate solution followed by 2 mL of n-heptane to
separate the oil from water phase. The upper phase (oil and analytes)
was isolated and evaporated under nitrogen stream for 15 min at 35 ◦ C.
Following that, 1.8 mL of sulphuric acid/methanol solution (1.8% v/v)
was added into sample and incubated at 40 ◦ C for 16 h. The reaction was
stopped by adding 0.5 mL of saturated sodium hydrogen carbonate so­
lution (9.6% w/v) and 2 mL of sodium sulphate solution (20% w/v). 2
mL of n-heptane was then added to the solution to allow separation of
two layers, and the lower phase were derivatized with phenylboronic
acid solution (PBA) in an ultrasonic bath for 5 min. Extraction of phe­
nylboronic derivatives of MCPDs and MBPDs was made by collecting the
upper layer upon mixing with 1 mL of n-heptane. The supernatant was
dried under nitrogen stream and reconstituted with 800 μL of n-heptane
before analysing with a 5975C gas chromatography-mass spectrometry
(GC–MS) (Agilent Technologies, USA) equipped with mass selective
detector.
Separation was performed on a capillary column HP-5MS (30 m ×
0.25 mm × 0.25 μm, Agilent Technologies, USA). Helium gas was used
as a carrier at the flow rate of 0.8 mL/min with sample injection of 1 μL
set at pulsed splitless mode. The detector and injection temperatures
were fixed at 150 and 250 ◦ C, respectively. The column was initially
programmed at 80 ◦ C and held constant for 1 min before heating to
170 ◦ C at a rate of 10 ◦ C/min. The column temperature was then
increased to 200 ◦ C at a rate of 3 ◦ C/min, followed by rapid heating to
300 ◦ C at a rate of 15 ◦ C/min. The heating was later held at 300 ◦ C for
15 min. Quantitative analysis was accomplished by examining the
quantifier ions of the following components: (1) derivatized 3-MCPD at
m/z 147, 196 and 198; (2) 2-MCPD at m/z 196 and 198; (3) 3-MCPD-d5
at m/z 150, 201 and 203; (4) 3-MBPD at m/z 147 and 240; and (5) 3-
MBPD-d5 at m/z 150 and 245. Good linearity was obtained in the
evaluated range for 2-MCPDE (0–14.41 mg/kg; R2 = 0.9994), 3-MCPDE
(0–14.35 mg/kg; R2 = 0.9997), and GE (0–32.44 mg/kg; R2 = 0.9988).
The limit of detection (LOD) and limit of quantifications (LOQ) of the
method were calculated as the analyte concentration with signal-to-
noise (S/N) ratio of 3 and 10, respectively. The S/N ratios were esti­
mated based on the peak heights of the identified ions. The LODs for 2-
MCPDE, 3-MCPDE and GE were 0.06 ppm, 0.04 ppm, and 0.25 ppm,
W.P. Quek et al. Food Control 149 (2023) 109699

respectively. The LOQs for 2- and 3-MCPDE were 0.10 ppm, whereas for Table 1
GE was 0.25 ppm. Changes of acylglycerol and fatty acid composition in four types of vegetable oils
during deep-frying.
2.12. Statistical analysis Chemical composition Frying PO (%) CNL SBO SFO
(%) cycle (%) (%) (%)
The experiments were conducted in duplicates. The one-way analysis Free fatty acid (FFA)/ 0 0.09 ± ND ND ND
of variance (ANOVA) combined with Tukey’s multiple range test was Monoacylglycerol 0.01A
used to determine the significant differences between the results. Pear­ (MAG) 20 0.10 ± 0.06 ± 0.01 ± 0.01 ±
0.03b,A 0.03ab 0.00a 0.00a
son correlation analysis was performed to determine the relationship
40 0.15 ± 0.11 ± 0.06 ± 0.06 ±
between the quality parameters and the MCPDE and GE levels present in 0.01c,A 0.01b 0.01a 0.01a
the frying oils and potato chips using IBM SPSS software (version 22.0).
The significance level was set at p < 0.05. Diacylglycerol (DAG) 0 5.84 ± 1.06 ± 1.06 ± 1.10 ±
0.04b,B 0.13a,A 0.01a,A 0.01a,A
3. Results and discussion 20 5.59 ± 1.26 ± 1.22 ± 1.23 ±
0.02b,A 0.03a,AB 0.02a,B 0.01a,B
40 5.75 ± 1.40 ± 1.28 ± 1.30 ±
3.1. Acylglycerol and fatty acid composition
0.04c,B 0.00b,B 0.02a,B 0.00a,C

The deterioration of frying oil could be caused by the moisture

Triacylglycerol (TAG) 0 94.07 98.94 98.94 98.91
released from the food system. The moisture released primarily hydro­
± 0.06a, ± 0.13b, ± 0.01b, ± 0.01b,
lyses the ester linkages of triacylglycerols and produces mono­ A B C C

acylglycerols, diacylglycerols, and free fatty acids (Choe & Min, 2007). 20 94.33 98.69 98.77 98.77
As shown in Table 1, 0.09% of FFA/MAG was found in refined PO and ± 0.05s, ± 0.06b, ± 0.01b, ± 0.01b,
B AB B B
none was detected in the soft oils. In addition, PO was also revealed with
40 94.12 98.51 98.67 98.64
a significantly higher initial DAG content (5.84%) compared to the soft ± 0.04a, ± 0.01b, ± 0.01c, ± 0.01c,
oils (1.06–1.10%). During deep-frying, the TAG content decreased while AB A A A

the FFA/MAG and DAG contents increased in the soft oils. However, the
DAG content in PO decreased after 20 frying cycles and then increased at Saturated fatty acid 0 44.93 6.36 ± 14.93 10.40
the end of frying period. The reduction of DAG content in PO could be (SFA) ± 0.31d, 0.04a,A ± 0.11c, ± 0.01b,
due to its conversion to GE. On the other hand, the higher amount of
A A A

polyunsaturated fatty acids (PUFA) found in the soft oils are more sol­ 20 45.47 6.60 ± 15.27 10.71
± 0.37d, 0.11a,A ± 0.20c, ± 0.01b,
uble in water (Choe & Min, 2007), and therefore the hydrolysis reaction A A B

was found to occur more intensively in the soft oils, indicating by a 40 45.74 6.63 ± 15.41 11.00
higher increment of partial acylglycerols content. ± 0.39d, 0.04a,A ± 0.14c, ± 0.02b,
A A C
Moreover, refined PO was found to contain a higher SFA and a lower
PUFA content compared to the soft oils. During deep-frying, the amount
of energy required to break the C-H covalent bond of unsaturated fatty Monounsaturated fatty 0 43.50 63.86 23.61 25.49
acids is relatively lower than the saturated ones (Choe & Min, 2007). acid (MUFA) ± 0.23c, ± 0.03d, ± 0.36a, ± 0.02b,
A A A A
Therefore, the PUFA content was found to reduce significantly in all 20 43.58 64.65 24.24 26.17
types of oils. A higher reduction of PUFA content was found in soft oils ± 0.16c, ± 0.03d, ± 0.36a, ± 0.06b,
(1.34–1.77%) as compared to PO (0.89%), indicating a higher resistance A B A B

against thermo-oxidation in PO. Since oil degradation normally takes 40 43.59 65.22 24.47 26.65
± 0.22c, ± 0.18d, ± 0.40a, ± 0.05b,
place in PUFA, the concentrations of SFA and MUFA were found to in­ A C A C
crease owing to the normalisation of FA peaks.

Polyunsaturated fatty 0 11.57 29.78 61.46 64.11

3.2. Free fatty acid content, total chlorine content, pH acid (PUFA) ± 0.08a, ± 0.01b, ± 0.24c, ± 0.01d,
B C B C

FFA is well-studied as a pro-oxidant during deep-frying, and there­ 20 10.95 28.75 60.49 63.11
fore its value is commonly used to monitor the quality of frying oil. As ± 0.21a, ± 0.14b, ± 0.17c, ± 0.06d,
AB B A B
shown in Fig. 1A, the FFA content was found to increase across frying in
40 10.67 28.14 60.11 62.35
all types of oils. PO was found to have a higher FFA content, followed by ± 0.17a, ± 0.14b, ± 0.26c, ± 0.03d,
CNL, SBO and SFO throughout the frying process. Unlike the PUFA A A A A

hydrolysed from SBO and SFO, the saturated and monounsaturated free
fatty acids released from PO and CNL were more oxidatively stable,
making them difficult to be degraded into other polar compounds.
Hence, increasing amount of FFA accumulated in PO and CNL over the
frying cycles. The findings are in agreement with Abd Razak et al.
(2021), who reported higher FFA level in PO (1.7%), followed by CNL
(0.98%), SBO (0.82%) and SFO (0.81%) after frying for 160 cycles.
Moreover, the dissolved salt was absorbed by the sliced potatoes via
osmosis during the immersion process. The sodium chloride could be
carried over by the diffusion of water from the chips into the frying oil.
In fact, chlorinated compounds are one of the main precursors of 2- and
3-MCPDE during deep-frying (Šmidrkal et al., 2016). The chloride ions
in frying oils could generate new MCPDE by interacting with the acyl­
glycerols via acyloxonium ions (Destaillats, Craft, Sandoz, & Nagy,
2012), which makes the examination of total chlorine content of oils
Mean values with different lowercase letters in the same row are significantly
different at p < 0.05 (comparison of the same parameter between different types
of oils), while different uppercase letters in the same column are significantly
different at p < 0.05 (comparison of the same parameter across different frying
cycles). Letter “a” or “A” represents lowest value; Letter “d” or “D” represents
highest value.
across the frying cycles important. As illustrated in Fig. 1B, the total
chlorine content increased significantly in all types of oils as frying
progressed. The level of chlorine in vegetable oils throughout the frying
experiment was found to be PO > CNL > SBO > SFO. A higher polarity in
PO attributed to higher FFA and DAG contents could potentially attract
more chloride ions into the frying oil, resulting in a higher total chlorine
content compared to the soft oils. Likewise, higher FFA content in CNL

4
W.P. Quek et al. Food Control 149 (2023) 109699

Fig. 1. FFA content (A), total chlorine content (B), and pH (C) of PO, CNL, SBO, and SFO over 40 frying cycles. Mean values with different lowercase letters across 40
frying cycles were significantly different at p < 0.05 (comparison within the same type of oil). Mean values with different uppercase letters at the same frying cycle
were significantly different at p < 0.05 (comparison between different types of oils).

had led to a higher total chlorine content than SBO and SFO.
In addition, not only organic acids (e.g. FFA) were found in vegetable
oils, inorganic acids such as hydrochloric acid (HCl) could also form
during deep-frying (Šmidrkal et al., 2016). These inorganic acids are
more water soluble than the organic acids with long carbon chain
length, and therefore they can easily dissociate hydrogen ions under
aqueous environment. The relative amount of free hydrogen ions, or oil
acidity, can then be measured using a pH meter. As depicted in Fig. 1C,
PO had a lower initial pH compared to the soft oils, which could be due
to the used of acidic bleaching earth during the refining process.
Furthermore, the pH of soft oils was found to reduce as the frying cycles
increased. This is probably because the PUFA hydrolysed from the soft
oils have lower pKa values (strong acids) (Pashkovskaya et al., 2018),
thus easier to dissociate and release hydrogen ions from the carboxyl
groups. The dissociated hydrogen ions can then react with sodium
chloride released from the potato chips to form HCl (Šmidrkal et al.,
2016), increasing the acidity of soft oils. Among them, CNL (by 0.71
unit) had the highest reduction of pH level, followed by SBO (by 0.53
unit) and SFO (by 0.49 unit), which could be owing to a higher linolenic
acid content. In contrast, the saturated palmitic acids released in PO are
difficult to be dissociated and form HCl (Kanicky & Shah, 2002), causing
the PO to become less acidic as the inorganic acids available in the PO
could be utilised to produce 2- or 3-MCPDE during deep-frying. At the
end of frying process, the lowest pH was observed in deep-fried CNL (pH

5
W.P. Quek et al.
4.85), followed by SBO and SFO (pH 4.95), and lastly PO (pH 5.23).
3.3. Contact angle and viscosity
The contact angle of the oil was measured to indicate its wettability
on a food surface after deep-frying. A lower oil contact angle indicates
more polar compounds or surfactant agents formed during deep-frying
(Aydar, Rodriguez-Martinez, & Farkas, 2016), which could increase
the adhesion of oil onto aqueous food surface, promoting oil absorption
after deep-frying (Rossi, Alamprese, Ratti, & Riva, 2009). Conversely, oil
with higher contact angle has lower affinity towards hydrophilic food
surface, thus easier to be shaken off from the food during draining.
Fig. 2A demonstrated that the contact angle of soft oils decreased
significantly but the contact angle of PO remained relatively stable over
40 frying cycles, which could be due to a lower oxidation rate across the
frying period. At the end of frying process, PO was found to have a
higher contact angle and lower wettability compared to the soft oils,
which could result in a lower oil absorption rate.
Additionally, the viscosity of oil is often measured to evaluate the
rate of oil uptake during deep-frying (Maskan, 2003). As illustrated in
Fig. 2B, the viscosity of all types of oils increased significantly after
Fig. 2. Contact angle (A) and viscosity (B) of PO, CNL, SBO and SFO over 40 frying cycles. Mean values with different lowercase letters across 40 frying cycles were
significantly different at p < 0.05. Mean values with different uppercase letters at the same frying cycle were significantly different at p < 0.05 (comparison between
different types of oils).
6
Food Control 149 (2023) 109699
frying for 40 cycles, potentially ascribed to the formation of high mo­
lecular weight oxidation compounds via polymerisation (Santos, Santos,
& Souza, 2005). The viscosity increment was found higher in SFO (by
0.34 cP), followed by SBO (by 0.2 cP), CNL (by 0.15 cP) and lastly PO
(by 0.14 cP), which could be corresponded to the rate of formation of
polymers during deep-frying.
3.4. Moisture and oil contents of potato chips
The increment in oil viscosity after prolonged deep-frying could
reduce the convective heat transfer from the frying oil to the food sur­
face (Miller, Singh, & Farkas, 1994; Tseng, Moreira, & Sun, 1996). As a
result, the moisture content of chips decreased drastically with
increasing number of cycles when frying with all types of vegetable oils
(see Fig. 3A). This is because lower heat transfer coefficient could reduce
the rate of formation and thickening of crust (Alvis, Vélez,
Rada-Mendoza, Villamiel, & Villada, 2009), allowing more steam,
especially those produces from the bound water, to be escaped from the
inner core of food matrix. Interestingly, more moisture was retained in
the chips deep-fried with PO compared to those deep-fried with the soft
oils, potentially due to the high inherent DAG content in PO (Gertz,
W.P. Quek et al.
Fig. 3. Moisture (A) and oil (B) contents of chips deep-fried with PO, CNL, SBO, and SFO over 40 frying cycles.
Klostermann, & Parkash Kochhar, 2003), which could facilitate heat
transfer to form a thicker and denser crust layer in a shorter time. The
crust layer could restrict the diffusion of water vapour from the core
region (Yamsaengsung & Moreira, 2002). In fact, crust also has a low
thermal conductivity which could influence the depth of heat penetra­
tion into the internal part of food system (Farid & Chen, 1998; Farkas,
Singh, & Rumsey, 1996). The higher moisture lost from the chips also
suggested that hydrolysis occurred more intensively in the soft oils than
the PO. Similar findings were reported by Rossi et al. (2009), of which
higher moisture loss was found in the chips frying with SFO compared to
PO.
Moreover, the evaporated water can be partially replaced by frying
oil in the food matrix (Southern, Chen, Farid, Howard, & Eyres, 2000).
When the foods are removed from the fryer, vacuum is created in the
internal cells due to the condensation of steam (Moreira, Sun, & Chen,
1997), which results in the decomposed oil adhering on the food surface
to be absorbed into the pores via capillary pressure. Therefore, the oil
content of chips usually increases as the moisture content decreases
during deep-frying. Fig. 3B suggested that the oil content extracted from
the chips frying in the soft oils increases with the number of frying cy­
cles, while it remained plateau throughout the period when frying using
PO. After 40 frying cycles, greater amount of oil had been absorbed by
the chips deep-fried with SBO (32.4%), followed by SFO (31.1%), CNL
7
Food Control 149 (2023) 109699
(30.9%) and lastly PO (26.4%). The current findings agree with Gamble,
Rice, and Selman (1987) and Southern et al. (2000), who demonstrated
that the oil absorption of chips is positively correlated to the amount of
moisture lost during deep-frying.
3.5. 2-, 3-monochloropropanediol esters and glycidyl esters
The formation of 2- and 3-MCPDE and GE in frying oil is a cause of
concern for food safety. As indicated in Table 2, the initial levels of 2-
and 3-MCPDE were found higher in PO than the soft oils due to a higher
inherent DAG content (see Table 1). However, the 2- and 3-MCPDE
levels reduced significantly in PO, while increased significantly in
CNL, SBO and SFO across the frying cycles. This could be attributed to
the release of unsaturated FFA in the soft oils which could dissociate
more readily than the saturated FFA found in PO (Choe & Min, 2007).
The dissociated hydrogen ions could react with the chloride ions from
salt, producing HCl (Šmidrkal et al., 2016) and thereby reducing the pH
of soft oils. Under an acidic condition, the carbonyl group of MAG
and/or DAG can easily abstract a hydrogen atom from the HCl to form an
intermediate acyloxonium ion, followed by nucleophilic substitution of
chloride ion to produce 2- or 3-MCPDE (Rahn & Yaylayan, 2011). The
significant negative correlations found between pH and MCPDE levels
were supported by previous studies which revealed that a higher oil
W.P. Quek et al. Food Control 149 (2023) 109699

Table 2
Changes of MCPDE and GE contents in four types of vegetable oils and the potato chips frying using the corresponding oils.
Oil Frying 2-MCPDE 3-MCPDE GE
type cycle
μg/g of oil μg/g of oil in μg/g of chips μg/g of oil μg/g of oil in μg/g of chips μg/g of oil μg/g of oil in μg/g of
chips chips chips chips

PO 0 1.25 ± ND ND 2.63 ± ND ND 3.49 ± ND ND

0.19f 0.01k 0.065c
10 0.97 ± 0.91 ± 0.01g 0.24 ± 0.002g 1.63 ± 1.41 ± 0.15f 0.37 ± 0.038j 2.98 ± 2.66 ± 0.123b 0.69 ±
0.03e 0.01j 0.132b 0.032b
20 0.91 ± 0.75 ± 0.03f 0.19 ± 0.007f 1.08 ± 0.85 ± 0.05d 0.21 ± 2.86 ± 2.61 ± 0.310b 0.66 ±
0.07e 0.07i 0.014gh 0.200b 0.078b
30 0.78 ± 0.90 ± 0.04g 0.23 ± 0.010g 0.83 ± 1.06 ± 0.07e 0.27 ± 0.019i 2.90 ± 2.64 ± 0.455b 0.67 ±
0.03de 0.02h 0.184b 0.116b
40 0.64 ± 0.56 ± 0.05e 0.15 ± 0.014e 0.56 ± 0.54 ± 0.03c 0.14 ± 2.75 ± 2.30 ± 0.158b 0.61 ±
0.01d 0.01f 0.007ef 0.033b 0.042b

CNL 0 0.03 ± ND ND 0.01 ± ND ND 0.02 ± ND ND

0.00a 0.00a 0.001a
10 0.06 ± 0.06 ± 0.01ab 0.02 ± 0.50 ± 0.53 ± 0.02c 0.15 ± 0.10 ± 0.09 ± 0.000a 0.03 ±
0.02a 0.003abc 0.03f 0.007ef 0.046a 0.000a
20 0.15 ± 0.16 ± 0.01c 0.05 ± 0.003c 0.70 ± 0.78 ± 0.01d 0.22 ± 0.15 ± 0.13 ± 0.009a 0.04 ±
0.01ab 0.01g 0.002h 0.005a 0.002a
30 0.28 ± 0.26 ± 0.01d 0.08 ± 0.003d 0.87 ± 0.91 ± 0.01de 0.28 ± 0.002i 0.17 ± 0.15 ± 0.008a 0.05 ±
0.02bc 0.03h 0.001a 0.002a
40 0.35 ± 0.30 ± 0.02d 0.09 ± 0.006d 0.85 ± 0.81 ± 0.01d 0.25 ± 0.19 ± 0.13 ± 0.005a 0.04 ±
0.04c 0.05h 0.002hi 0.023a 0.001a

SBO 0 0.01 ± ND ND 0.06 ± ND ND 0.10 ± ND ND

0.00a 0.00a 0.002a
a a a
10 0.02 ± 0.01 ± 0.00 0.004 ± 0.10 ± 0.14 ± 0.03 0.04 ± 0.11 ± 0.10 ± 0.005 0.03 ±
0.01a 0.001a 0.01ab 0.008a 0.002a 0.001a
20 0.03 ± 0.02 ± 0.00a 0.005 ± 0.20 ± 0.27 ± 0.01ab 0.08 ± 0.11 ± 0.10 ± 0.002a 0.03 ±
0.01a 0.001ab 0.02bc 0.002bc 0.003a 0.001a
30 0.07 ± 0.06 ± 0.01ab 0.02 ± 0.37 ± 0.41 ± 0.02bc 0.13 ± 0.12 ± 0.13 ± 0.011a 0.04 ±
0.00a 0.003abc 0.02e 0.005de 0.007a 0.003a
40 0.12 ± 0.10 ± 0.01bc 0.03 ± 0.55 ± 0.54 ± 0.01c 0.17 ± 0.11 ± 0.12 ± 0.003a 0.04 ±
0.01ab 0.002bc 0.01f 0.004fg 0.006a 0.001a

SFO 0 0.10 ± ND ND 0.27 ± ND ND 0.01 ± ND ND

0.00ab 0.01cd 0.000a
abc ab a
10 0.12 ± 0.09 ± 0.01 0.02 ± 0.30 ± 0.28 ± 0.02 0.07 ± 0.02 ± 0.03 ± 0.002 0.01 ±
0.01ab 0.002abc 0.02de 0.004ab 0.002a 0.000a
abc ab a
20 0.10 ± 0.09 ± 0.01 0.02 ± 0.23 ± 0.29 ± 0.01 0.08 ± 0.02 ± 0.04 ± 0.003 0.01 ±
0.01ab 0.002abc 0.01cd 0.004bc 0.003a 0.001a
30 0.11 ± 0.10 ± 0.01bc 0.03 ± 0.33 ± 0.34 ± 0.01b 0.10 ± 0.05 ± 0.07 ± 0.001a 0.02 ±
0.01ab 0.002bc 0.02de 0.004bcd 0.006a 0.000a
40 0.12 ± 0.14 ± 0.01bc 0.04 ± 0.003c 0.33 ± 0.38 ± 0.02bc 0.12 ± 0.06 ± 0.10 ± 0.002a 0.03 ±
0.01ab 0.02de 0.006cde 0.003a 0.001a

Data are expressed as the mean ± standard deviation, where different lowercase letters in the same column are significantly different at p < 0.05 (comparison between
different types of oils over 40 frying cycles). Letter “a” to “k” represents increasing concentration. LOD 2-MCPDE = 0.06 mg/kg, LOQ 2-MCPDE = 0.10 mg/kg; LOD 3-MCPDE
= 0.04 mg/kg, LOQ 3-MCPDE = 0.10 mg/kg; LOD GE = 0.25 mg/kg, LOQ GE = 0.25 mg/kg.

acidity could promote the formation of 3-MCPDE (Freudenstein, Wek­
ing, & Matthäus, 2013; Li et al., 2016). As the rate of FFA dissociation is
dependent upon the number of double bonds, CNL with a higher initial
linolenic acid composition (9.53% vs 6.67% in SBO and 0.13% in SFO)
was found with a higher formation rate of MCPDE among the soft oils
during deep-frying. Another possible reason is the higher increment of
DAG precursor in CNL across the frying cycles. The results explained the
significant correlations (p < 0.01) established between DAG, MAG, FFA
and the total chlorine contents to that of 2- and 3-MCPDE levels in the
soft oils (see Table 3). Similar trend was observed by Xu et al. (2020), of
which the 3-MCPDE content in CNL, high-oleic CNL and high-oleic SFO
increased after 72 h of frying with frozen fish nuggets. Higher increment
of 3-MCPDE level was seen in CNL, followed by high-oleic CNL and
high-oleic SFO. On the contrary, Abd Razak et al. (2021) revealed that
the concentration of 3-MCPDE in PO, CNL, SBO, and SFO reduced
significantly across the frying duration, which could be due to lower salt
and moisture contents in the pre-fried French fries used.
Interestingly, the 2- and 3-MCPDE levels in PO were found to
decrease over the frying cycles although the amount of chlorine and FFA
found in PO were significantly higher than the soft oils, potentially
ascribed to the majority of FFA released in PO are saturated (higher pKa
value) and thus have a less tendency to dissociate and form HCl pre­
cursor (Kanicky & Shah, 2002; Pashkovskaya et al., 2018; Šmidrkal
et al., 2016). Therefore, the decomposition rate of the contaminants was
higher than the formation rate. The reported degradation trend of
MCPDE in PO is in agreement with (Abd Razak et al., 2021; Wong,
Muhamad, et al., 2017). Although PO contained a significantly higher
initial 3-MCPDE content (2.63 ppm) than the soft oils, it was found to
reduce to 0.56 ppm after 40 frying cycles which is comparable with the
soft oils (0.33–0.85 ppm).
Additionally, it was revealed that the PO had a higher initial GE
content than the soft oils before deep-frying, which could be attributed
to a higher level of DAG precursor in crude palm oil (CPO) during
refining (Destaillats et al., 2012). Nevertheless, the presence of reactive
epoxide group in GE reduces its thermal stability during deep-frying
(Cheng, Liu, Guo, Chen, & Cheng, 2020), not to mention it also allows
the nucleophilic substitution of chloride ion to convert to 2- or 3-MCPDE
(Rahn & Yaylayan, 2011). Thus, significant negative correlation was

8
W.P. Quek et al. Food Control 149 (2023) 109699

Table 3 applying a lower deodorisation temperature (200 ◦ C) during refining

Pearson correlation analysis between the oil quality parameters and the MCPDE compared to the normal deodorisation temperature of 260 ◦ C (Matthäus
and GE levels in deep-fried oils and chips. & Pudel, 2013).
PO Soft Oils (CNL, SBO, SFO)

2- 3- GE 2- 3- GE 4. Conclusion
MCPDE MCPDE MCPDE MCPDE

TAG − .246 − .446 − .538 ¡.839a ¡.818a − .660

The physicochemical changes in different types of vegetable oils
DAG .416 .600 .681 .818a .806a .624 were found to influence the formation and absorption of MCPDE under a
FFA/MAG − .907 − .798 − .730 .888a .816a .701b standardised deep-frying protocol. The 2- and 3-MCPDE contents were
SFA − .992 − .996 − .981 − .501 − .343 − .054 found to decrease in PO across the frying cycles, which could be due to
MUFA − .937 − .990 ¡.999b .502 .449 .404
the release of saturated FFA which have a lesser tendency to dissociate
PUFA .989 .998b .985 − .485 − .457 − .469
FFA ¡.956a ¡.911b − .799 .763a .839a .599b and react with the chloride ions to form HCl. Conversely, soft oils
Total ¡.965a ¡.978a ¡.892b .725a .788a .659a released more unsaturated FFA that were found to increase oil acidity,
chlorine thus promoting the formation of MCPDE. Despite a higher initial 3-
pH ¡.999b − .984 − .960 ¡.728b ¡.810a − .543
MCPDE content in PO, the 3-MCPDE content in potato chips fried with
2- 3- GE 2- 3- GE PO (0.14 μg/g of chips) after 40 frying cycles was found to be lower than
MCPDE MCPDE (chips) MCPDE MCPDE (chips) CNL (0.25 μg/g of chips) and SBO (0.17 μg/g of chips), but slightly
(chips) (chips) (chips) (chips)
higher than SFO (0.12 μg/g of chips). On the other hand, the initial GE
Oil − .291 − .081 − .435 .421 .533 .736a content in PO was found to be significantly higher (3.49 μg/g of oil) than
content
the soft oils (≤0.1 μg/g). After 40 frying cycles, the GE content in potato
of chips
Moisture .901 .961b .968b − .302 − .413 − .549 chips fried with PO showed a small reduction from 0.69 μg/g of chips to
content 0.61 μg/g of chips whereas the GE content in soft oils increased
of chips marginally but ≤0.05 μg/g of chips. In conclusion, it is crucial to pro­
2-MCPDE .710 .781 .878 .974a .827a .433 duce vegetable oil with low initial levels of MCPDE and GE to improve
(oil)
a a food safety.
3-MCPDE .730 .883 .848 .907 .987 .689a
(oil)
GE (oil) .963b .980b .985b .632b .773a .908a CRediT authorship contribution statement
a
Correlation is significant at the 0.01 level (2-tailed).
b
Correlation is significant at the 0.05 level (2-tailed). Wei Ping Quek: Conceptualization, Methodology, Formal analysis,
Data curation, Investigation, Writing – original draft, Writing – review &
observed between total chlorine content and GE level in PO. As a result, editing, Project administration, Validation. Yi Hui Ong: Investigation,
the GE content was reduced in PO while levelling off in the soft oils Analytical Support. Michelle Khai Khun Yap: Conceptualization, Su­
throughout the frying cycles. The results are consistent with literature pervision, Writing – review & editing. Yee Ying Lee: Conceptualization,
findings (Merkle et al., 2018; Wong, Lai, et al., 2017; Xu et al., 2020). Supervision, Writing – review & editing. Nur Azwani Ab Karim:
Despite the decreasing trend, PO was found with a significantly higher Investigation. Chien Lye Chew: Validation. Eng-Seng Chan: Concep­
level of GE than the soft oils across frying. tualization, Methodology, Validation, Supervision, Writing – original
Since a substantial amount of oil was absorbed by the chips during draft, Writing – review & editing, Funding acquisition.
deep-frying, it is worth to examine if the contaminants have been carried
over into the food. The contaminants levels (μg) found in the chips were Declaration of competing interest
normalised with the amount of oil extracted from the chips (g) and the
mass of chips (g), respectively (see Table 2). It was found that the con­ The authors declare that they have no known competing financial
centration of 2- and 3-MCPDE decreased in the chips deep-fried with PO interests or personal relationships that could have appeared to influence
whilst increased in the chips deep-fried with the soft oils across the the work reported in this paper.
frying cycles. However, the GE content remained statistically unchanged
(p > 0.05) in the chips fried with all types of oils. In addition, significant Data availability
positive correlations were found between the contaminants levels pre­
sent in the frying oils and the chips (see Table 3), which shows that mass Data will be made available on request.
transfer of MCPDE and GE could occur between the frying oil and the oil
absorbed by the chips until an equilibrium concentration is reached.
Acknowledgement
Although the concentrations of 3-MCPDE were higher in the chips
deep-fried with PO during the initial stage of frying, prolonging the
The authors are grateful to the support from the Monash School of
duration of frying had caused a significant reduction in the contami­
Science, Monash School of Engineering, and Monash-Industry Plant Oils
nants level. This is particularly beneficial to PO for commercial use
Research Laboratory.
because the oil could be used continuously or repetitively. In fact, at the
40th frying cycle, the 3-MCPDE level in the chips deep-fried using PO
Appendix A. Supplementary data
(0.14 ppm) is lower than those frying with SBO (0.17 ppm) and CNL
(0.25 ppm). Furthermore, it is worth noting that the GE level of chips
Supplementary data to this article can be found online at https://doi.
fried with PO was high, which is due to the higher initial GE concen­
org/10.1016/j.foodcont.2023.109699.
tration found in refined PO. Since GE may not decompose as effectively
as 3-MCPDE during deep-frying, it is crucial to reduce the initial GE
content in PO to the greatest extent. One of the ways is to reduce the References
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