Oxidation and Polymerization of Triacylglycerols: In-Depth Investigations towards the Impact of Heating Profiles
Abstract
:1. Introduction
2. Materials and Methods
2.1. Chemicals
2.2. Materials
2.3. Samples
2.4. Determination of Epoxy, Keto, and Hydroxy Fatty Acids
2.4.1. Transesterification
2.4.2. Isolation of Polar FAMEs
2.4.3. Hydrogenation
2.4.4. Gas Chromatography
2.5. Determination of Polymerized Triacylglycerols
2.5.1. Isolation of Total Polar Compound
2.5.2. High-Performance Size-Exclusion Chromatography (HPSEC)
2.6. Determination of Oxidative Stability
Peroxide Value (PV), p-Anisidine Value (AV), and Total Oxidation (TOTOX) Value
2.7. Determination of Fatty Acid Composition
2.7.1. Derivatization
2.7.2. Gas Chromatography
2.8. Statistical Analysis
3. Results and Discussion
3.1. Effect of Temperature and Heating Time on the Formation of Monomeric Oxidized Triacylglycerols
3.2. Effect of Temperature and Heating Time on the Total Polar Content (TPC)
3.3. Effect of Temperature and Heating Time on the Formation of Polymerized Triacylglycerols
3.4. Effect of Temperature and Heating Time on the Oxidative Stability of RBDPO
3.5. Effect of Temperature and Heating Time on the Fatty Acid Composition of RBDPO
3.6. Correlation among Analytical Parameters
4. Conclusions
Author Contributions
Funding
Conflicts of Interest
References
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Heating Temperature (°C) | Heating Time (h) | EpoxyFAMEs | KetoFAMEs | HydroxyFAMEs | Total |
---|---|---|---|---|---|
Fresh oil | 0 | 0.00 ± 0.00 a | 0.00 ± 0.00 a | 0.00 ± 0.00 a | 0.00 ± 0.00 a |
160 | 4 | 0.05 ± 0.00 ab | 0.05 ± 0.01 ab | 0.13 ± 0.01 bc | 0.23 ± 0.05 ab |
8 | 0.11 ± 0.01 abc | 0.08 ± 0.02 ab | 0.19 ± 0.02 bcd | 0.39 ± 0.06 bcdef | |
12 | 0.17 ± 0.02 cde | 0.12 ± 0.03 abc | 0.21 ± 0.07 bcde | 0.51 ± 0.05 bcdefg | |
16 | 0.27 ± 0.01 ef | 0.20 ± 0.03 bcde | 0.29 ± 0.02 def | 0.75 ± 0.05 fghi | |
20 | 0.36 ± 0.03 fgh | 0.21 ± 0.06 bcde | 0.27 ± 0.04 def | 0.83 ± 0.07 ghi | |
24 | 0.42 ± 0.07 gh | 0.21 ± 0.08 bcde | 0.25 ± 0.08 cdef | 0.88 ± 0.11 hi | |
170 | 4 | 0.13 ± 0.01bcd | 0.05 ± 0.01ab | 0.13 ± 0.01bc | 0.31 ± 0.05abcd |
8 | 0.18 ± 0.03 cde | 0.11 ± 0.03 ab | 0.18 ± 0.03 bcd | 0.46 ± 0.04 bcdef | |
12 | 0.24 ± 0.03 def | 0.18 ± 0.02 bcd | 0.23 ± 0.02 bcdef | 0.66 ± 0.03 defgh | |
16 | 0.32 ± 0.10 fg | 0.28 ± 0.13 cdef | 0.29 ± 0.08 def | 0.90 ± 0.02 hi | |
20 | 0.31 ± 0.09 fg | 0.29 ± 0.10 def | 0.28 ± 0.07 def | 0.88 ± 0.01 hi | |
24 | 0.36 ± 0.06 fgh | 0.35 ± 0.08 ef | 0.32 ± 0.05 ef | 1.03 ± 0.02 i | |
180 | 4 | 0.09 ± 0.00 abc | 0.08 ± 0.01 ab | 0.10 ± 0.00 ab | 0.27 ± 0.01 abc |
8 | 0.17 ± 0.02 cde | 0.08 ± 0.03 ab | 0.10 ± 0.02 ab | 0.36 ± 0.05 abcde | |
12 | 0.27 ± 0.02 ef | 0.17 ± 0.06 bcd | 0.17 ± 0.04 bcd | 0.61 ± 0.06 cdefgh | |
16 | 0.33 ± 0.02 fg | 0.19 ± 0.08 bcde | 0.19 ± 0.06 bcd | 0.71 ± 0.08 efghi | |
20 | 0.46 ± 0.06 h | 0.31 ± 0.06 def | 0.28 ± 0.04 def | 1.05 ± 0.16 i | |
24 | 0.73 ± 0.05 i | 0.42 ± 0.12 f | 0.35 ± 0.09 f | 1.50 ± 0.25 j |
Heating Temperature (°C) | Heating Time (h) | Polar Fraction Content (%, g 100 g−1) | Polar Fraction Composition (%, g 100 g−1) | ||||
---|---|---|---|---|---|---|---|
TAG Oligomers | TAG Dimers | Oxidized TAG Monomers | Diacylglycerols | Free Fatty Acids | |||
Fresh oil | 0 | 8.38 ± 0.53 a | 0.00 ± 0.00 a | 0.27 ± 0.05 a | 1.21 ± 0.05 a | 6.54 ± 0.59 a | 0.35 ± 0.11 c |
160 | 4 | 10.85 ± 0.42 ab | 0.25 ± 0.06 a | 1.67 ± 0.17 ab | 2.49 ± 0.28 ab | 6.17 ± 0.65 a | 0.27 ± 0.04 bc |
8 | 13.47 ± 0.45 bc | 0.75 ± 0.04 ab | 2.73 ± 0.19 bcd | 3.53 ± 0.17 bcd | 6.23 ± 0.22 a | 0.24 ± 0.04 bc | |
12 | 16.00 ± 1.31 cd | 1.34 ± 0.15 abcd | 3.65 ± 0.33 de | 4.91 ± 0.33 de | 5.91 ± 0.79 a | 0.19 ± 0.03 abc | |
16 | 19.15 ± 0.28 de | 1.98 ± 0.06 bcde | 4.80 ± 0.11 ef | 6.05 ± 0.25 ef | 6.15 ± 0.15 a | 0.18 ± 0.07 abc | |
20 | 22.11 ± 0.41 efg | 2.76 ± 0.22 defg | 5.75 ± 0.11 fgh | 7.43 ± 0.18 fg | 6.08 ± 0.15 a | 0.09 ± 0.10 ab | |
24 | 25.05 ± 0.30 fghi | 3.64 ± 0.30 fg | 6.63 ± 0.06 ghi | 8.61 ± 0.24 gh | 6.05 ± 0.27 a | 0.13 ± 0.15 abc | |
170 | 4 | 12.04 ± 0.57 abc | 0.42 ± 0.24 a | 1.98 ± 0.36 abc | 3.10 ± 0.24 abcd | 6.27 ± 0.47 a | 0.25 ± 0.05 bc |
8 | 15.95 ± 1.20 cd | 1.25 ± 0.31 abc | 3.43 ± 0.59 cde | 4.80 ± 0.44 cde | 6.24 ± 0.38 a | 0.22 ± 0.15 abc | |
12 | 19.95 ± 2.09 de | 2.04 ± 0.47 bcde | 4.81 ± 0.79 ef | 6.68 ± 1.04 efg | 6.23 ± 0.31 a | 0.19 ± 0.07 abc | |
16 | 23.36 ± 2.56 efgh | 2.84 ± 0.64 efg | 5.99 ± 1.07 fgh | 8.02 ± 1.09 fgh | 6.37 ± 0.09 a | 0.14 ± 0.11 abc | |
20 | 27.46 ± 3.33 hij | 4.19 ± 1.02 gh | 7.09 ± 1.21 hi | 9.90 ± 1.25 hi | 6.21 ± 0.11 a | 0.06 ± 0.12 ab | |
24 | 30.35 ± 3.21 jk | 5.40 ± 0.86 hi | 7.89 ± 1.08 ij | 10.96 ± 1.42 i | 6.10 ± 0.17 a | 0.00 ± 0.00 a | |
180 | 4 | 12.14 ± 1.22 abc | 0.46 ± 0.20 a | 2.42 ± 0.53 bcd | 2.86 ± 0.52 abc | 6.19 ± 0.12 a | 0.21 ± 0.09 abc |
8 | 15.92 ± 1.68 cd | 1.44 ± 0.09 abcde | 3.84 ± 0.69 de | 4.84 ± 0.68 cde | 5.68 ± 0.68 a | 0.13 ± 0.02 abc | |
12 | 21.19 ± 1.96 ef | 2.68 ± 0.60 cdef | 5.45 ± 0.71 fg | 6.81 ± 0.96 efg | 6.16 ± 0.38 a | 0.09 ± 0.10 ab | |
16 | 25.87 ± 2.37 ghij | 3.84 ± 0.79 fg | 6.95 ± 0.58 ghi | 8.65 ± 1.37 gh | 6.19 ± 0.38 a | 0.24 ± 0.06 bc | |
20 | 29.25 ± 2.12 ijk | 5.30 ± 0.80 hi | 7.82 ± 0.73 ij | 9.93 ± 0.89 hi | 6.20 ± 0.35 a | 0.00 ± 0.00 a | |
24 | 32.92 ± 1.96 k | 6.74 ± 1.27 i | 8.91 ± 0.43 j | 11.18 ± 0.95 i | 6.08 ± 0.55 a | 0.00 ± 0.00 a |
Heating Temperature (° C) | Heating Time (h) | Peroxide Value (meq O2/kg) | Anisidine Value | TOTOX Value |
---|---|---|---|---|
Fresh oil | 0 | 1.40 ± 0.22 a | 2.20 ± 0.64 a | 5.00 ± 0.96 a |
160 | 4 | 8.12 ± 1.89 bc | 38.87 ± 1.08 b | 55.10 ± 4.84 bc |
8 | 7.00 ± 1.48 bc | 53.82 ± 6.07 cde | 67.81 ± 5.40 cdef | |
12 | 8.12 ± 3.68 bc | 58.57 ± 5.44 cdef | 74.82 ± 3.01 defg | |
16 | 6.75 ± 1.19 bc | 66.53 ± 4.59 efg | 80.02 ± 5.52 fghi | |
20 | 6.87 ± 1.38 bc | 67.44 ± 5.72 efg | 81.18 ± 4.01 ghi | |
24 | 6.13 ± 1.97 b | 70.44 ± 7.65 fgh | 82.69 ± 6.63 ghi | |
170 | 4 | 8.75 ± 2.96 bc | 34.01 ± 3.88 b | 51.50 ± 4.29 b |
8 | 7.87 ± 1.89 bc | 47.79 ± 5.07 bcd | 63.52 ± 4.76 bcd | |
12 | 7.50 ± 0.58 bc | 64.32 ± 13.25 efg | 79.31 ± 12.18 fgh | |
16 | 7.87 ± 0.75 bc | 58.83 ± 6.75 def | 74.58 ± 7.45 defg | |
20 | 8.62 ± 0.74 bc | 68.83 ± 1.37 fg | 86.07 ± 1.67 ghi | |
24 | 7.25 ± 0.65 bc | 76.07 ± 8.87 gh | 90.56 ± 7.58 hij | |
180 | 4 | 10.10 ± 0.47 c | 44.64 ± 2.68 bc | 64.84 ± 3.07 cde |
8 | 9.74 ± 0.30 bc | 58.36 ± 2.99 cdef | 77.83 ± 3.08 efgh | |
12 | 9.61 ± 0.31 bc | 73.74 ± 0.68 gh | 92.96 ± 0.87 ij | |
16 | 8.36 ± 0.25 bc | 84.24 ± 0.74 hi | 100.95 ± 0.53 jk | |
20 | 7.99 ± 0.36 bc | 93.62 ± 2.43 i | 109.59 ± 2.45 k | |
24 | 7.49 ± 0.58 bc | 96.33 ± 2.48 i | 111.31 ± 3.07 k |
Heating Temperature (°C) | Heating Time (h) | Fatty Acid Composition (Relative Percentages) | C8 (ppm) | |||||||
---|---|---|---|---|---|---|---|---|---|---|
C12:0 | C14:0 | C16:0 | C18:0 | C18:1 | C18:2 | C18:3 | C18:2/C16:0 | |||
Fresh oil | 0 | 0.24 ± 0.00 a | 1.53 ± 0.04c | 39.80 ± 0.01 a | 4.19 ± 0.00 a | 43.90 ± 0.05 b | 10.33 ± 0.01 cde | N.D. | 0.26 ± 0.00 i | 0.00 ± 0.00 a |
160 | 4 | 0.21 ± 0.02 a | 1.03 ± 0.07 ab | 41.43 ± 0.62 a | 7.69 ± 0.82 ab | 39.21 ± 1.42 ab | 10.43 ± 0.73 cde | N.D. | 0.25 ± 0.0 hi | 0.00 ± 0.00 a |
8 | 0.22 ± 0.01 a | 0.98 ± 0.05 ab | 41.40 ± 0.93 a | 9.92 ± 0.10 bc | 38.14 ± 1.53 ab | 9.26 ± 0.50 bcde | N.D. | 0.22 ± 0.01 fghi | 2.84 ± 0.50 ab | |
12 | 0.23 ± 0.01 a | 1.02 ± 0.05 ab | 41.88 ± 1.77 a | 9.82 ± 0.24 bc | 38.20 ± 1.31 ab | 8.76 ± 0.51 bcde | N.D. | 0.21 ± 0.02 defghi | 4.83 ± 0.43 abcd | |
16 | 0.23 ± 0.02 a | 1.10 ± 0.22 ab | 42.08 ± 3.41 a | 11.58 ± 0.87 c | 36.87 ± 3.07 ab | 8.02 ± 1.05 abcd | N.D. | 0.19 ± 0.04 bcdefg | 5.78 ± 0.32 bcd | |
20 | 0.23 ± 0.02 a | 1.02 ± 0.04 ab | 42.98 ± 0.81 a | 12.48 ± 0.74 c | 35.27 ± 1.14 ab | 7.89 ± 0.44 abc | N.D. | 0.18 ± 0.01 bcdef | 7.07 ± 0.56 bcd | |
24 | 0.23 ± 0.01 a | 1.08 ± 0.11 ab | 45.84 ± 4.31 a | 12.53 ± 0.96 c | 33.14 ± 3.92 a | 7.03 ± 0.25 ab | N.D. | 0.15 ± 0.02 abc | 9.69 ± 1.83 de | |
170 | 4 | 0.23 ± 0.02 a | 1.08 ± 0.10 ab | 42.46 ± 0.75 a | 5.18 ± 0.28 a | 40.35 ± 1.85 ab | 10.70 ± 1.00 e | N.D. | 0.25 ± 0.02 hi | 0.00 ± 0.00 a |
8 | 0.25 ± 0.03 a | 1.17 ± 0.17 abc | 43.65 ± 1.29 a | 5.33 ± 0.44 a | 39.02 ± 2.14 ab | 10.44 ± 1.75 de | N.D. | 0.24 ± 0.04 ghi | 3.93 ± 0.32 abc | |
12 | 0.24 ± 0.02 a | 1.20 ± 0.16 abc | 45.69 ± 1.97 a | 6.49 ± 0.24 ab | 36.95 ± 1.68 ab | 9.28 ± 0.16 bcde | N.D. | 0.20 ± 0.01 cdefgh | 5.27 ± 0.58 abcd | |
16 | 0.24 ± 0.03 a | 1.11 ± 0.07 ab | 45.24 2.38 a | 6.77 ± 2.60 ab | 38.08 ± 0.82 ab | 8.44 ± 0.69 abcde | N.D. | 0.19 ± 0.01 bcdefg | 13.49 ± 0.91 ef | |
20 | 0.26 ± 0.09 a | 1.16 ± 0.36 abc | 47.69 ± 13.55 a | 6.81 ± 3.55 ab | 36.71 ± 11.76 ab | 7.21 ± 1.52 ab | N.D. | 0.16 ± 0.03 abcd | 13.82 ± 1.51 ef | |
24 | 0.26 ± 0.04 a | 1.20 ± 0.15 abc | 49.09 ± 5.71 a | 7.32 ± 1.51 ab | 34.67 ± 5.12 ab | 7.29 ± 0.89 ab | N.D. | 0.15 ± 0.01 abc | 16.77 ± 0.79 fg | |
180 | 4 | 0.19 ± 0.05 a | 0.93 ± 0.13 a | 43.94 ± 5.40 a | 5.02 ± 1.50 a | 39.28 ± 5.89 ab | 10.56 ± 1.47 de | N.D. | 0.24 ± 0.00 ghi | 2.16 ± 0.29 ab |
8 | 0.24 ± 0.05 a | 1.11 ± 0.17 ab | 44.94 ± 4.20 a | 5.30 ± 3.16 a | 38.32 ± 3.89 ab | 9.94 ± 1.35 cde | N.D. | 0.22 ± 0.02 efghi | 5.05 ± 1.98 abcd | |
12 | 0.22 ± 0.01 a | 1.10 ± 0.05 ab | 46.58 ± 2.33 a | 5.52 ± 1.33 a | 37.57 ± 2.61 ab | 8.68 ± 0.81 bcde | N.D. | 0.19 ± 0.01 bcdefg | 9.00 ± 3.25 cde | |
16 | 0.23 ± 0.02 a | 1.15 ± 0.07 ab | 48.37 ± 2.77 a | 5.82 ± 0.43 a | 35.87 ± 3.32 ab | 8.14 ± 0.88 abcd | N.D. | 0.17 ± 0.01 abcde | 19.29 ± 6.12 g | |
20 | 0.22 ± 0.01 a | 1.17 ± 0.07 abc | 49.26 ± 2.60 a | 5.94 ± 1.01 a | 35.63 ± 2.11 ab | 7.18 ± 0.41 ab | N.D. | 0.15 ± 0.01 ab | 21.08 ± 2.15 g | |
24 | 0.24 ± 0.01 a | 1.34 ± 0.20bc | 50.50 ± 4.33 a | 6.12 ± 0.75 ab | 34.96 ± 1.86 ab | 6.11 ± 1.57 a | N.D. | 0.12 ± 0.04 a | 29.13 ± 3.87 h |
TPC | TAGO | TAGD | OXTAGM | DAG | FFA | EPOXY | KETO | HYDROXY | PV | AV | TOTOX | C8 | |
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
TPC | 1.000 | - | - | - | - | - | - | - | - | - | - | - | - |
TAGO | 0.976 | 1.000 | - | - | - | - | - | - | - | - | - | - | - |
TAGD | 0.792 | 0.838 | 1.000 | - | - | - | - | - | - | - | - | - | - |
OXTAGM | 0.845 | 0.876 | 0.950 | 1.000 | - | - | - | - | - | - | - | - | - |
DAG | −0.900 | −0.935 | −0.969 | −0.980 | 1.000 | - | - | - | - | - | - | - | - |
FFA | −0.786 | −0.815 | −0.878 | −0.874 | 0.874 | 1.000 | - | - | - | - | - | - | - |
EPOXY | 0.886 | 0.893 | 0.703 | 0.714 | −0.793 | −0.710 | 1.000 | - | - | - | - | - | - |
KETO | 0.816 | 0.811 | 0.651 | 0.690 | −0.739 | −0.661 | 0.865 | 1.000 | - | - | - | - | - |
HYDROXY | 0.750 | 0.752 | 0.677 | 0.719 | −0.738 | −0.701 | 0.802 | 0.886 | 1.000 | - | - | - | - |
PV | −0.472 | −0.485 | −0.634 | −0.658 | 0.610 | 0.676 | −0.440 | −0.409 | −0.588 | 1.000 | - | - | - |
AV | 0.853 | 0.897 | 0.909 | 0.880 | −0.928 | −0.850 | 0.817 | 0.752 | 0.722 | −0.644 | 1.000 | - | - |
TOTOX | 0.858 | 0.905 | 0.886 | 0.848 | −0.913 | −0.810 | 0.824 | 0.757 | 0.685 | −0.507 | 0.986 | 1.000 | - |
C8 | 0.885 | 0.865 | 0.623 | 0.652 | −0.735 | −0.628 | 0.870 | 0.816 | 0.672 | −0.329 | 0.786 | 0.813 | 1.000 |
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Khor, Y.P.; Hew, K.S.; Abas, F.; Lai, O.M.; Cheong, L.Z.; Nehdi, I.A.; Sbihi, H.M.; Gewik, M.M.; Tan, C.P. Oxidation and Polymerization of Triacylglycerols: In-Depth Investigations towards the Impact of Heating Profiles. Foods 2019, 8, 475. https://doi.org/10.3390/foods8100475
Khor YP, Hew KS, Abas F, Lai OM, Cheong LZ, Nehdi IA, Sbihi HM, Gewik MM, Tan CP. Oxidation and Polymerization of Triacylglycerols: In-Depth Investigations towards the Impact of Heating Profiles. Foods. 2019; 8(10):475. https://doi.org/10.3390/foods8100475
Chicago/Turabian StyleKhor, Yih Phing, Khai Shin Hew, Faridah Abas, Oi Ming Lai, Ling Zhi Cheong, Imededdine Arbi Nehdi, Hassen Mohamed Sbihi, Mohamed Mossad Gewik, and Chin Ping Tan. 2019. "Oxidation and Polymerization of Triacylglycerols: In-Depth Investigations towards the Impact of Heating Profiles" Foods 8, no. 10: 475. https://doi.org/10.3390/foods8100475