CN115326774B - 3-MCPD detection method based on fluorescence analysis and catechol - Google Patents
3-MCPD detection method based on fluorescence analysis and catechol Download PDFInfo
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- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 title claims abstract description 125
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 title claims abstract description 112
- 238000001514 detection method Methods 0.000 title claims abstract description 56
- 238000012921 fluorescence analysis Methods 0.000 title claims abstract description 23
- 239000000243 solution Substances 0.000 claims abstract description 120
- 229920002873 Polyethylenimine Polymers 0.000 claims abstract description 35
- 239000012086 standard solution Substances 0.000 claims abstract description 31
- 238000002835 absorbance Methods 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 23
- 239000000126 substance Substances 0.000 claims abstract description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 235000019482 Palm oil Nutrition 0.000 claims description 20
- 239000002540 palm oil Substances 0.000 claims description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 235000013555 soy sauce Nutrition 0.000 claims description 18
- 238000010438 heat treatment Methods 0.000 claims description 16
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- 238000000295 emission spectrum Methods 0.000 claims description 13
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- 238000002156 mixing Methods 0.000 claims description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 10
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- 239000004576 sand Substances 0.000 claims description 9
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 claims description 7
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- 238000002360 preparation method Methods 0.000 claims description 7
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- 239000011780 sodium chloride Substances 0.000 claims description 6
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 4
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
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- 239000000203 mixture Substances 0.000 claims description 2
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- WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-benzoquinone Chemical compound O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 abstract description 13
- 238000002474 experimental method Methods 0.000 abstract description 5
- 231100000252 nontoxic Toxicity 0.000 abstract description 3
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- 239000000523 sample Substances 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 239000012488 sample solution Substances 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 238000004448 titration Methods 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 230000015572 biosynthetic process Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- -1 o-quinone compound Chemical class 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
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- 239000001301 oxygen Substances 0.000 description 2
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- 239000000047 product Substances 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- RZWHKKIXMPLQEM-UHFFFAOYSA-N 1-chloropropan-1-ol Chemical compound CCC(O)Cl RZWHKKIXMPLQEM-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010029155 Nephropathy toxic Diseases 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
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- 238000010586 diagram Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 231100000025 genetic toxicology Toxicity 0.000 description 1
- 230000001738 genotoxic effect Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007694 nephrotoxicity Effects 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
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- 238000004445 quantitative analysis Methods 0.000 description 1
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- 230000004044 response Effects 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N1/00—Sampling; Preparing specimens for investigation
- G01N1/28—Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6432—Quenching
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Abstract
The invention provides a 3-MCPD detection method based on fluorescence analysis and catechol. According to the method, firstly, catechol solution and polyethyleneimine solution are respectively added to 3-MCPD standard solutions with different concentrations, the pH value is adjusted to 8-9, then the solution is placed under the temperature condition of 55-65 ℃ to react until the solution is pale yellow, a fluorescence spectrophotometer is used for detection, and the detected absorbance value and the concentration of 3-MCPD are linearly fitted to obtain a standard curve equation; and (3) treating the sample to be detected in the same way, detecting by adopting a fluorescence spectrophotometer, and carrying the detected absorbance value into an equation to calculate the concentration of the 3-MCPD. According to the invention, catechol is utilized to form o-quinone substances in a polyethyleneimine alkaline environment, then 3-MCPD is added to quench the o-quinone substances, and a 3-MCPD detection method which is simple, effective, convenient, nontoxic, environment-friendly and high in sensitivity is established based on an o-quinone fluorescent signal quenched by the 3-MCPD, and the detection result is proved to be accurate through experiments.
Description
Technical Field
The invention relates to a detection method, in particular to a 3-MCPD detection method based on fluorescence analysis and catechol.
Background
3-MCPD has extremely pronounced nephrotoxicity and high degree of genotoxicity, and has been strictly classified as a 2B carcinogen by the united nations international cancer organization (IARC) working group. As is well known, 3-MCPD is a by-product of the reaction of triacylglycerols, phospholipids or glycerol with hydrochloric acid in fatty or fat-containing foods, which is heated to form food processing contaminants. When glycerol, lecithin and other 3-MCPD esters of glycerol or other sources are present, prolonged heating at high temperature in the presence of hydrochloric acid (HCl) is believed to be responsible for the formation of 3-MCPD, the presence of chloride ions being important for the formation of 3-MCPD and its isomers. Detection methods such as chromatography and mass spectrometry in the common methods for detecting 3-MCPD are expensive, long in detection time and complex in operation, and the chloropropanol content in the seasoning cannot be rapidly monitored in real time. Since 3-MCPD exists in a variety of foods, it is imperative to establish a simple, sensitive 3-MCPD assay.
Fluorescence analysis refers to the use of substances that collide with excited molecules and emit excitation under ultraviolet light excitation. Qualitative or quantitative analysis methods reflecting the characteristics of the fluorescent material may be employed. Fluorescence analysis has attracted considerable attention from researchers. Researchers find that fluorescence analysis is a good detection means, and compared with the traditional detection method, fluorescence analysis has the advantages of high sensitivity (103-104 times higher than spectrophotometry), wide linearity and the like. Meanwhile, fluorescence analysis is rapidly developed, and the application is increasingly wide. The rapid response of fluorescent signals is one of the main advantages of the fluorescent signals, and the fluorescent signals can be used for real-time detection. Established fluorescence analysis methods have been widely used in the analytical field, such as the determination of inorganic, organic and biological macromolecules.
Disclosure of Invention
Aiming at the problems existing in the prior art, the invention provides a 3-MCPD detection method based on fluorescence analysis and catechol, which has high detection sensitivity, convenient operation and low cost, and does not need large detection equipment.
In order to achieve the technical aim, the invention provides a simple 3-MCPD detection method based on fluorescence analysis and catechol, which is characterized by comprising the following specific steps:
(1) Catechol solution preparation: dissolving solid catechol in ultrapure water to prepare catechol solution;
(2) Preparation of polyethyleneimine solution: dissolving a polyethyleneimine standard substance in ultrapure water to prepare a polyethyleneimine solution;
(3) A standard curve equation of the concentration c of 3-MCPD and the fluorescence intensity T is prepared:
a. preparing 3-MCPD standard solutions with different concentrations;
b. respectively adding the catechol solution prepared in the step (1) to 3-MCPD standard solutions with different concentrations, and adding the polyethyleneimine solution prepared in the step (2) to adjust the pH value to 8-9, wherein the mass concentration of the catechol in the 3-MCPD standard solution with each concentration is 0.05-0.08 mg/mL;
c. c, placing the 3-MCPD standard solution added with catechol in the step b at the temperature of 55-65 for reaction for 10-15 min until the solution is light yellow, stopping heating, then cooling to room temperature, detecting by using a fluorescence spectrophotometer, and measuring the corresponding absorbance values of the 3-MCPD standard solutions with different concentrations;
d. performing linear fitting on the absorbance value corresponding to the measured standard solution and the concentration of 3-MCPD to obtain a standard curve equation of the corresponding relation between the absorbance value T and the concentration c of 3-MCPD;
(4) Placing a sample to be detected in a container, repeating the step b of the step (3) and adding catechol solution and polyethyleneimine solution to prepare a detection solution, repeating the step c of the step (3) to perform heating reaction, cooling to room temperature, detecting by using a fluorescence spectrophotometer to obtain an absorbance value T of the detection solution, and substituting the detected absorbance value T into a standard curve equation in the step d of the step (3) to calculate the concentration of 3-MCPD in the sample to be detected.
The invention has the preferable technical scheme that: preparing 6 3-MCPD standard solutions in the step (3), wherein the concentrations of the solutions are respectively 0, 0.08, 0.2, 0.4, 0.8 and 2mg L-1; the wavelength of the excitation spectrum of the fluorescence spectrophotometer is 370nm, the fluorescence intensity of 6 3-MCPD standard solutions at the position of the emission spectrum wavelength of 480nm is detected, the absorbance corresponding to the 6 3-MCPD standard solutions is 3413, 3011, 2713, 2455, 2032 and 449.9 respectively, the absorbance value corresponding to the detected standard solutions and the concentration of 3-MCPD are subjected to linear fitting, and a standard curve equation of the corresponding relation between the absorbance value T and the concentration c of 3-MCPD is obtained: t= -1369.2c+3139.8.
The invention further adopts the technical scheme that: and (3) the sample to be detected in the step (4) is palm oil, soy sauce or tap water.
The invention has the preferable technical scheme that: adding the polyethyleneimine solution prepared in the step (2) in the step b of the step (3) to adjust the pH value to 8.5; in step c, the 3-MCPD standard solution added with catechol is placed in a sand bath at 60 for reaction for 10min, when the solution is light yellow, heating is stopped, and then the solution is placed in an ice bath for cooling to room temperature.
The invention has the preferable technical scheme that: the concentration of the catechol solution in the step (1) is 4-8 mg/mL.
The invention has the preferable technical scheme that: the concentration of the polyethyleneimine solution in the step (2) is 5-6 mg/mL.
The invention has the preferable technical scheme that: when the sample to be detected is palm oil, the palm oil is pretreated before detection, and the treatment process is as follows:
(1) Palm oil was dissolved in isooctane at a mass to volume ratio of 0.1g to 0.5ml, and then added to H 2 SO 4 Mixing with n-propanol, performing ultrasonic treatment in 45 deg.C water bath for 15min after vortex mixing, adding 0.5 mol/L sodium methoxide solution for rapid hydrolysis for 3min, and rapidly adding n-heptane and 3.3% glacial acetic acid solution after hydrolysis is completed to terminate reaction; wherein the H is 2 SO 4 And n-propanol in a mixing volume ratio of 0.5%; the glacial acetic acid solution with the concentration of 3.3 percent is prepared by dissolving glacial acetic acid in NaCl solution with the concentration of 0.01 g/mL; the mass volume ratio of the palm oil to the sodium methoxide with the concentration of 0.5 mol/L is 0.1 g/1 ml; the mass volume ratio of the palm oil to the n-heptane is 0.1 g/3 ml; the mass volume ratio of the palm oil to the glacial acetic acid with the concentration of 3.3% is 0.1 g/3 ml;
(2) Removing an upper organic phase after full reaction in the step (1), extracting twice by using n-heptane, removing residual nonpolar components in the solution, and taking a lower aqueous phase as a sample detection solution of palm oil; the mass-to-volume ratio of palm oil to n-heptane at each extraction was 0.1 g/3 ml.
The invention has the preferable technical scheme that: when the sample to be detected is soy sauce, the soy sauce is subjected to pretreatment before detection, and the treatment process is as follows: adding 5mol/L NaCl solution into the finished soy sauce according to the mass-volume ratio of 2g to 3ml, mixing, loading the mixture into a solid phase extraction column, eluting with a hexane-diethyl ether mixed solution, eluting with diethyl ether, collecting diethyl ether eluent, removing solvent, adding water into a centrifuge tube, and shaking uniformly to obtain a soy sauce sample detection solution; wherein the hexane-diethyl ether mixed solution is prepared by mixing according to the volume ratio of 9:1; the mass volume ratio of the soy sauce to the hexane-diethyl ether mixed solution is 1g to 10ml; the mass-volume ratio of the soy sauce to the diethyl ether is 2g to 75ml; the mass volume ratio of the soy sauce to the water is 1g to 0.25ml.
The invention has the preferable technical scheme that: when the sample to be detected is tap water, the tap water sample is centrifuged at a high speed before detection, and the supernatant is filtered by a filter membrane of 0.45 and um to obtain a tap water sample detection solution.
In the present invention, the catechol group is gradually converted to the o-quinone intermediate (max=425 nm) under the condition of air oxygen, and once oxidized, cannot return to the catechol structure, and the process is irreversible. The o-quinone contains chromophore, and is light yellow under ultraviolet irradiation, and 3-MCPD can influence the formation of o-quinone to a certain extent. Fluorescence analysis is utilized to obtain corresponding absorbance at different temperatures and different pH values; then 3-MCPD of different concentrations is added to the mixed solution of catechol and polyethyleneimine, in fact 3-MCPD reacts easily with the hydroxyl functions of catechol by substituting chlorine atoms in alkaline solutions. Thus, the concentration of 3-MCPD can be determined by directly measuring the light absorption of pale yellow oxidation products produced under alkaline or oxidizing agent conditions. Experiments show that the method has high extraction rate on 3-MCPD and can finish the detection on 3-chloro-1, 2-propanediol.
In the invention, catechol is utilized to form o-quinone substances in an alkaline environment of polyethyleneimine, and then 3-MCPD is added to quench the o-quinone substances. In a word, based on the 3-MCPD quenched o-quinone fluorescent signal, a simple, effective, convenient, nontoxic, environment-friendly and high-sensitivity 3-MCPD detection method is established.
Drawings
FIG. 1 is a schematic diagram of the reaction in the detection process of the present invention;
FIG. 2 is a graph of fluorescence intensity of catechol at different concentrations for the same concentration of PEI in experiment one;
FIG. 3 is a graph showing fluorescence intensity curves at different pH values at the same concentration of 3-MCPD in test two
FIG. 4 is a graph of fluorescence intensity at different temperature values for the same concentration of 3-MCPD in test three;
FIG. 5 is a graph showing fluorescence intensity of 3-MCPD solutions at various concentrations at 60and pH 8.5 in test four;
FIG. 6 is a graph showing the correspondence between fluorescence intensity and 3-MCPD concentration in examples.
Detailed description of the preferred embodiments
The invention is further described below with reference to the drawings and examples. The following technical solutions presented in the drawings are specific to embodiments of the present invention and are not intended to limit the scope of the claimed invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The invention provides a 3-MCPD detection method based on fluorescence analysis and catechol; the method sequentially comprises the steps of catechol solution preparation, polyethyleneimine solution preparation, preparation of a standard curve equation of the concentration c of 3-MCPD and the fluorescence intensity T, detection by using a fluorescence spectrophotometer to obtain an absorbance value T of a detection solution, and substituting the detected absorbance value T into the standard curve equation to calculate the concentration of 3-MCPD in the sample solution to be detected.
The detection principle of the invention is shown in figure 1: under the condition of air oxygen, catechol group is gradually converted into o-quinone intermediate, and o-quinone contains chromophore and is light yellow under the irradiation of ultraviolet light. Meanwhile, 3-MCPD can easily react with the hydroxyl functional group of catechol by substituting chlorine atoms in alkaline solution. Thus, the concentration of 3-MCPD can be determined by directly measuring the fluorescence intensity of the oxidation product produced under alkaline or oxidizing agent conditions.
For the above detection method, the inventors of the present application conducted the following experiments, prior to which catechol solution, polyethyleneimine solution, and 3-MCPD solution were prepared; wherein, the catechol solution is prepared by weighing 40-80 mg of catechol solid in a centrifuge tube, adding 10mL of ultrapure water for dissolution, and preparing 4-8 mg/mL of catechol solution; the polyethyleneimine solution is prepared by weighing 55 mg of polyethyleneimine standard substance, dissolving in a centrifuge tube, adding 10mL of ultrapure water for dissolving, and preparing 5.5mg/mL of polyethyleneimine solution; the 3-MCPD solution is prepared by weighing 3-MCPD standard substances with different mass into a centrifuge tube, adding 10mL of ultrapure water for dissolution, and preparing the 3-MCPD solutions with different concentrations.
Test one, selecting the optimal catechol concentration: taking 5 centrifuge tubes, adding 40uL,60uL,80uL,100uL and 120uL of prepared catechol solution into the centrifuge tubes with the numbers of 1,2,3,4 and 5, sucking 5.5mg/mL of polyethyleneimine solution into the 5 centrifuge tubes by using a 100uL pipette, detecting by using a pH meter, enabling the pH value to reach 8.5, and finally adding ultrapure water into the 5 centrifuge tubes for titration to 3mL. And placing 5 centrifuge tubes in a 60 sand bath for reaction for 10min, stopping heating when the solution is light yellow, then placing the solution in the ice bath for cooling to room temperature, detecting by using a fluorescence spectrophotometer, wherein the excitation spectrum wavelength of the fluorescence spectrophotometer is 370nm, detecting the fluorescence intensity of the solution at the position of 480nm of the emission spectrum wavelength, and the detection result is shown in figure 2, wherein the fluorescence intensity is strongest when the concentration of catechol solution is 0.05-0.08 mg/mL as shown in figure 2, and the fluorescence intensity is reduced along with the increase of the concentration. Therefore, the optimum catechol concentration is 0.05 to 0.08mg/mL.
Test two, selecting the optimal pH value of the 3-MCPD quenched o-quinone compound: taking 5 centrifuge tubes, taking the centrifuge tubes with the numbers of 1,2,3,4 and 5, sucking 20-40uL of the catechol solution with the matched concentration of 4-8 mg/mL by using a 100uL pipetting gun, placing the catechol solution into the 5 centrifuge tubes, adding 5.5mg/mL of polyethyleneimine solution with different contents into the centrifuge tubes with the numbers of 1,2,3,4 and 5 respectively, detecting the polyethyleneimine solution by using a pH meter to ensure that the pH values of the polyethyleneimine solution are 7, 7.5, 8, 8.5 and 9, then adding 30uL of the 3-MCPD solution with the concentration of 40ug/mL into the 5 centrifuge tubes respectively, and finally adding ultrapure water into the 5 centrifuge tubes for titration to 3mL. The 5 centrifuge tubes are placed in a sand bath at 60 for reaction for 10min, when the solution is light yellow, heating is stopped, then the solution is placed in an ice bath and cooled to room temperature, the fluorescence is detected by using a fluorescence spectrophotometer, the excitation spectrum wavelength of the fluorescence spectrophotometer is 370nm, the fluorescence intensity of the detection solution at the position with the emission spectrum wavelength of 480nm is detected, the detection result is shown in figure 3, the fluorescence intensity of the detection solution gradually increases along with the increase of the pH value of the detection solution from figure 3, and when the pH value reaches 8.5, the fluorescence intensity of the detection solution is strongest and linearly decreases beyond 8.5. It can be seen that the optimum pH is 8.5.
Test three, selecting the optimal temperature for quenching the o-quinone compound by 3-MCPD: taking 5 centrifuge tubes, taking the numbers 1,2,3,4 and 5 of the centrifuge tubes, sucking 20-40uL of the catechol solution with the matched concentration of 4-8 mg/mL by a 40uL pipetting gun into the 5 centrifuge tubes, adding a certain content of 5.5mg/mL of polyethyleneimine solution into the centrifuge tubes, detecting by a pH meter to ensure that the pH value reaches the optimal pH value of 8.5, adding 30uL of the 3-MCPD solution with the concentration of 40ug/mL into the 5 centrifuge tubes respectively, and finally adding ultra-pure water into the 5 centrifuge tubes for titration to 3mL. Placing 5 centrifuge tubes in a sand bath, respectively reacting for 10min at 20 , 40 ,60 ,80 and 100 , stopping heating until the solution is light yellow, then cooling to room temperature, detecting by using a fluorescence spectrophotometer, wherein the excitation spectrum wavelength of the fluorescence spectrophotometer is 370nm, detecting the fluorescence intensity of the solution at the position of 480nm of the emission spectrum wavelength, and as shown in fig. 4, the detection result shows that the fluorescence intensity initially decreases linearly with the increase of the temperature, the fluorescence intensity is lowest at 40 , the fluorescence intensity subsequently increases linearly with the increase of the temperature, and the fluorescence intensity is strongest and begins to decrease again when the temperature rises to 60 . It can be seen that the optimum reaction temperature is 60 .
Effect of assay four, 3-MCPD concentration on fluorescence intensity: taking 6 centrifuge tubes, carrying out serial numbers of 1,2,3,4,5 and 6, sucking catechol solution with optimal concentration of 0.05mg/mL into the 6 centrifuge tubes by using a 100uL pipetting gun, adding 5.5mg/mL polyethyleneimine solution with certain content into the centrifuge tubes, detecting by using a pH meter to ensure that the pH value is 8.5, adding 0uL,6uL,15uL,30uL,60uL and 150uL of 40ug/mL 3-MCPD solution into the 6 centrifuge tubes respectively, and finally adding ultrapure water into the 6 centrifuge tubes for titration to 3mL. The temperature of the marmite is set to be the optimal temperature of 60 ,6 centrifuge tubes are placed in the marmite for reaction for 10min, when the solution is light yellow, heating is stopped, then the marmite is cooled to room temperature, the excitation spectrum of the fluorescence spectrophotometer is 370nm, the fluorescence intensity of the solution at the place with the emission spectrum wavelength of 480nm is detected, the detection result is shown in fig. 5, the fluorescence gradually decreases along with the increase of the concentration of the 3-MCPD solution, the quenching effect of the 3-MCPD on the o-quinone substances is shown, and the inverse proportion between the concentration and the fluorescence of the 3-MCPD solution can be seen.
The invention is further illustrated below with reference to examples in which catechol solution, polyethylenimine solution, and 3-MCPD solution, prepared according to the methods in the above experiments, were used; the standard curve of the linear relationship between 3-MCPD concentration and fluorescence intensity in the following examples was prepared as follows:
a. first, 6 standard solutions of 3-MCPD were prepared at concentrations of 0, 0.08, 0.2, 0.4, 0.8, 2mg L, respectively -1
b. Respectively placing six 3-MCPD standard solutions with different concentrations into a centrifuge tube, adding the prepared catechol solution, and adding the prepared polyethyleneimine solution to adjust the pH value to 8.5, wherein the mass concentration of the catechol in the 3-MCPD standard solution with each concentration is 0.05mg/mL;
c. c, placing the 3-MCPD standard solution added with catechol in the step b in a sand bath at 60 for heating reaction for 10min until the solution is light yellow, stopping heating, then placing the solution in an ice bath for cooling to room temperature, detecting by using a fluorescence spectrophotometer, wherein the excitation spectrum wavelength of the fluorescence spectrophotometer is 370nm, detecting the fluorescence intensity of the 6 3-MCPD standard solutions at the position with the emission spectrum wavelength of 480nm, and the absorbance corresponding to the 6 3-MCPD standard solutions is 3413, 3011, 2713, 2455, 2032 and 449.9 respectively;
d. performing linear fitting on the absorbance value corresponding to the measured standard solution and the concentration of 3-MCPD, and finally obtaining a standard curve equation of the corresponding relation between the absorbance value T and the concentration c of 3-MCPD as shown in figure 6, wherein the standard curve equation is as follows: t= -1369.2c+3139.8.
Embodiment one: 0.1g of palm oil was weighed into 500uL of isooctane and 0.5mL of H was added 2 SO 4 N-propanol (v/v, 0.5%) solution, mixing with vortex, ultrasonic treating in 45 deg.C water bath for 15min, and adding 1mL 0.5 mol/L sodium methoxide solution for rapid hydrolysis for 3min; after the hydrolysis was completed, 3.3 mL n-heptane and 3mL of 3.3% glacial acetic acid (dissolved in 0.01 g/mL NaCl) were added rapidly to terminate the reaction; after sufficient extraction, the upper organic phase was removed, the solution was extracted twice with 3, mL n-heptane, the remaining non-polar components were removed, 1mL of the lower aqueous phase was placed in a centrifuge tube, 40, uL of 4, mg/mL catechol was aspirated into the centrifuge tube by a 40, uL pipette, and a 5.5mg/mL polyethyleneimine solution was added to the centrifuge tube and detected with a pH meter to a pH of 8.5. Finally adding ultrapure water into the centrifuge tube for titration to 3mL. The centrifuge tube was placed in a 60 sand bath for reaction for 10min, and when the solution appeared pale yellow, the heating was stopped, then the centrifuge tube was cooled to room temperature in an ice bath, and the detection was performed using a fluorescence spectrophotometer. Scanning the emission spectrum by using a fluorescence spectrophotometer, wherein the wavelength of the excitation spectrum is 370nm, the fluorescence intensity of the sample solution at the wavelength of the emission spectrum is 480nm, the absorbance value of the sample solution is 1988.62, the concentration of 3-MCPD in the sample solution is determined by a standard curve, and the concentration of 3-MCPD in the sample is about 0.84 mg L obtained by conversion of the formula T= -1369.2c+3139.8 -1
Embodiment two: weighing 4 g soy sauce, mixing with 6mL of 5mol/L NaCl solution, loading to a sample solid phase extraction column, eluting with 40mL of hexane-diethyl ether (90:10, v/v), eluting with 150mL of diethyl ether, collecting diethyl ether eluent, removing solvent, adding 1mL of water, shaking uniformly in a centrifuge tube, sucking 32uL of 5mg/mL catechol in the centrifuge tube by using a 40uL pipette, adding a certain content of 5.5mg/mL polyethyleneimine solution into the centrifuge tube, and detecting by using a pH meter to ensure that the pH value is 8.5. Finally adding ultra-pure water into the centrifuge tube for titration3mL. The centrifuge tube was placed in a 60 sand bath for reaction for 10min, and when the solution appeared pale yellow, the heating was stopped, then the centrifuge tube was cooled to room temperature in an ice bath, and the detection was performed using a fluorescence spectrophotometer. Scanning the emission spectrum by using a fluorescence spectrophotometer, wherein the wavelength of the excitation spectrum is 370nm, the fluorescence intensity of the sample solution at the wavelength of the emission spectrum is 480nm, the absorbance value of the sample solution is 1876.32, the concentration of 3-MCPD in the sample solution is determined by a standard curve, and the concentration of 3-MCPD in the sample is about 0.92 mg L obtained by conversion of the formula T= -1369.2c+3139.8 -1
Embodiment III: taking a tap water sample, centrifuging at a high speed, filtering the supernatant by using a 0.45um filter membrane, taking the 1mL treated water sample into a centrifuge tube, sucking 20uL of 8mg/mL catechol into the centrifuge tube by using a 40uL pipette, adding a certain content of 5.5mg/mL polyethyleneimine solution into the centrifuge tube, and detecting by using a pH meter to ensure that the pH value is 8.5. Finally adding ultrapure water into the centrifuge tube for titration to 3mL. The centrifuge tube was placed in a 60 sand bath for reaction for 10min, and when the solution appeared pale yellow, the heating was stopped, then the centrifuge tube was cooled to room temperature in an ice bath, and the detection was performed using a fluorescence spectrophotometer. Scanning the emission spectrum by using a fluorescence spectrophotometer, wherein the wavelength of the excitation spectrum is 370nm, the fluorescence intensity of the sample solution at the wavelength of the emission spectrum is 480nm, the absorbance value of the sample solution is 2038.54, the concentration of 3-MCPD in the sample solution is determined by a standard curve, and the concentration of 3-MCPD in the sample is about 0.80 mg L obtained by conversion of the formula T= -1369.2c+3139.8 -1
Comparison test: the palm oil sample and soy sauce sample in the first and second examples were treated as follows, and then analyzed by gas chromatography-mass spectrometry (GC-MS), and the treatment procedure was as follows: in a 10ml tube, 0.1g of the oil sample was dissolved in 200. Mu.L of isooctane; after adding 3.3 mL of a 30% aqueous sodium bromide solution (adjusted to pH 5.0 with citric acid and disodium hydrogen phosphate) containing 90U/mL lipase, the solution was subjected to vertical shaking at room temperature of 25for 30 min with a high-speed shaking screen to hydrolyze the ester; the test tube was heated in a 80water bath for 10min, cooled to room temperature, and an internal standard solution of 2.0. Mu.g/mL 3-MCPD-d was added 5 50. Mu L. Next, add3ml of hexane was added, shaken for 10 seconds, the resulting aqueous layer was transferred to a new test tube, 3ml of hexane was added, the tube was shaken for 10 seconds, and the resulting hexane layer was then removed. Adding 20 l of PBA solution into the water layer, stirring with vortex mixer for 10 seconds, derivatizing, adding 3ml of hexane, shaking for 10 seconds, and extracting the derivative; the resulting organic layer was transferred to a new test tube and concentrated to about 0.5-0.8mL (with a nitrogen sparger) using a nitrogen stream to give a test sample. After the detection sample is filtered by a 0.2 m filter membrane, gas chromatography-mass spectrometry (GC-MS) analysis is carried out, and the analysis result shows that the concentration of 3-MCPD in the sample is almost the same as the calculated concentration, and the error range is +/-0.04.
After the tap water samples in the third example were pretreated in the same manner as in the third example, gas chromatography-mass spectrometry (GC-MS) analysis was performed, and the detection results showed that the concentration of 3-MCPD in the samples was almost the same as the calculated concentration, and the error range was 0.04.
As can be seen from the above comparative tests, the method in the present application has accurate detection results.
The invention establishes a simple, effective, convenient, nontoxic, environment-friendly and high-sensitivity 3-MCPD detection method based on the 3-MCPD quenched o-quinone fluorescent signal. The 3-MCPD concentration is linear with fluorescence intensity. At 0.08-2.0 mg L -1 In the range, the linear correlation coefficient f= -1369.16 c+3139.76. The correlation coefficient was 0.9930. When the concentration of 3-MCPD is 0.08L mg L -1 -2.0 mgL -1 In between, fluorescence intensity and 3-MCPD concentration are highly linearly related (R 2 =0.97792)
The foregoing description is of one embodiment of the invention and is thus not to be taken as limiting the scope of the invention. It should be noted that it will be apparent to those skilled in the art that several variations and modifications can be made without departing from the spirit of the invention, which are all within the scope of the invention. Accordingly, the scope of the invention should be assessed as that of the appended claims.
Claims (9)
1. A3-MCPD detection method based on fluorescence analysis and catechol is characterized by comprising the following specific steps:
(1) Catechol solution preparation: dissolving solid catechol in ultrapure water to prepare catechol solution;
(2) Preparation of polyethyleneimine solution: dissolving a polyethyleneimine standard substance in ultrapure water to prepare a polyethyleneimine solution;
(3) A standard curve equation of the concentration c of 3-MCPD and the fluorescence intensity T is prepared:
a. preparing 3-MCPD standard solutions with different concentrations;
b. respectively adding the catechol solution prepared in the step (1) to 3-MCPD standard solutions with different concentrations, and adding the polyethyleneimine solution prepared in the step (2) to adjust the pH value to 8-9, wherein the mass concentration of the catechol in the 3-MCPD standard solution with each concentration is 0.05-0.08 mg/mL;
c. c, placing the 3-MCPD standard solution added with catechol in the step b at the temperature of 55-65 for reaction for 10-15 min until the solution is light yellow, stopping heating, then cooling to room temperature, detecting by using a fluorescence spectrophotometer, and measuring the corresponding absorbance values of the 3-MCPD standard solutions with different concentrations;
d. performing linear fitting on the absorbance value corresponding to the measured standard solution and the concentration of 3-MCPD to obtain a standard curve equation of the corresponding relation between the absorbance value T and the concentration c of 3-MCPD;
(4) Placing a sample to be detected in a container, repeating the step b of the step (3) and adding catechol solution and polyethyleneimine solution to prepare a detection solution, repeating the step c of the step (3) to perform heating reaction, cooling to room temperature, detecting by using a fluorescence spectrophotometer to obtain an absorbance value T of the detection solution, and substituting the detected absorbance value T into a standard curve equation in the step d of the step (3) to calculate the concentration of 3-MCPD in the sample to be detected.
2. The method for detecting 3-MCPD based on fluorescence analysis and catechol according to claim 1, wherein: preparing 6 3-MCPD standard solutions in the step (3), wherein the concentrations of the solutions are respectively 0, 0.08, 0.2, 0.4, 0.8 and 2mg L-1; the wavelength of the excitation spectrum of the fluorescence spectrophotometer is 370nm, the fluorescence intensity of 6 3-MCPD standard solutions at the position of the emission spectrum wavelength of 480nm is detected, the absorbance corresponding to the 6 3-MCPD standard solutions is 3413, 3011, 2713, 2455, 2032 and 449.9 respectively, the absorbance value corresponding to the detected standard solutions and the concentration of 3-MCPD are subjected to linear fitting, and a standard curve equation of the corresponding relation between the absorbance value T and the concentration c of 3-MCPD is obtained: t= -1369.2c+3139.8.
3. A method for detecting 3-MCPD based on fluorescence analysis and catechol according to claim 1 or 2, characterized in that: and (3) the sample to be detected in the step (4) is palm oil, soy sauce or tap water.
4. A method for detecting 3-MCPD based on fluorescence analysis and catechol according to claim 1 or 2, characterized in that: adding the polyethyleneimine solution prepared in the step (2) in the step b of the step (3) to adjust the pH value to 8.5; in step c, the 3-MCPD standard solution added with catechol is placed in a sand bath at 60 for reaction for 10min, when the solution is light yellow, heating is stopped, and then the solution is placed in an ice bath for cooling to room temperature.
5. A method for detecting 3-MCPD based on fluorescence analysis and catechol according to claim 1 or 2, characterized in that: the concentration of the catechol solution in the step (1) is 4-8 mg/mL.
6. A method for detecting 3-MCPD based on fluorescence analysis and catechol according to claim 1 or 2, characterized in that: the concentration of the polyethyleneimine solution in the step (2) is 5-6 mg/mL.
7. A method for detecting 3-MCPD based on fluorescence analysis and catechol according to claim 3, wherein: when the sample to be detected is palm oil, the palm oil is pretreated before detection, and the treatment process is as follows:
(1) Palm oil was dissolved in isooctane at a mass to volume ratio of 0.1g to 0.5ml, and then added to H 2 SO 4 Mixing with n-propanol, performing ultrasonic treatment in 45 deg.C water bath for 15min after vortex mixing, adding 0.5 mol/L sodium methoxide solution for rapid hydrolysis for 3min, and rapidly adding n-heptane and 3.3% glacial acetic acid solution after hydrolysis is completed to terminate reaction; wherein the H is 2 SO 4 And n-propanol in a mixing volume ratio of 0.5%; the glacial acetic acid solution with the concentration of 3.3 percent is prepared by dissolving glacial acetic acid in NaCl solution with the concentration of 0.01 g/mL; the mass volume ratio of the palm oil to the sodium methoxide with the concentration of 0.5 mol/L is 0.1 g/1 ml; the mass volume ratio of the palm oil to the n-heptane is 0.1 g/3 ml; the mass volume ratio of the palm oil to the glacial acetic acid with the concentration of 3.3% is 0.1 g/3 ml;
(2) Removing an upper organic phase after full reaction in the step (1), extracting twice by using n-heptane, removing residual nonpolar components in the solution, and taking a lower aqueous phase as a sample detection solution of palm oil; the mass-to-volume ratio of palm oil to n-heptane at each extraction was 0.1 g/3 ml.
8. A method for detecting 3-MCPD based on fluorescence analysis and catechol according to claim 3, wherein when the sample to be detected is soy sauce, the soy sauce is subjected to pretreatment before detection, and the treatment process is as follows: adding 5mol/L NaCl solution into the finished soy sauce according to the mass-volume ratio of 2g to 3ml, mixing, loading the mixture into a solid phase extraction column, eluting with a hexane-diethyl ether mixed solution, eluting with diethyl ether, collecting diethyl ether eluent, removing solvent, adding water into a centrifuge tube, and shaking uniformly to obtain a soy sauce sample detection solution; wherein the hexane-diethyl ether mixed solution is prepared by mixing according to the volume ratio of 9:1; the mass volume ratio of the soy sauce to the hexane-diethyl ether mixed solution is 1g to 10ml; the mass-volume ratio of the soy sauce to the diethyl ether is 2g to 75ml; the mass volume ratio of the soy sauce to the water is 1g to 0.25ml.
9. A method for detecting 3-MCPD based on fluorescence analysis and catechol according to claim 3, wherein: when the sample to be detected is tap water, the tap water sample is centrifuged at a high speed before detection, and the supernatant is filtered by a 0.45um filter membrane to obtain a tap water sample detection solution.
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