CN109725088B - Gas chromatography-mass spectrometry combined method for measuring 2-naphthoic acid and derivatives thereof in bean sprouts - Google Patents
Gas chromatography-mass spectrometry combined method for measuring 2-naphthoic acid and derivatives thereof in bean sprouts Download PDFInfo
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Abstract
The invention relates to a trace substance analysis and detection method, in particular to a gas chromatography-mass spectrometry combined method for measuring trace 2-naphthoic acid, 1-hydroxy-2-naphthoic acid and 4-methyl-2-naphthoic acid in bean sprouts. The method comprises the steps of enriching a target compound in bean sprout extracting solution by using a novel adsorbent 2-naphthalenesulfonate-magnesium-aluminum type hydrotalcite, dissolving the adsorbent by using an acid to realize complete elution of the target compound, efficiently extracting the compound by using a small amount of organic solvent, and rapidly analyzing and determining by using a gas chromatography-mass spectrometry combination method after methyl esterification and derivatization. The novel adsorbent adopted by the method realizes the rapid and efficient adsorption of the target object by adopting a dispersed solid phase extraction mode, has the advantages of rapidness and high efficiency, can realize the complete desorption of the target object by applying the acid-soluble adsorbent, and has novel method and simple and convenient operation. The method can better solve the problem of simultaneous detection of trace 2-naphthoic acid and two derivatives thereof in the bean sprout matrix.
Description
Technical Field
The invention relates to a method for analyzing and detecting trace substances, in particular to a gas chromatography-mass spectrometry combined method for measuring trace 2-naphthoic acid, 1-hydroxy-2-naphthoic acid and 4-methyl-2-naphthoic acid in bean sprouts.
Background
2-naphthoic acid, 1-hydroxy-2-naphthoic acid and 4-methyl-2-naphthoic acid are three common chemical products, wherein 2-naphthoic acid is commonly used as a plant growth regulator, 1-hydroxy-2-naphthoic acid and 4-methyl-2-naphthoic acid can be used as important organic intermediates of engineering plastics, organic pigments, liquid crystal materials and medicines as derivatives of 2-naphthoic acid, and the using amount in industrial and agricultural production is large. The 2-naphthoic acid and the two derivatives have the molecular structure of carboxyl, have larger polarity and stronger compatibility with plants rich in water, and when the 2-naphthoic acid is mixed into the two derivatives to be used as a plant growth agent, the 2-naphthoic acid can pollute the plants and can stably and durably exist on the surface and in the body of the plants.
Currently, few reports about analysis and detection methods of 2-naphthoic acid compounds only relate to a method for measuring the content of wastewater and chemical raw materials by using a small amount of high performance liquid chromatography, no report related to food matrixes exists, and a corresponding pretreatment method aiming at more complex food matrixes is obviously lacked.
Layered Double Hydroxide (LDHs) or pillared hydrotalcite compounds are typical Layered materials with supramolecular intercalation structures, and in the field of application of LDHs and roasted products thereof as adsorbents, different intercalation anions can be selected to synthesize different types of modified LDHs materials according to various factors such as molecular size, structure, polarity, functional groups and the like of adsorbed targets. The modified LDHs materials have different interlayer spacing, so that the modified LDHs materials have the adsorption selection effect of limiting the molecules of a specific target substance to enter the interlayer; meanwhile, the modified material intercalation anions have different replacement difficulty degrees, so that the modified material intercalation anions show different adsorption selectivity on different targets. In practical application, the adsorption effect of different LDHs materials and roasted products thereof on specific target objects needs to be selected, verified and optimized through adsorption experiments.
The inventor carries out adsorption experiments on the three substances in water by using the 2-naphthalenesulfonate-magnesium-aluminum type hydrotalcite adsorbent in previous researches, and the result shows that the 2-naphthalenesulfonate-magnesium-aluminum type hydrotalcite adsorbent has a good adsorption effect on a target object. On the basis, the inventor further optimizes the performance and application method of the developed adsorbent for enriching the target compound in the bean sprout extracting solution, and establishes a gas chromatography-mass spectrometry combined method for detecting three trace 2-naphthoic acid substances in the bean sprout matrix by using 2-naphthalenesulfonate-magnesium-aluminum type hydrotalcite as the adsorbent.
Disclosure of Invention
In order to overcome the defect that no method for simultaneously detecting 2-naphthoic acid and derivatives thereof in a food matrix is lacked at present, the invention aims to solve the technical problem of providing a gas chromatography-mass spectrometry combined method which is based on novel adsorbent dispersed solid phase extraction and is suitable for simultaneously detecting 2-naphthoic acid and two derivatives thereof in bean sprouts.
The invention achieves the above object by the following technical means.
A gas chromatography-mass spectrometry combined method for measuring 2-naphthoic acid and derivatives thereof in bean sprouts comprises the following steps:
step 1 extraction and adsorption of the compound: pulverizing bean sprout sample into paste, sealing at 4 deg.C for storage, weighing 10.00g sample in plastic centrifuge tube with plug, adding 2.0g anhydrous sodium chloride and 20mL ethyl acetate, homogenizing at high speed, centrifuging, collecting supernatant, extracting again, and mixing the supernatant; adding 0.40g of 2-naphthalenesulfonate-magnesium-aluminum type hydrotalcite adsorbent into the extracting solution, and oscillating for a certain time to make the adsorbent adsorb the target compound in the extracting solution;
desorption and extraction of the compound in the step 2: centrifuging the centrifuge tube, separating solid adsorbent from extractive solution, removing supernatant, adding a certain amount of hydrochloric acid solution, anhydrous sodium sulfate and organic extractant, dissolving the adsorbent layer by vortex to desorb compound, and oscillating for a certain time to complete extraction;
analytical testing of the compound of step 4: concentrating the solution at 40 ℃ till the solution is nearly dry, adding 2.00mL of ethyl acetate for constant volume, carrying out vortex, absorbing the upper layer of organic solution, filtering, and carrying out analysis and test by using a gas chromatography-mass spectrometry combined method according to the following conditions:
a) a chromatographic column: DB-5MS capillary column, 30m × 0.25mm, 0.25 μm thick; column flow rate: 1.50 mL/min.
b) Sample inlet temperature: 220 ℃; and (3) sample introduction mode: no shunt sampling; sample introduction amount: 2 μ L.
c) Temperature rising procedure: 60 deg.C (keeping 1min), heating to 120 deg.C at a rate of 10 deg.C/min (keeping 1min), heating to 150 deg.C at a rate of 5 deg.C/min (keeping 1min), and heating to 250 deg.C at a rate of 30 deg.C/min (keeping 1 min).
d) EI bombardment source: 70 ev; temperature of a chromatography-mass spectrometry connection port: 280 ℃; temperature of the quadrupole rods: 230 ℃; ion source temperature: at 150 ℃.
e) Carrier gas: high-purity helium (the purity is more than or equal to 99.999%).
f) Mass spectrum data acquisition mode: selected ion scan mode (SIM), solvent delay time: and 6 min.
g) The quantitative and qualitative ion of the compounds are given in the following table:
| serial number | Name of Compound | Quantitative ion | Qualitative ion |
| 1 | 2-naphthoic acid derivatives | 155.0 | 127.0，186.0 |
| 2 | 1-hydroxy-2-naphthoic acid derivatives | 170.0 | 202.0，114.0 |
| 3 | 4-methyl-2-naphthoic acid derivatives | 169.0 | 141.1，200.1 |
Wherein the content of the first and second substances,
the high-speed homogenizing extraction in the step 1 has the homogenizing speed of 12000rpm to 15000rpm, the homogenizing time of 3min to 5min and the oscillating adsorption time of 5min to 10 min.
The hydrochloric acid solution in the step 2 is prepared by concentrated hydrochloric acid and water according to the volume ratio of 1:1, the dosage is 3.00mL, the added anhydrous sodium sulfate is 2.0g, the organic extraction solvent is 5.00mL of methyl tert-butyl ether, and the oscillation extraction time is 5min to 10 min.
In the step 3, 0.1g to 0.2g of ammonium carbonate is added, a derivatization reagent is 0.4mL of methanol and 0.1mL of trimethylsilylated diazomethane n-hexane solution with the concentration of 2moL/L, the water bath temperature is 30 ℃ to 50 ℃, and the derivatization time is 30min to 60 min.
In the above step, the filter membrane is an organic phase filter membrane with pore diameter of 0.22 μm, the vortex time is 1 min-2 min, and the centrifugation is carried out for 3min at 4500 rpm.
The method of the invention needs to be explained in the research process:
in the process of research and development of the method, the inventor takes three targets as adsorption objects and utilizes a plurality of synthesized LDHs materials and roasting products thereof to investigate the adsorption performance of the LDHs materials, screens out adsorbents with good adsorption effect on the targets, and selects and optimizes the dosage of the adsorbents and the selection and the proportion of extraction solvents; meanwhile, a derivatization method of the target substance is selected; in addition, the selection and optimization of chromatographic separation conditions, the selection and optimization of mass spectrum conditions, the selectivity and anti-interference of quantitative and qualitative ions and other factors are investigated and optimized, and a relatively excellent detection method is provided on the basis.
In consideration of quantitative accuracy of the target object, the method quantifies the target object by adopting the matrix correction curve on the premise that the isotope of the target object cannot be obtained so as to quantify the target object by an isotope internal standard method, so that systematic errors are eliminated as much as possible, and the quantitative accuracy is improved.
The invention has the advantages that:
(1) the novel adsorbent 2-naphthalenesulfonate-magnesium-aluminum type hydrotalcite adopted by the invention can be used for rapidly adsorbing three trace naphthoic acid compounds in bean sprout extracting solution by adopting a dispersed solid phase extraction mode, and has the advantages of rapidness and high efficiency;
(2) the invention utilizes the characteristic that the 2-naphthalenesulfonate-magnesium-aluminum type hydrotalcite adsorbent can be dissolved in acid, and uses hydrochloric acid solution to dissolve the adsorbent after adsorbing the target object, so that the target object can be completely desorbed from the adsorbent.
Drawings
FIG. 1 is a chromatogram of a matrix standard solution of 2-naphthoic acid, 1-hydroxy-2-naphthoic acid and 4-methyl-2-naphthoic acid at a concentration of 200.0. mu.g/L, wherein 1 is 2-naphthoic acid, 2 is 1-hydroxy-2-naphthoic acid and 3 is 4-methyl-2-naphthoic acid, in accordance with an embodiment.
Detailed Description
For further disclosure, but not limitation, the present invention is described in further detail below with reference to examples.
(1) The reagent medicines involved in the embodiments of the present invention are as follows:
2-naphthoic acid, 1-hydroxy-2-naphthoic acid and 4-methyl-2-naphthoic acid, wherein the purity of the solid standard is more than or equal to 98.0 percent, Beijing Bailingwei science and technology limited;
methanol, ethyl acetate, anhydrous sodium sulfate, sodium chloride, methyl tert-butyl ether, ethyl acetate, analytically pure, group of national medicine;
hydrochloric acid, super pure, group of national medicine; the water is first-grade water meeting the GB/T6682 specification.
Trimethylsilyldiazomethane solution, 2.0M in hexane, Alfa Aesar.
(2) The instruments involved in the examples of the present invention are as follows:
KH-75A type electric heating constant temperature air-blast drying oven, Kangheng instruments ltd, Guangzhou;
IKA T25 type high speed refiner, IKA technologies, Inc., Germany;
model 7890B-5977A gas chromatography-mass spectrometer with electron bombardment source (EI), Agilent technologies, Inc., USA.
(3) Analyzing and testing conditions by a gas chromatography-mass spectrometer:
a) a chromatographic column: DB-5MS capillary column, 30m × 0.25mm, 0.25 μm thick; column flow rate: 1.50 mL/min.
b) Sample inlet temperature: 220 ℃; and (3) sample introduction mode: no shunt sampling; sample introduction amount: 2 μ L.
c) Temperature rising procedure: 60 deg.C (keeping 1min), heating to 120 deg.C at a rate of 10 deg.C/min (keeping 1min), heating to 150 deg.C at a rate of 5 deg.C/min (keeping 1min), and heating to 250 deg.C at a rate of 30 deg.C/min (keeping 1 min).
d) EI bombardment source: 70 ev; temperature of a chromatography-mass spectrometry connection port: 280 ℃; temperature of the quadrupole rods: 230 ℃; ion source temperature: at 150 ℃.
e) Carrier gas: high-purity helium (the purity is more than or equal to 99.999%).
f) Mass spectrum data acquisition mode: selected ion scan mode (SIM), solvent delay time: and 6 min.
g) The quantitative and qualitative ion of the compounds are given in the following table:
| serial number | Name of Compound | Quantitative ion | Qualitative ion |
| 1 | 2-naphthoic acid derivatives | 155.0 | 127.0，186.0 |
| 2 | 1-hydroxy-2-naphthoic acid derivatives | 170.0 | 202.0，114.0 |
| 3 | 4-methyl-2-naphthoic acid derivatives | 169.0 | 141.1，200.1 |
(4) Preparation of matrix calibration curve and determination of detection limit and quantitative limit
Accurately weighing the 2-naphthoic acid, the 1-hydroxy-2-naphthoic acid and the 4-methyl-2-naphthoic acid, dissolving the materials in methanol to a constant volume, and preparing a standard stock solution with the concentration of 1000mg/L for storage at the temperature of-4 ℃. When in use, the standard stock solution is gradually diluted by deionized water to prepare standard use solution with the concentration gradient of 10.0 mug/L, 20.0 mug/L, 40.0 mug/L, 100.0 mug/L and 200.0 mug/L.
(I) Extraction and adsorption of the compounds: crushing bean sprout samples into paste, sealing and storing at 4 ℃, taking five 50mL plastic centrifuge tubes with plugs when in use, respectively weighing 10.00g of samples, respectively adding 2.00mL of the standard use solution, whirling and standing for 2h, then adding 2.0g of anhydrous sodium chloride and 20mL of ethyl acetate, homogenizing and extracting at a high speed of 12000rpm for 3min, centrifuging, taking supernatant into another centrifuge tube with a plug, re-extracting once, and combining the upper-layer extracting solution; adding 0.40g of 2-naphthalenesulfonate-magnesium-aluminum type hydrotalcite adsorbent into the extract, and oscillating for 10min to make the adsorbent adsorb the target compound in the extract;
(II) desorption and extraction of the compound: centrifuging the centrifuge tube, separating solid adsorbent from extractive solution, removing supernatant, adding 3.00mL hydrochloric acid solution, 2.0g anhydrous sodium sulfate and 5mL methyl tert-butyl ether extractant, dissolving adsorbent layer by vortex to desorb compound, and shaking for 10min to complete extraction;
(III) extraction and derivatization of compounds: centrifuging the centrifuge tube, separating the supernatant into derivative bottles, adding 0.2g of ammonium carbonate, swirling, adding 0.4mL of methanol and 0.1mL of trimethylsilylated diazomethane n-hexane solution with the concentration of 2moL/L, sealing, mixing uniformly, and derivatizing at 30 ℃ for 30 min;
(IV) analytical testing of Compounds: concentrating the solution at 40 deg.C, adding 2.00mL ethyl acetate to desired volume, vortexing, absorbing the upper organic solution, filtering with organic phase filter membrane with pore diameter of 0.22 μm, and analyzing by gas chromatography-mass spectrometry.
Taking the concentration of 2-naphthoic acid, 1-hydroxy-2-naphthoic acid and 4-methyl-2-naphthoic acid in a sample solution as an X axis, and taking the peak area of a chromatographic peak of a derivative of the 2-naphthoic acid, the 1-hydroxy-2-naphthoic acid and the 4-methyl-2-naphthoic acid on a gas chromatography-mass spectrometer as a Y axis to draw a matrix standard curve and use the matrix standard curve for external standard method quantification.
The triple value of the signal-to-noise ratio S/N is taken as the detection limit of the method (LOD, LOD is 3S/N), the ten times of the signal-to-noise ratio S/N is taken as the quantification limit of the method (LOQ, LOQ is 10S/N), and the detection limit and the quantification limit of each compound in water are calculated by combining the volume of the added matrix.
The relevant parameters of the matrix standard curve, LOD and LOQ are shown in Table 1.
TABLE 1 preparation of three naphthoic acids
Information related to matrix standard curve, detection limit and quantification limit
(5) Synthesis of 2-naphthalenesulfonate-magnesium-aluminum type hydrotalcite adsorbent
In order to enable those skilled in the art to repeatedly carry out the relevant experiments of the present invention, a method for synthesizing the key substance 2-naphthalenesulfonate-magnesium aluminum type hydrotalcite adsorbent used in the present invention is now provided, as follows:
the reagent and the drug related to the synthesis of the adsorbent are as follows:
2-sodium naphthalene sulfonate, analytically pure, group of national medicine;
Mg6Al2(OH)16CO3·4H2o, analytical grade, Aldrich, usa.
② the apparatus related to the synthesis of the adsorbent is as follows:
an EXCEL type microwave digestion instrument, Shanghai Yao Instrument science and technology development Co., Ltd., digestion tank volume of 100 mL; microwave muffle furnace (sintering furnace), CEM corporation, usa; model VD53 vacuum drying cabinet, German Bindd technologies; HJ-5 multifunctional constant temperature stirrer, Kantai Ronghua Instrument manufacturing Co., Ltd; FS-12 type separatory funnel oscillator, New optical technology, Japan; 3K-15 type centrifuge, sigma technologies, germany; BF518945C-1 model box resistance furnace (muffle furnace), Saimer Feishell science, USA.
The concrete steps of synthesizing the adsorbent are as follows:
(a) roasting: mg of purchased Mg-Al type hydrotalcite6Al2(OH)16CO3·4H2Placing O in a muffle furnace, heating at a heating rate of 5 ℃/min to 500 ℃, and roasting for 6h to obtain a roasted product Mg6Al2O8(OH)2；
(b) Weighing: 6.90g of intercalation agent 2-sodium naphthalenesulfonate and 7.236g of roasting product are weighed in a microwave digestion tankSubstance Mg6Al2O8(OH)2。
(c) Microwave crystallization hydrothermal synthesis: boiling deionized water and keeping for 30min, adding 100mL into the microwave digestion tank filled with the intercalation agent and the roasting product, sealing, placing the microwave digestion tank into a microwave digestion instrument, and performing microwave heating at 150 ℃ for 30min to complete synthesis;
(d) washing and drying: pouring out all solids and liquid in the microwave tank, heating and stirring with deionized water boiled for more than 30min to remove carbon dioxide, shaking, washing, centrifuging, vacuum drying at 90 deg.C for 12h, grinding, and storing.
Example 1
In this example 1, soybean sprouts were used as a sample matrix to perform a labeling recovery experiment to verify the feasibility of the method of the present invention, and the sample was purchased from Fuqing Yonghui supermarket and processed according to the following steps:
(1) extraction and adsorption of the compounds: crushing a bean sprout sample into paste, sealing and storing at 4 ℃, taking 50mL of plastic centrifuge tubes with plugs when in use, respectively weighing 10.00g of the sample, respectively adding 2.00mL of three compound standard solutions with the concentrations of 10.0 mu g/L, 20.0 mu g/L and 200.0 mu g/L to prepare a three-level six-parallel standard sample, adding 2.0g of anhydrous sodium chloride and 20mL of ethyl acetate after vortex standing for 2h, homogenizing and extracting at a high speed of 12000rpm for 3min, centrifuging, taking supernatant into another centrifuge tube with a plug, re-extracting once, and combining the upper-layer extracting solution; adding 0.40g of 2-naphthalenesulfonate-magnesium-aluminum type hydrotalcite adsorbent into the extract, and oscillating for 5min to make the adsorbent adsorb the target compound in the extract;
(2) desorption and extraction of the compound: centrifuging the centrifuge tube, separating solid adsorbent from extractive solution, removing supernatant, adding 3.00mL hydrochloric acid solution, 2.0g anhydrous sodium sulfate and 5mL methyl tert-butyl ether extractant, dissolving adsorbent layer by vortex to desorb compound, and shaking for 5min to complete extraction;
(3) extraction and derivatization of compounds: centrifuging the centrifuge tube, separating the supernatant into derivative bottles, adding 0.1g of ammonium carbonate, swirling, adding 0.4mL of methanol and 0.1mL of trimethylsilylated diazomethane n-hexane solution with the concentration of 2moL/L, sealing, mixing uniformly, and derivatizing at 30 ℃ for 30 min;
(4) analytical testing of compounds: concentrating the solution at 40 deg.C, adding 2.00mL ethyl acetate to desired volume, vortexing, absorbing the upper organic solution, filtering with organic phase filter membrane with pore diameter of 0.22 μm, and analyzing by gas chromatography-mass spectrometry.
The parameters relevant to the spiking recovery experiment of example 1 are shown in Table 2.
Table 2 experimental data on addition concentration and recovery rate of soybean sprout sample (n ═ 6)
Example 2
In this example 2, mung bean sprouts were used as a sample matrix to perform a labeling recovery experiment to verify the feasibility of the method of the present invention, and the sample was purchased from Fuqing Yonghui supermarket and processed according to the following steps:
(1) extraction and adsorption of the compounds: crushing a bean sprout sample into paste, sealing and storing at 4 ℃, taking 50mL of plastic centrifuge tubes with plugs when in use, respectively weighing 10.00g of the sample, respectively adding 2.00mL of three compound standard solutions with the concentrations of 10.0 mu g/L, 20.0 mu g/L and 200.0 mu g/L to prepare a three-level six-parallel standard sample, adding 2.0g of anhydrous sodium chloride and 20mL of ethyl acetate after vortex standing for 2h, homogenizing and extracting at a high speed of 15000rpm for 5min, centrifuging, taking supernatant into another centrifuge tube with a plug, re-extracting once, and combining the upper-layer extracting solution; adding 0.40g of 2-naphthalenesulfonate-magnesium-aluminum type hydrotalcite adsorbent into the extract, and oscillating for 10min to make the adsorbent adsorb the target compound in the extract;
(2) desorption and extraction of the compound: centrifuging the centrifuge tube, separating solid adsorbent from extractive solution, removing supernatant, adding 3.00mL hydrochloric acid solution, 2.0g anhydrous sodium sulfate and 5mL methyl tert-butyl ether extractant, dissolving adsorbent layer by vortex to desorb compound, and shaking for 5min to complete extraction;
(3) extraction and derivatization of compounds: centrifuging the centrifuge tube, collecting supernatant, adding 0.2g ammonium carbonate, vortexing, adding 0.4mL methanol and 0.1mL trimethylsilyl diazomethane n-hexane solution with concentration of 2moL/L, sealing, mixing, and derivatizing at 50 deg.C for 60 min;
(4) analytical testing of compounds: concentrating the solution at 40 deg.C, adding 2.00mL ethyl acetate to desired volume, vortexing, absorbing the upper organic solution, filtering with organic phase filter membrane with pore diameter of 0.22 μm, and analyzing by gas chromatography-mass spectrometry.
The parameters relevant to the spiking recovery experiment of example 2 are shown in Table 3.
TABLE 3 Green bean sprouts samples with concentrations added and recovery rates (n ═ 6)
The above-mentioned embodiments only express the embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the spirit of the invention, which falls within the scope of the invention, and therefore the scope of the patent of the invention shall be governed by the appended claims.
Claims (5)
1. A gas chromatography-mass spectrometry combined method for measuring 2-naphthoic acid and derivatives thereof in bean sprouts, in particular to a method for simultaneously measuring trace 2-naphthoic acid, 1-hydroxy-2-naphthoic acid and 4-methyl-2-naphthoic acid in bean sprouts, which is characterized by comprising the following steps:
(1) extraction and adsorption of the compounds: pulverizing bean sprout sample into paste, sealing at 4 deg.C for storage, weighing 10.00g sample in plastic centrifuge tube with plug, adding 2.0g anhydrous sodium chloride and 20mL ethyl acetate, homogenizing at high speed, centrifuging, collecting supernatant, extracting again, and mixing the supernatant; adding 0.40g of 2-naphthalenesulfonate-magnesium-aluminum type hydrotalcite adsorbent into the extracting solution, and oscillating for a certain time to make the adsorbent adsorb the target compound in the extracting solution;
(2) desorption and extraction of the compound: centrifuging the centrifuge tube, separating solid adsorbent from extractive solution, removing supernatant, adding a certain amount of hydrochloric acid solution, anhydrous sodium sulfate and organic extractant, dissolving the adsorbent layer by vortex to desorb compound, and oscillating for a certain time to complete extraction;
(3) extraction and derivatization of compounds: centrifuging the centrifugal tube, separating supernatant into derivatization bottles, adding ammonium carbonate into the derivatization bottles, carrying out vortex, adding a derivatization reagent, sealing, uniformly mixing, and putting into a constant-temperature water bath to complete a derivatization process;
(4) analytical testing of compounds: concentrating the solution at 40 ℃ till the solution is nearly dry, adding 2.00mL of ethyl acetate for constant volume, carrying out vortex, absorbing the upper layer of organic solution, filtering, and carrying out analysis and test by using a gas chromatography-mass spectrometry combined method according to the following conditions:
a) a chromatographic column: DB-5MS capillary column, 30m × 0.25mm, 0.25 μm thick; column flow rate: 1.50 mL/min;
b) sample inlet temperature: 220 ℃; and (3) sample introduction mode: no shunt sampling; sample introduction amount: 2 mu L of the solution;
c) temperature rising procedure: keeping at 60 deg.C for 1min, heating to 120 deg.C at a speed of 10 deg.C/min for 1min, heating to 150 deg.C at a speed of 5 deg.C/min for 1min, heating to 250 deg.C at a speed of 30 deg.C/min for 1 min;
d) EI bombardment source: 70 ev; temperature of a chromatography-mass spectrometry connection port: 280 ℃; temperature of the quadrupole rods: 230 ℃; ion source temperature: 150 ℃;
e) carrier gas: high-purity helium with the purity more than or equal to 99.999 percent;
f) mass spectrum data acquisition mode: selection of ion scan mode, solvent delay time: 6 min;
g) the quantitative and qualitative ion of the compounds are given in the following table:
。
2. The combination of gas chromatography-mass spectrometry for measuring 2-naphthoic acid and its derivatives in bean sprouts as claimed in claim 1, wherein the high speed homogenizing extraction in step (1) is carried out at a homogenizing speed of 12000rpm to 15000rpm for 3min to 5min and with a shaking adsorption time of 5min to 10 min.
3. The gas chromatography-mass spectrometry combination method for determining 2-naphthoic acid and derivatives thereof in bean sprouts as claimed in claim 1, wherein the hydrochloric acid solution in step (2) is prepared from concentrated hydrochloric acid and water according to a volume ratio of 1:1, the amount of the hydrochloric acid solution is 3.00mL, 2.0g of anhydrous sodium sulfate is added, 5.00mL of methyl tert-butyl ether is used as an organic extraction solvent, and the shaking extraction time is 5min to 10 min.
4. The gas chromatography-mass spectrometry combination for measuring 2-naphthoic acid and its derivatives in bean sprouts as claimed in claim 1, wherein the amount of ammonium carbonate in step (3) is 0.1g to 0.2g, the derivatization reagent is 0.4mL methanol and 0.1mL trimethylsilyl diazomethane n-hexane solution with concentration of 2moL/L, the water bath temperature is 30 ℃ to 50 ℃, and the derivatization time is 30min to 60 min.
5. The gas chromatography-mass spectrometry combined method for measuring 2-naphthoic acid and its derivatives in bean sprouts as claimed in claim 1, wherein the filtration membrane is an organic phase filtration membrane with a pore size of 0.22 μm, a vortex time of 1min to 2min, and a centrifugation of 3min at 4500 rpm.
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