CN110455939B - Method for detecting stearoyl lactylate in flour or flour improver - Google Patents
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Abstract
The invention provides a method for detecting stearoyl lactylate in flour or a flour improver, which combines the property characteristics of the flour or the flour improver, selects a proper chromatographic column aiming at a compound to be detected stearoyl lactylate, enriches and separates the stearoyl lactylate in a sample under proper chromatographic conditions, obtains good chromatographic peak shape and retention time, has sensitive response and is used for qualitatively or quantitatively detecting the hard early lactylate in the flour or the flour improver. Moreover, the detection method is suitable for qualitative or quantitative detection of the stearoyl lactylate in the food or the food additive, and can effectively eliminate the interference of other substances in the food sample.
Description
Technical Field
The invention belongs to the field of analytical chemistry, and particularly relates to a method for detecting stearoyl lactylate in flour or a flour modifier.
Background
Sodium stearoyl lactylate, also known as sodium stearoyl lactylate, abbreviated as SSL, is multifunctional sodium stearoyl lactylate with excellent performance, is powder at normal temperature, is specified in the national food additive use standard (GB2760-2014), and can be used as an emulsifier and a stabilizer in dairy products such as prepared milk, decorative candies, special wheat flour, raw and wet flour products, bread and cakes.
At present, there is no method for detecting the content of stearoyl lactylate in flour or flour improver, but two existing methods, namely a titration method and a spectrophotometry method, are used for determining the purity of stearoyl lactylate in pure products, and when the method is applied to the detection of stearoyl lactylate in flour or flour improver, the detection accuracy is easily interfered by the existence of matrix in flour or flour improver, so that a method for detecting the content of stearoyl lactylate in food with high accuracy by effectively reducing the matrix interference is needed.
Disclosure of Invention
Based on the above, the invention aims to provide a method for detecting the content of stearoyl lactylate in flour or flour improver, which can effectively reduce matrix interference and has high accuracy.
In order to achieve the purpose, the specific technical scheme of the invention is as follows:
a method for detecting stearoyl lactylate in flour or a flour improver comprises the following steps:
pretreatment: adding an organic solvent into a flour or flour improver sample to be detected, extracting, and taking the supernatant to obtain a test sample solution;
and (3) detection: detecting the test solution by adopting a high performance liquid chromatography tandem mass spectrometer;
in the detection, chromatographic conditions comprise:
the chromatographic column is selected from HILIC chromatographic column and C18Chromatography column or C8A chromatographic column;
the mobile phase is formed by mixing the mobile phase A and the mobile phase B according to the volume ratio of (3:97) - (10:90), and the flow rate is 0.1-0.5 mL/min;
the mobile phase A is ammonia water or ammonium acetate solution, and the mobile phase B is acetonitrile.
The invention also provides the application of the method for detecting the stearoyl lactylate in the food in the qualitative or quantitative detection of the stearoyl lactylate in the food.
Based on the technical scheme, the invention has the following beneficial effects:
the method adopts a high performance liquid chromatography tandem mass spectrometry method for the first time, combines the property characteristics of the flour or the flour improver, selects a proper chromatographic column aiming at the compound stearoyl lactylate to be detected, enriches and separates the stearoyl lactylate in a sample under proper chromatographic conditions, obtains good chromatographic peak pattern and retention time, has sensitive response, is used for qualitatively or quantitatively detecting the hard early lactylate in the flour or the flour improver, and has the characteristics of low detection limit and quantitative limit, low recovery rate and high precision. The detection limit can be as low as 0.03mg/L, and the quantification limit can be as low as 0.5 mg/L. Moreover, the detection method is suitable for qualitative or quantitative detection of the stearoyl lactylate in the food or the food additive, and can effectively eliminate the interference of other substances in the food sample.
Drawings
FIG. 1 is a chromatogram of a standard use solution as described in example 1;
FIG. 2 is a chromatogram of a wheat flour sample (negative sample) containing no stearoyl lactylate in example 2;
FIG. 3 is a chromatogram of a negative wheat flour sample of example 3 with the addition of stearoyl lactylate at a concentration of 1.0 mg/kg;
FIG. 4 is a chromatogram of a wheat flour improver sample (negative sample) without stearoyl lactylate in example 4;
FIG. 5 is a chromatogram of a sample of a negative wheat flour improver containing 1.0mg/kg of stearoyl lactylate in example 5.
FIG. 6 is a standard graph of example 7.
Detailed Description
In order that the invention may be more readily understood, reference will now be made to the following more particular description of the invention, examples of which are set forth below. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. These embodiments are provided so that this disclosure will be thorough and complete. It is to be understood that the experimental procedures in the following examples, where specific conditions are not noted, are generally in accordance with conventional conditions, or with conditions recommended by the manufacturer. The various reagents used in the examples are commercially available.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.
The invention discloses a method for detecting stearoyl lactylate in flour or a flour improver, which comprises the following steps:
pretreatment: adding an organic solvent into a flour or flour improver sample to be detected, extracting, and taking the supernatant to obtain a test sample solution;
and (3) detection: and detecting the test solution by adopting a high performance liquid chromatography tandem mass spectrometer.
Preferably, in the detection, the chromatographic column used in the high performance liquid chromatography tandem mass spectrometer is selected from: HILIC chromatographic column, C18Chromatography column and C8More preferably, the HILIC chromatographic column has a model of 50mm × 4.6.6 mm × 2.6.6 μm18Chromatography column and C8During chromatographic column, the retention time of the target is shorter within 0.7min, and the method is only suitable for qualitative detection, while the HILIC chromatographic column can obtain better chromatographic peak type and retention time under the condition of adopting a high-proportion organic phase (such as 94-96 percent), can be used for qualitative detection, is also suitable for quantitative detection, and has high accuracy of detection results.
Preferably, in the assay, the chromatographic conditions comprise: mixing the mobile phase A and the mobile phase B in a volume ratio of (3:97) - (10:90), wherein the flow rate of the mobile phase is 0.1-0.5 mL/min. More preferably, mobile phase A is mixed with mobile phase B in a volume ratio of (4:96) - (6:94) and the flow rate of the mobile phase is 0.1-0.3 mL/min. Further preferably, the volume ratio of the mobile phase A to the mobile phase B is 5:95, and the flow rate of the mobile phase is 0.2 mL/min.
Preferably, the mobile phase A is ammonia water or ammonium acetate solution; the mobile phase B is acetonitrile. Preferably, the mobile phase a is ammonia. More preferably, the mobile phase a is 0.05% to 0.15% ammonia. More preferably 0.1. + -. 0.01% ammonia. The inventor finds that under the condition that the mobile phase A and the mobile phase B are matched in a proper proportion, the mobile phase A adopts ammonia water, so that ionization of sodium stearoyl lactate can be promoted, the response strength of stearoyl lactate in a negative ion source mode is enhanced, quantitative detection is facilitated, and the detection sensitivity is improved. In the detection method of the invention, the detection effect of adding the ammonium acetate solution is not as good as that of ammonia water, because the ammonium acetate is found to inhibit the response of molecular ion peaks under liquid condition.
Preferably, in the detecting, the mass spectrometry conditions include:
an ion source: electrospray ion, negative ion mode;
ion source temperature: 450 ℃ and 550 ℃;
atomizing: 18-22 psi; auxiliary gas: 3-7 psi; air curtain air: 18-22 psi;
the scanning mode is as follows: multiple reaction monitoring mode.
More preferably, in the multiple reaction monitoring mode, the monitoring ion pair is: m/z 355.4 is more than 283, m/z 355.4 is more than 89; the quantitative ion pair is: m/z 355.4 is more than 283. By adopting the mass spectrum conditions and selecting proper monitoring ion pairs and quantitative ion pairs, the liquid chromatography tandem mass spectrum realizes the qualitative and quantitative determination of the compound through the ion fragments with structural information, and the ion fragments are monitored by an instrument through converting into mass-to-charge ratios. Interferents are excluded by not containing a specific mass-to-charge ratio. Therefore, the interference can be further eliminated, and the detection accuracy can be ensured.
Preferably, in the sample pretreatment, the organic solvent is acetonitrile. The acetonitrile is the same as the component B of the mobile phase, and is helpful for improving the chromatographic peak pattern of the detected compound of sodium stearoyl lactylate.
Optionally, the method for detecting stearoyl lactylate further comprises: preparing standard substance solutions with a series of concentrations, and detecting the standard substance solutions with the series of concentrations by adopting a high performance liquid chromatography tandem mass spectrometer; and drawing a standard curve, and calculating the concentration of the stearoyl lactylate in the sample to be detected according to the standard curve.
Preferably, the preparation method of the standard solutions with the series of concentrations comprises the following steps: accurately weighing sodium stearoyl lactate standard, dissolving with acetone, diluting with acetonitrile, and diluting to constant volume to obtain standard stock solution; and diluting the standard substance stock solution with acetonitrile and fixing the volume to obtain standard substance solutions with serial concentrations.
The invention also provides the use of the method for the detection of stearoyl lactylate as described above for the qualitative or quantitative detection of stearoyl lactylate in a food product.
In this application, optionally, the food product comprises: flour, flour improver, wheat flour or wheat flour improver.
The specific information of the reagents used in the examples of the present invention is as follows:
stearoyl lactylate standards: purities of greater than 99% were obtained from Alfa Aesar;
wheat flour: purchased in a local market;
and (3) flour modifying agent: the method comprises, but is not limited to, a special compound wheat flour treating agent, a bread improver, a bread soft improver and the like, wherein the special compound wheat flour treating agent and the bread improver are obtained from local markets in the embodiments 4 and 5 of the invention.
EXAMPLE 1 measurement of Standard solution of stearoyl lactylate
1) Preparing a stearoyl lactylate standard solution: weighing a proper amount of stearoyl lactylate standard, dissolving the stearoyl lactylate standard with acetone, and then diluting the volume to 10mL with acetonitrile to prepare a standard stock solution of stearoyl lactylate (with the concentration of stearoyl lactylate radical) with the concentration of 500 mg/L. Sucking 20 μ L of the stock solution into a 10mL container, diluting to 10mL, and preparing into a standard use solution of stearoyl lactylate with a concentration of 1 mg/kg.
2) Chromatographic conditions
A chromatographic column: HILIC chromatographic column (50 mm. times.4.6 mm. times.2.6 μm)
The column temperature is 40 ℃;
sample introduction amount: 1.0 μ L;
flow rate: 0.2 mL/min;
mobile phase: a is 0.1% ammonia water, B is acetonitrile; mobile phase ratio a: b is 5: 95.
3) conditions of Mass Spectrometry
An ion source: electrospray ion, negative ion (ESI-) mode;
capillary voltage 4.0 KV;
the ion source temperature was 500 c,
atomizing: 20 psi; auxiliary gas: 5 psi; air curtain air: 20 psi;
the scanning mode is as follows: multiple Reaction Monitoring (MRM) mode, monitoring ion pair m/z 355.4 > 283; m/z 355.4 > 89, and quantitative ion pair m/z 355.4 > 283.
4) The chromatogram of the standard use solution of 1.0mg/L stearoyl lactylate is shown in the attached figure 1, and the chromatogram shows a peak at 2.63 minutes.
The invention also adopts the conventional C18Chromatography column and C8The chromatographic column detects the stearoyl lactylate standard solution, and the rest of the chromatographic mass spectrum conditions are the same as those described above. By C18Chromatography column and C8The chromatographic column can generate peaks, the peak generating time (retention time) is less than 0.7min, the retention time is short, the peak shape is poor compared with the peak shape detected by adopting a HILIC chromatographic column, and the requirement of quantitative detection cannot be met.
Example 2 measurement of the content of stearoyl lactylate in a negative sample (wheat flour sample without stearoyl lactylate)
1) Preparation of test sample liquid
Weighing 1.0g (negative sample) of a wheat flour sample without stearoyl lactylate into a 15mL plastic centrifuge tube with a plug, adding 5.0mL of acetonitrile solution for extracting a substance to be detected in the sample, performing vortex oscillation for 2min, performing ultrasonic extraction for 10min, standing, and centrifuging 1mL of supernatant at 15000r/min for 5 min. The supernatant was aspirated and assayed.
2) Chromatographic conditions
Example 1 was performed as in example 1.
3) Conditions of Mass Spectrometry
Example 1 was performed as in example 1.
4) The chromatogram of the negative sample is shown in fig. 2, and it can be seen that the negative sample does not contain stearoyl lactylate, and therefore no peak is found in the chromatogram.
Example 3: measurement of stearoyl lactylate content in a negative sample (wheat flour sample without stearoyl lactylate) to which a stearoyl lactylate standard was added
1) Preparation of test sample liquid
1.0g of wheat flour sample without stearoyl lactylate is weighed into a 15mL plastic centrifuge tube with a plug, and 100. mu.L of stearoyl lactylate standard solution with the concentration of 10mg/L is added to make the sample contain 1mg/kg of stearoyl lactylate. Then adding 5.0mL of acetonitrile extract, carrying out vortex oscillation for 2min, carrying out ultrasonic extraction for 10min, standing, and centrifuging 1mL of supernatant at 15000r/min for 5 min. The supernatant was aspirated and assayed.
2) Chromatographic conditions
Example 1 was performed as in example 1.
3) Conditions of Mass Spectrometry
Example 1 was performed as in example 1.
4) As shown in FIG. 3, the chromatogram of the sample of the negative wheat flour with the addition of stearoyl lactylate at a concentration of 1.0mg/kg shows that the negative sample with the addition of stearoyl lactylate standard shows a peak at 2.62 minutes, the retention time and the peak intensity are basically the same as those of example 1, and stearoyl lactylate in the sample can be detected and is not interfered by the wheat flour.
Example 4: measurement of the content of stearoyl lactylate in negative samples (negative wheat flour improver without stearoyl lactylate)
1) Preparation of test sample liquid
Weighing 1.0g (negative sample) of a negative wheat flour improver sample without stearoyl lactylate into a 15mL plastic centrifuge tube with a plug, adding 5.0mL of acetonitrile extracting solution, carrying out vortex oscillation for 2min, carrying out ultrasonic extraction for 10min, standing, and centrifuging 1mL of supernatant for 5min at 15000 r/min. The supernatant was aspirated and assayed.
2) Chromatographic conditions
Example 1 was performed as in example 1.
3) Conditions of Mass Spectrometry
Example 1 was performed as in example 1.
4) The chromatogram of the negative sample is shown in FIG. 4, and it can be seen that the negative sample does not contain stearoyl lactylate, so no peak is found in the chromatogram.
Example 5: measurement of the content of stearoyl lactylate in a negative sample (a negative wheat flour improver without stearoyl lactylate) to which a stearoyl lactylate standard solution was added
1) Preparation of test sample liquid
1.0g (negative sample) of a negative wheat flour improver sample not containing stearoyl lactylate is weighed into a 15mL plastic centrifuge tube with a plug, and 100. mu.L of a stearoyl lactylate standard solution with the concentration of 10mg/L is added to make the sample contain 1mg/kg of stearoyl lactylate. Then adding 5.0mL of acetonitrile extract, carrying out vortex oscillation for 2min, carrying out ultrasonic extraction for 10min, standing, and centrifuging 1mL of supernatant at 15000r/min for 5 min. The supernatant was aspirated and assayed.
2) Chromatographic conditions
Example 1 was performed as in example 1.
3) Conditions of Mass Spectrometry
Example 1 was performed as in example 1.
4) As shown in FIG. 5, the chromatogram of the sample of the negative wheat flour improver added with the stearyl lactylate concentration of 1.0mg/kg shows that the negative sample added with the stearyl lactylate standard shows a peak at 2.62 minutes, the retention time and the peak intensity are basically the same as those of example 1, and the stearyl lactylate in the sample can be detected without being interfered by the wheat flour improver.
Example 6 Linear Range, Linear equation, Linear relationship, detection Limit, recovery, precision of method
A negative sample (wheat flour and wheat flour improver without stearoyl lactylate) was taken, a negative sample matrix solution was prepared according to example 1, and a stearoyl lactylate standard stock solution was taken to prepare matrix-matched standard solutions having concentrations of 0.5mg/kg, 2.5mg/kg, 5.0mg/kg and 10.0mg/kg, respectively, from the negative sample matrix solution. The detection of the concentration is carried out by high performance liquid chromatography tandem mass spectrometry from low to high in sequence, a linear regression curve is drawn by taking a chromatographic response value (y) of the SSL as a vertical coordinate and taking the corresponding concentration as (x), a linear regression equation of the SSL calculates a detection limit (MDL) and a quantification limit (MLOQ) according to signal-to-noise ratio (S/N) of 3 and 10 respectively, and a correlation coefficient, a linear range, the detection limit and the quantification lower limit are shown in a table 1.
TABLE 1 Linear Range, Linear equation, Linear relationship, detection limits and method quantitative lower limits
Negative wheat flour and wheat flour improver were selected and subjected to a labeling recovery test of 3 levels (1 × MLOQ, 2 × MLOQ and 10 × MLOQ) according to the method, each level was measured in parallel 6 times, and the Recovery and Standard Deviation (RSD) are shown in table 2.
TABLE 2 recovery and precision
Example 7
Preparation of monostearyl lactate standard solution
Stearoyl lactylate standard stock solutions: accurately weighing a proper amount of sodium stearoyl lactylate standard product in a 100mL volumetric flask by using a stearoyl lactate anion concentration meter, and metering the volume to a scale by using water to prepare a standard stock solution with the concentration of 500 mg/L.
Secondly, preparation of test solution
Weighing 1.0g of sample into a 15mL plastic centrifuge tube with a plug, adding 5.0mL of acetonitrile extracting solution, carrying out vortex oscillation for 2min, carrying out ultrasonic extraction for 10min, standing, and centrifuging 1mL of supernatant at 15000r/min for 5 min. The supernatant was aspirated and assayed.
Third, conditions of the apparatus
Chromatographic conditions
3.1 chromatographic column: HILIC chromatographic column (50 mm. times.4.6 mm. times.2.6 μm)
3.2 the column temperature is 40 ℃;
3.2 sample introduction: 1.0 μ L;
3.4 flow rate: 0.2 mL/min;
3.5 mobile phase: a is 0.1% ammonia water, B is acetonitrile; mobile phase ratio a: b is 5: 95.
conditions of Mass Spectrometry
3.6 ion source: electrospray ion, negative ion (ESI-) mode;
3.7 capillary voltage 4.0 KV;
3.8 the temperature of the ion source is 500 ℃,
3.9 atomizing gas: 20 psi; auxiliary gas: 5 psi; air curtain air: 20 psi;
3.10 scanning mode: multiple Reaction Monitoring (MRM) mode, monitoring ion pair m/z 355.4 > 283; m/z 355.4 > 89, quantitative ion pair m/z 355.4 > 283
Fourthly, drawing a standard curve
And accurately transferring the stearoyl lactylate standard stock solution, diluting with acetonitrile, and preparing into series of standard working solutions with the concentrations of 0.5mg/L, 1mg/L, 2mg/L and 5 mg/L. And (3) sequentially detecting the concentration from low to high by using a high performance liquid chromatography-tandem mass spectrometer, and drawing a standard curve by using the chromatographic peak area of the stearoyl lactylate as a horizontal coordinate and the concentration of the stearoyl lactylate as a vertical coordinate.
Fifth, measure
Precisely absorbing 1 mu L of the test solution, injecting the test solution into a high performance liquid chromatography-tandem mass spectrometer, measuring according to the high performance liquid chromatography-tandem mass spectrometry to obtain a high performance liquid chromatography-tandem mass spectrogram, checking the content of stearoyl lactylate in the measured solution from a standard curve, and calculating the content of the stearoyl lactylate in the test solution according to the sample mass represented by each 1mL of the test solution.
The technical features of the above embodiments can be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the above embodiments are not described, however, as long as there is no contradiction between the combinations of the technical features, the scope of the present description should be considered as being described in the present specification.
The above-mentioned embodiments only express several 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 inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (9)
1. A method for detecting stearoyl lactylate in flour or a flour improver is characterized by comprising the following steps:
pretreatment: adding an organic solvent into a flour or flour improver sample to be detected, extracting, and taking the supernatant to obtain a test sample solution;
and (3) detection: detecting the test solution by adopting a high performance liquid chromatography tandem mass spectrometer;
in the detection, chromatographic conditions comprise:
the chromatographic column is HILIC chromatographic column;
the mobile phase is formed by mixing the mobile phase A and the mobile phase B according to the volume ratio of (3:97) - (10:90), and the flow rate is 0.1-0.5 mL/min;
the mobile phase A is ammonia water, and the mobile phase B is acetonitrile.
2. The method for detecting stearoyl lactylate according to claim 1, wherein said chromatographic column has a column temperature of between 30 ℃ and 50 ℃.
3. The method for detecting stearoyl lactylate according to claim 1, wherein said mobile phase A is ammonia water with a volume percentage comprised between 0.05% and 0.15%.
4. The method for detecting stearoyl lactylate according to claim 3, wherein said mobile phase A is ammonia water with a volume percentage of 0.1 ± 0.01%.
5. The method for detecting stearoyl lactylate according to claim 1, wherein mobile phase A is mixed with mobile phase B in a volume ratio (4:96) - (6:94) and the flow rate of the mobile phase is comprised between 0.1 and 0.3 mL/min.
6. Method for the detection of stearoyl lactylate according to any of claims 1 to 5, wherein said detection mass spectrometric conditions comprise:
an ion source: electrospray ion, negative ion mode;
ion source temperature: 450 ℃ and 550 ℃;
atomizing: 18-22 psi; auxiliary gas: 3-7 psi; air curtain air: 18-22 psi;
the scanning mode is as follows: multiple reaction monitoring mode.
7. Method for the detection of stearoyl lactylate according to claim 6, wherein in said multiple reaction monitoring mode,
the monitored ion pairs were: m/z 355.4 is more than 283, m/z 355.4 is more than 89; the quantitative ion pair is: m/z 355.4 is more than 283.
8. The method for detecting stearoyl lactylate according to any of claims 1 to 5, wherein said organic solvent is acetonitrile in the pre-treatment of the sample.
9. The method for detecting stearoyl lactylate according to any of claims 1 to 5, further comprising:
preparing standard substance solutions with a series of concentrations, and detecting the standard substance solutions with the series of concentrations by adopting a high performance liquid chromatography tandem mass spectrometer;
and drawing a standard curve, and calculating the concentration of the stearoyl lactylate in the sample to be detected according to the standard curve.
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