CN112034072B - Method for measuring content and condensation degree of citral diethyl acetal and laural diethyl acetal in perfume by gas chromatography-tandem mass spectrometry - Google Patents
Method for measuring content and condensation degree of citral diethyl acetal and laural diethyl acetal in perfume by gas chromatography-tandem mass spectrometry Download PDFInfo
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Abstract
A method for determining the content and the condensation degree of citral diethyl acetal and laural diethyl acetal in a spice by gas chromatography-tandem mass spectrometry, which is based on the gas chromatography-tandem mass spectrometry and comprises the following two steps of analysis processes aiming at spice samples for foods: (1) Weighing 1g of edible spice sample into a centrifuge tube, adding 10 mu L of deuterated acetophenone internal standard solution, adding 1g of sodium chloride, adding 2mL of water, shaking uniformly, adding 2mL of dichloromethane, performing vortex extraction and centrifugation, taking 1mL of dichloromethane phase, and performing analysis by gas chromatography-tandem mass spectrometry; (2) Weighing 5g edible spice sample in round bottom flask, adding 25mL of 5% diluted sulfuric acid, refluxing in 100 deg.C oil bath for 3 hr, cooling to room temperature, adding NaOH solution to adjust pH to neutrality, adding NaH 2 PO 4 And H 3 PO 4 1g of sample is weighed into a centrifuge tube, 10 mu L of deuterated acetophenone internal standard solution is added, 1g of sodium chloride is added, 2mL of water is added, shaking is carried out, 2mL of dichloromethane is added, vortex extraction is carried out for 5min, centrifugation is carried out, 1mL of dichloromethane phase is taken, and analysis is carried out by gas chromatography-tandem mass spectrometry. Preparing a series of standard solutions of citral and laural, adopting gas chromatography-tandem mass spectrometry, obtaining quantitative marked lines of citral and laural based on ion pair information of citral, laural and deuterated acetophenone, completing quantitative analysis of citral and laural in the sample, and calculating to obtain the content and condensation degree of citral diethyl acetal and laural diethyl acetal in the sample.
Description
Technical Field
The invention belongs to the technical field of analysis and detection of food flavors, and particularly relates to a method for measuring the content and condensation degree of citral diethyl acetal and laural diethyl acetal in a flavor by gas chromatography-tandem mass spectrometry.
Background
In the food flavor chemistry, aldehyde substances (furfural, benzaldehyde, laural, citral, citronellal) and ketone substances (acetophenone, 2, 3-butanedione) can be used as the flavor. However, the carbonyl functional group, particularly the aldehyde substance, is relatively active in chemical properties, and is liable to undergo oxidation, addition, condensation and other reactions, and is used as a perfume, and is liable to undergo deterioration in alkaline environment to lose fragrance. When carbonyl compounds are condensed with alcohols to generate acetals or ketals, the stability is greatly improved, the carbonyl compounds are stable in alkaline environment and are not easy to deteriorate, and the fragrance is more elegant and durable than before condensation. Thus, the development of acetal ketone fragrances for foods is rapid, and the yield and the number of new varieties are rapidly increased.
Citral diethyl acetal and laural diethyl acetal are produced by condensation reaction of citral, laural and ethylene glycol, and have fragrance of flos Rosae Rugosae, fructus hyacinth, bulbus Lilii, fructus Citri Limoniae, and mandarin orange, and are acetal substances commonly used as food flavoring. At present, no corresponding detection method is found for citral diethyl acetal and laural diethyl acetal in food flavors, and the content and the condensation degree of the citral diethyl acetal and laural diethyl acetal relate to the evaluation and the use of flavor quality. Therefore, it is of great importance to establish a method for measuring the content and the degree of condensation of citral diethyl acetal and laural diethyl acetal in food flavors.
Disclosure of Invention
The invention aims at the determination of citral diethyl acetal and laural diethyl acetal in food flavor, and provides a method for determining the content and condensation degree of citral diethyl acetal and laural diethyl acetal in the flavor by gas chromatography-tandem mass spectrometry.
Because the standard products of citral diethyl acetal and laural diethyl acetal substances are generally difficult to obtain, the direct qualitative and quantitative analysis of the citral diethyl acetal and the laural diethyl acetal substances is difficult.
The aim of the invention is achieved by the following scheme:
(1) Weighing 1g of edible spice sample into a centrifuge tube, adding 10 mu L of deuterated acetophenone internal standard solution, adding 1g of sodium chloride, adding 2mL of water, shaking uniformly, adding 2mL of dichloromethane, performing vortex extraction, centrifuging, and taking 1mL of dichloromethane phase to be analyzed;
(2) Weighing 5g edible spice sample in round bottom flask, adding 25mL of 5% diluted sulfuric acid, refluxing in 100 deg.C oil bath for 3 hr, cooling to room temperature, adding NaOH solution to adjust pH to neutrality, adding NaH 2 PO 4 And H 3 PO 4 1g of sample is weighed into a centrifuge tube, 10 mu L of deuterated acetophenone internal standard solution is added, 1g of sodium chloride is added, 2mL of water is added, shaking is carried out, 2mL of dichloromethane is added, vortex extraction is carried out for 5min, centrifugation is carried out, and 1mL of dichloromethane phase is taken for analysis;
(3) Preparing a series of standard solutions of citral and laural, adopting gas chromatography-tandem mass spectrometry, obtaining quantitative marked lines of citral and laural based on ion pair information of citral, laural and deuterated acetophenone, completing quantitative analysis of citral and laural in a sample, and calculating to obtain the content and condensation degree of citral diethyl acetal and laural diethyl acetal.
In the invention, the internal standard solution of deuterated acetophenone is acetonitrile solution with the concentration of 1mg/mL; naOH solutionThe concentration of the liquid is 8mol/L; naH in buffer salt 2 PO 4 And H 3 PO 4 The mass ratio is 2:1.
In the invention, the gas chromatography-tandem mass spectrometry analysis conditions are specifically as follows: chromatographic sample inlet temperature: 280 ℃; sample injection amount: 1 μl; sample injection mode: sample introduction without diversion; carrier gas: helium with constant flow rate of 1.5mL/min; chromatographic column: DB-5MS, specification 30m x 0.32mm x 0.25 μm; programming temperature: the initial temperature is 60 ℃, the temperature is kept for 1min, and the temperature is increased to 230 ℃ at 10 ℃/min; raising the temperature to 280 ℃ at 5 ℃/min, and keeping the temperature for 20min; transmission line temperature: 290 ℃; mass spectrometry ionization mode: EI; ion source temperature: 250 ℃; mass spectrometry scanning mode: multi-reaction monitoring MRM mode; collision gas: ar gas, air pressure 1.5mTorr.
In the method, the vortex extraction time is 5min, and the centrifugation time is 3min.
In the method, standard solutions of citral and lauraldehyde contain deuterated acetophenone as an internal standard.
In the method, the condensation degree of the citral diethyl acetal and the laural diethyl acetal content is calculated by subtracting the original sample content from the citral and laural content after acidic hydrolysis, the increase of the citral diethyl acetal and the laural diethyl acetal content is calculated to determine the citral diethyl acetal and the laural diethyl acetal content, and the condensation degree is calculated based on the original citral and laural content.
Mass spectrum parameter optimization is carried out on citral, laural and deuterated acetophenone by using the method, and related parameters such as parent ion, child ion and Collision Energy (CE) values of the compounds are shown in table 1:
mass spectrometric parameters for each compound of table 1
The method has the following excellent effects:
the method adopts a two-step method to finish the measurement of the content and the condensation degree of the citral diethyl acetal and the laural diethyl acetal, namely, the original sample and the sample after acidic hydrolysis are respectively analyzed to obtain the content of the citral and the laural, and the content and the condensation degree of the citral diethyl acetal and the laural diethyl acetal are calculated by a subtraction method, so that the method overcomes the difficulty of directly testing the citral diethyl acetal and the laural diethyl acetal, and can be applied to the measurement of the citral diethyl acetal and the laural diethyl acetal in food flavors.
Drawings
FIG. 1 shows chromatograms of citral and laural in the present invention.
Detailed Description
The invention will be further illustrated with reference to the following examples:
(1) Weighing 1g of edible spice sample into a centrifuge tube, adding 10 mu L of deuterated acetophenone internal standard acetonitrile solution (1 mg/mL), adding 1g of sodium chloride, adding 2mL of water, shaking uniformly, adding 2mL of dichloromethane, performing vortex extraction for 5min, centrifuging for 3min, and taking 1mL of dichloromethane phase to be analyzed;
(2) Weighing 5g edible spice sample in round bottom flask, adding 25mL of 5% diluted sulfuric acid, refluxing in 100 deg.C oil bath for 3 hr, cooling to room temperature, adding 8mol/L NaOH solution to adjust pH to neutrality, adding 5g of NaH 2 PO 4 And H 3 PO 4 1g of sample is weighed into a centrifuge tube, 10 mu L of deuterated acetophenone internal standard acetonitrile solution with the concentration of 1mg/mL is added, 1g of sodium chloride is added, 2mL of water is added, shaking is carried out uniformly, 2mL of dichloromethane is added, vortex extraction is carried out for 5min, centrifugation is carried out for 3min, and 1mL of dichloromethane phase is taken for analysis;
(3) The gas chromatography-tandem mass spectrometry conditions were specifically set as follows: chromatographic sample inlet temperature: 280 ℃; sample injection amount: 1 μl; sample injection mode: sample introduction without diversion; carrier gas: helium with constant flow rate of 1.5mL/min; chromatographic column: DB-5MS, specification 30m x 0.32mm x 0.25 μm; programming temperature: the initial temperature is 60 ℃, the temperature is kept for 1min, and the temperature is increased to 230 ℃ at 10 ℃/min; raising the temperature to 280 ℃ at 5 ℃/min, and keeping the temperature for 20min; transmission line temperature: 290 ℃; mass spectrometry ionization mode: EI; ion source temperature: 250 ℃; mass spectrometry scanning mode: multi-reaction monitoring MRM mode; collision gas: ar gas, air pressure 1.5mTorr. Ion pair information is as follows:
(4) A series of standard solutions of citral and laural were prepared at concentrations of 10. Mu.g/g, 20. Mu.g/g, 50. Mu.g/g, 100. Mu.g/g, 200. Mu.g/g, 500. Mu.g/g, respectively.
(5) And (3) obtaining quantitative marked lines of citral and laural based on ion pair information of citral, laural and deuterated acetophenone by adopting gas chromatography-tandem mass spectrometry, completing quantitative analysis of citral and laural in a sample, and calculating to obtain the content and condensation degree of citral diethyl acetal and laural diethyl acetal.
The method is used for measuring the content and the condensation degree of citral diethyl acetal and laural diethyl acetal in a food spice, and the result is that the content of citral diethyl acetal is 54.6 mug/g, the condensation degree is 76.3%, the content of laural diethyl acetal is 35.1 mug/g, and the condensation degree is 63.4%.
Claims (5)
1. A method for measuring the content and condensation degree of citral diethyl acetal and laural diethyl acetal in perfume by gas chromatography-tandem mass spectrometry is characterized in that: the method is based on gas chromatography-tandem mass spectrometry, and aims at a food flavor sample, firstly, the citral and the lauraldehyde in the sample are qualitatively and quantitatively analyzed, then, the citral diethyl acetal and the lauraldehyde diethyl acetal in the sample are subjected to acid hydrolysis reaction, and then, the citral and the lauraldehyde are analyzed to obtain the content and the condensation degree of the citral diethyl acetal and the lauraldehyde diethyl acetal in the food flavor, and the method specifically comprises the following steps:
(1) Weighing 1g of edible spice sample into a centrifuge tube, adding 10 mu L of deuterated acetophenone internal standard solution, adding 1g of sodium chloride, adding 2mL of water, shaking uniformly, adding 2mL of dichloromethane, performing vortex extraction, centrifuging, and taking 1mL of dichloromethane phase to be analyzed;
(2) Weighing 5g edible spice sample in round bottom flask, adding 25mL of 5% diluted sulfuric acid, refluxing in 100 deg.C oil bath for 3 hr, cooling to room temperature, adding NaOH solution to adjust pH to neutrality, adding NaH 2 PO 4 And H 3 PO 4 Slow of compositionPouring salt, weighing 1g of sample into a centrifuge tube, adding 10 mu L of deuterated acetophenone internal standard solution, adding 1g of sodium chloride, adding 2mL of water, shaking uniformly, adding 2mL of dichloromethane, performing vortex extraction for 5min, centrifuging, and taking 1mL of dichloromethane phase to be analyzed;
(3) Preparing a series of standard solutions of citral and laural, obtaining quantitative marked lines of the citral and the laural based on ion pair information of the citral, the laural and deuterated acetophenone by adopting gas chromatography-tandem mass spectrometry, completing quantitative analysis of the citral and the laural in a sample, and calculating to obtain the content and the condensation degree of the citral diethyl acetal and the laural diethyl acetal;
wherein the concentration of the NaOH solution is 8mol/L, and NaH in the buffer salt 2 PO 4 And H 3 PO 4 The mass ratio is 2:1;
wherein the ion pair information of citral, laural, deuterated acetophenone is as follows:
2. the method according to claim 1, characterized in that: the internal standard solution of deuterated acetophenone in the method is acetonitrile solution with the concentration of 1mg/mL.
3. The method according to any one of claims 1-2, wherein: the gas chromatography-tandem mass spectrometry analysis conditions in the method are specifically as follows: chromatographic sample inlet temperature: 280 ℃; sample injection amount: 1 μl; sample injection mode: sample introduction without diversion; carrier gas: helium with constant flow rate of 1.5mL/min; chromatographic column: DB-5MS, specification 30m x 0.32mm x 0.25 μm; programming temperature: the initial temperature is 60 ℃, the temperature is kept for 1min, and the temperature is increased to 230 ℃ at 10 ℃/min; raising the temperature to 280 ℃ at 5 ℃/min, and keeping the temperature for 20min; transmission line temperature: 290 ℃; mass spectrometry ionization mode: EI; ion source temperature: 250 ℃; mass spectrometry scanning mode: multi-reaction monitoring MRM mode; collision gas: ar gas, air pressure 1.5mTorr.
4. The method according to claim 1, characterized in that: in the method, the vortex extraction time is 5min, and the centrifugation time is 3min.
5. The method according to claim 1, characterized in that: the standard solutions of citral and lauraldehyde in the method contain deuterated acetophenone as an internal standard.
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Inventor after: Ma Zhiwei Inventor after: Xu Jun Inventor after: Liu Zhijing Inventor after: Liu Juntao Inventor after: Wang Chuanchuan Inventor after: Ren Cong Inventor after: Ding Degang Inventor after: Hao Jinghao Inventor after: Yang Xinling Inventor after: Wang Jianling Inventor before: Liu Zhijing Inventor before: Xu Jun Inventor before: Ma Zhiwei Inventor before: Liu Juntao Inventor before: Wang Chuanchuan Inventor before: Ren Cong Inventor before: Ding Degang Inventor before: Hao Jinghao Inventor before: Yang Xinling Inventor before: Wang Jianling |
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