CN112034072A - Method for measuring content and condensation degree of citral diacetal and lauraldehyde diacetal in perfume through gas chromatography-tandem mass spectrometry - Google Patents
Method for measuring content and condensation degree of citral diacetal and lauraldehyde diacetal in perfume through gas chromatography-tandem mass spectrometry Download PDFInfo
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Abstract
The application relates to a method for measuring the content and condensation degree of citral diacetal and lauraldehyde diacetal in a spice by gas chromatography-tandem mass spectrometry, which comprises the following steps: (1) firstly, weighing a spice sample in a centrifugal tube, then adding an internal standard, sodium chloride, water and dichloromethane, extracting, centrifuging, taking a dichloromethane phase, and performing instrument analysis; (2) weighing a spice sample in a flask, adding a dilute sulfuric acid solution, refluxing in an oil bath, adding a NaOH solution to adjust the pH value to be neutral, adding buffer salt, weighing the solution in a centrifugal tube, adding an internal standard, sodium chloride, water and dichloromethane, extracting, centrifuging, taking a dichloromethane phase, and performing instrument analysis. Preparing a series of standard solutions of citral and lauraldehyde, carrying out sample injection analysis, obtaining quantitative marking lines of citral and lauraldehyde based on ion pair information, completing the quantitative analysis of citral and lauraldehyde in the sample, and calculating to obtain the content and condensation degree of citral diacetal and lauraldehyde diacetal in the sample.
Description
Technical Field
The invention belongs to the technical field of food spice analysis and detection, and particularly relates to a method for measuring the content and condensation degree of citral diacetal and lauraldehyde diacetal in spice by gas chromatography-tandem mass spectrometry.
Background
In food flavor chemistry, aldehydes (furfural, benzaldehyde, lauraldehyde, citral, citronellal) and ketones (acetophenone, 2, 3-butanedione) can be used as flavors. However, since carbonyl functional groups, particularly aldehydes, are chemically active, they are susceptible to oxidation, addition, condensation, and other reactions, and when used as fragrances, they are susceptible to deterioration in alkaline environments and loss of fragrance. When carbonyl compounds are condensed with alcohols to generate acetal or ketal substances, the stability of the carbonyl compounds is greatly improved, the carbonyl compounds are stable in alkaline environment and are not easy to deteriorate, and the fragrance of the carbonyl compounds is more elegant and lasting than that before condensation. Therefore, the development of acetal ketone flavor for food is rapid, and the yield and the number of new varieties are rapidly increased.
Citral diacetal and laurylaldehyde diacetal are produced by condensation reaction of citral, laurylaldehyde and ethylene glycol, have fragrance of flos Rosae Rugosae, hyacinth, Bulbus Lilii, fructus Citri Limoniae, and mandarin orange, and are acetals commonly used in food flavor. At present, no corresponding detection method is found for citral diacetal and lauraldehyde diacetal in the food flavor, and the content and the condensation degree of the citral diacetal and the lauraldehyde diacetal are related to the evaluation and the use of the flavor quality. Therefore, establishing a method for measuring the content and the condensation degree of the citral diacetal and the lauraldehyde diacetal in the food spice has important significance.
Disclosure of Invention
The invention aims at the requirement of measuring citral diethyl acetal and lauraldehyde diethyl acetal in a food flavor, and provides a method for measuring the content and the condensation degree of the citral diethyl acetal and the lauraldehyde diethyl acetal in the flavor by gas chromatography-tandem mass spectrometry.
According to the method for determining the content and the condensation degree of the citral diacetal and the laurel aldehyde diacetal in the food spice, firstly, the citral and the laurel aldehyde in a sample are qualitatively and quantitatively analyzed, then, the citral diacetal and the laurel aldehyde diacetal in the sample are subjected to acid hydrolysis reaction, and then, the citral and the laurel aldehyde are analyzed, so that the content and the condensation degree of the citral diacetal and the laurel aldehyde diacetal in the food spice are obtained.
The purpose of the invention is realized by the following scheme:
(1) weighing 1g of edible spice sample in a centrifugal tube, adding 10 mu L of deuterated acetophenone internal standard solution, adding 1g of sodium chloride, adding 2mL of water, shaking up, adding 2mL of dichloromethane, performing vortex extraction, centrifuging, and taking 1mL of dichloromethane phase to be analyzed;
(2) weighing 5g of edible spice sample in a round-bottom flask, adding 25mL of dilute sulfuric acid with the mass fraction of 5%, refluxing in oil bath at 100 ℃ for 3 hours, cooling to room temperature, adding NaOH solution to adjust the pH to be neutral, adding buffer salt consisting of NaH2PO4 and H3PO4, weighing 1g of sample in a centrifugal tube, adding 10 mu L of deuterated acetophenone internal standard solution, adding 1g of sodium chloride, adding 2mL of water, shaking up, 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 lauraldehyde, obtaining quantitative marking lines of the citral and the lauraldehyde based on ion pair information of the citral, the lauraldehyde and the deuterated acetophenone by adopting a gas chromatography-tandem mass spectrum, completing quantitative analysis of the citral and the lauraldehyde in a sample, and calculating the content and the condensation degree of the citral diethyl acetal and the lauraldehyde diethyl acetal.
In the invention, an internal standard solution of deuterated acetophenone is an acetonitrile solution with the concentration of 1 mg/mL; the concentration of the NaOH solution is 8 mol/L; the mass ratio of NaH2PO4 to H3PO4 in the buffer salt was 2: 1.
In the invention, the gas chromatography-tandem mass spectrometry analysis conditions are specifically as follows: temperature of a chromatographic sample inlet: 280 ℃; sample introduction amount: 1 mu L of the solution; and (3) sample introduction mode: no shunt sampling; carrier gas: helium, constant flow rate 1.5 mL/min; a chromatographic column: DB-5MS with the specification of 30m multiplied by 0.32mm multiplied by 0.25 mu m; temperature programming: the initial temperature is 60 ℃, the temperature is kept for 1min, and the temperature is increased to 230 ℃ at the speed of 10 ℃/min; raising the temperature to 280 ℃ at a speed of 5 ℃/min, and keeping the temperature for 20 min; transmission line temperature: 290 ℃; mass spectrum ionization mode: EI; ion source temperature: 250 ℃; mass spectrum scanning mode: multiple reaction monitoring, MRM, mode; collision gas: ar gas, pressure 1.5 mTorr.
In the method, the vortex extraction time is 5min, and the centrifugation time is 3 min.
In the invention, the standard solution of the citral and the lauraldehyde in the method contains deuterated acetophenone as an internal standard.
In the present invention, the degree of condensation of the citral diacetal and the laural diacetal content in the method is calculated by subtracting the content of the original sample from the citral, laural content after the acid hydrolysis to determine the citral diacetal and laural diacetal content, and calculating the degree of condensation based on the citral, laural content as it is.
The method is used for optimizing the mass spectrum parameters of citral, laurylaldehyde and deuterated acetophenone, and the values of relevant parameters such as parent ions and ionic ions of the compounds and the Collision Energy (CE) are shown in table 1:
table 1 mass spectrometric detection parameters for each compound
The method of the invention has the following excellent effects:
the method adopts a two-step method to complete the determination of the content and the condensation degree of the citral diacetal and the lauraldehyde diacetal, namely, the analysis of the original sample and the sample after the acid hydrolysis is respectively carried out to obtain the content of the citral and the lauraldehyde, and the content and the condensation degree of the citral diacetal and the lauraldehyde diacetal are calculated by a differential subtraction method, so that the difficulty of directly testing the citral diacetal and the lauraldehyde diacetal is overcome, and the method can be applied to the determination of the citral diacetal and the lauraldehyde diacetal in the food spice.
Drawings
FIG. 1 is a chromatogram of citral and laurylaldehyde according to the invention.
Detailed Description
The invention will be further illustrated with reference to the following examples:
(1) weighing 1g of edible spice sample in a centrifuge tube, adding 10 mu L of deuterated acetophenone internal standard acetonitrile solution (1mg/mL), adding 1g of sodium chloride, adding 2mL of water, shaking up, adding 2mL of dichloromethane, performing vortex extraction for 5min, centrifuging for 3min, and taking 1mL of dichloromethane phase to be analyzed;
(2) weighing 5g of edible spice sample in a round-bottom flask, adding 25mL of dilute sulfuric acid with the mass fraction of 5%, refluxing in an oil bath at 100 ℃ for 3 hours, cooling to room temperature, adding 8mol/L of NaOH solution to adjust the pH to be neutral, adding 5g of buffer salt consisting of NaH2PO4 and H3PO4, weighing 1g of sample in a centrifugal tube, adding 10 muL of deuterated acetophenone internal standard acetonitrile solution with the concentration of 1mg/mL, adding 1g of sodium chloride, adding 2mL of water, shaking up, adding 2mL of dichloromethane, performing vortex extraction for 5min, centrifuging for 3min, and taking 1mL of dichloromethane phase to be analyzed;
(3) the specific set gas chromatography-tandem mass spectrometry conditions are as follows: temperature of a chromatographic sample inlet: 280 ℃; sample introduction amount: 1 mu L of the solution; and (3) sample introduction mode: no shunt sampling; carrier gas: helium, constant flow rate 1.5 mL/min; a chromatographic column: DB-5MS with the specification of 30m multiplied by 0.32mm multiplied by 0.25 mu m; temperature programming: the initial temperature is 60 ℃, the temperature is kept for 1min, and the temperature is increased to 230 ℃ at the speed of 10 ℃/min; raising the temperature to 280 ℃ at a speed of 5 ℃/min, and keeping the temperature for 20 min; transmission line temperature: 290 ℃; mass spectrum ionization mode: EI; ion source temperature: 250 ℃; mass spectrum scanning mode: multiple reaction monitoring, MRM, mode; collision gas: ar gas, pressure 1.5 mTorr. The ion pair information is as follows:
(4) preparing a series of standard solutions of citral and lauraldehyde, wherein the concentrations are 10 μ g/g, 20 μ g/g, 50 μ g/g, 100 μ g/g, 200 μ g/g and 500 μ g/g respectively.
(5) And (3) obtaining quantitative marking lines of the citral and the lauraldehyde by adopting gas chromatography-tandem mass spectrometry based on ion pair information of the citral, the lauraldehyde and the deuterated acetophenone, completing quantitative analysis of the citral and the lauraldehyde in the sample, and calculating the content and the condensation degree of the citral diethyl acetal and the lauraldehyde diethyl acetal.
The content and degree of condensation of citral diacetal and lauraldehyde diacetal in a flavor for food were measured by the method of the present invention, and as a result, the citral diacetal content was 54.6. mu.g/g, the degree of condensation was 76.3%, the lauraldehyde diacetal content was 35.1. mu.g/g, and the degree of condensation was 63.4%.
Claims (6)
1. A method for measuring the content and condensation degree of citral diacetal and lauraldehyde diacetal in a spice by gas chromatography-tandem mass spectrometry is characterized in that: based on gas chromatography-tandem mass spectrometry, aiming at a food spice sample, firstly, qualitatively and quantitatively analyzing citral and lauraldehyde in the sample, then, carrying out acidic hydrolysis reaction on citral diethyl acetal and lauraldehyde diethyl acetal in the sample, and then, analyzing the citral and lauraldehyde to obtain the content and the condensation degree of the citral diethyl acetal and the lauraldehyde diethyl acetal in the edible spice, wherein the method specifically comprises the following steps:
(1) weighing 1g of edible spice sample in a centrifugal tube, adding 10 mu L of deuterated acetophenone internal standard solution, adding 1g of sodium chloride, adding 2mL of water, shaking up, adding 2mL of dichloromethane, performing vortex extraction, centrifuging, and taking 1mL of dichloromethane phase to be analyzed;
(2) weighing 5g of edible spice sample in a round-bottom flask, adding 25mL of dilute sulfuric acid with the mass fraction of 5%, refluxing in oil bath at 100 ℃ for 3 hours, cooling to room temperature, adding NaOH solution to adjust the pH to be neutral, adding buffer salt consisting of NaH2PO4 and H3PO4, weighing 1g of sample in a centrifugal tube, adding 10 mu L of deuterated acetophenone internal standard solution, adding 1g of sodium chloride, adding 2mL of water, shaking up, 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 lauraldehyde, obtaining quantitative marking lines of the citral and the lauraldehyde based on ion pair information of the citral, the lauraldehyde and the deuterated acetophenone by adopting a gas chromatography-tandem mass spectrum, completing quantitative analysis of the citral and the lauraldehyde in a sample, and calculating the content and the condensation degree of the citral diethyl acetal and the lauraldehyde diethyl acetal.
2. The method of claim 1, wherein: in the method, an internal standard solution of the deuterated acetophenone is an acetonitrile solution with the concentration of 1 mg/mL.
3. The method according to any one of claims 1-2, wherein: in the method, the concentration of NaOH solution is 8mol/L, and the mass ratio of NaH2PO4 to H3PO4 in buffer salt is 2: 1.
4. A method according to any one of claims 1-3, characterized in that: the gas chromatography-tandem mass spectrometry analysis conditions in the method are as follows: temperature of a chromatographic sample inlet: 280 ℃; sample introduction amount: 1 mu L of the solution; and (3) sample introduction mode: no shunt sampling; carrier gas: helium, constant flow rate 1.5 mL/min; a chromatographic column: DB-5MS with the specification of 30m multiplied by 0.32mm multiplied by 0.25 mu m; temperature programming: the initial temperature is 60 ℃, the temperature is kept for 1min, and the temperature is increased to 230 ℃ at the speed of 10 ℃/min; raising the temperature to 280 ℃ at a speed of 5 ℃/min, and keeping the temperature for 20 min; transmission line temperature: 290 ℃; mass spectrum ionization mode: EI; ion source temperature: 250 ℃; mass spectrum scanning mode: multiple reaction monitoring, MRM, mode; collision gas: ar gas, pressure 1.5 mTorr.
5. The method of claim 1, wherein: in the method, the vortex extraction time is 5min, and the centrifugation time is 3 min.
6. The method of claim 1, wherein: the standard solutions of citral and laurylaldehyde in the process contain deuterated acetophenone as internal standard.
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| CN114199986A (en) * | 2021-12-10 | 2022-03-18 | 河南牧业经济学院 | Method for simultaneously determining 3 aldehyde compounds in beer |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114199986A (en) * | 2021-12-10 | 2022-03-18 | 河南牧业经济学院 | Method for simultaneously determining 3 aldehyde compounds in beer |
| CN114199986B (en) * | 2021-12-10 | 2024-05-07 | 河南牧业经济学院 | Method for simultaneously measuring 3 aldehyde compounds in beer |
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