CN112014497A - Method for simultaneously detecting three monoglyceride emulsifiers in dairy product based on gas chromatography-mass spectrometry - Google Patents
Method for simultaneously detecting three monoglyceride emulsifiers in dairy product based on gas chromatography-mass spectrometry Download PDFInfo
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- 235000013365 dairy product Nutrition 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 23
- 239000003995 emulsifying agent Substances 0.000 title claims abstract description 22
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 title claims abstract description 21
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 title claims abstract description 16
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims abstract description 32
- QHZLMUACJMDIAE-UHFFFAOYSA-N 1-monopalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)CO QHZLMUACJMDIAE-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 claims abstract description 16
- RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 claims abstract description 16
- 229940075507 glyceryl monostearate Drugs 0.000 claims abstract description 16
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 claims abstract description 16
- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000001514 detection method Methods 0.000 claims abstract description 11
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 19
- XCOBLONWWXQEBS-KPKJPENVSA-N N,O-bis(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)O\C(C(F)(F)F)=N\[Si](C)(C)C XCOBLONWWXQEBS-KPKJPENVSA-N 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 8
- 238000004458 analytical method Methods 0.000 claims description 7
- 239000011159 matrix material Substances 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 238000001819 mass spectrum Methods 0.000 claims description 6
- 235000013336 milk Nutrition 0.000 claims description 6
- 239000008267 milk Substances 0.000 claims description 6
- 210000004080 milk Anatomy 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000005051 trimethylchlorosilane Substances 0.000 claims description 6
- KIVJFBKIPFOIIR-UHFFFAOYSA-N FC(C(=O)N)(F)F.C[Si](C)C Chemical compound FC(C(=O)N)(F)F.C[Si](C)C KIVJFBKIPFOIIR-UHFFFAOYSA-N 0.000 claims description 5
- 238000004587 chromatography analysis Methods 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 238000012417 linear regression Methods 0.000 claims description 5
- 238000012545 processing Methods 0.000 claims description 5
- 238000005303 weighing Methods 0.000 claims description 5
- QHZLMUACJMDIAE-SFHVURJKSA-N 1-hexadecanoyl-sn-glycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)CO QHZLMUACJMDIAE-SFHVURJKSA-N 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- 238000006884 silylation reaction Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 3
- 239000012491 analyte Substances 0.000 claims description 3
- 239000012159 carrier gas Substances 0.000 claims description 3
- 238000001212 derivatisation Methods 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 239000001307 helium Substances 0.000 claims description 3
- 229910052734 helium Inorganic materials 0.000 claims description 3
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000002203 pretreatment Methods 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 238000011002 quantification Methods 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 3
- 230000000630 rising effect Effects 0.000 claims description 3
- 239000012224 working solution Substances 0.000 claims description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012086 standard solution Substances 0.000 claims description 2
- 238000007865 diluting Methods 0.000 claims 1
- 238000005516 engineering process Methods 0.000 abstract description 2
- 238000000622 liquid--liquid extraction Methods 0.000 abstract 1
- 238000000638 solvent extraction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000002444 silanisation Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 235000012970 cakes Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 235000003084 food emulsifier Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 235000013618 yogurt Nutrition 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
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N2030/042—Standards
- G01N2030/047—Standards external
Abstract
The invention discloses a method for simultaneously detecting three monoglyceride emulsifiers in a dairy product based on a gas chromatography-mass spectrometry method, which comprises the following steps: gas chromatography-mass spectrometry conditions; detecting monopalmitin, glyceryl monooleate and glyceryl monostearate; pretreating a sample; and (4) detecting the sample. The invention provides a novel method for analyzing three monoglyceride emulsifiers in a dairy product by adopting a simple liquid-liquid extraction method and combining a GC-MS analysis technology, the detection limit of an instrument is within the range of 0.26-1.20 mg/L, and a novel technical means is provided for the quality supervision of the dairy product.
Description
Technical Field
The invention belongs to the technical field of analysis, and particularly relates to a method for simultaneously detecting three monoglyceride emulsifiers in a dairy product based on a gas chromatography-mass spectrometry method.
Background
The food emulsifier belongs to a surfactant and can make oil and water mutually soluble. The method is widely applied to the processing process of foods such as dairy products, bread, cakes, biscuits, margarine, ice cream, beverages, chocolate and the like.
Dairy products are one of the foods with higher nutritional content in human dietary structure, and a certain amount of emulsifier is often added in the processing process of the dairy products to stabilize the quality of the dairy products. At present, the research on the emulsifier in the dairy product at home and abroad mainly focuses on the aspects of the emulsifying property of the emulsifier, the influence of the proportion of the compound emulsifier on the quality of the dairy product and the like. Relatively few research reports on detection of the content of the emulsifier in the dairy product mainly include gas chromatography and liquid chromatography. The analysis methods have the defects of complex sample pretreatment process, low detection sensitivity and the like. Because the amount of the emulsifier added in the process of processing the dairy product has an influence on the stability and safety of the quality of the dairy product, a new technology for quickly, conveniently and sensitively analyzing the emulsifier in the dairy product is needed to be established.
Disclosure of Invention
The invention aims to provide a rapid, simple and sensitive gas chromatography-mass spectrometry method for simultaneously detecting three monoglyceride emulsifiers (monopalmitin, glyceryl monooleate and glyceryl monostearate) in a dairy product.
The technical scheme of the invention is as follows: an analysis method for simultaneously determining three monoglyceride emulsifiers (monopalmitin, glyceryl monooleate and glyceryl monostearate) in a dairy product based on a gas chromatography-mass spectrometry method. Three monoglyceride emulsifiers (monopalmitin, glyceryl monooleate and glyceryl monostearate) in dairy products were used with CH2Cl2Extraction, derivatization with silanizing agent (BSTFA +1% TMCS), and gas chromatography-mass spectrometry.
The invention mainly comprises the following steps: gas chromatography-mass spectrometry conditions; detecting monopalmitin, glyceryl monooleate and glyceryl monostearate; pretreating a sample; and (4) detecting the sample.
An analysis method for simultaneously detecting three monoglyceride emulsifiers (monopalmitin, glyceryl monooleate and glyceryl monostearate) in a dairy product based on a gas chromatography-mass spectrometry method mainly comprises the following steps:
(1) gas chromatography-mass spectrometry conditions
The instrument used in the present invention is a gas chromatography-mass spectrometer (Agilent, usa) comprising a 7080B chromatography system, 5977MSD and NIST profile search library, chromatography conditions: a chromatographic column: HP-5MS capillary column; temperature rising procedure: the initial temperature is 60 ℃, the temperature is increased to 270 ℃ at 30 ℃/min, and the temperature is increased to 285 ℃ at 3 ℃/min; carrier gas: high purity helium gas; flow rate: 1.0 mL/min; sample introduction amount: 1.0 μ L; the split ratio is as follows: 10: 1; sample inlet temperature: at 250 ℃ to obtain a mixture. Mass spectrum conditions: an Electron Impact (EI) ion source; electron energy: 70 eV; ion source temperature: 230 ℃; temperature of the quadrupole rods: 150 ℃; solvent retardation: 6.5 min; the collection mode is as follows: an ion scanning mode is selected.
(2) Detection of glyceryl monopalmitate, glyceryl monooleate and glyceryl monostearate
In order to eliminate the influence of the sample matrix on the analysis result, the invention adopts a matrix standard curve for quantification. With CH of dairy product samples2Cl2Preparing a series of mixed matrix standard working solutions of monopalmitin, glyceryl monooleate and glyceryl monostearate with mass concentration by taking an extracting solution as a solvent, derivatizing by using a silanization reagent N, O-bis (trimethyl silicon) trifluoroacetamide (containing trimethyl chlorosilane) (BSTFA +1% TMCS), analyzing under the condition of the chromatography-mass spectrum, and performing linear regression on the concentration (x) of an analyte by using a peak area (y) to obtain a linear regression equation. Good linear relation (R) between 1-20 mg/L of monopalmitin, 5-100 mg/L of glyceryl monooleate and 10-200 mg/L of glyceryl monostearate2>0.992). The limit of detection (LOD) and limit of quantitation (LOQ) of the three target analytes are in the range of 0.26-1.20 mg/L and 0.87-4.01 mg/L, respectively.
(3) Pretreatment of samples
Accurately weighing about 0.5 g of milk sample, adding 5.0 mL of water and uniformly mixing; 10.0 mL of CH was added2Cl2Extracting, and shaking for 10 min. 13000 r/min for 10min, and collecting the lower organic phase. 10.0 mL of CH was added2Cl2Repeating the above processTaking the step, and combining organic phases. Taking 1.0 mL of extract liquid, drying with nitrogen, adding 50 mu L of pyridine for dissolution; then 100 mul of silylation reagent N, O-bis (trimethyl silicon) trifluoroacetamide (containing trimethyl chlorosilane) (BSTFA +1% TMCS) is added to react for 40 min at 70 ℃, and N-heptane is used for fixing the volume to 1.0 mL, thus obtaining the upper machine solution.
(4) Detection of samples
Accurately weighing about 0.5 g of milk sample, respectively adding three monoglyceride emulsifier mixed standard solutions with different concentration levels, processing the sample according to the sample pretreatment method, performing GC-MS analysis, and calculating the sample standard recovery rate.
The invention has the beneficial effects that: the invention designs a gas chromatography-mass spectrometry method for simultaneously detecting three monoglyceride emulsifiers of a dairy product, which can simply, conveniently, quickly and sensitively detect the three monoglyceride emulsifiers in the dairy product, provides convenience for future production and supervision, and can meet the domestic requirements on production and supervision.
Drawings
FIG. 1 is a chromatographic separation diagram of glyceryl monopalmitate, glyceryl monooleate and glyceryl monostearate.
(1. glyceryl monopalmitate (100 mg/L); 2. glyceryl monooleate (100 mg/L); 3. glyceryl monostearate (100 mg/L)).
Detailed Description
Example 1:
gas chromatography-mass spectrometry (Agilent, USA) including 7080B chromatography system, 5977MSD and NIST atlas database. Chromatographic conditions are as follows: a chromatographic column: HP-5MS capillary column; temperature rising procedure: the initial temperature is 60 ℃, the temperature is increased to 270 ℃ at 30 ℃/min, and the temperature is increased to 285 ℃ at 3 ℃/min; carrier gas: high purity helium gas; flow rate: 1.0 mL/min; sample introduction amount: 1.0 μ L; the split ratio is as follows: 10: 1; sample inlet temperature: at 250 ℃ to obtain a mixture. Mass spectrum conditions: an Electron Impact (EI) ion source; electron energy: 70 eV; ion source temperature: 230 ℃; temperature of the quadrupole rods: 150 ℃; solvent retardation: 6.5 min; the collection mode is as follows: an ion scan is selected. The mass spectrometric detection parameters for the three target compounds are shown in table 1.
Example 2:
with CH of dairy products2Cl2The extraction solution is used as a solvent, a series of mixed matrix standard working solutions of monopalmitin, glyceryl monooleate and glyceryl monostearate with mass concentration are prepared, after derivatization is carried out by a silanization reagent N, O-bis (trimethyl silicon) trifluoroacetamide (containing trimethyl chlorosilane) (BSTFA +1% TMCS), analysis is carried out under the conditions of the chromatogram and the mass spectrum, the linear regression is carried out on the concentration (x) of the analyte by using the peak area (y), and the linear equation, the detection limit and the quantitative limit are shown in a table 2.
Example 3:
pretreatment of a sample: accurately weighing about 0.5 g of milk sample, adding 5.0 mL of water and uniformly mixing; 10.0 mL of CH was added2Cl2Extracting, and shaking for 10 min. 13000 r/min for 10min, and collecting the lower organic phase. 10.0 mL of CH was added2Cl2The above extraction steps were repeated and the organic phases were combined. Taking 1.0 mL of extract liquid, drying with nitrogen, adding 50 mu L of pyridine for dissolution; then 100 mul of silylation reagent N, O-bis (trimethyl silicon) trifluoroacetamide (containing trimethyl chlorosilane) (BSTFA +1% TMCS) is added to react for 40 min at 70 ℃, and the volume is determined to 1.0 mL by using N-heptane, thus obtaining the upper machine solution.
Example 4:
about 0.5 g of yoghourt and pure milk samples are accurately weighed, three mixed standard monoglyceride solutions with different concentration levels are respectively added, the samples are processed according to the sample pretreatment method, GC-MS analysis is carried out, the sample standard addition recovery rate and the precision are calculated, and the results are shown in Table 3.
The foregoing is a more detailed description of the invention in connection with specific preferred embodiments and it is not intended that the invention be limited to these specific details. It should be understood by those skilled in the art that various changes and substitutions may be made in accordance with the technical solution and the inventive concept of the present invention, and the same properties or uses should be considered as the protection scope of the present invention.
Claims (2)
1. A method for simultaneously detecting three monoglyceride emulsifiers in a dairy product based on a gas chromatography-mass spectrometry method is characterized by comprising the following steps: mainly comprises the following steps:
(1) gas chromatography-mass spectrometry conditions;
(2) detecting monopalmitin, glyceryl monooleate and glyceryl monostearate;
(3) pretreating a sample;
(4) and (4) detecting the sample.
2. The method for simultaneously detecting three monoglyceride emulsifiers in a dairy product based on gas chromatography-mass spectrometry according to claim 1, wherein: mainly comprises the following steps:
(1) gas chromatography-mass spectrometry conditions
The instrument used in the present invention is a gas chromatography-mass spectrometer (Agilent, usa) comprising a 7080B chromatography system, 5977MSD and NIST profile search library, chromatography conditions: a chromatographic column: HP-5MS capillary column; temperature rising procedure: the initial temperature is 60 ℃, the temperature is increased to 270 ℃ at 30 ℃/min, and the temperature is increased to 285 ℃ at 3 ℃/min; carrier gas: high purity helium gas; flow rate: 1.0 mL/min; sample introduction amount: 1.0 μ L; the split ratio is as follows: 10: 1; sample inlet temperature: 250 ℃; mass spectrum conditions: an Electron Impact (EI) ion source; electron energy: 70 eV; ion source temperature: 230 ℃; temperature of the quadrupole rods: 150 ℃; solvent retardation: 6.5 min; the collection mode is as follows: selecting an ion scanning mode;
(2) detection of glyceryl monopalmitate, glyceryl monooleate and glyceryl monostearate
In order to eliminate the influence of the sample matrix on the analysis result, the invention adopts a matrix standard curveCarrying out quantification; with CH of dairy product samples2Cl2Preparing a series of mixed matrix standard working solutions of monopalmitin, glyceryl monooleate and glyceryl monostearate with mass concentration by taking an extracting solution as a solvent, performing derivatization by using a silylation reagent N, O-bis (trimethyl silicon) trifluoroacetamide (containing trimethyl chlorosilane) (BSTFA +1% TMCS), analyzing under the condition of the chromatography-mass spectrum, and performing linear regression on the concentration (x) of an analyte by using a peak area (y) to obtain a linear regression equation; good linear relation (R) between 1-20 mg/L of monopalmitin, 5-100 mg/L of glyceryl monooleate and 10-200 mg/L of glyceryl monostearate2>0.992); the detection Limit (LOD) and the quantification Limit (LOQ) of the three target analytes are respectively in the range of 0.26-1.20 mg/L and 0.87-4.01 mg/L;
(3) pretreatment of samples
Accurately weighing about 0.5 g of milk sample, adding 5.0 mL of water and uniformly mixing; 10.0 mL of CH was added2Cl2Extracting, and oscillating for 10 min; 13000 r/min for 10min, collecting the lower organic phase, adding 10.0 mL CH2Cl2Repeating the extraction steps, and combining organic phases; taking 1.0 mL of extract liquid, drying with nitrogen, adding 50 mu L of pyridine for dissolution; adding 100 μ L silylation reagent N, O-bis (trimethylsilyl) trifluoroacetamide (containing trimethylchlorosilane) (BSTFA +1% TMCS), reacting at 70 deg.C for 40 min, and diluting to 1.0 mL with N-heptane to obtain upper machine solution;
(4) detection of samples
Accurately weighing about 0.5 g of milk sample, respectively adding three monoglyceride emulsifier mixed standard solutions with different concentration levels, processing the sample according to the sample pretreatment method, performing GC-MS analysis, and calculating the sample standard recovery rate.
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| CN113325064A (en) * | 2021-05-28 | 2021-08-31 | 华南农业大学 | Method for identifying charm peak emulsifier components by atmospheric pressure chemical ionization mass spectrometry |
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| CN113325064A (en) * | 2021-05-28 | 2021-08-31 | 华南农业大学 | Method for identifying charm peak emulsifier components by atmospheric pressure chemical ionization mass spectrometry |
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Application publication date: 20201201 |