CN117607284A - Method for detecting cannabinol substances in edible oil - Google Patents
Method for detecting cannabinol substances in edible oil Download PDFInfo
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- CN117607284A CN117607284A CN202311428442.1A CN202311428442A CN117607284A CN 117607284 A CN117607284 A CN 117607284A CN 202311428442 A CN202311428442 A CN 202311428442A CN 117607284 A CN117607284 A CN 117607284A
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- ZTGXAWYVTLUPDT-UHFFFAOYSA-N cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CC=C(C)C1 ZTGXAWYVTLUPDT-UHFFFAOYSA-N 0.000 title claims abstract description 90
- VBGLYOIFKLUMQG-UHFFFAOYSA-N Cannabinol Chemical compound C1=C(C)C=C2C3=C(O)C=C(CCCCC)C=C3OC(C)(C)C2=C1 VBGLYOIFKLUMQG-UHFFFAOYSA-N 0.000 title claims abstract description 67
- 229960003453 cannabinol Drugs 0.000 title claims abstract description 67
- 239000008157 edible vegetable oil Substances 0.000 title claims abstract description 47
- 239000000126 substance Substances 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims abstract description 33
- 238000001514 detection method Methods 0.000 claims abstract description 47
- 238000000746 purification Methods 0.000 claims abstract description 30
- 238000000605 extraction Methods 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 33
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 claims description 30
- CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 claims description 23
- QHMBSVQNZZTUGM-UHFFFAOYSA-N Trans-Cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-UHFFFAOYSA-N 0.000 claims description 23
- QHMBSVQNZZTUGM-ZWKOTPCHSA-N cannabidiol Chemical compound OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-ZWKOTPCHSA-N 0.000 claims description 23
- 229950011318 cannabidiol Drugs 0.000 claims description 23
- PCXRACLQFPRCBB-ZWKOTPCHSA-N dihydrocannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)C)CCC(C)=C1 PCXRACLQFPRCBB-ZWKOTPCHSA-N 0.000 claims description 23
- 229960004242 dronabinol Drugs 0.000 claims description 23
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 claims description 12
- 238000004949 mass spectrometry Methods 0.000 claims description 10
- 238000010811 Ultra-Performance Liquid Chromatography-Tandem Mass Spectrometry Methods 0.000 claims description 9
- 238000004451 qualitative analysis Methods 0.000 claims description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- 238000004445 quantitative analysis Methods 0.000 claims description 8
- 238000010813 internal standard method Methods 0.000 claims description 6
- 238000004458 analytical method Methods 0.000 claims description 5
- 239000010460 hemp oil Substances 0.000 claims description 5
- 238000001819 mass spectrum Methods 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 230000009977 dual effect Effects 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 238000013467 fragmentation Methods 0.000 claims description 4
- 238000006062 fragmentation reaction Methods 0.000 claims description 4
- 238000002347 injection Methods 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- 238000012544 monitoring process Methods 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims description 4
- 239000007921 spray Substances 0.000 claims description 4
- 239000000944 linseed oil Substances 0.000 claims description 3
- 235000021388 linseed oil Nutrition 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 238000010828 elution Methods 0.000 claims description 2
- 239000000523 sample Substances 0.000 abstract description 30
- 238000011084 recovery Methods 0.000 abstract description 17
- 230000000694 effects Effects 0.000 abstract description 10
- 239000011159 matrix material Substances 0.000 abstract description 9
- 239000012535 impurity Substances 0.000 abstract description 6
- 230000035945 sensitivity Effects 0.000 abstract description 6
- 239000012521 purified sample Substances 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- 150000002500 ions Chemical group 0.000 description 19
- 239000007788 liquid Substances 0.000 description 6
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 4
- 239000002048 multi walled nanotube Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000004885 tandem mass spectrometry Methods 0.000 description 4
- 238000001195 ultra high performance liquid chromatography Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 239000012086 standard solution Substances 0.000 description 3
- 241000218236 Cannabis Species 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002086 nanomaterial Substances 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 229930182558 Sterol Natural products 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- -1 saccharide sterols Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
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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
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
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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
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
- G01N30/08—Preparation using an enricher
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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
- G01N30/62—Detectors specially adapted therefor
- G01N30/72—Mass spectrometers
- G01N30/7233—Mass spectrometers interfaced to liquid or supercritical fluid chromatograph
- G01N30/724—Nebulising, aerosol formation or ionisation
- G01N30/7266—Nebulising, aerosol formation or ionisation by electric field, e.g. electrospray
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- G01N30/86—Signal analysis
- G01N30/8675—Evaluation, i.e. decoding of the signal into analytical information
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- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N2030/042—Standards
- G01N2030/045—Standards internal
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- 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
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Abstract
The invention provides a detection method of cannabinol substances in edible oil, and relates to the technical field of edible oil detection. Aiming at the problems of time and labor waste caused by the complexity of a matrix in the existing edible oil cannabinol substance detection process, the detection method improves the pretreatment process of a sample to be detected, the sample to be detected is firstly added into an extraction solvent and is uniformly mixed, then the sample is purified in an HLB purification column, a QuEChERS purification column or a Sin-QuEChERS purification column, and the purified sample to be detected can effectively avoid the interference of the matrix after detection, so that the impurity purification effect is obvious; meanwhile, the detection method for detecting the cannabinol substances in the edible oil has the advantages of high recovery rate, high detection sensitivity and high accuracy.
Description
Technical Field
The invention relates to the technical field of edible oil detection, in particular to a detection method of cannabinol substances in edible oil.
Background
At present, due to the complexity of the matrix, the detection of the cannabinol substances is generally time-consuming and labor-consuming, and particularly in the optimization of the pretreatment method, the most suitable pretreatment method is needed to be found for different matrixes.
Therefore, developing a suitable purification method for edible oil is of great importance in developing a method capable of rapidly detecting cannabinol, cannabidiol and tetrahydrocannabinol in edible oil.
In view of this, the present invention has been made.
Disclosure of Invention
The invention aims to provide a detection method of cannabinol substances in edible oil, which can effectively avoid the interference of matrixes and has obvious impurity purification effect; meanwhile, the detection method for detecting the cannabinol substances in the edible oil has the technical advantages of high recovery rate, high detection sensitivity and high detection accuracy.
In order to achieve the above object of the present invention, the following technical solutions are specifically adopted:
the invention provides a detection method of cannabinol substances in edible oil, which comprises the following steps:
(A) Pretreatment: adding a sample to be tested into an extraction solvent, uniformly mixing, and then passing through a purification column to obtain a sample to be tested;
the purifying column comprises any one of an HLB purifying column, a QuEChERS purifying column and a Sin-QuEChERS purifying column;
(B) And (3) detection: detecting a sample to be detected by using ultra-high performance liquid chromatography-tandem mass spectrometry, and carrying out qualitative and quantitative analysis on cannabinol substances;
the cannabinols include cannabinol, cannabidiol and tetrahydrocannabinol.
Further, the edible oil comprises at least one of hemp oil (hemp oil) and linseed oil.
Further, the extraction solvent in the step (a) includes one of methanol or acetonitrile, preferably methanol.
Further, the purifying column in the step (A) is a Sin-QuEChERS purifying column.
Further, the method for performing qualitative and quantitative analysis on the cannabinol substances in the step (B) comprises the following steps:
qualitative analysis is carried out on cannabinol substances by adopting the abundance ratio of secondary ion fragments;
and quantitatively analyzing the cannabinol substances by adopting an internal standard method.
Further, the internal standard for quantitatively analyzing the cannabinol substance by adopting an internal standard method is deuterated tetrahydrocannabinol.
Further, the chromatographic conditions of the ultra performance liquid chromatography-tandem mass spectrometry in the step (B) include:
liquid phase analysis chromatographic column: c18 (3.5 μm, 2.1X100 mm);
column temperature: 35 ℃; sample injection amount: 10. Mu.L;
phase A is 0.01% formic acid aqueous solution and phase B is methanol.
Furthermore, the gradient elution program of the ultra-high performance liquid chromatography-tandem mass spectrum in volume percent is as follows:
further, the mass spectrometry conditions of the ultra performance liquid chromatography-tandem mass spectrometry in the step (B) are as follows:
ion source: electrospray dual spray ion source;
the detection mode is as follows: a positive ion mode;
mass spectrometry scanning mode: monitoring multiple reactions;
atomizer pressure: 45psi;
gas temperature: 350 ℃; gas flow rate: 5L/min;
sheath temperature: 300 ℃; sheath air flow rate: 11L/min;
capillary voltage: 4000V; fragmentation voltage: 135V.
Further, the parent ion, the daughter ion, the residence time and the collision energy in the mass spectrometry conditions of the ultra performance liquid chromatography-tandem mass spectrometry in the step (B) are as follows:
compared with the prior art, the invention has the beneficial effects that:
the invention provides a detection method of cannabinol substances in edible oil, which quantitatively and qualitatively detects the cannabinol substances (cannabinol, cannabidiol and tetrahydrocannabinol) in the edible oil by utilizing ultra-high performance liquid chromatography-tandem mass spectrometry. Aiming at the problems of time and labor waste caused by the complexity of a matrix in the existing edible oil cannabinol substance detection process, the detection method for research and development improves the pretreatment process of a sample to be detected, firstly, the sample to be detected is added into an extraction solvent and is uniformly mixed, then, the sample is purified in an HLB purification column, a QuEChERS purification column or a Sin-QuEChERS purification column, and the purified sample to be detected is detected, so that the interference of the matrix can be effectively avoided, and the impurity purification effect is obvious; meanwhile, the detection method for detecting the cannabinol substances in the edible oil has the technical advantages of high recovery rate, high detection sensitivity and high detection accuracy.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings that are needed in the description of the embodiments or the prior art will be briefly described, and it is obvious that the drawings in the description below are some embodiments of the present invention, and other drawings can be obtained according to the drawings without inventive effort for a person skilled in the art.
FIG. 1 is a total ion flow diagram of edible oil samples according to example 1 of the present invention;
FIG. 2 is a graph showing the effect of methanol and acetonitrile on extraction efficiency provided in example 3 of the present invention;
FIG. 3 shows the effect of different types of purification columns provided in example 4 of the present invention on extraction efficiency.
Detailed Description
The technical solutions of the present invention will be clearly and completely described in connection with the embodiments, and it is apparent that the described embodiments are some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
According to one aspect of the invention, a method for detecting cannabinol substances in edible oil comprises the following steps:
(A) Pretreatment: adding a sample to be tested into an extraction solvent, uniformly mixing, and then passing through a purification column to obtain a sample to be tested;
the purifying column comprises any one of an HLB purifying column, a QuEChERS purifying column and a Sin-QuEChERS purifying column;
(B) And (3) detection: detecting a sample to be detected by using ultra-high performance liquid chromatography-tandem mass spectrometry, and carrying out qualitative and quantitative analysis on cannabinol substances;
the cannabinols include cannabinol, cannabidiol and tetrahydrocannabinol.
The invention provides a detection method of cannabinol substances in edible oil, which quantitatively and qualitatively detects the cannabinol substances (cannabinol, cannabidiol and tetrahydrocannabinol) in the edible oil by utilizing ultra-high performance liquid chromatography-tandem mass spectrometry. Aiming at the problems of time and labor waste caused by the complexity of a matrix in the existing edible oil cannabinol substance detection process, the detection method for research and development improves the pretreatment process of a sample to be detected, firstly, the sample to be detected is added into an extraction solvent and is uniformly mixed, then, the sample is purified in an HLB purification column, a QuEChERS purification column or a Sin-QuEChERS purification column, and the purified sample to be detected is detected, so that the interference of the matrix can be effectively avoided, and the impurity purification effect is obvious; meanwhile, the detection method for detecting the cannabinol substances in the edible oil has the technical advantages of high recovery rate, high detection sensitivity and high detection accuracy.
The QuEChERS method is a rapid sample pretreatment technique for agricultural product detection developed by Anastassiades, U.S. department of agriculture, taught in 2003, by pulverizing the sample, extracting with acetonitrile, and adding anhydrous MgSO 4 Removing water by the salt, adding adsorbent such as ethylenediamine-N-Propylsilane (PSA), removing impurities, and collecting supernatant. The method combines with high-sensitivity liquid chromatography-mass spectrometry, and has the advantages of simplicity, high recovery rate, etc.
The Sin-QuEChERS purifying column is based on the improvement of QuEChERS, solid-phase adsorption materials such as multi-wall carbon nano tube PSA with larger specific surface area are combined, a sample is placed in a centrifuge tube, acetonitrile is added into the centrifuge tube for vortex oscillation and centrifugation, the Sin-QuEChERS small column is inserted into the centrifuge tube, the Sin-QuEChERS small column is pressed to obtain supernatant purifying liquid, and the purifying liquid can be directly injected. The method can improve matrix interference removing effect, such as purifying pigment, lipid, and part of saccharide sterols, and reduce chromatogram interference. Compared with other extraction and purification methods, the method has the advantages of simple operation, obvious impurity purification effect, less pesticide adsorption, accurate result and the like, and can greatly shorten analysis time. However, the current Sin-QuEChERS pretreatment technology is still in a starting stage and has not been used in the field of detection of grease edible oil. The QuEChERS and Sin-QuEChERS pretreatment purification method is less in detection study on the food oil substrate.
In a preferred embodiment of the present invention, the edible oil includes at least one of hemp oil (hemp oil) and linseed oil.
In a preferred embodiment of the present invention, the extraction solvent in step (a) comprises one of methanol or acetonitrile, preferably methanol.
As a preferred embodiment, the extraction solvent comprises methanol or acetonitrile, preferably methanol.
In a preferred embodiment of the present invention, the purification column in step (A) is a Sin-QuEChERS purification column.
As a preferred embodiment, the Sin-QuEChERS purifying column is obtained by combining a novel composite nanomaterial (MWCNTs) with a solid-phase adsorption material such as PSA (pressure sensitive adhesive) and the like, and the MWCNTs have strong pigment removing capability superior to GCB (dye-removing agent), carb and the like in removing other macromolecular interfering substances in a matrix because the nanomaterial (MWCNTs) has the advantage of large specific surface area.
In a preferred embodiment of the present invention, the method for qualitative and quantitative analysis of cannabinol substances in step (B) comprises:
qualitative analysis is carried out on cannabinol substances by adopting the abundance ratio of secondary ion fragments; and quantitatively analyzing the cannabinol substances by adopting an internal standard method.
In a preferred embodiment, the internal standard for quantitative analysis of cannabinols by internal standard method is deuterated tetrahydrocannabinol.
Preferably, the concentration of deuterated tetrahydrocannabinol as internal standard is 100 μg/L.
In a preferred embodiment of the present invention, the chromatographic conditions of the ultra performance liquid chromatography-tandem mass spectrometry in the step (B) include:
liquid phase analysis chromatographic column: c18 (3.5 μm, 2.1X100 mm);
column temperature: 35 ℃; sample injection amount: 10. Mu.L;
phase A is 0.01% formic acid aqueous solution and phase B is methanol.
In a preferred embodiment of the present invention, the gradient elution procedure of the ultra-high performance liquid chromatography-tandem mass spectrometry in volume percent is:
in a preferred embodiment of the present invention, the mass spectrometry conditions of the ultra performance liquid chromatography-tandem mass spectrometry in the step (B) are as follows:
ion source: electrospray dual spray ion source;
the detection mode is as follows: a positive ion mode;
mass spectrometry scanning mode: monitoring multiple reactions;
atomizer pressure: 45psi;
gas temperature: 350 ℃; gas flow rate: 5L/min;
sheath temperature: 300 ℃; sheath air flow rate: 11L/min;
capillary voltage: 4000V; fragmentation voltage: 135V.
In a preferred embodiment of the present invention, the parent ion, the daughter ion, the residence time and the collision energy in the mass spectrometry conditions of the ultra performance liquid chromatography-tandem mass spectrometry in the step (B) are as follows:
the technical scheme of the invention will be further described with reference to examples.
Example 1
(1) Drawing a standard curve:
methanol is used as a solvent to prepare a series of standard solutions with the standard substance concentration of cannabinol, cannabidiol and tetrahydrocannabinol of 0.03-0.61ng/ml, 10 mu L of internal standard (0.1 g/L of deuterated tetrahydrocannabinol) is added, and the internal standard solution is detected by ultra-high performance liquid chromatography tandem mass spectrometry to establish an internal standard curve.
The chromatographic conditions of the ultra-high performance liquid chromatography-tandem mass spectrometry comprise:
liquid phase analysis chromatographic column: c18 (3.5 μm, 2.1X100 mm);
column temperature: 35 ℃; sample injection amount: 10. Mu.L;
phase A is 0.01% formic acid aqueous solution and phase B is methanol.
The gradient elution program of the ultra-high performance liquid chromatography-tandem mass spectrum in volume percent is as follows:
the mass spectrum conditions of the ultra-high performance liquid chromatography-tandem mass spectrum are as follows:
ion source: electrospray dual spray ion source;
the detection mode is as follows: a positive ion mode;
mass spectrometry scanning mode: monitoring multiple reactions;
atomizer pressure: 45psi;
gas temperature: 350 ℃; gas flow rate: 5L/min;
sheath temperature: 300 ℃; sheath air flow rate: 11L/min;
capillary voltage: 4000V; fragmentation voltage: 135V.
Parent ions, daughter ions, residence time and collision energy in the mass spectrometry conditions were as follows:
the standard curve of the internal standard method is as follows:
CBD (cannabidiol): y=0.0257271 x-0.0724792 r2= 0.9996;
CBN (cannabinol): y=0.0144328 x-0.0282827 r2= 0.9992;
THC (tetrahydrocannabinol): y=0.0590091 x-0.0689841 r2=0.9999;
detection result: the standard curve has good linear relation between 0.03 and 0.61ng/ml, and the correlation coefficient is more than 0.999.
(2) Recovery rate:
taking a blank edible oil sample, adding cannabinol, cannabidiol and tetrahydrocannabinol mixed standard solution, adding standard amounts of 0.03ng/g, 0.31ng/g and 0.61ng/g respectively, adding 10 mu L of internal standard (deuterated tetrahydrocannabinol 0.1 g/L), extracting with methanol, passing through a Sin-QuEChERS purifying column to obtain a purifying liquid to be detected, detecting by ultra-high performance liquid chromatography tandem mass spectrometry, and calculating the standard adding recovery rate. The labeling recovery is shown in the following table:
as shown in the table, the cannabinol labeled recovery rate is 101.71-114.50%, the cannabidiol labeled recovery rate is 98.75-106.13%, the tetrahydrocannabinol labeled recovery rate is 100.28-107.06%, the relative standard deviation is less than 10%, and the sensitivity and the accuracy are higher.
Fig. 1 is a total ion flow diagram of edible oil sample detection.
Example 2
Taking a blank edible oil sample, adding 10 mu L of an internal standard (0.1 g/L of deuterated tetrahydrocannabinol), diluting the concentration of the standard sample by 2000 times, and detecting by using the ultra-high performance liquid chromatography-tandem mass spectrometry according to the conditions of the ultra-high performance liquid chromatography-tandem mass spectrometry of the embodiment 1, wherein the detection limit is 3 times of signal to noise ratio (S/N).
Detection result: the detection limit of each of cannabinol, cannabidiol and tetrahydrocannabinol is 0.01ng/g.
The standard curve detection limit and the correlation coefficient are shown in the following table:
| compounds of formula (I) | Range ng/ml | Correlation coefficient | Detection limit ng/g | Quantitative limit ng/g |
| Cannabinol | 0.03-0.61 | 0.999 | 0.01 | 0.03 |
| Cannabidiol | 0.03-0.61 | 0.999 | 0.01 | 0.03 |
| Tetrahydrocannabinol | 0.03-0.61 | 0.999 | 0.01 | 0.03 |
Example 3
Preparing two identical samples to be tested of cannabis oil, wherein one group of extraction solvents is methanol, and the other group of extraction solvents is acetonitrile;
the extraction efficiencies of the different extraction solvents for cannabinol, cannabidiol and tetrahydrocannabinol in the samples were compared by ultra-high performance liquid chromatography tandem mass spectrometry detection according to the conditions of the ultra-high performance liquid chromatography-tandem mass spectrometry of example 1.
FIG. 2 is a graph showing the effect of methanol and acetonitrile on extraction efficiency.
As can be seen from fig. 2: methanol recovery rates for cannabinol, cannabidiol and tetrahydrocannabinol were 98.12%, 102.31% and 95.44%, respectively;
the recovery rates of acetonitrile for cannabinol, cannabidiol and tetrahydrocannabinol were 84.11%, 88.52% and 86.71%, respectively. From this, it is clear that the extraction efficiency of methanol is higher than acetonitrile for cannabinol, cannabidiol and tetrahydrocannabinol in the edible oil sample.
Example 4
Preparing four identical samples to be tested of cannabis oil, wherein three groups of purifying columns are respectively an HLB purifying column, a QuEChERS purifying column and a Sin-QuEChERS purifying column, and the other sample is filtered only;
the extraction efficiencies of the purification column for cannabinol, cannabidiol and tetrahydrocannabinol in the samples were compared by ultra-high performance liquid chromatography tandem mass spectrometry detection according to the conditions of ultra-high performance liquid chromatography-tandem mass spectrometry of example 1.
Fig. 3 is an illustration of the effect of different types of purification columns on extraction efficiency.
As can be seen from fig. 3, after the HLB purification column treatment, the recovery rates of cannabinol, cannabidiol and tetrahydrocannabinol in the edible oil sample were 89.21%, 83.71% and 88.01%, respectively;
after QuEChERS treatment, the recovery rates of cannabinol, cannabidiol and tetrahydrocannabinol in the edible oil sample are 84.41%, 99.52% and 93.11% respectively;
after being treated by a Sin-QuEChERS purifying column, the recovery rates of the cannabinol, the cannabidiol and the tetrahydrocannabinol in the edible oil sample are 104.13%, 101.91% and 97.91%, respectively.
In addition, the recovery rates of cannabinol, cannabidiol and tetrahydrocannabinol in the edible oil samples were 74.21%, 56.88% and 78.35%, respectively, by filtration alone, without pretreatment using a purification column.
Therefore, the extraction efficiency of Sin-QuEChERS purification columns was higher than that of HLB purification columns and QuEChERS for cannabinol, cannabidiol, and tetrahydrocannabinol in the edible oil samples.
In conclusion, the method for detecting the cannabinol substances in the edible oil has the advantages of simplicity in operation, high efficiency, organic solvent saving, accurate qualitative and quantitative properties and high sensitivity through optimization of the solvent extraction and purification columns.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present invention, and not for limiting the same; although the invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments can be modified or some or all of the technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit of the invention.
Claims (10)
1. The detection method of the cannabinol substances in the edible oil is characterized by comprising the following steps of:
(A) Pretreatment: adding a sample to be tested into an extraction solvent, uniformly mixing, and then passing through a purification column to obtain a sample to be tested;
the purifying column comprises any one of an HLB purifying column, a QuEChERS purifying column and a Sin-QuEChERS purifying column;
(B) And (3) detection: detecting a sample to be detected by using ultra-high performance liquid chromatography-tandem mass spectrometry, and carrying out qualitative and quantitative analysis on cannabinol substances;
the cannabinols include cannabinol, cannabidiol and tetrahydrocannabinol.
2. The method for detecting cannabinol in edible oil as claimed in claim 1, wherein the edible oil comprises at least one of hemp oil and linseed oil.
3. The method for detecting cannabinol in edible oil as claimed in claim 1, wherein the extraction solvent in step (a) comprises one of methanol or acetonitrile, preferably methanol.
4. The method for detecting cannabinol in edible oil as claimed in claim 1, wherein the purifying column in the step (a) is a Sin-QuEChERS purifying column.
5. The method for detecting cannabinol in edible oil as claimed in claim 1, wherein the method for qualitative and quantitative analysis of cannabinol in step (B) comprises:
qualitative analysis is carried out on cannabinol substances by adopting the abundance ratio of secondary ion fragments;
and quantitatively analyzing the cannabinol substances by adopting an internal standard method.
6. The method for detecting cannabinol in edible oil as claimed in claim 5, wherein the internal standard for quantitative analysis of cannabinol is deuterated tetrahydrocannabinol.
7. The method for detecting cannabinol in edible oil as claimed in claim 1, wherein the chromatographic conditions of ultra performance liquid chromatography-tandem mass spectrometry in step (B) comprise:
liquid phase analysis chromatographic column: c18 (3.5 μm, 2.1X100 mm);
column temperature: 35 ℃; sample injection amount: 10. Mu.L;
phase A is 0.01% formic acid aqueous solution and phase B is methanol.
8. The method for detecting cannabinol in edible oil as claimed in claim 6, wherein the gradient elution procedure of ultra-high performance liquid chromatography-tandem mass spectrometry in volume percent is as follows:
9. the method for detecting cannabinol in edible oil as claimed in claim 1, wherein the mass spectrometry conditions of the ultra performance liquid chromatography-tandem mass spectrometry in the step (B) are as follows:
ion source: electrospray dual spray ion source;
the detection mode is as follows: a positive ion mode;
mass spectrometry scanning mode: monitoring multiple reactions;
atomizer pressure: 45psi;
gas temperature: 350 ℃; gas flow rate: 5L/min;
sheath temperature: 300 ℃; sheath air flow rate: 11L/min;
capillary voltage: 4000V; fragmentation voltage: 135V.
10. The method for detecting cannabinol in edible oil as claimed in claim 1, wherein the mass spectrum conditions of the ultra performance liquid chromatography-tandem mass spectrometry in the step (B) are as follows:
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