CN107478746A - The chiral analysis of nicotine and nornicotine close phase chromatographic tandem mass spectrography in a kind of electronic cigarette liquid - Google Patents
The chiral analysis of nicotine and nornicotine close phase chromatographic tandem mass spectrography in a kind of electronic cigarette liquid Download PDFInfo
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- CN107478746A CN107478746A CN201710698786.2A CN201710698786A CN107478746A CN 107478746 A CN107478746 A CN 107478746A CN 201710698786 A CN201710698786 A CN 201710698786A CN 107478746 A CN107478746 A CN 107478746A
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- nornicotine
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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
- G01N2030/062—Preparation extracting sample from raw material
Abstract
The invention discloses the chiral analysis of nicotine and nornicotine in a kind of electronic cigarette liquid to close phase chromatographic tandem mass spectrography.It is characterized in that:By electronic cigarette liquid sample after sodium hydroxide solution infiltrates, using n-hexane/methanol solution extraction, extract is after Dispersive solid phase extraction purifies, phase chromatographic tandem analytical reagent composition is closed using two chiral column series connection, S () nicotine in electronic cigarette liquid is quantitatively detected using areas of peak normalization method, the ratio of R (+) nicotine, S () nornicotine and R (+) nornicotine.The detection method that this method provides, sample extraction purification method is simply efficient, pollution of the sample liquid to chromatographic column can be reduced, close phase chromatographic tandem mass spectrography detection method high sensitivity, specificity is good, false positive can be excluded, analysis time is short, disclosure satisfy that the chiral analysis of nicotine and nornicotine in high-volume electronic cigarette liquid sample.
Description
Technical field
The present invention relates to electronic cigarette liquid chemical constituents determination method, and in particular to nicotine and nornicotine in a kind of electronic cigarette liquid
Chiral analysis close phase chromatographic tandem mass spectrography.
Background technology
Nicotine and nornicotine, are the main alkaloids being present in plant of Solanaceae, and one of important component of tobacco.Cigarette
Alkali and nornicotine molecule contain a chiral centre, so there is two enantiomers:S- (-)-nicotine, R- (+)-nicotine, S- (-)-
Nornicotine and R- (+)-nornicotine.Two enantiomers of nicotine and nornicotine have entirely different content, metabolic mechanism and physiology
Characteristic.Therefore the chiral analysis of nicotine and nornicotine in electronic cigarette liquid need to be carried out.
At present, document report nicotine and the assay method of nornicotine enantiomter mainly have gas chromatography-mass spectrography
Method(GC-MS), multidimensional gas chromatographic-MS(MDGC-MS), capillary electrophoresis(CE)Deng, still, GC-MS and
MDGC-MS needs to perform the derivatization in pretreatment process, wastes time and energy, and CE is used only retention time and carries out qualitative, qualitative energy
Power is relatively poor, false positive results easily occurs.It is therefore desirable to develop, a kind of high sensitivity, precision are good, are adapted to high-volume
The method of S- (-)-nicotine in accurate quantitative analysis electronic cigarette liquid, R- (+)-nicotine, S- (-)-nornicotine and R- (+)-nornicotine.
Chiral column-conjunction phase chromatographic tandem mass spectrum has obvious advantage in terms of isomer separation, therefore by a large amount of real
Test and establish nicotine and chiral column-conjunction phase chromatographic tandem mass spectrometric analysis method of nornicotine chirality in electronic cigarette liquid, this method is more
It is suitable for the chiral analysis of nicotine and nornicotine in a large amount of samples.
The content of the invention
The purpose of the present invention is exactly using nicotine and nornicotine as research object, carry out pre-treatment side to electronic cigarette liquid sample
Method research, establish nicotine and nornicotine optical isomerism in series connection chiral column-conjunction phase chromatographic tandem mass spectrography detection electronic cigarette liquid
The analysis method of body, realize the Accurate Determining to nicotine in electronic cigarette liquid and nornicotine optical antipode.
The purpose of the present invention is achieved through the following technical solutions:Electronic cigarette liquid sample is passed through into sodium hydroxide solution
After infiltration, using n-hexane/methanol solution extraction, extract after Dispersive solid phase extraction purifies, using series connection chiral column-
Phase chromatographic tandem analytical reagent composition is closed, R- (+)-nicotine in electronic cigarette liquid is quantitatively detected using areas of peak normalization method and accounts for total nicotine
Ratio, S- (-)-nornicotine accounts for the ratio of total nornicotine.Comprise the following steps that:
1. the preparation of standard liquid:Weigh about 100.0 mg S- (-)-nicotine, R- (+)-nicotine, S- (-)-nornicotine and R-
(+)-nornicotine standard items, constant volume are diluted into 50 mL brown volumetric flasks with methanol solution, it is about 2.0 mg/ to be configured to concentration
ML standard reserving solution;Diluted using standard reserving solution and prepare S- (-)-nicotine, R- (+)-nicotine, S- (-)-nornicotine and R-
(+)-nornicotine concentration is 100 μ g/mL mixed standard solution.2. the mixing of electronic cigarette liquid sample:By electronic cigarette liquid sample whirlpool
Revolve 1 min mixings.
3. the extraction of electronic cigarette liquid sample:Weigh the sample that 0.3 g has been crushed in 15 mL to have in plug centrifuge tube, add
2.0 mL 5%(Mass ratio)Sodium hydroxide solution, be vortexed 1 min mix after stand 10 min infiltration sample.Take 10 mL just oneself
Alkane/methanol(98:2, V/V)Solution into centrifuge tube, and on vortex mixer with the min of 4000 rpm velocity fluctuations 30.
4. the purification of extract:1.5 mL supernatants are taken to be purified in 2 mL in centrifuge tube(Include 150 mg anhydrous slufuric acids
Magnesium, 50mg PSA adsorbents, 25 mg GCB adsorbents, it is referred to as Dispersive solid phase extraction material), on vortex mixer with
4000 rpm vibrate 2 min, and 1 min is centrifuged with 10000 rpm.Supernatant is taken to cross 0.45 μm of organic phase filter membrane laggard liquid phase point
Analysis.
5. chiral column-conjunction phase chromatographic tandem mass spectrography condition of connecting:Analytical column 1 is Trefoil CEL1 posts(Column length 150
Mm, the mm of internal diameter 3.0,2.5 μm of stationary phase particle diameter), analytical column 2 is Chiralcel OD-H liquid-phase chromatographic column (column lengths 250
Mm, the mm of internal diameter 4.6,5 μm of stationary phase particle diameter);Mobile phase A is:CO2, Mobile phase B:Methanol containing 0.05% isopropylamine;Stream
Speed is 1.0 mL/min;Condition of gradient elution is:0.0 min, 97% A;0.5 min, 97% A;8.0 min, 92% A;12.0
Min, 92% A;30.0 min, 90% A.40 DEG C of column temperature;Sample introduction room temperature:10 ℃;The μ L of sampling volume 2;Back pressure:1600
psi;ISM compensation flow paths are mutually the methanol containing 0.1% formic acid, and flow velocity is 0.3 mL/min.Analysis time amounts to 30 min.
Mass Spectrometry Conditions:Ion gun:Electrospray ionization source, scan mode scan for cation, and ion source temperature is 300 DEG C, and electron spray voltage is
5000 V, atomization gas pressure are 40 psi;Detection mode:Multiple-reaction monitoring(MRM);MRM parameters see the table below.By to peak area
The ratio that quantitative R- (+)-nicotine accounts for total nicotine is normalized, S- (-)-nornicotine accounts for the ratio of total nornicotine.
The invention provides the chiral analysis of nicotine and nornicotine in a kind of electronic cigarette liquid to close phase chromatographic tandem mass spectrography, tool
There are following excellent results:Pollution of the sample liquid to chromatographic column can be reduced, closes phase chromatographic tandem mass spectrography detection method high sensitivity,
Specificity is good, can avoid false positive, analysis time is short, can realize the baseline separation to nicotine and nornicotine enantiomter, energy
Enough meet the chiral analysis of nicotine and nornicotine in high-volume electronic cigarette liquid sample.
Brief description of the drawings
Fig. 1 is the chromatogram of mixed standard solution,
Fig. 2 is the chromatogram of electronic cigarette liquid sample.
Embodiment
The present invention is further described by specific examples below, but does not limit the present invention.
1. instrument and reagent
ACQUITY UPC2 ultra high efficiencies close chromatography(Waters, US), 6410B triplex tandem level Four bar mass spectrographs(It is beautiful
Agilent companies of state), AE163 electronic balances(Sensibility reciprocal:0.0001 g, Mettler companies of Switzerland), high speed disintegrator(Wuhan silver
Color Science and Technology Ltd.), U.S.'s ColeparmerVotex-Genie turbula shakers, German SIGMA 3-30K- high speed desktops
Frozen type centrifuge.N-hexane(Chromatographically pure), sodium hydroxide(Analyze pure), formic acid(Chromatographically pure), methanol(Chromatographically pure), S- (-)-
Nicotine standard product, R- (+)-nicotine standard product, S- (-)-nornicotine standard items, R- (+)-nornicotine standard items.
2. the preparation of standard liquid
About 100.0 mg S- (-)-nicotine, R- (+)-nicotine, S- (-)-nornicotine and R- (+)-nornicotine standard items are weighed, are used
Methanol solution dilutes constant volume into 50 mL brown volumetric flasks, is configured to the standard reserving solution that concentration is about 2.0 mg/mL;Utilize
S- (-)-nicotine is prepared in standard reserving solution dilution, and R- (+)-nicotine, S- (-)-nornicotine and R- (+)-nornicotine concentration are 100 μ
G/mL mixed standard solution.
3. the mixing of electronic cigarette liquid sample:1 min of electronic cigarette liquid sample vortex is mixed.
4. the extraction of electronic cigarette liquid sample:Weigh the sample that 0.3 g has been crushed in 15mL to have in plug centrifuge tube, add
2.0mL 5% sodium hydroxide solution, vortex 1min stand 10 min infiltration samples after mixing.Take 10 mL n-hexanes/methanol molten
Liquid(98:2, V/V)Solution into centrifuge tube, and on vortex mixer with the min of 4000 rpm velocity fluctuations 30.
5. the purification of extract:1.5 mL supernatants are taken to be purified in 2 mL in centrifuge tube(Include 150 mg anhydrous slufuric acids
Magnesium, 50 mg PSA adsorbents, 25 mg GCB adsorbents), in vibrating 2 min on vortex mixer with 4000 rpm, with 10000
Rpm centrifuges 1min.Supernatant is taken to cross 0.45 μm of laggard liquid phase analysis of organic phase filter membrane.
6. chiral column-conjunction phase chromatographic tandem mass spectrography condition of connecting:Analytical column 1 is Trefoil CEL1 posts(Column length 150
Mm, the mm of internal diameter 3.0,2.5 μm of stationary phase particle diameter), analytical column 2 is Chiralcel OD-H liquid-phase chromatographic column (column lengths 250
Mm, the mm of internal diameter 4.6,5 μm of stationary phase particle diameter);Mobile phase A is:CO2, Mobile phase B:Methanol containing 0.05% isopropylamine;Stream
Speed is 1.0 mL/min;Condition of gradient elution is:0.0 min, 97% A;0.5 min, 97% A;8.0 min, 92% A;12.0
Min, 92% A;30.0 min, 90% A.40 DEG C of column temperature;Sample introduction room temperature:10 ℃;The μ L of sampling volume 2;Back pressure:1600
psi;ISM compensation flow paths are mutually the methanol containing 0.1% formic acid, and flow velocity is 0.3 mL/min.Analysis time amounts to 30 min.
Mass Spectrometry Conditions:Ion gun:Electrospray ionization source, scan mode scan for cation, and ion source temperature is 300 DEG C, and electron spray voltage is
5000 V, atomization gas pressure are 40 psi;Detection mode:Multiple-reaction monitoring(MRM);MRM parameters are shown in institute's subordinate list in the content of the invention.
The ratio of total nornicotine is accounted for by peak area being normalized quantitative S- (-)-nornicotine and R- (+)-nornicotine.
7. the detection limit of R- (+)-nicotine and R- (+)-nornicotine
The chiral composition of nicotine generally accounts for the percentage of total nicotine to represent with R- (+)-nicotine.The chiral composition of nornicotine is usual
The percentage of total nornicotine is accounted for R- (+)-nornicotine to represent.To assess the detection of R- (+)-nicotine and R- (+)-nornicotine
Limit, the inventive method add R- (+)-nicotine and R- (+)-drop cigarette in the standard liquid of S- (-)-nicotine and S- (-)-nornicotine
The standard liquid of alkali.As a result show, the detection of R- (+)-nicotine is limited to 0.01%(Peak area is relative to total nicotine peak area), R-
The detection of (+)-nornicotine is limited to 0.1%(Peak area is relative to total nornicotine peak area), in this, as the detection limit of this method.
8. the chiral analysis example of nicotine and nornicotine in electronic cigarette liquid sample
The electronic cigarette liquid sample handled according to above-mentioned steps is carried out to close phase chromatographic tandem mass spectral analysis;Using nicotine and nornicotine
MRM ions carry out qualitative analysis, and quantitative R- (+)-nicotine and R- (+)-nornicotine are normalized to peak area and accounts for total ratio.
10 electronic cigarette liquid samples are analyzed using this method, the results are shown in Table 1.
9. the precision of analysis method
Take same electronic cigarette liquid sample to carry out 5 times in a few days and parallel determination in the daytime, investigate the precision of the inventive method, as a result
It is shown in Table 2 and table 3.As a result show, the change of the in a few days measurement result of R- (+)-nicotine and R- (+)-nornicotine in electronic cigarette liquid sample
Different coefficient is respectively 5.93% and 4.75%, and the coefficient of variation of measurement result is respectively 3.65% and 1.79% in the daytime, and precision is preferable.
Above-mentioned 10 electronic cigarette liquid samples are detected using the method in embodiment.Detect obtained color
Spectrogram is as depicted in figs. 1 and 2.
Claims (3)
1. the chiral analysis of nicotine and nornicotine close phase chromatographic tandem mass spectrography in a kind of electronic cigarette liquid, it is characterised in that:By electricity
Sub- tobacco juice sample is after sodium hydroxide solution infiltrates, and using n-hexane/methanol solution extraction, extract is through matrix dispersed solid phase
After extracting and purifying, using chiral column-conjunction phase chromatographic tandem mass spectral analysis, electronic cigarette liquid is quantitatively detected using areas of peak normalization method
The ratio of middle S- (-)-nicotine, R- (+)-nicotine, S- (-)-nornicotine and R- (+)-nornicotine, is comprised the following steps that:
1) preparation of standard liquids:Weigh about 100.0 mg S- (-)-nicotine, R- (+)-nicotine, S- (-)-nornicotine and R-
(+)-nornicotine standard items, constant volume are diluted into 50 mL brown volumetric flasks with methanol solution, it is about 2.0 mg/ to be configured to concentration
ML standard reserving solution;Diluted using standard reserving solution and prepare S- (-)-nicotine, R- (+)-nicotine, S- (-)-nornicotine and R-
(+)-nornicotine concentration is 100 μ g/mL mixed standard solution;
2) mixing of electronic cigarette liquids sample:1 min of electronic cigarette liquid sample vortex is mixed;
3) extraction of electronic cigarette liquids sample:Weigh the sample that 0.3 g has been crushed in 15 mL to have in plug centrifuge tube, add 2.0
ML 5% sodium hydroxide solution, 1 min that is vortexed stand 10 min infiltration samples, take 10 mL n-hexanes/methanol solution after mixing
Into above-mentioned tool plug centrifuge tube, and on vortex mixer with the min of 4000 rpm velocity fluctuations 30;
4) purification of extracts:1.5 mL are taken to extract supernatant in the purification containing Dispersive solid phase extraction material in 2 mL
In centrifuge tube, in vibrating 2 min on vortex mixer with 4000 rpm, 1 min is centrifuged with 10000 rpm, takes supernatant mistake
0.45 μm of laggard liquid phase analysis of organic phase filter membrane;
5) series connection chiral column-conjunction phase chromatographic tandem mass spectrography condition:Analytical column 1 is Trefoil CEL1 posts, the mm of column length 150
, the mm of internal diameter 3.0,2.5 μm of stationary phase particle diameter, analytical column 2 is Chiralcel OD-H liquid-phase chromatographic columns, the mm of column length 250,
The mm of internal diameter 4.6,5 μm of stationary phase particle diameter;Mobile phase A is:CO2, Mobile phase B:Methanol containing 0.05% isopropylamine;Flow velocity is
1.0 mL/min;Condition of gradient elution is:0.0 min, 97% A;0.5 min, 97% A;8.0 min, 92% A;12.0 min,
92% A;30.0 min, 90% A;40 DEG C of column temperature;Sample introduction room temperature:10 ℃;The μ L of sampling volume 2;Back pressure:1600 psi;
ISM compensation flow paths are mutually the methanol containing 0.1% formic acid, and flow velocity is 0.3 mL/min;Analysis time amounts to 30 min;Mass spectrum
Condition:Ion gun:Electrospray ionization source, scan mode scan for cation, and ion source temperature is 300 DEG C, and electron spray voltage is 5000
V, atomization gas pressure are 40 psi;Detection mode:Multiple-reaction monitoring(MRM);By peak area being normalized quantitative R-
(+)-nicotine accounts for the ratio of total nicotine, and S- (-)-nornicotine accounts for the ratio of total nornicotine.
2. the chiral analysis of nicotine and nornicotine close phase chromatographic tandem mass spectrography in electronic cigarette liquid according to claim 1,
It is characterized in that:The volume ratio 98 of n-hexane/methanol solution in step 3):2.
3. the chiral analysis of nicotine and nornicotine close phase chromatographic tandem mass spectrography in electronic cigarette liquid according to claim 1,
It is characterized in that:Dispersive solid phase extraction material described in step 4) contains:150 mg anhydrous magnesium sulfates, 50 mg PSA inhale
Attached dose, 25 mg GCB adsorbents.
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