CN106770809B - The analysis method of nicotine chiral isomer in a kind of tobacco juice for electronic smoke - Google Patents
The analysis method of nicotine chiral isomer in a kind of tobacco juice for electronic smoke Download PDFInfo
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Abstract
The present invention provides a kind of analysis method of nicotine chiral isomer in tobacco juice for electronic smoke, specifically includes the following steps: 1) sample pre-treatments；2) preparation of standard solution；3) sample qualitative detection；4) sample amounts detect.The present invention provides a kind of analysis method of nicotine chiral isomer in tobacco juice for electronic smoke, using nicotine as research object, pre-treating method research and liquid phase chromatogram condition optimization are carried out to tobacco juice for electronic smoke, establish the liquid phase chromatography analytical method of nicotine chiral isomer in tobacco juice for electronic smoke, separating degree is good, high sensitivity, it can be achieved that nicotine chiral isomer composition Accurate Determining.
Description
Technical field
The invention belongs to tobacco components analysis field, it is related to a kind of point of nicotine chiral isomer in tobacco juice for electronic smoke
Analysis method.
Background technique
Electronic cigarette, also known as electrospray cigarette are a kind of electronics for transmitting nicotine to respiratory system by electronics heating means
Device, and tobacco juice for electronic smoke is then the electronic fog agent for cooperating electronic cigarette to use.Tobacco juice for electronic smoke mainly includes glycerol, the third two
Alcohol, essence and nicotine etc., wherein nicotine is the major impetus for aspirating electronic cigarette.Nicotine contains a chiral centre, and there are two
Enantiomer: S- (-)-nicotine and R- (+)-nicotine, the two content, metabolic mechanism and physiological property in tobacco is entirely different, day
Nicotine in right tobacco is mainly S- (-)-configuration.
Currently, the chirality research about nicotine in tobacco juice for electronic smoke is less.Zhengzhou tobacco research institute discloses a kind of electronics
The optical activity analysis method (CN 104297409) of nicotine in cigarette tobacco juice realizes nicotine mapping by gas chromatography/mass spectrometry
The preferable separation of body.However when gas-chromatography being used to carry out chiral analysis, to reach preferable separating degree, need to heat up at a slow speed
(0.5 DEG C/min), takes a long time, and separating degree is limited.Due to method sensitivity and S- (-)-nicotine, the separation of R- (+)-nicotine
Spend closely related, this method is only capable of detecting R- (+)-nicotine in 2 samples in 15 tobacco juice for electronic smoke samples, it is more difficult to full
Foot actual needs.
Based on the above status, it is necessary to develop that a kind of separating degree is more preferable, nicotine in the higher tobacco juice for electronic smoke of sensitivity
Chiral analysis method.Currently, having no report of the liquid chromatography for the chiral analysis of nicotine in tobacco juice for electronic smoke.
Summary of the invention
In view of the foregoing deficiencies of prior art, the purpose of the present invention is to provide nicotine hands in a kind of tobacco juice for electronic smoke
Property isomers analysis method, carrying out pre-treating method research and liquid phase chromatogram condition to tobacco juice for electronic smoke optimizes, for solving
Lack in the prior art separating degree is good, high sensitivity, it can be achieved that the Accurate Determining of nicotine chiral isomer composition liquid chromatogram
The problem of analysis method.
In order to achieve the above objects and other related objects, the present invention provides nicotine chiral isomer in a kind of tobacco juice for electronic smoke
Analysis method, specifically includes the following steps:
Preferably, nicotine chiral isomer is S- (-)-nicotine and R- (+)-nicotine in the tobacco juice for electronic smoke.
1) sample pre-treatments: filtering after taking tobacco juice for electronic smoke that organic solvent diluting is added, and obtains prepare liquid；
Preferably, in step 1), the organic solvent be n-hexane and isopropanol mixed solution, the n-hexane with it is different
The ratio between volume that propyl alcohol is added is 6-8:2-4.
It is highly preferred that the ratio between the volume that the n-hexane and isopropanol are added is 7:3.
Preferably, in step 1), the ratio between the volume that the tobacco juice for electronic smoke and organic solvent are added is 1:0-1000.Into one
Preferably, the ratio between the volume that the tobacco juice for electronic smoke and organic solvent are added is 1:10-100 to step.
Preferably, in step 1), the mode of the filtering is membrane filtration mode.It is highly preferred that the filter membrane is organic
Phase filter membrane, aperture are 0.22 μm.
2) preparation of standard solution:
A, the dissolution of nicotine standard product organic solvent and constant volume are taken, Standard Stock solutions are made into；
B, the Standard Stock solutions in different amounts of step A are pipetted respectively, with organic solvent diluting constant volume be it is a series of not
With the standard solution of concentration.
It is highly preferred that in step A, the nicotine standard product are S- (-)-nicotine and R- (+)-nicotine hybrid standard product,
The mass ratio of S- (-)-nicotine and R- (+)-nicotine is 1:1.The nicotine standard product are known as racemic nicotine standard product.
It is highly preferred that in step A and/or B, the organic solvent is the mixed solution of n-hexane and isopropanol, it is described just
The ratio between the volume that hexane and isopropanol are added is 6-8:2-4.
It is further preferred that the ratio between the volume that the n-hexane and isopropanol are added is 7:3.
It is highly preferred that in step B, the concentration range of nicotine chiral isomer ingredient in the standard solution are as follows: S- (-)-
Nicotine is 1-1000 μ g/mL；R- (+)-nicotine is 1-1000 μ g/mL.
It is further preferred that in the standard solution nicotine chiral isomer ingredient concentration range are as follows: S- (-)-nicotine
For 1-500 μ g/mL；R- (+)-nicotine is 1-500 μ g/mL.
3) sample qualitative detection: the prepare liquid and step 2) Plays solution for respectively preparing step 1) carry out liquid chromatogram
(LC) detect, compare retention time carry out it is qualitative, determine nicotine chiral isomer ingredient in prepare liquid；
4) sample amounts detect: the prepare liquid and step 2) Plays solution for respectively preparing step 1) carry out liquid chromatogram
(LC) it detects, is quantified using external standard method, obtain the content of nicotine chiral isomer in prepare liquid.
Preferably, step 3) and/or 4) in, the condition of the liquid chromatogram (LC) detection are as follows:
Chromatographic column: IC chromatographic column；Column temperature: 20-30 DEG C；Flow velocity: 0.5-2.0mL/min；Sample volume: 5-20 μ l；Ultraviolet inspection
Survey wavelength: 255-265nm；Mobile phase: the triethylamine containing 0.05-0.15% n-hexane/isopropyl alcohol mixture (n-hexane with it is different
Propyl alcohol volume ratio is 97-99:1-3)；Analysis time: 40-100min；Isocratic elution.
It is highly preferred that the condition of liquid chromatogram (LC) detection are as follows:
Chromatographic column:IC chromatographic column (4.6mm × 250mm, 5 μm)；Column temperature: 25 DEG C；Flow velocity: 1.0mL/
min；Sample volume: 10 μ l；Ultraviolet detection wavelength: 260nm；Mobile phase: the n-hexane containing 0.1% triethylamine/isopropanol mixing is molten
Liquid (n-hexane is 98:2 with isopropanol volume ratio)；Analysis time: 45min；Isocratic elution.
Preferably, the external standard method refers to: respectively by a series of standard solution of step 2) various concentrations, using LC
Sample introduction is analyzed, respectively obtain standard solution in S- (-)-nicotine, R- (+)-nicotine content and peak area linear relationship, respectively with
S- (-)-nicotine or R- (+)-nicotine chromatographic peak area correspond to its corresponding content, draw corresponding standard working curve, calculate
Obtain the regression equation of above-mentioned each standard working curve.Prepare liquid is detected using LC again, by S- (-)-in the prepare liquid of acquisition
Nicotine, R- (+)-nicotine chromatographic peak area substitute into the regression equation of respective standard working curve respectively, corresponding cigarette can be obtained
The content of alkali chiral isomer ingredient.
As described above, in a kind of tobacco juice for electronic smoke provided by the invention nicotine chiral isomer analysis method, with nicotine
For research object, pre-treating method research is carried out to tobacco juice for electronic smoke and liquid phase chromatogram condition optimizes, establishes tobacco juice for electronic smoke
Middle nicotine chiral isomer ingredient: S- (-)-nicotine and R- (+)-nicotine liquid phase chromatography analytical method.Analysis side in the present invention
Method can fully achieve S- (-)-nicotine and R- (+)-nicotine baseline separation, and the two separating degree improves a lot than existing methods.
In the present invention in analysis method, measurement sample without removing moisture removal, after dilute filtration can direct injected, it is easy to operate.The present invention
(detection limit can fully meet nicotine in tobacco juice for electronic smoke up to 0.3 μ g/mL), reproducible to the high sensitivity of middle analysis method
Chiral isomer composition analysis needs.
Detailed description of the invention
Fig. 1 is shown as racemic nicotine in the present invention (i.e. S- (-)-nicotine and R- (+)-nicotine respectively accounts for 50%) standard sample
Liquid chromatogram.
Fig. 2 is shown as in the present invention S- (-)-nicotine and R- (+)-nicotine liquid chromatogram in tobacco juice for electronic smoke.
Specific embodiment
The present invention is further explained combined with specific embodiments below, it should be appreciated that these embodiments are merely to illustrate the present invention
Rather than it limits the scope of the invention.
Illustrate embodiments of the present invention below by way of specific specific example, those skilled in the art can be by this specification
Other advantages and efficacy of the present invention can be easily understood for disclosed content.The present invention can also pass through in addition different specific realities
The mode of applying is embodied or practiced, the various details in this specification can also based on different viewpoints and application, without departing from
Various modifications or alterations are carried out under spirit of the invention.
The reagent and instrument that following embodiment uses are as follows:
1, reagent
Tobacco juice for electronic smoke (tobacco juice for electronic smoke of commercial goods)；Racemic nicotine standard product (S- (-)-nicotine and R-
(+)-nicotine respectively accounts for 50wt%, Sigma Co., USA)；N-hexane (chromatographically pure, RCI Labscan Limited), isopropyl
Alcohol (chromatographically pure, Tedia company, the U.S.), triethylamine (chromatographically pure, Amethyst Chemicals company).
2, instrument
1260 type liquid chromatogram of Agilent (production of Agilent company, the U.S.) is equipped with UV detector.
Embodiment 1
1, sample pre-treatments
It takes the mixed solution of tobacco juice for electronic smoke addition n-hexane and isopropanol to filter after being diluted, obtains prepare liquid.Its
In, in the mixed solution of n-hexane and isopropanol, the ratio between the volume that n-hexane and isopropanol are added is 7:3.Tobacco juice for electronic smoke with
The ratio between volume that the mixed solution of n-hexane and isopropanol is added is 1:40.
2, the preparation of standard solution
A certain amount of racemic nicotine standard product are weighed, S- (-)-nicotine and R- (+)-nicotine in racemic nicotine standard product
Mass ratio be 1:1, using the mixed solution of n-hexane and isopropanol dissolution and constant volume, be first made into Standard Stock solutions.Again
Different amounts of Standard Stock solutions are pipetted, use the mixed solution of n-hexane and isopropanol dilution constant volume for a series of various concentrations
Standard solution.S- (-)-nicotine concentration range is that 1-500 μ g/mL, R- (+)-nicotine concentration range are in standard solution
1-500μg/mL.Wherein, in the mixed solution of n-hexane and isopropanol, the ratio between the volume that n-hexane and isopropanol are added is 7:3.
3, it measures
The standard solution in the prepare liquid and step 2 prepared in above-mentioned steps 1 is subjected to LC detection respectively, when comparing reservation
Between carry out qualitative, determine nicotine chiral isomer ingredient in prepare liquid: S- (-)-nicotine, R- (+)-nicotine；External standard is used simultaneously
Method is quantified, and nicotine chiral isomer ingredient in prepare liquid: S- (-)-nicotine, R- (+)-nicotine content is obtained.Specific inspection
Survey the result is shown in Figure 1-2.By Fig. 1-2 it is found that method is very good to the separating effect of nicotine chiral isomer in the present invention.
When specific measurement, the external standard method refers to: respectively by a series of standard solution of various concentrations described in step 2, adopting
With LC, sample introduction is analyzed, obtains the linear relationship of S- (-)-nicotine, R- (+)-nicotine content and peak area in standard solution respectively, point
Its corresponding content is not corresponded to S- (-)-nicotine or R- (+)-nicotine chromatographic peak area, draws corresponding standard working curve,
The regression equation of above-mentioned each standard working curve is calculated.Prepare liquid is detected using LC again, by S- in the prepare liquid of acquisition
(-)-nicotine, R- (+)-nicotine chromatographic peak area substitute into the regression equation of respective standard working curve respectively, phase can be obtained
Answer the content of nicotine chiral isomer ingredient.
Wherein, the condition of liquid chromatogram (LC) detection are as follows: chromatographic column:IC chromatographic column (4.6mm
× 250mm, 5 μm)；Column temperature: 25 DEG C；Flow velocity: 1.0mL/min；Sample volume: 10 μ l；Ultraviolet detection wavelength: 260nm；Mobile phase:
N-hexane/isopropyl alcohol mixture containing 0.1% triethylamine (n-hexane is 98:2 with isopropanol volume ratio)；Analysis time:
45min；Isocratic elution.
Embodiment 2
1, sample pre-treatments
It takes the mixed solution of tobacco juice for electronic smoke addition n-hexane and isopropanol to filter after being diluted, obtains prepare liquid.Its
In, in the mixed solution of n-hexane and isopropanol, the ratio between the volume that n-hexane and isopropanol are added is 6-8:2-4.Electronic cigarette
The ratio between the volume that the mixed solution of liquid and n-hexane and isopropanol is added is 1:10-100.
2, the preparation of standard solution
A certain amount of racemic nicotine standard product are weighed, S- (-)-nicotine and R- (+)-nicotine in racemic nicotine standard product
Mass ratio be 1:1, using the mixed solution of n-hexane and isopropanol dissolution and constant volume, be first made into Standard Stock solutions.Again
Different amounts of Standard Stock solutions are pipetted, use the mixed solution of n-hexane and isopropanol dilution constant volume for a series of various concentrations
Standard solution.S- (-)-nicotine concentration range is that 1-1000 μ g/mL, R- (+)-nicotine concentration range are in standard solution
1-1000μg/mL.Wherein, in the mixed solution of n-hexane and isopropanol, the ratio between the volume that n-hexane and isopropanol are added is 6-
8:2-4。
3, it measures
The standard solution in the prepare liquid and step 2 prepared in above-mentioned steps 1 is subjected to LC detection respectively, when comparing reservation
Between carry out qualitative, determine nicotine chiral isomer ingredient in prepare liquid: S- (-)-nicotine, R- (+)-nicotine；External standard is used simultaneously
Method is quantified, and nicotine chiral isomer ingredient in prepare liquid: S- (-)-nicotine, R- (+)-nicotine content is obtained.Specific inspection
Survey the result is shown in Figure 1-2.By Fig. 1-2 it is found that method is very good to the separating effect of nicotine chiral isomer in the present invention.
When specific measurement, the external standard method refers to: respectively by a series of standard solution of various concentrations described in step 2, adopting
With LC, sample introduction is analyzed, obtains the linear relationship of S- (-)-nicotine, R- (+)-nicotine content and peak area in standard solution respectively, point
Its corresponding content is not corresponded to S- (-)-nicotine or R- (+)-nicotine chromatographic peak area, draws corresponding standard working curve,
The regression equation of above-mentioned each standard working curve is calculated.Prepare liquid is detected using LC again, by S- in the prepare liquid of acquisition
(-)-nicotine, R- (+)-nicotine chromatographic peak area substitute into the regression equation of respective standard working curve respectively, phase can be obtained
Answer the content of nicotine chiral isomer ingredient.
Wherein, the condition of liquid chromatogram (LC) detection are as follows: chromatographic column: IC chromatographic column；Column temperature: 20-30 DEG C；Flow velocity:
0.5-2.0mL/min；Sample volume: 5-20 μ l；Ultraviolet detection wavelength: 255-265nm；Mobile phase: triethylamine containing 0.05-0.15%
N-hexane/isopropyl alcohol mixture (n-hexane and isopropanol volume ratio be 97-99:1-3)；Analysis time: 40-100min；
Isocratic elution.
Embodiment 3
The Standard Stock solutions of racemic nicotine standard product shown in the step 2 such as embodiment 1 of different volumes are pipetted respectively,
Constant volume is diluted using the mixed solution (v/v=7:3) of n-hexane and isopropanol, a series of standard for being formulated as various concentrations is molten
Liquid.Wherein, S- (-)-nicotine concentration is respectively 1,2,5,10,20,50,100,200,500 μ g/mL, standard in standard solution
R- (+)-nicotine concentration is respectively 1,2,5,10,20,50,100,200,500 μ g/mL in solution.
A series of standard solution of above-mentioned prepared various concentrations is subjected to LC detection respectively, is vertical with chromatographic peak area
Coordinate (Y-axis), the mass concentration of corresponding nicotine chiral isomer are abscissa (X-axis), carry out regression analysis, obtain recurrence side
Journey and its related coefficient are detection limit with 3 times of signal-to-noise ratio, obtain the detection limit of method, and concrete outcome is as shown in table 1.
As shown in Table 1, regression equation linear relationship is good when sample introduction in 1~500 μ g/mL concentration range, phase relation
Number R2>0.9995.Due to having good separating degree between two enantiomers, the detection of method is limited up to 0.3 μ g/mL, tool
There is higher method sensitivity.
1 methodological study of table: linear, detection limit
Y: peak area；X: concentration
Embodiment 4
Racemic nicotine standard sample is taken to carry out pre-treatment, then the item of the step 3 by embodiment 1 by the step 1 of embodiment 1
Part is measured, and repeatedly Parallel testing 5 times (n=5) respectively, the results are shown in Table 2.As can be seen from Table 2, racemic nicotine standard sample
R- (+)-nicotine relative standard deviation (RSD) is 0.06% in product.And it is analyzed and is stated according to existing nicotine chiral isomer
Mode is accounted for the percentage of total nicotine with R- (+)-nicotine mainly to indicate that nicotine chirality forms, R- (+)-nicotine is removed in total nicotine
It is in addition S- (-)-nicotine.So the precision of measuring method is preferable in the present invention, repeatability is good.
2 methodological study of table: precision (n=5)
*R- (+)-nicotine average quality percentage accounting (relative to total nicotine content)
Embodiment 5
It is formed using the nicotine chirality that this method measures 9 kinds of tobacco juice for electronic smoke samples, replication 3 times (n=3), specifically
It the results are shown in Table 3.As shown in Table 3, average quality hundred of R- (+)-nicotine with respect to total nicotine content in different brands tobacco juice for electronic smoke
Dividing accounting is 0.127-0.716%, and R- (+)-nicotine relative standard deviation (RSD) is 0.9-7.5%.And according to existing cigarette
Alkali chiral isomer analyzes form of presentation, accounts for the percentage of total nicotine with R- (+)-nicotine mainly to indicate that nicotine chirality forms,
It is S- (-)-nicotine in addition to R- (+)-nicotine in total nicotine.To show that this method can be effective for different samples
The content of nicotine chiral isomer ingredient in its actual sample is measured, method is easy to operate, applicability is good, as a result accurately, reliably.
3 tobacco juice for electronic smoke nicotine chiral component of table analyzes (n=3)
*R- (+)-nicotine average quality percentage accounting (relative to total nicotine content)
So the present invention effectively overcomes various shortcoming in the prior art and has high industrial utilization value.
The above-described embodiments merely illustrate the principles and effects of the present invention, and is not intended to limit the present invention.It is any ripe
The personage for knowing this technology all without departing from the spirit and scope of the present invention, carries out modifications and changes to above-described embodiment.Cause
This, institute is complete without departing from the spirit and technical ideas disclosed in the present invention by those of ordinary skill in the art such as
At all equivalent modifications or change, should be covered by the claims of the present invention.
Claims (5)
1. the analysis method of nicotine chiral isomer in a kind of tobacco juice for electronic smoke, specifically includes the following steps:
1) sample pre-treatments: filtering after taking tobacco juice for electronic smoke that organic solvent diluting is added, and obtains prepare liquid；
2) preparation of standard solution: nicotine standard product is taken to be prepared with organic solvent；
3) sample qualitative detection: the prepare liquid and step 2) Plays solution for respectively preparing step 1) carry out liquid chromatogram inspection
Survey, compare retention time carry out it is qualitative, determine nicotine chiral isomer ingredient in prepare liquid；
4) sample amounts detect: the prepare liquid and step 2) Plays solution for respectively preparing step 1) carry out liquid chromatogram inspection
It surveys, is quantified using external standard method, obtain the content of nicotine chiral isomer in prepare liquid；
Step 1) and/or 2) in, the organic solvent is the mixed solution of n-hexane and isopropanol, the n-hexane and isopropanol
The ratio between volume of addition is 7:3；
Step 3) and/or 4) in, the condition of the liquid chromatographic detection are as follows: chromatographic column:IC chromatographic column,
4.6mm × 250mm, 5 μm；Column temperature: 25 DEG C；Flow velocity: 1.0mL/min；Sample volume: 10 μ l；Ultraviolet detection wavelength: 260nm；Flowing
Phase: n-hexane/isopropyl alcohol mixture containing 0.1% triethylamine, wherein n-hexane is 98:2 with isopropanol volume ratio；Analysis
Time: 45min；Isocratic elution；
Nicotine chiral isomer is S- (-)-nicotine and R- (+)-nicotine in the tobacco juice for electronic smoke.
2. the analysis method of nicotine chiral isomer in a kind of tobacco juice for electronic smoke according to claim 1, which is characterized in that
In step 1), the ratio between the volume that the tobacco juice for electronic smoke and organic solvent are added is 1:0-1000.
3. the analysis method of nicotine chiral isomer in a kind of tobacco juice for electronic smoke according to claim 1, which is characterized in that
In step 2), the preparation of the standard solution, comprising the following steps:
A the dissolution of nicotine standard product organic solvent and constant volume) are taken, Standard Stock solutions are made into；
B the Standard Stock solutions in different amounts of step A) are pipetted respectively, are that a series of differences are dense with organic solvent diluting constant volume
The standard solution of degree.
4. the analysis method of nicotine chiral isomer in a kind of tobacco juice for electronic smoke according to claim 3, which is characterized in that
Step B) in, the concentration range of nicotine chiral isomer ingredient in the standard solution are as follows: S- (-)-nicotine is 1-1000 μ g/
mL；R- (+)-nicotine is 1-1000 μ g/mL.
5. the analysis method of nicotine chiral isomer in a kind of tobacco juice for electronic smoke according to claim 1, which is characterized in that
In step 2), the nicotine standard product be S- (-)-nicotine and R- (+)-nicotine hybrid standard product, S- (-)-nicotine with
R- (+)-nicotine mass ratio is 1:1.
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| CN107367555B (en) * | 2017-06-29 | 2019-09-06 | 国家烟草质量监督检验中心 | Nicotine and chiral resolution measuring method while nornicotine in a kind of tobacco juice for electronic smoke |
| CN109619660B (en) * | 2019-02-18 | 2021-09-28 | 湖北和诺生物工程股份有限公司 | Method for extracting R-nicotine from tobacco waste |
| CN111398494B (en) * | 2020-03-19 | 2022-07-12 | 云南中烟工业有限责任公司 | Nicotine optical isomer separation and determination method based on reversed-phase two-dimensional liquid chromatography |
| GB202006008D0 (en) * | 2020-04-24 | 2020-06-10 | Nicoventures Trading Ltd | Aerosolisable formulation |
| CN117388406A (en) * | 2023-11-03 | 2024-01-12 | 东莞市鸿馥生物科技有限公司 | Determination method for chiral resolution of 1-methyl-2 alpha- (6-methyl-3-pyridyl) pyrrolidine |
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| CN104297409A (en) * | 2014-11-05 | 2015-01-21 | 中国烟草总公司郑州烟草研究院 | Chiral analysis method for nicotine in tobacco juice of electronic cigarette |
| CN106324130A (en) * | 2016-08-15 | 2017-01-11 | 国家烟草质量监督检验中心 | Chiral analysis method for nicotine in cigarette cut tobacco |
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