CN118032973A - Method for determining ketone fragrance components in cigarette smoke by GC-MS/MS - Google Patents
Method for determining ketone fragrance components in cigarette smoke by GC-MS/MS Download PDFInfo
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- 235000019504 cigarettes Nutrition 0.000 title claims abstract description 84
- 150000002576 ketones Chemical class 0.000 title claims abstract description 81
- 239000000779 smoke Substances 0.000 title claims abstract description 79
- 238000000034 method Methods 0.000 title claims abstract description 71
- 239000003205 fragrance Substances 0.000 title claims abstract description 29
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 title claims abstract description 29
- 239000000126 substance Substances 0.000 claims abstract description 78
- 238000010521 absorption reaction Methods 0.000 claims abstract description 47
- 239000007788 liquid Substances 0.000 claims abstract description 29
- 238000010438 heat treatment Methods 0.000 claims abstract description 22
- 230000000391 smoking effect Effects 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 15
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003546 flue gas Substances 0.000 claims abstract description 14
- 239000007789 gas Substances 0.000 claims abstract description 10
- 238000004885 tandem mass spectrometry Methods 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
- 241000208125 Nicotiana Species 0.000 claims description 34
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 34
- 238000001514 detection method Methods 0.000 claims description 28
- 239000003365 glass fiber Substances 0.000 claims description 16
- 150000002500 ions Chemical class 0.000 claims description 15
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 14
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- 239000000243 solution Substances 0.000 claims description 14
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- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 238000002485 combustion reaction Methods 0.000 claims description 4
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- LTUMRKDLVGQMJU-IUBLYSDUSA-N farnesyl acetone Chemical class CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(C)=O LTUMRKDLVGQMJU-IUBLYSDUSA-N 0.000 abstract description 26
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- HNZUNIKWNYHEJJ-UHFFFAOYSA-N geranyl acetone Chemical class CC(C)=CCCC(C)=CCCC(C)=O HNZUNIKWNYHEJJ-UHFFFAOYSA-N 0.000 abstract description 13
- HNZUNIKWNYHEJJ-FMIVXFBMSA-N geranyl acetone Chemical class CC(C)=CCC\C(C)=C\CCC(C)=O HNZUNIKWNYHEJJ-FMIVXFBMSA-N 0.000 abstract description 13
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract description 6
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- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 description 8
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- IMQLKJBTEOYOSI-UHFFFAOYSA-N Diphosphoinositol tetrakisphosphate Chemical compound OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 description 2
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- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
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- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Abstract
The application discloses a method for determining ketone fragrance components in cigarette smoke by GC-MS/MS, which comprises the following steps: heating in a tube furnace, absorbing solvent or capturing by a smoking machine, and extracting solvent to obtain a flue gas absorption liquid; the obtained flue gas absorption liquid is detected by adopting a gas chromatography-tandem mass spectrometry method to obtain the ketone fragrance components contained in the flue gas absorption liquid of the sample. The method establishes a method capable of simultaneously and quantitatively measuring 28 ketone aroma substances by combining heating in a tube furnace with solvent absorption and GC-MS/MS, and can effectively distinguish two pairs of isomers of dihydro-beta-ionone and geranylacetone, farnesylacetone and farnesylacetone.
Description
Technical Field
The application relates to the technical field of detection of tobacco ketone substances, in particular to a method for determining ketone fragrance components in cigarette smoke by GC-MS/MS.
Background
The ketone compound is one of important neutral aroma components in cigarette smoke, has obvious influence on the taste of cigarettes, for example, geranylacetone has fresh flower aroma and fruit aroma, and can enhance the fresh and sweet aroma of tobacco products; isophorone has sweet and camphora-like aroma, and after dilution, the isophorone presents the aroma of honey, so that the original aroma and the faint scent flavor of tobacco of the tobacco product can be enhanced; acetophenone has sweet coumarin flavor, bitter aroma, flos crataegi flavor and flavor similar to that of Acacia and Mimosa pudica, and can coordinate with tobacco flavor, enhance smell of hay, and improve smoking quality of tobacco product.
Currently, methods for measuring ketone aroma substances in tobacco mainly include Liquid Chromatography (LC), liquid chromatography-mass spectrometry (LC-MS), liquid chromatography-tandem mass spectrometry (LC-MS/MS), gas Chromatography (GC), gas chromatography-mass spectrometry (GC-MS), and gas chromatography-tandem mass spectrometry (GC-MS/MS).
According to the related study, the tobacco products mainly contain 28 ketone aroma substances, and the structural formula of the ketone aroma substances is shown in figure 1.
In the existing tobacco product detection, although the detection methods are commonly used, for example, CN 201210388375.0 discloses another method for detecting and judging the flavor of flue-cured tobacco, in the method, gas chromatography mass spectrometry (GC-MS) is adopted to quantitatively obtain the flavor-causing substance of flue-cured tobacco, the obtained result contains ketone substances, but the existing method is limited in analyzing the types of tobacco products, the related analysis data of the ketone substances are not comprehensive, and the method cannot realize simultaneous accurate measurement of various ketone substances. The existing comprehensive and accurate analysis for ketone substances in various tobacco products is difficult to develop. In addition, the existing ketone substances are various, so that the existing detection method cannot effectively distinguish two pairs of isomers of dihydro-beta-ionone and geranylacetone, farnesylacetone and farnesylacetone, and the accuracy of quantitative detection results of specific substances is affected.
When aldehyde and ketone substances are detected, the accurate detection result can be obtained through HPLC after derivatization treatment is carried out on a sample by the current standard method, and the derivatization pretreatment process is complicated, so that the detection efficiency is seriously affected.
However, in the prior art, no existing detection and analysis method exists for accurately determining the content of the ketone substances in the tobacco product, so that the development of the related research on the ketone substances in the tobacco product is slow.
The information disclosed in the background section is only for enhancement of understanding of the general background of the invention and should not be taken as an acknowledgement or any form of suggestion that this information forms the prior art already known to a person of ordinary skill in the art.
Disclosure of Invention
Aiming at the technical problems, the application provides a method for determining ketone aroma components in cigarette smoke by GC-MS/MS, which can simultaneously determine 28 ketone aroma components contained in tobacco products and accurately determine two pairs of isomers of dihydro-beta-ionone and geranylacetone, farnesylacetone and farnesylacetone.
The application provides a method for determining ketone fragrance components in cigarette smoke by GC-MS/MS, which comprises the following steps:
Adopting a tube furnace heating-solvent absorption method or a smoking machine trapping-solvent extraction method to prepare a smoke absorption liquid of a cigarette sample to be tested;
the obtained flue gas absorption liquid is detected by adopting a gas chromatography-tandem mass spectrometry method to obtain the ketone fragrance components contained in the flue gas absorption liquid of the sample.
Preferably, gas chromatography-tandem mass spectrometry detection conditions:
The chromatographic column is DB-5MS UI, and the size of the chromatographic column is 30m multiplied by 0.25mm multiplied by 0.25 mu m; the temperature of the sample inlet is 280 ℃;
Heating program: the initial temperature is 60 ℃, after the temperature is kept for 2min, the temperature is increased to 100 ℃ at 5 ℃/min and kept for 5min, then the temperature is increased to 120 ℃ at 2 ℃/min and kept for 1min, then the temperature is increased to 200 ℃ at 5 ℃/min, then the temperature is increased to 220 ℃ at 3 ℃/min and kept for 2min, and finally the temperature is increased to 240 ℃ at 10 ℃/min;
the carrier gas is nitrogen with the purity of 99.999 percent, and the flow rate of the nitrogen is 1.2mL/min;
the quenching gas is helium with the purity of 99.999 percent, and the flow rate of the helium is 2.25mL/min;
The sample injection mode is split sample injection, and the split ratio is 5:1; the sample injection amount is 0.5 mu L;
The scanning mode of the mass spectrum condition is MRM mode.
Preferably, the MRM parameters of 28 ketone fragrances in the mass spectrometry conditions are:
preferably, mass spectrometry conditions: ionization mode is EI; the ionization voltage was 70ev.
Preferably, the ion source temperature for mass spectrometry conditions is 230 ℃; the temperature of the transmission line is 280 ℃; the solvent was delayed for 2min.
Preferably, the tube furnace heating-solvent absorption method is that a reconstituted tobacco sample in a heated cigarette cartridge is placed in a quartz boat, the quartz boat is placed in a tube furnace for heating, and smoke generated by burning the reconstituted tobacco sample is absorbed by an ethanol solution arranged at an air outlet of the tube furnace, and the ethanol solution absorbing the smoke is smoke absorption liquid.
Preferably, the heating program of the tube furnace is that the temperature is increased to 350 ℃ at 10 ℃/min, and the temperature is kept for 20min;
When heating, the air flow rate in the tube furnace is 7.5mL/min; the quartz boat is arranged in the middle of the tube furnace;
the cigarette sample to be treated by the tube furnace heating-organic solvent absorption method is a tobacco combustion section in a cartridge of the heated cigarette sample; the components of the tobacco combustion section are reconstituted tobacco, or tobacco particles, or filiform tobacco.
Preferably, the ethanol solution used in the tube furnace heating-organic solvent absorption method contains an internal standard substance, wherein the concentration of the internal standard substance is 100ng/mL, and the internal standard substance is as follows: naphthalene, phenethyl acetate and n-heptadecane to prepare the flue gas absorption liquid.
Preferably, the method of collecting and extracting solvent by a smoking machine is to suck cigarettes by the smoking machine, collect the total particulate matters of the main stream smoke of the cigarettes on a glass fiber filter, extract the glass fiber filter by a reagent, and obtain smoke absorption liquid;
or the trapping-solvent extraction method of the smoking machine is to trap and heat the main stream smoke of the cigarettes on a glass fiber filter disc through an electronic cigarette smoking machine, and extract the glass fiber filter disc by reagent ultrasonic or vibration to obtain the smoke absorption liquid.
Preferably, when a smoking machine trapping-solvent extraction method is adopted, an ethanol solution used by the Cambridge filter which traps total particulate matters of main stream smoke of cigarettes is extracted to contain internal standard substances, and the concentration of the internal standard substances is 100ng/mL; the internal standard substances used are: naphthalene, phenethyl acetate, and n-heptadecane.
The method comprises the following specific calculation steps: detecting a ketone fragrance ingredient standard solution by adopting a dMRM method, drawing a standard curve, comparing the ratio of the content of an object to be detected in the standard series solution to the internal scalar with the ratio of the peak area of the object to be detected in the chromatogram to the internal standard area to obtain an a value and a b value of a working curve, obtaining a linear regression equation and correlation coefficients of 28 ketone substances, and calculating the content of the ketone substances in the sample solution by the following formula:
Wherein: m i is the content of ketone substance i in cigarette smoke, ng/cigarette; a i is the peak area of substance i; a. b is calculated by a linear regression equation, and the ratio of the content of the object to be detected in the standard series solution to the internal scalar is plotted against the ratio of the peak area of the object to be detected in the chromatogram to the internal standard area to obtain an a value and a b value of the working curve; m s is the content of an internal standard in the sample solution, ng; a s is the internal standard peak area; v is the volume of the sample solution, mL; n is the number of cigarettes smoked for this analysis.
The arithmetic mean of the three replicates was taken as the final test result for the sample to the nearest 0.01 ng/min.
The application has the beneficial effects that:
1) The method for determining the ketone aroma components in the cigarette smoke by the GC-MS/MS provided by the application establishes a method capable of simultaneously and quantitatively determining 28 ketone aroma components by combining tubular furnace heating-solvent absorption or smoking machine trapping-solvent extraction with the GC-MS/MS. The detection limit and the quantitative limit of 28 ketone compounds are respectively 0.65-2.77 ng/mL and 2.18-9.24 ng/mL, the recovery rate is 81.88-119.32%, the daily precision is 0.04-3.51% (n=6), and the daily precision is 0.11-3.36% (n=6), which shows that the accuracy of the detection result of the method on the ketone compounds can meet the quantitative analysis requirement, and two pairs of isomers of dihydro-beta-ionone and geranylacetone and farnesylacetone can be effectively distinguished. Through verification, the method can realize accurate and effective detection and analysis of ketone aroma substances of 27 different-flavor heating cigarette smoke and heating cigarette smoke in different heating stages.
2) The method for determining the ketone fragrance components in the cigarette smoke by using the GC-MS/MS provided by the application does not need to carry out derivatization treatment on carbonyl functional groups in the smoke absorption liquid to be detected, is simple in pretreatment operation, and has lower detection limit for ketone substances in the smoke than the existing method.
Drawings
FIG. 1 shows the structural formula of 28 ketone-type fragrant substances contained in tobacco products;
FIG. 2 is a qualitative ion flow chart of the isomer measured in the examples of the present application;
FIG. 3 is a schematic diagram of a qualitative ion flow chart of 24 ketone aroma substances measured in an embodiment of the application;
FIG. 4 is a total ion flow diagram of ketones in an embodiment of the application; t1: 4-hydroxy-4-methyl-2-pentanone; t2:4-heptanone; t3: 2-furyl methyl ketone; t4: 6-methyl-2-heptanone; 5-methyl-2 (5H) -furanone; t6-methyl-2-cyclopenten-1-one; t7:6-methyl-5-hepten-2-one; t8 is acetophenone; t9, L-glucosone; t10 is isophorone; t11 is tropone; t12 is menthone; t13, oxidizing isophorone; 1, naphthalene; t14 benzofuranone; t15, d-carvone; 2, phenethyl acetate; t16:1-indanone; t17:β -large Ma Shitong; t18, dihydro- β -ionone; t19 geranylacetone; t20:β -ionone; t21:3, 4-dimethoxy acetophenone; t22 is pyridine pyrrolidone; i3, n-heptadecane; t23:9-fluorenone; t24 nocarlone; t25 is planted with ketone; t26 farnesylacetone; t27 farnesyl acetone; t28. nabumetone;
FIG. 5 is a perspective bar graph of the results of measuring the content of ketone flavoring substances in cigarettes with different flavors according to an embodiment of the present application;
Detailed Description
The invention is described in further detail below with reference to the drawings and examples, but is not limited in any way to any changes or modifications made based on the teachings of the invention, which fall within the scope of the invention.
Examples
Materials and instruments used in the examples below were commercially available unless otherwise specified.
1.1 Materials and reagents
Standards such as 4-hydroxy-4-methyl-2-pentanone, 2-furylmethyl ketone, 1-indanone, isophorone oxide, 6-methyl-2-heptanone, 5-methyl-2 (5H) -furanone, nocarpus ketone, d-carvone, pyridine pyrrolidone, dihydro- β -ionone, acetophenone, 3, 4-dimethoxyacetophenone, 9-fluorenone, geranylacetone, isophorone, 6-methyl-5-hepten-2-one, nabumetone, plant ketone, menthone, benzofuranone, 3-methyl-2-cyclopenten-1-one, 4-heptanone, 3-hydroxy-2-butanone, n-heptadecane, naphthalene, phenethyl acetate were all purchased from Shanghai Michelin Biochemical Co., ltd;
Acacia-based acetone is purchased from Shanghai Jiding Biotechnology Co., ltd;
beta-large Ma Shitong was purchased from Shanghai Sitting chemical technology Co., ltd;
Farnesylacetone was purchased from Shanghai Bi to pharmaceutical technologies Co., ltd;
Tropone was purchased from Shanghai Haohong biological medicine technologies Co., ltd;
levoglucosone, beta-ionone was purchased from Shanghai Ala Biochemical technologies Co., ltd;
the 27 heated cigarette products used were provided from a tobacco quality inspection station.
1.2 Instruments and apparatus
KQ-250DE type digital controlled ultrasonic cleaner was purchased from Kunshan ultrasonic instruments Inc.;
BTF-1200C-S tube furnace was purchased from ambebeck equipment technologies inc;
agilent 7890B/7000C gas chromatograph-mass spectrometer (GC-MS/MS) was purchased from Agilent technologies, inc. of Germany.
Example 1 detection of the content of 28 Ketone substances in a heated cigarette Cartridge
1.3 Sample preparation
1.3.1 Preparation of standard solution: weighing ketone standard substances and internal standard substances, taking ethanol as a solvent to prepare mother liquor with the concentration of 10mg/mL, respectively transferring 50 mu L of each ketone compound mother liquor into a 25mL volumetric flask, and using ethanol to fix the volume to prepare mixed standard solution with the concentration of 20 mu g/mL; and respectively transferring 250 mu L of internal standard substance mother solution into a 25mL volumetric flask, fixing the volume by using ethanol, preparing mixed standard solution with the concentration of 100 mu g/mL, and storing 2 kinds of mixed standard solutions and each mother solution in a refrigerator at the temperature of 4 ℃ for later use.
1.3.2 Sample pretreatment: weighing 0.1g of reconstituted tobacco in each sample in a quartz boat, placing the reconstituted tobacco in the middle of a tube furnace, connecting an absorption bottle filled with 40mL of ethanol solution (containing an internal standard substance and having the concentration of 100 ng/mL) at the air outlet of the tube furnace, introducing air into a suction tube of the absorption bottle, controlling the air flow rate to be 7.5mL/min, and setting a heating program: heating to 350 ℃ at 10 ℃/min, and preserving heat for 20min. And (3) introducing the smoke generated by the reconstituted tobacco sample into the ethanol solution of the absorption bottle to prepare the smoke absorption liquid of the sample tobacco product.
1.4 Experimental conditions
Chromatographic conditions of the flue gas absorbing liquid of each sample obtained: chromatographic column: DB-5MS UI (30 m.times.0.25 mm.times.0.25 μm); the temperature of the sample inlet is 280 ℃, and the temperature is raised by the program: the initial temperature is 60 ℃, after the temperature is kept for 2min, the temperature is increased to 100 ℃ at 5 ℃/min and kept for 5min, then the temperature is increased to 120 ℃ at 2 ℃/min and kept for 1min, then the temperature is increased to 200 ℃ at 5 ℃/min, then the temperature is increased to 220 ℃ at 3 ℃/min and kept for 2min, and finally the temperature is increased to 240 ℃ at 10 ℃/min; the carrier gas was nitrogen (99.999%) at a flow rate of 1.2mL/min; quenching gas was helium (99.999%) at a flow rate of 2.25mL/min; the sample injection mode is split sample injection, and the split ratio is 5:1; the sample loading was 0.5. Mu.L.
Mass spectrometry conditions: ionization mode: EI; ionization voltage 70ev; the ion source temperature is 230 ℃; transmission line temperature: 280 ℃; scanning mode: MRM mode; delaying the solvent for 2min; the MRM parameters of the 28 ketone aroma substances and the 3 internal standard substances are shown in Table 1. In the application, MRM parameters comprise: parent ion, child ion, collision energy.
TABLE 1 retention time of the respective ketones and internal standard substances and MRM parameters
2 Results and discussion
2.1 Optimization of experimental conditions
Firstly, preparing a standard solution of ketone substances and internal standard substances with proper concentration (200 ng/mL), carrying out GC-MS/MS detection analysis under a full scanning mode (MS 1 Scan mode), determining retention time of each ketone substance and internal standard substance, and selecting ions with higher abundance and mass number as parent ions under the corresponding retention time; then, the product mode scanning is carried out under the collision energy of 5-60 eV, the sub-ions and the collision energy are optimized, and the multi-reaction monitoring (MRM) parameters of each ketone substance and the internal standard substance are determined, and the results are shown in Table 1.
The dihydro-beta-ionone and the geranylacetone, the farnesylacetone and the farnesylacetone are two pairs of isomers, the property similarity degree of the dihydro-beta-ionone and the geranylacetone is low, the retention time is different from that of the ion pairs, and the separation is easy; farnesyl acetone has high similarity to farnesyl acetone, has close retention time and is indistinguishable by chromatography, so different sub-ions and collision energy are selected to distinguish the farnesyl acetone from the farnesyl acetone. The two pairs of isomerised qualitative ion flow diagrams are shown in figure 2, and the qualitative ion flow diagrams of other ketone fragrances are shown in figure 3.
From the results obtained in fig. 3, it is shown that the method provided by the present application can effectively distinguish and determine isomers of farnesylacetone from farnesylacetone as compared with other methods.
2.2 Total ion flow diagram
According to the parameters in 1.4, an MRM method is established, wherein the retention time of an internal standard substance is divided into 4 sections, namely 2-7.5 min, 7.5-13.5 min, 13.5-34 min and 34-52.66 min respectively, wherein the first two sections share the same internal standard substance naphthalene, the reason is that the substances which come out of a peak before 13.5min are more, the response value of the substances is lower if the substances are divided into one section, and the ethyl phenyl acetate and the n-heptadecane are respectively used as the internal standard substances of the third section and the fourth section. The mixed standard solution of ketone standard substances and internal standard substances of 100ng/mL is prepared, and the mixed standard solution is detected by using an established MRM method, and the total ion flow chromatograph is shown in figure 4. As can be seen from FIG. 4, the method provided by the application can obtain mutually independent characteristic peaks, and can realize effective distinguishing and determination of the 28 ketone substances.
2.3 Standard Curve establishment
28 Ketone compounds are prepared into 10, 20, 40, 60, 80, 100, 200, 300, 400 and 500ng/mL standard solutions containing internal standard substances, wherein the concentration of the internal standard substances is 100ng/mL. And (3) measuring and analyzing by using an established MRM method, drawing a standard curve by taking the relative concentration as an abscissa and the relative response value as an ordinate, continuously injecting 10ng/mL of standard solution containing the internal standard substance for 10 times, and taking the standard deviation of 3 times and 10 times of the detection result as a detection limit and a quantitative limit. The linear equation, linear range, R 2, detection limit, and quantitative limit are shown in Table 2.
TABLE 2 Linear equation for 28 ketones and R 2
As shown in Table 2, the 28 ketone substances have good linear relation, the correlation coefficient R 2 is above 0.995, and the detection limit and the quantitative limit range are respectively 0.65-2.77 ng/mL and 2.18-9.24 ng/mL, so that the quantitative analysis requirement is met.
2.4 Methodological verification
2.4.1 Repeatability verification experiments to investigate the in-day repeatability of the method, the method of 1.4 was used to heat treat heated cigarettes of different tastes to produce smoke and produce smoke absorption liquid, the smoke absorption liquid preparation method being shown in the pretreatment of 1.3.2 samples. After heating, 1mL of flue gas absorption liquid is taken, filtered by using a 0.22 mu m organic filter membrane, continuously injected for 6 times and repeated for 6 days, and the daily and daytime RSD of 28 ketone substances in the obtained flue gas is calculated, and the result is shown in Table 3.
2.4.2 Accuracy verification experiments the accuracy of the method was verified using a labeled recovery experiment. Firstly, measuring the content of ketone compounds in a flue gas absorption liquid, then, based on the detected amount (if the ketone compounds are not detected, the ketone compounds are based on the average content of detected ketone compounds), respectively adding mixed standard solutions of 28 ketone aroma substances into the flue gas absorption liquid, wherein the addition amount of each ketone compound is respectively 50%, 100% and 200%, and calculating the standard adding recovery rate, and the result is shown in Table 3.
TABLE 3 daily and daytime repetition rates and labeled recovery rates of 28 ketones
As shown in Table 3, the daily precision of 28 ketone compounds ranges from 0.04% to 3.51%, the daily precision ranges from 0.11% to 3.36%, and the results prove that the method has good daily and daily precision, meets the requirement of quantitative analysis, and can distinguish isomer dihydro-beta-ionone from geranylacetone, farnesylacetone from farnesylacetone; the recovery rate of 28 ketone aroma substances is 81.88-119.32%, which shows that the method has good precision and can meet the measurement of ketone aroma components in the smoke of the heated cigarettes.
2.5 Actual sample detection
Numbering 27 kinds of heated cigarettes with different tastes, trapping ketone aroma substances in the smoke of the heated cigarettes with different tastes according to the method in 1.4, filtering by using a 0.22 mu m organic filter membrane, and then performing GC-MS/MS measurement to obtain the ketone compound content in the smoke of the 27 kinds of heated cigarettes with different tastes, wherein the ketone aroma substances are shown in tables 4-1-4-3 and figure 5.
TABLE 4-1 Ketone content (ng/cigarette) in cigarette smoke heated by different brands and different tastes
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TABLE 4-2 Ketone content (ng/cigarette) in cigarette smoke heated by different brands and different flavors
TABLE 4-3 content of Ketone Compounds (ng/Zhi) in cigarette smoke heated by different brands and different flavors
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Carbonyl in the ketone compound is a fragrant group with fragrance, so that the carbonyl becomes one of important fragrant components in heating cigarettes.
As can be seen from fig. 5, the total content of ketone compounds in the heated cigarette smoke with different tastes is different, wherein the total content of ketone compounds in the M9 heated cigarette smoke is the highest, which is probably that the added ketone compounds for flavoring are more. As can be seen from fig. 5, the content of part of ketone substances in the smoke of the heated cigarettes with different tastes is greatly different, and the content of 4-heptanone in the smoke of the heated cigarettes with M7 and M27 is obviously higher than that of the other tastes, so that strong fruit fragrance can be provided; the content of dihydro-beta-ionone in M4 and M22 is obviously higher than that of other tastes, and can provide fresh and sweet flower fragrance; the content of the 3, 4-dimethoxy acetophenone in the M3 is higher than that of other tastes, so that sweet woody flower fragrance can be provided; the content of nocardione in M7 is obviously higher than that of other tastes, and can provide very strong fruit fragrance; the content of the d-carvone in M4 and M9 is obviously higher than that of other tastes, so that the dill oil flavor can be provided; the content of beta-Ma Shitong in M9 and M27 is obviously higher than that of other tastes, and the rose fragrance can be provided; isophorone, geranylacetone, beta-ionone and benzofuranone are significantly higher in M9 than other flavors, they can provide honey aroma, fresh floral and fruity aroma, prominent ionone aroma and weak sweet aroma; the content of menthone and isophorone oxide in M7 is the highest, so that fresh mint fragrance and thick nut fragrance can be provided; the content of farnesyl acetone in M4, M5, M9 and M22 is obviously higher than that of other tastes, so that rose fragrance can be provided; the content of acetophenone and tropone in M4 is obviously higher than that of other tastes, and can provide sweet coumarin flavor and sweet aromatic flavor with very sharp points; the content of the farnesyl acetone and the 6-methyl-5-hepten-2-one in the M5 is obviously higher than that of other tastes, and the sweet flue-cured tobacco fragrance and the pleasant fruit fragrance can be provided; the content of the levoglucosenone, the 6-methyl-2-heptanone and the 2-furyl methyl ketone in the M25 is obviously higher than that of other tastes, and can provide a sweet aroma, a cool camphor aroma and a strong nut aroma; the content of the 3-methyl-2-cyclopentene-1-ketone in the M6 is obviously higher than that of other tastes, and the sweet caramel flavor can be provided; the content of the 4-hydroxy-4-methyl-2-pentanone in the M11 is obviously higher than that of other tastes, and can provide light mint aroma; the content of the phytin in the M27 is obviously higher than that of other tastes, and can provide slightly sweet fragrance; 5-methyl-)
The content of the 2 (5H) -furanone in M1, M5 and M6 is obviously higher than that of other tastes, and can provide strong caramel fragrance; the content of the pyridine pyrrolidone in the M10 is obviously higher than that of other tastes, so that the tobacco taste can be enhanced; nabumetone was not detected in the smoke of the 27 flavours of heated cigarettes, probably because the content of nabumetone in the heated cigarettes was too low.
Summary 3
The test establishes a method capable of simultaneously and quantitatively measuring 28 ketone fragrance components in smoke by utilizing tube furnace heating-solvent absorption and GC-MS/MS, and the method can effectively distinguish two pairs of isomers of dihydro-beta-ionone and geranylacetone, farnesylacetone and farnesylacetone. By utilizing the method to detect 27 kinds of heating cigarette smoke with different tastes and ketone aroma substances of the heating cigarette smoke in different heating stages, the result shows that the total content of the ketone substances in the heating cigarette smoke with different tastes is different, and the total content of the ketone compounds in the I9 heating cigarette smoke is highest; 4-heptanone, dihydro-beta-ionone, 3, 4-dimethoxyacetophenone, nocarpus ketone, dextro-carvone, beta-large Ma Shitong, isophorone, geranylacetone, beta-ionone, benzofuranone, menthone, isophorone oxide, farnesylacetone, acetophenone, cycloheptatrienone, farnesylacetone, levoglucosone, 6-methyl-2-heptanone, 2-furyl methyl ketone, 3-methyl-2-cyclopentene-1-ketone, 4-hydroxy-4-methyl-2-pentanone, phytic ketone, 5-methyl-2 (5H) -furanone and pyridine pyrrolidone have large differences in the smoke of different tastes of heated cigarettes.
Example 2 detection of the content of 28 Ketone substances in cigarettes
The difference from example 1 is that: 1.3.2 sample pretreatment method is as follows:
Adopting a smoking machine trapping-solvent extraction method, smoking cigarettes through the smoking machine, trapping total particulate matters of main stream smoke of the cigarettes on a glass fiber filter disc, and extracting the glass fiber filter disc by using a reagent to obtain smoke absorption liquid; the specific pretreatment process is as follows:
And selecting cigarette samples C1 and C2 with balanced temperature and humidity, sucking the cigarettes through a smoking machine, continuously sucking 5 samples (4-20 samples, preferably 5 samples) by one sample, and capturing total particulate matters of main stream smoke of the cigarettes on a glass fiber filter sheet. Putting the glass fiber filter disc with the trapped main stream smoke of the cigarettes into a glass triangular flask, adding 40mL of acetonitrile extractant with the concentration of an internal standard substance of 100ng/mL, oscillating or ultrasonically extracting for 40-60 min, standing for 5min, and filtering by an organic filter membrane until the detection of GC-MS/MS.
Example 3 detection of Ketone content in electronic Firework
The difference from example 1 is that: 1.3.2 sample pretreatment method is as follows:
Adopting a smoking machine trapping-solvent extraction method, smoking and heating cigarettes through an electronic cigarette machine, trapping total particulate matters of main stream smoke of the electronic cigarette on a glass fiber filter disc, and extracting the glass fiber filter disc by using a reagent to obtain smoke absorption liquid; the specific pretreatment process is as follows:
And selecting electronic cigarette samples T1 and T2 with temperature and humidity balance completed, sucking cigarettes through an electronic cigarette smoking machine, continuously sucking 5 samples (4-8 samples are suitable for 5 samples), and sucking 8 samples (4-10 samples are suitable for 8 samples) each. And (5) collecting the total particulate matters of the main stream smoke of the heated cigarettes on the glass fiber filter sheet. And (3) placing the glass fiber filter disc with the trapped main stream smoke of the heated cigarettes into a glass triangular flask, adding 40mL of acetonitrile extractant with the concentration of an internal standard substance of 100ng/mL, carrying out oscillation or ultrasonic extraction for 40-60 min, standing for 5min, and filtering by an organic filter membrane for detection by GC-MS/MS.
Example 4 detection of Ketone content in heated cigarettes
The difference from example 1 is that: 1.3.2 sample pretreatment method is as follows:
3.2 sample pretreatment: weighing 0.1g of tobacco particle samples T3.1 g of heating cigarette cartridges in each sample, putting the samples into a quartz boat, putting the quartz boat into the middle position of a tube furnace, connecting an absorption bottle filled with 40mL of ethanol solution (containing an internal standard substance and having the concentration of 100 ng/mL) at the air outlet of the tube furnace, introducing air into a suction tube of the absorption bottle, controlling the air flow rate to be 7.5mL/min, and setting a heating program: heating to 350 ℃ at 10 ℃/min, and preserving heat for 20min. And (3) introducing the smoke generated by the reconstituted tobacco sample into the ethanol solution of the absorption bottle to prepare the smoke absorption liquid of the sample tobacco product.
Example 5 detection of Ketone content in heated cigarettes
The difference from example 1 is that: 1.3.2 sample pretreatment method is as follows:
3.2 sample pretreatment: weighing cut tobacco leaf samples T4.1 g in heating cigarette cartridges in each sample, putting the cut tobacco leaf samples T4.1 g in a quartz boat, putting the cut tobacco leaf samples in the middle of a tube furnace, connecting an absorption bottle filled with 40mL of ethanol solution (containing an internal standard substance and having the concentration of 100 ng/mL) at an air outlet of the tube furnace, introducing air into a suction tube of the absorption bottle, controlling the air flow rate to be 7.5mL/min, and setting a heating program: heating to 350 ℃ at 10 ℃/min, and preserving heat for 20min. And (3) introducing the smoke generated by the reconstituted tobacco sample into the ethanol solution of the absorption bottle to prepare the smoke absorption liquid of the sample tobacco product.
The results of the tests in examples 2 to 5 are shown in the following table:
table 5 the results of the tests obtained in examples 2 to 5
As can be seen from Table 5, the method provided by the application can accurately detect the aldehyde substance content in the smoke sample obtained after the smoke sample of the cigarette, the smoke sample of the heated cigarette and the reconstituted tobacco in the heated cigarette cartridge are heated and not combusted, and has the advantages of simple pretreatment operation and accurate detection result.
Although the present invention has been described with reference to the foregoing embodiments, it will be apparent to those skilled in the art that modifications may be made to the embodiments described, or equivalents may be substituted for elements thereof, and any modifications, equivalents, improvements and changes may be made without departing from the spirit and principles of the present invention.
Claims (10)
1. The method for determining the ketone aroma components in the cigarette smoke by using the GC-MS/MS is characterized by comprising the following steps of:
Adopting a tube furnace heating-solvent absorption method or a smoking machine trapping-solvent extraction method to prepare a smoke absorption liquid of a cigarette sample to be tested;
the obtained flue gas absorption liquid is detected by adopting a gas chromatography-tandem mass spectrometry method to obtain the ketone fragrance components contained in the flue gas absorption liquid of the sample.
2. The method for determining ketone aroma components in cigarette smoke by GC-MS/MS according to claim 1, wherein the gas chromatography-tandem mass spectrometry detection conditions are as follows: the chromatographic column is DB-5MS UI, and the size of the chromatographic column is 30m X0.25 mm X0.25 μm; the temperature of the sample inlet is 280 ℃;
Heating program: the initial temperature is 60 ℃, after staying at 2 min ℃, the temperature is raised to 100 ℃ at 5 ℃/min and stays at 5min, then the temperature is raised to 120 ℃ at 2 ℃/min and stays at 1 min, then the temperature is raised to 200 ℃ at 5 ℃/min, then the temperature is raised to 220 ℃ at 3 ℃/min and stays at 2 min, and finally the temperature is raised to 240 ℃ at 10 ℃/min;
The carrier gas is nitrogen with the purity of 99.999 percent, and the flow rate of the nitrogen is 1.2 mL/min; the quenching gas is helium with the purity of 99.999 percent, and the flow rate of the helium is 2.25 mL/min; the sample injection mode is split sample injection, and the split ratio is 5:1; the sample injection amount is 0.5 mu L; the scanning mode of the mass spectrum condition is MRM mode.
3. The method for determining ketone aroma components in cigarette smoke by GC-MS/MS according to claim 1, wherein the MRM parameters of 28 ketone aroma components in mass spectrometry conditions are:
4. The method for determining ketone aroma components in cigarette smoke by GC-MS/MS according to claim 1, wherein mass spectrometry conditions: ionization mode is EI; the ionization voltage was 70 ev.
5. The method for determining ketone aroma components in cigarette smoke by GC-MS/MS according to claim 1, wherein the ion source temperature of the mass spectrometry condition is 230 ℃; the temperature of the transmission line is 280 ℃; solvent delay 2 min.
6. The method for determining ketone fragrance components in cigarette smoke by using GC-MS/MS according to claim 1, wherein the tube furnace heating-solvent absorption method is to place a reconstituted tobacco sample in a heated cigarette cartridge in a quartz boat, place the reconstituted tobacco sample in a tube furnace for heating, and absorb smoke generated by burning the reconstituted tobacco sample through an ethanol solution arranged at an air outlet of the tube furnace, wherein the ethanol solution absorbing the smoke is a smoke absorption liquid.
7. The method for determining the ketone aroma components in the cigarette smoke by using the GC-MS/MS according to claim 6, wherein the heating program of the tube furnace is that the temperature is increased to 350 ℃ at 10 ℃/min and the temperature is kept at 20min;
During heating, the air flow rate in the tube furnace is 7.5 mL/min; the quartz boat is arranged in the middle of the tube furnace;
The cigarette sample to be treated by the tube furnace heating-organic solvent absorption method is a tobacco combustion section in a cartridge of the heated cigarette sample; the components of the tobacco combustion section are reconstituted tobacco, or tobacco particles, or filiform tobacco.
8. The method for determining ketone aroma components in cigarette smoke by GC-MS/MS according to claim 6, wherein the ethanol solution used in the tube furnace heating-organic solvent absorption method contains an internal standard substance, the concentration of the internal standard substance is 100 ng/mL, and the internal standard substance is: naphthalene, phenethyl acetate and n-heptadecane to prepare the flue gas absorption liquid.
9. The method for determining ketone fragrance components in cigarette smoke by GC-MS/MS according to claim 1, wherein the method for capturing and extracting solvent by a smoking machine is to suck cigarettes by the smoking machine, capture total particulate matters of main stream smoke of the cigarettes on a glass fiber filter, extract the glass fiber filter with a reagent to obtain smoke absorption liquid;
or the trapping-solvent extraction method of the smoking machine is to trap and heat the main stream smoke of the cigarettes on a glass fiber filter disc through an electronic cigarette smoking machine, and extract the glass fiber filter disc by reagent ultrasonic or vibration to obtain the smoke absorption liquid.
10. The method for determining ketone fragrance components in cigarette smoke by GC-MS/MS according to claim 9, wherein when a smoking machine trapping-solvent extraction method is adopted, an ethanol solution used by Cambridge filter sheets for extracting and trapping total particulate matters of main stream smoke of cigarettes contains internal standard substances, and the concentration of the internal standard substances is 100 ng/mL; the internal standard substances used are: naphthalene, phenethyl acetate, and n-heptadecane.
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