CN114034787A - Method for determining sensory related amide compounds in cigarette mainstream smoke - Google Patents
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- -1 amide compounds Chemical class 0.000 title claims abstract description 80
- 235000019504 cigarettes Nutrition 0.000 title claims abstract description 50
- 239000000779 smoke Substances 0.000 title claims abstract description 46
- 230000001953 sensory effect Effects 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000000605 extraction Methods 0.000 claims abstract description 29
- 239000011347 resin Substances 0.000 claims abstract description 23
- 229920005989 resin Polymers 0.000 claims abstract description 23
- 230000000391 smoking effect Effects 0.000 claims abstract description 21
- 239000002904 solvent Substances 0.000 claims abstract description 19
- 125000005270 trialkylamine group Chemical group 0.000 claims abstract description 14
- 239000000126 substance Substances 0.000 claims abstract description 13
- 238000004885 tandem mass spectrometry Methods 0.000 claims abstract description 13
- 238000004458 analytical method Methods 0.000 claims abstract description 10
- 239000006229 carbon black Substances 0.000 claims abstract description 10
- 238000002156 mixing Methods 0.000 claims abstract description 6
- 238000005086 pumping Methods 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- 239000000243 solution Substances 0.000 claims description 21
- 239000002202 Polyethylene glycol Substances 0.000 claims description 16
- 239000007789 gas Substances 0.000 claims description 16
- 229920001223 polyethylene glycol Polymers 0.000 claims description 16
- 238000001514 detection method Methods 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000003365 glass fiber Substances 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 9
- 239000012086 standard solution Substances 0.000 claims description 8
- 239000012159 carrier gas Substances 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 238000004587 chromatography analysis Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000001819 mass spectrum Methods 0.000 claims description 5
- 238000012544 monitoring process Methods 0.000 claims description 4
- 230000035485 pulse pressure Effects 0.000 claims description 4
- 150000003869 acetamides Chemical class 0.000 claims description 3
- 150000003926 acrylamides Chemical class 0.000 claims description 3
- 229910052786 argon Inorganic materials 0.000 claims description 3
- 230000005540 biological transmission Effects 0.000 claims description 3
- 239000001307 helium Substances 0.000 claims description 3
- 229910052734 helium Inorganic materials 0.000 claims description 3
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 150000005480 nicotinamides Chemical class 0.000 claims description 3
- 230000000630 rising effect Effects 0.000 claims description 3
- 230000005526 G1 to G0 transition Effects 0.000 claims description 2
- QUMITRDILMWWBC-UHFFFAOYSA-N nitroterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C([N+]([O-])=O)=C1 QUMITRDILMWWBC-UHFFFAOYSA-N 0.000 claims description 2
- 238000005070 sampling Methods 0.000 claims description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 2
- 230000006698 induction Effects 0.000 claims 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 18
- 238000011084 recovery Methods 0.000 description 12
- 238000000926 separation method Methods 0.000 description 12
- RLOQBKJCOAXOLR-UHFFFAOYSA-N 1h-pyrrole-2-carboxamide Chemical compound NC(=O)C1=CC=CN1 RLOQBKJCOAXOLR-UHFFFAOYSA-N 0.000 description 10
- MMSZAOIJVLACFN-GORDUTHDSA-N (e)-1-pyrrolidin-1-ylbut-2-en-1-one Chemical compound C\C=C\C(=O)N1CCCC1 MMSZAOIJVLACFN-GORDUTHDSA-N 0.000 description 9
- 241000208125 Nicotiana Species 0.000 description 9
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 9
- 238000001179 sorption measurement Methods 0.000 description 9
- WFSIAHMONQXMJH-UHFFFAOYSA-N 1-pyrrolidin-1-yldecan-1-one Chemical compound CCCCCCCCCC(=O)N1CCCC1 WFSIAHMONQXMJH-UHFFFAOYSA-N 0.000 description 8
- LHCODHVVGGYIOZ-UHFFFAOYSA-N 1-pyrrolidin-1-yltetradecan-1-one Chemical compound CCCCCCCCCCCCCC(=O)N1CCCC1 LHCODHVVGGYIOZ-UHFFFAOYSA-N 0.000 description 8
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 8
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 239000000470 constituent Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- YEJJUJNTWYKFLS-UHFFFAOYSA-N 1-pyrrolidin-1-ylpropan-1-one Chemical compound CCC(=O)N1CCCC1 YEJJUJNTWYKFLS-UHFFFAOYSA-N 0.000 description 6
- FWFUIQDDBOIOMR-UHFFFAOYSA-N 2-methyl-1-pyrrolidin-1-ylpropan-1-one Chemical compound CC(C)C(=O)N1CCCC1 FWFUIQDDBOIOMR-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- RAPTZNFAMIHBTG-UHFFFAOYSA-N 3-methyl-1-pyrrolidin-1-ylbutan-1-one Chemical compound CC(C)CC(=O)N1CCCC1 RAPTZNFAMIHBTG-UHFFFAOYSA-N 0.000 description 5
- ZYVXHFWBYUDDBM-UHFFFAOYSA-N N-methylnicotinamide Chemical compound CNC(=O)C1=CC=CN=C1 ZYVXHFWBYUDDBM-UHFFFAOYSA-N 0.000 description 5
- ZXOAHASJYIUCBG-UHFFFAOYSA-N n-ethylpyridine-3-carboxamide Chemical compound CCNC(=O)C1=CC=CN=C1 ZXOAHASJYIUCBG-UHFFFAOYSA-N 0.000 description 5
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 5
- 229940080818 propionamide Drugs 0.000 description 5
- AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 description 4
- QEAWNPFOQLJDAY-UHFFFAOYSA-N 1-pyrrolidin-1-ylbutan-1-one Chemical compound CCCC(=O)N1CCCC1 QEAWNPFOQLJDAY-UHFFFAOYSA-N 0.000 description 4
- LNWWQYYLZVZXKS-UHFFFAOYSA-N 1-pyrrolidin-1-ylethanone Chemical compound CC(=O)N1CCCC1 LNWWQYYLZVZXKS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000003463 adsorbent Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 229940047889 isobutyramide Drugs 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000011570 nicotinamide Substances 0.000 description 4
- 229960003966 nicotinamide Drugs 0.000 description 4
- 235000005152 nicotinamide Nutrition 0.000 description 4
- 230000035807 sensation Effects 0.000 description 4
- 235000019615 sensations Nutrition 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 3
- SANOUVWGPVYVAV-UHFFFAOYSA-N isovaleramide Chemical compound CC(C)CC(N)=O SANOUVWGPVYVAV-UHFFFAOYSA-N 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000004445 quantitative analysis Methods 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 238000013051 Liquid chromatography–high-resolution mass spectrometry Methods 0.000 description 2
- 239000003546 flue gas Substances 0.000 description 2
- TVFIYRKPCACCNL-UHFFFAOYSA-N furan-2-carboxamide Chemical compound NC(=O)C1=CC=CO1 TVFIYRKPCACCNL-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000002552 multiple reaction monitoring Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000013070 direct material Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- CFNHVUGPXZUTRR-UHFFFAOYSA-N n'-propylethane-1,2-diamine Chemical compound CCCNCCN CFNHVUGPXZUTRR-UHFFFAOYSA-N 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000021317 sensory perception Effects 0.000 description 1
- 230000008786 sensory perception of smell Effects 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 235000019505 tobacco product Nutrition 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
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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
- 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
- G01N30/62—Detectors specially adapted therefor
- G01N30/72—Mass spectrometers
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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
- G01N30/02—Column chromatography
- G01N30/86—Signal analysis
- G01N30/8675—Evaluation, i.e. decoding of the signal into analytical information
- G01N30/8679—Target compound analysis, i.e. whereby a limited number of peaks is analysed
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
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Abstract
The invention relates to a method for determining an sensory related amide compound in cigarette mainstream smoke, and belongs to the technical field of analysis of trace chemical substances in cigarette smoke. The method comprises the following steps: 1) smoking the cigarette by a smoking machine to ensure that the mainstream smoke passes through the filter disc and the XAD-4 resin in sequence; 2) after pumping, mixing the filter disc, the XAD-4 resin, the internal standard substance, trialkylamine and an extraction solvent, and extracting amide compounds in the filter disc and the XAD-4 resin to obtain an extracting solution; 3) the extraction solution is purified by graphitized carbon black, and then the amide compounds in the purified solution are detected and analyzed by gas chromatography-tandem mass spectrometry. The method for determining the sensory related amide compounds in the mainstream smoke of the cigarettes can be used for effectively analyzing various sensory related amide compounds with obvious physicochemical property difference and large content level in the smoke of the cigarettes.
Description
Technical Field
The invention relates to a method for determining an sensory related amide compound in cigarette mainstream smoke, and particularly belongs to the technical field of analysis of trace chemical substances in cigarette smoke.
Background
Cigarette smoke constituents are the most direct material basis for smoker's sensory perception. The chemical constituents in mainstream smoke cause changes in the physiological sensations of the smoker through olfaction, taste and chemical sensations (trigeminal sensations). The amide is a compound in which an acyl group and an amino group are bonded, and the amide may be a derivative of a carboxylic acid, ammonia, or an amine. Literature research shows that (Leffingwell J C, Young H J, Bernasek E. Tobacco scattering for smoking products [ M ], Winston-Salem, North Carolina: 1972; Wangzhong, Zhangdong, Liuhui, etc., sensory-oriented identification of bitter components in smoke and liquid chromatography-high-resolution mass spectrometry [ J ], Mass Spectrometry report, 2016,37(5):414-421), amide compounds are important substances affecting the quality of tobacco and cigarette products. Some amide compounds can cause chemical sensation, some amide compounds can bring bad feelings such as musty, rough, spicy and the like to smokers, such as N-decanoyl pyrrolidine and N-myristoyl pyrrolidine, and some amide compounds have sweet, roasted and the like taste, and can improve sensory comfort, such as 1H-pyrrole-2-formamide and N-isovaleryl pyrrolidine.
Wang Ding Zhong adopts Cambridge filter disc to collect the particulate matter of cigarette smoke in sensory guide identification and liquid chromatography-high resolution mass spectrometry of bitter constituents in smoke, extracts with ethanol, removes ethanol, redissolves with water, removes water to obtain water-soluble constituents, then uses gel chromatography to separate water-soluble constituents, determines bitter characteristic constituents through sensory evaluation, and adopts Q-active type LC-HRMS instrument to identify and quantitatively analyze bitter constituents in cigarette mainstream smoke. The experimental procedure is extremely tedious and time consuming, and only 4 organoleptic related amide compounds (nicotinamide, N-methylnicotinamide, N-ethylnicotinamide, 3-ethyl-4-methyl-3-pyrrol-2-one) can be quantitatively analyzed. Due to the large difference of physicochemical properties (structure, molecular weight, solubility, volatility and the like) of different amide compounds, the content level difference of different amide compounds in cigarette smoke is large, and the interference of complex components in the cigarette smoke is also caused, so that various sensory related amide compounds in the main stream smoke of cigarettes are difficult to be simultaneously and effectively extracted, and the efficient separation and accurate quantitative analysis of the amide compounds are not facilitated.
Disclosure of Invention
The invention aims to provide a method for measuring sensory related amide compounds in cigarette mainstream smoke, which can be used for simultaneously, quickly and effectively extracting various sensory related amide compounds in the cigarette smoke and is beneficial to realizing efficient separation and accurate quantitative analysis of the amide compounds.
The method for determining the sensory related amide compounds in the mainstream smoke of the cigarettes comprises the following steps:
1) smoking the cigarette by a smoking machine to ensure that the mainstream smoke passes through the filter disc and the XAD-4 resin in sequence;
2) after pumping, mixing the filter disc, the XAD-4 resin, the internal standard substance, trialkylamine and an extraction solvent, and extracting amide compounds in the filter disc and the XAD-4 resin to obtain an extracting solution;
3) the extraction solution is purified by graphitized carbon black, and then the amide compounds in the purified solution are detected and analyzed by gas chromatography-tandem mass spectrometry.
According to the method for determining the sensory related amide compounds in the mainstream smoke of the cigarettes, the sample extraction process is simple and convenient, and various sensory related amide compounds with obvious physicochemical property differences can be effectively extracted in a time-saving and labor-saving manner; compared with the traditional solid-phase extraction, the method does not need to use a large amount of organic solvents for elution and concentration operation, and is favorable for improving the accuracy of efficient separation and accurate quantitative analysis of the amide compounds.
The sensory related amide compounds are one or any combination of N-formyl pyrrolidine, acetamide, isobutyramide, propionamide, N-isobutyryl pyrrolidine, N-acetyl pyrrolidine, N-butyryl pyrrolidine, isovaleramide, N-isovaleryl pyrrolidine, N-propionyl pyrrolidine, N-crotonyl pyrrolidine, 3-ethyl-4-methyl-3-pyrrole-2-ketone, furoamide, N-decanoyl pyrrolidine, N-ethyl nicotinamide, N-methyl nicotinamide, 1H-pyrrole-2-formamide, nicotinamide and N-myristoyl pyrrolidine. The organoleptic properties of the individual amides are shown in Table 1.
TABLE 1 organoleptic characteristics of amides
The adopted filter disc is used for trapping particulate matters in the mainstream smoke, and the XAD-4 resin is used for trapping gas-phase components in the mainstream smoke. Wherein the filter disc is connected into the smoking machine by being arranged in the cigarette holder, and the XAD-4 resin is connected into the smoking machine after being arranged in the adsorption tube. When the smoking machine is adopted to smoke cigarettes, the smoking is carried out according to a conventional or deep smoking scheme.
Preferably, the filter is a glass fiber filter. The amount of XAD-4 resin adopted for smoking 4-8 cigarettes is 40-200 mg.
The trialkylamine used in the extraction can assist the extraction solvent to better transfer the amide compounds adsorbed on the XAD-4 resin into the extract. Further, mixing a filter disc for collecting particulate matters in the mainstream smoke when 4-8 cigarettes are smoked, XAD-4 resin, 25-100 mu L of internal standard substance solution and 5-25 mL of trialkylamine extraction solvent solution; the concentration of the trialkylamine extraction solvent solution is 100 to 500 ppm. The extraction solvent solution of trialkylamine is formed by dissolving trialkylamine in an extraction solvent. Further, the concentration of the internal standard substance solution is 50-100 ppm. The internal standard solution is formed by dissolving the internal standard in a solvent consistent with the extraction solvent.
The internal standard substance is one or any combination of deuterated acetamide, deuterated acrylamide and deuterated nicotinamide.
In order to completely extract the sensory related amide compounds from the glass fiber filter sheet and the XAD-4 resin, the extraction solvent is one or any combination of methanol, acetonitrile, acetone and dichloromethane.
Further, the trialkylamine is triethylamine and/or tripropylamine. Wherein, the methanol solution of triethylamine has higher extraction rate for the 19 organoleptic related amide compounds in the table 1. Preferably, the extraction solvent solution of trialkylamine is a methanol solution of triethylamine. Preferably, the extraction is performed by vortexing. In the extraction process, the vortex rotation speed is 2000r/min, and the time is 10 min.
In order to enhance the purification effect and ensure that the sensory related amide compounds do not remain in the graphitized carbon black, the amount of the graphitized carbon black adopted in each 1mL of extracting solution is 20-100 mg. Specifically, the purification comprises the following steps: adding graphitized carbon black into the extracting solution, and carrying out solid-liquid separation after vortex. In the purification process, the rotational speed of the vortex is 2000r/min, and the time is 5 min. The solid-liquid separation is centrifugation.
When gas chromatography-tandem mass spectrometry separation analysis is carried out, a liquid phase obtained by solid-liquid separation is taken, filtered by an organic phase filter membrane and then injected. The pore size of the organic phase filter membrane used was 0.45. mu.m.
In order to ensure that the chromatographic separation of various amide compounds is good, and obtain stronger peak strength and good peak shape, further, the stationary phase of a chromatographic column adopted by chromatographic analysis is polyethylene glycol or polyethylene glycol modified by nitroterephthalic acid. The separation chromatographic column used in the chromatographic analysis is a capillary chromatographic column. The column size was 30 m.times.0.25 mm.times.0.25. mu.m.
In order to reduce the escape of the sensory related amide compounds in the gasification of the sample inlet, the sample inlet mode adopted in the gas chromatography-tandem mass spectrometry separation analysis is pulse non-shunting, and the pulse pressure is 100-300 kPa.
Further, the chromatographic conditions of the detection analysis are as follows: the sample inlet temperature is 200-250 ℃, the sample feeding amount is 1-1.5 mu L, the carrier gas is helium, the constant flow rate is 0.8-1.5 mL/min, the temperature rising program is 40-60 ℃ for 1-3 min, then the temperature is raised to 230-250 ℃ at the rate of 3-8 ℃/min for 10-20 min, and the transmission line temperature is 230-250 ℃; the mass spectrum conditions are as follows: the ionization mode is EI, the scanning mode is a multi-reaction monitoring mode, the solvent delay is 5-10 min, the ion source temperature is 230-300 ℃, the filament emission current is 25-50 muA, the collision gas is argon, and the pressure is 1.0-2.0 mTorr. The detection and analysis in the invention adopts gas chromatography-tandem mass spectrometry multiple reaction monitoring. The detection parameters have the advantages of strong selectivity, high sensitivity and high accuracy. The multi-reaction detection parameters and internal standards of the 19 organoleptic related amide compounds are shown in Table 2.
Table 219 Multi-reaction monitoring parameters and internal standards of organoleptic related amide Compounds
Drawings
FIG. 1 is a schematic representation of the mainstream smoke capture of a cigarette in an embodiment of the invention wherein 1-cigarette, 2-cigarette holder, 3-fiberglass filter, 4-smoking machine connection port, 5-sorbent tube, 6-XAD-4 resin;
FIG. 2 is a chromatogram of 19 amide compounds when a polyethylene glycol capillary chromatographic column is used in Experimental example 3 of the present invention;
FIG. 3 is a chromatogram of 19 amides according to the invention in Experimental example 3 using a capillary column of 6% cyanopropylphenyl-94% dimethylsiloxane;
FIG. 4-a is a chromatogram of acetamide according to Experimental example 3 of the present invention using a polyethylene glycol capillary column;
FIG. 4-b is a chromatogram of acetamide according to Experimental example 3 of the present invention using a capillary column of 6% cyanopropylphenyl-94% dimethylsiloxane;
FIG. 5-a is a chromatogram of N-crotonyl pyrrolidine using a polyethylene glycol capillary column in Experimental example 3 according to the present invention;
FIG. 5-b is a chromatogram of N-crotonylpyrrolidine using a 6% cyanopropylphenyl-94% dimethylsiloxane capillary column in Experimental example 3 of the present invention;
FIG. 6-a is a chromatogram of 3-ethyl-4-methyl-3-pyrrol-2-one using a polyethylene glycol capillary column in Experimental example 3 according to the present invention;
FIG. 6-b is a chromatogram of 3-ethyl-4-methyl-3-pyrrol-2-one using a 6% cyanopropylphenyl-94% dimethylsiloxane capillary column in Experimental example 3 of the present invention;
FIG. 7-a is a furfurylamide chromatogram of Experimental example 3 using a polyethylene glycol capillary chromatography column in accordance with the present invention;
FIG. 7-b is a chromatogram of furfurylamide using a 6% cyanopropylphenyl-94% dimethylsiloxane capillary column in Experimental example 3 of the present invention;
FIG. 8-a is a chromatogram of 1H-pyrrole-2-carboxamide using a polyethylene glycol capillary chromatography column in Experimental example 3 of the present invention;
FIG. 8-b is a chromatogram of 1H-pyrrole-2-carboxamide from Experimental example 3 using a 6% cyanopropylphenyl-94% dimethylsiloxane capillary column;
FIG. 9 is a chromatogram of an internal standard compound when a polyethylene glycol capillary chromatographic column is used in the present invention.
Detailed Description
The present invention will be further described with reference to the following examples.
Examples
The method for determining the sensory related amide compounds in the mainstream smoke of the cigarette comprises the following steps:
(1) selecting a certain flue-cured tobacco sample, and respectively connecting a cigarette holder containing a glass fiber filter disc and an XAD-4 resin (120mg) adsorption tube into a smoking machine pipeline, wherein the smoking condition of the cigarette refers to GB/T16450-2004, and the smoking number of the cigarette is 8; before the collection is started, the glass fiber filter disc is placed into a cigarette holder, a smoking machine is connected, XAD-40 resin is placed into an adsorption pipe, then the adsorption pipe is connected with the cigarette holder through a connection end of the smoking machine, and then the cigarette is connected into the smoking machine, as shown in figure 1, when a cigarette 1 is smoked, mainstream smoke sequentially passes through the glass fiber filter disc 3 in the cigarette holder 2, the connection end 4 of the smoking machine and XAD-4 resin 6 in the adsorption pipe 5.
(2) After the cigarette is smoked, the glass fiber filter disc and the adsorbent in the adsorption tube are quickly transferred to a 15mL centrifuge tube, 25 muL of an internal standard solution with the concentration of 100ppm (the internal standard solution is deuterated acetamide, deuterated acrylamide and deuterated nicotinamide) is added, 10mL of a methanol solution of triethylamine with the concentration of 200ppm is added, and the mixture is vortexed at the speed of 2000r/min for 10 min.
(3) 1mL of the extract was transferred to a 2mL centrifuge tube, 50mg of graphitized carbon black was added, and vortexed at 2000r/min for 5 min. Centrifuging at 8000r/min for 3min, collecting supernatant, filtering with 0.45 μm organic phase filter membrane, and separating and analyzing by gas chromatography-tandem mass spectrometry.
The detection conditions of the gas chromatography-tandem mass spectrometry are as follows:
chromatographic conditions are as follows: the chromatographic column is polyethylene glycol capillary chromatographic column (model DB-FFAP, 30 mm × 0.25 μm); the sample introduction mode is pulse non-shunt, and the pulse pressure is 200 kPa; the temperature of a sample inlet is 240 ℃; the sample injection amount is 1 mu L; the carrier gas is helium, and the constant flow rate is 1 mL/min; temperature rising procedure: keeping the temperature at 50 ℃ for 1min, then heating to 235 ℃ at the speed of 5 ℃/min, and keeping the temperature for 15 min; the transmission line temperature was 230 ℃.
Mass spectrum conditions: the ionization mode is EI; the scanning mode is a multi-reaction monitoring mode; solvent delay of 7 min; the ion source temperature is 280 ℃; the filament emission current is 50 muA; the collision gas was argon and the pressure was 1.0 mTorr.
The multiple reaction monitoring parameters of the 19 amide compounds are shown in Table 2, and the standard curve of each amide compound is shown in Table 3.
TABLE 3 standard curve of amides
| Amide compounds | Linear equation of equations | Correlation coefficient |
| N-formyl-pyrrolidines | Y＝-0.0557+0.0054*X | 0.9996 |
| Acetamide | Y＝0.0138+0.0031*X | 0.9999 |
| Isobutyramide | Y＝-0.0200+0.0017*X | 0.9998 |
| Propionamide | Y＝-0.0060+0.0015*X | 0.9994 |
| N-isobutyrylpyrrolidine | Y＝-0.0032+0.0099*X | 0.9993 |
| N-acetylpyrrolidine | Y＝-0.0322+0.0068*X | 0.9992 |
| N-butyrylpyrrolidine | Y＝0.0153+0.0052*X | 0.9996 |
| Isovaleramide | Y＝-0.0159+0.0022*X | 0.9998 |
| N-Isovalerylpyrrolidine | Y＝-0.0020+0.0057*X | 0.9994 |
| N-propionyl-pyrrolidines | Y＝0.0201+0.0067*X | 0.9996 |
| N-crotonoylpyrrolidine | Y＝0.0852+0.0086*X | 0.9999 |
| 3-ethyl-4-methyl-3-pyrrol-2-one | Y＝0.0154+0.0062*X | 0.9993 |
| Furoamides | Y＝-0.3678+0.0501*X | 0.9991 |
| N-decanoyl-pyrrolidine | Y＝0.0029+0.0017*X | 0.9997 |
| N-ethyl nicotinamide | Y＝0.0088+0.0080*X | 0.9992 |
| N-methylnicotinamide | Y＝-0.0537+0.0050*X | 0.9998 |
| 1H-pyrrole-2-carboxamides | Y＝-0.0667+0.0120*X | 0.9998 |
| Nicotinamide | Y＝-0.0699+0.0089*X | 0.9998 |
| N-myristoyl pyrrolidine | Y＝0.0044+0.0079*X | 0.9994 |
The detection results of the 19 amide compounds in the flue-cured tobacco sample are as follows: 198.9ng/cig of N-formylpyrrolidine, 2245.1ng/cig of acetamide, 65.7ng/cig of isobutyramide, 754.7ng/cig of propionamide, no detection of N-isobutyrylpyrrolidine, 259.1ng/cig of N-acetylpyrrolidine, 6.0ng/cig of N-butyrylpyrrolidine, 551.3ng/cig of isovalerylpyrrolidine, 7.7ng/cig of N-propionylpyrrolidine, 1.9ng/cig of N-crotonoylpyrrolidine, 3-ethyl-4-methyl-3-pyrrol-2-one, 1610.9ng/cig of furoamide, 175.9ng/cig of N-decanoylpyrrolidine, 1.6ng/cig of N-ethylnicotinamide, 334.3ng/cig of N-methylnicotinamide, 1H-pyrrole-2-carboxamide, 947.1ng/cig of formamide, 947.1ng/cig of propionamide, and the like, Nicotinamide 489.5ng/cig and N-myristoyl pyrrolidine were not detected.
According to the detection result of the flue-cured tobacco sample, the content range of the 19 amide compounds is 1.6-2245.1 ng/cig, and the content level difference of different amide compounds in the smoke of the cigarette is large and covers 4 orders of magnitude.
Experimental example 1
The flue-cured tobacco samples in the examples were used for experiments, wherein 15 amide compounds were detected, and a certain amount of undetected compounds (N-propionyl pyrrolidine, N-isobutyryl pyrrolidine, N-decanoyl pyrrolidine, N-myristoyl pyrrolidine) were added to the XAD-4 resin in the glass fiber filter and the adsorption tube after the flue gas was trapped, to study the influence of trialkylamine on the extraction effect.
The amide-based compounds in the glass fiber filter and the adsorption tube were extracted with methanol and a methanol solution containing 200ppm triethylamine under the same conditions as in the example, and the extraction results are shown in Table 3. As can be seen from Table 4, the extraction rate of the methanol to the 19 amide compounds is 0.72-1.00, the extraction rate of triethylamine/methanol is 0.98-1.00, and the extraction rate is obviously improved after the triethylamine is added into the methanol.
TABLE 4 Effect of different extraction solvents on the extraction results
Experimental example 2
The flue-cured tobacco samples in the examples were used for the experiments. 15 amide compounds are detected in the flue-cured tobacco sample, and a certain amount of undetected compounds (N-propionyl pyrrolidine, N-isobutyryl pyrrolidine, N-decanoyl pyrrolidine and N-myristoyl pyrrolidine) are added to XAD-4 resin in a glass fiber filter and an adsorption tube after smoke collection.
The flue gas substrate is purified by respectively using N-propyl ethylenediamine (PSA) adsorbent, C18 adsorbent and Graphitized Carbon Black (GCB), and other conditions are the same as the embodiment. The results of recovery after matrix purification are shown in Table 5. PSA has certain purification effect on the smoke substrate, the recovery rate range of the 19 amide compounds is 0.77-0.98, and the recovery rate is low. C18 has poor purification effect on the smoke matrix, the recovery rate range is 0.83-1.00, and the recovery rate is low. The graphitized carbon black has good purification effect, the recovery rate range is 0.97-1.00, and the recovery rate is good.
TABLE 5 Effect of different adsorbents on the purification effectiveness
Experimental example 3
Preparing a mixed standard solution of 19 amide compounds with the concentration of 10ppm, and performing gas chromatography-tandem mass spectrometry. 19 amide compounds are respectively separated by adopting a capillary chromatographic column (model DB-624, 60m multiplied by 0.25mm multiplied by 1.4 mu m) with a fixed phase of 6% cyanopropylphenyl-94% dimethyl siloxane and a capillary chromatographic column (model DB-FFAP, 30m multiplied by 0.25mm multiplied by 0.25 mu m) with a fixed phase of polyethylene glycol, the mass spectrum scanning mode is full scanning, and other gas chromatography-tandem mass spectrum separation and analysis conditions are the same as the embodiment.
6% cyanopropylphenyl-94% dimethyl siloxane capillary chromatographic column is adopted, and the full scan chromatogram of 19 amide compounds is shown in figure 3. As is clear from FIG. 3, N-decanoylpyrrolidine and N-myristoylpyrrolidine showed no peak, and 5 compounds of acetamide, N-crotonylpyrrolidine, 3-ethyl-4-methyl-3-pyrrol-2-one, furoamide and 1H-pyrrole-2-carboxamide showed no tailing of the chromatographic peak and low peak intensity. Chromatograms of acetamide, N-crotonoylpyrrolidine, 3-ethyl-4-methyl-3-pyrrol-2-one, furoamide, 1H-pyrrole-2-carboxamide are shown in FIG. 4-b, FIG. 5-b, FIG. 6-b, FIG. 7-b, FIG. 8-b, using a 6% cyanopropylphenyl-94% dimethylsiloxane capillary chromatography column.
A polyethylene glycol capillary chromatographic column is adopted, and a full scanning chromatogram of 19 amide compounds is shown in figure 2. From FIG. 2, it can be seen that the chromatogram of each amide-based compound has symmetrical peak shape, high peak intensity and no tailing. By adopting the chromatographic column, 19 amide compounds can be well separated by a thin liquid film with the length of 30m and the diameter of 0.25 mu m, and the cost is lower. When polyethylene glycol capillary chromatographic column is adopted, chromatogram of acetamide, N-crotonyl pyrrolidine, 3-ethyl-4-methyl-3-pyrrole-2-ketone, furoamide and 1H-pyrrole-2-formamide are shown in figure 4-a, figure 5-a, figure 6-a, figure 7-a and figure 8-a. The chromatogram of the internal standard compound when using a polyethylene glycol capillary chromatographic column is shown in FIG. 9.
Experimental example 4
Preparing a mixed standard solution of 19 amide compounds with the concentration of 0.1ppm, and performing gas chromatography-tandem mass spectrometry. The sample injection modes are respectively set as a split ratio of 10:1 (namely the ratio of the carrier gas flow rate of the split outlet to the carrier gas flow rate of the chromatographic column is 10:1), a split ratio of 5:1 (namely the ratio of the carrier gas flow rate of the split outlet to the carrier gas flow rate of the chromatographic column is 5:1), no split (an electromagnetic valve for closing the split outlet during sample injection), pulse no split (an electromagnetic valve for closing the split outlet during sample injection and applying pulse pressure at the sample injection port), and other gas chromatography-tandem mass spectrometry separation analysis conditions are the same as the embodiment. The chromatographic peak area of the amide compound under the condition of the split ratio of 10:1 is set as 1, the chromatographic peak responses of the compounds under different sample injection modes are compared, and the comparison result is shown in table 6. When the split ratio is 10:1, the chromatographic peak response of each amide compound is lowest; when the sampling mode is pulse non-shunting, the chromatographic peak response is improved by 4.2-10.6 times, and the detection sensitivity is obviously improved.
TABLE 60.1 ppm Standard solution chromatogram Peak area under different sample introduction modes and fold increase
Experimental example 5
Preparing 19 mixed standard solutions of the amide compounds, performing gas chromatography-tandem mass spectrometry separation and analysis, and calculating the detection limit by using a signal-to-noise ratio of 3 times. The tobacco leaf samples in the examples were used to perform the standard recovery test, which was performed 3 times in parallel, and the standard recovery was calculated, the test data being shown in table 7.
Table 719 sensory related amide compounds detection limit and recovery
| Amide compounds | Detection limit ng/mL | The recovery rate is high |
| N-formyl-pyrrolidines | 10.3 | 105.4 |
| Acetamide | 9.1 | 106.3 |
| Isobutyramide | 32.8 | 90.7 |
| Propionamide | 26.2 | 102.1 |
| N-isobutyrylpyrrolidine | 4.8 | 93.5 |
| N-acetylpyrrolidine | 9.1 | 94.7 |
| N-butyrylpyrrolidine | 9.1 | 103.8 |
| Isovaleramide | 33.2 | 94.6 |
| N-Isovalerylpyrrolidine | 8.8 | 93.4 |
| N-propionyl-pyrrolidines | 6.9 | 91.8 |
| N-crotonoylpyrrolidine | 4.3 | 107.2 |
| 3-ethyl-4-methyl-3-pyrrol-2-one | 8.4 | 95.5 |
| Furoamides | 2.3 | 98.5 |
| N-decanoyl-pyrrolidine | 16.2 | 102.6 |
| N-ethyl nicotinamide | 3.2 | 93.3 |
| N-methylnicotinamide | 6.6 | 97.2 |
| 1H-pyrrole-2-carboxamides | 2.9 | 105.4 |
| Nicotinamide | 4.1 | 109.4 |
| N-myristoyl pyrrolidine | 3.3 | 103.4 |
As can be seen from the data in Table 7, the detection limit range of the 19 sensory related amide compounds is 2.3-33.2 ng/mL, the recovery rate range is 90.7% -109.4%, and the method for determining the sensory related amide compounds in the tobacco and the tobacco products has the advantages of high sensitivity and high accuracy.
Claims (10)
1. A method for measuring an inductance-related amide compound in mainstream smoke of a cigarette is characterized by comprising the following steps:
1) smoking the cigarette by a smoking machine to ensure that the mainstream smoke passes through the filter disc and the XAD-4 resin in sequence;
2) after pumping, mixing the filter disc, the XAD-4 resin, the internal standard substance, trialkylamine and an extraction solvent, and extracting amide compounds in the filter disc and the XAD-4 resin to obtain an extracting solution;
3) the extraction solution is purified by graphitized carbon black, and then the amide compounds in the purified solution are detected and analyzed by gas chromatography-tandem mass spectrometry.
2. The method for determining the sensory correlation amide-type compounds in the mainstream smoke of the cigarettes according to claim 1, wherein the filter disc is a glass fiber filter disc; the amount of XAD-4 resin adopted for smoking 4-8 cigarettes is 40-200 mg.
3. The method for determining the sensory related amide compounds in the mainstream smoke of the cigarettes according to claim 2, wherein the mixing is performed by mixing a filter disc for trapping particulate matters in the mainstream smoke when 4-8 cigarettes are smoked, XAD-4 resin, 25-100 μ L of an internal standard solution and 5-25 mL of an extraction solvent solution of trialkylamine; the concentration of the trialkylamine extraction solvent solution is 100 to 500 ppm.
4. The method for determining the sensory related amide compounds in the mainstream smoke of the cigarettes according to claim 1, wherein the internal standard substance is one or any combination of deuterated acetamide, deuterated acrylamide and deuterated nicotinamide.
5. The method for determining the induction-related amide compounds in the mainstream smoke of the cigarettes according to claim 1, wherein the extraction solvent is one or any combination of methanol, acetonitrile, acetone and dichloromethane.
6. The method for determining the sensory-related amide-based compound in the mainstream smoke of cigarettes according to claim 1 or 5, wherein the trialkylamine is triethylamine and/or tripropylamine.
7. The method for determining the sensory correlation amide compounds in the mainstream smoke of the cigarettes according to claim 1, wherein the amount of the graphitized carbon black adopted in each 1mL of extracting solution is 20-100 mg.
8. The method for determining the sensory correlation amide compounds in the mainstream smoke of the cigarettes according to claim 1, wherein the stationary phase of a chromatographic column adopted in chromatographic analysis is polyethylene glycol or polyethylene glycol modified by nitroterephthalic acid.
9. The method for determining the sensory related amide compounds in the mainstream smoke of the cigarettes according to claim 8, wherein the sampling mode adopted in the gas chromatography-tandem mass spectrometry is pulse non-shunting, and the pulse pressure is 100-300 kPa.
10. The method for determining the sensory related amide compounds in the mainstream smoke of the cigarette according to claim 1, 8 or 9, wherein the chromatographic conditions of the detection analysis are as follows: the sample inlet temperature is 200-250 ℃, the sample feeding amount is 1-1.5 mu L, the carrier gas is helium, the constant flow rate is 0.8-1.5 mL/min, the temperature rising program is 40-60 ℃ for 1-3 min, then the temperature is raised to 230-250 ℃ at the rate of 3-8 ℃/min for 10-20 min, and the transmission line temperature is 230-250 ℃;
the mass spectrum conditions are as follows: the ionization mode is EI, the scanning mode is a multi-reaction monitoring mode, the solvent delay is 5-10 min, the ion source temperature is 230-300 ℃, the filament emission current is 25-50 muA, the collision gas is argon, and the pressure is 1.0-2.0 mTorr.
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