CN114034787B - Method for measuring sensory related amide compounds in main stream smoke of cigarettes - Google Patents
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- CN114034787B CN114034787B CN202111272227.8A CN202111272227A CN114034787B CN 114034787 B CN114034787 B CN 114034787B CN 202111272227 A CN202111272227 A CN 202111272227A CN 114034787 B CN114034787 B CN 114034787B
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- -1 amide compounds Chemical class 0.000 title claims abstract description 82
- 235000019504 cigarettes Nutrition 0.000 title claims abstract description 45
- 239000000779 smoke Substances 0.000 title claims abstract description 42
- 230000001953 sensory effect Effects 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000000605 extraction Methods 0.000 claims abstract description 28
- 239000011347 resin Substances 0.000 claims abstract description 23
- 229920005989 resin Polymers 0.000 claims abstract description 23
- 239000002904 solvent Substances 0.000 claims abstract description 19
- 230000000391 smoking effect Effects 0.000 claims abstract description 17
- 238000004458 analytical method Methods 0.000 claims abstract description 14
- 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
- 239000006229 carbon black Substances 0.000 claims abstract description 10
- 238000002156 mixing Methods 0.000 claims abstract description 6
- 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
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 18
- 239000007789 gas Substances 0.000 claims description 17
- 239000002202 Polyethylene glycol Substances 0.000 claims description 15
- 229920001223 polyethylene glycol Polymers 0.000 claims description 15
- 238000000926 separation method Methods 0.000 claims description 15
- 238000001514 detection method Methods 0.000 claims description 14
- 238000002347 injection Methods 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- RLOQBKJCOAXOLR-UHFFFAOYSA-N 1h-pyrrole-2-carboxamide Chemical compound NC(=O)C1=CC=CN1 RLOQBKJCOAXOLR-UHFFFAOYSA-N 0.000 claims description 11
- 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 claims description 10
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 10
- 239000003365 glass fiber Substances 0.000 claims description 10
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims description 10
- WFSIAHMONQXMJH-UHFFFAOYSA-N 1-pyrrolidin-1-yldecan-1-one Chemical compound CCCCCCCCCC(=O)N1CCCC1 WFSIAHMONQXMJH-UHFFFAOYSA-N 0.000 claims description 9
- LHCODHVVGGYIOZ-UHFFFAOYSA-N 1-pyrrolidin-1-yltetradecan-1-one Chemical compound CCCCCCCCCCCCCC(=O)N1CCCC1 LHCODHVVGGYIOZ-UHFFFAOYSA-N 0.000 claims description 9
- TVFIYRKPCACCNL-UHFFFAOYSA-N furan-2-carboxamide Chemical compound NC(=O)C1=CC=CO1 TVFIYRKPCACCNL-UHFFFAOYSA-N 0.000 claims description 8
- 239000012086 standard solution Substances 0.000 claims description 8
- YEJJUJNTWYKFLS-UHFFFAOYSA-N 1-pyrrolidin-1-ylpropan-1-one Chemical compound CCC(=O)N1CCCC1 YEJJUJNTWYKFLS-UHFFFAOYSA-N 0.000 claims description 7
- FWFUIQDDBOIOMR-UHFFFAOYSA-N 2-methyl-1-pyrrolidin-1-ylpropan-1-one Chemical compound CC(C)C(=O)N1CCCC1 FWFUIQDDBOIOMR-UHFFFAOYSA-N 0.000 claims description 7
- 239000012159 carrier gas Substances 0.000 claims description 7
- RAPTZNFAMIHBTG-UHFFFAOYSA-N 3-methyl-1-pyrrolidin-1-ylbutan-1-one Chemical compound CC(C)CC(=O)N1CCCC1 RAPTZNFAMIHBTG-UHFFFAOYSA-N 0.000 claims description 6
- 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
- ZYVXHFWBYUDDBM-UHFFFAOYSA-N N-methylnicotinamide Chemical compound CNC(=O)C1=CC=CN=C1 ZYVXHFWBYUDDBM-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 238000012544 monitoring process Methods 0.000 claims description 6
- ZXOAHASJYIUCBG-UHFFFAOYSA-N n-ethylpyridine-3-carboxamide Chemical compound CCNC(=O)C1=CC=CN=C1 ZXOAHASJYIUCBG-UHFFFAOYSA-N 0.000 claims description 6
- AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 claims description 5
- QEAWNPFOQLJDAY-UHFFFAOYSA-N 1-pyrrolidin-1-ylbutan-1-one Chemical compound CCCC(=O)N1CCCC1 QEAWNPFOQLJDAY-UHFFFAOYSA-N 0.000 claims description 5
- LNWWQYYLZVZXKS-UHFFFAOYSA-N 1-pyrrolidin-1-ylethanone Chemical compound CC(=O)N1CCCC1 LNWWQYYLZVZXKS-UHFFFAOYSA-N 0.000 claims description 5
- 229940047889 isobutyramide Drugs 0.000 claims description 5
- SANOUVWGPVYVAV-UHFFFAOYSA-N isovaleramide Chemical compound CC(C)CC(N)=O SANOUVWGPVYVAV-UHFFFAOYSA-N 0.000 claims description 5
- 239000011570 nicotinamide Substances 0.000 claims description 5
- 229960003966 nicotinamide Drugs 0.000 claims description 5
- 235000005152 nicotinamide Nutrition 0.000 claims description 5
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 5
- 229940080818 propionamide Drugs 0.000 claims description 5
- 230000035485 pulse pressure Effects 0.000 claims description 4
- 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
- 238000001819 mass spectrum Methods 0.000 claims description 3
- 150000005480 nicotinamides Chemical class 0.000 claims description 3
- 238000002414 normal-phase solid-phase extraction Methods 0.000 claims description 3
- 150000003869 acetamides Chemical class 0.000 claims description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 description 13
- 238000011084 recovery Methods 0.000 description 12
- 241000208125 Nicotiana Species 0.000 description 9
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 9
- 238000001179 sorption measurement Methods 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000000746 purification Methods 0.000 description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 5
- 239000003546 flue gas Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000003463 adsorbent Substances 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 230000035807 sensation Effects 0.000 description 4
- 235000019615 sensations Nutrition 0.000 description 4
- 230000005526 G1 to G0 transition Effects 0.000 description 3
- 235000019658 bitter taste Nutrition 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000004445 quantitative analysis Methods 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
- 238000013051 Liquid chromatography–high-resolution mass spectrometry Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YOLVBJUSDXESQT-LSLKUGRBSA-N (2S)-2-amino-N-(1-diphenoxyphosphorylethyl)propanamide Chemical compound C=1C=CC=CC=1OP(=O)(C(C)NC(=O)[C@@H](N)C)OC1=CC=CC=C1 YOLVBJUSDXESQT-LSLKUGRBSA-N 0.000 description 1
- 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000013070 direct material Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000002546 full scan 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
- 230000006872 improvement Effects 0.000 description 1
- 239000007791 liquid phase Substances 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
- 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 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 235000019633 pungent taste Nutrition 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000021317 sensory perception Effects 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 235000019505 tobacco product Nutrition 0.000 description 1
- 210000003901 trigeminal nerve Anatomy 0.000 description 1
- 238000003260 vortexing Methods 0.000 description 1
Classifications
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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
-
- 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
-
- 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
-
- 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
- G01N30/86—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
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
- G01N2030/065—Preparation using different phases to separate parts of sample
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/20—Air quality improvement or preservation, e.g. vehicle emission control or emission reduction by using catalytic converters
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- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
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- Pathology (AREA)
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Abstract
The invention relates to a method for measuring sensory related amide compounds 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) A smoking machine is adopted to smoke cigarettes, so that main stream smoke sequentially passes through a filter disc and XAD-4 resin; 2) Mixing the filter disc, XAD-4 resin, an internal standard substance, trialkylamine and an extraction solvent after the suction is finished, and extracting amide compounds in the filter disc and the XAD-4 resin to obtain an extract; 3) Purifying the extracting solution by graphitized carbon black, and detecting and analyzing the amide compounds in the purified solution by gas chromatography-tandem mass spectrometry. The method for measuring the sensory related amide compounds in the main stream smoke of the cigarettes can effectively analyze various sensory related amide compounds with obvious physical and chemical property differences and larger content level in the smoke of the cigarettes.
Description
Technical Field
The invention relates to a method for measuring sensory related amide compounds in cigarette mainstream smoke, and particularly belongs to the technical field of analysis of trace chemical substances in cigarette smoke.
Background
The smoke components of cigarettes are the most direct material basis for sensory perception of smokers. The chemical components in mainstream smoke cause physiological sensation of smoker to change through smell, taste and chemical sensation (trigeminal nerve sensation). Amide is a compound in which an acyl group and an amino group are bonded, and amide may be regarded as a derivative of carboxylic acid or as ammonia or a derivative of amine. Literature studies show (Leffingwell J C,Young H J,Bernasek E.Tobacco flavoring for smoking products[M],Winston-Salem,North Carolina:1972; Wang Dingzhong, zhang Qidong, liu Junhui, etc., sensory guidance identification of bitter components of smoke and liquid chromatography-high resolution mass spectrometry [ J ], mass spectrometry report [ 2016,37 (5): 414-421), and amide compounds are important substances affecting the quality of tobacco and cigarette products. Some amide compounds can give chemical sensation, some amide compounds give bad feeling such as mildew, roughness, pungency, etc., for smokers, such as N-decanoyl pyrrolidine, N-myristoyl pyrrolidine, and some amide compounds have sweet and roast flavor, etc., and can improve sensory comfort, such as 1H-pyrrole-2-carboxamide, N-isovaleryl pyrrolidine.
Wang Dingzhong et al in sensory guidance identification and liquid chromatography-high resolution mass spectrometry of bitter taste components of smoke, adopting Cambridge filter discs to trap particulate matters of cigarette smoke, extracting with ethanol, removing ethanol, re-dissolving with water, removing water to obtain water-soluble components, separating water-soluble components by gel chromatography, determining bitter taste characteristic components by sensory evaluation, and adopting a Q-Exactive type LC-HRMS instrument to identify and quantitatively analyze bitter taste components in main stream smoke of cigarettes. The experimental process is extremely tedious and time-consuming, and only 4 sensory related amide compounds (nicotinamide, N-methylnicotinamide, N-ethylnicotinamide and 3-ethyl-4-methyl-3-pyrrol-2-one) can be quantitatively analyzed. Because of the large difference of physicochemical properties (structure, molecular weight, solubility, volatility and the like) of different amide compounds, the content level difference of the different amide compounds in cigarette smoke is large, and meanwhile, the different amide compounds are interfered by complex components in the cigarette smoke, so that various sensory related amide compounds in the main stream smoke of the cigarette are difficult to extract rapidly and effectively, 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 main stream smoke of cigarettes, which can be used for simultaneously and rapidly and effectively extracting various sensory related amide compounds in the smoke of cigarettes and is beneficial to realizing efficient separation and accurate quantitative analysis of the amide compounds.
The invention relates to a method for measuring sensory related amide compounds in main stream smoke of cigarettes, which comprises the following steps:
1) A smoking machine is adopted to smoke cigarettes, so that main stream smoke sequentially passes through a filter disc and XAD-4 resin;
2) Mixing the filter disc, XAD-4 resin, an internal standard substance, trialkylamine and an extraction solvent after the suction is finished, and extracting amide compounds in the filter disc and the XAD-4 resin to obtain an extract;
3) Purifying the extracting solution by graphitized carbon black, and detecting and analyzing the amide compounds in the purified solution by gas chromatography-tandem mass spectrometry.
According to the method for measuring the sensory related amide compounds in the main stream smoke of the cigarettes, disclosed by the invention, the sample extraction process is simple and convenient, and various sensory related amide compounds with obvious physical and chemical property differences can be effectively extracted in a time-saving and labor-saving manner; compared with the traditional solid phase extraction, the extraction liquid purification adopts the dispersion solid phase extraction, does not need to use a large amount of organic solvents for elution or concentration operation, and is beneficial to improving the high-efficiency separation of amide compounds and the accuracy of accurate quantitative analysis.
The sensory related amide compound is 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, furfuryl amide, N-decanoyl pyrrolidine, N-ethyl nicotinamide, N-methyl nicotinamide, 1H-pyrrole-2-formamide, nicotinamide and N-myristoyl pyrrolidine. The organoleptic properties of each amide are shown in Table 1.
Table 1 organoleptic Properties of amides
The filter sheet is used for trapping particulate matters in main stream smoke, and the XAD-4 resin is used for trapping gas phase components in the main stream smoke. Wherein the filter disc is connected with the smoking machine by being arranged in the cigarette holder, and the XAD-4 resin is connected with the smoking machine after being arranged in the adsorption tube. When the cigarette is smoked by a smoking machine, the smoking is carried out according to a conventional or deep smoking scheme.
Preferably, the filter is a fiberglass filter. The amount of XAD-4 resin adopted for each 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, the mixing is to mix a filter sheet for capturing particulate matters in main stream smoke when each 4-8 cigarettes are smoked, XAD-4 resin, 25-100 mu L of internal standard solution and 5-25 mL of trialkylamine extraction solvent solution; the concentration of the trialkylamine extraction solvent solution is 100 to 500ppm. The extraction solvent solution of trialkylamine is formed by dissolving trialkylamine in an extraction solvent. Further, the concentration of the internal standard solution is 50-100 ppm. The internal standard solution is formed by dissolving an internal standard in a solvent consistent with the extraction solvent.
The internal standard is one or any combination of deuterated acetamide, deuterated acrylamide and deuterated nicotinamide.
In order to extract the sensory related amide compounds from the glass fiber filter and the XAD-4 resin completely, 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 on all 19 sensory related amide compounds in 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 rotating speed of vortex is 2000r/min, and the time is 10min.
In order to enhance the purification effect and ensure that the sensory related amide compounds have no residue in graphitized carbon black, the amount of graphitized carbon black adopted for each 1mL of extracting solution is 20-100 mg. Specifically, the purification comprises the steps of: adding graphitized carbon black into the extracting solution, and performing solid-liquid separation after vortex. In the purification process, the rotating speed of vortex is 2000r/min, and the time is 5min. The solid-liquid separation is centrifugation.
And (3) during gas chromatography-tandem mass spectrometry separation analysis, taking a liquid phase obtained by solid-liquid separation, filtering by adopting an organic phase filter membrane, and then sampling. The pore size of the organic phase filter used was 0.45. Mu.m.
In order to ensure that the chromatographic separation of various amide compounds is good, and the stronger peak intensity and the good peak shape are obtained, further, the stationary phase of a chromatographic column adopted in chromatographic analysis is polyethylene glycol or polyethylene glycol modified by nitroterephthalic acid. The separation chromatographic column used in chromatographic analysis is a capillary chromatographic column. The column size was 30m×0.25mm×0.25 μm.
In order to reduce escape of the sensory related amide compounds during gasification of the sample inlet, the sample injection mode adopted during separation analysis of the gas chromatograph-tandem mass spectrum is pulse non-split, and the pulse pressure is 100-300 kPa.
Further, the chromatographic conditions of the detection analysis are: the temperature of the sample inlet is 200-250 ℃, the sample injection 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 raising program is kept at 40-60 ℃ for 1-3 min, then the temperature is raised to 230-250 ℃ at the speed of 3-8 ℃/min, the temperature is kept for 10-20 min, and the temperature of the transmission line is 230-250 ℃; the mass spectrum conditions are as follows: the ionization mode is EI, the scanning mode is 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 mu A, the collision gas is argon, and the pressure is 1.0-2.0 mTorr. The detection analysis in the invention adopts gas chromatography-tandem mass spectrometry multi-reaction monitoring. The detection parameter has the advantages of strong selectivity, high sensitivity and high accuracy. The multi-reaction detection parameters and internal standards of the 19 sensory related amide compounds are shown in table 2.
TABLE 2 Multi-response monitoring parameters and internal standards for 19 sensory related amides
Drawings
FIG. 1 is a schematic view of a main stream smoke trap of a cigarette in an embodiment of the invention, wherein the main stream smoke trap comprises a 1-cigarette, a 2-cigarette holder, a 3-glass fiber filter, a 4-smoking machine connecting port, a 5-adsorption tube and 6-XAD-4 resin;
FIG. 2 is a chromatogram of 19 kinds of amide compounds in experimental example 3 of the present invention using polyethylene glycol capillary chromatographic column;
FIG. 3 is a chromatogram of 19 amides from example 3 of the present invention using a 6% cyanopropylphenyl-94% dimethylsiloxane capillary chromatography column;
FIG. 4-a is a graph of acetamide chromatograms of Experimental example 3 of the present invention using polyethylene glycol capillary chromatography columns;
FIG. 4-b is a graph of acetamide chromatograms of Experimental example 3 of the present invention using a 6% cyanopropylphenyl-94% dimethylsiloxane capillary chromatography column;
FIG. 5-a is a chromatogram of N-crotonylpyrrolidine for use in experimental example 3 of the present invention using a polyethylene glycol capillary chromatography column;
FIG. 5-b is a graph of N-crotonylpyrrolidine chromatograms of experimental example 3 of the present invention using a 6% cyanopropylphenyl-94% dimethylsiloxane capillary chromatography column;
FIG. 6-a is a chromatogram of 3-ethyl-4-methyl-3-pyrrol-2-one using polyethylene glycol capillary chromatography column in Experimental example 3 of 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 chromatography column in accordance with example 3 of the present invention;
FIG. 7-a is a diagram showing a furfuryl amide chromatogram when a polyethylene glycol capillary chromatographic column is used in Experimental example 3 in the present invention;
FIG. 7-b is a furfuryl amide chromatogram of Experimental example 3 of the present invention using a 6% cyanopropylphenyl-94% dimethylsiloxane capillary chromatography column;
FIG. 8-a is a chromatogram of 1H-pyrrole-2-carboxamide of Experimental example 3 of the present invention using polyethylene glycol capillary chromatography;
FIG. 8-b is a chromatogram of 1H-pyrrole-2-carboxamide for Experimental example 3 in the present invention using a 6% cyanopropylphenyl-94% dimethylsiloxane capillary chromatography 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 invention is further illustrated by the following examples.
Examples
The method for measuring the sensory related amide compounds in the main stream smoke of the cigarette comprises the following steps:
(1) Selecting a certain flue-cured tobacco sample, respectively connecting a cigarette holder containing a glass fiber filter sheet and an XAD-4 resin (120 mg) adsorption tube into a pipeline of a smoking machine, wherein the smoking condition of the cigarette refers to GB/T16450-2004, and the smoking number of the cigarette is 8; before starting trapping, the glass fiber filter disc is put into a cigarette holder, is connected into a smoking machine, is connected with the cigarette holder through a smoking machine connecting end after XAD-40 resin is put into an adsorption tube, and is connected into the smoking machine, as shown in figure 1, when the cigarette 1 is smoked, main stream smoke sequentially passes through the glass fiber filter disc 3, the smoking machine connecting end 4 and the XAD-4 resin 6 in the adsorption tube 5 in the cigarette holder 2.
(2) After the smoking of the cigarettes is finished, the adsorbent in the glass fiber filter sheet and the adsorption tube is quickly transferred into a 15mL centrifuge tube, 25 mu L of an internal standard substance solution with the concentration of 100ppm (the internal standard substance is deuterated acetamide, deuterated acrylamide and deuterated nicotinamide) is added, 10mL of a methanol solution with the concentration of 200ppm triethylamine is added, and the mixture is swirled for 10min at the speed of 2000 r/min.
(3) Transfer 1mL of the extract to a 2mL centrifuge tube, add 50mg graphitized carbon black and vortex at 2000r/min for 5min. 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 gas chromatography-tandem mass spectrometry detection conditions are as follows:
Chromatographic conditions: the chromatographic column is polyethylene glycol capillary chromatographic column (model DB-FFAP,30m×0.25mm×0.25 μm); the sample injection mode is pulse non-shunt, and the pulse pressure is 200kPa; the temperature of the sample inlet is 240 ℃; the sample injection amount is 1 mu L; the carrier gas is helium, and the constant flow rate is 1mL/min; heating program: maintaining at 50deg.C for 1min, heating to 235deg.C at a rate of 5deg.C/min, and maintaining for 15min; the transmission line temperature was 230 ℃.
Mass spectrometry conditions: the ionization mode is EI; the scanning mode is a multi-reaction monitoring mode; the solvent delay was 7min; the temperature of the ion source is 280 ℃; the filament emission current was 50 μa; the collision gas was argon, at a pressure of 1.0mTorr.
The multi-reaction monitoring parameters of the 19 kinds of amide compounds are shown in table 2, and the standard curves of the respective amide compounds are shown in table 3.
TABLE 3 Standard curves for amide compounds
| Amide compounds | Linear equation | Correlation coefficient |
| N-formyl pyrrolidines | Y＝-0.0557+0.0054*X | 0.9996 |
| Acetamide compound | 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 |
| Isopentanamide | Y＝-0.0159+0.0022*X | 0.9998 |
| N-isovalerylpyrrolidine | Y＝-0.0020+0.0057*X | 0.9994 |
| N-propionyl pyrrolidine | Y＝0.0201+0.0067*X | 0.9996 |
| N-crotonylpyrrolidine | Y＝0.0852+0.0086*X | 0.9999 |
| 3-Ethyl-4-methyl-3-pyrrol-2-one | Y＝0.0154+0.0062*X | 0.9993 |
| Furfuryl amides | Y＝-0.3678+0.0501*X | 0.9991 |
| N-decanoylpyrrolidine | 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-carboxamide | Y＝-0.0667+0.0120*X | 0.9998 |
| Nicotinamide | Y＝-0.0699+0.0089*X | 0.9998 |
| N-myristoylpyrrolidine | Y＝0.0044+0.0079*X | 0.9994 |
The detection results of 19 kinds of amide compounds in the flue-cured tobacco sample are as follows: n-formyl pyrrolidine 198.9 ng/g, acetamide 2245.1 ng/g, isobutyramide 65.7 ng/g, propionamide 754.7 ng/g, N-isobutyrylpyrrolidine undetected, N-acetyl pyrrolidine 259.1 ng/g, N-butyrylpyrrolidine 6.0 ng/g, isovaleramide 551.3 ng/g, N-isovalerylpyrrolidine 7.7 ng/g, N-propionylpyrrolidine undetected, N-crotonylpyrrolidine 1.9 ng/g, 3-ethyl-4-methyl-3-pyrrol-2-one 1610.9 ng/g, furfuryl amide 175.9 ng/g, N-decanoylpyrrolidine undetected, N-ethyl nicotinamide 1.6 ng/g, N-methyl nicotinamide 334.3 ng/g, 1H-pyrrole-2-carboxamide 947.1 ng/g, nicotinamide 489.5 ng/g, N-myristoylpyrrolidine undetected.
According to the detection result of the flue-cured tobacco sample, the content range of 19 kinds of amide compounds is 1.6-2245.1 ng/cig, the content level difference of different amide compounds in cigarette smoke is huge, and 4 orders of magnitude are covered.
Experimental example 1
Experiments were performed using the flue-cured tobacco samples of the examples, which detected 15 kinds of amide compounds, 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 sheet and the adsorption tube after trapping the flue gas, to investigate the effect of trialkylamine on extraction.
The amide compounds in the glass fiber filter and the adsorption tube were extracted with methanol and a methanol solution containing 200ppm of triethylamine, respectively, and the extraction rate results are shown in Table 3 under the same conditions as in the examples. As shown in Table 4, the extraction ratio of methanol to 19 kinds of amide compounds was in the range of 0.72 to 1.00, and the extraction ratio of triethylamine/methanol was in the range of 0.98 to 1.00, and the extraction ratio was remarkably improved after triethylamine was added to methanol.
TABLE 4 influence of different extraction solvents on the extraction effect
Experimental example 2
Experiments were performed using flue-cured tobacco samples as in the examples. 15 kinds of 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 the glass fiber filter sheet after flue gas is captured and XAD-4 resin in an adsorption tube.
The flue gas substrate was purified with N-Propylethylenediamine (PSA) adsorbent, C18 adsorbent, graphitized Carbon Black (GCB), respectively, under the same conditions as in the examples. The recovery rate after the substrate purification is shown in Table 5. The PSA has certain purifying effect on the flue gas matrix, the recovery rate of 19 amide compounds is in the range of 0.77-0.98, and the recovery rate is low. C18 has poor purifying effect on the flue gas matrix, the recovery rate ranges from 0.83 to 1.00, and the recovery rate is low. The graphitized carbon black has good purifying effect, the recovery rate ranges from 0.97 to 1.00, and the recovery rate is good.
TABLE 5 influence of different adsorbents on purification effect
Experimental example 3
Preparing a mixed standard solution of 19 amide compounds with the concentration of 10ppm, and carrying out gas chromatography-tandem mass spectrometry separation analysis. The 19 kinds of amide compounds were separated by using a capillary column (model DB-624, 60 m.times.0.25 mm.times.1.4 μm) having a stationary phase of 6% cyanopropylphenyl-94% dimethylsiloxane and a capillary column (model DB-FFAP,30 m.times.0.25 mm.times.0.25 μm) having a stationary phase of polyethylene glycol, respectively, and the mass spectrometry was performed by full scanning, and other gas chromatography-tandem mass spectrometry separation and analysis conditions were the same as in the examples.
The full-scan chromatogram of 19 amide compounds is shown in figure 3 using a 6% cyanopropylphenyl-94% dimethylsiloxane capillary column. As can be seen from FIG. 3, N-decanoylpyrrolidine and N-myristoylpyrrolidine showed no peak, and the 5 compounds of acetamide, N-crotonylpyrrolidine, 3-ethyl-4-methyl-3-pyrrol-2-one, furfuryl amide and 1H-pyrrole-2-carboxamide showed a tailing of the peaks and had low peak intensities. Chromatograms of acetamide, N-crotonylpyrrolidine, 3-ethyl-4-methyl-3-pyrrol-2-one, furfuryl amide, 1H-pyrrole-2-carboxamide using a 6% cyanopropylphenyl-94% dimethylsiloxane capillary chromatography column are shown in fig. 4-b, fig. 5-b, fig. 6-b, fig. 7-b, fig. 8-b.
The full-scanning chromatogram of 19 kinds of amide compounds is shown in figure 2 by using polyethylene glycol capillary chromatographic column. The chromatographic peak shape of each amide compound is symmetrical, the peak intensity is high, and no tailing exists can be seen from figure 2. By adopting the chromatographic column, 19 kinds of amide compounds can be well separated by a thin liquid film with the length of 30m and the thickness of 0.25 mu m, and the cost is low. When polyethylene glycol capillary chromatographic column is adopted, the chromatograms of acetamide, N-crotonylpyrrolidine, 3-ethyl-4-methyl-3-pyrrol-2-one, furfuryl amide 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 the polyethylene glycol capillary chromatographic column is adopted is shown in figure 9.
Experimental example 4
Preparing a mixed standard solution of 19 kinds of amide compounds with the concentration of 0.1ppm, and carrying out gas chromatography-tandem mass spectrometry separation analysis. The sample injection mode is respectively set to be a split ratio of 10:1 (namely, the ratio of the carrier gas flow rate of a split outlet to the carrier gas flow rate of a 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 (the electromagnetic valve of the split outlet is closed during sample injection), pulse no split (the electromagnetic valve of the split outlet is closed during sample injection, and pulse pressure is applied at the sample injection port), and other gas chromatography-tandem mass spectrometry separation analysis conditions are the same as in the embodiment. The chromatographic peak area of the amide compound under the condition of the split ratio of 10:1 is set as 1, and the chromatographic peak responses of the compounds under different sample injection modes are compared, and the comparison result is shown in Table 6. At a split ratio of 10:1, the chromatographic peak response of each amide compound is the lowest; when the sample injection mode is pulse non-shunt, the chromatographic peak response is improved by 4.2-10.6 times, and the detection sensitivity is obviously improved.
TABLE 6 chromatographic peak areas and fold improvement for 0.1ppm Standard solutions under different sample injection modes
Experimental example 5
Preparing 19 kinds of amide compound mixed standard solutions, performing gas chromatography-tandem mass spectrometry separation 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 a labeling recovery experiment, measured 3 times in parallel, and the labeling recovery was calculated, and experimental data are shown in table 7.
TABLE 7 detection limits and recovery rates of 19 sensory related amide compounds
| Amide compounds | Detection limit ng/mL | Recovery% |
| N-formyl pyrrolidines | 10.3 | 105.4 |
| Acetamide compound | 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 |
| Isopentanamide | 33.2 | 94.6 |
| N-isovalerylpyrrolidine | 8.8 | 93.4 |
| N-propionyl pyrrolidine | 6.9 | 91.8 |
| N-crotonylpyrrolidine | 4.3 | 107.2 |
| 3-Ethyl-4-methyl-3-pyrrol-2-one | 8.4 | 95.5 |
| Furfuryl amides | 2.3 | 98.5 |
| N-decanoylpyrrolidine | 16.2 | 102.6 |
| N-ethyl nicotinamide | 3.2 | 93.3 |
| N-methylnicotinamide | 6.6 | 97.2 |
| 1H-pyrrole-2-carboxamide | 2.9 | 105.4 |
| Nicotinamide | 4.1 | 109.4 |
| N-myristoylpyrrolidine | 3.3 | 103.4 |
As can be seen from the data in Table 7, the detection limit range of 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 measuring the sensory related amide compounds in the tobacco and tobacco products has the advantages of high sensitivity and high accuracy.
Claims (6)
1. The method for measuring the sensory related amide compounds in the main stream smoke of the cigarettes is characterized by comprising the following steps of:
1) A smoking machine is adopted to smoke cigarettes, so that main stream smoke sequentially passes through a filter disc and XAD-4 resin;
2) Mixing the filter disc, XAD-4 resin, an internal standard substance, trialkylamine and an extraction solvent after the suction is finished, and extracting amide compounds in the filter disc and the XAD-4 resin to obtain an extract;
3) Purifying the extracting solution by graphitized carbon black, and detecting and analyzing the amide compounds in the purified solution by adopting gas chromatography-tandem mass spectrometry;
The sensory related amide compound is 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-one, furfuryl amide, N-decanoyl pyrrolidine, N-ethyl nicotinamide, N-methyl nicotinamide, 1H-pyrrole-2-carboxamide, nicotinamide and N-myristoyl pyrrolidine;
extracting by adopting a vortex mode; the amount of graphitized carbon black adopted for each 1mL of extracting solution is 20-100 mg; the extraction liquid is purified by adopting dispersed solid phase extraction;
the chromatographic column for detection and analysis is a polyethylene glycol capillary chromatographic column, the model DB-FFAP is 30m multiplied by 0.25mm multiplied by 0.25 mu m;
the sample injection mode adopted in the gas chromatography-tandem mass spectrometry separation analysis is pulse without split flow, and the pulse pressure is 100-300 kPa;
The chromatographic conditions of the detection and analysis are as follows: the temperature of the sample inlet is 200-250 ℃, the sample injection 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 raising program is kept at 40-60 ℃ for 1-3 min, then the temperature is raised to 230-250 ℃ at the speed of 3-8 ℃/min, the temperature is kept for 10-20 min, and the temperature of the transmission line is 230-250 ℃;
The mass spectrum conditions are as follows: the ionization mode is EI, the scanning mode is 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 mu A, the collision gas is argon, and the pressure is 1.0-2.0 mTorr.
2. The method for determining the sensory related amide compounds in mainstream smoke of a cigarette according to claim 1, wherein the filter is a glass fiber filter; the amount of XAD-4 resin adopted for each 4-8 cigarettes is 40-200 mg.
3. The method for measuring sensory related amide compounds in mainstream smoke of cigarettes according to claim 2, wherein the mixing is mixing a filter sheet for capturing particulate matters in mainstream smoke when each 4 to 8 cigarettes are smoked, XAD-4 resin, 25 to 100 μl of internal standard solution, and 5 to 25mL of trialkylamine extraction solvent solution; the concentration of the trialkylamine extraction solvent solution is 100 to 500ppm.
4. The method for determining the sensory related amide compounds in the mainstream smoke of cigarettes according to claim 1, wherein the internal standard is one or any combination of deuterated acetamide, deuterated acrylamide and deuterated nicotinamide.
5. The method for determining the sensory related amide compounds in the mainstream smoke of 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 compounds in the mainstream smoke of cigarettes according to claim 1 or 5, wherein the trialkylamine is triethylamine and/or tripropylamine.
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