CN114034790B - Method for determining sensory related amide compounds in tobacco and tobacco products - Google Patents
Method for determining sensory related amide compounds in tobacco and tobacco products Download PDFInfo
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- CN114034790B CN114034790B CN202111306211.4A CN202111306211A CN114034790B CN 114034790 B CN114034790 B CN 114034790B CN 202111306211 A CN202111306211 A CN 202111306211A CN 114034790 B CN114034790 B CN 114034790B
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- -1 amide compounds Chemical class 0.000 title claims abstract description 75
- 241000208125 Nicotiana Species 0.000 title claims abstract description 41
- 235000002637 Nicotiana tabacum Nutrition 0.000 title claims abstract description 41
- 230000001953 sensory effect Effects 0.000 title claims abstract description 37
- 235000019505 tobacco product Nutrition 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims abstract description 20
- 125000005270 trialkylamine group Chemical group 0.000 claims abstract description 18
- 238000004458 analytical method Methods 0.000 claims abstract description 17
- 238000004885 tandem mass spectrometry Methods 0.000 claims abstract description 15
- 239000006229 carbon black Substances 0.000 claims abstract description 13
- 239000000126 substance Substances 0.000 claims abstract description 13
- 238000002156 mixing Methods 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 19
- 239000000243 solution Substances 0.000 claims description 19
- 239000007789 gas Substances 0.000 claims description 17
- 239000002202 Polyethylene glycol Substances 0.000 claims description 16
- 229920001223 polyethylene glycol Polymers 0.000 claims description 16
- 238000001514 detection method Methods 0.000 claims description 15
- 238000004587 chromatography analysis Methods 0.000 claims description 14
- 238000002347 injection Methods 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- 238000000926 separation method Methods 0.000 claims description 13
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims description 12
- 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 11
- 239000012086 standard solution Substances 0.000 claims description 11
- RLOQBKJCOAXOLR-UHFFFAOYSA-N 1h-pyrrole-2-carboxamide Chemical compound NC(=O)C1=CC=CN1 RLOQBKJCOAXOLR-UHFFFAOYSA-N 0.000 claims description 9
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 8
- TVFIYRKPCACCNL-UHFFFAOYSA-N furan-2-carboxamide Chemical compound NC(=O)C1=CC=CO1 TVFIYRKPCACCNL-UHFFFAOYSA-N 0.000 claims description 8
- WFSIAHMONQXMJH-UHFFFAOYSA-N 1-pyrrolidin-1-yldecan-1-one Chemical compound CCCCCCCCCC(=O)N1CCCC1 WFSIAHMONQXMJH-UHFFFAOYSA-N 0.000 claims description 7
- LHCODHVVGGYIOZ-UHFFFAOYSA-N 1-pyrrolidin-1-yltetradecan-1-one Chemical compound CCCCCCCCCCCCCC(=O)N1CCCC1 LHCODHVVGGYIOZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000012159 carrier gas Substances 0.000 claims description 7
- ZXOAHASJYIUCBG-UHFFFAOYSA-N n-ethylpyridine-3-carboxamide Chemical compound CCNC(=O)C1=CC=CN=C1 ZXOAHASJYIUCBG-UHFFFAOYSA-N 0.000 claims description 7
- QEAWNPFOQLJDAY-UHFFFAOYSA-N 1-pyrrolidin-1-ylbutan-1-one Chemical compound CCCC(=O)N1CCCC1 QEAWNPFOQLJDAY-UHFFFAOYSA-N 0.000 claims description 6
- YEJJUJNTWYKFLS-UHFFFAOYSA-N 1-pyrrolidin-1-ylpropan-1-one Chemical compound CCC(=O)N1CCCC1 YEJJUJNTWYKFLS-UHFFFAOYSA-N 0.000 claims 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 claims 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 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
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 229940047889 isobutyramide Drugs 0.000 claims description 6
- SANOUVWGPVYVAV-UHFFFAOYSA-N isovaleramide Chemical compound CC(C)CC(N)=O SANOUVWGPVYVAV-UHFFFAOYSA-N 0.000 claims description 6
- 238000012544 monitoring process Methods 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 5
- 239000002904 solvent Substances 0.000 claims description 5
- AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 claims description 4
- LNWWQYYLZVZXKS-UHFFFAOYSA-N 1-pyrrolidin-1-ylethanone Chemical compound CC(=O)N1CCCC1 LNWWQYYLZVZXKS-UHFFFAOYSA-N 0.000 claims description 4
- 230000005526 G1 to G0 transition Effects 0.000 claims description 4
- 150000003926 acrylamides Chemical class 0.000 claims description 4
- 239000011570 nicotinamide Substances 0.000 claims description 4
- 229960003966 nicotinamide Drugs 0.000 claims description 4
- 235000005152 nicotinamide Nutrition 0.000 claims description 4
- 150000005480 nicotinamides Chemical class 0.000 claims description 4
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 4
- 229940080818 propionamide Drugs 0.000 claims description 4
- 230000035485 pulse pressure Effects 0.000 claims description 4
- 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
- 150000003869 acetamides Chemical class 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
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 2
- 238000000605 extraction Methods 0.000 abstract description 11
- 238000000746 purification Methods 0.000 abstract description 4
- 239000000523 sample Substances 0.000 description 30
- 238000011084 recovery Methods 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 235000009508 confectionery Nutrition 0.000 description 5
- 239000000779 smoke Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 235000019658 bitter taste Nutrition 0.000 description 4
- 235000019504 cigarettes Nutrition 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- 238000010586 diagram Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 235000019640 taste Nutrition 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 240000008574 Capsicum frutescens Species 0.000 description 2
- 235000002568 Capsicum frutescens Nutrition 0.000 description 2
- 238000013051 Liquid chromatography–high-resolution mass spectrometry Methods 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 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
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000011156 evaluation Methods 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
- 239000012535 impurity Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- CFNHVUGPXZUTRR-UHFFFAOYSA-N n'-propylethane-1,2-diamine Chemical group CCCNCCN CFNHVUGPXZUTRR-UHFFFAOYSA-N 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000019633 pungent taste Nutrition 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 235000019615 sensations Nutrition 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
-
- 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
- G01N30/86—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
Abstract
The invention relates to a method for determining sensory related amide compounds in tobacco and tobacco products, and belongs to the technical field of analysis of trace chemical substances in tobacco and tobacco products. The method comprises the following steps: 1) Mixing a sample to be detected with graphitized carbon black, an internal standard substance, trialkylamine and an extracting agent, and extracting the sample to be detected to obtain an extracting solution; 2) And detecting and analyzing the amide compounds in the obtained extracting solution by adopting gas chromatography-tandem mass spectrometry. The method for measuring the sensory related amide compounds in the tobacco and the tobacco products integrates the extraction and purification of samples, is simple to operate, saves time and labor, and can effectively analyze various sensory related amide compounds with obvious physical and chemical property differences and larger content level differences in complex matrixes of the tobacco and the tobacco products.
Description
Technical Field
The invention relates to a method for determining sensory related amide compounds in tobacco and tobacco products, and in particular belongs to the technical field of analysis of trace chemical substances in tobacco and tobacco products.
Background
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 have shown that (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 directed identification of bitter constituents of smoke and liquid chromatography-high resolution mass spectrometry [ J ], mass spectrometry, 2016,37 (5): 414-421), amide compounds are a class of important substances affecting the quality of tobacco and cigarette products. Some amide compounds can give chemical sensation to smokers, some amide compounds give bad feeling such as mildew, roughness, pungency, etc., and some amide compounds have taste such as sweet and roast flavor for improving sensory comfort.
Wang Dingzhong in "sensory guidance identification and liquid chromatography-high resolution mass spectrometry analysis of bitter component of smoke", cambridge filter is adopted to trap particulate matters of cigarette smoke, ethanol is extracted, ethanol is removed, water is redissolved, water is removed to obtain water-soluble components, then gel chromatography is used to separate the water-soluble components, bitter characteristic components are determined through sensory evaluation, and Q-exact LC-HRMS instrument is adopted to identify and quantitatively analyze bitter components in main stream smoke of cigarettes. The experimental process is extremely complicated and time-consuming, and only 4 sensory related amide compounds (nicotinamide, N-methyl nicotinamide, N-ethyl nicotinamide and 3-ethyl-4-methyl-3-pyrrole-2-ketone) in the main stream smoke of the cigarette can be quantitatively analyzed. At present, no literature report exists on a method for measuring sensory related amide compounds in tobacco and tobacco products. Because of the large difference of physical and chemical properties (structure, molecular weight, solubility, volatility and the like) of different amide compounds, the content level difference of the different amide compounds in tobacco and tobacco products is also large, and meanwhile, the different amide compounds are interfered by complex matrixes of the tobacco and the tobacco products, so that the various sensory related amide compounds in the tobacco and the tobacco products are difficult to extract rapidly and effectively and accurately and quantitatively analyze.
Disclosure of Invention
The invention aims to provide a method for measuring sensory related amide compounds in tobacco and tobacco products, which can be used for rapidly and effectively extracting various sensory related amide compounds in the tobacco and the tobacco products at the same time, so as to realize accurate quantitative analysis of the various sensory related amide compounds.
In order to achieve the above purpose, the technical scheme adopted by the technical scheme of the invention is as follows:
a method for measuring sensory related amide compounds in tobacco and tobacco products comprises the following steps: 1) Mixing a sample to be detected with graphitized carbon black, an internal standard substance, trialkylamine and an extracting agent, and extracting the sample to be detected to obtain an extracting solution; 2) And detecting and analyzing the amide compounds in the obtained extracting solution by adopting gas chromatography-tandem mass spectrometry.
According to the method for measuring the sensory related amide compounds in the tobacco and the tobacco products, the graphitized carbon black can remove impurities in the tobacco and the tobacco products, the target compounds can be well purified, the trialkylamine can assist in extracting solvents to extract the target compounds from the tobacco and the tobacco products, the sample extraction and purification are integrated, the operation is simple, time and labor are saved, and meanwhile, the method can effectively analyze various sensory related amide compounds with obvious physical and chemical property differences and larger content level differences in complex matrixes of the tobacco and the tobacco products.
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
| Sequence number | Amides and their use | Chemical feel | Taste sense | Smell sense |
| 1 | N-formyl pyrrolidines | Weak and weak | Weak and weak | |
| 2 | Acetamide compound | Is that | Mould and coarse taste | |
| 3 | Isobutyramide | Is that | Mildewed smell | |
| 4 | Propionamide | Is that | Mildewed and coarse | |
| 5 | N-isobutyrylpyrrolidine | Increase fullness and roughness | ||
| 6 | N-acetylpyrrolidine | Slightly spicy | ||
| 7 | N-butyrylpyrrolidine | Is that | Mildewed smell | |
| 8 | Isopentanamide | Is that | Roughness of | |
| 9 | N-isovalerylpyrrolidine | Sweet and roasted incense | ||
| 10 | N-propionyl pyrrolidine | Increase fullness, fineness and sweet fragrance | ||
| 11 | N-crotonylpyrrolidine | Sweet and delicate | ||
| 12 | 3-ethyl-4-methyl-3-pyrrol-2-one | Slightly bitter taste | ||
| 13 | Furfuryl amides | Mildew and grass fragrance | Increase fullness | |
| 14 | N-decanoylpyrrolidine | Is that | Spicy and hot pepper flavor | |
| 15 | N-ethyl nicotinamide | Slightly bitter taste | ||
| 16 | N-methylnicotinamide | Slightly bitter taste | ||
| 17 | 1H-pyrrole-2-carboxamide | Sweet and roasted incense | ||
| 18 | Nicotinamide | Slightly bitter taste | ||
| 19 | N-myristoylpyrrolidine | Spicy and hot pepper flavor |
In order to enhance the matrix purification effect of tobacco and tobacco products and ensure that sensory related amide compounds have no residue in graphitized carbon black, the mass of graphitized carbon black adopted per 1g of sample to be detected is 0.2-1 g. The mass of the trialkylamine adopted for each 1g of sample to be tested is 1-5 mug.
Further, the mixing is to mix the sample to be measured, graphitized carbon black, the internal standard solution and the trialkylamine extractant solution. Every 1g of the sample to be tested correspondingly adopts 25-100 mu L of internal standard solution. 5-25 mL of trialkylamine extractant solution is correspondingly adopted for each 1g of sample to be detected. The internal standard solution is formed by dissolving an internal standard in a solvent consistent with the extractant. The trialkylamine extractant solution is formed by dissolving trialkylamine in an extractant.
Further, the concentration of the internal standard solution is 50-100 ppm.
Further, the concentration of the trialkylamine extractant solution is 100 to 500ppm.
Further, the internal standard is one or any combination of deuterated acetamide, deuterated acrylamide and deuterated nicotinamide.
In order to fully extract various sensory related amide compounds from a sample to be tested, the extracting agent 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 19 sensory related amide compounds in table 1. Preferably, the extractant solution of the trialkylamine is a methanol solution of triethylamine. Specifically, the extraction comprises the steps of: vortex the extracting solution and then separate the solid and the liquid. In the extraction 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 a sample inlet and improve detection sensitivity, a sample injection mode adopted during separation analysis of gas chromatography-tandem mass spectrometry is pulse without shunt, 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. The detection analysis in the invention adopts gas chromatography-tandem mass spectrometry multi-reaction monitoring. The multi-reaction detection parameters and internal standards of the 19 sensory related amide compounds are shown in table 2, and the detection parameters have the advantages of strong selectivity, high sensitivity and high accuracy.
TABLE 2 Multi-response monitoring parameters and internal standards for 19 sensory related amides
Drawings
FIG. 1 is a sample solution physical diagram of the dispersion of different dispersants in experimental example 2 in the present invention;
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 tobacco and the tobacco products comprises the following steps:
1g of tobacco leaf powder sample is weighed, 0.5g of graphitized carbon black is added, after uniform mixing, 25 mu L of internal standard solution (the internal standard is deuterated acetamide, deuterated acrylamide and deuterated nicotinamide) with the concentration of 100ppm is added, 10mL of methanol solution containing 200ppm of triethylamine is added, vortex is carried out for 10min at the speed of 2000r/min, centrifugation is carried out for 3min at the speed of 8000r/min, supernatant is taken, and after passing through a 0.45 mu m organic phase filter membrane, separation analysis is carried out on the supernatant by adopting 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 of 19 sensory related amide compounds in Mass Spectrometry
The detection results of 19 kinds of amide compounds in the tobacco leaf sample are as follows: n-formyl pyrrolidine 1167.6ng/g, acetamide 6119.8ng/g, isobutyramide undetected, propionamide 782.2ng/g, N-isobutyrylpyrrolidine undetected, N-acetyl pyrrolidine 460.9ng/g, N-butyrylpyrrolidine undetected, isovaleramide undetected, N-isovalerylpyrrolidine undetected, N-propionylpyrrolidine undetected, N-crotonylpyrrolidine undetected, 3-ethyl-4-methyl-3-pyrrol-2-one 966.5ng/g, furfuryl amide 241.9ng/g, N-decanoylpyrrolidine undetected, N-ethyl nicotinamide undetected, N-methyl nicotinamide 1467.9ng/g, 1H-pyrrole-2-carboxamide 43.3ng/g, nicotinamide 4045.3ng/g, N-myristoylpyrrolidine undetected. The content of the 19 kinds of amide compounds is 43.3-6119.8 ng/g.
Experimental example 1
Experiments were performed using tobacco samples from the examples. The tobacco leaf sample detects 9 kinds of amide compounds, and a certain amount of undetected compounds (isobutyramide, N-isobutyrylpyrrolidine, N-butyrylpyrrolidine, isovaleramide, N-isovalerylpyrrolidine, N-propionyl pyrrolidine, N-crotonylpyrrolidine, N-decanoylpyrrolidine, N-ethyl nicotinamide and N-myristoylpyrrolidine) are added into the sample to study the influence of trialkylamine on the extraction effect.
The amide compounds in the tobacco leaves 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 0.75 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 extractants on extraction effect
Experimental example 2
Experiments were performed using tobacco samples from the examples. The tobacco leaf sample detects 9 kinds of amide compounds, and a certain amount of undetected compounds (isobutyramide, N-isobutyrylpyrrolidine, N-butyrylpyrrolidine, isovaleramide, N-isovalerylpyrrolidine, N-propionyl pyrrolidine, N-crotonylpyrrolidine, N-decanoylpyrrolidine, N-ethyl nicotinamide and N-myristoylpyrrolidine) are added into the sample.
Graphitized Carbon Black (GCB) in the examples was replaced with N-Propylethylenediamine (PSA) adsorbent, C18 adsorbent, and the other conditions were the same as in the examples. The sample solution is shown in the physical diagram of FIG. 1, and the recovery rate results are shown in Table 5.PSA has certain purifying effect on tobacco substrate, recovery rate of 19 kinds of amide compounds is 0.44-1.00, and recovery rate is low. C18 has poor purifying effect on tobacco substrate, 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 substances on the 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 are adopted to carry out the experiment of the standard adding recovery rate, the parallel measurement is carried out for 3 times, and the standard adding recovery rate is calculated. The experimental data are shown in table 7.
TABLE 7 detection limits and recovery rates of 19 sensory related amide compounds
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.
Comparative example
1g of tobacco leaf powder sample is weighed, 25. Mu.L of an internal standard solution (the internal standard is deuterated acetamide, deuterated acrylamide and deuterated nicotinamide) with the concentration of 100ppm is added, 10mL of a methanol solution containing 200ppm of triethylamine is added, and the mixture is vortexed at the speed of 2000r/min for 10min. Centrifuging at 8000r/min for 3min, collecting supernatant, adding 0.5g graphitized carbon black, swirling at 2000r/min for 10min, centrifuging at 8000r/min for 3min, collecting supernatant, filtering with 0.45 μm organic phase filter membrane, and performing gas chromatography-tandem mass spectrometry separation analysis under the same experimental conditions as in the examples, wherein the detection results are shown in Table 8.
Table 8 results of detection of 19 sensory related amide compounds in tobacco leaf samples of examples and comparative examples
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Claims (6)
1. A method for determining sensory related amide compounds in tobacco and tobacco products, which is characterized by comprising the following steps:
1) Mixing a sample to be detected with graphitized carbon black, an internal standard substance, trialkylamine and an extracting agent, and extracting the sample to be detected to obtain an extracting solution;
2) Detecting and analyzing the amide compounds in the obtained extracting solution by adopting gas chromatography-tandem mass spectrometry;
the sensory related amide compounds include 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-pyrrol-2-one, furfuryl amide, N-decanoyl pyrrolidine, N-ethyl nicotinamide, N-methyl nicotinamide, 1H-pyrrole-2-carboxamide, nicotinamide and N-myristoyl pyrrolidine;
the extractant is one or any combination of methanol, acetonitrile, acetone and dichloromethane; the trialkylamine is triethylamine and/or tripropylamine; the stationary phase of the chromatographic column adopted in chromatographic analysis is polyethylene glycol or polyethylene glycol modified by nitroterephthalic acid; the sample injection mode adopted in the gas chromatography-tandem mass spectrometry separation analysis is pulse non-split, 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 temperature-raising program is 40-60 ℃ and kept 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 ion source temperature is 230-300 ℃.
2. The method for determining the sensory related amide compounds in the tobaccos and the tobacco products according to claim 1, wherein the mass of graphitized carbon black adopted per 1g of the sample to be determined is 0.2-1 g, and the mass of trialkylamine adopted per 1g of the sample to be determined is 1-5 μg.
3. The method for determining the organoleptic related amide compounds in tobacco and tobacco products according to claim 1 or 2, wherein the mixing is mixing a sample to be tested, graphitized carbon black, an internal standard solution and an extractant solution of trialkylamine; every 1g of the sample to be detected correspondingly adopts 25-100 mu L of the internal standard substance solution, and every 1g of the sample to be detected correspondingly adopts 5-25 mL of the trialkylamine extractant solution.
4. The method for measuring sensory related amide compounds in tobacco and tobacco products according to claim 1, wherein the concentration of the trialkylamine extractant solution is 100-500 ppm.
5. The method for determining the sensory related amide compounds in tobacco and tobacco products according to claim 1, wherein the internal standard is one or any combination of deuterated acetamides, deuterated acrylamides and deuterated nicotinamide.
6. The method for determining the organoleptic amide compounds in tobacco and tobacco products according to claim 1, wherein the chromatographic conditions of the detection analysis are: the sample injection amount is 1-1.5 mu L, the carrier gas is helium, and the constant flow rate is 0.8-1.5 mL/min;
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 filament emission current is 25-50 mu A, the collision gas is argon, and the pressure is 1.0-2.0 mTorr.
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