CN113203823B - Application of hydroxyl-containing compound, matrix improver and analysis method of flavor components in tobacco - Google Patents
Application of hydroxyl-containing compound, matrix improver and analysis method of flavor components in tobacco Download PDFInfo
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- CN113203823B CN113203823B CN202110432078.0A CN202110432078A CN113203823B CN 113203823 B CN113203823 B CN 113203823B CN 202110432078 A CN202110432078 A CN 202110432078A CN 113203823 B CN113203823 B CN 113203823B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 68
- 239000011159 matrix material Substances 0.000 title claims abstract description 57
- 241000208125 Nicotiana Species 0.000 title claims abstract description 27
- 235000002637 Nicotiana tabacum Nutrition 0.000 title claims abstract description 27
- 238000004458 analytical method Methods 0.000 title claims abstract description 25
- 239000000796 flavoring agent Substances 0.000 title claims abstract description 22
- 235000019634 flavors Nutrition 0.000 title claims abstract description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title abstract description 17
- 239000000126 substance Substances 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 31
- 239000000243 solution Substances 0.000 claims description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- 239000003205 fragrance Substances 0.000 claims description 20
- 238000000605 extraction Methods 0.000 claims description 16
- AXCXHFKZHDEKTP-NSCUHMNNSA-N 4-methoxycinnamaldehyde Chemical compound COC1=CC=C(\C=C\C=O)C=C1 AXCXHFKZHDEKTP-NSCUHMNNSA-N 0.000 claims description 14
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 claims description 14
- 238000004587 chromatography analysis Methods 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 12
- -1 lauryl isovalerate Chemical compound 0.000 claims description 10
- JCYHHICXJAGYEL-UHFFFAOYSA-N 3-butoxypropane-1,2-diol Chemical compound CCCCOCC(O)CO JCYHHICXJAGYEL-UHFFFAOYSA-N 0.000 claims description 9
- YNTPJHNVRFPXSS-UHFFFAOYSA-N 6-methylheptyl 2-hydroxyacetate Chemical compound C(CO)(=O)OCCCCCC(C)C YNTPJHNVRFPXSS-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims description 8
- VBICKXHEKHSIBG-UHFFFAOYSA-N beta-monoglyceryl stearate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 8
- CVJBFMVLVJZZMM-UHFFFAOYSA-N 3,7-dimethyloct-6-enyl 2-phenylacetate Chemical compound CC(C)=CCCC(C)CCOC(=O)CC1=CC=CC=C1 CVJBFMVLVJZZMM-UHFFFAOYSA-N 0.000 claims description 7
- PFRSWMCUERVSAT-UHFFFAOYSA-N 2-Methyl-3 or 5 or 6-(furfurylthio)pyrazine (mixture of isomers) Chemical compound CC1=NC=CN=C1SCC1=CC=CO1 PFRSWMCUERVSAT-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- LKUNXBRZDFMZOK-GFCCVEGCSA-N Capric acid monoglyceride Natural products CCCCCCCCCC(=O)OC[C@H](O)CO LKUNXBRZDFMZOK-GFCCVEGCSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- JBDGDEWWOUBZPM-XYPYZODXSA-N ambroxol Chemical compound NC1=C(Br)C=C(Br)C=C1CN[C@@H]1CC[C@@H](O)CC1 JBDGDEWWOUBZPM-XYPYZODXSA-N 0.000 claims description 6
- 229960005174 ambroxol Drugs 0.000 claims description 6
- 239000007853 buffer solution Substances 0.000 claims description 6
- DRUFNDDSYGNMMO-UHFFFAOYSA-N C(=CC)C=1C(=C(C(=CC=1)OC)O)CC Chemical compound C(=CC)C=1C(=C(C(=CC=1)OC)O)CC DRUFNDDSYGNMMO-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000005185 salting out Methods 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 238000005070 sampling Methods 0.000 claims description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 238000002791 soaking Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 22
- 238000004817 gas chromatography Methods 0.000 abstract description 20
- 238000001179 sorption measurement Methods 0.000 abstract description 16
- 238000001514 detection method Methods 0.000 abstract description 8
- 125000004423 acyloxy group Chemical group 0.000 abstract description 6
- 230000002401 inhibitory effect Effects 0.000 abstract description 6
- 230000002829 reductive effect Effects 0.000 abstract description 5
- 238000012360 testing method Methods 0.000 abstract description 4
- 239000007789 gas Substances 0.000 description 27
- 239000012086 standard solution Substances 0.000 description 19
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 16
- 239000000523 sample Substances 0.000 description 13
- 230000000694 effects Effects 0.000 description 10
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000003607 modifier Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- GUPXYSSGJWIURR-UHFFFAOYSA-N 3-octoxypropane-1,2-diol Chemical compound CCCCCCCCOCC(O)CO GUPXYSSGJWIURR-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- VFGRALUHHHDIQI-UHFFFAOYSA-N butyl 2-hydroxyacetate Chemical compound CCCCOC(=O)CO VFGRALUHHHDIQI-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 239000003223 protective agent Substances 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- 150000008062 acetophenones Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000012491 analyte Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 235000019504 cigarettes Nutrition 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 229960002146 guaifenesin Drugs 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000002552 multiple reaction monitoring Methods 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- LOSWWGJGSSQDKH-UHFFFAOYSA-N 3-ethoxypropane-1,2-diol Chemical compound CCOCC(O)CO LOSWWGJGSSQDKH-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- SXZYCXMUPBBULW-SKNVOMKLSA-N L-gulono-1,4-lactone Chemical compound OC[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O SXZYCXMUPBBULW-SKNVOMKLSA-N 0.000 description 1
- ARIWANIATODDMH-UHFFFAOYSA-N Lauric acid monoglyceride Natural products CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 1
- QHZLMUACJMDIAE-UHFFFAOYSA-N Palmitic acid monoglyceride Natural products CCCCCCCCCCCCCCCC(=O)OCC(O)CO QHZLMUACJMDIAE-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 125000005257 alkyl acyl group Chemical group 0.000 description 1
- YPZUZOLGGMJZJO-LQKXBSAESA-N ambroxan Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C)[C@@H]1[C@]2(C)OCC1 YPZUZOLGGMJZJO-LQKXBSAESA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000010813 internal standard method Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000005040 ion trap Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005232 molecular self-assembly Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000447 pesticide residue Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 235000019505 tobacco product Nutrition 0.000 description 1
- BJIOGJUNALELMI-ONEGZZNKSA-N trans-isoeugenol Chemical compound COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 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
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
-
- 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
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
- G01N2030/8809—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample
- G01N2030/884—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample organic compounds
Landscapes
- 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)
- Immunology (AREA)
- Pathology (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Abstract
The invention relates to application of a hydroxyl-containing compound, a matrix improver and an analysis method of flavor components in tobacco, belonging to the technical field of chemical analysis and test. The invention relates to application of a hydroxyl-containing compound in inhibiting adsorption of a gas chromatography active site, wherein the hydroxyl-containing compound is a compound with a structure shown in a formula I or a formula II, and R 1 is selected from C2-C18 alkyl; in formula II, R 2 is selected from C2-C18 alkanoyloxy or C2-C18 alkyl, n is 1 or 2. According to the application of the hydroxyl-containing compound, the compound shown in the formula I or the formula II is added into the solution to be detected, mixed and injected, the compound shown in the formula I or the formula II can rapidly fill the active sites in the gas chromatography sample inlet, the chromatographic column and the detector, and the active sites exposed in the gas flow path are alkyl inert groups, so that a new adsorption site is not formed, and the influence of the adsorption of the active sites on the detection result in the gas chromatography analysis process is reduced.
Description
Technical Field
The invention relates to an application of a hydroxyl-containing compound in inhibiting adsorption of a gas chromatography active site, a matrix improver and an analysis method of flavor components in tobacco, and belongs to the technical field of chemical analysis and test.
Background
Gas chromatography is widely used for chemical analysis and detection as a separation technical means of compounds in complex matrixes. However, due to the presence of active sites on the surface of the gas chromatography flow path (including the sample inlet, the chromatographic column and the detector), sensitive compounds adsorb or degrade at the active sites, resulting in compound loss or tailing of chromatographic peaks, with higher detection limits and more susceptible to interference. In addition, the gas phase analysis process has matrix effect, and when the matrix passes through the gas chromatography flow path, high-boiling polar impurities are easy to remain in a sample inlet, a chromatographic column or a detector to form new adsorption sites, and the response of the to-be-detected object is reduced and the peak shape is poor.
The level and mutual proportion of the flavor components in tobacco have a key effect on the style quality of tobacco leaves and cigarettes, and the flavor components are widely paid attention to by tobacco flavoring staff. The types of fragrance ingredients include aldehydes, ketones, alcohols, phenols, esters, heterocyclics, ethers, hydrocarbons, sulfides, amides, anhydrides, acetals, ketals, and the like. Most of the fragrance components contain reactive groups such as hydroxyl groups, amino groups, carbonyl groups, unsaturated bonds, heteroatoms, etc. At present, the matrix effect of gas chromatography on the aroma components is not reported, and related researches on the matrix effect are carried out in the field of pesticide residue analysis. Researches show that the matrix effect can be compensated to a certain extent by adding 3-ethoxy-1, 2-propylene glycol, L-gulonic acid-gamma-lactone, polyethylene glycol, D-sorbitol and other compounds. However, because of the strong polarity of these compounds, they require dissolution with a strong polar solvent (e.g., acetonitrile) and even the addition of a certain amount of water to aid dissolution, limiting their range of application in gas chromatographic methods. Meanwhile, as the hydroxyl groups are distributed around the compound molecules, the compounds are adsorbed on the active sites randomly after entering the gas chromatograph, although the adsorption of the sensitive compounds by the original active sites is reduced, the hydroxyl groups exposed in the gas flow path become new adsorption sites at the same time, and the protection effect on the to-be-detected objects is limited.
Disclosure of Invention
The invention aims to provide an application of a hydroxyl-containing compound in inhibiting adsorption of a gas chromatography active site, which has strong universality and can effectively inhibit adsorption of a surrogate analyte in a gas flow path.
The invention also provides a matrix improver for gas chromatographic analysis and an analysis method of flavor components in tobacco.
In order to achieve the above object, the application of the hydroxyl-containing compound in inhibiting adsorption of gas chromatography active sites adopts the following technical scheme:
use of a hydroxyl-containing compound in inhibiting adsorption of a gas chromatography active site, wherein the hydroxyl-containing compound is a compound with a structure shown in formula I or formula II;
In the formula I, R 1 is selected from C2-C18 alkyl;
in formula II, R 2 is selected from C2-C18 alkanoyloxy or C2-C18 alkyl, n is 1 or 2.
The hydroxyl-containing compound is applied to inhibiting adsorption of gas chromatography active sites, the compound shown in the formula I or the formula II is added into a solution to be detected, and is mixed and injected, the compound shown in the formula I or the formula II can rapidly fill active sites in a gas chromatography sample inlet, a chromatographic column and a detector, and alkyl inert groups are exposed in a gas flow path, so that a new adsorption site is not formed, and the influence of the adsorption of the active sites on a detection result in the gas chromatography analysis process is reduced. In addition, the molecular intermediates of the compounds of the formula I and the formula II are connected with an alcohol hydroxyl group and a nonpolar alkane chain through ether bonds or ester groups, the compound is prepared by the existing synthesis process, the raw materials are cheap and easy to obtain, the universality is strong, and the compound is applicable to polar and nonpolar solvent extraction, and can be widely used.
The compound with the structure shown in the formula I is hydroxyacetate. In formula I, R 1 is C3-C18 alkyl, R 1 may be straight-chain alkyl or branched alkyl.
Preferably, the compound having the structure shown in formula I is isooctyl glycolate.
The C2-C18 alkanoyloxy can be represented as-CO-R 3,R3, namely C1-C17 alkyl, and when the number of carbon atoms in R 3 is more than 2, the alkyl acyl can be branched or unbranched. In the formula II, when R 2 is C3-C18 alkyl, R 2 can be branched alkyl or branched alkyl.
For the compound shown in the formula II, when n is 1 and R 2 is alkyl, the compound shown in the formula II is ethylene glycol monoether; when n is 1 and R 2 is alkyl acyloxy, the compound of formula II is ethylene glycol monoester; when n is 2 and R 2 is alkyl, the compound of formula II is glycerol monoether; when n is 2 and R 2 is alkanoyloxy, the compound of formula II is monoglyceride.
Preferably, in formula II, R 2 is selected from C4-C8 linear alkyl or C9-C17 linear alkanoyloxy and n is 2.
Preferably, the compound having the structure shown in formula II is glycerol monobutyl ether, capric acid monoglyceride or stearic acid monoglyceride.
Preferably, the application comprises the steps of: and adding the hydroxyl-containing compound into the solution to be detected, uniformly mixing, and then carrying out gas chromatographic analysis. Preferably, the solution to be tested is a solution to be tested of tobacco or tobacco products.
The technical scheme adopted by the matrix protective agent for gas chromatographic analysis is as follows:
a matrix improver for gas chromatographic analysis consists of functional compound and organic solvent; the functional compound is one or two or more of compounds with a structure shown in a formula I and/or one or two or more of compounds with a structure shown in a formula II;
In the formula I, R 1 is selected from C2-C18 alkyl;
in formula II, R 2 is selected from C2-C18 alkanoyloxy or C2-C18 alkyl, n is 1 or 2.
The matrix improver for gas chromatographic analysis contains functional compound with polar group at one end and nonpolar alkyl at the other end. When entering a gas chromatography system, the functional compound performs directional molecular self-assembly on the solid surface, the polar group is adsorbed on the active site of the solid surface, and the nonpolar alkyl extends in the gas flow path. Because the alkyl is inert, the protective effect on the object to be detected is good. Meanwhile, due to the specific molecular structures of the compounds of the formula I and the formula II, the compounds have good solubility in both strong polar solvents and nonpolar solvents, and are simultaneously suitable for measuring polar and nonpolar substances to be measured.
The matrix improver for gas chromatographic analysis is suitable for analysis and detection of sensitive compounds with active groups in various complex matrixes (such as samples of tobacco leaves, smoke, essence liquid, tea leaves, fruits, vegetables, soil, water samples and the like). The active group herein means one or more of a hydroxyl group, a carbonyl group, an ester group, an amino group, an amide group, an unsaturated bond, and a hetero atom. The heteroatom is one or a combination of oxygen, sulfur, nitrogen and phosphorus.
The matrix improver for gas chromatography is suitable for analyzing and detecting the compound with the active group, and can select the functional compound with similar volatility with the compound to be detected and the organic solvent to form the matrix improver according to the chemical property of the substance to be detected and the retention time in the gas chromatography. The volatility of the functional compound in the matrix improver has strong correlation with the types, the quantity and the alkyl length of polar groups in molecules, and the volatile performance of the functional compound is controllable.
Preferably, the functional compound is one or any combination of butyl glycolate, glycerol monobutyl ether, glycerol Shan Gengmi, glycerol monooctyl ether, isooctyl glycolate, capric acid monoglyceride, lauric acid monoglyceride, palmitic acid monoglyceride and stearic acid monoglyceride. Further preferably, the functional compound is a combination of glycerol monobutyl ether, isooctyl glycolate, decanoic acid monoglyceride, and octadecanoic acid monoglyceride.
Preferably, the concentration of each functional compound in the matrix modifier is 1000-20000ppm.
Preferably, the organic solvent is selected from one or any combination of acetonitrile, methanol, ethanol, propanol, isopropanol, acetone, ethyl acetate, dichloromethane, benzene and toluene.
The method for analyzing the flavor components in the tobacco adopts the following technical scheme:
a method for analyzing flavor components in tobacco, comprising the steps of:
1) Soaking a tobacco sample in a buffer solution with pH value of 3-5, adding acetonitrile and an internal standard substance for extraction, then adding a salting-out agent, then adding dichloromethane for extraction again, separating, and taking an organic extraction solution to obtain a solution to be detected;
2) Adding the matrix improver into the solution to be tested, mixing uniformly, and then sampling and injecting into a gas chromatograph for analysis.
According to the analysis method of the aroma components in the tobacco, disclosed by the invention, the adsorption of the gas chromatography active site on the sensitive aroma components can be effectively inhibited by adding the matrix improver, so that the response value of an instrument is basically consistent no matter whether the to-be-detected object with the same concentration is in a standard solution or a tobacco matrix, and the accuracy and the reliability of the quantitative result of the aroma components are further improved.
When the quantitative analysis is carried out on the flavor components in the tobacco, when a standard curve of the compound to be analyzed is drawn, matrix improvers are added into a series of standard solutions with different analyte concentrations, the concentration of each functional compound in a system with each standard solution added with the matrix improvers is ensured to be the same, and the concentration of each corresponding functional compound in the system with the solution to be tested added with the analysis protective agent is kept consistent.
It is understood that the organic extraction solution obtained by separation after extraction is carried out again, namely the solution to be detected. In step 1), the separation is a centrifugation, and the organic extraction solution is supernatant after the centrifugation.
Preferably, in step 1), both extractions are vortex extractions.
Preferably, the buffer solution is a NaH 2PO4/H3PO4 buffer solution.
Acetonitrile has higher penetrability and is mutually soluble with water, can make the composition that awaits measuring fully leach, but can make a large amount of moisture of remaining in the organic extraction phase simultaneously, can significantly reduce the moisture content in the organic extraction phase through the secondary extraction, improves the accuracy of testing result.
Preferably, the salting-out agent is a mixed salt of sodium chloride and anhydrous magnesium sulfate. Preferably, the temperature of the system is reduced to below-18 ℃ prior to adding the salting-out agent. The temperature reduction treatment can avoid the damage of the components to be detected caused by the heat released after the mixed salt of sodium chloride and anhydrous magnesium sulfate is added into the system, and the accuracy of the detection result is affected. After adding the salting-out agent, the system is shaken, and then a second extractant is added.
Preferably, the concentration of each functional compound in the mixed system of the matrix improver and the solution to be tested is 50-2000ppm.
Preferably, the fragrance component comprises one or any combination of propenyl ethyl guaiacol, 4-methoxy cinnamaldehyde, 2-methyl-3-furfurylthiopyrazine, lauryl isovalerate, ambroxide, benzyl salicylate and citronellyl phenylacetate.
Preferably, the matrix improver is added in an amount of 1-20% of the volume of the solution to be tested.
The gas chromatograph in the present invention is an analytical test device using gas chromatography as a separation system, and examples thereof include a gas chromatography-thermal conductivity detector (GC-TCD), a gas chromatography-hydrogen flame ionization detector (GC-FID), a gas chromatography-electron capture detector (GC-ECD), a gas chromatography-flame photometric detector (GC-FPD), a gas chromatography-nitrogen-phosphorus detector (GC-NPD), a gas chromatography-mass spectrometer (GC-MSD), a gas chromatography-triple quadrupole mass spectrometer (GC-QQQ), a gas chromatography-quadrupole ion trap mass spectrometer (GC-QIT), and a gas chromatography-quadrupole time-of-flight mass spectrometer (GC-QTOF).
Drawings
FIG. 1 is a total ion flow diagram of a mixed standard solution of 7 fragrance components before and after adding a matrix improver in Experimental example 1 of the present invention, wherein a-propenyl guaifenesin, b-4-methoxy cinnamaldehyde, c-2-methyl-3-furylthiopyrazine, d-lauryl isovalerate, e-ambrox, f-benzyl salicylate, g-citronellyl phenylacetate.
Detailed Description
The technical scheme of the invention is further described below with reference to the specific embodiments.
Example 1
The matrix improver for gas chromatographic analysis of the present embodiment is composed of a functional compound and an organic solvent; the functional compound is the combination of monobutyl ether of glycerin, isooctyl glycolate, monocaprylic acid monoglyceride and stearic acid monoglyceride, and the concentration of the monobutyl ether of glycerin, isooctyl glycolate, monocaprylic acid monoglyceride and stearic acid monoglyceride in the matrix improver is 2000ppm, 10000ppm and 10000ppm respectively; the organic solvent is dichloromethane.
Example 2
The matrix improver for gas chromatographic analysis of the present embodiment is composed of a functional compound and an organic solvent; the functional compound is a combination of butyl glycolate, glycerol monooctyl ether and dodecanoic acid monoglyceride, and the concentration of the butyl glycolate, the glycerol monooctyl ether and the dodecanoic acid monoglyceride in the matrix improver is 4000ppm, 4000ppm and 20000ppm respectively; the organic solvent is methanol.
Example 3
The matrix improver for gas chromatographic analysis of the present embodiment is composed of a functional compound and an organic solvent; the functional compound is a combination of glycerol monobutyl ether, glycerol Shan Geng ether and hexadecanoic acid monoglyceride, and the concentration of the glycerol monobutyl ether, the glycerol Shan Geng ether and the hexadecanoic acid monoglyceride in the matrix improver is 4000ppm, 4000ppm and 20000ppm respectively; the organic solvent is acetone.
Example 4
The analysis method of the flavor components in the tobacco of the embodiment is to analyze and test the content of 7 flavor components such as propenyl guaifenesin, 4-methoxy cinnamaldehyde, 2-methyl-3-furfurylthiopyrazine, lauryl isovalerate, ambroxol, benzyl salicylate, citronellyl phenylacetate and the like in cut tobacco of cigarettes, and specifically comprises the following steps:
1) Preparing a series of mixed standard solutions of the to-be-detected flavor components with dichloromethane, wherein the mixed standard solutions are different in concentration, the concentration of the internal standard substances in the mixed standard solutions is guaranteed to be identical, then respectively adding a matrix improver of the embodiment 1, which is 5% of the volume of the mixed standard solutions, into the mixed standard solutions, so that the concentration of the glycerol monobutyl ether, the isooctyl glycolate, the capric acid monoglyceride and the stearic acid monoglyceride in the matrix improver are respectively 100ppm, 500ppm and 500ppm, shaking uniformly, performing GC-QQQ analysis, and then establishing a standard curve by using an internal standard method according to the concentration and the response area of the substances of the to-be-detected flavor components;
2) 1g of tobacco sample is weighed, 5mL of NaH 2PO4/H3PO4 buffer solution with pH=3 is added, and the mixture is soaked for 20min; then adding 5mL of acetonitrile extractant and an internal standard deuterated acetophenone, and performing vortex extraction for 20min at 2000 r/min; freezing at low temperature for 20min until the system temperature reaches-18 ℃, adding 5g NaCl/MgSO 4 mixed salt, shaking vigorously, adding 5mL dichloromethane, extracting for 20min again by vortex at 2000r/min, centrifuging for 3min at 8000r/min, taking supernatant to obtain a solution to be detected, adding the matrix modifier of example 1 into the solution to be detected, enabling the concentration of the glycerol monobutyl ether, isooctyl glycolate, capric acid monoglyceride and stearic acid monoglyceride in the matrix modifier to be 100ppm, 500ppm and 500ppm respectively in the mixed system, sampling and analyzing by GC-QQQ under the same instrument condition as in step 1), and calculating the content of the corresponding flavor component in the tobacco sample according to the response area of each flavor component to be detected, the internal standard substance and the standard curve.
Conditions of the GC-QQQ instrument in step 1) and step 2):
Chromatographic column: DB-5MS UI elastic quartz capillary chromatographic column (60 m x 0.25mm x 0.25 μm); sample inlet temperature: 290 ℃; programming temperature: the initial temperature is 40 ℃, after 3min, the temperature is raised to 75 ℃ at 5 ℃/min, then raised to 120 ℃ at 1 ℃, then raised to 160 ℃ at 2 ℃, then raised to 290 ℃ at 5 ℃ and kept for 10min; sample introduction without diversion and time without diversion is 1min; the spacer purge flow rate is 3mL/min; carrier gas: helium (purity 99.999%), constant flow mode, flow rate 1.5mL/min; sample injection amount: 1 mul. Electron bombardment (EI) ionization mode, ionization energy 70eV; filament current: 35 μA; ion source temperature: 280 ℃; four-stage bar temperature: 150 ℃; transmission line temperature: 280 ℃; the detection mode is as follows: multiple Reaction Monitoring (MRM) mode.
The standard curve of this example is shown in Table 1.
Table 17 fragrance ingredient standard curves
The detection results of 7 aroma components in the tobacco sample are as follows: no propenyl guaiacol, no 4-methoxy cinnamaldehyde, no 2-methyl-3-furylthiopyrazine, no lauryl isovalerate, 0.21 μg/g ambroxol, 0.69 μg/g benzyl salicylate, and no citronellyl phenylacetate.
Example 5
In the embodiment, 7 fragrance components in 7 fragrance component mixed standard solutions of propenyl ethyl guaiacol, 4-methoxy cinnamaldehyde, 2-methyl-3-furfurylthiopyrazine, lauryl isovalerate, ambroxol, benzyl salicylate, citronellyl phenylacetate and the like are analyzed and tested by adopting GC-QQ, and the specific steps are as follows:
Preparing a mixed standard solution A of 7 fragrance components to be detected by using methylene dichloride, wherein the concentration of each fragrance component in the mixed standard solution A is 0.4ppm, taking 1mL of the mixed standard solution A, adding 50 mu L of the matrix modifier of the example 1, shaking uniformly, analyzing by using GC-QQQ, and recording the response area of 7 fragrance components.
Meanwhile, 1mL of the mixed standard solution A was added with 50. Mu.L of methylene chloride, and the mixture was mixed, sampled and analyzed by GC-QQQ, and the response area of 7 aroma components was recorded.
The instrument conditions of the two GC-QQQ analyses were identical to those of example 4, and the response areas of the 7 aroma components obtained are shown in Table 2, and the chromatograms are shown in FIG. 1.
TABLE 2 area variation in response to 7 fragrance ingredients before and after the addition of matrix modifier
The results in Table 2 show that the response area of 7 fragrance components increases by a factor of 4.6 to 10.9 with the addition of the matrix modifier,
Example 6
The compensation effect of the matrix protective agent on the matrix effect is examined in the embodiment, and the specific method is as follows:
The mixed standard solution of 7 fragrance components such as propenyl ethyl guaiacol, 4-methoxy cinnamaldehyde, 2-methyl-3-furfurylthiopyrazine, lauryl isovalerate, ambroxol, benzyl salicylate, citronellyl phenylacetate and the like is prepared by adopting methylene dichloride, and the concentration of each fragrance component in the mixed standard solution is 1ppm.
Then, 50. Mu.L of the matrix improver of example 1 was added to 1mL of the mixed standard solution, and the mixture was shaken to obtain a solution A to be analyzed, and GC-QQQ analysis was performed to obtain the response area of each fragrance component to be tested, as shown in Table 3.
1G of tobacco sample is weighed, 15mL of NaH 2PO4/H3PO4 buffer solution with pH=5 is added, and the mixture is soaked for 20min; adding 5mL of acetonitrile extractant and an internal standard deuterated acetophenone, and performing vortex extraction at 2000r/min for 20min; freezing at low temperature for 20min, cooling to-18deg.C, adding 10g NaCl/MgSO 4 mixed salt, shaking vigorously, adding 15mL dichloromethane, extracting at 2000r/min for 20min, centrifuging at 8000r/min for 3min, and collecting supernatant to obtain solution to be tested. Then 1mL of the solution to be tested was transferred into a chromatographic flask, and then 50. Mu.L of the matrix improver of example 1 was added, shaken well, and analyzed by GC-QQQ. Simultaneously, another 1mL of the solution to be detected is taken and placed in a chromatographic bottle, 50 mu L of the matrix modifier of the embodiment 1 is added, 7 kinds of the above-mentioned fragrance components are added, the concentration of each fragrance component in a mixed system is ensured to be the same as that of the analysis solution A, the mixture is uniformly shaken, and GC-QQQ analysis is carried out. The response area of each sample to be measured after the standard substances of 7 flavor components are added into the sample solution is calculated, namely the response area of each flavor component to be measured in the sample solution of the tobacco sample is shown in Table 3.
The GC-QQQ conditions of the three GC-QQQ analyses in this experimental example are identical to the instrument conditions of example 4.
The ratio of the response area of each flavour material to be tested in the standard solution divided by the response area in the tobacco matrix was between 78-105% as shown in table 3.
TABLE 3 investigation of the matrix Effect of 7 fragrance components after the addition of matrix modifier
As can be seen from the data in Table 3, the response values of the apparatus are basically consistent no matter the measured substances with the same concentration are in the standard solution or the measured solution, and the matrix improver can effectively inhibit the adsorption of the gas chromatography active site and compensate the matrix effect.
Claims (6)
1. Use of a matrix improver for gas chromatographic analysis of flavour ingredients, characterised in that: the matrix improver consists of a functional compound and an organic solvent; the functional compound is a combination of glycerol monobutyl ether, isooctyl glycolate, capric acid monoglyceride and stearic acid monoglyceride; the fragrance component comprises one or any combination of propenyl ethyl guaiacol, 4-methoxy cinnamaldehyde, 2-methyl-3-furfurylthiopyrazine, lauryl isovalerate, ambroxol, benzyl salicylate and citronellyl phenylacetate.
2. The use according to claim 1, characterized in that: the concentration of each functional compound in the matrix improver is 1000-20000ppm.
3. The use according to claim 1, characterized in that: the organic solvent is selected from one or any combination of acetonitrile, methanol, ethanol, propanol, isopropanol, acetone, ethyl acetate, dichloromethane, benzene and toluene.
4. The use according to claim 1, characterized in that: the application comprises the following steps: adding the matrix improver into a solution to be tested, uniformly mixing, and then carrying out gas chromatographic analysis; the concentration of the functional compound in the system obtained after the matrix improver is added into the solution to be detected is 50-2000ppm.
5. A method for analyzing flavor components in tobacco, which is characterized by comprising the following steps: the method comprises the following steps:
1) Soaking a tobacco sample in a buffer solution with pH value of 3-5, adding acetonitrile and an internal standard substance for extraction, then adding a salting-out agent, then adding dichloromethane for extraction again, separating, and taking an organic extraction solution to obtain a solution to be detected;
2) Adding a matrix improver into the solution to be detected, uniformly mixing, and then sampling and injecting into a gas chromatograph for analysis; the matrix improver consists of a functional compound and an organic solvent; the functional compound is a combination of glycerol monobutyl ether, isooctyl glycolate, capric acid monoglyceride and stearic acid monoglyceride;
The fragrance component comprises one or any combination of propenyl ethyl guaiacol, 4-methoxy cinnamaldehyde, 2-methyl-3-furfurylthiopyrazine, lauryl isovalerate, ambroxol, benzyl salicylate and citronellyl phenylacetate.
6. The method for analyzing flavor components in tobacco according to claim 5, wherein: the added volume of the matrix improver is 1-20% of the volume of the solution to be tested.
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| 气相色谱分析农药残留的基质效应及其解决方法;贺利民;刘祥国;曾振灵;;色谱(第01期);全文 * |
| 溶剂萃取-中心切割多维色谱-质谱法测定烟草主要中性香味成分;王晔;孙文梁;苏庆德;刘百战;;烟草科技;20130720(第07期);全文 * |
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