CN113203822B - Application of compound, matrix effect compensator and analysis method of aroma components in plant extract - Google Patents
Application of compound, matrix effect compensator and analysis method of aroma components in plant extract Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 67
- 230000000694 effects Effects 0.000 title claims abstract description 55
- 239000011159 matrix material Substances 0.000 title claims abstract description 48
- 238000004458 analytical method Methods 0.000 title claims abstract description 30
- 239000000419 plant extract Substances 0.000 title claims abstract description 15
- 238000004817 gas chromatography Methods 0.000 claims abstract description 28
- 239000000126 substance Substances 0.000 claims abstract description 11
- 239000000243 solution Substances 0.000 claims description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 26
- 239000003205 fragrance Substances 0.000 claims description 24
- XCBBNTFYSLADTO-UHFFFAOYSA-N 2,3-Octanedione Chemical compound CCCCCC(=O)C(C)=O XCBBNTFYSLADTO-UHFFFAOYSA-N 0.000 claims description 18
- 238000001212 derivatisation Methods 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 claims description 14
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 claims description 14
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 14
- 238000000605 extraction Methods 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 9
- 239000000796 flavoring agent Substances 0.000 claims description 9
- 235000019634 flavors Nutrition 0.000 claims description 9
- IKYDDBGYKFPTGF-UHFFFAOYSA-N octyl 3-oxobutanoate Chemical compound CCCCCCCCOC(=O)CC(C)=O IKYDDBGYKFPTGF-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- 239000012483 derivatization solution Substances 0.000 claims description 8
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims description 7
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 claims description 7
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 7
- YOMSJEATGXXYPX-UHFFFAOYSA-N 2-methoxy-4-vinylphenol Chemical compound COC1=CC(C=C)=CC=C1O YOMSJEATGXXYPX-UHFFFAOYSA-N 0.000 claims description 7
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 7
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 claims description 7
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 claims description 7
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 claims description 7
- 229930016911 cinnamic acid Natural products 0.000 claims description 7
- 235000013985 cinnamic acid Nutrition 0.000 claims description 7
- 235000000484 citronellol Nutrition 0.000 claims description 7
- 229960000304 folic acid Drugs 0.000 claims description 7
- 235000019152 folic acid Nutrition 0.000 claims description 7
- 239000011724 folic acid Substances 0.000 claims description 7
- URZVPVBICGXGEG-UHFFFAOYSA-N methyl 2-oxooctadecanoate Chemical compound CCCCCCCCCCCCCCCCC(=O)C(=O)OC URZVPVBICGXGEG-UHFFFAOYSA-N 0.000 claims description 7
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 7
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 7
- 229960004889 salicylic acid Drugs 0.000 claims description 7
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 claims description 7
- FQKGSCOHCDSKAC-UHFFFAOYSA-N 4-[3-cyanopropyl(dimethoxy)silyl]butanenitrile Chemical compound N#CCCC[Si](OC)(CCCC#N)OC FQKGSCOHCDSKAC-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims description 6
- 239000005770 Eugenol Substances 0.000 claims description 6
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-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
- 229960002217 eugenol Drugs 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 238000005185 salting out Methods 0.000 claims description 6
- IJALWSVNUBBQRA-UHFFFAOYSA-N 4-Isopropyl-3-methylphenol Chemical compound CC(C)C1=CC=C(O)C=C1C IJALWSVNUBBQRA-UHFFFAOYSA-N 0.000 claims description 5
- 238000005070 sampling Methods 0.000 claims description 4
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 238000005303 weighing Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 20
- 238000001179 sorption measurement Methods 0.000 abstract description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 10
- 238000001514 detection method Methods 0.000 abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 abstract description 7
- 230000002401 inhibitory effect Effects 0.000 abstract description 5
- 239000007787 solid Substances 0.000 abstract description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract description 2
- 239000012491 analyte Substances 0.000 abstract description 2
- 238000005232 molecular self-assembly Methods 0.000 abstract 1
- 239000007789 gas Substances 0.000 description 20
- 239000002253 acid Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 239000012086 standard solution Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000004615 ingredient Substances 0.000 description 9
- 150000002989 phenols Chemical class 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- XCOBLONWWXQEBS-KPKJPENVSA-N N,O-bis(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)O\C(C(F)(F)F)=N\[Si](C)(C)C XCOBLONWWXQEBS-KPKJPENVSA-N 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 238000002444 silanisation Methods 0.000 description 7
- 238000006884 silylation reaction Methods 0.000 description 7
- -1 unsaturated bond Chemical group 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 235000020765 fenugreek extract Nutrition 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- ZMAYRLMREZOVLE-UHFFFAOYSA-N 2-ethenyl-6-methoxyphenol Chemical compound COC1=CC=CC(C=C)=C1O ZMAYRLMREZOVLE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005844 Thymol Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- MWVFCEVNXHTDNF-UHFFFAOYSA-N hexane-2,3-dione Chemical compound CCCC(=O)C(C)=O MWVFCEVNXHTDNF-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002552 multiple reaction monitoring Methods 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 229960000790 thymol Drugs 0.000 description 2
- NIONDZDPPYHYKY-SNAWJCMRSA-N (2E)-hexenoic acid Chemical compound CCC\C=C\C(O)=O NIONDZDPPYHYKY-SNAWJCMRSA-N 0.000 description 1
- RZYHXKLKJRGJGP-UHFFFAOYSA-N 2,2,2-trifluoro-n,n-bis(trimethylsilyl)acetamide Chemical group C[Si](C)(C)N([Si](C)(C)C)C(=O)C(F)(F)F RZYHXKLKJRGJGP-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
- 241000196324 Embryophyta Species 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
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 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
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 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
- NIONDZDPPYHYKY-UHFFFAOYSA-N Z-hexenoic acid Natural products CCCC=CC(O)=O NIONDZDPPYHYKY-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical group CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 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
- 238000009835 boiling Methods 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000007705 chemical test Methods 0.000 description 1
- CLCYRHCSVWOLHG-UHFFFAOYSA-N decyl 3-oxobutanoate Chemical compound CCCCCCCCCCOC(=O)CC(C)=O CLCYRHCSVWOLHG-UHFFFAOYSA-N 0.000 description 1
- KCHWKBCUPLJWJA-UHFFFAOYSA-N dodecyl 3-oxobutanoate Chemical compound CCCCCCCCCCCCOC(=O)CC(C)=O KCHWKBCUPLJWJA-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000015203 fruit juice Nutrition 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
- QNZLAXONNWOLJY-UHFFFAOYSA-N hexyl 3-oxobutanoate Chemical compound CCCCCCOC(=O)CC(C)=O QNZLAXONNWOLJY-UHFFFAOYSA-N 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
- 238000010813 internal standard method Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000005040 ion trap Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VWRCAQBZONAKSC-UHFFFAOYSA-N methyl 2-oxohexadecanoate Chemical compound CCCCCCCCCCCCCCC(=O)C(=O)OC VWRCAQBZONAKSC-UHFFFAOYSA-N 0.000 description 1
- DTBSXIIDKUOHEN-UHFFFAOYSA-N methyl 3-oxotetradecanoate Chemical compound CCCCCCCCCCCC(=O)CC(=O)OC DTBSXIIDKUOHEN-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 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
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 229910000077 silane Inorganic materials 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
- 229960002920 sorbitol Drugs 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000004885 tandem mass spectrometry Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229940098465 tincture Drugs 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
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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)
- Immunology (AREA)
- Pathology (AREA)
- Fats And Perfumes (AREA)
- Sampling And Sample Adjustment (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Abstract
The invention relates to application of a compound, a matrix effect compensator and an analysis method of aroma components in plant extracts, and belongs to the technical field of chemical analysis and detection. The compound with the structure shown in the formula I is applied to inhibiting adsorption of gas chromatography active sites, wherein m is 0 or 1, and n is 0 or 1; r 1 is methyl or methoxy; r 2 is C2-C18 alkoxy or C2-C18 alkyl when R 1 is methyl and R 2 is C2-C18 alkyl when R 1 is methoxy. In the application of the invention, one end of the molecule of the compound of the formula I is a polar group, and the other end is nonpolar alkane. After the compound of the formula I enters a gas chromatography system, directional molecular self-assembly is carried out on the solid surface, polar groups are adsorbed on active sites on the solid surface, nonpolar alkyl is stretched in a gas phase flow path, and a novel adsorption site is not formed due to the inertness of the alkyl, so that a good protection effect on an analyte can be formed.
Description
Technical Field
The invention relates to application of a compound shown in a formula I in inhibiting adsorption of a gas chromatography active site, a matrix effect compensator for gas chromatography analysis and an analysis method of fragrance components in a plant extract, and belongs to the technical field of chemical test analysis.
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 acid, alcohol and phenol compounds are important fragrant components, endow the product with special taste and fragrance, and have important effects on improving the quality and style of the product. At present, common analysis methods of acids, alcohols and phenols are that Gas Chromatography (GC), gas chromatography-mass spectrometry (GC-MS) or gas chromatography-tandem mass spectrometry (GC-MS/MS) are adopted for detection after silanization. Because the molecule contains active groups such as carbonyl, unsaturated bond, hetero atom and the like, the acid, alcohol and phenol silanization products still have stronger activity. Therefore, when the instrument using gas chromatography as a separation system is used for detecting acid, alcohol and phenol silanization products, the strong adsorption effect still exists.
Researches report 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 when analyzing pesticide residues. Since hydroxyl groups on these compound molecules react with a silylation reagent, they cannot be used for measuring acids, alcohols and phenols by the silylation method.
Disclosure of Invention
The invention aims to provide an application of a compound in inhibiting adsorption of gas chromatography active sites, which can reduce adsorption of acid, alcohol and phenol compounds by gas chromatography when the acid, alcohol and phenol compounds are measured by a silanization method.
The invention also provides a matrix effect compensator for gas chromatography and an analysis method of the aroma components in the plant extract.
In order to achieve the above object, the application of the compound of the present invention in inhibiting adsorption of gas chromatography active sites adopts the following technical scheme:
use of a compound having a structure according to formula I:
In the formula I, m is 0 or 1, and n is 0 or 1; r 1 is methyl or methoxy; r 2 is C2-C18 alkoxy or C2-C18 alkyl when R 1 is methyl and R 2 is C2-C18 alkyl when R 1 is methoxy.
The application of the compound with the structure shown in the formula I in inhibiting the adsorption of the gas chromatography active site is that the compound with the structure shown in the formula I is added into a solution to be detected, mixed uniformly and then injected, wherein one end of the molecule of the compound with the formula I is a polar group (carbonyl or ester group), and the other end of the molecule of the compound with the formula I is nonpolar alkane. After the compound of the formula I enters a gas chromatography system, self-assembly of oriented molecules is carried out on the surface of the solid, polar groups are adsorbed on active sites on the surface of the solid, and nonpolar alkyl groups are stretched in a gas phase flow path. Since the alkyl group is inert, no new adsorption site is formed, and good protection effect on the analyte can be formed. Particularly, when the polar groups are two carbonyl groups which are connected or separated, a five-membered or six-membered ring is formed between the polar groups and the active site of the solid surface, namely the adsorption effect between the polar groups and the active site is stronger, so that the protection effect on the to-be-detected object is further enhanced. And because the polar group is protected by methyl, active hydrogen atoms which react with the silylation reagent do not exist in the molecule, the application of the invention is suitable for substrate effect compensation of acid, alcohol and phenol compounds measured by a silylation method.
In formula I, R 2 can be a linear alkoxy group or a branched alkoxy group or a linear alkyl group or a branched alkyl group. When R 1 is methoxy, R 2 may be a straight chain alkyl group or an alkyl group having a branched chain.
Preferably, m is 1, n is 0, and the structure of the compound shown in formula I is specifically:
In the formula II, when R 1 is methyl and R 2 is alkyl, the compound in the formula II is a diketone compound.
In the formula I, when m is 0, the structure of the compound in the formula I is specifically as follows:
in the formula III, when R 1 is methyl and R 2 is alkoxy, the compound in the formula III is alkyl acetate; when R 1 is methoxy and R 2 is alkyl, the compound of formula III is methyl alkanoate.
In the formula I, when m is 1, the structure of the compound in the formula I is specifically as follows:
In the formula IV, n is 1, R 1 is methoxy, and R 2 is alkyl, the compound in the formula IV is 3-oxo acid methyl ester; when n is 0, R 1 is methoxy and R 2 is alkyl, the compound of formula IV is methyl 2-oxoalkanoate; when n=1, R 1 is methyl, R 2 is alkoxy, the compound of formula IV is acetoacetate.
In the formula I, when n is 0, the structure of the compound in the formula I is specifically as follows:
preferably, the compound of formula I is ethyl acetoacetate, 2, 3-octanedione, n-octyl acetoacetate, methyl 3-oxotetradecanoate or methyl 2-oxooctadecanoate.
Preferably, the application comprises the steps of: and adding the compound shown in the formula I into the solution to be tested, uniformly mixing, and then carrying out gas chromatographic analysis. The compound shown in the formula I is added into a mixed system obtained after the solution to be detected, and the concentration of the compound shown in the formula I is 50-2000ppm.
Preferably, the solution to be measured is a solution to be measured of plant tincture, a solution to be measured of extractum, a solution to be measured of fruit juice or a solution to be measured of finished essence liquid.
The matrix effect compensator for gas chromatographic analysis adopts the following technical scheme:
A matrix effect compensator for gas chromatography consists of functional compound and organic solvent; the functional compound is selected from one or two or more compounds with a structure shown in a formula I:
In the formula I, m is 0 or 1, and n is 0 or 1; r 1 is methyl or methoxy; r 2 is C2-C18 alkoxy or C2-C18 alkyl when R 1 is methyl and R 2 is C2-C18 alkyl when R 1 is methoxy.
The matrix effect compensator for gas chromatography provided by the invention can be used for rapidly filling active sites in a gas chromatography sample inlet, a chromatographic column and a detector along with the solution to be detected after entering the chromatographic system, and the active sites are exposed in a gas flow path and are alkyl inert groups, so that new adsorption sites can not be formed, and the influence of active site adsorption on a detection result in the gas chromatography analysis process is reduced. In particular, the functional compound in the matrix effect compensator does not react with acids, alcohols, phenolic compounds and silylation reagents, and is particularly suitable for matrix effect compensation of acids, alcohols and phenolic compounds measured by a silylation method. Meanwhile, the specific molecular structure of the compound in the formula I ensures that the compound has good solubility in a strong polar solvent and a nonpolar solvent, and further the matrix effect compensator is suitable for the determination of polar and nonpolar to-be-detected substances.
The matrix effect compensator for gas chromatography is suitable for the 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 effect compensator for gas chromatography is particularly suitable for analyzing compounds with similar volatility as the functional compounds in the matrix effect compensator when analyzing and detecting the compounds with the active groups, so that the to-be-analyzed substances and the functional compounds have close retention time in the gas chromatography, the to-be-analyzed substances can be better protected, and the adsorption of the to-be-analyzed substances on the active sites of the gas chromatography can be reduced. 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 comprises a compound of the structure shown in formula II.
Preferably, the organic solvent is selected from one or any combination of acetonitrile, acetone, ethyl acetate, dichloromethane, benzene and toluene.
Preferably, the concentration of each compound having the structure of formula I in the matrix effect compensator is 1000-20000ppm.
Preferably, the functional compound is a combination of ethyl acetoacetate, 2, 3-octanedione, n-octyl acetoacetate, methyl 3-oxotetradecanoate, methyl 2-oxooctadecanoate.
The method for analyzing the aroma components in the plant extract adopts the following technical scheme:
An analytical method of aroma components in a plant extract, comprising the steps of: weighing a plant extract sample with certain mass, adding an internal standard, a salting-out agent and an extracting agent, extracting and separating to obtain an extraction solution, adding a derivatization reagent into the extraction solution for derivatization treatment to obtain a derivatization solution, adding the matrix effect compensating agent into the derivatization solution, uniformly mixing, and then sampling and injecting into a gas chromatograph for analysis; the fragrance component comprises one or any combination of an acid compound, an alcohol compound and a phenol compound.
The analysis method of the aroma components in the plant extract can effectively inhibit the adsorption of the gas chromatography active site on the sensitive aroma components, improve the accuracy of the quantitative result of the aroma components in the plant extract, and ensure the accurate and reliable quantitative result of the plant extract acid, alcohol and phenol substances by protecting the polar groups of the functional compounds in the matrix effect compensator by methyl and not having active hydrogen atoms which react with the silylation reagent in the molecules.
The salting-out agent is preferably sodium chloride. Preferably, when the salting-out agent is added, the salting-out agent is added into water to be dissolved to obtain saline solution, and then the saline solution is added into the system.
The extractant is preferably dichloromethane. The extraction is preferably a vortex extraction. The salting-out agent is favorable for dispersing the sample and can also improve the extraction rate of the fragrance components. The separation is preferably a centrifugation.
The derivatization treatment is preferably a silane derivatization treatment. Preferably, the derivatizing agent is a silylating agent. The silylating agent is preferably bis (trimethylsilyl) trifluoroacetamide (abbreviated as BSTFA).
Preferably, the concentration of the compound of the structure shown in formula I in the mixed system of the matrix effect compensator and the derivative liquid is 50-2000ppm.
Preferably, the matrix effect compensator is added in a volume of 1-20% of the volume of the derivative liquid.
Preferably, the acid compound comprises one or a combination of folic acid, salicylic acid and cinnamic acid. The alcohol compound comprises one or a combination of leaf alcohol, tetrahydrofurfuryl alcohol and citronellol. The phenolic compounds include p-vinylguaiacol and/or p-thymol.
The gas chromatograph in the present invention is an analytical test device using gas chromatography as a separation system, and may be, for example, 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), or a gas chromatography-quadrupole time-of-flight mass spectrometer (GC-QTOF).
Detailed Description
The technical scheme of the invention is further described below with reference to the specific embodiments.
Example 1
The matrix effect compensator for gas phase analysis of the present example is composed of a functional compound and an organic solvent, the functional compound is a combination of ethyl acetoacetate, 2, 3-octanedione, n-octyl acetoacetate, methyl 3-oxotetradecanoate, methyl 2-oxooctadecanoate, and the concentrations of ethyl acetoacetate, 2, 3-octanedione, n-octyl acetoacetate, methyl 3-oxotetradecanoate, methyl 2-oxooctadecanoate in the matrix effect compensator are 20000ppm, 4000ppm, and 10000ppm, respectively, in order; the organic solvent is dichloromethane.
Example 2
The matrix effect compensator for gas phase analysis of the present example is composed of a functional compound and an organic solvent, wherein the functional compound is 2, 3-hexanedione, 2, 3-octanedione, n-octyl acetoacetate, and dodecyl acetoacetate, and the concentrations in the matrix effect compensator are 10000ppm, and 10000ppm, respectively; the organic solvent is acetone.
Example 3
The matrix effect compensator for gas phase analysis of the present embodiment is composed of a functional compound and an organic solvent, wherein the functional compound is ethyl acetoacetate, n-hexyl acetoacetate, n-decyl acetoacetate, methyl 2-oxohexadecanoate, and the concentrations in the matrix effect compensator are 20000ppm, 4000ppm and 10000ppm, respectively; the organic solvent is ethyl acetate.
Example 4
The analysis method of the aroma components in the embodiment is to analyze and test the content of 9 aroma components such as folic acid, salicylic acid, cinnamic acid, leaf alcohol, tetrahydrofurfuryl alcohol, citronellol, eugenol, vinylguaiacol, thymol and the like in the fenugreek extract, and specifically comprises the following steps:
1) Preparing a series of mixed standard solutions of the flavor components to be detected with methylene dichloride, wherein the mixed standard solutions of the flavor components to be detected with different concentrations are prepared, the concentrations of the internal standard substances in the mixed standard solutions are guaranteed to be identical, then a derivatization reagent BSTFA is added into each mixed standard solution respectively, water bath derivatization is carried out, the obtained derivatization solution is placed to room temperature, and then a matrix effect compensator of the embodiment 1 with the volume of 10% of the derivatization solution is added, so that the concentrations of ethyl acetoacetate, 2, 3-octanedione, n-octyl acetoacetate, 3-oxo-methyl tetradecanoate and 2-oxo-methyl octadecanoate in the mixed system are respectively 2000ppm, 400ppm and 1000ppm in sequence, shaking is carried out uniformly, GC-QQQ analysis is carried out, and then a standard curve is established by using an internal standard method according to the concentrations of the flavor components to be detected and the response area of the derivatization;
2) Weighing 200mg of fenugreek extract sample, adding an internal standard substance, 10mL of sodium chloride aqueous solution and 10mL of dichloromethane, performing vortex extraction for 10min at 2000r/min, centrifuging for 3min at 8000r/min, taking supernatant to obtain an extraction solution, performing derivatization treatment on the extraction solution, wherein the derivatization treatment method is the same as that of the mixed standard solution in the step 1), placing the obtained derivatization solution at room temperature, adding a matrix effect compensator of the embodiment 1 into the derivatization solution, so that the concentration of ethyl acetoacetate, 2, 3-octanedione, n-octyl acetoacetate, 3-oxo-tetradecanoic acid methyl ester and 2-oxo-octadecanoic acid methyl ester in the mixed system is respectively 2000ppm, 400ppm and 1000ppm, sampling into GC-QQQ, analyzing under the same instrument condition as that of the step 1), and calculating the content of corresponding flavor components in the fenugreek extract sample according to the response area of each flavor component to be measured, the internal standard substance and the standard curve.
Instrument conditions for analysis of GC-QQQ 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 ℃, the temperature is kept for 3min, then the temperature is increased to 210 ℃ at 3 ℃/min, and then the temperature is increased to 290 ℃ at 5 ℃ and the temperature is 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 internal standard used in this example was trans-2-hexenoic acid.
The standard curve of this example is shown in Table 1.
TABLE 19 standard curves for acid alcohol phenol silylated products
The detection results of 9 acid alcohol phenol fragrance components in the fenugreek extract sample are as follows: the detection of the fragrant folic acid is not detected, the salicylic acid is 1.3 mug/g, the cinnamic acid is 1.7 mug/g, the leaf alcohol is not detected, the tetrahydrofurfuryl alcohol is not detected, the citronellol is not detected, the eugenol is 4.2 mug/g, the p-vinylguaiacol is 2.9 mug/g, and the p-thymol is 0.6 mug/g.
Example 5
In the embodiment, the mixed standard solution of 9 kinds of acid, alcohol and phenol flavor components such as folic acid, salicylic acid, cinnamic acid, leaf alcohol, tetrahydrofurfuryl alcohol, citronellol, eugenol, vinylguaiacol, thymol and the like is subjected to derivatization treatment by adopting BSTFA as a silanization reagent, and the derivatization product is analyzed and measured by adopting GC-QQ, and the specific steps are as follows:
Preparing a mixed standard solution A of 9 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 500 mu L of the mixed standard solution into a derivative bottle, adding 50 mu L of BSTFA, carrying out water bath at 60 ℃ for 1h, after the derivative solution is cooled to room temperature, adding 55 mu L of matrix effect compensator of example 1, shaking uniformly, analyzing by using GC-QQQ, and recording the response area of the 9 fragrance component derivatives.
Meanwhile, 500 mu L of mixed standard solution A is taken and placed in a derivative bottle, 50 mu L of BSTFA is added, water bath is carried out at 60 ℃ for 1h, after the derivative liquid is cooled to room temperature, 55 mu L of dichloromethane is added, the mixture is uniformly mixed, then the mixture is sampled and analyzed by GC-QQ, and the response area of the derivatives of 9 fragrance components is recorded.
The analytical conditions of the two GC-QQQ analyses were identical to those of example 4, and the response areas of the resulting derivatizations of 9 fragrance components are shown in Table 2.
TABLE 2 response variation of 9 acid alcohol phenol silylated products before and after addition of additives
From the data in Table 2, it can be seen that the response area of the 9 fragrance ingredient silylated products increases by a factor of 3.3-11.3 with the addition of the additive.
Example 6
The embodiment examines the compensation effect of the matrix effect compensator on the matrix effect, and the specific method is as follows:
Preparing a mixed standard solution of 9 fragrance components such as folic acid, salicylic acid, cinnamic acid, leaf alcohol, tetrahydrofurfuryl alcohol, citronellol, eugenol, p-vinylguaiacol, p-thymol and the like by using methylene dichloride, wherein the concentration of each fragrance component in the mixed standard solution is 1ppm;
Transferring 500. Mu.L of the mixed standard solution into a derivatization bottle, adding 50. Mu.L of BSTFA, carrying out water bath at 60 ℃ for 1h, cooling to room temperature, adding 55. Mu.L of matrix effect compensator of example 1, shaking uniformly to obtain a solution A to be analyzed, and carrying out GC-QQQ analysis to obtain the response area of each fragrance ingredient derivatization product, wherein the response area is shown in Table 3.
200Mg of fenugreek extract sample is weighed, 10mL of sodium chloride aqueous solution and 10mL of dichloromethane are added, vortex extraction is carried out for 10min at 2000r/min, centrifugation is carried out for 3min at 8000r/min, and supernatant fluid is taken to obtain an extraction solution. Then transferring 500 mu L of the extraction solution into a derivative bottle, adding 50 mu L of BSTFA, carrying out water bath at 60 ℃ for 1h, and cooling to room temperature to obtain a sample derivative solution; 200. Mu.L of the sample derived solution was added to 20. Mu.L of the matrix effect compensator of example 1, shaken well, and sampled into GC-QQQ for analysis. Simultaneously, another 200 mu L of sample derivative solution is removed, 20 mu L of matrix effect compensator of the example 1 is added, 9 kinds of fragrance ingredient silanization products are added, the concentration of each fragrance ingredient silanization product in a mixed system is ensured to be equal to that of the solution A to be analyzed, shaking is carried out, and sampling is carried out for GC-QQQ analysis. The response area of each of the fragrance ingredient silylated products after addition of the fragrance ingredient silylated products to the derivative liquid, i.e., the response area of each of the fragrance ingredient silylated products in the sample derivative liquid, was calculated and 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 of the silylated products of the fragrance ingredients in the derived liquid obtained by mixing the standard solutions divided by the response area in the derived liquid obtained by extracting the solutions from the samples was between 84-111%, as shown in Table 3.
TABLE 3 matrix Effect investigation of 9 fragrance ingredient silanized products with additives
The data in Table 3 show that the instrument response values of the silanized products of the fragrance components with the same concentration are basically consistent whether in the derivative liquid of the standard solution or the derivative liquid of the extract solution of the fenugreek extract, and the matrix effect compensator can effectively inhibit the adsorption of the gas chromatography active site and compensate the matrix effect.
Claims (7)
1. The use of a matrix effect compensator in gas chromatography analysis of flavour components, characterised in that: the matrix effect compensator consists of a functional compound and an organic solvent; the functional compound is selected from the group consisting of ethyl acetoacetate, 2, 3-octanedione, n-octyl acetoacetate, methyl 3-oxo-tetradecanoate, and methyl 2-oxo-octadecanoate; the fragrance component comprises one or any combination of folic acid, salicylic acid, cinnamic acid, leaf alcohol, tetrahydrofurfuryl alcohol, citronellol, eugenol, p-vinylguaiacol and p-thymol.
2. The use according to claim 1, characterized in that: the organic solvent is selected from one or any combination of acetonitrile, acetone, ethyl acetate, methylene dichloride, benzene and toluene.
3. The use according to claim 1, characterized in that: the concentration of each component in the functional compound in the matrix effect compensator is 1000-20000ppm.
4. The use according to claim 1, characterized in that: uniformly mixing the matrix effect compensator and the solution to be measured, and then carrying out gas chromatographic analysis; the concentration of the functional compound in a mixed system obtained by uniformly mixing the matrix effect compensator and the solution to be measured is 50-2000ppm.
5. A method for analyzing aroma components in a plant extract is characterized by comprising the following steps: the method comprises the following steps: weighing a plant extract sample with a certain mass, adding an internal standard substance, a salting-out agent and an extracting agent, extracting and separating to obtain an extraction solution, adding a derivatization reagent into the extraction solution for derivatization treatment to obtain a derivatization solution, adding a matrix effect compensating agent into the derivatization solution, uniformly mixing, and then sampling and injecting into a gas chromatograph for analysis; the matrix effect compensator consists of a functional compound and an organic solvent; the functional compound is selected from the group consisting of ethyl acetoacetate, 2, 3-octanedione, n-octyl acetoacetate, methyl 3-oxo-tetradecanoate, and methyl 2-oxo-octadecanoate;
The fragrance component comprises one or any combination of folic acid, salicylic acid, cinnamic acid, leaf alcohol, tetrahydrofurfuryl alcohol, citronellol, eugenol, p-vinylguaiacol and p-thymol.
6. The method for analyzing flavor components in a plant extract according to claim 5, wherein: the derivatizing agent is a silylating agent.
7. The method for analyzing flavor components in a plant extract according to claim 6, wherein: the addition volume of the matrix effect compensator is 1-20% of the volume of the derivative liquid.
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