CN112362624A - Supermolecule fluorescence analysis method for detecting alcohol perfume compounds - Google Patents
Supermolecule fluorescence analysis method for detecting alcohol perfume compounds Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 119
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 102
- 239000002304 perfume Substances 0.000 title claims abstract description 68
- 238000000034 method Methods 0.000 title claims abstract description 28
- 238000012921 fluorescence analysis Methods 0.000 title claims abstract description 16
- 238000005859 coupling reaction Methods 0.000 claims abstract description 40
- 230000008878 coupling Effects 0.000 claims abstract description 39
- 238000010168 coupling process Methods 0.000 claims abstract description 39
- 238000001514 detection method Methods 0.000 claims abstract description 30
- 239000000796 flavoring agent Substances 0.000 claims abstract description 21
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 239000000126 substance Substances 0.000 claims abstract description 11
- 235000019634 flavors Nutrition 0.000 claims abstract description 10
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 120
- 239000000243 solution Substances 0.000 claims description 61
- 241000208125 Nicotiana Species 0.000 claims description 40
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 40
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims description 39
- 239000005792 Geraniol Substances 0.000 claims description 39
- 229940113087 geraniol Drugs 0.000 claims description 39
- 230000005284 excitation Effects 0.000 claims description 25
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000012086 standard solution Substances 0.000 claims description 17
- 239000011734 sodium Substances 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 229910001868 water Inorganic materials 0.000 claims description 7
- 239000003205 fragrance Substances 0.000 claims description 5
- 239000008057 potassium phosphate buffer Substances 0.000 claims description 4
- 239000012064 sodium phosphate buffer Substances 0.000 claims description 3
- 239000012295 chemical reaction liquid Substances 0.000 claims description 2
- 238000010812 external standard method Methods 0.000 claims description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 claims description 2
- 235000011009 potassium phosphates Nutrition 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 2
- 238000003271 compound fluorescence assay Methods 0.000 claims 1
- 238000004458 analytical method Methods 0.000 abstract description 8
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000011896 sensitive detection Methods 0.000 abstract description 2
- 229910021642 ultra pure water Inorganic materials 0.000 description 15
- 239000012498 ultrapure water Substances 0.000 description 15
- 239000000523 sample Substances 0.000 description 14
- 230000008859 change Effects 0.000 description 13
- 238000011084 recovery Methods 0.000 description 11
- 238000007865 diluting Methods 0.000 description 10
- 238000004817 gas chromatography Methods 0.000 description 7
- 229940055329 tobacco leaf extract Drugs 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000004448 titration Methods 0.000 description 6
- 238000010586 diagram Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000012470 diluted sample Substances 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 239000013026 undiluted sample Substances 0.000 description 4
- -1 acyclic monoterpene alcohols Chemical class 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
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- 238000012360 testing method Methods 0.000 description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229930003651 acyclic monoterpene Natural products 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000005173 quadrupole mass spectroscopy Methods 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 235000019505 tobacco product Nutrition 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
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- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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Abstract
The invention relates to a supermolecule fluorescence analysis method for detecting alcohol flavor compounds, belonging to the technical field of flavor and flavor analysis and detection. The invention utilizes that glycoluril aromatic ring coupling compound molecules have fluorescence characteristics and have C-shaped cavities with polar derivative groups, alcohol perfume substances can form inclusion compounds due to the matching of the sizes of the cavities of the supermolecule main bodies, and meanwhile, the fluorescence intensity of the main body molecules is changed, so the series of main body molecules can be used for fluorescence qualitative, quantitative and analysis of the alcohol perfume substances. Based on the principle, the invention constructs a rapid and sensitive detection method under the conditions of normal temperature and green solvent, and realizes qualitative and quantitative trace detection of the alcohol perfume compound. The method has the advantages of strong operability, environmental protection, mild conditions, easily obtained raw materials and simple operation.
Description
Technical Field
The invention belongs to the technical field of essence and spice analysis and detection, and particularly relates to a supermolecule fluorescence analysis method for detecting alcohol spice compounds.
Background
Nerol and geraniol are acyclic monoterpene alcohols, which are main alcohol aroma components in rose essential oil, the total proportion of the alcohol aroma components is 50-80%, and the two alcohol aroma substances are colorless liquids, have sweet rose aroma, have wide application in the field of essence and aroma, and are also aroma components of reconstituted tobacco. However, the two molecules have extremely strong volatility, so that the conventional detection method is complex and the detection process is difficult to control.
There are many analytical methods for detecting alcohol perfume compounds, such as gas chromatography, gas chromatography-mass spectrometry, gas chromatography-triple quadrupole mass spectrometry, liquid chromatography-tandem mass spectrometry, multidimensional gas chromatography-mass spectrometry, and gas chromatography-fourier transform infrared spectroscopy. However, these methods still have many disadvantages, some of which require complicated pretreatment and some of which are accurate, but the analysis time is too long and is easily limited and influenced by the environment. At present, the most commonly used method for determining the alcohol perfume compounds is mainly chromatography, but the chromatography is complex in operation, time-consuming, multiple in influencing factors, difficult in condition control, expensive in price of a chromatographic instrument and daily maintenance cost and needs professional operation, so that the development of a sensitive and specific analysis method for extracting and detecting trace alcohol perfume compounds in biological and environmental samples has important significance in establishing a simple, convenient, rapid and efficient method for detecting the alcohol perfume compounds.
Disclosure of Invention
The invention aims to solve the defects of the prior art and provides a supermolecule fluorescence analysis method for detecting alcohol perfume compounds, wherein a fluorescent glycoluril aromatic ring coupling compound with a benzene ring or naphthalene ring structure side wall is utilized, the structure contains a sulfonic side chain, so that the water solubility of molecules is increased, meanwhile, the molecules have certain fluorescence performance, the molecules are in a C-shaped flexible structure, and the molecules are provided with hydrophobic cavities, so that guest molecules in a certain size range can enter the cavities. The invention utilizes the fact that alcohol perfume compounds can enter the cavity of the glycoluril aromatic ring conjugate in a green solvent to form a clathrate compound, so that the glycoluril aromatic ring conjugate generates photoinduced electron transfer and the fluorescence of the glycoluril aromatic ring conjugate is enhanced. Based on the principle, a rapid and sensitive detection system under the conditions of normal temperature and green solvent is constructed, and qualitative and quantitative trace detection of the alcohol perfume compound is realized.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
a supramolecular fluorescence analysis method for detecting alcohol perfume compounds comprises the following steps:
taking a solution containing an alcohol perfume compound to be detected as a solution to be detected; the alcohol perfume compound to be detected is at least one of nerol and geraniol;
step (2), adding glycoluril aromatic ring coupling compound into the solution to be detected to carry out inclusion reaction to form an inclusion compound;
the chemical structural formula of the glycoluril aromatic ring coupling compound is shown as (a) or (b):
wherein R is1＝(CH2)nX，n＝0～5，X＝SO3Na, COONa or NH4 +Cl-；
And (3) detecting the reaction liquid reacted in the step (2) by using a fluorescence spectrophotometer, and quantifying according to the obtained fluorescence intensity external standard method to obtain the concentration of the alcohol perfume compound to be detected.
Further, it is preferable to prepare concentration gradient alcohol-based flavor compound standard solutions, add the same amount of glycoluril aromatic ring conjugate to the solutions to perform inclusion reaction, and after the reaction, detect the fluorescence intensity of each reaction solution and the solution containing only the same amount of glycoluril aromatic ring conjugate under the same conditions but no alcohol-based flavor compound by a fluorescence spectrophotometer, which is respectively marked as I, I0To (I-I)0)/I0And drawing a standard working curve by taking the concentration of the alcohol perfume compound in the standard solution as an abscissa, and measuring the content of the alcohol perfume compound by using the curve.
Further, it is preferable that glycoluril aromatic ring coupling compound is added to the solution to be detected for inclusion reaction, wherein the concentration of the glycoluril aromatic ring coupling compound is more than or equal to 3 μmol/L, and 3 μmol/L is preferable in view of saving principle.
Further, it is preferable that the wavelength of the detection excitation light of the glycoluril aromatic ring conjugate a is 290nm when detected by a fluorescence spectrophotometer; the wavelength of detection excitation light of the glycoluril aromatic ring coupling compound b is 301nm, and the wavelength of emission light of the glycoluril aromatic ring coupling compound a is 332 nm; the emission wavelength of the glycoluril aromatic ring coupling compound b is 348 nm.
Further, it is preferable that the concentration of the alcohol perfume compound standard solution is 0.1 to 10.0. mu.M.
Further, the solvent of the solution to be detected and the solvent of the standard solution are preferably water, potassium phosphate or sodium phosphate buffer solution with the pH value of 3-9.8, ethanol or acetonitrile.
Further, it is preferable that the flavor containing the alcohol flavor compound to be detected is perfume or tobacco extract.
Further, it is preferable that the reaction time is 10min or more, preferably 10 min.
The invention also protects the application of the glycoluril aromatic ring conjugate in detecting the content of alcohol perfume compounds.
The invention also discloses a supramolecular fluorescence analysis method for detecting the alcohol perfume compounds, which comprises the following steps: preparing alcohol perfume compound standard solution with gradient concentration, adding the same amount of glycoluril aromatic ring coupling compound, reacting, detecting the fluorescence intensity of each reaction solution and the solution containing only the same amount of glycoluril aromatic ring coupling compound but no alcohol perfume compound under the same condition by a fluorescence spectrophotometer, respectively labeled as I, I0To (I-I)0)/I0Taking the concentration of the alcohol perfume compound in the standard solution as an abscissa, drawing a standard working curve, and measuring the content of the alcohol perfume compound by using the curve;
the chemical structural formula of the glycoluril aromatic ring coupling compound is shown as (a) or (b):
wherein R is1＝(CH2)nX，n＝0～5，X＝SO3Na, COONa or NH4 +Cl-；
The alcohol perfume compound is at least one of nerol and geraniol.
The fluorescent glycoluril aromatic ring conjugate used in the present invention can be identified by nuclear magnetic resonance spectroscopy (NMR), and FIG. 1 shows glycoluril aromatic ring conjugate a (R)1＝(CH2)3SO3Nuclear magnetic resonance hydrogen spectrum of Na: (1H NMR) diagram, FIG. 2 is glycoluril aromatic ring conjugate b (R)1＝(CH2)3SO3Nuclear magnetic resonance hydrogen spectrum of Na: (1H NMR) graph.
The alcohol perfume compound analyzed and detected by the invention has the following structural formula:
the chemical dose ratio of the inclusion reaction of the fluorescent glycoluril aromatic ring conjugate and the alcohol perfume compound is proved by a Job graph. FIG. 3 is a geraniol and glycoluril aromatic ring conjugate a
(R1＝(CH2)2SO3Na), FIG. 4 (R)1＝(CH2)2CO3Na) is the Job plot of geraniol and glycoluril aromatic ring conjugate b. As can be seen from the figure, the nerol, the geraniol and the glycoluril aromatic ring conjugates a and b are at the maximum value of 0.5, indicating that the inclusion ratio of the host and the guest is 1:1, so that the inclusion stoichiometric ratio of 1:1 is adopted in the analysis test and the test and calculation of the inclusion constant of the host and the guest.
The invention adopts the inclusion reaction between the fluorescent glycoluril aromatic ring conjugate and the alcohol perfume compound to cause the fluorescence change, and can be used for qualitative and quantitative analysis of the alcohol perfume compound. The used instrument is a fluorescence spectrophotometer, the range of the excitation light wavelength is selected to be 280-320nm (the optimal detection excitation light wavelength of the glycoluril aromatic ring coupling compound a is 290nm, the optimal detection excitation light wavelength of the glycoluril aromatic ring coupling compound b is 301nm), the range of the emission light wavelength is 330-370nm (the optimal emission light wavelength of the glycoluril aromatic ring coupling compound a is 332nm, the optimal emission light wavelength of the glycoluril aromatic ring coupling compound b is 348nm), and the range of the optimal excitation light wavelength is determined according to the maximum quantum yield; and (4) selecting a quartz cuvette with four-side light transmission and no fluorescence for determination.
The minimum detection limit range of the detection method for the alcohol perfume compound is 100 nM-600 nM. The linear range of the concentration of the alcohol perfume compound in the detection method is as follows: 0-15 μ M. The range of the standard recovery rate of the detection method is as follows: 95 to 105 percent.
In the invention, the tobacco extract comprises water extract of tobacco, trapped fluid and discharged fluid of membrane separation, alcohol extract of tobacco, trapped fluid and discharged fluid of membrane separation.
The glycoluril aromatic ring coupling compound adopted by the invention is obtained by coupling reaction of etherified polyglycuril and aromatic hydroquinone (or naphthaline) derivative, and the glycoluril aromatic ring coupling compound has a C-shaped cavity structure and an aromatic group capable of generating fluorescence characteristics. By means of the substituted groups of the aromatic phenols, it is possible to recognize alcohol-type fragrance substances with different binding constants. The C-shaped cavity and the polar action of the derivative group of the C-shaped cavity can be matched with alcohol perfume substances such as nerol, geraniol and the like through the cavity size to form an inclusion compound, and the content of the aroma compounds is detected through the change of the fluorescence intensity of the glycoluril aromatic ring coupling compound molecules. Meanwhile, glycoluril aromatic ring conjugate molecules have better water solubility, and can realize detection operation in water (green solvent).
Therefore, the invention initiatively uses the glycoluril aromatic ring conjugate molecules for detecting the alcohol perfume compounds, provides the supermolecule fluorescence analysis method for detecting the alcohol perfume compounds, can quickly and accurately detect the alcohol perfume compounds, has strong operability, environmental protection, mild conditions, easily obtained raw materials and simple operation, and can be applied to the fields of tobacco, essence and perfume, chemical industry, cosmetics and the like. At present, the method is not reported yet.
Compared with the prior art, the invention has the beneficial effects that:
the invention utilizes the fact that alcohol perfume compounds can form stable inclusion compounds with glycoluril aromatic ring coupling compounds, and changes the space structure of the glycoluril aromatic ring coupling compounds, thereby enhancing the fluorescence of the glycoluril aromatic ring coupling compounds and achieving the purpose of detecting the alcohol perfume compounds. The detection system has the characteristics of normal-temperature operation, simplicity, convenience, sensitivity and rapidness. The operation is in aqueous solution, and the environment is protected. Wherein the minimum detection limit for alcohol fragrance compounds is: nerol is 270nM geraniol is 167 nM. The trace qualitative and quantitative detection of the alcohol perfume compounds is realized, the application of a fluorescence spectrophotometry in the field of analysis and detection is expanded, and the method has important significance for the quality control of tobacco and tobacco products.
Drawings
FIG. 1 is a glycoluril aromatic ring conjugate a (R)1＝(CH2)3SO3Nuclear magnetic resonance hydrogen spectrum of Na: (1H NMR，D2O) diagram;
FIG. 2 is a glycoluril aromatic ring conjugate b (R)1＝(CH2)3SO3Nuclear magnetic resonance hydrogen spectrum of Na: (1H NMR,D2O) diagram;
FIG. 3 is a geraniol and glycoluril aromatic ring conjugate a (R)1＝(CH2)2SO3Na) Job plot;
FIG. 4 shows geraniol and glycoluril aromatic ring conjugate b (R)1＝(CH2)2COONa) curve of Job;
FIG. 5 is a geraniol titration glycoluril aromatic ring conjugate a (R)1＝(CH2)3NH4 +Cl-) Fluorescence spectrum of (aqueous solution);
FIG. 6 is a fluorescence spectrum (R) of a geraniol titration glycoluril aromatic ring conjugate b1＝(CH2)3SO3Na) (aqueous solution);
FIG. 7 is a citronellol titration glycoluril aromatic ring conjugate b (R)1＝(CH2)2COONa) (aqueous solution);
FIG. 8 is a titration of geraniol with glycoluril aromatic ring conjugate a (R)1＝(CH2)1NH4 +Cl-) Fluorescence linear range diagram (aqueous solution);
FIG. 9 is a schematic diagram of nerol titrating glycoluril aromatic ring conjugate a (R)1＝(CH2)3SO3Na) fluorescence linear range plot (aqueous solution).
Detailed Description
The present invention will be described in further detail with reference to examples.
It will be appreciated by those skilled in the art that the following examples are illustrative of the invention only and should not be taken as limiting the scope of the invention. The examples do not specify particular techniques or conditions, and are performed according to the techniques or conditions described in the literature in the art or according to the product specifications. The materials or equipment used are not indicated by manufacturers, and all are conventional products available by purchase.
(1) Determining that the optimal fluorescence excitation wavelength of the glycoluril aromatic ring conjugate a is 290nm and the emission wavelength is 325 nm; the optimal fluorescence excitation wavelength of the glycoluril aromatic ring conjugate b is 301nm, and the emission wavelength is 340 nm.
Selecting a plurality of different excitation wavelengths for scanning, recording a fluorescence emission peak with a constant peak position according to the characteristic that the fluorescence emission wavelength does not change along with the change of the excitation wavelength, then scanning at the emission wavelength, and recording the maximum peak wavelength as the optimal fluorescence excitation wavelength. Finally, the optimal fluorescence excitation wavelength of the glycoluril aromatic ring conjugate a is 290nm, and the emission wavelength is 320 nm; the optimal fluorescence excitation wavelength of the glycoluril aromatic ring conjugate b is 301nm, and the emission wavelength is 340 nm;
(2) determination of binding constant (Ks value) of alcohol fragrance compound and glycoluril aromatic ring conjugate to form clathrate, it was determined that alcohol fragrance compound and glycoluril aromatic ring conjugate can form clathrate:
the binding capacity between the glycoluril aromatic ring conjugate and the geraniol is measured by adopting a fluorescence titration method, the glycoluril aromatic ring conjugate is prepared into a solution with the concentration of 3 mu M by using ultrapure water, the change value of the fluorescence of the glycoluril aromatic ring conjugate, which is gradually increased from 0 to 50 mu M, is respectively and sequentially recorded, experimental data are processed by using Microsoft Office Excel 2016, and the average value is represented by +/-standard deviation (S.D.). The fitting of the spectral data titration was performed on the website "http:// supra molecular. The Ks value of the clathrate glycoluril aromatic ring conjugate @ alcohol perfume compound is obtained.
(3) Determination of the linear range:
a. preparing the glycoluril aromatic ring conjugate a into a solution of 3 mu M by using ultrapure water, and respectively and sequentially recording the change of the fluorescence of the glycoluril aromatic ring conjugate a when the concentration of the geraniol is gradually increased from 0.01-10 mu M, wherein the result shows that the change of the fluorescence of a in the range presents a linear range, and the linear equation is that y is 0.04956x +0.00195, R is 0.04956x +0.001952The results showed good linearity at 0.99849.
b. The glycoluril aromatic ring conjugate b is prepared into a 3 mu M solution by using ultrapure water, and the change of the fluorescence of the glycoluril aromatic ring conjugate b is gradually increased from 0.01 to 10 mu M respectively and sequentially recorded, and the result shows that the change of the fluorescence of the glycoluril aromatic ring conjugate b in the range presents a linear range, the linear equation is that y is 0.18148x +0.08809, and R2 is 0.99634, and the result shows that the linearity is good.
c. Preparing the glycoluril aromatic ring conjugate a into a solution of 3 mu M by using ultrapure water, and respectively and sequentially recording the change condition of the nerol concentration which is gradually increased from 0.01 to 10 mu M to the fluorescence of the glycoluril aromatic ring conjugate a, wherein the fluorescence change of a in the range shows a linear range, and the linear equation is that y is 0.08245x +0.01523, R is 0.08245x +0.015232The results showed good linearity at 0.9981.
d. Preparing the glycoluril aromatic ring conjugate b into a solution of 3 mu M by using ultrapure water, and respectively and sequentially recording the change condition of the nerol concentration which is gradually increased from 0.01 to 10 mu M to the fluorescence of the glycoluril aromatic ring conjugate b, wherein the fluorescence change of the glycoluril aromatic ring conjugate b in the range shows a linear range, and the linear equation is that y is 0.07278x +0.04442, R is 0.07278x +0.044422The results showed good linearity at 0.99681.
(4) Determination of detection limits:
repeating the operation in the step (3) at least three times, obtaining a linear correlation coefficient which is more than or equal to 0.99, and taking the slope of the linear range with the best correlation. Separately determining I0(initial solution of glycoluril aromatic ring conjugate without geraniol addition) 14 times, and the standard deviation Σ I was taken0According to the formula LOD ═ 3 Σ I0(iv)/slope, wherein the detection limit of the geraniol/glycoluril aromatic ring conjugate a is 449nM (S/N ═ 3), the detection limit of the geraniol/glycoluril aromatic ring conjugate b is 167nM (S/N ═ 3), the detection limit of the nerol/glycoluril aromatic ring conjugate a is 270nM (S/N ═ 3), and the detection limit of the nerol/glycoluril aromatic ring conjugate b is 416nM (S/N ═ 3)
Example 1:
(1) and taking ultrapure water, and adding geraniol to the concentration of 0.200 mu M to obtain a sample to be detected.
(2) The glycoluril aromatic ring conjugate a was prepared into a 3. mu.M solution with ultrapure water, and the fluorescence emission intensity thereof under excitation light of 290nm was measured.
(3) Adding undiluted sample to be tested into the glycoluril aromatic ring conjugate a solution, measuring the fluorescence intensity, and if the fluorescence intensity exceeds the linear range, diluting the concentration of the sample to be tested to ensure that the measured fluorescence intensity is in the linear range of the concentration. And reading the fluorescence intensity reading of the diluted sample to be detected, and calculating according to a concentration linear equation or a concentration linear graph to obtain the geraniol concentration. The samples to be tested were taken 3 portions each and run in parallel. The detection results show that the concentration of the geraniol is as follows: 0.204 μ M, the average spiked recovery rate of geraniol detected by glycoluril aromatic ring conjugate a was: 102.18%, relative standard deviation (RSD%) 2.1.
Example 2:
(1) and (3) adding nerol into ethanol until the concentration of the nerol is 0.750 mu M to obtain a sample to be detected.
(2) The glycoluril aromatic ring conjugate b was prepared into a 3. mu.M solution with ethanol, and the fluorescence emission intensity thereof under excitation light of 301nm was measured.
(3) Adding an undiluted sample to be detected into the glycoluril aromatic ring coupling compound b solution, reacting for 10min, determining the fluorescence intensity, and if the fluorescence intensity exceeds a linear range, diluting the concentration of the sample to be detected to enable the determined fluorescence intensity to be in the linear range of the concentration. And reading the fluorescence intensity reading of the diluted sample to be detected, and calculating according to a concentration linear equation or a concentration linear graph to obtain the nerol concentration. The samples to be tested were taken 3 portions each and run in parallel. The concentration of nerol is determined by detection as follows: the average spiked recovery rate of geraniol detected by glycoluril aromatic ring conjugate b is 0.748 mu M: 99.67%, relative standard deviation (RSD%) 3.77.
Example 3:
(1) and taking ultrapure water, and adding geraniol to the concentration of 0.500 mu M to obtain a sample to be detected.
(2) The glycoluril aromatic ring conjugate b was prepared in a 5. mu.M solution with ultrapure water, and the fluorescence emission intensity thereof under excitation light of 301nm was measured.
(3) Adding an undiluted sample to be detected into the glycoluril aromatic ring coupling compound b solution, reacting for 10min, determining the fluorescence intensity, and if the fluorescence intensity exceeds a linear range, diluting the concentration of the sample to be detected to enable the determined fluorescence intensity to be in the linear range of the concentration. And reading the fluorescence intensity reading of the diluted sample to be detected, and calculating according to a concentration linear equation or a concentration linear graph to obtain the geraniol concentration. The samples to be tested were taken 3 portions each and run in parallel.
Preparing standard solutions of alcohol perfume compounds with gradient of 0.1, 0.2, 0.5, 1, 2, 5, 10.0 μ M, adding the same amount of glycoluril aromatic ring conjugate (with addition of 5 μ M) to perform inclusion reaction, detecting fluorescence intensity of each reaction solution and solution containing only the same amount (5 μ M) of glycoluril aromatic ring conjugate without alcohol perfume compounds under the same conditions with a fluorescence spectrophotometer, respectively, and respectively marking as I, I0To (I-I)0)/I0And drawing a standard working curve by taking the concentration of the alcohol perfume compound in the standard solution as an abscissa, and measuring the content of the alcohol perfume compound by using the curve.
The detection results show that the concentration of the geraniol is as follows: 0.475. mu.M, the average spiked recovery rate of geraniol detected by glycoluril aromatic ring conjugate b was: 105.02%, the relative standard deviation (RSD%) was 3.67.
Example 4:
(1) and adding nerol into ethanol until the concentration of the nerol is 0.100 mu M to obtain a sample to be detected.
(2) The glycoluril aromatic ring conjugate a is prepared into a 10 mu M solution by using ethanol, and the fluorescence emission intensity of the glycoluril aromatic ring conjugate a under 290nm excitation light is detected.
Preparing standard solutions of alcohol perfume compounds with gradient of 0.1, 0.2, 0.5, 1, 2, 5, 10.0 μ M, adding the same amount of glycoluril aromatic ring conjugate (10 μ M), respectively, performing inclusion reaction, detecting fluorescence intensity of each reaction solution and solution containing only the same amount (10 μ M) of glycoluril aromatic ring conjugate without alcohol perfume compounds under the same conditions with a fluorescence spectrophotometer, respectively, and respectively labeled as I, I0To (I-I)0)/I0And drawing a standard working curve by taking the concentration of the alcohol perfume compound in the standard solution as an abscissa, and measuring the content of the alcohol perfume compound by using the curve.
(3) Adding an undiluted sample to be detected into the glycoluril aromatic ring conjugate a solution, reacting for 20min, determining the fluorescence intensity, and if the fluorescence intensity exceeds a linear range, diluting the concentration of the sample to be detected to enable the determined fluorescence intensity to be in the linear range of the concentration. And reading the fluorescence intensity reading of the diluted sample to be detected, and calculating according to a concentration linear equation or a concentration linear graph to obtain the nerol concentration. The samples to be tested were taken 3 portions each and run in parallel. The concentration of nerol is determined by detection as follows: 0.0994 μ M, the average spiked recovery rate of geraniol detected by glycoluril aromatic ring conjugate a was: 99.4% with a relative standard deviation (RSD%) of 4.21.
Example 5:
(1) taking tobacco leaf extract (provided by tobacco industry Limited liability company in Yunnan) as a sample to be detected.
(2) The glycoluril aromatic ring conjugate a was prepared into a 3. mu.M solution with ultrapure water, and the fluorescence emission intensity thereof under excitation light of 290nm was measured.
(3) Adding undiluted tobacco leaf extract into the glycoluril aromatic ring conjugate a solution, reacting for 15min, measuring fluorescence intensity, and diluting the concentration of the tobacco extract if the fluorescence intensity exceeds the linear range to make the measured fluorescence intensity in the linear range of concentration. And reading the fluorescence intensity reading of the diluted tobacco extract, and calculating according to a concentration linear equation or a concentration linear graph to obtain the concentration of the alcohol flavor compound. The samples to be tested were taken 3 portions each and run in parallel. The geraniol concentration in the tobacco leaf extracting solution is 0.1383 mu M, and the average recovery rate of the geraniol in the tobacco leaf extracting solution is as follows compared with the result detected by a gas chromatography/mass spectrometer: 97.33%, relative standard deviation (RSD%) 2.90.
Example 6:
(1) taking tobacco stem extracting solution (provided by tobacco industry Limited liability company in Yunnan, and the solvent is water) as a sample to be detected.
(2) The glycoluril aromatic ring conjugate b was dissolved in ultrapure water at 3. mu.M, and the fluorescence emission intensity under excitation light of 301nm was measured.
(3) Adding undiluted tobacco leaf extract into the glycoluril aromatic ring coupling compound b solution, reacting for 10min, measuring fluorescence intensity, and diluting the concentration of the tobacco extract if the fluorescence intensity exceeds the linear range to make the measured fluorescence intensity in the linear range of concentration. And reading the fluorescence intensity reading of the diluted tobacco extract, and calculating according to a concentration linear equation or a concentration linear graph to obtain the concentration of the alcohol flavor compound. The samples to be tested were taken 3 portions each and run in parallel. The geraniol concentration in the tobacco leaf extracting solution is 0.0534 mu M, and the average recovery rate of the geraniol in the tobacco leaf extracting solution is as follows compared with the result detected by a gas chromatography/mass spectrometer: 98.15% with a relative standard deviation (RSD%) of 3.74.
Example 7:
(1) taking tobacco stem extract (provided by Limited liability company of tobacco industry in Yunnan, and the solvent is potassium phosphate buffer solution with pH of 7.5) as a sample to be tested.
(2) The glycoluril aromatic ring conjugate b was dissolved in ultrapure water at 3. mu.M, and the fluorescence emission intensity under excitation light of 301nm was measured.
(3) Adding undiluted tobacco leaf extract into the glycoluril aromatic ring coupling compound b solution, reacting for 10min, measuring fluorescence intensity, and diluting the concentration of the tobacco extract if the fluorescence intensity exceeds the linear range to make the measured fluorescence intensity in the linear range of concentration. And reading the fluorescence intensity reading of the diluted tobacco extract, and calculating according to a concentration linear equation or a concentration linear graph to obtain the concentration of the alcohol flavor compound. The samples to be tested were taken 3 portions each and run in parallel. The geraniol concentration in the tobacco leaf extracting solution is 0.0621 mu M, and the average recovery rate is as follows compared with the result detected by a gas chromatography/mass spectrometer: 99.23% and a relative standard deviation (RSD%) of 2.81.
Example 8:
(1) taking tobacco stem extract (provided by tobacco industry Limited liability company in Yunnan, and the solvent is potassium phosphate buffer solution with pH of 3) as a sample to be detected.
(2) The glycoluril aromatic ring conjugate b was dissolved in ultrapure water at 3. mu.M, and the fluorescence emission intensity under excitation light of 301nm was measured.
(3) Adding undiluted tobacco leaf extract into the glycoluril aromatic ring coupling compound b solution, reacting for 10min, measuring fluorescence intensity, and diluting the concentration of the tobacco extract if the fluorescence intensity exceeds the linear range to make the measured fluorescence intensity in the linear range of concentration. And reading the fluorescence intensity reading of the diluted tobacco extract, and calculating according to a concentration linear equation or a concentration linear graph to obtain the concentration of the alcohol flavor compound. The samples to be tested were taken 3 portions each and run in parallel. The geraniol concentration in the tobacco leaf extracting solution is 0.0482 mu M, and the average recovery rate is as follows compared with the result detected by a gas chromatography/mass spectrometer: 98.66%, relative standard deviation (RSD%) 3.25.
Example 9:
(1) taking a tobacco stem extracting solution (provided by Limited liability company of tobacco industry in Yunnan, and the solvent is a sodium phosphate buffer solution with the pH value of 9.8) as a sample to be detected.
(2) The glycoluril aromatic ring conjugate b was dissolved in ultrapure water at 3. mu.M, and the fluorescence emission intensity under excitation light of 301nm was measured.
(3) Adding undiluted tobacco leaf extract into the glycoluril aromatic ring coupling compound b solution, reacting for 10min, measuring fluorescence intensity, and diluting the concentration of the tobacco extract if the fluorescence intensity exceeds the linear range to make the measured fluorescence intensity in the linear range of concentration. And reading the fluorescence intensity reading of the diluted tobacco extract, and calculating according to a concentration linear equation or a concentration linear graph to obtain the concentration of the alcohol flavor compound. The samples to be tested were taken 3 portions each and run in parallel. The geraniol concentration in the tobacco leaf extracting solution is 0.0552 mu M, and the average recovery rate of the geraniol in the tobacco leaf extracting solution is obtained by comparing the result with the result detected by a gas chromatography/mass spectrometer: 98.72% with a relative standard deviation (RSD%) of 2.95.
Example 10:
(1) taking tobacco stem extracting solution (provided by tobacco industry Limited liability company in Yunnan, and acetonitrile is used as a solvent) as a sample to be detected.
(2) The glycoluril aromatic ring conjugate b was dissolved in ultrapure water at 3. mu.M, and the fluorescence emission intensity under excitation light of 301nm was measured.
(3) Adding undiluted tobacco leaf extract into the glycoluril aromatic ring coupling compound b solution, reacting for 10min, measuring fluorescence intensity, and diluting the concentration of the tobacco extract if the fluorescence intensity exceeds the linear range to make the measured fluorescence intensity in the linear range of concentration. And reading the fluorescence intensity reading of the diluted tobacco extract, and calculating according to a concentration linear equation or a concentration linear graph to obtain the concentration of the alcohol flavor compound. The samples to be tested were taken 3 portions each and run in parallel. The geraniol concentration in the tobacco leaf extracting solution is 0.0597 mu M, and the average recovery rate is as follows compared with the result detected by a gas chromatography/mass spectrometer: 99.35%, relative standard deviation (RSD%) 3.41.
The foregoing shows and describes the general principles, essential features, and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are described in the specification and illustrated only to illustrate the principle of the present invention, but that various changes and modifications may be made therein without departing from the spirit and scope of the present invention, which fall within the scope of the invention as claimed. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (10)
1. A supramolecular fluorescence analysis method for detecting alcohol perfume compounds is characterized by comprising the following steps:
taking a solution containing an alcohol perfume compound to be detected as a solution to be detected; the alcohol perfume compound to be detected is at least one of nerol and geraniol;
step (2), adding glycoluril aromatic ring coupling compound into the solution to be detected to carry out inclusion reaction to form an inclusion compound;
the chemical structural formula of the glycoluril aromatic ring coupling compound is shown as (a) or (b):
wherein R is1=(CH2)nX，n=0~5，X=SO3Na, COONa or NH4 +Cl-；
And (3) detecting the reaction liquid reacted in the step (2) by using a fluorescence spectrophotometer, and quantifying according to the obtained fluorescence intensity external standard method to obtain the concentration of the alcohol perfume compound to be detected.
2. The method of claim 1A supermolecule fluorescence analysis method for detecting alcohol perfume compounds is characterized in that alcohol perfume compound standard solutions with concentration gradients are prepared, glycoluril aromatic ring conjugates with the same amount are respectively added into the alcohol perfume compound standard solutions to carry out inclusion reaction, after the reaction, fluorescence intensities of each reaction solution and solutions which only contain the same amount of glycoluril aromatic ring conjugates and do not contain the alcohol perfume compounds under the same conditions are respectively detected by a fluorescence spectrophotometer and are respectively and correspondingly marked as I, I0To (I-I)0）/I0And drawing a standard working curve by taking the concentration of the alcohol perfume compound in the standard solution as an abscissa, and measuring the content of the alcohol perfume compound by using the curve.
3. The supramolecular fluorescence analysis method for detecting alcohol perfume compounds as claimed in claim 1 or 2, characterized in that glycoluril aromatic ring coupling compound is added to the solution to be detected for inclusion reaction, wherein the concentration of the glycoluril aromatic ring coupling compound is more than or equal to 3 μmol/L.
4. The supramolecular fluorescence analysis method for detecting alcohol flavor compounds according to claim 1 or 2, wherein the wavelength of the detection excitation light of glycoluril aromatic ring conjugate a is 290nm when detected by a fluorescence spectrophotometer; the wavelength of detection excitation light of the glycoluril aromatic ring coupling compound b is 301nm, and the wavelength of emission light of the glycoluril aromatic ring coupling compound a is 332 nm; the emission wavelength of the glycoluril aromatic ring coupling compound b is 348 nm.
5. The supramolecular fluorescence assay method for detecting alcohol flavor compounds as claimed in claim 1 or 2, wherein the concentration of the alcohol flavor compound standard solution is 0.1-10.0 μ M.
6. The supramolecular fluorescence analysis method for detecting alcohol flavor compounds as claimed in claim 2, wherein the solvent of the solution to be detected and the standard solution is water, potassium phosphate or sodium phosphate buffer solution with pH = 3-9.8, ethanol or acetonitrile.
7. The supramolecular fluorescence analysis method for detecting alcohol flavor compounds as claimed in claim 1 or 2, wherein the flavor containing the alcohol flavor compound to be detected is perfume or tobacco extract.
8. The supramolecular fluorescence analysis method for detecting alcohol flavor compounds according to claim 1 or 2, wherein the reaction time is not less than 10 min.
9. Use of the glycoluril aromatic ring conjugate of claim 1 for detecting the content of alcohol fragrance compounds.
10. A supramolecular fluorescence analysis method for detecting alcohol perfume compounds is characterized by comprising the following steps: preparing alcohol perfume compound standard solution with gradient concentration, adding the same amount of glycoluril aromatic ring coupling compound, reacting, detecting the fluorescence intensity of each reaction solution and the solution containing only the same amount of glycoluril aromatic ring coupling compound but no alcohol perfume compound under the same condition by a fluorescence spectrophotometer, respectively labeled as I, I0To (I-I)0）/I0Taking the concentration of the alcohol perfume compound in the standard solution as an abscissa, drawing a standard working curve, and measuring the content of the alcohol perfume compound by using the curve;
the chemical structural formula of the glycoluril aromatic ring coupling compound is shown as (a) or (b):
wherein R is1=(CH2)nX，n=0~5，X=SO3Na, COONa or NH4 +Cl-；
The alcohol perfume compound is at least one of nerol and geraniol.
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