CN117949581A - Detection method of 2,3,4, 6-tetrabenzyl-D-glucopyranose - Google Patents
Detection method of 2,3,4, 6-tetrabenzyl-D-glucopyranose Download PDFInfo
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- CN117949581A CN117949581A CN202211284957.4A CN202211284957A CN117949581A CN 117949581 A CN117949581 A CN 117949581A CN 202211284957 A CN202211284957 A CN 202211284957A CN 117949581 A CN117949581 A CN 117949581A
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- tetrabenzyl
- glucopyranose
- solution
- phosphoric acid
- liquid chromatography
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- BPMIHKHNNNNQIO-YFEREJOUSA-N (3r,4s,5r,6r)-3,4,5-tribenzyl-6-(1-hydroxy-2-phenylethyl)oxane-2,3,4,5-tetrol Chemical compound OC([C@@H]1[C@]([C@@](O)(CC=2C=CC=CC=2)[C@](O)(CC=2C=CC=CC=2)C(O)O1)(O)CC=1C=CC=CC=1)CC1=CC=CC=C1 BPMIHKHNNNNQIO-YFEREJOUSA-N 0.000 title claims abstract description 47
- 238000001514 detection method Methods 0.000 title claims abstract description 25
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000004811 liquid chromatography Methods 0.000 claims abstract description 25
- 239000000243 solution Substances 0.000 claims abstract description 24
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 15
- 239000012535 impurity Substances 0.000 claims abstract description 14
- FGDQGIKMWOAFIK-UHFFFAOYSA-N acetonitrile;phosphoric acid Chemical compound CC#N.OP(O)(O)=O FGDQGIKMWOAFIK-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000007864 aqueous solution Substances 0.000 claims abstract description 11
- 239000003814 drug Substances 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000012490 blank solution Substances 0.000 claims description 7
- 239000012488 sample solution Substances 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 6
- 239000000523 sample Substances 0.000 claims description 6
- 238000010606 normalization Methods 0.000 claims description 4
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000000926 separation method Methods 0.000 abstract description 6
- 238000004458 analytical method Methods 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- 239000013558 reference substance Substances 0.000 description 5
- FZNCGRZWXLXZSZ-CIQUZCHMSA-N Voglibose Chemical compound OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O FZNCGRZWXLXZSZ-CIQUZCHMSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 229960001729 voglibose Drugs 0.000 description 2
- 238000003556 assay Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000011003 system suitability test Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Abstract
The invention belongs to the technical field of analysis and detection, and provides a detection method of 2,3,4, 6-tetrabenzyl-D-glucopyranose, wherein liquid chromatography is adopted to detect the 2,3,4, 6-tetrabenzyl-D-glucopyranose, and phosphoric acid aqueous solution and/or phosphoric acid acetonitrile solution are adopted as mobile phases of the liquid chromatography, so that the separation effect between components can be improved, the peak type can be improved, and the content of the 2,3,4, 6-tetrabenzyl-D-glucopyranose and impurities thereof can be detected simply, accurately, quickly and reliably; can be applied to the preparation of 2,3,4, 6-tetrabenzyl-D-glucopyranose and the preparation process of medicaments, and can control the quality of the 2,3,4, 6-tetrabenzyl-D-glucopyranose.
Description
Technical Field
The invention relates to the technical field of analysis and detection, in particular to a detection method of 2,3,4, 6-tetrabenzyl-D-glucopyranose.
Background
2,3,4, 6-Tetrabenzyl-D-glucopyranose, the structure of which is shown in the following formula (I). 2,3,4, 6-tetrabenzyl-D-glucopyranose is an important intermediate for synthesizing the voglibose, and the purity and the unknown single impurity content of the compound directly influence the purity and the impurity size of subsequent products, so that the curative effect of the medicine is directly influenced. In order to enhance the quality control of 2,3,4, 6-tetrabenzyl-D-glucopyranose, development of a detection method of 2,3,4, 6-tetrabenzyl-D-glucopyranose is urgently needed, and related documents and reports of a purity detection method of 2,3,4, 6-tetrabenzyl-D-glucopyranose are not found at present.
Disclosure of Invention
The present invention aims to solve at least one of the technical problems in the prior art described above. Therefore, the invention provides a detection method of 2,3,4, 6-tetrabenzyl-D-glucopyranose, which is characterized by qualitative retention time and quantitative peak area, and can simply, accurately, quickly and reliably detect the content of 2,3,4, 6-tetrabenzyl-D-glucopyranose and unknown single impurity.
The first aspect of the invention provides a method for detecting 2,3,4, 6-tetrabenzyl-D-glucopyranose.
Specifically, the detection method of the 2,3,4, 6-tetrabenzyl-D-glucopyranose comprises the following steps:
Preparing a blank solution;
Taking a test sample to prepare a test sample solution;
Detecting the blank solution by adopting liquid chromatography to obtain a chromatogram A;
Detecting the sample solution by adopting liquid chromatography to obtain a chromatogram B;
then, after the chromatographic peak of the chromatogram A is subtracted by utilizing the chromatogram B, the purity and the impurity content of the 2,3,4, 6-tetrabenzyl-D-glucopyranose are calculated;
The mobile phase of the liquid chromatograph comprises a phosphoric acid aqueous solution and/or a phosphoric acid acetonitrile solution.
The invention adopts liquid chromatography to detect 2,3,4, 6-tetrabenzyl-D-glucopyranose, and adopts water solution of phosphoric acid and/or acetonitrile solution of phosphoric acid as mobile phase of liquid chromatography, the detection method of the invention can improve separation effect between components, can improve peak type, and can accurately detect content of 2,3,4, 6-tetrabenzyl-D-glucopyranose and unknown single impurity.
Preferably, the chromatographic column of the liquid chromatography is an octadecyl chromatographic column.
More preferably, the chromatographic column of the liquid chromatography is shimadzu WondaSil C, 18, superb (4.6 x 250mm,5 μm).
Preferably, the mobile phase is an aqueous phosphoric acid solution and an acetonitrile phosphoric acid solution.
Preferably, the volume ratio of the phosphoric acid aqueous solution to the phosphoric acid acetonitrile solution is 20-40:80-60.
More preferably, the volume ratio of the phosphoric acid aqueous solution to the phosphoric acid acetonitrile solution is 30:70.
Preferably, the mass concentration of the phosphoric acid aqueous solution is 0.01-1%.
More preferably, the phosphoric acid aqueous solution has a mass concentration of 0.1%.
Preferably, the mass concentration of the acetonitrile phosphate solution is 0.01-1%.
More preferably, the acetonitrile phosphate solution has a mass concentration of 0.1%.
Preferably, the dilution of the liquid chromatograph is acetonitrile.
Preferably, the sample injection amount of the liquid chromatograph is 5-15 mu L.
More preferably, the liquid chromatography is performed at a sample loading of 10 μl.
Preferably, the column temperature of the liquid chromatography is 25-35 ℃.
More preferably, the column temperature of the liquid chromatography is 30 ℃.
Preferably, the detector of the liquid chromatograph is an ultraviolet detector.
Preferably, the calculation uses an area normalization method.
Preferably, the detection wavelength of the liquid chromatograph is 200-220nm.
More preferably, the detection wavelength of the liquid chromatograph is 210nm.
Preferably, the conditions of the liquid chromatography further comprise a flow rate of 0.1-2mL/min.
More preferably, the conditions of the liquid chromatography further include a flow rate of 1.0mL/min.
Preferably, the liquid chromatography is run for 30-50min.
More preferably, the run time of the liquid chromatography is 40min.
Preferably, the system suitability test is further included before the test solution is detected by liquid chromatography.
Preferably, the system applicability test comprises measuring a reference substance solution, injecting the reference substance solution into a liquid chromatograph, and recording a chromatogram C.
Preferably, the theoretical plate number of the system applicability test is calculated according to the peak of 2,3,4, 6-tetrabenzyl-D-glucopyranose and is not lower than 1500, and the separation degree of a main peak and an impurity peak is not lower than 1.5.
The second aspect of the invention provides an application of the detection method of 2,3,4, 6-tetrabenzyl-D-glucopyranose.
The application of a detection method of 2,3,4, 6-tetrabenzyl-D-glucopyranose in preparing the 2,3,4, 6-tetrabenzyl-D-glucopyranose or a medicament.
Preferably, the drug is voglibose.
Compared with the prior art, the invention has the following beneficial effects:
(1) According to the invention, liquid chromatography is adopted to detect 2,3,4, 6-tetrabenzyl-D-glucopyranose, and phosphoric acid aqueous solution and/or phosphoric acid acetonitrile solution is adopted as mobile phase of the liquid chromatography, so that not only can separation effect between components be improved and peak type can be improved, but also contents of 2,3,4, 6-tetrabenzyl-D-glucopyranose and impurities thereof can be detected simply, accurately, quickly and reliably, and in the method, effective separation can be realized for the 2,3,4, 6-tetrabenzyl-D-glucopyranose and known impurities thereof;
(2) The detection method can be applied to the preparation of 2,3,4, 6-tetrabenzyl-D-glucopyranose and the preparation process of medicines, and can control the quality of the 2,3,4, 6-tetrabenzyl-D-glucopyranose.
Drawings
FIG. 1 is a graph showing the detection pattern of 2,3,4, 6-tetrabenzyl-D-glucopyranose produced in example 1;
FIG. 2 is a graph showing the detection pattern of 2,3,4, 6-tetrabenzyl-D-glucopyranose produced in example 2;
FIG. 3 is a graph showing the detection pattern of 2,3,4, 6-tetrabenzyl-D-glucopyranose produced in example 3.
Detailed Description
In order to make the technical solutions of the present invention more apparent to those skilled in the art, the following examples will be presented. It should be noted that the following examples do not limit the scope of the invention.
The starting materials, reagents or apparatus used in the following examples are all available from conventional commercial sources or may be obtained by methods known in the art unless otherwise specified.
Example 1
The detection method of the 2,3,4, 6-tetrabenzyl-D-glucopyranose comprises the following steps:
(1) Preparing a blank solution (diluent), precisely measuring 10 mu L of the diluent, injecting the diluent into a liquid chromatograph, and detecting the blank solution by adopting the liquid chromatograph to obtain a chromatogram A;
(2) Taking a proper amount of 2,3,4, 6-tetrabenzyl-D-glucopyranose working reference substance, adding a diluent to dissolve and dilute the working reference substance to prepare a solution containing about 0.5mg of 2,3,4, 6-tetrabenzyl-D-glucopyranose per 1mL, and shaking the solution uniformly to obtain a reference substance solution;
(3) Taking a proper amount of the test sample, adding a proper amount of diluent, dissolving and diluting to prepare a solution containing about 0.5mg per 1mL, and shaking uniformly to obtain a test sample solution; precisely measuring 10 mu L of the sample solution, injecting into a liquid chromatograph, and performing liquid chromatography detection to obtain a chromatogram B;
(4) Then, subtracting the chromatographic peak of the chromatogram A of the blank solution from the chromatogram B of the sample solution, and respectively calculating the purity and impurity content of the 2,3,4, 6-tetrabenzyl-D-glucopyranose according to an area normalization method;
The conditions of the liquid chromatography are as follows:
chromatographic column: a chromatographic column of shimadzu WondaSil C, superb (4.6 x 250mm,5 μm);
Sample injection amount: 10 mu L
Flow rate: 1.0mL/min
Column temperature: 30 DEG C
Detection wavelength: 210nm of
Mobile phase: phosphoric acid aqueous solution with mass concentration of 0.1 percent: acetonitrile phosphate solution with mass concentration of 0.1% = 30:70
Dilution liquid: acetonitrile
Run time: 40min
A detector: ultraviolet detector
The quantitative method comprises the following steps: the purity and impurity content of 2,3,4, 6-tetrabenzyl-D-glucopyranose were calculated by an area normalization method.
Example 2
This example and example 1 were run on different batches of 2,3,4, 6-tetrabenzyl-D-glucopyranose product, produced according to the same production specification instructions, according to the test method described above in example 1.
Example 3
This example and example 1 were run on the same manufacturing instructions to produce different batches of 2,3,4, 6-tetrabenzyl-D-glucopyranose product, as per the test method described in example 1 above.
The results of the assays of examples 1-3 are shown in FIGS. 1-3, wherein Absorbance in FIG. 1 is Absorbance and Integration Results is integration. Specific examples 1-3 the test data and calculations are shown in tables 1-3 below. The peak times of the "1-5" peaks in FIG. 1 were 3.453, 4.457, 6.083, 6.648, 19.618min, respectively.
The peak times of the "1-8" peaks in FIG. 2 were 4.388, 6.018, 6.182, 6.578, 7.173, 9.452, 9.862, 19.473min, respectively.
The peak times of the "1-11" peaks in FIG. 3 were 2.712, 2.933, 4.393, 6.015, 6.162, 6.578, 7.173, 7.467, 9.455, 9.857, 19.477min, respectively.
TABLE 1 analytical test results for example 1
TABLE 2 analytical test results for example 2
TABLE 3 analytical test results for example 3
As is apparent from the results of the above-mentioned test results in tables 1 to 3, the present invention uses liquid chromatography to test the content of 2,3,4, 6-tetrabenzyl-D-glucopyranose and impurities thereof in the preparation process of 2,3,4, 6-tetrabenzyl-D-glucopyranose, and uses phosphoric acid aqueous solution and/or phosphoric acid acetonitrile solution as mobile phase, 2,3,4, 6-tetrabenzyl-D-glucopyranose and impurities can be well separated, the degree of separation is not less than 1.5, the peak type is good, and the purities of the 2,3,4, 6-tetrabenzyl-D-glucopyranose prepared in examples 1 to 3 are 99.80%, 99.81% and 99.66%, respectively.
Claims (10)
1. The detection method of the 2,3,4, 6-tetrabenzyl-D-glucopyranose is characterized by comprising the following steps:
Preparing a blank solution;
Taking a test sample to prepare a test sample solution;
Detecting the blank solution by adopting liquid chromatography to obtain a chromatogram A;
Detecting the sample solution by adopting liquid chromatography to obtain a chromatogram B;
then, after the chromatographic peak of the chromatogram A is subtracted by utilizing the chromatogram B, the purity and the impurity content of the 2,3,4, 6-tetrabenzyl-D-glucopyranose are calculated;
The mobile phase of the liquid chromatograph comprises a phosphoric acid aqueous solution and/or a phosphoric acid acetonitrile solution.
2. The method according to claim 1, wherein the liquid chromatography column is an octadecyl column.
3. The method of claim 1, wherein the mobile phase is an aqueous phosphoric acid solution or an acetonitrile phosphoric acid solution.
4. The method according to claim 3, wherein the volume ratio of the phosphoric acid aqueous solution to the phosphoric acid acetonitrile solution is 20-40:80-60.
5. The method according to claim 1, wherein the liquid chromatography diluent is acetonitrile.
6. The method according to claim 1, wherein the column temperature of the liquid chromatograph is 25-35 ℃.
7. The method according to claim 1, wherein the detector of the liquid chromatograph is an ultraviolet detector.
8. The method of claim 1, wherein the calculating uses an area normalization method.
9. The method according to claim 1, wherein the detection wavelength of the liquid chromatograph is 200-220nm.
10. Use of the detection method of 2,3,4, 6-tetrabenzyl-D-glucopyranose according to any one of claims 1 to 9 for the preparation of said 2,3,4, 6-tetrabenzyl-D-glucopyranose or of a medicament.
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|---|---|---|---|
| CN202211284957.4A CN117949581A (en) | 2022-10-20 | 2022-10-20 | Detection method of 2,3,4, 6-tetrabenzyl-D-glucopyranose |
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| CN202211284957.4A CN117949581A (en) | 2022-10-20 | 2022-10-20 | Detection method of 2,3,4, 6-tetrabenzyl-D-glucopyranose |
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| CN202211284957.4A Pending CN117949581A (en) | 2022-10-20 | 2022-10-20 | Detection method of 2,3,4, 6-tetrabenzyl-D-glucopyranose |
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