CN112697933A - Method for measuring content of hydroxypropyl tetrahydropyrane triol and diastereoisomer ratio thereof - Google Patents
Method for measuring content of hydroxypropyl tetrahydropyrane triol and diastereoisomer ratio thereof Download PDFInfo
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Abstract
The invention relates to a method for measuring the content of hydroxypropyl tetrahydropyrane triol and the proportion of diastereoisomers thereof, which is characterized by comprising the following steps: A. respectively preparing a blank solution, a reference solution and a sample solution to be detected; B. and C, injecting the blank solution, the reference solution and the sample solution to be detected prepared in the step A into a liquid chromatograph, and setting chromatographic conditions as follows: the chromatographic column is an amide bonded phase chromatographic column, 4.6 multiplied by 250mm, 5 mu m; the sample injection volume is 10 mul; the flow rate is 0.9-1.0 ml/min; the column temperature is 25-30 ℃; the temperature of the evaporation chamber and the drift tube is 40-50 ℃; the gas flow rate is 1.6 ml/min; mobile phase: the mobile phase A is methanol, and the mobile phase B is acetonitrile; and recording the chromatogram. The method has the advantages of simple operation, low detection limit of the hydroxypropyl tetrahydropyran triol, good linearity in a linear range, high correlation coefficient, capability of separating the hydroxypropyl tetrahydropyran triol diastereoisomer, detection of the proportion of the hydroxypropyl tetrahydropyran triol diastereoisomer and the like.
Description
Technical Field
The invention relates to the field of analysis of daily chemicals, in particular to a method for measuring the content of hydroxypropyl tetrahydropyran triol by using a high performance liquid chromatography-Evaporative Light Scattering Detector (ELSD) and separating and measuring the diastereomer ratio of the hydroxypropyl tetrahydropyran triol.
Background
Hydroxypropyl tetrahydropyrane triol (CAS number 439685-79-7), also known as boscalid, is a synthetic xylose derivative chemically synthesized by man, and according to published papers and patents, hydroxypropyl tetrahydropyrane triol can promote the synthesis of glycosaminoglycan and proteoglycan, help the epidermis to be tightly connected with the dermis and maintain the elasticity of the dermis; can promote the synthesis of collagen; can promote the regeneration of fibroblast growth factor, thus having stronger anti-aging and skin repairing effects. The structure of the hydroxypropyl tetrahydropyrane triol has a stereochemical structure in which a hydroxyl group on a 7-position chiral carbon atom coexists as a pair of diastereomers.
At present, no reported detection method can be used for determining the content of the hydroxypropyl tetrahydropyrane triol and simultaneously separating and determining the ratio of diastereoisomers.
Patent CN111189800A provides a method for determining the content concentration of hydroxypropyl tetrahydropyran triol by using a refractive index test, but the detection method belongs to indirect detection and is easy to cause false positive results; also, the sensitivity and accuracy of the detection method is not described in this patent. In order to solve the problems, the invention aims to provide a high-performance liquid detection method for directly measuring the content of the hydroxypropyl tetrahydropyrane triol and separating the diastereoisomer of the hydroxypropyl tetrahydropyrane triol, and the sensitivity and the accuracy of the method are ensured by using the quantification of a reference substance.
According to Alexandre Cavezza, Christophe boule, Amerlie Gu é guiniat, Patrick Pichaud, Simon Trouille, Louis Ricard, Maria Dalko-Csib, Bioorganic & Medicinal Chemistry Letters, 2009, DOI: 10.1016/j.bmcl.2008.12.037, the stereochemistry of the hydroxyl group at the chiral carbon atom at position 7 in the hydroxypropyl tetrahydropyrane triol structure has an effect on promoting glycosaminoglycan synthesis, and different diastereomer ratios result in different activity levels. The activity of hydroxypropyl tetrahydropyran triol with the diastereomer ratio of 70/30 is much higher than that of 50/50. With the patent protection for hydroxypropyl tetrahydropyran triol synthesis technology coming to the end of 2020, many samples of domestic hydroxypropyl tetrahydropyran triol have appeared on the market. In order to evaluate the quality of a hydroxypropyl tetrahydropyrane triol sample, a detection method which can efficiently and accurately detect the content of hydroxypropyl tetrahydropyrane triol and can determine the proportion of diastereoisomers is urgently needed to be developed.
Disclosure of Invention
The invention aims to solve the technical problem of providing a method for measuring the content of hydroxypropyl tetrahydropyrane triol and the diastereoisomer ratio thereof by using high performance liquid chromatography-ELSD.
In order to solve the technical problems, the invention adopts the following technical scheme: a method for measuring the content of hydroxypropyl tetrahydropyrane triol and the diastereoisomer ratio thereof is characterized by comprising the following steps:
A. respectively preparing a blank solution, a reference substance solution and a sample solution to be detected, wherein the blank solution is purified water, and the reference substance solution is a hydroxypropyl tetrahydropyrane triol reference substance solution; the sample solution to be detected is a solution with different concentrations prepared by a hydroxypropyl tetrahydropyrane triol raw material;
B. and C, injecting the blank solution, the reference solution and the sample solution to be detected prepared in the step A into a liquid chromatograph, and setting chromatographic conditions as follows: the chromatographic column is an amide bonded phase chromatographic column, 4.6 multiplied by 250mm, 5 mu m; the sample injection volume is 10 mul; the flow rate is 0.9-1.0 ml/min; the column temperature is 25-30 ℃; the detector is ELSD; the temperature of the evaporation chamber is 40-50 ℃; the temperature of the drift tube is 40-50 ℃; the gas flow rate is 1.6 ml/min; mobile phase: the mobile phase A is methanol, and the mobile phase B is acetonitrile; the elution program was set up as follows: at 0 minute, the methanol concentration is 0%, and the acetonitrile concentration is 100%; at 20 minutes, the concentration of methanol is 20 percent, and the concentration of acetonitrile is 80 percent; at 20.1 minutes, the concentration of methanol is 0 percent, and the concentration of acetonitrile is 100 percent; at 29 minutes, the concentration of methanol is 0 and the concentration of acetonitrile is 100 percent; and recording the chromatogram.
The amide bonded phase chromatographic column is XAmide, 4.6 multiplied by 250mm, 5 mu m. Purchased from Zhejiang Hua spectral New technology, Inc.
The methanol concentration and the acetonitrile concentration are both volume concentrations.
The detection method provided by the invention is used for detecting the hydroxypropyl tetrahydropyrane triol raw material sample, so that the content of the hydroxypropyl tetrahydropyrane triol can be detected, two diastereomers in the hydroxypropyl tetrahydropyrane triol raw material sample can be simultaneously detected, the proportion of the two diastereomers can be detected, and the quality of the raw material can be better evaluated. The method of the invention also has the characteristics of green solvent and no pollution.
The invention adopts an amide bonded phase chromatographic column and is matched with a specific chromatographic condition, the peak appearance is good, the ultimate detection concentration of the hydroxypropyl tetrahydropyrane triol is 27.041 mug/ml, and the ultimate detection concentration is low. The linear regression equation of the detection method is Y =1.9262X-2.1439, r =0.9986, the linear range is 169.596 mu g/ml-1695.95 mu g/ml, and the linearity is good. The separation degree of the hydroxypropyl tetrahydropyrane triol diastereoisomer is more than 1.5, and the detection requirement can be met.
In conclusion, the method has the beneficial effects of simple operation, low detection limit of the hydroxypropyl tetrahydropyran triol, good linearity in a linear range, high correlation coefficient, capability of separating the hydroxypropyl tetrahydropyran triol diastereoisomers, detection of the proportion of the hydroxypropyl tetrahydropyran triol diastereoisomers and the like.
Drawings
FIG. 1 is a blank solution (pure water) chromatogram;
FIG. 2 is a chromatogram of a hydroxypropyl tetrahydropyran triol control solution;
FIG. 3 is a chromatogram of a detection limit solution;
FIG. 4 is a quantitation limit solution chromatogram;
FIG. 5 is a graph of a linear fit regression equation;
FIG. 6 is a chromatogram of a solution of a sample to be tested from manufacturer of EXAMPLE III A;
FIG. 7 is a chromatogram of a solution of a sample to be tested from manufacturer B of example III;
FIG. 8 is a chromatogram of a sample solution to be tested from the third manufacturer in example C.
Detailed Description
The invention is further illustrated by the following specific examples. It should be understood that: the examples of the present invention are provided for illustration only and not for limitation of the present invention. The technical scheme obtained by simply improving the invention or equivalently replacing the conventional means or components on the basis of the technical scheme of the invention belongs to the protection scope of the invention.
The instruments and reagents adopted in the embodiment of the invention are as follows:
1. high performance liquid chromatography 1260; agilent;
2. analytical balance, MS 204S/Z; a Mettler;
3. chromatography column, XAmide (4.6 x 250mm, 5 μm); chinese staff;
4. a hydroxypropyl tetrahydropyrane triol reference substance, the content of which is more than or equal to 98 percent; target molecular Corp;
5. acetonitrile, chromatographic grade;
6. methanol, chromatographic grade;
the reagents or instruments used are conventional products available from regular distributors, not indicated by the manufacturer.
Detailed Description
Example 1: the detection method of the invention has detection limit and quantitative limit
Chromatographic conditions
A chromatographic column: XAmide (4.6 x 250mm, 5 μm), zhejiang hua spectral innovative science and technology limited;
sample introduction volume: 10 mu l of the mixture; flow rate: 1.0 ml/min; column temperature: 25 ℃;
a detector: ELSD; temperature of the evaporation chamber: 40 ℃; temperature of the drift tube: 40 ℃; gas flow rate: 1.6 ml/min;
mobile phase: mobile phase a-methanol, mobile phase B-acetonitrile, elution program settings are shown in table 1.
TABLE 1 mobile phase gradiometer
The percentages in table 1 are volume percentages.
2. Preparation of the solution
(1) Blank solution: pure water is used as a blank solution;
(2) preparing a reference substance solution: weighing 0.4g (accurate to 0.0001g) of hydroxypropyl tetrahydropyran triol reference substance into a 25ml volumetric flask, adding pure water to dissolve, fixing the volume to scale, and uniformly mixing to obtain a hydroxypropyl tetrahydropyran triol reference substance solution;
(3) according to the S/N ratio of the quantification limit of more than or equal to 10 and the S/N ratio of the detection limit of more than or equal to 3, the hydroxypropyl tetrahydropyrane triol reference solution is diluted and measured according to the chromatographic conditions of the embodiment, and the corresponding chromatogram is shown in FIG. 3 (detection limit) and FIG. 4 (quantification limit). The signal-to-noise ratio was automatically calculated by software, and the experimental results are shown in table 2.
TABLE 2 measurement results of detection limit and quantification limit of hydroxypropyl tetrahydropyran triol
Example 2 Linear relationship of the detection method of the invention
1 preparation of the solution
(1) Blank solution: pure water is used as a blank solution;
(2) preparing a reference substance solution: weighing 0.4g (accurate to 0.0001g) of hydroxypropyl tetrahydropyran triol reference substance into a 25ml volumetric flask, adding pure water to dissolve, fixing the volume to scale, and uniformly mixing to obtain a hydroxypropyl tetrahydropyran triol solution;
(3) preparing a standard curve series reference substance solution: precisely transferring the hydroxypropyl tetrahydropyrane triol reference substance solutions of item (2) into 10ml volumetric flasks of 0.1ml, 0.2ml, 0.4ml, 0.8ml and 1.0ml respectively, diluting with pure water, fixing the volume to the scale, and mixing uniformly to obtain reference substance solutions;
(4) the determination method comprises the following steps: according to the determination of the chromatographic conditions of example 1, a blank solution, a control solution and a sample solution to be tested are injected respectively, and linear regression is carried out by taking a concentration logarithm value as an abscissa and a peak area logarithm value as an ordinate, as shown in fig. 5, wherein the linear regression equation is Y =1.9262X-2.1439, r =0.9986, and the linear range is 169.596 μ g/ml-1695.95 μ g/ml. The experimental data are shown in table 3.
TABLE 3 Linear measurement of hydroxypropyl tetrahydropyran triol control solution
Example 3: determination of content and isomer ratio of unknown samples from different manufacturers
1. Preparing a solution:
(1) blank solution: pure water is used as a blank solution;
(2) control solutions and standard curves: weighing 0.4g (accurate to 0.0001g) of hydroxypropyl tetrahydropyran triol reference substance into a 25ml volumetric flask, adding pure water to dissolve, fixing the volume to scale, and uniformly mixing to obtain a hydroxypropyl tetrahydropyran triol solution;
(3) preparing a standard curve series reference substance solution: precisely transferring the hydroxypropyl tetrahydropyrane triol reference substance solutions of item (2) into 10ml volumetric flasks of 0.1ml, 0.2ml, 0.4ml, 0.8ml and 1.0ml respectively, diluting with pure water, fixing the volume to the scale, and mixing uniformly to obtain reference substance solutions;
(4) preparing a sample solution to be detected: weighing 0.1g (accurate to 0.0001g) of sample to be measured in a 100ml volumetric flask, dissolving with pure water, fixing the volume to scale, and mixing uniformly to obtain a sample solution to be measured, wherein if the peak area logarithm value exceeds the highest value of the example 2, the sample can be diluted properly, and if the peak area logarithm value is lower than the lowest value of the example 2, the sample weighing amount can be increased properly.
(5) And (3) determination: the blank solution, the reference solution and the sample solution to be tested are respectively injected according to the chromatographic condition determination described in the example 1, and typical chromatograms of the sample solution to be tested of various manufacturers are shown in fig. 6, fig. 7 and fig. 8. Each manufacturer sample is parallelly measured for 2 parts, calculation is carried out according to the functional relation obtained in the example 2, and the content is calculated as an average value; the peak areas of the diastereomers were also recorded and the peak area percentages were calculated. The results of the experiment are shown in table 4:
TABLE 4 measurement of hydroxypropyl tetrahydropyrane triol content and isomer ratio in different manufacturers
| Manufacturer of the product | Content% (mass percentage) | Isomer ratio |
| A | 31.4 | 67:33 |
| B | 99.6 | 39:61 |
| C | 73.8 | 36:64 |
And (4) conclusion: from the measurement results, it is found that the content of hydroxypropyl tetrahydropyrane triol in the raw material B is high, and the diastereomer ratio of hydroxypropyl tetrahydropyrane triol in the raw material a is high.
Claims (2)
1. A method for measuring the content of hydroxypropyl tetrahydropyrane triol and the diastereoisomer ratio thereof is characterized by comprising the following steps:
A. respectively preparing a blank solution, a reference substance solution and a sample solution to be detected, wherein the blank solution is purified water, and the reference substance solution is a hydroxypropyl tetrahydropyrane triol reference substance solution; the sample solution to be detected is a solution with different concentrations prepared by a hydroxypropyl tetrahydropyrane triol raw material;
B. and C, injecting the blank solution, the reference solution and the sample solution to be detected prepared in the step A into a liquid chromatograph, and setting chromatographic conditions as follows: the chromatographic column is an amide bonded phase chromatographic column, 4.6 multiplied by 250mm, 5 mu m; the sample injection volume is 10 mul; the flow rate is 0.9-1.0 ml/min; the column temperature is 25-30 ℃; the detector is ELSD; the temperature of the evaporation chamber is 40-50 ℃; the temperature of the drift tube is 40-50 ℃; the gas flow rate is 1.6 ml/min; mobile phase: the mobile phase A is methanol, and the mobile phase B is acetonitrile; the elution program was set up as follows: at 0 minute, the methanol concentration is 0, and the acetonitrile concentration is 100%; at 20 minutes, the concentration of methanol is 20 percent, and the concentration of acetonitrile is 80 percent; at 20.1 minutes, the concentration of methanol is 0, and the concentration of acetonitrile is 100 percent; at 29 minutes, the concentration of methanol is 0 and the concentration of acetonitrile is 100 percent; and recording the chromatogram.
2. The method for determining the content of hydroxypropyl tetrahydropyrane triol and the diastereomer ratio thereof according to claim 1, wherein: the amide bonded phase chromatographic column is XAmide, 4.6 multiplied by 250mm, 5 mu m.
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Cited By (5)
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| CN114019048A (en) * | 2021-11-02 | 2022-02-08 | 成都格纯生物医药有限公司 | Method for measuring content of hydroxypropyl tetrahydropyrane triol and diastereoisomer ratio thereof |
| CN114705791A (en) * | 2022-03-11 | 2022-07-05 | 中检科(北京)化妆品技术有限公司 | Method for detecting content of vitronectin in cosmetics |
| CN115097052A (en) * | 2022-08-24 | 2022-09-23 | 山东君泰药业有限公司济南分公司 | Method for determining diastereoisomer ratio of hydroxypropyl tetrahydropyrane triol |
| CN117723679A (en) * | 2024-02-05 | 2024-03-19 | 长沙创新药物工业技术研究院有限公司 | Detection method of R-/S-hydroxypropyl tetrahydropyran triol |
| CN118130686A (en) * | 2024-05-08 | 2024-06-04 | 山东省食品药品检验研究院 | Method for simultaneously detecting glabridin and vitriol |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114019048A (en) * | 2021-11-02 | 2022-02-08 | 成都格纯生物医药有限公司 | Method for measuring content of hydroxypropyl tetrahydropyrane triol and diastereoisomer ratio thereof |
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| CN115097052A (en) * | 2022-08-24 | 2022-09-23 | 山东君泰药业有限公司济南分公司 | Method for determining diastereoisomer ratio of hydroxypropyl tetrahydropyrane triol |
| CN117723679A (en) * | 2024-02-05 | 2024-03-19 | 长沙创新药物工业技术研究院有限公司 | Detection method of R-/S-hydroxypropyl tetrahydropyran triol |
| CN117723679B (en) * | 2024-02-05 | 2024-05-24 | 长沙创新药物工业技术研究院有限公司 | Detection method of R-/S-hydroxypropyl tetrahydropyran triol |
| CN118130686A (en) * | 2024-05-08 | 2024-06-04 | 山东省食品药品检验研究院 | Method for simultaneously detecting glabridin and vitriol |
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Application publication date: 20210423 |