CN114019048A - 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
- Publication number
- CN114019048A CN114019048A CN202111287116.4A CN202111287116A CN114019048A CN 114019048 A CN114019048 A CN 114019048A CN 202111287116 A CN202111287116 A CN 202111287116A CN 114019048 A CN114019048 A CN 114019048A
- Authority
- CN
- China
- Prior art keywords
- mobile phase
- solution
- content
- hydroxypropyl
- triol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Images
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
-
- 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
- G01N30/04—Preparation or injection of sample to be analysed
-
- 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
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
-
- 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
- G01N30/04—Preparation or injection of sample to be analysed
- G01N2030/042—Standards
Landscapes
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Abstract
The invention discloses a method for measuring hydroxypropyl tetrahydropyrane triol content and diastereoisomer ratio thereof, which mainly comprises the following steps: injecting the prepared blank solution, the reference solution and the sample solution to be detected into a liquid chromatograph, and setting chromatographic conditions as follows: the chromatographic column is an amide bonded phase chromatographic column; the volume of the sample injection amount is 5-30 ul; the flow rate is 0.9-1.0 mL/min; the column temperature is 35-40 ℃; the detector is ELSD; the temperature of the evaporation chamber is 50-60 ℃; the temperature of the drift tube is 50-60 ℃; the gas flow rate is 1.5-2.0 mI/min; mobile phase: the mobile phase A is purified water, the mobile phase B is acetonitrile, and the mobile phase proportion is as follows: the mobile phase A is 5-10: 90-95, v/v; the elution mode is isocratic elution; and recording the chromatogram. The invention has the characteristics of short detection time, high detection sensitivity, good repeatability of detection results and the like.
Description
Technical Field
The invention relates to the technical field of detection and analysis, in particular to a method for determining hydroxypropyl tetrahydropyrane triol content and diastereomer ratio thereof.
Background
Hydroxypropyl tetrahydropyrane triol (Chinese name: boscalid, CAS number: 439685-79-7, English name: hydroxypropyl terahydropyratriol, English abbreviation: HTR) is an artificially chemically synthesized xylose derivative. The hydroxy group on the chiral carbon atom at the 7-position in the structure of the hydroxypropyl tetrahydropyrane triol has a stereochemical structure and coexists in a pair of diastereoisomers. It is reported in the relevant literature that 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 the synthesis of glycosaminoglycans, and different ratios of diastereomers result in different activity levels. With the patent protection for hydroxypropyl tetrahydropyran triol synthesis process expiring at 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.
In patent CN112697933A, a method for determining the content of hydroxypropyl tetrahydropyran triol and the diastereomer ratio thereof is provided, in which a methanol/acetonitrile mobile phase is adopted, and a gradient elution mode is adopted to achieve the simultaneous determination of the content of hydroxypropyl tetrahydropyran triol and the diastereomer ratio within a certain detection range. On one hand, the detection method adopts a gradient elution mode to cause long detection time; on the other hand, the problem of low detection limit exists.
Disclosure of Invention
In view of the above disadvantages, the present invention aims to provide a method for determining the content of hydroxypropyl tetrahydropyran triol and the diastereomer ratio thereof, which can effectively solve the problems of long detection time, low detection limit and narrow detection range of diastereomer ratio in the existing hydroxypropyl tetrahydropyran triol detection method.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a method for measuring the content of hydroxypropyl tetrahydropyrane triol and the proportion of diastereoisomers thereof, which comprises the following steps:
step (1): preparing a blank solution, preparing a reference solution, and preparing a sample solution to be detected; wherein the blank solution is a purified aqueous solution, the reference solution is a hydroxypropyl tetrahydropyrane triol reference aqueous solution, and the sample solution to be detected is aqueous solutions with different concentrations prepared from a hydroxypropyl tetrahydropyrane triol raw material;
step (2): injecting the blank solution, the reference solution and the sample solution to be detected prepared in the step (1) into a liquid chromatograph, and setting chromatographic conditions as follows: the chromatographic column is an amide bonded phase chromatographic column; the volume of the sample injection amount is 5-30 ul; the flow rate is 0.9-1.0 mL/min; the column temperature is 35-40 ℃; the detector is an ELSD (evaporative light scattering detector); the temperature of the evaporation chamber is 50-60 ℃; the temperature of the drift tube is 50-60 ℃; the gas flow rate is 1.5-2.0 mI/min; mobile phase: the mobile phase A is purified water, the mobile phase B is acetonitrile, and the proportion of the mobile phase A to the mobile phase B is 5-10: 90-95, v/v; the elution mode is isocratic elution; and recording the chromatogram.
Further, the parameters of the amide bond phase chromatography column were: 4.6X 250mm, 5 um.
"4.6X 250 mm" in the present invention means that the column length is 250mm and the inner diameter is 4.6 mm; in the present invention, "5 um" means a particle diameter of 5 um.
Further, the sample volume was 20 ul.
Further, the evaporation chamber temperature was 55 ℃.
Further, the drift tube temperature was 55 ℃.
Further, the gas flow rate was 1.8 mI/min.
Furthermore, the ratio of the mobile phase A to the mobile phase B is 5: 90-95.
Further, mobile phase a and mobile phase B were 5: 95.
The invention has the following advantages:
1. compared with the prior art (patent CN112697933A), the method adopts purified water/acetonitrile as a mobile phase system and an isocratic elution mode, and under the condition that other test parameters are the same, the detection time is shorter (at least shortened by more than one time); meanwhile, the background absorption of the purified water/acetonitrile mobile phase system adopted in the invention is lower, so that the detection sensitivity is higher (the limit detection concentration of the hydroxypropyl tetrahydropyrane triol is 10.125 mug/ml).
2. The invention provides a method for measuring hydroxypropyl tetrahydropyrane triol content and diastereoisomer ratio thereof, which is characterized in that a mobile phase system (purified water/acetonitrile mobile phase system; the mobile phase ratio (purified water: acetonitrile: 5-10: 90-95, v/v; isocratic elution), drift tube temperature (50-60 ℃) and evaporation chamber temperature (50-60 ℃) are reasonably selected, so that the detection speed is higher, the detection sensitivity is higher, and the repeatability and the accuracy of detection results are better under the synergistic effect of the parameters, the invention discovers that the detection results and the detection effects are influenced when any one reaction parameter is changed through a large number of experiments, for example, when the mobile phase system in patent CN112697933A is selected as the mobile phase (the mobile phase A is methanol, the mobile phase B is acetonitrile, the elution program is set to be 0 minute, the concentration of methanol is 0 percent, and the concentration of acetonitrile is 100 percent; 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 methanol concentration was 0 and the acetonitrile concentration was 100%), the detection time was doubled, and the limit detection concentration of hydroxypropyl tetrahydropyran triol was 27.085 μ g/ml (which corresponds to 27.041 μ g/ml, which is disclosed in patent CN 112697933A).
Drawings
FIGS. 1-2 are graphs showing the results of the detection in the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the detailed description and specific examples, while indicating the preferred embodiment of the invention, are intended for purposes of illustration only and are not intended to limit the scope of the invention.
Thus, the following detailed description of the embodiments of the present invention is not intended to limit the scope of the invention as claimed, but is merely representative of selected embodiments of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments of the present invention without making any creative effort, shall fall within the protection scope of the present 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. purifying the water;
6. acetonitrile, chromatographic grade;
7. methanol, chromatographic grade;
the reagents or instruments used are conventional products available from regular distributors, not indicated by the manufacturer.
Example 1 detection and quantitation limits of the methods of the invention
1. Chromatographic conditions
A chromatographic column: XAmide (4.6 x 250mm, 5 μm), zhejiang hua spectral innovative science and technology limited;
sample introduction volume: 20 mu l of the mixture; flow rate: 1.0 ml/min; column temperature: 35 ℃;
a detector: ELSD; temperature of the evaporation chamber: 55 ℃; temperature of the drift tube: 55 ℃; gas flow rate: 1.8 ml/min;
mobile phase: mobile phase a-purified water, mobile phase B-acetonitrile, mobile phase a: mobile phase B-5: 95.
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 signal-to-noise ratio S/N of the quantification limit being more than or equal to 10 and the signal-to-noise ratio S/N of the detection limit being more than or equal to 3, the hydroxypropyl tetrahydropyrane triol reference solution is diluted, the chromatographic conditions are determined according to the embodiment, and the experimental results are shown in FIGS. 1-2.
In this example, other test parameters are set according to patent CN112697933A, if not specifically limited. The results show that: the invention adopts purified water/acetonitrile as a mobile phase system and an isocratic elution mode, and under the same condition, the detection time of the invention is shorter (at least shortened by more than one time); meanwhile, the background absorption of the purified water/acetonitrile mobile phase system adopted by the invention is lower, so that the detection sensitivity is higher (the limit detection concentration of the hydroxypropyl tetrahydropyrane triol is 10.125 mu g/ml)
In conclusion, the invention provides a method for determining the content of hydroxypropyl tetrahydropyrane triol and the proportion of diastereoisomers thereof, which has the advantages of higher detection speed, higher detection sensitivity, and better repeatability and accuracy of detection results under the synergistic action of the parameters by reasonably selecting a mobile phase system (purified water/acetonitrile mobile phase system, wherein the mobile phase proportion (purified water: acetonitrile: 5-10: 90-95, v/v; isocratic elution), the drift tube temperature (50-60 ℃) and the evaporation chamber temperature (50-60 ℃).
The foregoing is merely exemplary and illustrative of the present invention and it is within the purview of one skilled in the art to modify or supplement the embodiments described or to substitute similar ones without the exercise of inventive faculty, and still fall within the scope of the claims.
Claims (8)
1. A method for measuring the content of hydroxypropyl tetrahydropyrane triol and the diastereoisomer ratio thereof is characterized by comprising the following steps:
step (1): preparing a blank solution, preparing a reference solution, and preparing a sample solution to be detected; wherein the blank solution is a purified aqueous solution, the reference solution is a hydroxypropyl tetrahydropyrane triol reference aqueous solution, and the sample solution to be detected is aqueous solutions with different concentrations prepared from a hydroxypropyl tetrahydropyrane triol raw material;
step (2): injecting the blank solution, the reference solution and the sample solution to be detected prepared in the step (1) into a liquid chromatograph, and setting chromatographic conditions as follows: the chromatographic column is an amide bonded phase chromatographic column; the volume of the sample injection amount is 5-30 ul; the flow rate is 0.9-1.0 mL/min; the column temperature is 35-40 ℃; the detector is ELSD; the temperature of the evaporation chamber is 50-60 ℃; the temperature of the drift tube is 50-60 ℃; the gas flow rate is 1.5-2.0 mI/min; mobile phase: the mobile phase A is purified water, the mobile phase B is acetonitrile, and the proportion of the mobile phase A to the mobile phase B is 5-10: 90-95, v/v; the elution mode is isocratic elution; 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 parameters of the amide bonded phase chromatographic column are: 4.6X 250mm, 5 um.
3. The method for measuring the content of hydroxypropyl tetrahydropyrane triol and the diastereomer ratio thereof according to claim 1, wherein the sample volume is 20 ul.
4. The method for measuring the content of hydroxypropyl tetrahydropyrane triol and the diastereomer ratio thereof according to claim 1, wherein the evaporation chamber temperature is 55 ℃.
5. The method for measuring hydroxypropyl tetrahydropyran triol content and the diastereomer ratio thereof according to claim 1, wherein the drift tube temperature is 55 ℃.
6. The method for measuring the content of hydroxypropyl tetrahydropyrane triol and the diastereomer ratio thereof according to claim 1, wherein the gas flow rate is 1.8 ml/min.
7. The method for determining the content and the diastereomer ratio of hydroxypropyl tetrahydropyrane triol according to claim 1, wherein the ratio of the mobile phase A to the mobile phase B is 5: 90-95.
8. The method for determining the content of hydroxypropyl tetrahydropyrane triol and the diastereomer ratio thereof according to claim 1 or 7, wherein the ratio of mobile phase A to mobile phase B is 5: 95.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111287116.4A CN114019048A (en) | 2021-11-02 | 2021-11-02 | Method for measuring content of hydroxypropyl tetrahydropyrane triol and diastereoisomer ratio thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111287116.4A CN114019048A (en) | 2021-11-02 | 2021-11-02 | Method for measuring content of hydroxypropyl tetrahydropyrane triol and diastereoisomer ratio thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114019048A true CN114019048A (en) | 2022-02-08 |
Family
ID=80059653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111287116.4A Pending CN114019048A (en) | 2021-11-02 | 2021-11-02 | Method for measuring content of hydroxypropyl tetrahydropyrane triol and diastereoisomer ratio thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114019048A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN115236218A (en) * | 2022-06-17 | 2022-10-25 | 上海市食品药品检验研究院 | Method for detecting vitreous color factor in cosmetics based on HPLC-CAD |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108120792A (en) * | 2017-12-14 | 2018-06-05 | 青海出入境检验检疫局检验检疫综合技术中心 | A kind of efficient liquid phase detection of tetrahydropyrimidine and content assaying method |
| CN111876452A (en) * | 2020-07-01 | 2020-11-03 | 江苏瑞蓓丽生物科技有限公司 | Method for preparing vitronectin by biological enzyme one-pot method |
| CN112697933A (en) * | 2020-12-04 | 2021-04-23 | 珀莱雅化妆品股份有限公司 | Method for measuring content of hydroxypropyl tetrahydropyrane triol and diastereoisomer ratio thereof |
| CN112858185A (en) * | 2021-01-11 | 2021-05-28 | 山东省食品药品检验研究院 | Content determination method of hydroxypropyl tetrahydropyrane triol |
| CN113416756A (en) * | 2021-07-12 | 2021-09-21 | 上海克琴科技有限公司 | Method for synthesizing hydroxypropyl tetrahydropyrane triol catalyzed by biological enzyme |
-
2021
- 2021-11-02 CN CN202111287116.4A patent/CN114019048A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108120792A (en) * | 2017-12-14 | 2018-06-05 | 青海出入境检验检疫局检验检疫综合技术中心 | A kind of efficient liquid phase detection of tetrahydropyrimidine and content assaying method |
| CN111876452A (en) * | 2020-07-01 | 2020-11-03 | 江苏瑞蓓丽生物科技有限公司 | Method for preparing vitronectin by biological enzyme one-pot method |
| CN112697933A (en) * | 2020-12-04 | 2021-04-23 | 珀莱雅化妆品股份有限公司 | Method for measuring content of hydroxypropyl tetrahydropyrane triol and diastereoisomer ratio thereof |
| CN112858185A (en) * | 2021-01-11 | 2021-05-28 | 山东省食品药品检验研究院 | Content determination method of hydroxypropyl tetrahydropyrane triol |
| CN113416756A (en) * | 2021-07-12 | 2021-09-21 | 上海克琴科技有限公司 | Method for synthesizing hydroxypropyl tetrahydropyrane triol catalyzed by biological enzyme |
Non-Patent Citations (1)
| Title |
|---|
| HAUDREY ASSIER 等: "First case of contact dermatitis caused by hydroxypropyl tetrahydropyrantriol used in an anti-ageing cream", CONTACT DERMATITIS, vol. 77, pages 60 - 61 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115236218A (en) * | 2022-06-17 | 2022-10-25 | 上海市食品药品检验研究院 | Method for detecting vitreous color factor in cosmetics based on HPLC-CAD |
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN114019048A (en) | Method for measuring content of hydroxypropyl tetrahydropyrane triol and diastereoisomer ratio thereof | |
| Edlund | Determination of opiates in biological samples by glass capillary gas chromatography with electron-capture detection | |
| CN112697933A (en) | Method for measuring content of hydroxypropyl tetrahydropyrane triol and diastereoisomer ratio thereof | |
| CN102175792A (en) | Method for detecting estrogen, nonyl phenol, octylphenol and bisphenol A together in water environment | |
| CN109060984A (en) | A method of N- dimethylnitrosamine content in detection Valsartan and its preparation | |
| CN103969385B (en) | Five kinds of alkaloidal qualifications in the Bi roots of grass and pepper and content Simultaneous Determination method | |
| CN111766317A (en) | Method for measuring GS-441524 content in preparation by using polyethylene glycol and water | |
| Frost et al. | Determination of pharmaceutical process impurities by solid phase microextraction gas chromatography | |
| CN112798719B (en) | Detection method of related substance N-methylpiperazine in sildenafil citrate | |
| Koolstra et al. | Development of a reference method for determining urinary oxalate by means of isotope dilution—Mass spectrometry (ID-MS) and its usefulness in testing existing assays for urinary oxalate | |
| Bratinčević et al. | Comparison of the solid phase and liquid-liquid extraction methods for methadone determination in human serum and whole blood samples using gas chromatography/mass spectrometry | |
| CN116297978A (en) | HPLC method for separating and measuring posaconazole Z 3 And methods for impurity and solvent thereof | |
| CN104502486B (en) | A kind of apply the method for methyl vanillin and ethyl vanillin in Headspace-solid phase microextraction technical measurement milk powder | |
| KR100902571B1 (en) | Simultaneous determination of demethylamphetamine, amphetamine and their metabolites by liquid chromatography | |
| CN112782333B (en) | HPLC detection method for pitavastatin isopropyl tert-butyl ester diastereoisomer | |
| Williams et al. | A rapid method for the determination of therapeutic barbiturate levels in serum using gas-liquid chromatography | |
| CN114646701A (en) | HPLC (high Performance liquid chromatography) test method for related substances in L-prolinamide | |
| Wall et al. | Determination of baclofen and α-baclofen in rat liver homogenate and human urine using solid-phase extraction, o-phthalaldehyde-tert.-butyl thiol derivatization and high-performance liquid chromatography with amperometric detection | |
| CN112557520A (en) | Method for detecting TGR-1-corresponding isomer in TGR-1 | |
| CN116124926B (en) | Method for determining content of 2-mercaptopyridine in plasmid | |
| CN114200067B (en) | High performance liquid chromatography analysis method for 6-bromo-3-hydroxy pyrazine-2-carboxamide and impurities | |
| CN115963217B (en) | Detection method of imidapril intermediate and impurity | |
| CN115327004B (en) | Method for detecting clopidogrel oxide crude product | |
| CN116930370B (en) | Method for measuring parachloroaniline in paracetamol | |
| WO2023065521A1 (en) | Gas chromatography-mass spectrometry combined method for determining genotoxic impurity 1,3-dichloro-2-propanol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |