CN102866235A - Detection method for D-glucosamine sulfate - Google Patents
Detection method for D-glucosamine sulfate Download PDFInfo
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- CN102866235A CN102866235A CN2012103889441A CN201210388944A CN102866235A CN 102866235 A CN102866235 A CN 102866235A CN 2012103889441 A CN2012103889441 A CN 2012103889441A CN 201210388944 A CN201210388944 A CN 201210388944A CN 102866235 A CN102866235 A CN 102866235A
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- sulfate
- salt
- detection method
- glucosamine
- aminoglucose
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- 238000001514 detection method Methods 0.000 title claims abstract description 47
- FGNPLIQZJCYWLE-BTVCFUMJSA-N (2r,3r,4s,5r)-2-amino-3,4,5,6-tetrahydroxyhexanal;sulfuric acid Chemical compound OS(O)(=O)=O.O=C[C@H](N)[C@@H](O)[C@H](O)[C@H](O)CO FGNPLIQZJCYWLE-BTVCFUMJSA-N 0.000 title abstract 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000002904 solvent Substances 0.000 claims abstract description 26
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims abstract description 22
- 239000007787 solid Substances 0.000 claims abstract description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 19
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 16
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical class N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000001103 potassium chloride Substances 0.000 claims abstract description 11
- 235000011164 potassium chloride Nutrition 0.000 claims abstract description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 claims abstract description 10
- 235000011152 sodium sulphate Nutrition 0.000 claims abstract description 10
- 239000011780 sodium chloride Substances 0.000 claims abstract description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 75
- 150000003839 salts Chemical class 0.000 claims description 25
- MSWZFWKMSRAUBD-UHFFFAOYSA-N 2-Amino-2-Deoxy-Hexose Chemical compound NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- CZKFXYNOCSBUJQ-FAYVVVELSA-L S(=O)(=O)([O-])[O-].[Na+].Cl.OC1[C@H](N)[C@@H](O)[C@H](O)[C@H](O1)CO.[Na+] Chemical compound S(=O)(=O)([O-])[O-].[Na+].Cl.OC1[C@H](N)[C@@H](O)[C@H](O)[C@H](O1)CO.[Na+] CZKFXYNOCSBUJQ-FAYVVVELSA-L 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 238000007689 inspection Methods 0.000 claims description 6
- 150000002500 ions Chemical class 0.000 claims description 6
- YCHKFNUDARWTSK-FRWAFGSFSA-M potassium;(3r,4r,5s,6r)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol;sulfuric acid;chloride Chemical group [Cl-].[K+].OS(O)(=O)=O.N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O YCHKFNUDARWTSK-FRWAFGSFSA-M 0.000 claims description 6
- CXDROOLCWFOLNJ-FRWAFGSFSA-M sodium;(3r,4r,5s,6r)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol;sulfuric acid;chloride Chemical compound [Na+].[Cl-].OS(O)(=O)=O.N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O CXDROOLCWFOLNJ-FRWAFGSFSA-M 0.000 claims description 6
- 241000370738 Chlorion Species 0.000 claims description 3
- 238000001914 filtration Methods 0.000 abstract description 4
- 101000748161 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 34 Proteins 0.000 abstract description 3
- 102100040048 Ubiquitin carboxyl-terminal hydrolase 35 Human genes 0.000 abstract description 3
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 2
- -1 sulphate ions Chemical class 0.000 abstract 2
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 abstract 1
- 229910052939 potassium sulfate Inorganic materials 0.000 abstract 1
- 239000001120 potassium sulphate Substances 0.000 abstract 1
- 235000011151 potassium sulphates Nutrition 0.000 abstract 1
- 206010003246 arthritis Diseases 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000007812 deficiency Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- GEUULXIFKYKUJS-UHFFFAOYSA-L S(O)(O)(=O)=O.[Cl-].[K+].[Cl-].[Na+] Chemical compound S(O)(O)(=O)=O.[Cl-].[K+].[Cl-].[Na+] GEUULXIFKYKUJS-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 210000001188 articular cartilage Anatomy 0.000 description 1
- MSWZFWKMSRAUBD-QZABAPFNSA-N beta-D-glucosamine Chemical compound N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-QZABAPFNSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
Abstract
The invention relates to a detection method for D-glucosamine sulfate. The detection method comprises the following steps: taking D-glucosamine sulfate, and dissolving D-glucosamine sulfate in a solvent at 0-40 DEG C; enabling the solvent to be saturated ammonium sulfate solution or dimethylsulfoxide; enabling the weightmeasurement ratio between D-glucosamine sulfate and the solvent to be (100-200)mg: 1ml; filtering the solution to obtain solids; detecting chloride ions and sulphate ions in the solids according to a detection method of potassium chloride (or sodium chloride) and potassium sulphate (sodium sulfate); by results in detecting the chloride ions and sulphate ions, separating D-glucosamine sulfate prepared in different methods. The detection method is reasonable in design and simple to operate, and D-glucosamine sulfate prepared in the different methods can be separated. The method overcomes shortcomings of USP34, instruments which are extremely strict and precise are not required, and detection can be performed by ordinary factories.
Description
Technical field
The present invention relates to a kind of detection method of sulfate, be specifically related to a kind of detection method of D-aminoglucose sulfate.
Background technology
The D-aminoglucose sulfate records the earliest in American Pharmacopeia 27 editions, is a kind of medicine for the treatment of of arthritis.Arthritis has become the No.1 disabling disease in the world, along with aggravation and the activity of arthritis ache are obstructed, will cause the temporary transient or permanent ability of losing the job.Bring heavy losses for society and economic aspect, the D-aminoglucose sulfate easily absorbs because active high, is the main matrix of articular cartilage and joint fluid, is widely used in more and more the treatment of arthritis disease.
D-Glucosamine of the prior art mainly contains two classes, and a class is D-Glucosamine Hydrochloride, and a class is the D-aminoglucose sulfate.Aspect the arthritis treatment effect, the D-Glucosamine Hydrochloride effect is general, and larger spinoff is arranged simultaneously, particularly to hypertension, and cardiovascular and cerebrovascular, the patient of the diseases such as ephrosis is obvious especially.And the D-aminoglucose sulfate is less owing to its molecule, and human body absorbs easily, can directly arrive focus, so more obvious on the arthritis treatment effect.Because pure D-aminoglucose sulfate is very easy to moisture absorption, thereby causes unstable products, the long-term placement, the content step-down, and be unsuitable for large-scale industrial production.
The D-aminoglucose sulfate is divided into according to preparation method's difference on the market: a kind of D-of being Glucosamine sulfuric acid potassium chloride (sodium) salt, and its structural formula is [A]:
【A】
Another kind is D-Glucosamine Hydrochloride glazier's salt (sodium) potpourri, and its structural formula is [B]:
【B】
These two kinds of compounds detect according to the USP34 detection method, can both reach its standard-required.But its synthetic method is fully different.
Before a kind of large sharp preparation method of Loda S. A. R. L. that complies with one's wishes, the D-aminoglucose sulfate is made the form of double salt, be about to D-aminoglucose sulfate and sodium chloride or potassium chloride and make double salt.
Rear a kind of such as commonsense method, D-Glucosamine Hydrochloride and glazier's salt (sodium) are mixed according to mol ratio.
Summary of the invention
Technical matters to be solved by this invention is for the deficiency of existing detection method, and a kind of detection method advantages of simple is provided, and can distinguish the detection method of D-aminoglucose sulfate of the product of distinct methods preparation.
Technical matters to be solved by this invention is to realize by following technical scheme.The present invention is a kind of detection method of D-aminoglucose sulfate, is characterized in, its step is as follows:
(1) dissolving: get the D-aminoglucose sulfate, under 0～40 ℃, be dissolved in the solvent; Described solvent is saturated ammonium sulfate solution or dimethyl sulfoxide; The w/v of D-aminoglucose sulfate and solvent is 100-200mg:1ml; Solution filter obtains solid;
(2) detect: with the gained solid, press the detection method of potassium chloride (or sodium chloride) and glazier's salt (or sodium sulphate), chlorine detection ion and sulfate ion; The detection method of described chlorion, sulfate ion is all by " two appendix VIII of Chinese pharmacopoeia version in 2010 A chloride inspection technique, appendix VIII B sulfate inspection technique;
(3) judge: by the result of above-mentioned chlorine detection ion and sulfate ion, the D-aminoglucose sulfate that distinct methods is prepared distinguishes;
In saturated ammonium sulfate solution, consoluet is D-Glucosamine sulfuric acid potassium chloride salt or D-Glucosamine sulfuric acid sodium chloride salt, insoluble matter is arranged and for glazier's salt, the original is D-Glucosamine Hydrochloride glazier's salt potpourri, insoluble matter is arranged and for sodium sulphate, the original is D-Glucosamine Hydrochloride sodium sulphate potpourri;
Dissolve in dimethyl sulfoxide, insolubles is potassium chloride, and the original is D-Glucosamine sulfuric acid potassium chloride salt; Insolubles is sodium chloride, and the original is D-Glucosamine sulfuric acid sodium chloride salt;
Dissolve in dimethyl sulfoxide, insolubles is glazier's salt, and the original is D-Glucosamine Hydrochloride glazier's salt potpourri; Insolubles is sodium sulphate, and the original is D-Glucosamine Hydrochloride sodium sulphate potpourri.
In the step of above-described detection method (1), get the D-aminoglucose sulfate, preferably under 10～25 ℃, be dissolved in the solvent.
Compared with prior art, detection method of the present invention is reasonable in design, and is simple to operate, can distinguish the D-aminoglucose sulfate of distinct methods preparation.The inventive method has been replenished the deficiency of USP34, does not need very strict and very accurate instrument, and general factory can detect voluntarily.
Embodiment
Below further describe concrete technical scheme of the present invention, so that those skilled in the art understands the present invention further, and do not consist of its Copyright law.
Embodiment 1, a kind of detection method of D-aminoglucose sulfate, and its step is as follows:
(1) dissolving: get the D-aminoglucose sulfate, under 0 ℃, be dissolved in the solvent; Described solvent is saturated ammonium sulfate solution or dimethyl sulfoxide; The w/v of D-aminoglucose sulfate and solvent is 100mg:1ml; Solution filter obtains solid;
(2) detect: with the gained solid, press the detection method of potassium chloride (or sodium chloride) and glazier's salt (or sodium sulphate), chlorine detection ion and sulfate ion; The detection method of described chlorion, sulfate ion is all by " two appendix VIII of Chinese pharmacopoeia version in 2010 A chloride inspection technique, appendix VIII B sulfate inspection technique;
(3) judge: by the result of above-mentioned chlorine detection ion and sulfate ion, the D-aminoglucose sulfate that distinct methods is prepared distinguishes;
In saturated ammonium sulfate solution, consoluet is D-Glucosamine sulfuric acid potassium chloride salt or D-Glucosamine sulfuric acid sodium chloride salt, insoluble matter is arranged and for glazier's salt, the original is D-Glucosamine Hydrochloride glazier's salt potpourri, insoluble matter is arranged and for sodium sulphate, the original is D-Glucosamine Hydrochloride sodium sulphate potpourri;
Dissolve in dimethyl sulfoxide, insolubles is potassium chloride, and the original is D-Glucosamine sulfuric acid potassium chloride salt; Insolubles is sodium chloride, and the original is D-Glucosamine sulfuric acid sodium chloride salt;
Dissolve in dimethyl sulfoxide, insolubles is glazier's salt, and the original is D-Glucosamine Hydrochloride glazier's salt potpourri; Insolubles is sodium sulphate, and the original is D-Glucosamine Hydrochloride sodium sulphate potpourri.
Embodiment 2, a kind of detection method of D-aminoglucose sulfate, and its step is as follows:
(1) dissolving: get the D-aminoglucose sulfate, under 40 ℃, be dissolved in the solvent; Described solvent is saturated ammonium sulfate solution or dimethyl sulfoxide; The w/v of D-aminoglucose sulfate and solvent is 200mg:1ml; Solution filter obtains solid;
Step (2), (3) are identical with embodiment 1.
Embodiment 3, a kind of detection method of D-aminoglucose sulfate, and its step is as follows:
(1) dissolving: get the D-aminoglucose sulfate, under 10 ℃, be dissolved in the solvent; Described solvent is saturated ammonium sulfate solution or dimethyl sulfoxide; The w/v of D-aminoglucose sulfate and solvent is 120mg:1ml; Solution filter obtains solid;
Step (2), (3) are identical with embodiment 1.
Embodiment 4, a kind of detection method of D-aminoglucose sulfate, and its step is as follows:
(1) dissolving: get the D-aminoglucose sulfate, under 25 ℃, be dissolved in the solvent; Described solvent is saturated ammonium sulfate solution or dimethyl sulfoxide; The w/v of D-aminoglucose sulfate and solvent is 150mg:1ml; Solution filter obtains solid;
Step (2), (3) are identical with embodiment 1.
Embodiment 5, a kind of detection method of D-aminoglucose sulfate, and its step is as follows:
(1) dissolving: get the D-aminoglucose sulfate, under 20 ℃, be dissolved in the solvent; Described solvent is saturated ammonium sulfate solution or dimethyl sulfoxide; The w/v of D-aminoglucose sulfate and solvent is 180mg:1ml; Solution filter obtains solid;
Step (2), (3) are identical with embodiment 1.
Embodiment 6, a kind of detection method experiment one of D-aminoglucose sulfate, its step is as follows: each 110mg of D-aminoglucose sulfate of modus ponens [A] and formula [B], under 0 ℃ of condition, be dissolved in respectively in the saturated ammonium sulfate solution of 1ml, can consoluetly be D-aminoglucose sulfate [A], can not dissolve fully, through filtering, the gained solid is glazier's salt (sodium) through detecting, and this is D-aminoglucose sulfate [B].
Embodiment 7, a kind of detection method experiment two of D-aminoglucose sulfate, its step is as follows: each 200mg of D-aminoglucose sulfate of modus ponens [A] and formula [B], under 4O ℃ of condition, be dissolved in respectively in the saturated ammonium sulfate solution of 1ml, can consoluetly be D-aminoglucose sulfate [A], can not dissolve fully, through filtering, the gained solid is glazier's salt (sodium) through detecting, and this is D-aminoglucose sulfate [B].
Embodiment 8, a kind of detection method experiment three of D-aminoglucose sulfate, its step is as follows: each 160mg of D-aminoglucose sulfate of modus ponens [A] and formula [B], under 25 ℃ of conditions, be dissolved in respectively in the saturated ammonium sulfate solution of 1ml, can consoluetly be D-aminoglucose sulfate [A], can not dissolve fully, through filtering, the gained solid is glazier's salt (sodium) through detecting, and this is D-aminoglucose sulfate [B].
Embodiment 9, a kind of detection method of D-aminoglucose sulfate experiment four, its step is as follows: modus ponens [A] and formula [B] get each 100mg of D-aminoglucose sulfate, under 0 ℃ of condition, be dissolved in respectively in the dimethyl sulfoxide, do not dissolve part, filter respectively and detect.The detection solid is potassium chloride, and the original is D-aminoglucose sulfate [A].The detection solid is glazier's salt, and the original is D-aminoglucose sulfate [B].
Embodiment 10, a kind of detection method of D-aminoglucose sulfate experiment five, its step is as follows: modus ponens [A] and formula [B] get each 160mg of D-aminoglucose sulfate, under 25 ℃ of conditions, be dissolved in respectively in the dimethyl sulfoxide, do not dissolve part, filter respectively and detect.The detection solid is potassium chloride, and the original is D-aminoglucose sulfate [A].The detection solid is glazier's salt, and the original is D-aminoglucose sulfate [B].
Embodiment 11, a kind of detection method of D-aminoglucose sulfate experiment six, its step is as follows: modus ponens [A] and formula [B] get each 200mg of D-aminoglucose sulfate, under 40 ℃ of conditions, be dissolved in respectively in the dimethyl sulfoxide, do not dissolve part, filter respectively and detect.The detection solid is potassium chloride, and the original is D-aminoglucose sulfate [A].The detection solid is glazier's salt, and the original is D-aminoglucose sulfate [B].
Claims (2)
1. the detection method of a D-aminoglucose sulfate is characterized in that, its step is as follows:
(1) dissolving: get the D-aminoglucose sulfate, under 0～40 ℃, be dissolved in the solvent; Described solvent is saturated ammonium sulfate solution or dimethyl sulfoxide; The w/v of D-aminoglucose sulfate and solvent is 100-200mg:1ml; Solution filter obtains solid;
(2) detect: with the gained solid, press the detection method of potassium chloride, sodium chloride, glazier's salt or sodium sulphate, chlorine detection ion and sulfate ion; The detection method of described chlorion, sulfate ion is all by " two appendix VIII of Chinese pharmacopoeia version in 2010 A chloride inspection technique, appendix VIII B sulfate inspection technique;
(3) judge: by the result of above-mentioned chlorine detection ion and sulfate ion, the D-aminoglucose sulfate that distinct methods is prepared distinguishes;
In saturated ammonium sulfate solution, consoluet is D-Glucosamine sulfuric acid potassium chloride salt or D-Glucosamine sulfuric acid sodium chloride salt, insoluble matter is arranged and for glazier's salt, the original is D-Glucosamine Hydrochloride glazier's salt potpourri, insoluble matter is arranged and for sodium sulphate, the original is D-Glucosamine Hydrochloride sodium sulphate potpourri;
Dissolve in dimethyl sulfoxide, insolubles is potassium chloride, and the original is D-Glucosamine sulfuric acid potassium chloride salt; Insolubles is sodium chloride, and the original is D-Glucosamine sulfuric acid sodium chloride salt;
Dissolve in dimethyl sulfoxide, insolubles is glazier's salt, and the original is D-Glucosamine Hydrochloride glazier's salt potpourri; Insolubles is sodium sulphate, and the original is D-Glucosamine Hydrochloride sodium sulphate potpourri.
2. the detection method described in according to claim 1 is characterized in that, in the step (1), gets the D-aminoglucose sulfate, under 10～25 ℃, is dissolved in the solvent.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105866362A (en) * | 2016-06-16 | 2016-08-17 | 江苏澳新生物工程有限公司 | Identification method for glucosamine sulfate and sodium (potassium) chloride salt |
| CN106496289A (en) * | 2016-10-19 | 2017-03-15 | 大连皮米海洋生物研究院 | A kind of manufacturing process of D glucosamine sulphates |
| CN112305095A (en) * | 2020-09-30 | 2021-02-02 | 江苏江大源生态生物科技股份有限公司 | Method for detecting glucosamine sulfate by high performance liquid chromatography |
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| CN112305095A (en) * | 2020-09-30 | 2021-02-02 | 江苏江大源生态生物科技股份有限公司 | Method for detecting glucosamine sulfate by high performance liquid chromatography |
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| CN102866235B (en) | 2014-12-24 |
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