CN105669802A - Method for purifying troxerutin from troxerutin industrial decoction dreg - Google Patents
Method for purifying troxerutin from troxerutin industrial decoction dreg Download PDFInfo
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- CN105669802A CN105669802A CN201610146091.9A CN201610146091A CN105669802A CN 105669802 A CN105669802 A CN 105669802A CN 201610146091 A CN201610146091 A CN 201610146091A CN 105669802 A CN105669802 A CN 105669802A
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- troxerutin
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
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Abstract
The invention provides a method for purifying troxerutin from troxerutin industrial decoction dreg. The method comprises the steps that a separated material is pretreated and loaded into a chromatographic column; the troxerutin industrial decoction dreg is dissolved with water, stands and is filtered; filter liquor is sampled, adsorbed and eluted, eluant is concentrated and dried to obtain troxerutin, the content is 80% (HPLC detection), the recovery rate is 80%, and an obtained product meets the oral liquid standard of Chinese pharmacopoeia in 2015 version. Waste resources of synthetic drugs are effectively utilized, regeneration value of troxerutin is improved, and the method is fast, simple and suitable for industrialized production, and has an application prospect in the aspect of recycling troxerutin waste liquor.
Description
Technical field
The present invention relates to material medicine, specifically belong to a kind of method of purification troxerutin from the troxerutin industry dregs of a decoction.
Background technology
Troxerutin Chinese another name: hydroxyethyl rutin, Flevex, Z 6000, troxerutin, troxerutin, English name: Troxerutine. This product is easily molten in water, at methyl alcohol, dissolves in ethanol, insoluble in chloroform. Molecular formula: C33H42O19, molecular weight 742.68. This product has suppression red corpuscle and thrombocyte cohesion, prevents thrombosis, can increase the content of oxygen in blood simultaneously, improve microcirculation, promotes that new vascular generation is to promote Doppler flow mapping. The diseases such as the oedema that before being applicable to the hemiplegia caused by cerebral thrombosis and cerebral embolism, aphasia and myocardial infarction, syndrome, arteriosclerosis, central serous chorioretinopathy, thrombophlebitis, varix, vascular permeability rising cause.
Troxerutin is through rutin and oxyethane through Willanson etherificate nucleophilic substitution reaction, then is prepared by recrystallization technology and obtain. Because the reaction site of rutin is more, this reaction understands more long-living row by products after completing, in recrystallization preparation process, a large amount of lymphatic temperament can be produced again simultaneously, colloid composition, a large amount of troxerutins is stayed in crystalline mother solution, and then forms the industry dregs of a decoction, as offal treatment, also just make production cost greatly increase, also bring the problem of environmental pollution simultaneously.
At present, the producer of domestic troxerutin raw material probably has tens, and someone added up the nearly kiloton of the dregs of a decoction therefore produced every year, and owing to processing, causes a large amount of dregs of a decoction to be discarded, and causes environmental pollution and financial loss. In addition, a large amount of byproduct of reaction and lymphatic temperament is there is inside the dregs of a decoction, colloid composition etc. causes the dregs of a decoction to recycle quite difficulty, report is had to adopt two kinds of organic floculants to be processed by crystalline mother solution at present, then macroporous resin is adopted to carry out the patent report (Chinese patent: the purifying process of a kind of troxerutin crystalline mother solution, application number: 201210590546.8) that absorb-elute reaches purifying. But this patent procedure complex steps, and purified troxerutin content is only 61.8%, not meeting 2015 editions oral standard-required troxerutin content of " Chinese Pharmacopoeia " regulation troxerutin is the standard of 80%.
Summary of the invention
It is an object of the invention to provide a kind of method of fast purifying troxerutin from the troxerutin industry dregs of a decoction.
The method of a kind of fast purifying troxerutin from the troxerutin industry dregs of a decoction provided by the invention, comprises the steps:
Get parting material, spend the night with volume ratio 0%-60% alcohol water soaking, then remove floating matter, load in chromatography column, for subsequent use;The troxerutin industry dregs of a decoction are shattered, after being equivalent to dregs of a decoction weight 5-10 water dissolution doubly, leaves standstill 6-12h, filter, discard filter residue; Filtrate is added in glass column, first clean column cap with a small amount of water, clean after totally until column cap, wash-out is carried out with corresponding 0%-60% alcohol solution, abandon the elutriant of front 1-2 column volume, continue to collect the elutriant of 1-2 column volume, concentrating under reduced pressure, vacuum-drying. HPLC detects analysis, and troxerutin content reaches more than 80%.
The described troxerutin industry dregs of a decoction, it is manufacturing enterprise with rutin and oxyethane through Willanson etherificate nucleophilic substitution reaction, prepared in the production process of troxerutin again by recrystallization technology, the industrial dregs of a decoction that the crystalline mother solution of generation is formed, wherein containing a large amount of troxerutins.
Described parting material is gelatinous material, it is preferable that hydroxypropyl sephadex lh-20.
The described alcohol in alcohol solution can be ethanol or methyl alcohol etc.
Compared with prior art, the useful effect of the present invention:
The method of fast purifying troxerutin from the industry dregs of a decoction provided by the invention, easy and simple to handle, it is applicable to suitability for industrialized production, and in last finished product, troxerutin content reaches more than 80%, meets the specification requirement of 2015 editions " Chinese Pharmacopoeia " oral liquids.
Accompanying drawing explanation
The HPLC detection figure of Fig. 1 embodiment 1 finished product
The HPLC detection figure of Fig. 2 embodiment 2 finished product
The HPLC detection figure of Fig. 3 embodiment 3 finished product
The HPLC detection figure of Fig. 4 embodiment 4 finished product
The HPLC detection figure of Fig. 5 raw material troxerutin industry dregs of a decoction
Embodiment
The present invention is described in further detail by following examples. The technology contents that the present embodiment is described is explanation property, it should not limit to protection scope of the present invention according to this.
In following examples, Shanxi pharmaceutcal corporation, Ltd taken from by the troxerutin industry dregs of a decoction.
Embodiment 1
Get the 1g troxerutin industry dregs of a decoction and it is placed in 25mL beaker, add 10ml distilled water and dissolve, filter after leaving standstill 12h, discard filter residue, leave filtrate for subsequent use. Get 50g hydroxypropyl sephadex lh-20, spending the night with 500ml distilled water immersion, remove floating matter, (fineness ratio is 1:20 to pour a glass column into, column volume 50mL), treat that soak solution flow to liquid level, add troxerutin dregs of a decoction filtrate, treat that filtrate flow to liquid level, column cap is cleaned again with 1ml distilled water, clean after totally until column cap and add 500ml distilled water wash-out, start after wash-out 100ml to collect, collect 50ml; After 50ml collects liquid concentrating under reduced pressure drying, through HPLC detection, troxerutin reaches 85%, and the rate of recovery is 88%, meets oral liquid specification.
Embodiment 2
Get the 1g troxerutin industry dregs of a decoction and it is placed in 25mL beaker, add 10ml distilled water and dissolve, filter after leaving standstill 12h, discard filter residue, leave filtrate for subsequent use. Get 50g hydroxypropyl sephadex lh-20, with 500ml methanol-water (30% methyl alcohol, volume ratio) solution soaking spends the night, remove floating matter, (fineness ratio is 1:20 to pour a glass column into, column volume 50mL), treat that soak solution flow to liquid level, add troxerutin dregs of a decoction filtrate, treat that filtrate flow to liquid level, then clean column cap with 1ml distilled water, clean after totally until column cap and add 500ml methanol-water (30% methyl alcohol) eluant solution, start after wash-out 100ml to collect, collect 50ml; After 50ml collects liquid concentrating under reduced pressure drying, through HPLC detection, troxerutin content is 82.5%, and the rate of recovery is 80%, meets oral liquid specification.
Embodiment 3
Get the 1g troxerutin industry dregs of a decoction and it is placed in 25mL beaker, add 10ml distilled water and dissolve, filter after leaving standstill 12h, discard filter residue, leave filtrate for subsequent use.Get 50g hydroxypropyl sephadex lh-20, with 500ml methanol-water (60% methyl alcohol, volume ratio) solution soaking spends the night, remove floating matter, (fineness ratio is 1:20 to pour a glass column into, column volume 50mL), treat that soak solution flow to liquid level, add troxerutin dregs of a decoction filtrate, treat that filtrate flow to liquid level, then clean column cap with 1ml distilled water, clean after totally until column cap and add 500ml methanol-water (60% methyl alcohol) eluant solution, start after wash-out 100ml to collect, collect 50ml; After 50ml collects liquid concentrating under reduced pressure drying, through HPLC detection, troxerutin content is 81%, and the rate of recovery is 82%, meets oral liquid specification.
Embodiment 4
Get the 1g troxerutin industry dregs of a decoction and it is placed in 25mL beaker, add 10ml distilled water and dissolve, filter after leaving standstill 12h, discard filter residue, leave filtrate for subsequent use. Get 50g hydroxypropyl sephadex lh-20, with 500ml alcohol-water (60% ethanol, volume ratio) solution soaking spends the night, remove floating matter, (fineness ratio is 1:20 to pour a glass column into, column volume 50mL), treat that soak solution flow to liquid level, add troxerutin dregs of a decoction filtrate, treat that filtrate flow to liquid level, then clean column cap with 1ml distilled water, clean after totally until column cap and add 500ml alcohol-water (60% ethanol) eluant solution, start after wash-out 100ml to collect, collect 50ml; After 50ml collects liquid concentrating under reduced pressure drying, through HPLC detection, troxerutin content is 81%, and the rate of recovery is 82%, meets oral liquid specification.
Claims (5)
1. the method for purifying troxerutin from the troxerutin industry dregs of a decoction, comprises the steps: to get parting material, spends the night with volume ratio 0%-60% alcohol water soaking, then remove floating matter, load in chromatography column, for subsequent use; The troxerutin industry dregs of a decoction are shattered, after being equivalent to dregs of a decoction weight 5-10 water dissolution doubly, leaves standstill 6-12h, filter, discard filter residue; Filtrate is added in glass column, first clean column cap with a small amount of water, clean after totally until column cap, wash-out is carried out with corresponding 0%-60% alcohol solution, abandon the elutriant of front 1-2 column volume, continue to collect the elutriant of 1-2 column volume, concentrating under reduced pressure, vacuum-drying.
2. the method for purifying troxerutin as claimed in claim 1, it is characterised in that, described parting material is gelatinous material.
3. the method for purifying troxerutin as claimed in claim 2, it is characterised in that, described gelatinous material is hydroxypropyl sephadex lh-20.
4. the method for purifying troxerutin as claimed in claim 1, it is characterised in that, the described alcohol in alcohol solution is methyl alcohol or ethanol.
5. the method for purifying troxerutin as claimed in claim 1, it is characterised in that, described water is distilled water.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610146091.9A CN105669802B (en) | 2016-03-15 | 2016-03-15 | A method of purifying Troxerutin from the Troxerutin industry dregs of a decoction |
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| CN201610146091.9A CN105669802B (en) | 2016-03-15 | 2016-03-15 | A method of purifying Troxerutin from the Troxerutin industry dregs of a decoction |
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| CN105669802A true CN105669802A (en) | 2016-06-15 |
| CN105669802B CN105669802B (en) | 2018-10-19 |
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| CN201610146091.9A Expired - Fee Related CN105669802B (en) | 2016-03-15 | 2016-03-15 | A method of purifying Troxerutin from the Troxerutin industry dregs of a decoction |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107501366A (en) * | 2017-08-16 | 2017-12-22 | 西安医学院 | A kind of method that Troxerutin is purified in the waste liquid powder from Troxerutin |
| CN111057116A (en) * | 2019-12-26 | 2020-04-24 | 烟台鲁银药业有限公司 | Preparation method of high-purity tetrahydroxy troxerutin |
| CN111333602A (en) * | 2020-04-16 | 2020-06-26 | 四川迪菲特药业有限公司 | Recovery and conversion process of waste mother liquor in troxerutin production |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3516984A (en) * | 1964-03-26 | 1970-06-23 | Zyma Sa | Process for manufacturing o-beta-hydroxyethyl ethers of rutin |
| CN1032658A (en) * | 1987-10-19 | 1989-05-03 | 烟台人民制药厂 | The process for purification of rutin-hydroxyethyl derivative |
| CN104628799A (en) * | 2014-12-24 | 2015-05-20 | 苏州亚宝药物研发有限公司 | Impurity A in troxerutin and separation method thereof |
-
2016
- 2016-03-15 CN CN201610146091.9A patent/CN105669802B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3516984A (en) * | 1964-03-26 | 1970-06-23 | Zyma Sa | Process for manufacturing o-beta-hydroxyethyl ethers of rutin |
| CN1032658A (en) * | 1987-10-19 | 1989-05-03 | 烟台人民制药厂 | The process for purification of rutin-hydroxyethyl derivative |
| CN104628799A (en) * | 2014-12-24 | 2015-05-20 | 苏州亚宝药物研发有限公司 | Impurity A in troxerutin and separation method thereof |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107501366A (en) * | 2017-08-16 | 2017-12-22 | 西安医学院 | A kind of method that Troxerutin is purified in the waste liquid powder from Troxerutin |
| CN107501366B (en) * | 2017-08-16 | 2020-08-25 | 西安医学院 | Method for purifying troxerutin from troxerutin waste liquid powder |
| CN111057116A (en) * | 2019-12-26 | 2020-04-24 | 烟台鲁银药业有限公司 | Preparation method of high-purity tetrahydroxy troxerutin |
| CN111333602A (en) * | 2020-04-16 | 2020-06-26 | 四川迪菲特药业有限公司 | Recovery and conversion process of waste mother liquor in troxerutin production |
| CN111333602B (en) * | 2020-04-16 | 2022-12-16 | 四川协力制药股份有限公司 | Recovery and conversion process of waste mother liquor in troxerutin production |
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| CN105669802B (en) | 2018-10-19 |
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