CN103570662A - Preparation method of high-purity rutin - Google Patents
Preparation method of high-purity rutin Download PDFInfo
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- CN103570662A CN103570662A CN201310581128.7A CN201310581128A CN103570662A CN 103570662 A CN103570662 A CN 103570662A CN 201310581128 A CN201310581128 A CN 201310581128A CN 103570662 A CN103570662 A CN 103570662A
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Abstract
The invention discloses a preparation method of high-purity rutin. A rutin crude product is used as a raw material; organic solvent is used for thermally dissolving and thermally filtering; chromatographic column separation is implemented for filtrate taking macroporous resin/polyamide, macroporous resin/microcrystalline cellulose or microcrystalline cellulose/polyamide as mixed fillers to obtain the high-purity rutin; the purity of the rutin can be above 98% through HPLC (High Performance Liquid Chromatography) determination; the yield of the rutin can achieve the kilogram level. The preparation method of the high-purity rutin has the advantages of stable and quick process, easy operation and low cost, and is suitable for large-scale industrial production.
Description
Technical field
The present invention relates to the preparation field of natural drug, be specifically related to the preparation method of a kind of high-purity rutin.
Background technology
Rutin (Rutin) has another name called rue leaf glycosides, vitamin P, is the very wide flavonoid compound in a kind of source.Flavonoid compound plays very important effect in the treatment of cardiovascular and cerebrovascular diseases, and rutin is one of them Typical Representative.Simultaneously rutin has the pharmacological actions such as Green Tea Extract activity, antiviral, anti peroxidation of lipid, anti-acute pancreatitis, can be used for the treatment of various diseases.Both at home and abroad pharmaceutical industries be take the medicines such as troxerutin that rutin is raw material production, rutin magnesium chromic salts, multivita-glucose hydroxyl fourth rutin, Quercetin and has been expanded range of application and the curative effect of rutin product, rutin can also be used as natural yellow pigment simultaneously, is also a kind of desirable natural broad spectrum sunscreen.
Along with going deep into of research, rutin is in the broader applications that obtained in each field, and this just makes its demand further strengthen.China is the production and consumption big country of rutin, and current global rutin bulk drug ultimate production has reached 3000～3600 Dun，Er China rutin ultimate productions 1200 tons of left and right, accounts for 1/3 of global rutin ultimate production.Therefore, obtain high-purity rutoside fast and stable and can produce better economic benefit and social benefit.
When laboratory and suitability for industrialized production are extracted rutin, what conventionally adopt is alkali extraction and acid precipitation.The method is to utilize acidity and the minimum characteristic of solubleness of rutin, soluble in water with alkali salify, its solubleness rapid drawdown after acidifying and swim isolated principle, then obtain purer rutin through several recrystallization.The method technical maturity, simple to operate, be regarded as for many years comparatively ideal method, but the rutin purity that the method obtains is only generally 80～90% always, be difficult to meet application demand more and more widely.
Rutin is a kind of flavonoid compound, has a pair of adjacent two phenolic hydroxyl groups in its structure, and chemical property is active, and due to the impact of illumination, temperature etc., the easy recurring structure of adjacent two phenolic hydroxyl group changes, is oxidized or decomposes.Rutin is also easily hydrolyzed and is converted into Quercetin at its contained disaccharide of sour environment, and therefore the preparation of high-purity rutin exists very large difficulty technically.
CN1153174A employing molecular conformation transformation method refined rutin gained sterling rutin yield is high, quality good, but the purity requirement of the method crude product rutin used raw material is in 90% left and right, if be applied to large-scale industrialization, produces, and has greatly increased undoubtedly production cost.CN1546506A adopts the Sevage method deproteinated of Tricholroacetic Acid method deproteinated and improvement to carry out purifying rutin, and this method is simple to operate, save labour, but agents useful for same toxicity is higher, and purity is only 90%, is difficult to meet the current demand to high-purity rutin.CN101260132A adopts high-speed countercurrent chromatography purifying high-purity rutin, and the prepared rutin purity of the method more than 98%, is still used multiple organic solvent, environment is had to certain influence, its preparation simultaneously only has a gram magnitude, and cost is high, is unfavorable for suitability for industrialized production.CN102718820A adopts resin to carry out column chromatography refined rutin, the method is by the deionized water drip washing of gained rutin, under 80～90 ℃ of conditions, be dried 10～14 hours, because easily there is oxidation or the decomposition of part rutin in the long-time dry situation that especially has air or illumination to exist under comparatively high temps, therefore have certain defect.Given this, finding the novel method of the high-purity rutin of a kind of quick preparation and make it and can large-scale industrialization go into operation, has been the task of top priority of current process for producing rutin research.
Summary of the invention
The preparation method who the object of this invention is to provide a kind of high-purity rutin, the defect that can not reach that the purity requirement of raw material rutin is low, product rutin purity is high, preparation process is stable fast, preparation cost is low, reagent toxicity is low during high-purity rutin etc. simultaneously and require in preparation to solve prior art.
For addressing the aforementioned drawbacks, the present invention by the following technical solutions:
A preparation method for high-purity rutin, comprises the steps:
Step 1, take rutin crude product as raw material, mix by 1g:6～13mL with organic solvent, heated and stirred is to dissolving completely, and heat filtering obtains filtrate;
Step 2, step 1 gained filtrate is carried out to column chromatography separation, take macroporous resin/polymeric amide, macroporous resin/Microcrystalline Cellulose or Microcrystalline Cellulose/polymeric amide as mixed fillers, organic solvent wet method dress post, by volume percent, be that 10～20% aqueous solutions of organic solvent, 90～99% aqueous solutions of organic solvent are as eluent successively, elution flow rate is 100～200ml/min, wherein, the mass ratio m/m of macroporous resin/polymeric amide, macroporous resin/Microcrystalline Cellulose or Microcrystalline Cellulose/polymeric amide is 1:3～6:1;
Step 3, according to elutriant color, by the coloured beginning of colourless change, collected for the first time, to brown color, become light yellow collection and finish, will collect for the first time the standing crystallization of gained elutriant;
Step 4, the solid filtering that the standing crystallization of elutriant in step 3 is separated out, and with organic solvent drip washing 2～3 times, under 40～50 ℃ of conditions, vacuum-drying obtains high-purity rutin.
Organic solvent described in step 1, step 2 and step 4 is all methyl alcohol or ethanol.
Described in step 1, the temperature of heated and stirred is 70～80 ℃.
Described in step 2, the quality of mixed fillers is 6～10 times of rutin crude product quality described in step 1.
Step 3 also comprises: according to elutriant color, by light yellow change brown color, started to collect for the second time, to becoming colorless, collect and finish, the elutriant of collecting is for the second time by underpressure distillation, reclaim organic solvent and obtain rutin medicinal extract, the vacuum-drying under 40～50 ℃ of conditions of described rutin medicinal extract, products therefrom is as the raw material of the high-purity rutin of preparation.
Beneficial effect of the present invention:
1, the present invention's chromatographic column filler used is the mixed fillers of the differing materials that uses first, moderate cost, and good separating effect, separation efficiency are high.
2, the present invention is low to the purity requirement of raw material rutin crude product, and purity is more than 80% all applicable, and the purity of high-purity rutin of preparation reaches as high as more than 98%, and output can reach a kilogram magnitude.
3, only methyl alcohol low toxicity, water and ethanol environmental protection and cheap of agents useful for same of the present invention.
4, the prepared high-purity rutoside of the present invention can be used for research and development and the application of medicine, foodstuff additive, makeup, rutin standard substance, and this preparation method is fast stable simultaneously, simple to operate, with low cost, is applicable to large-scale industrial production.
Accompanying drawing explanation
Fig. 1 is that the chromatogram of high-purity rutin of embodiment 1 preparation goes out peak collection of illustrative plates.
Fig. 2 is that the chromatogram of high-purity rutin of embodiment 2 preparations goes out peak collection of illustrative plates.
Fig. 3 is that the chromatogram of high-purity rutin of embodiment 3 preparations goes out peak collection of illustrative plates.
Fig. 4 is that the chromatogram of high-purity rutin of embodiment 4 preparations goes out peak collection of illustrative plates.
Embodiment
Below in conjunction with embodiment and accompanying drawing, the present invention is done further and explained.The following example is only for the present invention is described, but is not used for limiting practical range of the present invention.
A preparation method for high-purity rutin, comprises the steps:
Step 1, take rutin crude product as raw material, mix by 1g:6～13mL with organic solvent, be stirred to completely and dissolve under 70～80 ℃ of conditions, heat filtering obtains filtrate;
Step 2, step 1 gained filtrate is carried out to column chromatography separation, take macroporous resin/polymeric amide, macroporous resin/Microcrystalline Cellulose or Microcrystalline Cellulose/polymeric amide as mixed fillers, organic solvent wet method dress post, by volume percent, be that 10～20% aqueous solutions of organic solvent, 90～99% aqueous solutions of organic solvent are as eluent successively, elution flow rate is 100～200ml/min, wherein, the mass ratio m/m of macroporous resin/polymeric amide, macroporous resin/Microcrystalline Cellulose or Microcrystalline Cellulose/polymeric amide is 1:3～6:1; The quality of mixed fillers is 6～10 times of rutin crude product quality;
Step 3, according to elutriant color, by the coloured beginning of colourless change, collected for the first time, to brown color, become light yellow collection and finish, will collect for the first time the standing crystallization of gained elutriant;
Step 4, the solid filtering that the standing crystallization of elutriant in step 3 is separated out, and with a small amount of organic solvent drip washing 2～3 times, under 40～50 ℃ of conditions, vacuum-drying obtains high-purity rutin.
Step 1, two identical with the organic solvent described in four can be methyl alcohol or ethanol.
After elutriant is collected for the first time, according to elutriant color, by light yellow change brown color, started to collect for the second time, to becoming colorless, collect and finish, the elutriant of collecting is for the second time by underpressure distillation, reclaim organic solvent and obtain rutin medicinal extract, the vacuum-drying under 40～50 ℃ of conditions of described rutin medicinal extract, products therefrom is as the raw material of the high-purity rutin of preparation, to improve the utilization ratio of raw material, reduce preparation cost.
The DM-18 non-polar macroporous resin that macroporous resin Shi You Shandong Lukang Record Pharmaceuticals Co., Ltd. that following examples adopt provides.Polymeric amide is column chromatography polymeric amide, and what following examples adopted is the column chromatography polymeric amide that road and bridge tetramethyl biochemical plastic molding and processing plant in City of Taizhou provides.Microcrystalline Cellulose is column chromatography Microcrystalline Cellulose, and what following examples adopted is the column chromatography Microcrystalline Cellulose that Chemical Reagent Co., Ltd., Sinopharm Group provides.
The present invention is not high to the purity requirement of raw materials used rutin crude product, and purity is more than 80% all applicable, and the rutin crude product that following examples adopt, take the sophora bud as raw material is by alkali extraction and acid precipitation extraction 1～2 acquisition of recrystallization, and purity is 80～85%.The purity of raw material rutin crude product and the high-purity rutin of embodiment products obtained therefrom is pressed the prescriptive procedure of < < Pharmacopoeia of People's Republic of China > > (version in 2010) and is measured, means of testing is high performance liquid chromatography (HPLC), and the purity of product reaches as high as more than 98%.
Embodiment 1
Step 1, to get purity be 83% rutin crude product 500g, under 75 ℃ of conditions, be stirred in the ratio of 1g:6mL with methyl alcohol completely dissolve, heat filtering, obtain filtrate.
Step 2, step 1 gained filtrate is carried out to column chromatography separation, macroporous resin/the polymeric amide of 4500g mass ratio 6:1 of take is mixed fillers, methyl alcohol wet method is loaded in the pillar that diameter is 10cm, obtain the post layer that 90cm is high, use successively volume percent 10% methanol aqueous solution 1.5BV(column volume), 90% methanol aqueous solution 2.5BV is as eluent, elution flow rate is 200ml/min.
Step 3, according to elutriant color, by the coloured beginning of colourless change, collected for the first time, to brown color, become light yellow collection and finish, by the standing crystallization of this gained elutriant; Elutriant is started to be collected into for the second time to become colorless to collect by light yellow change brown color and finishes, by the elutriant underpressure distillation of this collection, to reclaim methyl alcohol and to obtain rutin medicinal extract, the product of rutin medicinal extract vacuum-drying gained under 45 ℃ of conditions can be used as the raw material of the high-purity rutin of preparation.
Step 4, the solid filtering that the standing crystallization of elutriant in step 3 is separated out, and with a small amount of methyl alcohol drip washing 2 times, 40 ℃ of vacuum-dryings obtain high-purity rutin.Final high-purity rutin 337.5g, productive rate is 67.5%, through HPLC, measuring its purity is 98.26%, as shown in Figure 1.
Embodiment 2
Step 1, to get purity be 83% rutin crude product 300g, under 75 ℃ of conditions, be stirred to completely with the ratio of ethanol 1g:13mL dissolve, heat filtering, obtain filtrate.
Step 2, step 1 gained filtrate is carried out to column chromatography separation, macroporous resin/the polymeric amide of 3000g mass ratio 3:1 of take is mixed fillers, ethanol wet method is loaded in the pillar that diameter is 10cm, obtain the post layer that 62cm is high, use successively volume percent 15% aqueous ethanolic solution 1.5BV, 95% aqueous ethanolic solution 3BV as eluent, elution flow rate is 170ml/min.
Step 3, according to elutriant color, by the coloured beginning of colourless change, collected for the first time, to brown color, become light yellow collection and finish, by the standing crystallization of this gained elutriant; Elutriant is started to be collected into for the second time to become colorless to collect by light yellow change brown color and finishes, by the elutriant underpressure distillation of this collection, to reclaim ethanol and to obtain rutin medicinal extract, the product of rutin medicinal extract vacuum-drying gained under 45 ℃ of conditions can be used as the raw material of the high-purity rutin of preparation.
Step 4, the solid filtering that the standing crystallization of elutriant in step 3 is separated out, and with a small amount of ethanol drip washing 3 times, 45 ℃ of vacuum-dryings obtain high-purity rutin.Final high-purity rutin 210.6g, productive rate is 70.2%, through HPLC, measuring its purity is 97.99%, as shown in Figure 2.
Embodiment 3
Step 1, to get purity be 85% rutin crude product 350g, under 80 ℃ of conditions, be stirred in the ratio of 1g:10mL with ethanol completely dissolve, heat filtering, obtain filtrate.
Step 2, step 1 gained filtrate is carried out to column chromatography separation, macroporous resin/the Microcrystalline Cellulose of 3000g mass ratio 4:1 of take is mixed fillers, ethanol wet method is loaded in the pillar that diameter is 10cm, obtain the post layer that 57cm is high, use successively volume percent 20% aqueous ethanolic solution 1.3BV, 99% aqueous ethanolic solution 2.5BV as eluent, elution flow rate 150ml/min.
Step 3, according to elutriant color, by the coloured beginning of colourless change, collected for the first time, to brown color, become light yellow collection and finish, by the standing crystallization of this gained elutriant; Elutriant is started to be collected into for the second time to become colorless to collect by light yellow change brown color and finishes, by the elutriant underpressure distillation of this collection, to reclaim ethanol and to obtain rutin medicinal extract, the product of rutin medicinal extract vacuum-drying gained under 40 ℃ of conditions can be used as the raw material of the high-purity rutin of preparation.
Step 4, the solid filtering that the standing crystallization of elutriant in step 3 is separated out, and with a small amount of ethanol drip washing 3 times, 40 ℃ of vacuum-dryings obtain high-purity rutin.Final high-purity rutin 251g, productive rate is 71.7%, through HPLC, measuring its purity is 97.49%, as shown in Figure 3.
Embodiment 4
Step 1, to get purity be 80% rutin crude product 500g, under 70 ℃ of conditions, be stirred in the ratio of 1g:8mL with methyl alcohol completely dissolve, heat filtering, obtain filtrate.
Step 2, step 1 gained filtrate is carried out to column chromatography separation, Microcrystalline Cellulose/the polymeric amide of 3000g mass ratio 1:3 of take is mixed fillers, methyl alcohol wet method is loaded in the pillar of diameter 10cm, obtain the post layer that 55cm is high, use successively volume percent 15% methanol aqueous solution 1.2BV, 95% methanol aqueous solution 3BV as eluent, elution flow rate is 100ml/min.
Step 3, according to elutriant color, by the coloured beginning of colourless change, collected for the first time, to brown color, become light yellow collection and finish, by the standing crystallization of this gained elutriant; Elutriant is started to be collected into for the second time to become colorless to collect by light yellow change brown color and finishes, by the elutriant underpressure distillation of this collection to reclaim methyl alcohol and to obtain rutin medicinal extract, the vacuum-drying under 50 ℃ of conditions of rutin medicinal extract, products therefrom can be used as the raw material of the high-purity rutin of preparation.
Step 4, the solid filtering that the standing crystallization of elutriant in step 3 is separated out, and with a small amount of methyl alcohol drip washing 2 times, 50 ℃ of vacuum-dryings obtain high-purity rutin.Final high-purity rutin 318.6g, productive rate is 63.7%, through HPLC, measuring its purity is 97.28%, as shown in Figure 4.
Claims (5)
1. a preparation method for high-purity rutin, is characterized in that, comprises the steps:
Step 1, take rutin crude product as raw material, mix by 1g:6～13mL with organic solvent, heated and stirred is to dissolving completely, and heat filtering obtains filtrate;
Step 2, step 1 gained filtrate is carried out to column chromatography separation, take macroporous resin/polymeric amide, macroporous resin/Microcrystalline Cellulose or Microcrystalline Cellulose/polymeric amide as mixed fillers, organic solvent wet method dress post, by volume percent, be that 10～20% aqueous solutions of organic solvent, 90～99% aqueous solutions of organic solvent are as eluent successively, elution flow rate is 100～200ml/min, wherein, the mass ratio m/m of macroporous resin/polymeric amide, macroporous resin/Microcrystalline Cellulose or Microcrystalline Cellulose/polymeric amide is 1:3～6:1;
Step 3, according to elutriant color, by the coloured beginning of colourless change, collected for the first time, to brown color, become light yellow collection and finish, will collect for the first time the standing crystallization of gained elutriant;
Step 4, the solid filtering that the standing crystallization of elutriant in step 3 is separated out, and with organic solvent drip washing 2～3 times, under 40～50 ℃ of conditions, vacuum-drying obtains high-purity rutin.
2. the preparation method of a kind of high-purity rutin according to claim 1, is characterized in that, the organic solvent described in step 1, step 2 and step 4 is all methyl alcohol or ethanol.
3. the preparation method of a kind of high-purity rutin according to claim 1 and 2, is characterized in that, the temperature of heated and stirred is 70～80 ℃ described in step 1.
4. the preparation method of a kind of high-purity rutin according to claim 1 and 2, is characterized in that, the quality of mixed fillers is 6～10 times of rutin crude product quality described in step 1 described in step 2.
5. the preparation method of a kind of high-purity rutin according to claim 1, it is characterized in that, step 3 also comprises: according to elutriant color, by light yellow change brown color, started to collect for the second time, to becoming colorless, collect and finish, the elutriant of collecting is for the second time by underpressure distillation, reclaim organic solvent and obtain rutin medicinal extract, the vacuum-drying under 40～50 ℃ of conditions of described rutin medicinal extract, products therefrom is as the raw material of the high-purity rutin of preparation.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104151380A (en) * | 2014-06-22 | 2014-11-19 | 北京安德益源生物科技有限公司 | Preparation method of high-purity rutin |
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| CN102718820A (en) * | 2012-07-10 | 2012-10-10 | 刘志强 | Method for extracting and refining rutin |
| CN102731593A (en) * | 2011-04-02 | 2012-10-17 | 中国科学院兰州化学物理研究所 | Method for extracting rutin from tartary buckwheat |
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2013
- 2013-11-19 CN CN201310581128.7A patent/CN103570662A/en active Pending
Patent Citations (5)
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| JPH0273079A (en) * | 1988-09-09 | 1990-03-13 | Daicel Chem Ind Ltd | Production of flavonoid |
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| CN102731593A (en) * | 2011-04-02 | 2012-10-17 | 中国科学院兰州化学物理研究所 | Method for extracting rutin from tartary buckwheat |
| CN102670696A (en) * | 2012-05-03 | 2012-09-19 | 中国药科大学 | Eucommia ulmoids leaf extracts and preparation method and application thereof |
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Application publication date: 20140212 |