CN106928290A - A kind of preparation method of high content rutin - Google Patents
A kind of preparation method of high content rutin Download PDFInfo
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- CN106928290A CN106928290A CN201710119884.6A CN201710119884A CN106928290A CN 106928290 A CN106928290 A CN 106928290A CN 201710119884 A CN201710119884 A CN 201710119884A CN 106928290 A CN106928290 A CN 106928290A
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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 discloses a kind of preparation method of high content rutin, belong to field of pharmaceutical chemistry technology.Technical scheme main points are：A kind of preparation method of high content rutin, concretely comprises the following steps：Crude product rutin is dissolved in the aqueous solution of alkali；Kieselguhr adsorption, and suction filtration while hot are added after heating for dissolving；Filtrate acid solution regulation pH value is 37；Cooling stands crystallization；Suction filtration obtains high content rutin.The present invention uses water as solvent, environmental protection；The rutin purity for obtaining can reach 99.0 more than %；The method gained rutin yield is higher, is stably held in the % of 93 % 96, produces the production cost of the cost well below high content rutin in having reported patent and document of rutin, is suitable to commercial application.
Description
Technical field
The invention belongs to field of pharmaceutical chemistry technology, and in particular to a kind of preparation method of high content rutin.
Background technology
Rutin（Rutin）Rutin sophorin or rue leaf glycosides, citrin are called, in yellow or yellow greenish powder or superfine micropin
Shape is crystallized；Odorless, it is tasteless；Chance light is perishable, and color is gradually deepened in atmosphere, and molecular formula is C27H30O16, CAS NO. 153-
18-4, molecular weight is 610.51, and fusing point is 190-192 DEG C, and structural formula is as follows：
Rutin is a kind of very wide flavone compound of originating, and with the effect for reducing capillary permeability and fragility, is kept
And recover the normal elasticity of capillary；Clinically be used for prevent and treat cerebral hemorrhage, hypertension, diabetes, retinal hemorrhage, purpura and
Acute hemorrhagic ephritis etc.；It also is used as food antioxidant and pigment；There is preferable radioresistance, Green Tea Extract to make to skin
With, there is extremely strong absorption to ultraviolet and X-ray, as natural sun-screening agents, the rutin of 10wt% is added, ultraviolet
Absorptivity is up to 98 %；Effect with apparent scavenger-cell active oxygen radical.Pharmaceuticals industry is with rutin both at home and abroad
The medicines such as raw material production rutin tablets, Troxerutin, rutin magnesium chromic salts, multivita-glucose hydroxyl fourth rutin and Quercetin, expand reed
The range of application of fourth and market.
Rutin is soluble in boiling methyl alcohol, is dissolved in hot ethanol, alkaline solution, is slightly soluble in hot water and cold methanol, insoluble in cold water, second
Alcohol, chloroform, petroleum ether, acetoneand ethyl acetate.Rutin is widely present in the sophora bud（The bud of sophora flower）, buckwheat, rue, sea-buckthorn,
In the various plants such as hawthorn, eucalyptus leaves and tobacco leaf, wherein the content highest in the sophora bud, buckwheat, eucalyptus leaves, can be used as extraction rutin
Raw material.Additionally, it be also present in holly plant ilex pubescens, the oleaceae plant capsule of weeping forsythia, the legume Fructus Sophorae and tobacco,
In the plants such as jujube, apricot, orange peel and tomato.
At present, the rutin production of China is mainly extracted by raw material of the sophora bud.Because rutin is soluble in alkali lye, after acid adding
Separate out, therefore, extract rutin in laboratory and enterprise's production and often use alkali extraction and acid precipitation.Due to there are a large amount of flavonoids things in the sophora bud
Matter, and structure is similar with rutin, therefore the extraction rutin method of routine is difficult to reach rutin content very high, HPLC contents are generally
90 % -95 %, the presence of impurity will influence rutin bulk drug quality and the song prepared as raw material with rutin in crude product rutin
The quality of gram rutin, therefore prepare the rutin of high content and be particularly important.
Rutin process for purification has following several：（1）Zhao Wenbin etc. reports the method for using molecular size separate, by rutin
After being dissolved with methyl alcohol, sephadex capital is added, eluted with methyl alcohol, collect methanol solution, concentration, crystallization.Principle is due to big
Molecule can not enter inside sephadex, thus first be eluted, and be eluted after small molecule, so as to by molecular size it is different into
Get separation.（2）King's thickness congruence is reported using rutin is dissolved with alcohol at room temperature, and filtering, filtrate places crystallization, and mother liquor is dense
Crystallization obtains high content rutin again after contracting.The two-dimension plane structure of rutin is changed into 3-D solid structure by the method, favorably
Enter in solvent molecule, increase dissolubility, some impurity that alcohol is dissolved in after heating can be removed.（3）The report such as Shen Jihong uses three
The de- albumen of chloroacetic acid method and the Sevage methods of improvement take off albumen to purify rutin, and the method is simple to operate, save labour, but institute
It is higher with reagent toxicity, and purity is only 90 %, it is difficult to meet the current demand to high content rutin.（4）Qian Yuanhua etc. is reported
Road uses high-speed countercurrent chromatography purifying high-purity rutin, is characterized in using aqueous, polynary organic solvent system, using at a high speed
The characteristics of adverse current chromatogram is without Irreversible Adsorption, the rate of recovery high and separative efficiency high, is refining to obtain high content rutin.The method is made
Standby rutin purity uses various organic solvents up to 98 more than %, there is certain influence on environment, while it is prepared only gram
Magnitude, it is relatively costly, it is unfavorable for industrialized production.（5）Liu Zhiqiang carries out column chromatography refined rutin using resin, and the method is by institute
Rutin deionized water drip washing is obtained, 10-14 h is dried under the conditions of 80-90 DEG C, because being dried for a long time under higher temperature
Especially have and the oxidation or decomposition of part rutin easily occur in the presence of air or illumination, therefore there is certain defect.
In having been reported, the refined purity of rutin up to 98 more than % method, or need chromatography, it is cumbersome；
Using excessive poisonous organic solvent, it is unfavorable for environmental protection；Or high cost is not suitable for industrialization.
The content of the invention
Present invention solves the technical problem that there is provided a kind of preparation method of high content rutin, diatom is found by experiment that
Soil has preferable adsorption capacity to rutin impurity, and effect uses the method better than adsorptive agents such as activated carbon, hydroxyapatites
The rutin of preparation has the advantages that high income, purity are high, step is easy, with low cost, economic and environment-friendly and suitable for industrialization, is
A kind of process for purification with industrial production value.
The present invention is to solve above-mentioned technical problem to adopt the following technical scheme that, a kind of preparation method of high content rutin, its
It is characterised by concretely comprising the following steps：
（1）Crude product rutin is dissolved in the aqueous solution of alkali；
（2）Kieselguhr adsorption, and suction filtration while hot are added after heating for dissolving；
（3）Filtrate acid solution regulation pH value is 3-7；
（4）Cooling stands crystallization；
（5）Suction filtration obtains high content rutin.
Further preferably, step（1）Described in crude product rutin be commercially available common rutin, its HPLC content be 92-95
%。
Further preferably, step（1）Described in alkali be NaOH, potassium hydroxide, sodium methoxide, caustic alcohol or potassium ethoxide
In one or more.
Further preferably, step（1）Described in alkali aqueous solution reclaimed water volume and crude product rutin ratio for 15-
25 L :1 Kg, alkali and the mol ratio of crude product rutin are 0.5-2 in the aqueous solution of alkali: 1.
Further preferably, step（2）Heating-up temperature in middle heating for dissolving process is 60-100 DEG C.
Further preferably, step（2）Described in diatomaceous consumption for crude product rutin quality 2 % -10 %.
Further preferably, step（3）Described in acid solution be one or more in hydrochloric acid, sulfuric acid, nitric acid or acetic acid.
The present invention has advantages below compared with prior art：The present invention uses water as solvent, environmental protection；The reed for obtaining
Fourth purity can reach 99.0 more than %；The method gained rutin yield is higher, is stably held in 93 % -96 %, produces rutin
Production cost of the cost well below high content rutin in having reported patent and document, be suitable to commercial application.
Specific embodiment
The above of the invention is described in further details by the following examples, but this should not be interpreted as this
The scope for inventing above-mentioned theme is only limitted to following embodiment, and all technologies realized based on the above of the present invention belong to this hair
Bright scope.
Embodiment 1
By in 264 g (6.6 mol) NaOH, 30 L distilled water of addition, stirring and dissolving adds 2 Kg's (3.3 mol)
Crude product rutin, 90 stirrings add 100 g diatomite, while hot suction filtration, the filtrate clarified to dissolving.By the filtrate hydrochloric acid
Regulation pH to 5.0.Slow cooling to room temperature, temperature fall time is controlled in 3 h, and 4 h are stood at room temperature, and suction filtration, filter cake is drenched with 4 L water
Wash, the % of yield 95.1, the % of purity 99.0.
Embodiment 2
By in 185 g (3.3 mol) potassium hydroxide, 40 L distilled water of addition, stirring and dissolving adds 2 Kg's (3.3 mol)
Crude product rutin, 80 DEG C of stirrings add 160 g diatomite, while hot suction filtration, the filtrate clarified to dissolving.By the filtrate salt
Acid for adjusting pH is to 5.0.Slow cooling to room temperature, temperature fall time is controlled in 3 h, and 4 h, suction filtration, 14 L of filter cake are stood at room temperature
Water wash, the % of yield 95.2, the % of purity 99.2.
Embodiment 3
By in 132 g (3.3 mol) NaOH, 50 L distilled water of addition, stirring and dissolving adds 2 Kg's (3.3 mol)
Crude product rutin, 100 DEG C of stirrings add 40 g diatomite, while hot suction filtration, the filtrate clarified to dissolving.By the filtrate nitre
Acid for adjusting pH is to 3.0.Slow cooling to room temperature, temperature fall time is controlled in 3 h, and 4 h, suction filtration, 20 L of filter cake are stood at room temperature
Water wash, the % of yield 94.3, the % of purity 99.3.
Embodiment 4
By in 265 g (4.9 mol) sodium methoxide, 40 L distilled water of addition, stirring and dissolving adds the thick of 2 Kg (3.3 mol)
Product rutin, 75 DEG C of stirrings add 200 g diatomite, while hot suction filtration, the filtrate clarified to dissolving.By the filtrate hydrochloric acid
Regulation pH to 7.0.To room temperature, temperature fall time is controlled in 3 h slow cooling, stands 4 h at room temperature, suction filtration, and filter cake is with 14 L water
Drip washing, the % of yield 95.0, the % of purity 99.8.
Embodiment 5
By in 198 g (4.9 mol) NaOH, 30 L distilled water of addition, stirring and dissolving adds 2 Kg's (3.3 mol)
Crude product rutin, 90 DEG C of stirrings add 160 g diatomite, while hot suction filtration, the filtrate clarified to dissolving.By the filtrate salt
Acid for adjusting pH is to 6.0.Slow cooling to room temperature, temperature fall time is controlled in 3 h, and 4 h, suction filtration, 10 L of filter cake are stood at room temperature
Water wash, the % of yield 94.8, the % of purity 99.3.
Embodiment 6
By in 264 g (6.6 mol) NaOH, 40 L distilled water of addition, stirring and dissolving adds 2 Kg's (3.3 mol)
Crude product rutin, 100 DEG C of stirrings add 160 g diatomite, while hot suction filtration, the filtrate clarified to dissolving.The filtrate is used
Sulphur acid for adjusting pH is to 5.0.Slow cooling to room temperature, temperature fall time is controlled in 3 h, and 4 h are stood at room temperature, and suction filtration, filter cake uses 10
L water wash, the % of yield 93.1, the % of purity 99.2.
Embodiment 7
By in 66 g (1.6 mol) NaOH, 50 L distilled water of addition, stirring and dissolving adds 2 Kg's (3.3 mol)
Crude product rutin, 60 DEG C of stirrings add 200 g diatomite, while hot suction filtration, the filtrate clarified to dissolving.By the filtrate vinegar
Acid for adjusting pH is to 6.0.Slow cooling to room temperature, temperature fall time is controlled in 3 h, and 4 h, suction filtration, 20 L of filter cake are stood at room temperature
Water wash, the % of yield 93.9, the % of purity 99.1.
Embodiment 8
By in 198 g (4.9 mol) NaOH, 40 L distilled water of addition, stirring and dissolving adds 2 Kg's (3.3 mol)
Crude product rutin, 60 DEG C of stirrings add 100 g diatomite, while hot suction filtration, the filtrate clarified to dissolving.By the filtrate salt
Acid for adjusting pH is to 5.0.Slow cooling to room temperature, temperature fall time is controlled in 3 h, and 4 h, suction filtration, 20 L of filter cake are stood at room temperature
Water wash, the % of yield 94.8, the % of purity 99.4.
Embodiment 9
By in 264 g (6.6 mol) NaOH, 50 L distilled water of addition, stirring and dissolving adds 2 Kg's (3.3 mol)
Crude product rutin, 90 DEG C of stirrings add 200 g diatomite, while hot suction filtration, the filtrate clarified to dissolving.By the filtrate salt
Acid for adjusting pH is to 6.0.Slow cooling to room temperature, temperature fall time is controlled in 3 h, and 4 h, suction filtration, 20 L of filter cake are stood at room temperature
Water wash, the % of yield 94.4, the % of purity 99.8.
Embodiment 10
By in 264 g (6.6 mol) NaOH, 50 L distilled water of addition, stirring and dissolving adds 2 Kg's (3.3mol)
Crude product rutin, 90 DEG C of stirrings add 200 g activated carbons, while hot suction filtration, the filtrate clarified to dissolving.By the filtrate salt
Acid for adjusting pH is to 6.0.Slow cooling to room temperature, temperature fall time is controlled in 3 h, and 4 h, suction filtration, 20 L of filter cake are stood at room temperature
Water wash, the % of yield 90.0, the % of purity 94.2.
Embodiment 11
By in 264 g (6.6 mol) NaOH, 50 L distilled water of addition, stirring and dissolving adds 2 Kg's (3.3 mol)
Crude product rutin, 90 DEG C of stirrings add 200 g hydroxyapatites, while hot suction filtration, the filtrate clarified to dissolving.By the filtrate
With nitre acid for adjusting pH to 6.0.Slow cooling to room temperature, temperature fall time is controlled in 3 h, and 4 h are stood at room temperature, and suction filtration, filter cake is used
20 L water wash, the % of yield 90.0, the % of purity 93.5.
Embodiment above describes general principle of the invention, principal character and advantage, the technical staff of the industry should
Understand, the present invention is not limited to the above embodiments, simply original of the invention is illustrated described in above-described embodiment and specification
Reason, under the scope for not departing from the principle of the invention, various changes and modifications of the present invention are possible, and these changes and improvements each fall within
In the scope of protection of the invention.
Claims (7)
1. a kind of preparation method of high content rutin, it is characterised in that concretely comprise the following steps：
（1）Crude product rutin is dissolved in the aqueous solution of alkali；
（2）Kieselguhr adsorption, and suction filtration while hot are added after heating for dissolving；
（3）Filtrate acid solution regulation pH value is 3-7；
（4）Cooling stands crystallization；
（5）Suction filtration obtains high content rutin.
2. the preparation method of high content rutin according to claim 1, it is characterised in that：Step（1）Described in crude product
Rutin is commercially available common rutin, and its HPLC content is 92-95 %.
3. the preparation method of high content rutin according to claim 1, it is characterised in that：Step（1）Described in alkali be
One or more in NaOH, potassium hydroxide, sodium methoxide, caustic alcohol or potassium ethoxide.
4. the preparation method of high content rutin according to claim 1, it is characterised in that：Step（1）Described in alkali
The volume of aqueous solution reclaimed water is 15-25 L with the mass ratio of crude product rutin:1 Kg, alkali and crude product rutin in the aqueous solution of alkali
Mol ratio be 0.5-2: 1.
5. the preparation method of high content rutin according to claim 1, it is characterised in that：Step（2）Middle heating for dissolving mistake
Heating-up temperature in journey is 60-100 DEG C.
6. the preparation method of high content rutin according to claim 1, it is characterised in that：Step（2）Described in diatom
The consumption of soil is 2 % -10 % of crude product rutin quality.
7. the preparation method of high content rutin according to claim 1, it is characterised in that：Step（3）Described in it is sour molten
Liquid is one or more in hydrochloric acid, sulfuric acid, nitric acid or acetic acid.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108329369A (en) * | 2018-04-08 | 2018-07-27 | 河南师范大学 | A kind of preparation method of high-content rutin |
| CN115010776A (en) * | 2022-06-24 | 2022-09-06 | 山西龙荞生物科技有限公司 | Method for extracting buckwheat rutin |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1410423A (en) * | 2001-09-28 | 2003-04-16 | 张杰克 | Technical method of extracting rutin |
| CN101045720A (en) * | 2007-03-20 | 2007-10-03 | 陕西师范大学 | Method for extracting buckwheat flavone from buckwheat shell |
| CN103833808A (en) * | 2013-12-03 | 2014-06-04 | 西安应化生物技术有限公司 | Method for extraction separation of rutin of tartary buckwheat |
| CN106397513A (en) * | 2016-10-27 | 2017-02-15 | 广西禅方药业股份有限公司 | Method for refining rutin having content more than or equal to 98% |
-
2017
- 2017-03-02 CN CN201710119884.6A patent/CN106928290B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1410423A (en) * | 2001-09-28 | 2003-04-16 | 张杰克 | Technical method of extracting rutin |
| CN101045720A (en) * | 2007-03-20 | 2007-10-03 | 陕西师范大学 | Method for extracting buckwheat flavone from buckwheat shell |
| CN103833808A (en) * | 2013-12-03 | 2014-06-04 | 西安应化生物技术有限公司 | Method for extraction separation of rutin of tartary buckwheat |
| CN106397513A (en) * | 2016-10-27 | 2017-02-15 | 广西禅方药业股份有限公司 | Method for refining rutin having content more than or equal to 98% |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108329369A (en) * | 2018-04-08 | 2018-07-27 | 河南师范大学 | A kind of preparation method of high-content rutin |
| CN108329369B (en) * | 2018-04-08 | 2021-02-12 | 河南师范大学 | Preparation method of high-content rutin |
| CN115010776A (en) * | 2022-06-24 | 2022-09-06 | 山西龙荞生物科技有限公司 | Method for extracting buckwheat rutin |
| CN115010776B (en) * | 2022-06-24 | 2024-04-19 | 山西助潞腾飞数智科技有限公司 | Extraction method of tartary buckwheat rutin |
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