CN101851221B - Method for preparing dihydroquercetin from larches - Google Patents
Method for preparing dihydroquercetin from larches Download PDFInfo
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- CN101851221B CN101851221B CN201010184375XA CN201010184375A CN101851221B CN 101851221 B CN101851221 B CN 101851221B CN 201010184375X A CN201010184375X A CN 201010184375XA CN 201010184375 A CN201010184375 A CN 201010184375A CN 101851221 B CN101851221 B CN 101851221B
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- taxifoliol
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Abstract
The invention relates to a method for preparing dihydroquercetin from larches, which is characterized by comprising the following steps: carrying out reflux extraction on larch wood flour as raw material by using an alcohol solution for one time and filtering to obtain an extraction liquid; adding strong acid ion exchange resin and a chlorinated solvent to the extraction liquid; carrying out reflux hydrolysis to convert bound dihydroquercetin into free dihydroquercetin; separating a chlorinated solvent phase after the reaction is ended; concentrating to dryness; and recrystallizing to obtain the product. The operation process is mainly characterized in that the energy consumption is less, the hydrolysis and the extraction are simultaneously completed, the production cost is low and the yield is high; the catalytic hydrolysis process of the strong acid ion exchange resin does not generate pollution, and all solvents can be recycled, and thereby, the industrial scale production becomes convenient.
Description
Affiliated technical field:
The present invention relates to the natural product chemistry field, particularly relate to a kind of method that from tamarack, prepares Taxifoliol,
Background technology:
Taxifoliol is a kind of important flavanone alcohol compound that occurring in nature exists, and also claims vitamin P, has the woods source activity material of multiple important BA.Pure article are pale yellow powder; Has superpower resistance of oxidation; Play a part specially keeping human recycle system's function aspects, it is because of having anticancer, reduce fat, protection cardiovascular and cerebrovascular, liver; Visual function, and, anti-oxidant, delay senility, diminish inflammation and a series of effect such as anti-diabetic and receiving much concern.
The content of Taxifoliol in tamarack is about about 0.3～5.7%, and Taxifoliol is extracted from confierophyte Chamaecyparis obtusa (Sieb.et Zucc.) Endl. leaf by Japanese scholar Fukui the earliest, is a kind of aglycon of glucoside.Subsequently he studied it again distribution and the bacterium of 3-O-glucoside in confierophyte in the presence of the hydrolysis of glycosidic bond.There is the people from various plants, to isolate Taxifoliol and verivate thereof later on again, in plant, exists with aglycon or two kinds of forms of glycosides.
USP (US2744919A) has introduced water or big slightly alcohol or the ketone of polarity extracts Taxifoliol from bark; The concentrating under reduced pressure solvent obtains a kind of crude extract that contains tannin, carbohydrate and coloring matter; Then with low polar alcohol, ketone or ether extraction, remove paste behind the solvent and carry out crystallization purifying with hot water and make the Taxifoliol bullion.The medicinal extract solution that obtains after this method SX contains more impurity, improves not obvious and the crystallization number of times is more at crystalline process moderate purity.
Canadian Patent (CA532804A) has been introduced with hot water and from bark, has been extracted Taxifoliol; Cool off centrifugal after-filtration; Concentrate and obtain a kind of crude extract that contains tannin, carbohydrate and coloring matter; Then with low polar alcohol, ketone or ether extraction, remove paste behind the solvent and carry out crystallization purifying with hot water and make the Taxifoliol bullion.Because this method adopts hot water extraction, so the solvent recuperation cost is higher.
It is the method that raw material extracts Taxifoliol with the tamarack wood powder that Russ P (RU2184561C1) has been introduced a kind of; With wood powder and organic solvent Hybrid Heating to 110～120 ℃ extraction; Cooled and filtered, the concentrating under reduced pressure solvent is straight 10%, regulates filtrating pH value straight 5～6; 90～98 ℃ of heating make glycosides be hydrolyzed to the form of aglycon, and crystallization obtains thick product under acidic conditions then.Though this method has improved the yield of Taxifoliol, do not pass through extracting operation, the purity after the very difficult raising crystallization.
Publication number is that the Chinese patent of CN1844095 has been introduced a kind of method of from tamarack, extracting Taxifoliol; This method is extraction agent with water; Larch in Xinanlin area to containing Taxifoliol is extracted; Aqueous extraction liquor to gained is that extraction agent carries out liquid-liquid extraction with the MTBE; Adopt gac or atlapulgite that the MTBE extraction liquid is carried out adsorption bleaching, the back MTBE extraction liquid that decolours is carried out removing of solvent under vacuum condition, remove paste water behind the solvent and carry out crystallization purifying and make the Taxifoliol raw product.The used extraction solvent of this method is a MTBE, and price is expensive; And the decolorization of gac or atlapulgite is non-enclosed operating process, is not easy to continuity production.
Publication number is that the Chinese patent of CN1858046 has been introduced a kind of method that adopts absorption method from tamarack, to extract Taxifoliol; This method is extraction agent with water; Larch in Xinanlin area to containing Taxifoliol is extracted, and adopts gac or atlapulgite that extracting solution is decoloured, thereafter; Aqueous extraction liquor to gained uses polyamide powder to adsorb as sorbent material earlier; Carry out desorb with desorption solvent again, the gained stripping liquid carries out solvent removal under vacuum condition, the white or the little yellow powdered Taxifoliol raw product that obtain.This method adopts twice adsorption operations in leaching process, the enrichment of once decolouring has not only increased the cost of sorbent material, has also extended the production cycle, has increased extraction cost.
Publication number is that the Chinese patent of CN101333203 and CN101333204 has been introduced a kind of method that from the tamarack wood chip, prepares Taxifoliol, tamarack wood chip and ethanolic soln is joined in the extractor fully mix, and both add-ons are 50 kilograms of tamarack wood chips, 500～800 liters of 50% ethanolic solns; Extract after-filtration, through extracting merging filtrate for the second time; Organic solution is collected in extraction, extremely does with vacuum-evaporator underpressure distillation organic phase; Used hot water dissolving's residue in 10: 1 by weight, and used activated carbon decolorizing, crystallization under 3-5 ℃ of temperature; Separate out dihydro Quercetin product, be finished product through vacuum-drying, pulverizing again.The tamarack wood chip that this method is used causes the inconvenience of filter operation because particle is less and inhomogeneous; Because the wood chip lighter weight floats on the solvent top, in stirring and immersion process, needs to consume a large amount of solvents, has increased the burden of solvent recuperation for follow-up underpressure distillation.
Publication number be the patent of CN101054369 introduced a kind of from Folium Engelhardia roxburghina the method for extraction separation Taxifoliol, be raw material with the Folium Engelhardia roxburghina, through extract, concentrate, column chromatography, crystallization, hydrolysis, obtain a kind of needle crystal, the Taxifoliol of off-white color.The used column chromatography cost of this method is high, and the production cycle is long.
Summary of the invention:
The object of the present invention is to provide a kind of method that from tamarack, prepares Taxifoliol.
In order to achieve the above object, the technical scheme of the present invention's employing comprises: with the tamarack wood powder is raw material, with the ethanolic soln refluxing extraction once; Cross and filter extracting solution; Strong-acid ion exchange resin and chlorinated solvents are added in the extracting solution, and back hydrolysis makes the combined Taxifoliol be converted into the free state Taxifoliol, and reaction is isolated the chlorinated solvents phase after finishing; Be concentrated into driedly, obtain product behind the recrystallization.
Advantage of the present invention is:
1. adopt ion exchange resin to be used for combined Taxifoliol hydrolytic process as solid acid, efficient is high, than more environmental protection of liquid acid, is easy to realize cleaner production
2. hydrolysis is carried out with extraction simultaneously, has avoided the degraded of Taxifoliol because of strong acid condition effectively, saves the usage quantity of operation sequence and solvent, and production cost is low, and yield is high.
Embodiment:
Implement to describe in further detail in the face of the present invention down:
With the tamarack wood powder is raw material; With the ethanolic soln refluxing extraction once, cross and filter extracting solution, strong-acid ion exchange resin and chlorinated solvents are added in the extracting solution; Back hydrolysis makes the combined Taxifoliol be converted into the free state Taxifoliol; Isolate the chlorinated solvents phase after reaction finishes, be concentrated into driedly, obtain product behind the recrystallization.
It is 10%～85% that refluxing extraction is used the volume(tric)fraction of ethanolic soln, 75～90 ℃ of refluxing extraction temperature, 1～5 hour extraction time, solid-liquid ratio 1: 6～1: 20.
Hydrolysis can be a macroporous type with strong-acid ion exchange resin, also can be gel-type, preferred gel-type, and usage quantity is that hydrolysis temperature is 50～85 ℃, hydrolysis time 0.5～4 hour in 3～20% of tamarack raw material.
Chlorinated solvents is methylene dichloride, trichloromethane, 1,1-ethylene dichloride and 1, and the mixed solvent of a kind of or its arbitrary proportion in the 2-ethylene dichloride, the ratio of chlorinated solvents and extracting solution is 7: 3～3: 7.
Below, the present invention will further explain with embodiment, but it is not limited to embodiment or similar instance.
Embodiment:
The tamarack wood chip of 105g moisture 9.6% adds 1 liter of 50% ethanolic soln, 80 ℃ of refluxing extraction 4h, and cold filtration, the concentration of Taxifoliol is about 0.017mg/mL in the filtrating; Add 10g 201 * 7 strongly acidic cationic exchange resins, add then isopyknic 1,80 ℃ of heating hydrolysis 2h of 2-ethylene dichloride; Reaction finishes postcooling, separates 1,2-ethylene dichloride phase; Reclaim 1, the 2-ethylene dichloride gets liquid dope 2.56g, and Taxifoliol content is 32.6%.
Claims (5)
1. method that from tamarack, prepares Taxifoliol, it is characterized in that: with the tamarack wood powder is raw material, with the ethanolic soln refluxing extraction once; Cross and filter extracting solution, strong-acid ion exchange resin and chlorinated solvents are added in the extracting solution, back hydrolysis makes the combined Taxifoliol be converted into the free state Taxifoliol; Reaction is isolated the chlorinated solvents phase after finishing; Be concentrated into driedly, obtain product behind the recrystallization, chlorinated solvents is 1; 1-ethylene dichloride and 1, the mixed solvent of a kind of or its arbitrary proportion in the 2-ethylene dichloride.
2. according to the described a kind of method that from tamarack, prepares Taxifoliol of claim 1, it is characterized in that: it is 10%～85% that refluxing extraction is used the volume(tric)fraction of ethanolic soln.
3. according to the described a kind of method that from tamarack, prepares Taxifoliol of claim 1, it is characterized in that: 75～90 ℃ of refluxing extraction temperature, 1～5 hour extraction time, solid-liquid ratio 1: 6～1: 20.
4. according to the described a kind of method that from tamarack, prepares Taxifoliol of claim 1; It is characterized in that: hydrolysis can be a macroporous type with strong-acid ion exchange resin; It also can be gel-type; Usage quantity is that hydrolysis temperature is 50～85 ℃, hydrolysis time 0.5～4 hour in 3～20% of tamarack raw material.
5. according to the described a kind of method that from tamarack, prepares Taxifoliol of claim 1; It is characterized in that: chlorinated solvents is 1; 1-ethylene dichloride and 1, the mixed solvent of a kind of or its arbitrary proportion in the 2-ethylene dichloride, the ratio of chlorinated solvents and extracting solution is 7: 3～3: 7.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201010184375XA CN101851221B (en) | 2010-05-27 | 2010-05-27 | Method for preparing dihydroquercetin from larches |
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| CN201010184375XA CN101851221B (en) | 2010-05-27 | 2010-05-27 | Method for preparing dihydroquercetin from larches |
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| CN101851221A CN101851221A (en) | 2010-10-06 |
| CN101851221B true CN101851221B (en) | 2012-09-05 |
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Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101863869A (en) * | 2010-06-03 | 2010-10-20 | 东北林业大学 | Method for extracting dihydroquercetin from larch sheets |
| CN101993429A (en) * | 2010-12-08 | 2011-03-30 | 天津市尖峰天然产物研究开发有限公司 | Method for extracting dihydroquercetin from larch sawdust |
| RU2451506C1 (en) * | 2011-06-02 | 2012-05-27 | Сергей Юрьевич Лешков | Combination for treatment of diabetes and complications thereof |
| CN102924420B (en) | 2012-10-25 | 2013-09-04 | 沈立乾 | Method for extracting dihydroquercetin from root of dahurian larch |
| CN108524313A (en) * | 2018-07-02 | 2018-09-14 | 吉林农业科技学院 | Dihydroquercetin skin care skin-lightening cosmetic |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2744919A (en) * | 1952-09-09 | 1956-05-08 | Ervin F Kurth | Producing pure dihydroquercetin |
| CA532804A (en) * | 1956-11-06 | F. Kurth Ervin | Producing pure dihydroquercetin | |
| CN1844095A (en) * | 2006-04-29 | 2006-10-11 | 广州大学 | Method for extracting dihydro-quercetin from larch |
| CN1858046A (en) * | 2006-06-02 | 2006-11-08 | 广州大学 | Method for extracting dihydro quercetin from larch using adsorption method |
| CN101054369A (en) * | 2007-06-05 | 2007-10-17 | 宋云飞 | Method of extracting and separating dihydroquercetin from roxburgh engelhardtia leaf |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007509918A (en) * | 2003-10-30 | 2007-04-19 | リピッド ニュートリション ベスローテン フェンノートシャップ | Pine needle extract |
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- 2010-05-27 CN CN201010184375XA patent/CN101851221B/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA532804A (en) * | 1956-11-06 | F. Kurth Ervin | Producing pure dihydroquercetin | |
| US2744919A (en) * | 1952-09-09 | 1956-05-08 | Ervin F Kurth | Producing pure dihydroquercetin |
| CN1844095A (en) * | 2006-04-29 | 2006-10-11 | 广州大学 | Method for extracting dihydro-quercetin from larch |
| CN1858046A (en) * | 2006-06-02 | 2006-11-08 | 广州大学 | Method for extracting dihydro quercetin from larch using adsorption method |
| CN101054369A (en) * | 2007-06-05 | 2007-10-17 | 宋云飞 | Method of extracting and separating dihydroquercetin from roxburgh engelhardtia leaf |
Non-Patent Citations (2)
| Title |
|---|
| 王宇等.落叶松中二氢槲皮素提取工艺研究.《食品科学》.2009,第30卷(第24期),第141-143页. * |
| 金建忠等.落叶松中二氢槲皮素的提取及鉴定.《浙江林业科技》.2004,第24卷(第5期),第15-17页. * |
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Granted publication date: 20120905 Termination date: 20130527 |