CN101070281A - Method of distilling shikimic acid from plants selectively - Google Patents
Method of distilling shikimic acid from plants selectively Download PDFInfo
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- CN101070281A CN101070281A CNA2006100642437A CN200610064243A CN101070281A CN 101070281 A CN101070281 A CN 101070281A CN A2006100642437 A CNA2006100642437 A CN A2006100642437A CN 200610064243 A CN200610064243 A CN 200610064243A CN 101070281 A CN101070281 A CN 101070281A
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Abstract
The invention relates to a preparation method of shikimic acid from plants containing shikimic acid, which comprises: a) repeatedly extracting comminuted plants by polar solvents except water; b) filtrating extracts of step a), associating and concentrating; c) concentrating the extracts of step b) rich of shikimic acid by non-polar solvent; d) separating shikimic acid from the extracts of step c) by polar solvent.
Description
Technical field
The present invention relates to a kind of from plant, the method for from happiness horse anise, separating important pharmacy intermediate shikimic acid (shikimic acid) particularly.
Background technology
Shikimic acid (shikimic acid) is a kind of the have hydrogenation of six carbocyclic of height functionalization and attractive chiral synthon of a plurality of asymmetric centers.Its name derives from Japan's flower " Shikimi ", and it is separated from this spending first.As a kind of biosynthetic metabolism intermediate of die aromatischen Aminosaeuren that derives from, shikimic acid (shikimic acid) has become the synthetic necessary chirality starting raw material of the neural ammonia glycosides enzyme inhibitors [J.Am.Chem.Soc.119:681 (1997) that is used for the treatment of influenza; J.Org.Chem.63:4545 (1998)].Shikimic acid (shikimic acid) also is used for the intermediate of synthetic aroma compounds of group, as phenylalanine, tyrosine, tryptophane, p-aminobenzoic acid or p-hydroxy-benzoic acid.For example, acid catalyzed shikimic acid (shikimic acid) dehydration produces p-hydroxy-benzoic acid (Ber.Dtch.Chem.Ges.24:1278 (1891)), and it is to be used for used metagin of synthesizing liquid crystalline polymer and monomeric key precursor.Recently shikimic acid (shikimic acid) also is used as the starting point [J.Am.Chem.Soc.120:8565 (1998)] in the big composition data storehouse of synthetic molecules always.It also is a key intermediate in the biochemical route from the phosphoenolpyruvic acid to tyrosine.Shikimic acid (shikimic acid) is also as the starting raw material of many antimicrobial drugs, antifungal drug, weedicide with as nutrition agent.
Shikimic acid (shikimic acid) and derivative thereof are compounds known in the art, can be according to known method through corresponding cinchonic acid derivative, by for example [Angew.Chemie 83,329 (1971) with the POCl3 dehydration in pyridine; J.Am.Chem.Soc.95,7821 (1973); Chem.Ber.98,104 (1965)] or in pyridine, prepare with SO2C12 dehydration [WO 98/07685].
The patent No. is that 6,130,354 United States Patent (USP) has been described use Vilsmeier reagent and prepared the method for shikimic acid (shikimic acid) and derivative thereof by making the dehydration of cinchonic acid and derivative thereof.
One piece of author is people's such as Miles the Isolation﹠amp that is published in; Purification, Vol.2, pp, 75-82,1994 the article that is entitled as " Recovery of Shikimic Acid Using Temperature-Swing ComplexationExtraction and Displacement Back Extraction " discloses the method that shifts out shikimic acid (shikimic acid) from the aqueous solution.This method comprises uses trilaurylamine (Tridodecylamine solvent extraction that is dissolved in n-Heptyl alcohol (n-enanthol) or propyl carbinol (n-butanols) and the reextraction in water of using oleic acid to replace shikimic acid (shikimic acid) from organic phase.The document is devoted to set up a kind of general method that reclaims metabolism acid from fermention medium.
One piece is entitled as " The Biosynthesis and Synthesis of Shikimic Acid; Chorismis Acid andRelated Compounds ", the author is people's such as Campbell (in the February, 1993 that is published in Synthesis, pp.179-193) article, the compound of instruction except that glyphosate can disturb shikimic acid (shikimic acid) approach.The various difficult effort that this article is also described glucose deutero-shikimin approach in detail and made for chemosynthesis shikimic acid (shikimic acid).
Be entitled as " Chemical Synthesis of shikimic Acid and Its Analogues " at one piece, the author is Jiang etc., be published in Tetrahedron Report, Number449, Vol.54 (1998), in the publication of pp.4697-4753, the complexity of synthetic shikimic acid (shikimic acid) and analogue thereof is disclosed in detail and difficult task.Also fail to disclose the present invention with physiognomy such as Campbell with, people such as Jiang.
The method of known chemosynthesis shikimic acid (shikimic acid) produces many undesirable impurity or byproduct simultaneously, thereby and causes low yield or inferior quality or the two low shikimic acid (shikimic acid) of holding concurrently.Use the difficulty of the synthetic shikimic acid (shikimic acid) of habitual technical chemistry technology, part has hindered use shikimic acid (shikimic acid) and has prepared multiple pharmaceutically active compound.
Shikimic acid (shikimic acid) has the complicated chemical structure of many chiral centres.With the required higher cost of chemical process quality of production acceptable shikimic acid (shikimic acid), make that the medicament production that is made by these shikimic acids (shikimic acid) is very expensive.Relate to the multiple intermediate of handling enormous quantity owing to produce a large amount of shikimic acids (shikimic acid), this has also influenced production efficiency.Thereby press for exploitation and have the shikimic acid (shikimic acid) of pharmaceutically acceptable quality and be easy to the method that commercial size uses cheap effectively from plant, the separation.
Many medicinal plants have accumulated is enough to be used for economically various science, technology and the commercial applications large amount of organic matter as chemical feedstocks.Economical and practical organic substance can be used as the source of industry oil, resin, Weibull, saponin, natural rubber, natural gum, wax, dyestuff, medicine and multiple specific product.
In some medicinal plants of research, present inventor's distinct species in the Illicium plant of meeting unexpectedly is promptly liked the horse anise, and it has useful medical science characteristic, is a kind of natural origin of shikimic acid (shikimic acid).On classical India herbal medicine document being investigated (ayurvedic literature survey) and being cooperated, selected this plant species with by industry or commercial mass production shikimic acid (shikimic acid) with the basis of carrying out research so far.
Happiness horse anise is developed with its industrial medicinal and spices character.It is a kind of in the modal in the world existing Illicium plant.In Arunachal Pradesh (India), it is " Lissi " for local title.It is little tree to medium volume, be present in West Kameng, Taiwan, in Lohit and geographic subtropics of Lower Subansiri and the temperate zone broad-leaf forest, be distributed widely in Bomdila, West Kameng area [News Bull., State Forest Research Institute, 2003, p.26].The fruit of happiness horse anise is used for pharmacy and perfume industry.
Generally, the Illicium plant contains a large amount of dissimilar biological activity chemical ingredientss, and great majority contain many secondary plant metabolites [J Nat Prod. (1998), 61, the 230-236s relevant with the sesquiterpene lactones compound; Chem Pharm Bull (Tokyo) (2000), 48,657-659], sikimitoxin (anisatin), new sikimitoxin (neoanisatin) and pseudo-(pseudoanisatin) [Phytochemistry (1991), 30,251-353]; Anistree sikimitoxin (veranisatins) A, B and C[Chem Pharm Bull (Tokyo) (1993), 41,1670-1671]; 4-table-isopimaric acid, 8,11,13, trans (abietate the tran)-19-acid of 15-rosin ester, 15-hydroxyl dehydroabietic acid and β-Gu Zaichun [Zhongguo Zhong Yao Za Zhi (1996), 21 (9), 551-3,576]; 1-triacontanol price quote, thujin, shikimic acid (shikimic acid) [Zhongguo Zhong Yao Za Zhi (1989), 14 (1), 36-7,63]; Volatile oil such as oxygenate phenylpropionic acid class (phenylpropanoids) are safrole, 4-methoxy safrole [J.of Essential Oil Research, Jan/Feb.2005] basically; Monoterpenoid glucoside such as right
(p-menth)-1 (7), 4 (8)-diene-3-o-β-D-glucoside [Ina.J.Chemistry, 4lB (3), 2002,675-76], many glycosides and other activeconstituentss.
That the fruit of Illicium plant has is antibiotic, wind dispelling, diuresis, end toothache, excited and the character [The HerbBook, the Bantam books 1983 that are good for the stomach; Glossary of Indian Medicinal Plants, Council of Scienttficand Industrial Research, New Delhi, 1986].For oral administration can be used for treating stomachache, maldigestion and such as situation about being chief complaint with pain in the back.In its medicine through being common in maldigestion and cough mixture, to small part be because its that pleasant anisic fragrance.It is multiple digestive disorders, comprises effective medicine of acute abdomen, can be used safely in children [The Encyclopedia of Medicinal Plants DorlingKindersley.London 1996].Often chew this fruit in a small amount after the meal, with promoting digestion and fresh breath.Fruit has the anti-microbial effect similar to penicillin [Handbook of Chinese Herbs and Formulas.Institute of Chinese Medicine, Los Angeles 1985].When being used to chew, collecting fruit when prematurity, mature fruit is used to extract volatile oil and drying is used for decoction and pulvis.
The microchemistry of anistree (Illicium verum Hook) and Illicium religiosum Sieb. has been described in the prior art, but the seed of two kind of plant there is no and contains shikimic acid (shikimic acid) [Pharmazeutische Zentralhalle fuer Deutschland (1928), 69,581-5,601-5; AmericanJournal of Pharmacy (1835-1936) (1929), 101,550-74,622-37,687-716]].
From plant, make shikimic acid (shikimic acid) through tediously long multistep sepn process.Unfortunately, the difficulty [Haslem, E., ShikimicAcid.Metabolism and Metabolites, the Wiley ﹠amp that from the fruit of Illicium plant, separate shikimic acid (shikimic acid); Sons, New York, pp.40-42 (1993)] hindered its application in the kilogram level is synthetic.
Another difficulty that in from plant, extracting shikimic acid (shikimic acid) process, occurs be under the high temperature in leaching process water as the use of solvent.Because the high-k of water, many glycosides are extracted with shikimic acid (shikimic acid), separate shikimic acid (shikimic acid) on a large scale and become difficult from the glycoside mixture.
Shikimic acid (shikimic acid) is the precursor of multiple alkaloids, die aromatischen Aminosaeuren, phenylalanine, tyrosine, tryptophane, Weibull, xylogen, indoles and indole derivatives.It is widely used as the chiral building block of medicine in synthetic.An example of finished product is antiviral drug GS4104, a kind of neural ammonia glycosides enzyme inhibitors that is used for the treatment of and prevents A type influenza and Type B influenza.
As described above, have many shortcomings in the method for prior art, therefore, need a kind of cheapness, effectively, be of value to the method from plant selective extraction shikimic acid (shikimic acid) that can be used for industrial-scale production of environment.
In view of above-mentioned some, inventor of the present invention has set up a kind of industrial advantageous method of separating shikimic acid (shikimic acid) from plant.
Summary of the invention
One aspect of the present invention provides a kind of from the known method of separating shikimic acid (shikimic acid) the plant of shikimic acid (shikimic acid) that contains, and this method comprises:
A) extract comminuted plants composition partly repeatedly with the polar solvent beyond dewatering
B) extract with step a) filters, and mixing also concentrates
C) use non-polar solvent, make the extract of step b) be rich in shikimic acid (shikimic acid)
D) use polar solvent, from the extract of step c), separate shikimic acid (shikimic acid).
" plant " herein is meant that whole or arbitrary parts of plant contain any plant of shikimic acid (shikimic acid).The mixture of the plant of these kinds or plant part can be used for this purpose.Plant can be the mixture of draft, shrub, arbor (tree), or the mixture after its pulverizing.Preferably, the plant that is used in this respect is an Illicium.Preferred plant is a happiness horse anise.
The term of this paper " room temperature " is meant 20-25 ℃ temperature range.
Comminuted plants part or plant are all extracted with polar solvent.If desired, extract repeatedly.
Above used polar solvent is any polar solvent or its mixture in addition that dewater known to those skilled in the art in the prior art.The polar solvent that preferably is used to extract purpose is the primary alconol that 1-6 carbon is arranged.More preferably, extract with methyl alcohol.
Temperature range in the plant selective extraction is an important factor of the present invention.Extraction can be carried out to the boiling temperature of extracting used organic solvent at 20 ℃.Preferably, being extracted in 20 ℃-40 ℃ carries out.
After plant being extracted repeatedly, the mixture that at every turn extracts the merging of gained is filtered with polar solvent.Under suitable temperature, filtrate is concentrated into paste.The characteristic of solvent for use is depended in the selection of temperature.The minimum temperature in this stage remains on 35 ℃.
The lotion that is obtained by method as described above is cooled to room temperature.This lotion contains that oneself knows is present in polarity and nonpolar chemical composition in the plant.
By using non-polar solvent extract, remove the nonpolarity element in this lotion.
" non-polar solvent " above mentioned is meant any solvent known to those skilled in the art.Non-polar solvent is preferably selected from alkane, naphthenic hydrocarbon and/or cycloolefin.The solvent in this stage is selected from hexane and/or acetone.
In this extraction, temperature remains on the boiling range of solvent for use.
Non-polar solvent extracts nonpolarity element from extract.Filtering mixt discards filtrate.Clean residue extract (residue) repeatedly with non-polar solvent, thereby make the residue extract be rich in shikimic acid (shikimic acid).
Extract drying with the said process gained under the reflux temperature of solvent for use, is dissolved in the polar solvent then.Filtering solution is concentrated into 1/3rd of original volume, under freezing conditions preserves then 10-25 hour.The crystal of gained recrystallization from organic solvent obtains pure shikimic acid (shikimic acid).Used organic solvent is any conventional solvent.
The productive rate of the shikimic acid of Huo Deing (shikimic acid) is a 5.0%-10% weight like this, depends on the kind of used plant and the quality of raw material.
Another aspect of the present invention provides a kind of method for preparing shikimic acid (shikimic acid) from the Illicium plant, comprises
A) extract composition in the pulverizing seed of plant repeatedly with the polar solvent beyond dewatering
B) extract with step a) filters, merges and concentrates
C) make the extract of step b) be rich in shikimic acid (shikimic acid) with non-polar solvent
D) with polar solvent shikimic acid (shikimic acid) is separated from the extract of step c).
Above the described Illicium plant of Fa Ming second aspect refers to happiness horse anise, and preferably naming the people is Hook.f.﹠amp; The happiness horse anise of Thoms.
Used polarity and non-polar solvent be as described above in this respect in invention.Invent used in this respect polar solvent preferred alcohols, most preferably methyl alcohol.Used non-polar solvent is hexane and/or acetone in this respect.
The temperature that is kept during extraction depends on the character of solvent for use.The preferred room temperature of the temperature that is adopted.
From the Illicium plant, extract and describe with the method such as a first aspect of the present invention of separating shikimic acid (shikimic acid).
Aspect further, the present invention will provide a kind of method for preparing shikimic acid (shikimic acid) from the Illicium plant, comprising:
A) polar solvent beyond usefulness dewaters under the room temperature extracts the composition in the comminuted plants seed repeatedly
B) be to get thing to filter, merge and concentrate with step a)
C) make the extract of step b) be rich in shikimic acid (shikimic acid) with non-polar solvent
D) with polar solvent shikimic acid (shikimic acid) is separated from the extract of step c).
Above the described Illicium plant of Fa Ming the third aspect refers to happiness horse anise, and preferably naming the people is Hook.f.﹠amp; The happiness horse anise of Thoms.
Other characteristics of all of this aspect are similar to second aspect.
A fourth aspect of the present invention provides a kind of method for preparing shikimic acid (shikimic acid) from the Illicium plant, comprises
A) extract composition in the comminuted plants seed repeatedly with methyl alcohol under the room temperature
B) extract with step a) filters, merges and concentrates
C) with the nonpolarity element in hexane and/or the acetone removal step b) extract, make extract be rich in shikimic acid (shikimic acid)
D) from step c) extract obtained, separate shikimic acid (shikimic acid) with methyl alcohol
E) with polar solvent crystallisation step d) shikimic acid (shikimic acid) that makes.
Plant used herein " nonpolarity element " is meant that all are considered to be present in all nonpolarity elements in plant or the plant milk extract among the present invention.
Being used for the present invention's polar solvent in this respect is that above invention first aspect is described.
Every other feature in this respect is similar to first aspect.
A fifth aspect of the present invention provides a kind of method for preparing shikimic acid (shikimic acid) from the Illicium plant, comprises
A) extract composition in the comminuted plants seed repeatedly with non-polar solvent
B) the nonpolar extract that step a) is extracted each time filters, and discards filtrate, and residue contains the residue of undrawn polar component
C) in the residue of step b), add polar solvent repeatedly, extract the polar component in the residue
D) filtrate of extracting each time after the step c) is filtered, merged and concentrates
E) from the mixture that step d) generates, separate shikimic acid (shikimic acid) and make its crystallization.
Used in this respect herein non-polar solvent is described identical with first aspect present invention.Preferably, middle in this respect usefulness hexane is as non-polar solvent.
The temperature variation scope that is adopted during extraction is approximately 40 ℃-68 ℃.Preferably, keep during extraction homo(io)thermism about 65 ℃.
Herein, used in this respect polar solvent is except having got rid of described identical with first aspect present invention the restriction of water.Preferably, in this aspect, water is as polar solvent.
Be selective extraction polar component from the residue of step b), temperature becomes most important factor once more.In this respect, the variation of temperature scope is for approximately by 20 ℃ to about 80 ℃.Be selective extraction shikimic acid (shikimic acid) that temperature preferably remains on about room temperature.
Method institute's isolated shikimic acid (shikimic acid) crystallization from polar solvent in this respect, oneself describes in a first aspect of the present invention for this.Polar solvent particular methanol that crystallization is used and/or ethyl acetate or its mixing.
Polarity and nonpolarity element refer to that all are considered to be present in the composition in this plant, preferably those compositions well known in the prior art.
In the process of crystallization shikimic acid (shikimic acid), before freezing with standard shikimic acid (shikimic acid), inoculation time terminal mixture (penultimate mixture) is normally favourable.
In with the lower section, illustrate all respects of the present invention with the form of embodiment.Yet this is not to be intended to limit the scope of the invention by any way.Several conversion of these embodiment will be conspicuous to those skilled in the art.
Can for example use the patent No. to be US6 with the method that can from document, obtain by the neural ammonia glycosides enzyme inhibitors GS4104 of shikimic acid (shikimic acid) preparation, 518,048 or US6, the method that 403,824 U.S. Patent application is put down in writing.
Embodiment
Embodiment 1
From Illicium Griffithii Hook.F.﹠amp; Extract and the method for separating shikimic acid (shikimic acid) in the seed of Thoms
A) extracting method
To like that the anistree seed of horse (100Kg) is pulverized and the stainless steel extractor of the 1000L that packs in.Under the room temperature, extracted 15-16 hour continuous three times with methyl alcohol (400L).Extract is filtered and merging.The methanol extract that merges distills under condition of high vacuum degree in 50 ℃, is condensed into lotion.Collect lotion, room temperature cooling 3-4 hour.
B) remove nonpolarity element
To insert the stainless steel extractor of a 500L and to wherein adding acetone (60-65L) available from the cooling lotion of step a) above.Heat half an hour in 50 ℃.With the suspension filtered of gained, and clean residue (extract) with 15-20L acetone.
C) separate shikimic acid (shikimic acid)
With the residue drying of cleaning with acetone in the step b), under 50 ℃, be dissolved in methyl alcohol (35-40L) then.Solution filters, and by distillation, concentrated filtrate is to 1/3rd of its original volume.Enriched material was under freezing conditions preserved 15-20 hour.The filtering for crystallizing thing with its recrystallization from methyl alcohol, obtains pure shikimic acid (shikimic acid).
Productive rate: 4%-7% weight, depend on the quality of raw material
Purity: NLT 99.5% (HPLC records)
Embodiment 2
From the seed of happiness horse anise, extract and the method for separating shikimic acid (shikimic acid)
A) separate shikimic acid (shikimic acid)
With the crushed seeds of extracting section in the step a) of keeping somewhere in extractor, water (300L) extracted continuous three times 4 hours at 75 ℃.The water extract that merges is filtered, and concentrate under reduced pressure at low temperature is to former volumetrical 1/5.Spissated aqueous substance spends the night 10 ℃ of preservations.The material of gained filtered and from methyl alcohol or ethyl acetate recrystallization, obtain shikimic acid (shikimic acid).
Productive rate: 10.0% weight.
Embodiment 3
From the seed of happiness horse anise, extract and the method for separating shikimic acid (shikimic acid)
A) extracting method and removal nonpolarity element
The anistree seed of pulverizing of happiness horse (100kg) is packed in the 1000L stainless steel extractor.65 ℃ with hexane extraction 12-20 hour, continuous three times.Extract is merged and filtration.Filtrate is stored in the independent container.The pulverizing seed of extracting section is stayed in the extractor.
B) separate shikimic acid (shikimic acid)
With the pulverizing seed of extracting section in the step a) of keeping somewhere in extractor, at room temperature water (300L) extracted 12 hours, continuous three times.The aqueous extract that merges is filtered, be evaporated to 1/5 of original volume at 50 ℃.Spissated aqueous substance spends the night 10 ℃ of preservations.The material of gained filtered and from methyl alcohol or ethyl acetate recrystallization, obtain shikimic acid (shikimic acid).
Productive rate: 10.0% weight.
Claims (34)
1. method for preparing shikimic acid from the known plant that contains shikimic acid comprises:
A) extract comminuted plants composition partly repeatedly with the polar solvent beyond dewatering
B) extract with step a) filters, and merging also concentrates
C) use non-polar solvent, make the extract of step b) be rich in shikimic acid
D) use polar solvent, from the extract of step c), separate shikimic acid.
2. method according to claim 1, plant wherein is selected from the Illicium plant.
3. method according to claim 1, plant part wherein is a seed.
4. method according to claim 1, polar solvent wherein are alcohol.
5. method according to claim 4, alcohol wherein is methyl alcohol.
6. method according to claim 1, non-polar solvent wherein are selected from alkane, naphthenic hydrocarbon, cycloolefin, ketone and/or its mixture.
7. method according to claim 1, non-polar solvent wherein is an acetone.
8. method according to claim 1, non-polar solvent wherein is a hexane.
9. method for preparing shikimic acid from the Illicium plant comprises:
A. the polar solvent beyond usefulness dewaters extracts the composition in the comminuted plants seed repeatedly
B. the extract with step a) filters, merges and concentrates
C makes the extract of step b) be rich in shikimic acid with non-polar solvent
D separates shikimic acid with polar solvent from the extract of step c).
10. method according to claim 9, polar solvent wherein are alcohol.
11. method according to claim 10, alcohol wherein is methyl alcohol.
12. method according to claim 9, non-polar solvent wherein are selected from alkane, naphthenic hydrocarbon, cycloolefin, ketone or its mixture.
13. method according to claim 9, non-polar solvent wherein is an acetone.
14. method according to claim 9, non-polar solvent wherein is a hexane.
15. a method for preparing shikimic acid from the Illicium plant comprises:
A. the polar solvent beyond usefulness dewaters under the room temperature extracts the composition in the comminuted plants seed repeatedly
B. the extract with step a) filters, merges and concentrates
C makes the extract of step b) be rich in shikimic acid with non-polar solvent
D separates shikimic acid with polar solvent from the extract of step c).
16. method according to claim 15, polar solvent wherein are alcohol.
17. method according to claim 16, alcohol wherein is methyl alcohol.
18. method according to claim 15, non-polar solvent wherein are selected from alkane, naphthenic hydrocarbon, cycloolefin, ketone and/or its mixture.
19. method according to claim 15, non-polar solvent wherein is an acetone.
20. method according to claim 15, non-polar solvent wherein is a hexane.
21. a method for preparing shikimic acid from the Illicium plant comprises:
A. extract composition in the comminuted plants seed repeatedly with methyl alcohol under the room temperature
B. the extract with step a) filters, merges and concentrates
C makes the extract of gained be rich in shikimic acid with the nonpolarity element in hexane and/or the acetone removal step b) extract
D. from the extract that step c) obtains, separate shikimic acid with methyl alcohol
E. use polar solvent crystallisation step d) shikimic acid that makes.
22. method according to claim 21, polar solvent wherein are selected from alcohol, ester or its mixture.
23. method according to claim 22, alcohol wherein is methyl alcohol.
24. method according to claim 22, ester wherein is an ethyl acetate.
25. a method for preparing shikimic acid from the Illicium plant comprises:
A. extract composition in the comminuted plants seed repeatedly with non-polar solvent
B. the nonpolar extract that step a) is extracted each time filters, and discards filtrate, keeps the residue that contains undrawn polar component
C. in the residue of step b), add polar solvent repeatedly, extract the polar component in the residue
D. the filtrate of extracting each time after the step c) is filtered, merged and concentrates
E. from the mixture that step d) generates, separate shikimic acid and make its crystallization.
26. method according to claim 25, non-polar solvent wherein are selected from alkane, naphthenic hydrocarbon, cycloolefin, ketone and or its mixture.
27. method according to claim 25, non-polar solvent wherein is an acetone.
28. method according to claim 25, non-polar solvent wherein is a hexane.
29. method according to claim 25, polar solvent wherein are selected from alcohol, water or its mixture.
30. method according to claim 25, polar solvent wherein is a water.
31. crystallization obtains from alcohol, ester or its mixture for method according to claim 25, shikimic acid wherein.
32. method according to claim 31, alcohol wherein is methyl alcohol.
33. method according to claim 31, ester wherein is an ethyl acetate.
34. the purposes of the shikimic acid that from the seed of Illicium plant, extracts in preparation GS4104 compound.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN3419DE2005 | 2005-12-20 | ||
| IN3419/DEL/2005 | 2005-12-20 |
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| CN101070281A true CN101070281A (en) | 2007-11-14 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011110927A1 (en) * | 2010-03-12 | 2011-09-15 | Council Of Scientific & Industrial Research | A method for the extraction of shikimic acid |
| CN112094184A (en) * | 2019-06-17 | 2020-12-18 | 江苏得乐康生物科技有限公司 | Method for extracting shikimic acid from ginkgo leaf extract chromatographic wastewater |
-
2006
- 2006-12-20 CN CNA2006100642437A patent/CN101070281A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011110927A1 (en) * | 2010-03-12 | 2011-09-15 | Council Of Scientific & Industrial Research | A method for the extraction of shikimic acid |
| CN102791671A (en) * | 2010-03-12 | 2012-11-21 | 科学工业研究委员会 | A method for the extraction of shikimic acid |
| CN102791671B (en) * | 2010-03-12 | 2015-04-22 | 科学工业研究委员会 | A method for the extraction of shikimic acid |
| CN112094184A (en) * | 2019-06-17 | 2020-12-18 | 江苏得乐康生物科技有限公司 | Method for extracting shikimic acid from ginkgo leaf extract chromatographic wastewater |
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