CN101602768B - Method for purifying sesamin and sesamolin - Google Patents
Method for purifying sesamin and sesamolin Download PDFInfo
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- CN101602768B CN101602768B CN2009100654601A CN200910065460A CN101602768B CN 101602768 B CN101602768 B CN 101602768B CN 2009100654601 A CN2009100654601 A CN 2009100654601A CN 200910065460 A CN200910065460 A CN 200910065460A CN 101602768 B CN101602768 B CN 101602768B
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- sesamin
- sesamolin
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- ether
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Abstract
The invention relates to a method for purifying sesamin and sesamolin in sesame oil, which comprises the steps of: separating lignanoid compounds without fat constituents from the sesame oil first; adding ether into the lignanoid compounds to precipitate the sesamin; performing the filtration; dissolving an obtained filtrate by chloroform after concentration under reduced pressure, adding petroleum ether into the mixture until white opacity appears; heating and dissolving the obtained solution; and standing the obtained solution to precipitate the sesamolin. The method for purifying the sesamin and the sesamolin has the advantages of simple operation, safety, economization, strong process stability and the like, and is particularly suitable for industrialized application; and the method can synchronously obtain high-purity sesamin and sesamolin, and achieve the aim of comprehensive utilization.
Description
(1) technical field
The present invention relates to sesamin and the method for purification of sesamolin in a kind of til.
(2) background technology
Sesamin is a kind of lignan compounds that mainly is present in the sesame, and molecular formula is C
20H
18O
6, fusing point 121-123 ℃, its content accounts for the 0.2%-0.5% of sesame, and content is 0.5-1% in the non-til that bakes and handle without refinery practice, is one of important biological composition in the sesame.A large amount of experiment in vitro, experimentation on animals and clinical trial certificate sesamin have wide biological activity; It not only can protect and strengthen liver function, blood pressure regulation, reducing cholesterol; More can directly act on histoorgan, bring into play its excellent resistance of oxidation.Except studying its physiologically active and useful effect thereof, also there is the people to study to the sterilization effect of sesamin with to the stabilization of other food plant oil product composition to body health.Result of study shows, this natural plant composition of sesamin not only can be used as the sanitas that keeps flavour of food products, also can also can be developed into the natural drug of preventing and curing diseases as the healthy products and health products additive agent of enhancing body.
Sesamolin also is to be present in one of main lignan component in sesame and the til, and molecular formula is C
20H
18O
7, fusing point 93-94 ℃ is one of important biological composition in the sesame; Its content is only second to sesamin; Account for the 0.1-0.3% of sesame, content is 0.2-0.5% in the non-til that bakes and handle without refinery practice, is one of important biological composition in the sesame.Research shows that sesamolin has to be eliminated interior free yl, reduces SUV, enhancing body immunizing power, hypertension, antithrombotic, alleviation atherosclerosis in the serum, and the alcohol metabolism of promotion is arranged, strengthens detoxicating activity, anti-liver poisoning, suppresses numerous effects such as mammary cancer.Except itself has anti-oxidant activity, also can be converted into stronger sesamol of resistance of oxidation and sesamin phenol under certain condition, application prospect is very wide.
Contain more relatively sesamin and sesamolin in sesame and the til, but existing sophisticated technology of preparing can only obtain single sesamin, and it is still immature to prepare the technology of sesamolin simultaneously; Can be purified into the method technology very complicated of sesamin and sesamolin simultaneously; Particularly prepare the repeatedly column chromatography operation of highly purified sesamolin needs; And last purification phase is mostly used preparative high-performance liquid chromatographic method purifying; Obviously be inappropriate for suitability for industrialized production and use, this has also limited the exploitation of sesamolin related prods.
(3) summary of the invention
The object of the present invention is to provide the method for purification of a kind of sesamin and sesamolin, overcome existing method and can only obtain the defective that single active ingredient or purification process complicacy are inappropriate for industrial application.
The technical scheme that the present invention adopts is following:
The method of purification of a kind of sesamin and sesamolin separates obtaining the not Lignanoids compounds of fatty constituents earlier from til, add ether afterwards and separate out sesamin; Filter, the gained filtrate decompression concentrates the back and uses dissolved in chloroform, adds the muddy appearance of sherwood oil to adularescent then, leaves standstill after the heating for dissolving and separates out sesamolin.
The consumption of said ether is that every gram Lignanoids compounds adds 5-15mL.
Add ether and leave standstill and separates out sesamin, the described time of leaving standstill is 0.5-24h, dwell temperature is-and 10-20 ℃.
The add-on of chloroform is that every gram Lignanoids compounds adds 3-10mL.
The described time of leaving standstill is 12-48h after the heating for dissolving, dwell temperature is-and 20-5 ℃.
The method of from til, separating the Lignanoids compounds obtain not conforming to the fats composition is the combination of one or more methods in solvent low-temperature sludge method, saponification method, column chromatography, the distillation under vacuum.
Described til is the Residual oil that thick oil of non-roasting roasted sesame or roasting roasted sesame are oily or from grouts, extract.
The method of purifying sesamin of the present invention and sesamolin; At first be from til, to isolate the Lignanoids compounds that does not conform to the fats composition, adopt the method for specific solvent crystallization from Lignanoids compounds, to be purified into highly purified sesamin and sesamolin again.Sesamin solid of separating out and sesamolin solid are respectively through ethyl alcohol recrystallization, and purity can reach more than 95%.
Concrete, after obtaining staple and being the lignanoids mixture of sesamin and sesamolin,, leave standstill for some time the sesamin in the mixture is separated out earlier with adding a certain amount of ether in the mixture, filtration, filter cake is a sesamin for the white powder solid; Again with the minimum of chloroform dissolving, till adding then that sherwood oil to adularescent is muddy and occurring, a little after the heat of solution, leaving standstill after for some time was that adularescent sesamolin solid is separated out after filtrate decompression was steamed and to be desolventized.
The present invention is in the process of purifying sesamolin, and is higher relatively and sesamin is insoluble to ether and sesamolin is slightly soluble in this characteristic of ether according to sesamin content in this mixture, isolates most sesamin earlier with ether solvent method crystallization; After isolating most of sesamin, the staple in the mixture still is sesamin and sesamolin and other unsaponifiables, but the content of sesamin reduces the content increase of sesamolin greatly.Therefore adopt the mixed solvent crystallization of chloroform and sherwood oil that sesamolin is separated out; With respect to habitually in the past the general technology stability that adopts of refining sesamolin is poor, treatment capacity is little, the operator is required height, chromatography that the filler cost is high; Advantage such as that this method has is simple to operate, safety economy, technology stability are strong; Special suitability for industrialized production; This method can also obtain highly purified sesamin product simultaneously, reaches the purpose of comprehensive utilization.
The present invention has following advantage with respect to prior art:
The purification process of sesamin of the present invention and sesamolin has advantages such as simple to operate, safety economy, technology stability are strong, and special suitability for industrialized is used, and this method can obtain highly purified sesamin and sesamolin simultaneously, reaches the purpose of comprehensive utilization; Sesamin of separating out and sesamolin can obtain purity through the ethyl alcohol recrystallization processing respectively and reach the product more than 95%.
(4) embodiment:
Below with specific embodiment technical scheme of the present invention is described, but protection scope of the present invention is not limited thereto:
Embodiment 1
Get the til 100g of petroleum ether extraction, add methyl alcohol 500mL, 90 ℃ of reflux extraction 20min are after waiting to be chilled to room temperature; Put-30 ℃ of freezing 8h down, triglyceride level solidifies, at-20 ℃ of following suction filtrations; Get the extraction liquid of the mixture of Lignanoids compounds, decompression removes methyl alcohol, gets light yellow paste.
In this paste, add the 20mL mass concentration and be the ethanolic soln of 5% Pottasium Hydroxide; 90 ℃ of saponification 10min; Add water 100mL after the cooling and be transferred in the 500mL separating funnel and use extracted with diethyl ether, again through washing, anhydrous sodium sulfate drying, suction filtration and decompression remove solvent operate light yellow semi-solid paste.
In light yellow semi-solid paste, add the 20mL ether; Fully be sealed in 5 ℃ of condition held 6h after the vibration; Separate out white powder sesamin solid; Suction filtration must be filtrated and the white powder solid, and this solid is separated out white, needle-shaped crystals with the 8mL ethyl alcohol recrystallization, gets purity through separation, washing and vacuum-drying and reaches the sesamin 0.41g more than 95%.Behind the filtrate steaming removal solvent; Add the heat of solution a little of 3mL chloroform, add sherwood oil then, after heat makes muddy the disappearance a little until the muddy appearance of adularescent; 0 ℃ leaves standstill 12h; Separate out white solid, this white solid is separated out white feather shape crystal through the 5mL ethyl alcohol recrystallization, gets purity through separation, washing and vacuum-drying and reaches the sesamolin 0.24g more than 95%.
Embodiment 2
Get commercially available roasting roasted sesame oil 200mL; Join alumina column (40cm * 4cm i.d.; Aluminum oxide 150g) in, and uses the sherwood oil wash-out, adopt the 2mL elutriant to add the concentrated hydrochloric acid reacting by heating 5min that 1mL contains 2% (wt%) sucrose and monitor; To reaction when blush occurring eluent be replaced by ETHYLE ACETATE and carry out wash-out, till color reaction not occurring.Eluent ethyl acetate liquid gets yellow half and consolidates the shape lotion after removing solvent under reduced pressure.
This lotion successively carries out crystallization and recrystallization with ether, chloroform, sherwood oil and ethanol etc. to be handled, and obtains sesamin and sesamolin that purity reaches more than 95% and is respectively 0.68g and 0.33g.Used ether is 25mL, and chloroform is 4mL, and sesamin and the used ethanol of sesamolin recrystallization are respectively 10mL and 6mL, and other are with embodiment 1.
Claims (4)
1. the method for purification of sesamin and sesamolin is characterized in that, from til, separates obtaining the not Lignanoids compounds of fatty constituents earlier, adds ether afterwards and separates out sesamin; Filter, the gained filtrate decompression concentrates the back and uses dissolved in chloroform, adds the muddy appearance of sherwood oil to adularescent then, leaves standstill after the heating for dissolving and separates out sesamolin; The consumption of said ether is that every gram Lignanoids compounds adds 5-15mL; The add-on of chloroform is that every gram Lignanoids compounds adds 3-10mL; From til, separate and obtain not that the method for the Lignanoids compounds of fatty constituents is the combination of one or more methods in solvent low-temperature sludge method, saponification method, column chromatography, the distillation under vacuum.
2. the method for purification of sesamin as claimed in claim 1 and sesamolin is characterized in that, adds ether and leaves standstill and separates out sesamin, and the described time of leaving standstill is 0.5-24h, dwell temperature is-and 10-20 ℃.
3. the method for purification of sesamin as claimed in claim 1 and sesamolin is characterized in that, the described time of leaving standstill is 12-48h, dwell temperature is-and 20-5 ℃.
4. like the method for purification of described sesamin of one of claim 1-3 and sesamolin, it is characterized in that described til is the Residual oil that non-roasting roasted sesame is slightly oily, bake roasted sesame oil or from grouts, extract.
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| CN2009100654601A CN101602768B (en) | 2009-07-17 | 2009-07-17 | Method for purifying sesamin and sesamolin |
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| CN2009100654601A CN101602768B (en) | 2009-07-17 | 2009-07-17 | Method for purifying sesamin and sesamolin |
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| CN101602768A CN101602768A (en) | 2009-12-16 |
| CN101602768B true CN101602768B (en) | 2012-05-30 |
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| US8642604B2 (en) | 2006-04-04 | 2014-02-04 | The Regents Of The University Of California | Substituted pyrazolo[3,2-d]pyrimidines as anti-cancer agents |
| US8697709B2 (en) | 2008-10-16 | 2014-04-15 | The Regents Of The University Of California | Fused ring heteroaryl kinase inhibitors |
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| US9493467B2 (en) | 2006-04-04 | 2016-11-15 | The Regents Of The University Of California | PI3 kinase antagonists |
| US8642604B2 (en) | 2006-04-04 | 2014-02-04 | The Regents Of The University Of California | Substituted pyrazolo[3,2-d]pyrimidines as anti-cancer agents |
| US9359349B2 (en) | 2007-10-04 | 2016-06-07 | Intellikine Llc | Substituted quinazolines as kinase inhibitors |
| US8993580B2 (en) | 2008-03-14 | 2015-03-31 | Intellikine Llc | Benzothiazole kinase inhibitors and methods of use |
| US8637542B2 (en) | 2008-03-14 | 2014-01-28 | Intellikine, Inc. | Kinase inhibitors and methods of use |
| US9096611B2 (en) | 2008-07-08 | 2015-08-04 | Intellikine Llc | Kinase inhibitors and methods of use |
| US8697709B2 (en) | 2008-10-16 | 2014-04-15 | The Regents Of The University Of California | Fused ring heteroaryl kinase inhibitors |
| US8476431B2 (en) | 2008-11-03 | 2013-07-02 | Itellikine LLC | Benzoxazole kinase inhibitors and methods of use |
| US8476282B2 (en) | 2008-11-03 | 2013-07-02 | Intellikine Llc | Benzoxazole kinase inhibitors and methods of use |
| US8980899B2 (en) | 2009-10-16 | 2015-03-17 | The Regents Of The University Of California | Methods of inhibiting Ire1 |
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