CN101602768A - The method of purification of a kind of sesamin and sesamolin - Google Patents
The method of purification of a kind of sesamin and sesamolin Download PDFInfo
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- CN101602768A CN101602768A CNA2009100654601A CN200910065460A CN101602768A CN 101602768 A CN101602768 A CN 101602768A CN A2009100654601 A CNA2009100654601 A CN A2009100654601A CN 200910065460 A CN200910065460 A CN 200910065460A CN 101602768 A CN101602768 A CN 101602768A
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Abstract
The present invention relates to the sesamin in a kind of sesame oil and the method for purification of sesamolin.From sesame oil, separate obtaining the not Lignanoids compounds of fatty constituents earlier, add ether afterwards and separate out sesamin; Filter, the gained filtrate decompression concentrates the back with the chloroform dissolving, adds sherwood oil then and occurs to adularescent is muddy, leaves standstill after the heating for dissolving and separates out sesamolin.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.
Description
(1) technical field
The present invention relates to the sesamin in a kind of sesame oil and the method for purification of sesamolin.
(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-sesame oil 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 products and health products additive agent of enhancing body health.
Sesamolin also is to be present in one of main lignan component in sesame and the sesame oil, 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-sesame oil that bakes and handle without refinery practice, is one of important biological composition in the sesame.Studies show that sesamolin has cholesterol, enhancing body immunizing power, hypertension, antithrombotic, the alleviation atherosclerosis of eliminating in interior free yl, the reduction serum, and numerous effects such as the alcohol metabolism of promotion, reinforcement detoxicating activity, anti-liver poisoning, inhibition mammary cancer are arranged.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 sesame oil, 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 unsuitable for suitability for industrialized production and use, this has also limited the exploitation of sesamolin related products.
(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 complexity are unsuitable for industrial application.
The technical solution used in the present invention is as follows:
The method of purification of a kind of sesamin and sesamolin separates obtaining the not Lignanoids compounds of fatty constituents earlier from sesame oil, add ether afterwards and separate out sesamin; Filter, the gained filtrate decompression concentrates the back with the chloroform dissolving, adds sherwood oil then and occurs to adularescent is muddy, leaves standstill after the heating for dissolving and separates out sesamolin.
The consumption of described 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 separating the Lignanoids compounds obtain not conforming to the fats composition from sesame oil is the combination of one or more methods in solvent low-temperature sludge method, saponification method, column chromatography, the distillation under vacuum.
Described sesame oil is the Residual oil that thick oil of non-roasting roasted sesame or roasting roasted sesame are oily or extract from grouts.
The method of purifying sesamin of the present invention and sesamolin, at first be from sesame oil, 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 main component and being the lignanoids mixture of sesamin and sesamolin, will add a certain amount of ether in the mixture earlier, leave standstill for some time the sesamin in the mixture is separated out, filter, filter cake is a sesamin for the white powder solid; After filtrate decompression is steamed and to be desolventized again with the minimum of chloroform dissolving, add then sherwood oil to adularescent is muddy occur till, a little after the heat of solution, leaving standstill after for some time is that adularescent sesamolin solid is separated out.
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 main component 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 are handled through ethyl alcohol recrystallization respectively and can be obtained purity and reach 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 sesame oil 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% potassium 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 under 5 ℃ of conditions after the vibration and place 6h, separate out white powder sesamin solid, suction filtration gets filtrate and white powder solid, 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 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 until the muddy appearance of adularescent, after heat makes muddy the disappearance a little, 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 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 use the sherwood oil wash-out, adopting the 2mL elutriant to add the concentrated hydrochloric acid reacting by heating 5min that 1mL contains 2% (wt%) sucrose monitors, to reaction when blush occurring eluent be replaced by ethyl 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 (7)
1. the method for purification of sesamin and sesamolin is characterized in that, separates obtaining the not Lignanoids compounds of fatty constituents earlier from sesame oil, adds ether afterwards and separates out sesamin; Filter, the gained filtrate decompression concentrates the back with the chloroform dissolving, adds sherwood oil then and occurs to adularescent is muddy, leaves standstill after the heating for dissolving and separates out sesamolin.
2. the method for purification of sesamin as claimed in claim 1 and sesamolin is characterized in that, the consumption of described ether is that every gram Lignanoids compounds adds 5-15mL.
3. the method for purification of sesamin as claimed in claim 2 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 ℃.
4. the method for purification of sesamin as claimed in claim 1 and sesamolin is characterized in that, the add-on of chloroform is that every gram Lignanoids compounds adds 3-10mL.
5. 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 ℃.
6. as the method for purification of described sesamin of one of claim 1-5 and sesamolin, it is characterized in that, from sesame oil, separate obtaining 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.
7. the method for purification of sesamin as claimed in claim 6 and sesamolin is characterized in that, described sesame oil is the Residual oil that non-roasting roasted sesame is slightly oily, bake roasted sesame oil or extract from grouts.
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| CN2009100654601A CN101602768B (en) | 2009-07-17 | 2009-07-17 | Method for purifying sesamin and sesamolin |
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