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
- purification
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- til
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- PEYUIKBAABKQKQ-AFHBHXEDSA-N (+)-sesamin Chemical compound C1=C2OCOC2=CC([C@H]2OC[C@H]3[C@@H]2CO[C@@H]3C2=CC=C3OCOC3=C2)=C1 PEYUIKBAABKQKQ-AFHBHXEDSA-N 0.000 title claims abstract description 46
- PEYUIKBAABKQKQ-UHFFFAOYSA-N epiasarinin Natural products C1=C2OCOC2=CC(C2OCC3C2COC3C2=CC=C3OCOC3=C2)=C1 PEYUIKBAABKQKQ-UHFFFAOYSA-N 0.000 title claims abstract description 46
- VRMHCMWQHAXTOR-CMOCDZPBSA-N sesamin Natural products C1=C2OCOC2=CC([C@@H]2OC[C@@]3(C)[C@H](C=4C=C5OCOC5=CC=4)OC[C@]32C)=C1 VRMHCMWQHAXTOR-CMOCDZPBSA-N 0.000 title claims abstract description 46
- ZZMNWJVJUKMZJY-AFHBHXEDSA-N Sesamolin Chemical compound C1=C2OCOC2=CC([C@H]2OC[C@H]3[C@@H]2CO[C@@H]3OC2=CC=C3OCOC3=C2)=C1 ZZMNWJVJUKMZJY-AFHBHXEDSA-N 0.000 title claims abstract description 39
- ZZMNWJVJUKMZJY-UHFFFAOYSA-N Sesamolin Natural products C1=C2OCOC2=CC(C2OCC3C2COC3OC2=CC=C3OCOC3=C2)=C1 ZZMNWJVJUKMZJY-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 36
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000000706 filtrate Substances 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 239000008159 sesame oil Substances 0.000 claims abstract description 4
- 235000011803 sesame oil Nutrition 0.000 claims abstract description 4
- 244000000231 Sesamum indicum Species 0.000 claims description 13
- 241000207961 Sesamum Species 0.000 claims description 11
- 235000003434 Sesamum indicum Nutrition 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000000746 purification Methods 0.000 claims description 11
- 239000003921 oil Substances 0.000 claims description 10
- 235000019198 oils Nutrition 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 7
- 230000006837 decompression Effects 0.000 claims description 5
- 238000004440 column chromatography Methods 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims description 3
- 238000007127 saponification reaction Methods 0.000 claims description 3
- 239000012141 concentrate Substances 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 239000010802 sludge Substances 0.000 claims description 2
- 229930013686 lignan Natural products 0.000 abstract description 3
- -1 lignan compounds Chemical class 0.000 abstract description 3
- 235000009408 lignans Nutrition 0.000 abstract description 3
- 238000001914 filtration Methods 0.000 abstract description 2
- 239000003208 petroleum Substances 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 11
- 238000005516 engineering process Methods 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- UIOFUWFRIANQPC-JKIFEVAISA-N Floxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl UIOFUWFRIANQPC-JKIFEVAISA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Natural products OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000003053 immunization Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 150000005692 lignans Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000029865 regulation of blood pressure Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
The invention relates to a method for purifying sesamin and sesamolin in sesame oil. Separating lignan compounds without fat components from sesame oil, and adding diethyl ether to precipitate sesamin; filtering, concentrating the filtrate under reduced pressure, dissolving with chloroform, adding petroleum ether until white turbidity appears, heating for dissolving, and standing to separate out sesamolin. The method for purifying sesamin and sesamolin has the advantages of simple operation, safety, economy, strong process stability and the like, is particularly suitable for industrial application, and can simultaneously obtain high-purity sesamin and sesamolin to 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.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009100654601A CN101602768B (en) | 2009-07-17 | 2009-07-17 | Method for purifying sesamin and sesamolin |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009100654601A CN101602768B (en) | 2009-07-17 | 2009-07-17 | Method for purifying sesamin and sesamolin |
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| Publication Number | Publication Date |
|---|---|
| CN101602768A CN101602768A (en) | 2009-12-16 |
| CN101602768B true CN101602768B (en) | 2012-05-30 |
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| CN2009100654601A Expired - Fee Related CN101602768B (en) | 2009-07-17 | 2009-07-17 | Method for purifying sesamin and sesamolin |
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