CN1594310A - Method for extracting sesamin from sesame oil root - Google Patents
Method for extracting sesamin from sesame oil root Download PDFInfo
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- CN1594310A CN1594310A CN 200410041185 CN200410041185A CN1594310A CN 1594310 A CN1594310 A CN 1594310A CN 200410041185 CN200410041185 CN 200410041185 CN 200410041185 A CN200410041185 A CN 200410041185A CN 1594310 A CN1594310 A CN 1594310A
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- sesamin
- sesame oil
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- ethanol
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Abstract
The invention discloses a method for extracting sesamin from sesame oil root which consists of, extracting reclaimed sesame oil with skellysolve B, using the reclaimed sesame oil as raw material, extracting sesamin crude product by methanol or ethanol,and crystallizing the sesamin crude product.
Description
Technical field
A kind of method of extracting sesamin from sesame oil residue relates to the extracting method of sesamin.
Background technology
Sesame (sesame) may be so far known to by human the most ancient oilseeds as food resource, also be the seasonings that uses the earliest, extensively plant in the developing country in Asia and Africa.China is maximum in the world sesame producing country, calendar year 2001 output reach 810,000 tons, be about 40% of Gross World Product.The chemical constitution of sesame is mainly lipid, protein, carbohydrate, mineral substance, VITAMIN etc.Sesame contains abundant grease and protein, has higher edibleness.The oil length of sesame is generally about 50%.Sesame oil contains 80% unsaturated fatty acids approximately, and oleic acid and linolic acid are main unsaturated fatty acidss; Saturated fatty acid mainly is made up of palmitinic acid and stearic acid, and content is lower than 20% of total fatty acids.Unsaponifiables in the sesame oil is mainly sterol, tocopherol, sesamin, sesamol, sesamolin, sesamin phenol etc.Unrefined sesame oil is exactly because it contains the fat-soluble phenol antioxidant of lignanoids sesamin, sesamolin, sesamol and sesamin phenol with the physiological active functions why other plant oil phase ratio has better stability and uniqueness.
The sesame purposes is very extensive, can be used for the batching that sweet goods already, also can be used as cooky, biscuit etc.; But topmost still as oil plant, be used to produce sesame oil.At present, the preparation method of sesame oil mainly contains three kinds: machine presses method, water for method, solvent extraction method.Because China human consumer likes the edible sesame oil of directly producing, therefore domestic bigger sesame oil factory (as day clear sesame oil factory, permanent) along sesame oil factory basically the employing machine press method.It is exactly sesame oil residue that machine press for extracting juice method has a main by product.Domestic sesame oil factory is to abandon or give farmers''s as fertilizer sources to the processing of sesame oil residue basically.
Sesamin belongs to Lignanoids compounds, two methylenedioxyphenyl base groups and central tetrahydrochysene Kang Ji furans nuclear phase company, and molecular formula is C
20H
18O
6, concrete structure is as follows.Its english system called after Sesamin (tetrahydro-1,4-bis (3,4-(methylenedioxy) pHenyl)-1H, 3H-furo (3,4-c) furan), Chinese named adopts the heterocycle called after 2 of no specific names according to regulation pure and the applied chemistry meeting, and 6-two (3,4-secondary p-methoxy-phenyl)-3,7-two oxa-dicyclos (3,3,0) octane.
Also have other lignanoids materials in the sesame, as sesamolin (sesamolin), sesamin phenol (sesaminol), sesamol (sesamol) and sesamolin phenol (sesamolinol), concrete structure is as follows:
Sesamin (sesamin) sesamol (sesamol)
Sesamolin (sesamolin) sesamin phenol (sesaminol)
Sesamolin phenol (sesamolinol)
Sesamin is generally sheet or powdery white solid, is generally white needle-like crystals through the sesamin of organic solvent crystallization treatment, and molecular weight is 354.36, fusing point 120-121 ℃, has opticity, [a]
D 20=-56 ° of (CHCL
3).Sesamin is a lipid-soluble substance, and water insoluble, bronsted lowry acids and bases bronsted lowry is dissolved in organic solvents such as methyl alcohol.
Sesamin (sesamin) is a kind of in lignanoid's (lignan also is lignan) compounds, has very strong physiologically active.Lignanoid and isoflavones all belong to phytoestrogen, studies show that in the sesame that lignanoids material such as sesamin has physiological active functionses such as reducing cholesterol, anti-oxidant, protection liver.
Sesamin is because its distinctive physicochemical property and physiological function, in agricultural, food service industry and pharmaceutical industries great prospect, highly purified sesamin be applied in gradually the health care and pharmaceutically, the price of highly purified sesamin is very expensive, this mainly is because sesamin presents stronger antioxygenation in vivo, has various physiological active functions.The healthcare product of sesamin has appearred on the Japanese market adding at present.
External at present preparation sesamin is a raw material with the deodorization thing of sesame oil basically, and the physiologically active of sesamin is carried out deep research.Domestic research to sesamin also just progressively launches, to sesamin should be used as preliminary study, but seldom have the investigator that the preparation technology aspect of sesamin is studied.
Summary of the invention
The purpose of this invention is to provide a kind of method of from sesame oil residue, extracting sesamin.The sesame oil residue total amount that China abandoned in 1 year is about the 3000-4000 ton, and these depleted oil foots not only make producer suffer a large amount of financial losses, and have caused certain pollution to surrounding enviroment.Sesame oil residue is carried out utilization of waste material, therefrom extract the physiologically active substance of high added value such as sesamin, not only can reduce the environmental pollution that discarded sesame oil residue causes, can also produce good economic benefit.
Technical scheme of the present invention: with sesame oil factory waste-sesame oil residue is raw material, from sesame oil residue, extract the sesame oil of recovery earlier with normal hexane, with this sesame oil that reclaims is raw material, slightly carry product with methyl alcohol or extraction using alcohol sesamin, with ethanol sesamin is slightly carried product again and carry out crystallization purifying, obtain the sesamin product.From sesame oil residue, extract the technology of the sesame oil of recovery with normal hexane: the sesame oil residue of measuring certain volume, the normal hexane that adds 4 times of volumes, stirred 2 hours down at 45 ℃, the mixed solution centrifugation, the supernatant liquor rotary evaporation obtains reclaiming sesame oil, throw out repeats to extract with normal hexane once more, and operational condition is the same, and the recovery sesame oil that extracted twice is obtained merges collection.To reclaim sesame oil is raw material, extract sesamin and slightly put forward the technology of product: adopt methyl alcohol or ethanol as extraction solvent, solid-liquid ratio: reclaim sesame oil: methyl alcohol or ethanol are 1: 2.5-3, extract 55-62 ℃ of temperature, stirred extraction time 2.5-3 hour, and extracted the 3-4 hour standing separation time of back.Sesamin is slightly put forward the technology that product carry out crystallization purifying: adopt wet method crystalline method, in solution, make with extra care sesamin with the decrease temperature crystalline method, select ethanol as purification solvent, solid-liquid ratio g/mL: sesamin is slightly carried product: ethanol is 1: 30-40, the nature decrease temperature crystalline slowly shakes 25 ℃ of growing the grain temperature, rearing crystal time 2-3 hour, get the sesamin product through four crystallizations with this understanding.
Beneficial effect of the present invention: adopt methyl alcohol or ethanol from sesame oil residue, to extract sesamin, set up rational production technique, determine the optimum extraction process condition; And rough sesamin product carried out purifying.By analysis, the massfraction of sesame oil is 68.9% in the sesame oil residue, and the solid quality mark is 31.0%, and the sesamin massfraction is 0.251%; The massfraction of sesamin is 0.365% in the recovery sesame oil that extracts from sesame oil residue, peroxide value 3.7meq/kg.The sesame oil residue total amount that China abandoned in 1 year is about the 3000-4000 ton, and these depleted oil foots not only make producer suffer a large amount of financial losses, and have caused certain pollution to surrounding enviroment.Sesame oil residue is carried out utilization of waste material, therefrom extract the physiologically active substance of high added value such as sesamin, not only can reduce the environmental pollution that discarded sesame oil residue causes, can also produce good economic benefit.Can drive the deep processing research of China's sesame, promote the plantation of China's characteristic oil crops-sesame, promote agricultural restructuring, increase peasant's income.
The content of sesamin in the high effective liquid chromatography for measuring sesame oil: adopt alumina chromatographic column that sesame oil is carried out pre-treatment, use the HPLC method qualitative, quantitative then to sesamin.Through check, average recovery is 95.6%, and variation coefficient CV is 1.19%, has therefore set up the method for sesamin content in a kind of accurate mensuration sesame oil.
Percentage composition=the 0.5C of sesamin * V * X/m in the sesame oil
In the formula: the concentration of sesamin in the C-pretreatment fluid
V-has the cumulative volume of the elutriant of big absorbancy
The multiple that dilutes during X-supernatant liquor constant volume
The m-quality of the pretreated oil of alumina column
Embodiment
Embodiment 1. reclaims sesame oil from sesame oil residue
Accurately take by weighing sesame oil residue and the weighing m of certain volume v
1, add 4 times normal hexane (V: V), stir down 2h at 45 ℃; The mixed solution centrifugation, the supernatant liquor rotary evaporation obtains sesame oil; Throw out extracts once more, at last the sesame oil that obtains for twice is collected in weighing m together
3, throw out oven dry back weighing m
2
The sesame oil residue density p
1=m
1/ v
Solid content ρ in the oil foot
2=m
2/ m
1
The content ρ of sesame oil in the oil foot
3=m
3/ m
1
Embodiment 2. extracts sesamin and slightly carries product from reclaim sesame oil
Measure 200mL (175.5g) sesame oil, press solid-liquid ratio and add methyl alcohol at 1: 3, stir 2.5h down at 60 ℃, static then separatory 3 hours is got upper strata liquid rotary evaporation and is boiled off methyl alcohol.Add an amount of oil fan, 45 ℃, airtight stirring 0.5h, the suction filtration rear filtrate is separated out precipitation naturally, filters, and drying is weighed.
Finally obtain throw out 0.795g
By the content of sesamin in hair extraction yield=sedimentary quality/oil,
200mL sesame oil contains 175.5 * 0.365%=0.641g
Hair extraction yield=0.795/0.641 * 100%=124%
To sesamin high-efficient liquid phase chromatogram technique analysis in the throw out, purity is 67.5%, contains 0.795 * 0.675=0.537g, therefore, and actual extracting rate=0.537/0.641=83.7%
Embodiment 3. extracts sesamin and slightly carries product from reclaim sesame oil
Measure 200mL (175.5g) sesame oil, press solid-liquid ratio and add ethanol at 1: 2.5, stir 3h down at 55 ℃, static then separatory 4 hours is got upper strata liquid rotary evaporation and is boiled off ethanol.Add an amount of oil fan, 45 ℃, airtight stirring 0.5h, the suction filtration rear filtrate is separated out precipitation naturally, filters, and drying is weighed.
Finally obtain throw out 0.718g
By the content of sesamin in hair extraction yield=sedimentary quality/oil,
200mL sesame oil contains 175.5 * 0.365%=0.641g
Hair extraction yield=0.718/0.641 * 100%=112%
To sesamin high-efficient liquid phase chromatogram technique analysis in the throw out, purity is 68.9%, contains 0.718 * 0.689=0.494g, therefore, and actual extracting rate=0.494/0.641=77.2%
4. pairs of sesamins of embodiment are slightly carried the product crystallization purifying
Adopt ethanol that sesamin is slightly carried product and carry out crystallization purifying.Sesamin is slightly carried product/ethanol solid-liquid ratio (g/mL)
Naturally cooling in 1: 40, air, manually shake stirring, 25 ℃ of growing the grain temperature, rearing crystal time 2h slowly.
Under above-mentioned crystallization condition, crystalline product purity is 78.1%, and yield is 57.6%.Through four crystallizations, the purity of the finished product is 91.2%.
5. pairs of sesamins of embodiment are slightly carried the product crystallization purifying
Adopt ethanol that sesamin is slightly carried product and carry out crystallization purifying.Sesamin is slightly carried product/ethanol solid-liquid ratio (g/mL)
Naturally cooling in 1: 30, air, manually shake stirring, 25 ℃ of growing the grain temperature, rearing crystal time 3h slowly.
Under above-mentioned crystallization condition, crystalline product purity is 75.4%, and yield is 68.1%.
Claims (4)
1. the extracting method of a sesamin, it is characterized in that with sesame oil factory waste-sesame oil residue be raw material, from sesame oil residue, extract the sesame oil of recovery earlier with normal hexane, with this sesame oil that reclaims is raw material, slightly carry product with methyl alcohol or extraction using alcohol sesamin, with ethanol sesamin is slightly carried product again and carry out crystallization purifying, obtain the sesamin product.
2. the extracting method of sesamin according to claim 1, wherein from sesame oil residue, extract the technology of the sesame oil of recovery with normal hexane: the sesame oil residue of measuring certain volume, the normal hexane that adds 4 times of volumes, stirred 2 hours down at 45 ℃, the mixed solution centrifugation, the supernatant liquor rotary evaporation obtains reclaiming sesame oil, and throw out repeats to extract with the same operation condition with normal hexane once more, and the recovery sesame oil that extracted twice is obtained merges collection.
3. the extracting method of sesamin according to claim 1, wherein be raw material to reclaim sesame oil, extract sesamin and slightly put forward the technology of product: adopt methyl alcohol or ethanol as extraction solvent, solid-liquid ratio: reclaim sesame oil: methyl alcohol or ethanol are 1: 2.5-3, extract 55-62 ℃ of temperature, stirred extraction time 2.5-3 hour, and extracted the 3-4 hour standing separation time of back.
4. the extracting method of sesamin according to claim 1, sesamin is wherein slightly put forward the technology that product carry out crystallization purifying: adopt wet method crystalline method, in solution, make with extra care sesamin with the decrease temperature crystalline method, select ethanol as purification solvent, solid-liquid ratio g/mL: sesamin is slightly carried product: ethanol is 1: 30-40, natural decrease temperature crystalline, slowly shake, 25 ℃ of growing the grain temperature rearing crystal time 2-3 hour, get the sesamin product through four crystallizations with this understanding.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410041185 CN1594310A (en) | 2004-07-01 | 2004-07-01 | Method for extracting sesamin from sesame oil root |
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|---|---|---|---|
| CN 200410041185 CN1594310A (en) | 2004-07-01 | 2004-07-01 | Method for extracting sesamin from sesame oil root |
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| CN1594310A true CN1594310A (en) | 2005-03-16 |
Family
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103788106A (en) * | 2014-02-17 | 2014-05-14 | 驻马店市王书礼芝麻制品有限公司 | Method for extracting sesamin by utilizing sesame oil residue |
| CN104447780A (en) * | 2014-11-05 | 2015-03-25 | 桂林三宝生物科技有限公司 | Method for extracting sesamin from sesamum indicum |
| CN104817566A (en) * | 2015-04-03 | 2015-08-05 | 安徽新桥工贸有限责任公司 | Sesamin separation extraction method |
| CN113480514A (en) * | 2021-08-16 | 2021-10-08 | 内蒙古泓兴生物科技有限公司 | Method for extracting sesamin |
-
2004
- 2004-07-01 CN CN 200410041185 patent/CN1594310A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103788106A (en) * | 2014-02-17 | 2014-05-14 | 驻马店市王书礼芝麻制品有限公司 | Method for extracting sesamin by utilizing sesame oil residue |
| CN104447780A (en) * | 2014-11-05 | 2015-03-25 | 桂林三宝生物科技有限公司 | Method for extracting sesamin from sesamum indicum |
| CN104447780B (en) * | 2014-11-05 | 2016-08-24 | 桂林三宝生物科技有限公司 | A kind of method extracting sesamin from sesame |
| CN104817566A (en) * | 2015-04-03 | 2015-08-05 | 安徽新桥工贸有限责任公司 | Sesamin separation extraction method |
| CN113480514A (en) * | 2021-08-16 | 2021-10-08 | 内蒙古泓兴生物科技有限公司 | Method for extracting sesamin |
| CN113480514B (en) * | 2021-08-16 | 2022-07-22 | 内蒙古泓兴生物科技有限公司 | Method for extracting sesamin |
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