CN102633853B - Method for purifying campesterol from mixed plant sterol - Google Patents
Method for purifying campesterol from mixed plant sterol Download PDFInfo
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- CN102633853B CN102633853B CN201210105622.1A CN201210105622A CN102633853B CN 102633853 B CN102633853 B CN 102633853B CN 201210105622 A CN201210105622 A CN 201210105622A CN 102633853 B CN102633853 B CN 102633853B
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- campesterol
- plant sterol
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- sterol
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- SGNBVLSWZMBQTH-FGAXOLDCSA-N Campesterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 SGNBVLSWZMBQTH-FGAXOLDCSA-N 0.000 title claims abstract description 52
- BTEISVKTSQLKST-UHFFFAOYSA-N Haliclonasterol Natural products CC(C=CC(C)C(C)(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C BTEISVKTSQLKST-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 235000000431 campesterol Nutrition 0.000 title claims abstract description 52
- SGNBVLSWZMBQTH-PODYLUTMSA-N campesterol 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)CC[C@@H](C)C(C)C)[C@@]1(C)CC2 SGNBVLSWZMBQTH-PODYLUTMSA-N 0.000 title claims abstract description 52
- 238000000034 method Methods 0.000 title claims abstract description 28
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OILXMJHPFNGGTO-NRHJOKMGSA-N Brassicasterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@](C)([C@H]([C@@H](/C=C/[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 OILXMJHPFNGGTO-NRHJOKMGSA-N 0.000 description 2
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- 235000004420 brassicasterol Nutrition 0.000 description 2
- OILXMJHPFNGGTO-ZAUYPBDWSA-N brassicasterol 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)/C=C/[C@H](C)C(C)C)[C@@]1(C)CC2 OILXMJHPFNGGTO-ZAUYPBDWSA-N 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
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- OSELKOCHBMDKEJ-UHFFFAOYSA-N (10R)-3c-Hydroxy-10r.13c-dimethyl-17c-((R)-1-methyl-4-isopropyl-hexen-(4c)-yl)-(8cH.9tH.14tH)-Delta5-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(=CC)C(C)C)C1(C)CC2 OSELKOCHBMDKEJ-UHFFFAOYSA-N 0.000 description 1
- CSVWWLUMXNHWSU-UHFFFAOYSA-N (22E)-(24xi)-24-ethyl-5alpha-cholest-22-en-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 CSVWWLUMXNHWSU-UHFFFAOYSA-N 0.000 description 1
- MCWVPSBQQXUCTB-UHFFFAOYSA-N (24Z)-5alpha-Stigmasta-7,24(28)-dien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(=CC)C(C)C)CCC33)C)C3=CCC21 MCWVPSBQQXUCTB-UHFFFAOYSA-N 0.000 description 1
- KLEXDBGYSOIREE-UHFFFAOYSA-N 24xi-n-propylcholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CCC)C(C)C)C1(C)CC2 KLEXDBGYSOIREE-UHFFFAOYSA-N 0.000 description 1
- LPZCCMIISIBREI-MTFRKTCUSA-N Citrostadienol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C LPZCCMIISIBREI-MTFRKTCUSA-N 0.000 description 1
- ARVGMISWLZPBCH-UHFFFAOYSA-N Dehydro-beta-sitosterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(CC)C(C)C)CCC33)C)C3=CC=C21 ARVGMISWLZPBCH-UHFFFAOYSA-N 0.000 description 1
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- Steroid Compounds (AREA)
Abstract
The invention discloses a method for purifying campesterol from mixed plant sterol. According to the method disclosed by the invention, different plant sterol components have different solubilities and different degrees of crystallinity in a specific organic solvent, acetone is taken as an organic solvent to perform recrystallization on a plant sterol mixture for multiple times, the contents of all plant sterol monomers are respectively detected by chromatography, the purity of the campesterol in all-level crystals can be determined, and the campesterol with higher purity can be finally extracted. The invention provides the method for purifying the sterol monomers from the mixed plant sterol by only using one organic solvent under large-scale production conditions. The method disclosed by the invention has important theoretical and practical significance in the aspect of extraction of natural and pure products including the plant sterol, can play an important role in fine chemistry industry and analytical chemistry of plants, and has broad application prospects.
Description
Technical field
The present invention relates to biochemical industry or field of fine chemical, be specifically related to a kind of method of campesterol of purifying from mixed phytosterin.
Background technology
Mixed phytosterin is that a class formation is similar, the steroidal compounds that physical properties difference is little, be mainly derived from tall oil and vegetable oil refining deodorization distillate, its main component has β-sitosterol (β-sitosterol), campesterol (campesterol), Stigmasterol (stigmasterol) and brassicasterol (avenasterol) etc.
Plant sterol has very important physiological function, can effectively reduce low density cholesterol, reduce cardiopathic incidence, the effect such as anticancer and anti-inflammatory.The different physiological roles of plant sterol makes it be used widely at multiple fields such as medicine, makeup, growth of animal agent, food, weaving, printing and sheet processing industry.The product commercialization of plant sterol, plant sterol ester and derivative thereof.The high efficiency of plant sterol and security make plant sterol related products have very vast potential for future development.
Due to the further application of plant sterol on medicine industry and scientific research in recent years, requirements at the higher level are proposed to its purity.How mixed phytosterin being separated into single sterol product, and improving its yield and purity, is the study hotspot of current plant sterol separation and purification.Separation and purification is carried out to mixed phytosterin, comparatively cheap raw material can be provided for the production of steroid drugs.Effective separation of mixed phytosterin realizes an important subject in single component high-purity vegetable sterol monomer large-scale production process.Because structural extreme is similar, separation and purification β-sitosterol, campesterol and brassicasterol from mixed phytosterin, obtaining the higher each sterol monomer of purity is a more difficult and loaded down with trivial details job.Up to the present, the method extracting sterol has solvent crystallization, complexometry, molecular distillation method, absorption method, chromatography etc., selecting of various method is requirement according to raw material variety, composition, separating difficulty and product purity, also will consider industrial reliability and economy.Comprehensive above factor, adopts solvent crystallization for mixing sterol monomer separation study general.The indivedual sterol of direct utilization in a solvent dissolubility difference carries out multistage fractional crystallization, though crystallisation times is more, technique is simple, easy to operate, and purity also can be higher.
At present, the research both at home and abroad for the separation and purification of β-sitosterol and Stigmasterol is many, and it is also higher to obtain corresponding monomer purity, can meet the research to its relevant physiological activity and market application.And the research of the campesterol enriched equally for content is little, separation and purification technology about campesterol more rarely has report, and the campesterol monomer purity of selling in the market can only reach 60%, and expensive, can not meet the research of its relevant physiological activity far away and commercially produce requirement.
Summary of the invention
The object of the invention is to overcome in existing separating-purifying sterol monomer process, be difficult to realize the difficulty that campesterol is separated completely with Sitosterol, providing one can, under mass production conditions, only utilize a kind of organic solvent from mixed phytosterin, extract the method for high purity campesterol.
The present invention adopts technique simple, easy-operating solvent crystallization separation and purification campesterol, its principle is, different plant sterol constituent temperature variant different solubility in specific organic solvent, adopts the suitable organic solvent of boiling point can carry out multistage fractional crystallization separation to the campesterol in mixed phytosterin.
The technical solution adopted for the present invention to solve the technical problems is as follows:
From mixed phytosterin, be separated the method preparing campesterol, carry out according to following step:
1. mixed phytosterin is placed in organic solvent, high temperature bath is after sterol all dissolves, and water-bath is cooled to crystallization;
2. constant temperature growing the grain a few hours are kept;
3. decompress filter, collects filter cake and filtrate.Filter cake natural air drying, filtrate decompression removes solvent;
4. vapor-phase chromatography or high performance liquid chromatography is adopted to detect the content of campesterol monomer in filter cake and filtrate respectively;
5. carry out recrystallization next time according to identical material ratio, repeatedly repetitive operation step, direct product purity can reach 75%, and filtrate is through rotary evaporation and reclaim solid part; Difference according to campesterol content can carry out mixing again and carry out crystallization next time by same material ratio.
Described step 1. in the content of campesterol must not lower than 25% in mixed phytosterin; Organic solvent is acetone, and the quality of mixed phytosterin and solvent acetone and volume ratio are 1:5 ~ 25(grams per milliliter).
Described step 1. middle water-bath solvent temperature is 50 ~ 70 DEG C, after sterol mixture fully dissolves, is cooled to 10 ~ 25 DEG C.
Described step is 2. middle keeps constant temperature growing the grain 12-24 hour.
Described step 3. in filtrate reduce pressure in 40 ~ 60 DEG C of water-baths rotary evaporation remove solvent, reclaim solid matter.
Described step 4. middle vapor-phase chromatography adopts gas chromatographic column to be PHENYL-METHYL stationary phase chromatographic column, adopts temperature-programmed mode to detect.
Described step 4. in liquid-phase chromatographic column in high performance liquid chromatography, be analysis mode C18 or C8 performance liquid chromatographic column, moving phase is one or both the combination in acetonitrile, Virahol, first alcohol and water.
Described step 5. repeatedly repetitive operation step is that the filter cake of last time is carried out recrystallization next time again according to same technique, and repeat 2 ~ 10 times, can obtain the campesterol of white powder after recycling design, purity reaches more than 80%.
Described step 5. repeatedly repetitive operation step or the plant sterol reclaimed from filtrate is carried out mixing according to the content of campesterol and carries out recrystallization next time again according to same technique, repeat 2 ~ 10 times, can determine the number of times of recrystallization according to the requirement of oil recovery sterol content, the yield of last campesterol is more than 75%.
Beneficial effect of the present invention is:
1, adopt mixed phytosterin to be raw material, only adopt a kind of organic solvent just can obtain highly purified campesterol, have with low cost compared with additive method, the advantages such as technique is simple, easy and simple to handle.
2, adopt high performance liquid chromatography to monitor in real time each recrystallization reaction process, make to be obtained by reacting accurate control, ensure that the purity of product and improve yield, make yield bring up to more than 75%, for suitability for industrialized production campesterol provides condition.
Embodiment
Below in conjunction with embodiment, the invention will be further described.
embodiment 1:
1. take 20 grams of plant sterol (purity 97%, wherein campesterol content is 32.9%), with plant sterol and reagent quality volume ratio for 1:20 adds 400 milliliters of analytical pure acetone in Erlenmeyer flask, be placed in 50 DEG C of water-baths to dissolve, after plant sterol all dissolves, water-bath is cooled to 15 DEG C, and adularescent crystal is slowly separated out.
2. be statically placed on platform, keep constant temperature 12 hours.
3. be incubated decompress filter, collect filter cake and filtrate, filter cake natural air drying, the filtrate rotary evaporation that reduces pressure in 40 DEG C of water-baths reclaims sterol, removes organic solvent.The content of campesterol in adopt gas chromatograph to detect respectively sterol that filter cake and filtrate reclaims, gas chromatographic column is PHENYL-METHYL stationary phase chromatographic column, nitrogen as carrier gas, temperature-programmed mode to 320 DEG C.
4. filter cake carries out recrystallization next time by identical material ratio, successively method recrystallization 8 times, can obtain the campesterol that purity is 80%.Filtrate is underpressure distillation process in 50 DEG C of water-baths, reclaim steroid alcohol and solvent, the plant sterol of recovery carries out recrystallization according to identical material ratio, and the plant sterol crystallization of recovery can obtain the campesterol that purity is 78% for 9 times, the total recovery of last campesterol is 76.3%, and solvent recovering rate is 93%.
embodiment 2:
1. take 10 grams of plant sterol (purity 97%, campesterol content is 32.9%), with plant sterol and reagent quality volume ratio for 1:10 adds 100 milliliters of analytical pure acetone in Erlenmeyer flask, be placed in 55 DEG C of water-baths to dissolve, after plant sterol all dissolves, water-bath is cooled to 10 DEG C, and adularescent crystal is slowly separated out.
2. be statically placed on platform, keep constant temperature 18 hours.
3. be incubated decompress filter, collect filter cake and filtrate.Filter cake natural air drying, filtrate reduce pressure in 50 DEG C of water-baths rotary evaporation reclaim sterol, remove organic solvent.Adopt high performance liquid chromatograph to detect the content of campesterol in the sterol of filter cake and filtrate recovery respectively, the chromatographic column type of employing is analysis mode ODS C18 post, and moving phase is acetonitrile/methanol=6:4, flow velocity 1 mL/min, ultraviolet detection wavelength 206 nm.
4. filter cake carries out recrystallization next time by identical material ratio, successively method recrystallization 9 times, can obtain the campesterol that purity is 81.8%.Filtrate is underpressure distillation process in 40 DEG C of water-baths, reclaim steroid alcohol and solvent, the plant sterol of recovery carries out recrystallization according to identical material ratio, and the plant sterol crystallization of recovery can obtain the campesterol that purity is 79.5% for 9 times, the total recovery of last campesterol is 75.3%, and solvent recovering rate is 95%.
embodiment 3:
1. take 5 grams of plant sterol (purity 97%, campesterol content is 32.9%), with plant sterol and reagent quality volume ratio for 1:15 adds 75 milliliters of analytical pure acetone in Erlenmeyer flask, be placed in 60 DEG C of water-baths to dissolve, after plant sterol all dissolves, water-bath is cooled to 20 DEG C, and adularescent crystal is slowly separated out.
2. be statically placed on platform, keep constant temperature 24 hours.
3. be incubated decompress filter, collect filter cake and filtrate, filter cake natural air drying, the filtrate rotary evaporation that reduces pressure in 45 DEG C of water-baths reclaims sterol, removes organic solvent.Adopt high performance liquid chromatograph to detect the content of campesterol in the sterol of filter cake and filtrate recovery respectively, the chromatographic column type of employing is analysis mode C8 post, and moving phase is acetonitrile/isopropanol/water=90:7:3, flow velocity 1 mL/min, ultraviolet detection wavelength 208 nm.
4. filter cake carries out recrystallization next time by identical material ratio, successively method recrystallization 8 times, can obtain the campesterol that purity is 81.5%.Filtrate is underpressure distillation process in 55 DEG C of water-baths, reclaim steroid alcohol and solvent, the plant sterol of recovery carries out recrystallization according to identical material ratio, and the plant sterol crystallization of recovery can obtain the campesterol that purity is 79.6% for 9 times, the total recovery of last campesterol is 75.8%, and solvent recovering rate is 95%.
embodiment 4
1. take 15 grams of plant sterol (purity 97%, campesterol content is 32.9%), with plant sterol and reagent quality volume ratio for 1:10 adds 150 milliliters of analytical pure acetone in Erlenmeyer flask, be placed in 70 DEG C of water-baths to dissolve, after plant sterol all dissolves, water-bath is cooled to 20 DEG C, and adularescent crystal is slowly separated out.
2. be statically placed on platform, keep constant temperature 18 hours.
3. be incubated decompress filter, collect filter cake and filtrate, filter cake natural air drying, the filtrate rotary evaporation that reduces pressure in 45 DEG C of water-baths reclaims sterol, removes organic solvent.Adopt high performance liquid chromatograph to detect the content of campesterol in the sterol of filter cake and filtrate recovery respectively, the chromatographic column type of employing is analysis mode C8 post, and moving phase is acetonitrile/methanol/water=6:3:1, flow velocity 1.5 mL/min, ultraviolet detection wavelength 208 nm.
4. filter cake carries out recrystallization next time by identical material ratio, successively method recrystallization 10 times, can obtain the campesterol that purity is 82.3%.Filtrate is underpressure distillation process in 50 DEG C of water-baths, reclaim steroid alcohol and solvent, the plant sterol of recovery carries out recrystallization according to identical material ratio, and the plant sterol crystallization of recovery can obtain the campesterol that purity is 78.8% for 9 times, the total recovery of last campesterol is 76.8%, and solvent recovering rate is 95%.
Claims (1)
1. from mixed phytosterin, be separated the method preparing campesterol, it is characterized in that carrying out according to following step:
1. mixed phytosterin is placed in organic solvent, high temperature bath is after sterol all dissolves, and water-bath is cooled to crystallization;
2. constant temperature growing the grain a few hours are kept;
3. decompress filter, collects filter cake and filtrate; Filter cake natural air drying, filtrate decompression removes solvent;
4. vapor-phase chromatography or high performance liquid chromatography is adopted to detect the content of campesterol monomer in filter cake and filtrate respectively;
5. carry out recrystallization next time according to identical material ratio, repeatedly repetitive operation step, direct product purity can reach 75%;
Described step 1. in the content of campesterol must not lower than 25% in mixed phytosterin; Organic solvent is acetone, and the quality of mixed phytosterin and solvent acetone and volume ratio are 1:5 ~ 25 grams per milliliter;
Described step 1. middle water-bath solvent temperature is 50 ~ 70 DEG C, after sterol mixture all dissolves, is cooled to 10 ~ 25 DEG C;
Described step is 2. middle keeps constant temperature growing the grain 12-24 hour;
Described step 3. in filtrate reduce pressure in 40 ~ 60 DEG C of water-baths rotary evaporation remove solvent, reclaim solid matter;
Described step 4. middle vapor-phase chromatography adopts gas chromatographic column to be PHENYL-METHYL stationary phase chromatographic column, adopts temperature-programmed mode to detect;
Described step 4. in liquid-phase chromatographic column in high performance liquid chromatography, be analysis mode C18 or C8 performance liquid chromatographic column, moving phase is one or both the combination in acetonitrile, Virahol, first alcohol and water;
Described step 5. repeatedly repetitive operation step be by last step 3. in filter cake according to same technique, repeatedly carry out from step 1. to recrystallization 3., repeat 2 ~ 10 times, filter cake can obtain the campesterol of white powder after removing solvent acetone, purity reaches more than 80%;
Described step 5. repeatedly repetitive operation step, also comprise by step 3. in the solid part that reclaims after rotary evaporation of filtrate utilize step 4. to detect campesterol content after, mix according to campesterol content, and according to same technique, repeatedly carry out from step 1. to 3. recrystallization, repeat 2 ~ 10 times, also purification is carried out to the campesterol in filtrate; Total recovery is more than 75%.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1374319A (en) * | 2002-03-28 | 2002-10-16 | 武汉凯迪精细化工有限公司 | Method of extracting stigmasterol from mixed plant sterol |
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| CN1374319A (en) * | 2002-03-28 | 2002-10-16 | 武汉凯迪精细化工有限公司 | Method of extracting stigmasterol from mixed plant sterol |
Non-Patent Citations (3)
| Title |
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| 结晶法分离精制混合植物甾醇中β-谷甾醇和豆甾醇;许文林等;《过程工程学报》;20030228;第3卷(第1期);73-78 * |
| 重结晶法分离混合植物甾醇中豆甾醇;王雅琼等;《扬州大学学报(自然科学版)》;20050531;第5卷(第2期);53-56 * |
| 重结晶法精制植物甾醇的溶剂选择;许文林等;《扬州大学学报(自然科学版)》;20020228;第5卷(第1期);58-61、70 * |
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