CN101921186B - Method for extracting linoleic acid from safflower seed oil by silvered silica-gel column chromatography - Google Patents
Method for extracting linoleic acid from safflower seed oil by silvered silica-gel column chromatography Download PDFInfo
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- CN101921186B CN101921186B CN 201010252031 CN201010252031A CN101921186B CN 101921186 B CN101921186 B CN 101921186B CN 201010252031 CN201010252031 CN 201010252031 CN 201010252031 A CN201010252031 A CN 201010252031A CN 101921186 B CN101921186 B CN 101921186B
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- silica
- column chromatography
- silvered
- linoleic acid
- silica gel
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- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 title claims abstract description 25
- 239000003813 safflower oil Substances 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims abstract description 14
- 235000020778 linoleic acid Nutrition 0.000 title claims abstract description 13
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 title claims abstract description 13
- 238000010898 silica gel chromatography Methods 0.000 title claims abstract description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000000741 silica gel Substances 0.000 claims abstract description 17
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 17
- 229960001866 silicon dioxide Drugs 0.000 claims abstract description 17
- 239000003480 eluent Substances 0.000 claims abstract description 11
- 238000005303 weighing Methods 0.000 claims abstract description 6
- 230000008961 swelling Effects 0.000 claims abstract description 5
- -1 silver ions Chemical class 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- 229960004232 linoleic acid Drugs 0.000 claims description 21
- 241001311547 Patina Species 0.000 claims description 18
- 235000019485 Safflower oil Nutrition 0.000 claims description 9
- 235000005713 safflower oil Nutrition 0.000 claims description 9
- 238000004587 chromatography analysis Methods 0.000 claims description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000010828 elution Methods 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 238000010025 steaming Methods 0.000 claims description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
- 238000004321 preservation Methods 0.000 claims description 3
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 3
- 235000011152 sodium sulphate Nutrition 0.000 claims description 3
- 238000000967 suction filtration Methods 0.000 claims description 3
- 239000006228 supernatant Substances 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 230000004913 activation Effects 0.000 claims 1
- 238000001994 activation Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract description 5
- 230000005526 G1 to G0 transition Effects 0.000 abstract description 3
- 238000004440 column chromatography Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 238000004458 analytical method Methods 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 239000000284 extract Substances 0.000 abstract description 2
- 229910052709 silver Inorganic materials 0.000 abstract description 2
- 239000004332 silver Substances 0.000 abstract description 2
- 238000001179 sorption measurement Methods 0.000 abstract description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 abstract description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 abstract description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 238000002791 soaking Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 5
- 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 4
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 4
- 239000003814 drug Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000008157 edible vegetable oil Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 206010058314 Dysplasia Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 206010056474 Erythrosis Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 230000003053 immunization Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000004223 radioprotective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
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- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for extracting linoleic acid from safflower seed oil by silvered silica-gel column chromatography, comprising the following steps: taking the activated silvered silica-gel as a stationary phase, soaking by chloroform and then filling into a chromatographic column, swelling and precipitating for a certain time, then weighing the safflower seed oil to add into the chromatographic column, eluting with a preferable eluent, quantitatively collecting, removing the eluent, finally preparing the linoleic acid product. On the basis of the separation principle of column chromatography, namely different adsorption forces of the substances on the stationary phase, separating the substances, while preparing complex compound by silver ions in the silvered silica-gel chromatographic column and carbon-carbon double bond of unsaturated fatty acid so as to separate and extract linoleic acid; the linoleic acid extracted by the method is high in purity, and meets the demands of industries such as analysis, medical and health-care product, etc.
Description
Technical field
The invention belongs to the preparation field of polyunsaturated fatty acid, especially a kind of method of extracting linoleic acid from safflower seed oil by silvered silica-gel column chromatography.
Background technology
Safflower oil is the high-quality edible oil that extracts a kind of health from the safflower dry mature fruit, its major ingredient be needed by human but can not be in vivo synthetic unsaturated fatty acids---linolic acid voluntarily, it is dissolving cholesterol effectively, has reducing blood-fat, removes blood vessel settling and hypotensive effect; Studies show that, Linoleic Acid in Safflower Oil content is the highest in the known plants edible oil, and average content reaches about 78%.
Linolic acid is that human body must lipid acid, and different physiological roles is arranged, such as radioprotective, reducing cholesterol with prevent and treat the different physiological roles such as arteriosclerosis, enhancing development, enhancing body immunizing power and cosmetology.The precursor of the hormonal substance that important physiological activity is arranged in linolic acid or the metabolic process--prostaglandin(PG), if human body lacks the susceptibility that linolic acid can cause erythrosis and increase dehydration and infect, infant's linolic acid shortage can cause dysplasia, therefore, highly purified linolic acid has a wide range of applications in industries such as medicine, food.
At present, the enriching and purifying polyunsaturated fatty acid generally adopts the methods such as low temperature crystallization, fractionation by adsorption, urea clathration, supercritical extraction, lipase-catalyzed hydrolysis, the common problem that above method separation and purification polyunsaturated fatty acid exists is the related products that is difficult to obtain higher degree, is difficult to satisfy the needs to industries such as the higher medicine of polyunsaturated fatty acid purity requirement, healthcare products.
Summary of the invention
The object of the invention is to overcome the deficiencies in the prior art, provide that a kind of product purity is high, the method for the simple extracting linoleic acid from safflower seed oil by silvered silica-gel column chromatography of extraction process.
The present invention realizes that the technical scheme of purpose is as follows:
A kind of method of extracting linoleic acid from safflower seed oil by silvered silica-gel column chromatography, step is as follows:
(1) preparation of patina silica gel: under the lucifuge condition, silica gel is joined in the silver nitrate aqueous solution that contains 5%-15%, heat 25-35min under in boiling water bath, stirring, then the cooling, suction filtration, in vacuum drying oven, activate 15-25h, make patina silica gel, place shady place for subsequent use;
(2) dress post: patina silica gel is placed chloroform, stir, get rid of bubble, leave standstill 1-1.5h, make its abundant swelling, be placed in the chromatography column with the tinfoil parcel, for subsequent use, obtain patina silicon chromatography column;
(3) wash-out: take by weighing safflower oil, be added drop-wise in the patina silicon chromatography column with dropper, use ethyl acetate/chloroform to carry out gradient elution as eluent, wherein each gradient eluent is 30-50mL, part 2 wash-outs, and flow velocity is 1-2mL/min;
(4) collect: every 30-50mL collects once, revolves steaming, removes eluent, uses n-hexane dissolution, adds saturated NaCl solution removal Ag
+, in organic phase, add anhydrous sodium sulphate, centrifugal 10min, supernatant liquor places brown bottle, and-20 ℃ of preservations are linolic acid.
And described ethyl acetate and chloroform gradient concentration are: 0,1%, 2%, 3%, be the volumetric concentration of ethyl acetate in chloroform.
And described linoleic purity is: 99.6%.
Advantage of the present invention and effect are:
1, the present invention is that the adsorptive power difference of material on stationary phase separated material according to the separation principle of column chromatography, utilize simultaneously silver ions in the patina silica gel column chromatography to form complex compound with the carbon-to-carbon double bond of unsaturated fatty acids and come the separation and Extraction linolic acid, the linolic acid purity that present method is extracted is higher, satisfies the needs of the industries such as analysis, medicine, healthcare products.
2, the present invention will have pharmaceutical use safflower oil as main raw material, main effect wherein and the linolic acid that is difficult to separate are extracted separately, improved the pharmaceutical use of safflower oil.
3, the present invention adopts the gradient elution method of ethyl acetate and chloroformic solution in the column chromatography for separation process, has effectively improved linoleic eluting rate, makes the extraction of safflower oil more abundant.
Embodiment
The present invention is further described below in conjunction with specific embodiments, and its specific embodiments only is construed as illustrating, and is not determinate, can not illustrate to limit protection scope of the present invention with following.
Inventive concept is: the patina silica gel of preparation 10%, dress post; A certain amount of safflower oil is encased in the patina silica gel column chromatography that makes, adopts preferred eluent to carry out gradient elution, collect successively elutriant according to doses, through vapor detection, collect the corresponding section elutriant, revolve steaming, obtain the linolic acid finished product that needs.
Specific embodiment
A kind of method of extracting linoleic acid from safflower seed oil by silvered silica-gel column chromatography, step is as follows:
1, the preparation of patina silica gel: under the lucifuge condition, take by weighing 6-10g silica gel, join and contain in 10% the silver nitrate aqueous solution, heat 30min under stirring in boiling water bath, then cooling, suction filtration activate 20h in vacuum drying oven, the patina silica gel of system places shady place for subsequent use;
2, dress post: take by weighing 6g patina silica gel, add the 20mL chloroform, stir, get rid of bubble, leave standstill 1h, make its abundant swelling, put in advance absorbent cotton in the chromatography column bottom, add the 20mL chloroform, with the slow impouring of patina silica gel of swelling, post external application tinfoil parcel uses behind the deposition 2h;
3, wash-out: unnecessary chloroform in the chromatography column is discharged at the bottom of post, until apart from patina silica gel face 0.5cm, take by weighing the 0.2g safflower oil, be added drop-wise in the chromatography column with dropper, use 0,1%, 2%, 3% ethyl acetate-the chloroform solvent system is as the eluent wash-out, 0,1%, 2%, 3% is the volumetric concentration of ethyl acetate in chloroform, wherein each concentration elutriant is 40mL, wash-out at twice, flow velocity is 1-2mL/min.
4, collect: every 40mL collects a pipe, revolves steaming, removes eluent, use the 2mL n-hexane dissolution, add saturated NaCl solution removal Ag+, in organic phase, add a certain amount of anhydrous sodium sulphate, dehydration, 6000r/min, centrifugal 10min, supernatant liquor places brown bottle,-20 ℃ of preservations, form with gas chromatographic detection lipid acid, calculate linolic acid purity and yield, be respectively 99.6% and 47%.
Claims (2)
1. the method for an extracting linoleic acid from safflower seed oil by silvered silica-gel column chromatography, it is characterized in that: step is as follows:
⑴ the preparation of patina silica gel: under the lucifuge condition, silica gel is joined in the silver nitrate aqueous solution that contains 5%-15%, heat 25-35min under in boiling water bath, stirring, then the cooling, suction filtration, activation 15-25 h makes patina silica gel in vacuum drying oven, places shady place for subsequent use;
⑵ fill post: patina silica gel is placed chloroform, stir, get rid of bubble, leave standstill 1-1.5h, make its abundant swelling, be placed in the chromatography column with the tinfoil parcel, and for subsequent use, obtain the patina silica gel column chromatography;
⑶ wash-out: take by weighing safflower oil, be added drop-wise in the patina silica gel column chromatography with dropper, use ethyl acetate/chloroform to carry out gradient elution as eluent, wherein each gradient eluent is 30-50mL, minute 2 wash-outs, and flow velocity is 1-2 mL/min;
⑷ collect: every 30-50mL collects once, revolves steaming, removes eluent, uses n-hexane dissolution, adds saturated NaCl solution removal Ag
+, in organic phase, add anhydrous sodium sulphate, centrifugal 10 min, supernatant liquor places brown bottle, and-20 ℃ of preservations are linolic acid;
Described ethyl acetate and chloroform gradient concentration are: 0,1%, 2%, 3%, be the volumetric concentration of ethyl acetate in chloroform.
2. the method for extracting linoleic acid from safflower seed oil by silvered silica-gel column chromatography according to claim 1, it is characterized in that: described linoleic purity is: 99.6%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010252031 CN101921186B (en) | 2010-08-12 | 2010-08-12 | Method for extracting linoleic acid from safflower seed oil by silvered silica-gel column chromatography |
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| Application Number | Priority Date | Filing Date | Title |
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| CN 201010252031 CN101921186B (en) | 2010-08-12 | 2010-08-12 | Method for extracting linoleic acid from safflower seed oil by silvered silica-gel column chromatography |
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| CN101921186A CN101921186A (en) | 2010-12-22 |
| CN101921186B true CN101921186B (en) | 2013-01-09 |
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| CN 201010252031 Expired - Fee Related CN101921186B (en) | 2010-08-12 | 2010-08-12 | Method for extracting linoleic acid from safflower seed oil by silvered silica-gel column chromatography |
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105481682A (en) | 2014-09-19 | 2016-04-13 | 浙江医药股份有限公司新昌制药厂 | Method for preparing high-content conjugated linoleic acid using vegetable oil as raw material by means of purification |
| RU2572788C1 (en) * | 2015-02-17 | 2016-01-20 | Федеральное государственное бюджетное учреждение "Российский кардиологический научно-производственный комплекс" Министерства здравоохранения Российской Федерации (ФГБУ "РКНПК" Минздрава России) | Method for obtaining linoleic acid |
| CN108593793B (en) * | 2018-04-19 | 2021-03-23 | 安徽德信佳生物医药有限公司 | Method for separating and purifying scopolamine by adopting coordination column chromatography |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100068292A1 (en) * | 2006-02-06 | 2010-03-18 | Sears Barry D | Novel Inhibitors of Arachidonic Acid Formation |
| CN101744237A (en) * | 2008-12-15 | 2010-06-23 | 天津科技大学 | Method for extracting and separating safflower seed oil |
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2010
- 2010-08-12 CN CN 201010252031 patent/CN101921186B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100068292A1 (en) * | 2006-02-06 | 2010-03-18 | Sears Barry D | Novel Inhibitors of Arachidonic Acid Formation |
| CN101744237A (en) * | 2008-12-15 | 2010-06-23 | 天津科技大学 | Method for extracting and separating safflower seed oil |
Non-Patent Citations (2)
| Title |
|---|
| 张汆等.硝酸银-硅胶纯化α-亚麻酸的研究.《离子交换与吸附》.2005,第21卷(第1期),47-54. |
| 硝酸银-硅胶纯化α-亚麻酸的研究;张汆等;《离子交换与吸附》;20050220;第21卷(第1期);47-54 * |
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