CN107090357A - A kind of method of the extraction purification unrighted acid in Silybum Marianum Gaertn Seed Oil - Google Patents
A kind of method of the extraction purification unrighted acid in Silybum Marianum Gaertn Seed Oil Download PDFInfo
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- CN107090357A CN107090357A CN201710479047.4A CN201710479047A CN107090357A CN 107090357 A CN107090357 A CN 107090357A CN 201710479047 A CN201710479047 A CN 201710479047A CN 107090357 A CN107090357 A CN 107090357A
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- unrighted acid
- seed oil
- urea
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- silybum marianum
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- 239000002253 acid Substances 0.000 title claims abstract description 27
- 235000010841 Silybum marianum Nutrition 0.000 title claims abstract description 25
- 244000272459 Silybum marianum Species 0.000 title claims abstract description 23
- 235000015112 vegetable and seed oil Nutrition 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000000605 extraction Methods 0.000 title claims abstract description 13
- 238000000746 purification Methods 0.000 title claims abstract description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000004202 carbamide Substances 0.000 claims abstract description 20
- 239000003814 drug Substances 0.000 claims abstract description 6
- 239000008280 blood Substances 0.000 claims abstract description 5
- 210000004369 blood Anatomy 0.000 claims abstract description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 14
- 238000000967 suction filtration Methods 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 9
- 238000010992 reflux Methods 0.000 claims description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000003963 antioxidant agent Substances 0.000 claims description 6
- 230000003078 antioxidant effect Effects 0.000 claims description 6
- 235000006708 antioxidants Nutrition 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 230000006837 decompression Effects 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- 239000008236 heating water Substances 0.000 claims description 5
- 238000007789 sealing Methods 0.000 claims description 5
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 4
- 241000320380 Silybum Species 0.000 claims description 2
- 229930003427 Vitamin E Natural products 0.000 claims description 2
- 239000012065 filter cake Substances 0.000 claims description 2
- 230000008014 freezing Effects 0.000 claims description 2
- 238000007710 freezing Methods 0.000 claims description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 2
- 235000019165 vitamin E Nutrition 0.000 claims description 2
- 229940046009 vitamin E Drugs 0.000 claims description 2
- 239000011709 vitamin E Substances 0.000 claims description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 claims 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims 1
- 239000010496 thistle oil Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 14
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 14
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 14
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 14
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 14
- 239000005642 Oleic acid Substances 0.000 description 13
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 13
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 10
- 235000020778 linoleic acid Nutrition 0.000 description 10
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 10
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 description 6
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 description 6
- LNJCGNRKWOHFFV-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanenitrile Chemical compound OCCSCCC#N LNJCGNRKWOHFFV-UHFFFAOYSA-N 0.000 description 6
- PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 description 6
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 6
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 6
- 229940073769 methyl oleate Drugs 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000012086 standard solution Substances 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000012159 carrier gas Substances 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
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K31/201—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having one or two double bonds, e.g. oleic, linoleic acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
- C11B7/0008—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents
- C11B7/0016—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents in hydrocarbons or halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of method of the extraction purification unrighted acid in Silybum Marianum Gaertn Seed Oil, by using the unrighted acid of the method extraction purification Silybum Marianum Gaertn Seed Oil of urea clathrate, obtained unrighted acid purity is higher, the preparation available for blood lipid-lowering medicine.
Description
Technical field
The invention belongs to field of medicaments, and in particular to a kind of side of the extraction purification unrighted acid in Silybum Marianum Gaertn Seed Oil
Method.
Background technology
Silybum Marianum Gaertn Seed Oil be not only of high nutritive value it is edible, but also with higher medical value.Contain in Silybum Marianum Gaertn Seed Oil
There is abundant linoleic acid, with reduction cholesterol, prevent artery sclerosis etc. from acting on.It is sub- there is presently no being separated from Silybum Marianum Gaertn Seed Oil
The report of oleic acid.
The content of the invention
It is an object of the invention to provide a kind of side that the unrighted acids such as linoleic acid are isolated and purified in Silybum Marianum Gaertn Seed Oil
Method, for preparing Small side effects, can prevent or treat and alleviate the medicine of high fat of blood.
The present invention is achieved through the following technical solutions：
A kind of method of the extraction purification unrighted acid in Silybum Marianum Gaertn Seed Oil, comprises the following steps：
(1) urea is added into solvent, dissolve by heating, then cool, antioxidant added thereto, after add fine grinding
Ji oil, is then stirred at reflux and is cooled to room temperature, and inclusion crystallization under freezing conditions, obtains inclusion compound after sealing；
(2) inclusion compound, rapid suction filtration are taken out after certain time, filter cake is washed several times with ethanol, filtrate decompression concentration is waved
Go out more than half ethanol, use n-hexane extraction unrighted acid, n-hexane layer is washed with deionized to pH 5~6, added
Appropriate anhydrous sodium sulfate, dry 4~5h, suction filtration, it is to obtain refined unrighted acid that revolving, which removes n-hexane,.
Preferably, described solvent is 95% ethanol or 95% methanol, and the addition of urea adds for every milliliter of ethanol
The ratio of 0.8-1.2g urea, urea and Silybum Marianum Gaertn Seed Oil is 2: 1,3: Isosorbide-5-Nitrae: 1, it is preferable that the ratio of urea and Silybum Marianum Gaertn Seed Oil is 3
∶1.If the addition of urea is very few, saturated fatty acid inclusion is incomplete, if the ratio of urea is excessive, oleic acid and linoleic acid
Also will be by urea clathrate, therefore urea is excessive very few can all cause the reduction of oleic acid and linoleic acid purity.
The condition of heating for dissolving is 65-75 DEG C of heating water bath dissolving, is then cooled to 55-60 DEG C.
The antioxidant is BHT or vitamin E, and the addition of antioxidant is the 0.05% of solvent volume.
The addition of Silybum Marianum Gaertn Seed Oil is 1/3 (w/w) of urea.
The condition being stirred at reflux is to be stirred at reflux 30-35min at 55-65 DEG C.
The condition of inclusion crystallization is that inclusion crystallization is carried out in -15 DEG C of refrigerator.
(3) the refined unrighted acid obtained after including is using oleic acid, linoleic acid as Testing index, using gas chromatography
Its content is determined to determine the yield and purity of product.
GC conditions：The gas chromatographs of Agilent 7890；HP-Innowax capillary columns, hydrogen flameionization inspection
Survey device；Heating schedule：170 DEG C are initial temperature, with 10 DEG C of min-1210 DEG C are risen to, 1min is kept, then with 2 DEG C of min-1Rise
To 220 DEG C, 1min is kept, finally with 10 DEG C of min-1240 DEG C are risen to, 5min is maintained.260 DEG C of detector temperature, injection port temperature
250 DEG C of degree, split ratio is 30: 1, and sample size is 1 μ L, and carrier gas is nitrogen, and flow velocity is 1mLmin-1, H2Flow velocity is 30mL
min-1, air 300mLmin-1；
The configuration of standard solution：Precision weighs methyl oleate, methyl linoleate standard items and is placed in 10mL volumetric flasks in right amount
In, adding n-hexane dissolves it, and constant volume shakes up, and is configured to the concentration respectively 0.98mg of methyl oleate, methyl linoleate
mL-1、1.13mg·mL-1Standard solution；
Esterification process：Precision weighs the refined unrighted acid 500mg after inclusion, is placed in 50mL volumetric flasks, according to
Secondary addition ether: n-hexane (1: 1) 10mL mixed solvents, 10mL methanol, 0.5mol/LKOH/CH3OH solution 10mL, are placed
60min, adds water to 50mL, takes supernatant anhydrous sodium sulfate to remove trace water stand-by.Supernatant 1mL is taken in 10mL volumetric flasks
In, plus n-hexane is settled to scale, shakes up, it is to be measured.
Experimental result：Under above-mentioned chromatographic condition, methyl oleate, methyl linoleate standard items are measured, bid is obtained
Directrix curve；To do not include Silybum Marianum Gaertn Seed Oil, inclusion after refined thing be measured, oleic acid purity and Asia are gone out according to calculated by peak area
Oleic acid purity, and calculate the yield after inclusion；It is 25% to measure and do not include Silybum Marianum Gaertn Seed Oil mid-oleic, and linoleic acid content is
50%.
The present invention is proposed the unrighted acid prepared using the above method and prepared for preventing or controlling simultaneously
Application in the medicine for the treatment of or alleviation high fat of blood.
Beneficial effect：Compared with prior art, the present invention utilizes the method extraction purification milk thistle of urea clathrate for the first time
The unrighted acid of oil；Obtained unrighted acid purity is higher, the preparation available for blood lipid-lowering medicine.
Specific embodiment
The technical process of the present invention is further illustrated below by way of specific embodiment, but the present invention is not limited in this
A little examples.
Embodiment 1：
1g urea is dissolved in 4mL95% ethanol, then 70 DEG C of heating water bath dissolvings are cooled to 60 DEG C, by urine oil than being 2: 1
Refined Silybum Marianum Gaertn Seed Oil (BHT that volume fraction of ethanol is 0.05% is added before sample-adding) is added, is stirred at reflux at 60 DEG C
30min, is cooled to after room temperature, sealing and is placed on inclusion crystallization in -15 DEG C of refrigerator.Inclusion compound, rapid suction filtration (filter are taken out after 24h
Cake is washed 3 times with ethanol), filtrate decompression concentration shoots more than half ethanol, uses n-hexane extraction unrighted acid, n-hexane
Layer is washed with deionized to PH 5~6, the appropriate anhydrous sodium sulfate of addition, dry 5h, suction filtration, and it is to obtain that revolving, which removes n-hexane,
Refined unrighted acid.
The refined unrighted acid obtained after inclusion is surveyed using oleic acid, linoleic acid as Testing index using gas chromatography
Determine its content to determine the yield and purity of product.
GC conditions：The gas chromatographs of Agilent 7890；HP-Innowax capillary columns, hydrogen flameionization inspection
Survey device；Heating schedule：170 DEG C are initial temperature, with 10 DEG C of min-1210 DEG C are risen to, 1min is kept, then with 2 DEG C of min-1Rise
To 220 DEG C, 1min is kept, finally with 10 DEG C of min-1240 DEG C are risen to, 5min is maintained.260 DEG C of detector temperature, injection port temperature
250 DEG C of degree, split ratio is 30: 1, and sample size is 1 μ L, and carrier gas is nitrogen, and flow velocity is 1mLmin-1, H2Flow velocity is 30mL
min-1, air 300mLmin-1；
The configuration of standard solution：Precision weighs methyl oleate, methyl linoleate standard items and is placed in 10mL volumetric flasks in right amount
In, adding n-hexane dissolves it, and constant volume shakes up, and is configured to the concentration respectively 0.98mg of methyl oleate, methyl linoleate
mL-1、1.13mg·mL-1Standard solution；
Esterification process：Precision weighs the refined unrighted acid 500mg after inclusion, is placed in 50mL volumetric flasks, according to
Secondary addition ether: n-hexane (1: 1) 10mL mixed solvents, 10mL methanol, 0.5mol/LKOH/CH3OH solution 10mL, are placed
60min, adds water to 50mL, takes supernatant anhydrous sodium sulfate to remove trace water stand-by.Supernatant 1mL is taken in 10mL volumetric flasks
In, plus n-hexane is settled to scale, shakes up, it is to be measured.
Experimental result：Under above-mentioned chromatographic condition, methyl oleate, methyl linoleate standard items are measured, bid is obtained
Directrix curve；To do not include Silybum Marianum Gaertn Seed Oil, inclusion after refined thing be measured, oleic acid purity and Asia are gone out according to calculated by peak area
Oleic acid purity, and calculate the yield after inclusion.Determined and understood according to gas chromatography, measured and do not include oleic acid in Silybum Marianum Gaertn Seed Oil
Content is 25%, and linoleic acid content is 50%, and the oleic acid content after inclusion is 27.7%, and linoleic acid content is 55.5%, is received
Rate is 87%.
Embodiment 2：
1g urea is dissolved in 4mL95% ethanol, then 70 DEG C of heating water bath dissolvings are cooled to 60 DEG C, by urine oil than being 3: 1
Refined Silybum Marianum Gaertn Seed Oil (BHT that volume fraction of ethanol is 0.05% is added before sample-adding) is added, is stirred at reflux at 60 DEG C
30min, is cooled to after room temperature, sealing and is placed on inclusion crystallization in -15 DEG C of refrigerator.Inclusion compound, rapid suction filtration (filter are taken out after 24h
Cake is washed 3 times with ethanol), filtrate decompression concentration shoots more than half ethanol, uses n-hexane extraction unrighted acid, n-hexane
Layer is washed with deionized to PH 5~6, the appropriate anhydrous sodium sulfate of addition, dry 5h, suction filtration, and it is to obtain that revolving, which removes n-hexane,
Refined unrighted acid.Method of testing embodiment 1, determines according to gas chromatography and understands, the oleic acid content after inclusion
For 31.7%, linoleic acid content is 62.5%, and yield is 78%.
Embodiment 3：
1g urea is dissolved in 4mL95% ethanol, then 70 DEG C of heating water bath dissolvings are cooled to 60 DEG C, by urine oil than being 4: 1
Refined Silybum Marianum Gaertn Seed Oil (BHT that volume fraction of ethanol is 0.05% is added before sample-adding) is added, is stirred at reflux at 60 DEG C
30min, is cooled to after room temperature, sealing and is placed on inclusion crystallization in -15 DEG C of refrigerator.Inclusion compound, rapid suction filtration (filter are taken out after 24h
Cake is washed 3 times with ethanol), filtrate decompression concentration shoots more than half ethanol, uses n-hexane extraction unrighted acid, n-hexane
Layer is washed with deionized to PH 5~6, the appropriate anhydrous sodium sulfate of addition, dry 5h, suction filtration, and it is to obtain that revolving, which removes n-hexane,
Refined unrighted acid.Method of testing embodiment 1, determines according to gas chromatography and understands, the oleic acid content after inclusion
For 31.3%, linoleic acid content is 64.6%, and yield is 60%.
Claims (8)
1. a kind of method of the extraction purification unrighted acid in Silybum Marianum Gaertn Seed Oil, it is characterised in that comprise the following steps：
(1) urea is added into solvent, dissolve by heating, then cool, antioxidant added thereto, after add milk thistle
Oil, is then stirred at reflux and is cooled to room temperature, and inclusion crystallization under freezing conditions, obtains inclusion compound after sealing；
(2) inclusion compound, rapid suction filtration are taken out after certain time, filter cake is washed several times with ethanol, filtrate decompression concentration shoots one
More than half ethanol, uses n-hexane extraction unrighted acid, and n-hexane layer is washed with deionized to pH 5~6, is added appropriate
Anhydrous sodium sulfate, dry 4~5h, suction filtration, it is to obtain refined unrighted acid that revolving, which removes n-hexane,.
2. according to the method described in claim 1, it is characterised in that described solvent is 95% ethanol or 95% methanol, urea
Addition be that 0.8-1.2g urea is added per mL ethanol, the ratio of urea and Silybum Marianum Gaertn Seed Oil is 2~3: 1.
3. according to the method described in claim 1, it is characterised in that the condition of heating for dissolving is that 65-75 DEG C of heating water bath is molten
Solution, is then cooled to 55-60 DEG C.
4. according to the method described in claim 1, it is characterised in that the antioxidant is BHT or vitamin E, antioxidant
Addition be solvent volume 0.05%.
5. according to the method described in claim 1, it is characterised in that the addition of Silybum Marianum Gaertn Seed Oil is 1/3 (w/w) of urea.
6. according to the method described in claim 1, it is characterised in that the condition being stirred at reflux is to be stirred at reflux at 55-65 DEG C
30-35min。
7. according to the method described in claim 1, it is characterised in that the condition of inclusion crystallization is to be carried out in -15 DEG C of refrigerator
Inclusion crystallization.
8. the unrighted acid that the method described in any one of claim 1~7 is prepared is being prepared for preventing or treating
Or the application in the medicine of alleviation high fat of blood.
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|---|---|---|---|
| CN201710479047.4A CN107090357A (en) | 2017-06-21 | 2017-06-21 | A kind of method of the extraction purification unrighted acid in Silybum Marianum Gaertn Seed Oil |
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| CN201710479047.4A CN107090357A (en) | 2017-06-21 | 2017-06-21 | A kind of method of the extraction purification unrighted acid in Silybum Marianum Gaertn Seed Oil |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107595910A (en) * | 2017-09-08 | 2018-01-19 | 江苏中兴药业有限公司 | A kind of Silybum Marianum Gaertn Seed Oil composition and its application |
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