CN1208308C - Process for extracting, preparing and purifying docosahexenoic acid ethyl ester from shrimp podwer - Google Patents
Process for extracting, preparing and purifying docosahexenoic acid ethyl ester from shrimp podwer Download PDFInfo
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- CN1208308C CN1208308C CN03113397.5A CN03113397A CN1208308C CN 1208308 C CN1208308 C CN 1208308C CN 03113397 A CN03113397 A CN 03113397A CN 1208308 C CN1208308 C CN 1208308C
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- ethyl ester
- acid ethyl
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- 241000238557 Decapoda Species 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims abstract description 15
- TYLNXKAVUJJPMU-UHFFFAOYSA-N ethyl docosa-2,4,6,8,10,12-hexaenoate Chemical compound CCCCCCCCCC=CC=CC=CC=CC=CC=CC(=O)OCC TYLNXKAVUJJPMU-UHFFFAOYSA-N 0.000 title claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000000605 extraction Methods 0.000 claims abstract description 11
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 11
- 239000000741 silica gel Substances 0.000 claims abstract description 9
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 9
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 6
- 238000010992 reflux Methods 0.000 claims abstract description 5
- 238000005406 washing Methods 0.000 claims abstract description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 4
- 238000010828 elution Methods 0.000 claims abstract description 4
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 4
- 239000007788 liquid Substances 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 229960001866 silicon dioxide Drugs 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 239000006228 supernatant Substances 0.000 claims description 4
- 241000370738 Chlorion Species 0.000 claims description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 3
- 239000008367 deionised water Substances 0.000 claims description 3
- 229910021641 deionized water Inorganic materials 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 238000010025 steaming Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 239000003208 petroleum Substances 0.000 abstract description 3
- 238000001914 filtration Methods 0.000 abstract description 2
- 239000002244 precipitate Substances 0.000 abstract description 2
- 150000002632 lipids Chemical class 0.000 abstract 2
- 241000143060 Americamysis bahia Species 0.000 abstract 1
- TYLNXKAVUJJPMU-DNKOKRCQSA-N Docosahexaenoic acid ethyl ester Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(=O)OCC TYLNXKAVUJJPMU-DNKOKRCQSA-N 0.000 abstract 1
- 239000003480 eluent Substances 0.000 abstract 1
- GYBMSOFSBPZKCX-UHFFFAOYSA-N sodium;ethanol;ethanolate Chemical compound [Na+].CCO.CC[O-] GYBMSOFSBPZKCX-UHFFFAOYSA-N 0.000 abstract 1
- 235000013882 gravy Nutrition 0.000 description 12
- MBMBGCFOFBJSGT-KUBAVDMBSA-N docosahexaenoic acid Natural products CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229960004756 ethanol Drugs 0.000 description 4
- 239000003921 oil Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000000050 nutritive effect Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000003252 repetitive effect Effects 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 108010022579 ATP dependent 26S protease Proteins 0.000 description 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- 241001131796 Botaurus stellaris Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000206602 Eukaryota Species 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000001994 activation Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 229940088623 biologically active substance Drugs 0.000 description 1
- 230000004641 brain development Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000008935 nutritious Nutrition 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a method for extracting, preparing and purifying docosahexaenoic acid ethyl ester from shrimp podwer. Shrimp podwer is mixed with petroleum ether, refluxing extraction is carried out at 60 to 90 DGE C, petroleum ether is recovered, and total lipids are obtained through dryness. The obtained total lipids are mixed with 5% of sodium ethylate-ethanol solution, reaction is carried out for 2 to 5 hours in the dark at 50 to 70 DGE C, precipitates are removed through filtration, ethanol is evaporated, washing is carried out with water, a lower water layer is removed after standing layering, washing is carried out with water repeatedly until the pH value reaches 7, and unsaturated fatty acid ethyl ester is obtained after dryness is carried out with anhydrous sodium sulfate. Silver-silica gel columns are coated on the obtained unsaturated fatty acid ethyl ester for chromatography, gradient elution is carried out with propanone-n-hexane solution, eluent is collected partially, solvent is evaporated through pressure reduction, and high-purity docosahexenoic acid ethyl ester is obtained.
Description
One, technical field
The present invention relates to docosahexenoic acid ethyl ester and shrimp podwer.
Two, background technology
Salted shrimp gravy is a kind of ocean protozoon of filter-feeding, is shrimps unicellular lower eukaryote nutritious, delicious flavour.Salted shrimp gravy not only contains rich in protein, but also contains abundant unsaturated fatty acids, and wherein 22 carbon, six acid (DHA) account for 9.79% of total fatty acids.
According to a series of studies show that in recent years, DHA has reducing blood-fat, hypotensive, promotion brain development, important physiological function such as the interior resistance of oxidation of control agent, playing an important role at the 26S Proteasome Structure and Function of biometric safeguard film, treatment cardiovascular disorder and anti-inflammatory, aspect such as anticancer, is the necessary biologically active substance of people and animal growth.Fields such as medicine, protective foods and makeup have been widely used at present.Because its ethyl ester is generally used in the easy oxidation of unsaturated fatty acids, promptly docosahexenoic acid ethyl ester (DHA-E) after DHA-E enters human body, is hydrolyzed into activeconstituents DHA.
" technology for preapring served shrimp protein powder " (patent No. CN01107982.7) introduced a kind of method for preparing salted shrimp protein powder.The present invention improves on this basis.
Three, summary of the invention
The objective of the invention is to obtain the method for high-quality docosahexenoic acid ethyl ester in order to provide a kind of from shrimp podwer extraction, preparation, purifying.
Technical scheme of the present invention is as follows:
A kind of method from shrimp podwer extraction, preparation, purifying docosahexenoic acid ethyl ester, it is made up of the following step:
Step 1, with shrimp podwer and sherwood oil mixed by 9～12 liters of 1 kilogram of ratios, under 60～90 ℃, reflux extraction, sherwood oil is reclaimed in underpressure distillation, through vacuum-drying, red-brown oily matter, be total fat,
Step 2, with total fat and the 5% sodium ethylate-ethanolic soln of the step 1 gained mixed by weight 1 to 3～5, in 50～70 ℃ water-bath, heat, in dark, reacted 2～5 hours, remove by filter and precipitate the ethanol that boils off in the filtrate, use distilled water wash oily matter, discard lower aqueous layer behind the standing demix, supernatant liquid washes with water repeatedly, reaches 7 until pH, behind anhydrous sodium sulfate drying, obtain reddish-brown liquid, be unsaturated fatty acid ethyl ester
Be coated with silver-colored silicagel column on step 3, the unsaturated fatty acid ethyl ester and carry out chromatography,, get highly purified docosahexenoic acid ethyl ester with acetone-hexane solution gradient elution, fraction collection elutriant, pressure reducing and steaming solvent with the step 2 gained.
The step 2 of aforesaid method at the middle and upper levels liquid wash with water, the pH value is difficult for reaching at 7 o'clock, can add the dilute hydrochloric acid neutralization, makes its pH reach 7, and with saturated NaCl solution washing, is washed till no chlorion with deionized water again.
Method of the present invention is economical and practical, can obtain highly purified docosahexenoic acid ethyl ester, is applicable to suitability for industrialized production.
Four, embodiment
The pre-treatment of embodiment 1. salted shrimp gravys:
(1) salted shrimp gravy is cleaned with clear water, removed weeds with floating method, impurity such as halogen fly, halogen maggot are that the pure bittern of 15Be '～18Be ' takes suspension method to remove materials such as the external silt of salted shrimp gravy with concentration then, must clean salted shrimp gravy after the cleaning and filtering;
(2), make dried prawn slice or dried shrimp med with the temperature drying of clean salted shrimp gravy with 50～60 ℃.Because salted shrimp gravy is rich in various active materials such as unsaturated fatty acids, protein, the height of dry materials temperature and the length of time of drying are very big to the influence of salted shrimp gravy thermo-sensitivity nutritive substance, temperature is high more, time is long more, the loss of thermo-sensitivity nutritive substance is many more, and is very unfavorable to the salted shrimp gravy processing that DHA content is higher.So this invention adopts below 60 ℃, vacuum, vibrate, fill nitrogen, the production of drying and crushing integrated industrial, both satisfied product processing needs, lowered manufacturing procedure and production cost again greatly;
(3) dried salted shrimp gravy is ground into 180～250 purpose dry powder;
(4) with exsiccant shrimp podwer blower separating impurity, this process can once be finished, and also wind separates repeatedly.
Take the evaluation of shrimp podwer that above-mentioned technical process makes, have very high technical indicator: protein 60% by the national Ministry of Agriculture; Fat 15%; Moisture is not more than 5%; Ash content (containing not capacitive of chitin) is not more than 12%, and inorganic arsenic is not more than 1 mg/kg.Wherein DHA accounts for 9.79% of total fat.
Embodiment 2.DHA extraction, preparation and purifying:
(1) at first, from shrimp podwer, extract total fat
The extraction of total fat in the salted shrimp gravy: take by weighing 300 gram shrimp podwers, mix with 2700 milliliters of sherwood oils, under 60～90 ℃, reflux extraction, decompression and solvent recovery through vacuum-drying, gets red-brown oily matter 110 grams, is total fat.
(2) secondly, with unsaturated fatty acid ethyl esterization.
5% sodium ethylate-ethanolic soln 330 grams are mixed with oily matter.Place three-necked flask, connect condensation reflux unit, heat in 50～70 ℃ of water-baths, reaction is 2 hours in dark.After reaction finishes, remove by filter precipitation, boil off the ethanol in the filtrate, and use the distilled water repetitive scrubbing, discard lower aqueous layer behind the standing demix.Supernatant liquid is wanted repetitive scrubbing, adds the dilute hydrochloric acid neutralization in case of necessity, reaches till 7 until the pH value, and with saturated NaCl solution washing, be washed till no chlorion with deionized water again after, at last with behind the anhydrous sodium sulfate drying, obtain reddish-brown liquid, promptly get unsaturated fatty acid ethyl ester.
In step (1) with 3600 milliliters of petroleum ether extractions; With 550 gram 5% sodium ethylate-ethanolic solns, its result is constant substantially in step (2).
(3) then, employing is coated with silver-colored silica gel column chromatography-gradient concentration elution method purifying DHA:
A. be coated with the preparation of silver-colored silicagel column:
The 100g silica gel for chromatography is added in the 200ml dehydrated alcohol, mix into suspension, add silver nitrate solution (10g AgNO
3Add in the ethanol of 35ml 70%), restir 10min boils off ethanol.The silver-colored silica gel of being coated with of gained is placed baking oven,, after the cooling, preserve in the lucifuge place in 120 ℃ of high-temperature activations (more than the 12h).
Cut-off directly is 2.5cm, the chromatography column that high 10cm is above.Get activatory and be coated with silver-colored silica gel 20g and add about 40ml normal hexane and make suspension, adorn post, make to be coated with about the high 9cm of silver-colored silicagel column post.
B. application of sample, wash-out:
Drip 1.0g polyunsaturated fatty acid ethyl ester on cylinder, the preparation acetone concentration is that each 25 milliliters of the acetone-hexane solutions of 0.5%, 1%, 5%, 10%, 15%, 20% (v/v) are as elutriant.By concentration wash-out successively from low to high, flow rate control is collected the effluent liquid of each different concns gradient respectively and is done gas chromatographic analysis at 2.0-1.3ml/min.Reaching 20% in the elutriant acetone concentration is, divided for 5 steps collected, the docosahexenoic acid ethyl ester purity that obtains is followed successively by 91.29%, 97.26%, 97.6%, 97.89%, 100% highly purified docosahexenoic acid ethyl ester, and wherein the yield of 100% purity is about 20%.UV detects demonstration, and it has an absorption peak in the 200nm place in normal hexane, and its EI-MS detects, and its M/Z value is 357, and is all consistent with standard specimen (purchasing the company in sigma).
More than experiment can obtain approximation through amplifying, and shows that this preparation, purification process are applicable to suitability for industrialized production.
Claims (2)
1. method from shrimp podwer extraction, preparation, purifying docosahexenoic acid ethyl ester is characterized in that it is made up of the following step:
Step 1, with shrimp podwer and sherwood oil mixed by 9～12 liters of 1 kilogram of ratios, under 60～90 ℃, reflux extraction, sherwood oil is reclaimed in underpressure distillation, through vacuum-drying, red-brown oily matter, be total fat,
Step 2, with total fat and the 5% sodium ethylate-ethanolic soln of the step 1 gained mixed by weight 1 to 3～5, in 50～70 ℃ water-bath, heat, in dark, reacted 2～5 hours, remove by filter precipitation, boil off the ethanol in the filtrate, use distilled water wash oily matter, discard lower aqueous layer behind the standing demix, supernatant liquid washes with water repeatedly, reach 7 until pH, behind anhydrous sodium sulfate drying, obtain reddish-brown liquid, be unsaturated fatty acid ethyl ester
Be coated with silver-colored silicagel column on step 3, the unsaturated fatty acid ethyl ester and carry out chromatography,, get docosahexenoic acid ethyl ester with acetone-hexane solution gradient elution, fraction collection elutriant, pressure reducing and steaming solvent with the step 2 gained.
2. method according to claim 1 is characterized in that: in step 2, supernatant liquid washes with water, adds the hydrochloric acid neutralization, makes its pH reach 7, and with saturated NaCl solution washing, is washed till no chlorion with deionized water again.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN03113397.5A CN1208308C (en) | 2003-05-08 | 2003-05-08 | Process for extracting, preparing and purifying docosahexenoic acid ethyl ester from shrimp podwer |
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| CN03113397.5A CN1208308C (en) | 2003-05-08 | 2003-05-08 | Process for extracting, preparing and purifying docosahexenoic acid ethyl ester from shrimp podwer |
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| CN1208308C true CN1208308C (en) | 2005-06-29 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101796014A (en) * | 2007-06-29 | 2010-08-04 | 马泰克生物科学公司 | Production and purification of esters of polyunsaturated fatty acids |
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| CN104262076B (en) * | 2014-09-04 | 2016-04-13 | 宁波大红鹰生物工程股份有限公司 | A kind of method utilizing Silver Nitrate silica gel chromatography purification plant origin squalene |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101796014A (en) * | 2007-06-29 | 2010-08-04 | 马泰克生物科学公司 | Production and purification of esters of polyunsaturated fatty acids |
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