CN109971539A - A kind of phosphatide and fish oil extracting method for tuna by-product - Google Patents
A kind of phosphatide and fish oil extracting method for tuna by-product Download PDFInfo
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- CN109971539A CN109971539A CN201910201689.7A CN201910201689A CN109971539A CN 109971539 A CN109971539 A CN 109971539A CN 201910201689 A CN201910201689 A CN 201910201689A CN 109971539 A CN109971539 A CN 109971539A
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- clear liquid
- mixed liquor
- fish oil
- phosphatide
- tuna
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- 238000000034 method Methods 0.000 title claims abstract description 71
- 235000021323 fish oil Nutrition 0.000 title claims abstract description 59
- 239000006227 byproduct Substances 0.000 title claims abstract description 31
- 239000007788 liquid Substances 0.000 claims abstract description 71
- 238000000605 extraction Methods 0.000 claims abstract description 60
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims abstract description 37
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 150000002632 lipids Chemical class 0.000 claims abstract description 16
- 238000010438 heat treatment Methods 0.000 claims abstract description 15
- 239000000047 product Substances 0.000 claims abstract description 15
- 238000002156 mixing Methods 0.000 claims abstract description 13
- 239000013049 sediment Substances 0.000 claims abstract description 7
- 230000010355 oscillation Effects 0.000 claims abstract description 5
- 238000001035 drying Methods 0.000 claims abstract description 4
- 238000005303 weighing Methods 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 105
- 239000000284 extract Substances 0.000 claims description 15
- 239000006228 supernatant Substances 0.000 claims description 14
- 238000005119 centrifugation Methods 0.000 claims description 12
- 230000032050 esterification Effects 0.000 claims description 12
- 238000005886 esterification reaction Methods 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 7
- 229930195729 fatty acid Natural products 0.000 claims description 7
- 239000000194 fatty acid Substances 0.000 claims description 7
- 150000004665 fatty acids Chemical class 0.000 claims description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 229910021642 ultra pure water Inorganic materials 0.000 claims description 5
- 239000012498 ultrapure water Substances 0.000 claims description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- -1 bis- chloroethene Alkane Chemical class 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 210000001835 viscera Anatomy 0.000 description 12
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000012071 phase Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- 238000007654 immersion Methods 0.000 description 5
- 235000013305 food Nutrition 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 235000013373 food additive Nutrition 0.000 description 2
- 239000002778 food additive Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 238000003808 methanol extraction Methods 0.000 description 2
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 150000003904 phospholipids Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 238000010183 spectrum analysis Methods 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 206010020466 Hunger Diseases 0.000 description 1
- 241001125831 Istiophoridae Species 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000002539 daughter ion scan Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- IPVSQRLZENDNRL-KVVVOXFISA-N hexadecanoic acid;(z)-octadec-9-enoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O IPVSQRLZENDNRL-KVVVOXFISA-N 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
- C07F9/103—Extraction or purification by physical or chemical treatment of natural phosphatides; Preparation of compositions containing phosphatides of unknown structure
-
- 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
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/10—Production of fats or fatty oils from raw materials by extracting
-
- 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
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Meat, Egg Or Seafood Products (AREA)
- Fats And Perfumes (AREA)
Abstract
The invention discloses a kind of phosphatide for tuna by-product and fish oil extracting methods, the following steps are included: first weighing every 10 grams of tuna by-product as object to be extracted, it is carried out by clear liquid extraction method repeatedly to extract and obtains mixing clear liquid, then mixing clear liquid heating is made 1,2- dichloroethanes evaporative removal, obtains D lipid mixture；Then 100mL acetone is added to it after D lipid mixture being cooled to room temperature, refrigerated centrifuge after oscillation extraction retransfers and obtains E clear liquid after lower clear liquid and obtain finished product phosphatide after remaining sediment drying；Finally so that acetone is volatilized completely the heating of E clear liquid, obtains finished product fish oil.The present invention can have the characteristics that extraction efficiency is high, safety is good simultaneously.
Description
Technical field
The present invention relates to the extracting method of a kind of tunny fish oil and phosphatide, especially a kind of phosphorus for tuna by-product
Rouge and fish oil extracting method.
Background technique
The characteristics of tuna is because of its high nutrition, high edible value is generally processed into varieties of food items by full generation at present
Boundary consumer's likes；But due to the edible part of tuna only temporary the 50~70% of its gross weight, and such as internal organ in tuna
A large amount of processing byproducts can only then be abandoned as feed or directly, to cause waste and the environmental pressure of resource.Fish internal organ
In rich in the functional greases such as phosphatide, glyceride, and difference of the tunny fish oil compared to common fish oil is to be it rich in ω -3
How simply and effectively polyunsaturated fatty acid, this is that human body is indispensable but the important nutrient that can not synthesize, therefore
The phosphatide containing omega-3 polyunsaturated fatty acids is extracted from tuna then becomes producer's generally wanted problems faced.
Currently used lipids extraction method has solvent extraction, supercritical CO2Extraction and solid phase extraction, wherein molten
Agent extraction compared to other two methods because its it is commonly available to the higher phosphatide of purity and to equipment and capital investment requirements it is lower due to
It is used widely.Conventional solvent extraction mainly has Bligh&Dyer method, Folch method, MTBE method and ethanol immersion etc.,
However the above method or need to be extracted as solvent using the stronger reagent of toxicity, it is not suitable for food industry；Or exists and mention
The problem of taking low efficiency, falling flat.It can be provided simultaneously with that extraction efficiency is high, safety is good therefore, it is necessary to one kind
Tuna phosphatide extracting method, so as to be directed to tuna internal organ fat characteristics, be simple and efficient to tuna by-product
It develops and utilizes.
Summary of the invention
The object of the present invention is to provide a kind of phosphatide for tuna by-product and fish oil extracting methods.It can
Have the characteristics that extraction efficiency is high, safety is good simultaneously.
Technical solution of the present invention: a kind of phosphatide and fish oil extracting method for tuna by-product, including following step
It is rapid:
1. the tuna by-product for weighing every 10 grams is treated extract by clear liquid extraction method and is mentioned as object to be extracted
It takes, obtains A clear liquid；The clear liquid extraction method is to be put into object to be extracted to vibrate in the 1,2- dichloroethanes methyl alcohol mixed liquor of 40mL to mix
It is even, a1 mixed liquor is obtained, refrigerated centrifuge after the ultrapure water of 10mL is then added into a1 mixed liquor, then removes that obtain A after clear liquid clear
Liquid, remaining supernatant and solid content are B mixed liquor；
2. extracted by above-mentioned clear liquid extraction method to B mixed liquor using B mixed liquor as object to be extracted, it is clear to obtain B1
Liquid and B2 mixed liquor；
3. being extracted by above-mentioned clear liquid extraction method to B2 mixed liquor using B2 mixed liquor as object to be extracted, obtaining B3
Clear liquid；
4. obtaining mixing clear liquid after A clear liquid, B1 clear liquid and B3 clear liquid are merged, mixing clear liquid heating is then made into 1,2- bis-
Chloroethanes evaporative removal obtains C lipid mixture；
5. 100mL acetone, refrigerated centrifuge after oscillation extraction is added to it after C lipid mixture is cooled to room temperature, then take
D clear liquid is obtained after lower clear liquid obtains finished product phosphatide after remaining sediment drying；
6. making acetone volatilize completely the heating of D clear liquid, finished product fish oil is obtained.
In a kind of phosphatide and fish oil extracting method for tuna by-product above-mentioned, the step 1. in 1,2- bis-
Chloroethanes methyl alcohol mixed liquor is mixed by 1,2- dichloroethanes and methanol with the volume ratio of 1:2.
In a kind of phosphatide and fish oil extracting method for tuna by-product above-mentioned, the step 1. in a1 mixed liquor
Centrifugation rate be 10000r/min, centrifugation time be 10 minutes；The step 5. in the centrifugation rate of C lipid mixture be
8000r/min, centrifugation time are 6 minutes.
In a kind of phosphatide and fish oil extracting method for tuna by-product above-mentioned, the step 4. in pass through rotation
Evaporimeter heats mixing clear liquid, and the heating temperature for mixing clear liquid is 70 DEG C；The step 6. in pass through Rotary Evaporators
D clear liquid is heated, the heating temperature of D clear liquid is 35 DEG C.
In a kind of phosphatide and fish oil extracting method for tuna by-product above-mentioned, the step 5. in blown by nitrogen
Instrument dries up remaining sediment.
In a kind of phosphatide and fish oil extracting method for tuna by-product above-mentioned, the esterification of the finished product fish oil
Method the following steps are included:
1. shaken well after every 0.1g fish oil is mixed with the NaOH-MeOH solution of 2mL, then 30 are heated under 65 DEG C of environment
Minute, obtain F mixed liquor；
2. being cooled to room temperature after F mixed liquor is taken out, the BF of 2mL is added3- MeOH solution shaken well, then at 65 DEG C
It is heated 3 minutes under environment, obtains G mixed liquor；
3. being cooled to room temperature after G mixed liquor is taken out, the n-hexane for adding 2mL is extracted, and is added 2mL's in extraction process
It is saturated NaCl solution washing and obtains H supernatant after extraction obtains supernatant；
4. the anhydrous sodium sulfate of 1/10 volume is added into H supernatant, completely remove the water of the trace in solution, then
Supernatant is taken, finished product esterification fatty acid is obtained.
Compared with prior art, the present invention can be in once extracting to tuna by-product by said extracted technique
Available phosphatide and fish oil are respectively obtained in journey, to improve the utilization rate to tuna, and are played to simplify and are extracted step
Effect that is rapid and improving extraction efficiency；By using 1,2- dichloroethanes methyl alcohol mixed liquor as solvent to the phosphorus in tuna internal organ
Rouge extracts, and can effectively improve the pick-up rate to phosphatide and fish oil compared to other solvents, and due to 1,2- dichloroethanes
Be allow in national standard using food additives and food processing aid, so as to improve present invention safety at the extraction
Property；1,2- dichloroethanes methyl alcohol mixed liquor can also effectively improve more insatiable hungers in extracted fish oil as the extracting mode of solvent
And content of fatty acid, to make the fish oil extracted that there is more excellent utilization rate；Pass through the multiple extraction work to tuna
Skill can further increase the extraction effect of the phosphatide and fish oil to tuna during the extraction process, make phosphatide in tuna
Recovery rate can reach 71.7%, and the recovery rate of fish oil can reach 97.6%.
In addition, the present invention is by the characteristic and 1 of tuna by-product, the extraction effect of 2- dichloroethanes methyl alcohol mixed liquor into
The corresponding technological parameter of one-step optimization, to improve extraction stability and extraction effect of the invention；By to fish oil first
It can be effectively prepared into detectable esterification fatty acid by the optimization of esterification process, and be further simplified its preparation process,
To facilitate producer to its chromatography and mass spectral analysis, and reduce its error when detecting.So the present invention is enough while having
The feature that extraction efficiency is high, safety is good.
Detailed description of the invention
Fig. 1 is extraction yield comparison diagram of the Different Extraction Method to phosphatide and fish oil；
Fig. 2 is the phospholipid species that Different Extraction Method obtains and relative abundance comparison diagram.
Specific embodiment
Below with reference to embodiment, the present invention is further illustrated, but is not intended as the foundation limited the present invention.
Embodiment.A kind of phosphatide and fish oil extracting method for tuna by-product, comprising the following steps:
1. taking its internal organ to smash slurrying anxious freeze after tuna thaws 1 hour, tuna by-product is obtained, is then weighed every
10 grams of tuna by-product is treated extract by clear liquid extraction method and is extracted as object to be extracted, obtains A clear liquid；It is described
Clear liquid extraction method is to be put into object to be extracted to vibrate in 1, the 2- dichloroethanes methyl alcohol mixed liquor of 40mL to mix, and obtains a1 mixed liquor,
Then refrigerated centrifuge after the ultrapure water of 10mL is added into a1 mixed liquor, then removes and obtains A clear liquid after clear liquid, remaining supernatant and
Solid content is B mixed liquor；
2. extracted by above-mentioned clear liquid extraction method to B mixed liquor using B mixed liquor as object to be extracted, it is clear to obtain B1
Liquid and B2 mixed liquor；
3. being extracted by above-mentioned clear liquid extraction method to B2 mixed liquor using B2 mixed liquor as object to be extracted, obtaining B3
Clear liquid；
4. obtaining mixing clear liquid after A clear liquid, B1 clear liquid and B3 clear liquid are merged, mixing clear liquid heating is then made into 1,2- bis-
Chloroethanes evaporative removal obtains C lipid mixture；
5. 100mL acetone, refrigerated centrifuge after oscillation extraction is added to it after C lipid mixture is cooled to room temperature, then take
D clear liquid is obtained after lower clear liquid obtains finished product phosphatide after remaining sediment drying；
6. making acetone volatilize completely the heating of D clear liquid, finished product fish oil is obtained.
The step 1. in 1,2- dichloroethanes methyl alcohol mixed liquor by 1,2- dichloroethanes (1,2-DCE) and methanol with 1:
2 volume ratio (1:2, v/v) mixes.
The step 1. in the centrifugation rate of a1 mixed liquor be 10000r/min, centrifugation time is 10 minutes；The step
5. the centrifugation rate of middle C lipid mixture is 8000r/min, centrifugation time is 6 minutes.
The step 4. in by Rotary Evaporators to mixing clear liquid heat, mix clear liquid heating temperature be 70
℃；The step 6. in D clear liquid is heated by Rotary Evaporators, the heating temperature of D clear liquid is 35 DEG C.
The step 5. in remaining sediment is dried up by nitrogen evaporator.
The esterification method of the finished product fish oil the following steps are included:
1. shaken well after every 0.1g fish oil is mixed with the NaOH-MeOH solution of 2mL, then 30 are heated under 65 DEG C of environment
Minute, obtain F mixed liquor；
2. being cooled to room temperature after F mixed liquor is taken out, the BF of 2mL is added3- MeOH solution shaken well, then at 65 DEG C
It is heated 3 minutes under environment, obtains G mixed liquor；
3. being cooled to room temperature after G mixed liquor is taken out, the n-hexane for adding 2mL is extracted, and is added 2mL's in extraction process
It is saturated NaCl solution washing and obtains H supernatant after extraction obtains supernatant；
4. the anhydrous sodium sulfate of 1/10 volume is added into H supernatant, completely remove the water of the trace in solution, then
Supernatant is taken, finished product esterification fatty acid is obtained；By the way that fish oil esterification can be used for the gas-chromatography to fish oil, liquid chromatogram
And mass spectral analysis.
The working principle of the invention: the present invention is using 1,2- dichloroethanes methyl alcohol mixed liquor as solvent to tuna by-product
It extracts to obtain phosphatide and fish oil, can effectively improve extraction efficiency and the yield to phosphatide and fish oil, and effectively improve
Content of polyunsaturated fatty acid in fish oil, to make it have good extraction effect.1,2- dichloroethanes itself is food
Additive and food processing aid, to enough effectively prevent extracting obtained phosphatide and fish oil by the hidden of solvent effect residual toxicity
Suffer from, improves the safety of phosphatide and fish oil after extraction.Featured configuration corresponding extraction work of the present invention also according to tuna
Skill and parameter realize the effective use to tuna by-product to further increase the extraction efficiency to phosphatide and fish oil.
Experimental example: pass sequentially through 1,2-DCE extraction method, Bligh&Dyer method, Folch method, MTBE method, ethanol immersion and
Step of the present invention 1. -4. described in 1,2-DCE/ methanol extraction extract lipid mixture, then will extract obtained lipid
Mixture through the invention 5., 6. extract to obtain phosphatide and fish oil step by method.
Wherein 1,2-DCE extraction method is to replace 1,2- dichloroethanes methyl alcohol mixed liquor as molten 1,2- dichloroethane solution
Agent, by step of the present invention 1. -4. described in extracting method extract.
Bligh&Dyer method is that the chloroform/methanol mixed liquor of 1:2 volume ratio is replaced 1,2- dichloroethanes methyl alcohol mixed liquor
As solvent, by step of the present invention 1. -4. described in extracting method extract.
Folch method is to replace 1,2- dichloroethanes methyl alcohol mixed liquor as molten the chloroform/methanol mixed liquor of 2:1 volume ratio
Agent, by step of the present invention 1. -4. described in extracting method extract.
The specific extraction step of MTBE method are as follows: weigh the tuna every 10g of by-product sample, 9mL methanol is added and vibrates mixed
It is even, 21mL methyl tertiary butyl ether(MTBE) is added, is vibrated 1 hour at room temperature.Ultrapure water 7.5mL is added later, reacts 10 points at room temperature
Clock, then with 10,000r/min high speed refrigerated centrifuge 10 minutes.Upper organic phase is collected, lower layer is with by 3mL methanol, 10mL methyl
The mixed solution reextraction that tertbutyl ether and 2.5mL ultrapure water are constituted, takes upper organic phase, repeats to extract 2 times.After merging
Organic phase move into bottle in, evaporate methyl tertiary butyl ether(MTBE) at 55 DEG C using Rotary Evaporators, obtain lipid mixture.
The specific extraction step of ethanol immersion (ETOH) are as follows: weigh the tuna every 10g of by-product sample, 150mL is added
95% ethyl alcohol, oscillation mix be placed in water-bath, in 45 DEG C extract 4 hours after filter.Filtrate is collected to round-bottomed flask
In, second alcohol and water is evaporated sufficiently at 50 DEG C using Rotary Evaporators, obtains lipid mixture.
Three groups of experimental groups, three groups of experimental group institutes are respectively set in 1,2-DCE/ methanol extraction of the present invention at the extraction
1,2- dichloroethanes and methanol volume ratio are respectively set to 1:2,1:1 and 2:1 in 1,2- dichloroethanes methyl alcohol mixed liquor,
It is remaining to be extracted by extracting method of the present invention.
Then the isolated phosphatide of extraction method and fish oil are weighed respectively, then phosphatide and fish is calculated by formula
Oily yield, wherein phosphatide yield/%=(phosphatide quality/sample quality) * 100%；Fish oil yield/%=(fish oil quality/sample
Quality) * 100%.
Experimental result is as shown in Figure 1, in terms of phosphatide extraction, and the yield of 1,2-DCE/ methanol method is in extraction mixed liquor
The increase of 1,2-DCE ratio and decline, when extract mixed liquor ratio be 1,2-DCE/ methanol (1:2, v/v) when for tuna
The yield highest of internal organ phosphatide, recovery rate reaches 71.7%, and 1,2-DCE rule is minimum.Meanwhile Bligh&Dyer method, Folch
For 3 kinds of common extracting methods of method and MTBE method to the yield of phosphatide compared to 1,2-DCE/ methanol method and 1,2-DCE method is higher,
But the reagents such as chloroform and methyl tertiary butyl ether(MTBE) used in wherein are opposite not to be suitable for food-processing industry.And ethanol immersion pair
The extracted amount of tuna internal organ phosphatide is also very low.
In terms of fish oil extraction, the yield of 1,2-DCE/ methanol method is with the increase for extracting 1,2-DCE ratio in mixed liquor
And increase, it is highest in 8 kinds of methods for the yield of tuna internal organ fish oil when the ratio of 1,2-DCE/ methanol is 2:1, reaches
To 97.6%, but 1, the 2-DCE/ methanol method and Folch method difference very little of its yield and other solvent ratios.Therefore, in gold
In terms of the extraction of marlin phosphatide and fish oil, 1,2-DCE/ methanol (1:2, v/v) method used in the present invention is more excellent method.
Experimental example 2: by fish oil esterification method of the present invention respectively to 6 parts of fish oil tests obtained in experimental example 1
Product carry out esterification technique, then utilize its fatty acid group of gas chromatography analysis to the esterification fatty acid that processing obtains respectively
At since 1,2-DCE method and ethanol immersion are lower for the phosphatide and fish oil yield of tuna internal organ, then not carried out to it
Iipidomics analysis.
Analytical conditions for gas chromatography specifically: chromatographic column is HP-88 capillary chromatographic column (30m*0.25mm, 0.2 μm)；It carries
Gas is high pure nitrogen；Constant current is 0.65mL/min；Sample volume is 1 μ L；Split ratio is 40: 1；Injector temperature is 250 DEG C；Heating
Program is 50 DEG C of initial temperature, rises to 220 DEG C after being kept for 2 minutes with 4 DEG C/min and maintains 15 minutes.
Testing result is as shown in table 1, detects 18 kinds of fatty acid in the fish oil that the above method extracts altogether, in composition
It is almost the same.In saturated fatty acid, based on palmitinic acid, stearic acid takes second place；In monounsaturated fatty acids, based on oleic acid, palm fibre
Palmitic acid oleic acid takes second place；In polyunsaturated fatty acid, based on DHA, EPA takes second place.Therefore, the above method is capable of the extraction of high quality
Polyunsaturated fatty acid in tuna internal organ, and 1 used in the present invention, 2-DCE/ methanol method is equal in the extraction of EPA and DHA
Better than other methods.
Fatty acid methyl ester chemistry component and content in 1 fish oil of table
Experimental example 3: liquid chromatography-mass spectrometry mirror is carried out to the phosphatide that each extracting method in experimental example 1 is extracted respectively
It is fixed, liquid phase chromatogram condition are as follows: chromatographic column is COSMOSILHILIC column (4.6 × 150mm, 5 μm)；Mobile phase A is to contain 0.1%
The acetonitrile solution of formic acid；Mobile phase B is the aqueous solution of the ammonium formate containing 20mmol/L and 0.1% formic acid；Flow rate of mobile phase 200
μL/min.2 μ L of sample volume；Gradient elution program: 0 to 3 minute, 95% mobile phase A is maintained；3 to 13 minutes, by mobile phase A from
95% is reduced to 70%；13 to 18 minutes, mobile phase A is reduced to 50% from 70%；18 to 23 minutes, maintain 50% mobile phase
A；23 to 24 minutes, mobile phase A is returned to 95% from 50% liter；24 to 32 minutes, maintain 95% mobile phase A.
Mass Spectrometry Conditions are as follows: detected using negative ion mode；Scanning range 450-950Da；Remove cluster voltage 60V；Focusing potential
200V；Ion source voltage 4500V；Removing cluster potential is 10V；Gas source 1:50psi；Gas source 2:60psi；Gas curtain gas 25psi；Desolventizing
500 DEG C of temperature；Daughter ion scans impact energy 30V.
Detecting obtained content of phospholipid, (A is 1,2-DCE/ methanol (1:2, v/v) method in figure as shown in Figure 2；B is 1,2-
DCE/ methanol (1:1, v/v) method；C is 1,2-DCE/ methanol (2:1, v/v) method；E is Bligh&Dyer method；F is Folch method；G is
MTBE method), phosphatide in the resulting tuna of Different Extraction Method extraction is analyzed it is found that 6 kinds of extracting methods are mentioning by above-mentioned
There are few difference, acquired results are also similar with existing testing result for influence during taking to tuna internal organ phosphatide constituent.
It proves that extracting method of the present invention can not only effectively extract phosphatide in tuna internal organ, can also largely mention
Take the phosphatide of the wherein chain containing omega-3 polyunsaturated fatty acids.
Claims (6)
1. a kind of phosphatide and fish oil extracting method for tuna by-product, which comprises the following steps:
1. the tuna by-product for weighing every 10 grams is treated extract by clear liquid extraction method and is extracted as object to be extracted,
Obtain A clear liquid；The clear liquid extraction method is to be put into object to be extracted to vibrate in 1, the 2- dichloroethanes methyl alcohol mixed liquor of 40mL to mix,
A1 mixed liquor is obtained, refrigerated centrifuge after the ultrapure water of 10mL is then added into a1 mixed liquor, then obtain A clear liquid after removing clear liquid,
Remaining supernatant and solid content are B mixed liquor；
2. B mixed liquor is extracted by above-mentioned clear liquid extraction method using B mixed liquor as object to be extracted, obtain B1 clear liquid and
B2 mixed liquor；
3. being extracted by above-mentioned clear liquid extraction method to B2 mixed liquor using B2 mixed liquor as object to be extracted, obtaining B3 clear liquid；
4. obtaining mixing clear liquid after A clear liquid, B1 clear liquid and B3 clear liquid are merged, mixing clear liquid heating is then made into 1,2-, bis- chloroethene
Alkane evaporative removal obtains C lipid mixture；
5. 100mL acetone, refrigerated centrifuge after oscillation extraction is added to it after C lipid mixture is cooled to room temperature, then remove clear
D clear liquid is obtained after liquid obtains finished product phosphatide after remaining sediment drying；
6. making acetone volatilize completely the heating of D clear liquid, finished product fish oil is obtained.
2. a kind of phosphatide and fish oil extracting method for tuna by-product according to claim 1, it is characterised in that:
The step 1. in 1,2- dichloroethanes methyl alcohol mixed liquor by 1,2- dichloroethanes and methanol with the mixing of the volume ratio of 1:2 and
At.
3. a kind of phosphatide and fish oil extracting method for tuna by-product according to claim 1, it is characterised in that:
The step 1. in the centrifugation rate of a1 mixed liquor be 10000r/min, centrifugation time is 10 minutes；The step 5. in C lipid
The centrifugation rate of mixture is 8000r/min, and centrifugation time is 6 minutes.
4. a kind of phosphatide and fish oil extracting method for tuna by-product according to claim 1, it is characterised in that:
The step 4. in by Rotary Evaporators to mixing clear liquid heat, mix clear liquid heating temperature be 70 DEG C；The step
Suddenly 6. in D clear liquid is heated by Rotary Evaporators, the heating temperature of D clear liquid is 35 DEG C.
5. a kind of phosphatide and fish oil extracting method for tuna by-product according to claim 1, it is characterised in that:
The step 5. in remaining sediment is dried up by nitrogen evaporator.
6. a kind of phosphatide and fish oil extracting method for tuna by-product according to claim 1, which is characterized in that
The esterification method of the finished product fish oil the following steps are included:
1. shaken well after every 0.1g fish oil is mixed with the NaOH-MeOH solution of 2mL, then 30 points are heated under 65 DEG C of environment
Clock obtains F mixed liquor；
2. being cooled to room temperature after F mixed liquor is taken out, the BF of 2mL is added3- MeOH solution shaken well, then under 65 DEG C of environment
Heating 3 minutes, obtains G mixed liquor；
3. being cooled to room temperature after G mixed liquor is taken out, the n-hexane for adding 2mL is extracted, and the saturation of 2mL is added in extraction process
NaCl solution washing obtains H supernatant after extraction obtains supernatant；
4. the anhydrous sodium sulfate of 1/10 volume is added into H supernatant, the water of the trace in solution is completely removed, is then taken
Clear liquid obtains finished product esterification fatty acid.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110668945A (en) * | 2019-09-29 | 2020-01-10 | 青岛利和生物科技有限公司 | Method for extracting DHA and EPA in fish oil by combining supercritical fluid |
| CN110862871A (en) * | 2019-11-13 | 2020-03-06 | 武汉轻工大学 | Method for efficiently enriching n-3PUFA lipid from aquatic product processing by-products |
| CN111812248A (en) * | 2020-07-23 | 2020-10-23 | 浙江工商大学 | Analysis and detection method for effectively screening phospholipids in krill oil |
| CN115011642A (en) * | 2022-05-24 | 2022-09-06 | 浙江工商大学 | Method for preparing structured lipid rich in EPA and DHA by using tuna |
| CN115436539A (en) * | 2022-09-20 | 2022-12-06 | 浙江工商大学 | Tuna variety and part identification method based on lipidomics analysis method |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110668945A (en) * | 2019-09-29 | 2020-01-10 | 青岛利和生物科技有限公司 | Method for extracting DHA and EPA in fish oil by combining supercritical fluid |
| CN110668945B (en) * | 2019-09-29 | 2022-02-15 | 青岛利和生物科技有限公司 | Method for extracting DHA and EPA in fish oil by combining supercritical fluid |
| CN110862871A (en) * | 2019-11-13 | 2020-03-06 | 武汉轻工大学 | Method for efficiently enriching n-3PUFA lipid from aquatic product processing by-products |
| CN111812248A (en) * | 2020-07-23 | 2020-10-23 | 浙江工商大学 | Analysis and detection method for effectively screening phospholipids in krill oil |
| CN115011642A (en) * | 2022-05-24 | 2022-09-06 | 浙江工商大学 | Method for preparing structured lipid rich in EPA and DHA by using tuna |
| CN115436539A (en) * | 2022-09-20 | 2022-12-06 | 浙江工商大学 | Tuna variety and part identification method based on lipidomics analysis method |
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