CN105062664A - Method for preparing and detecting oleic acid in degreased euphausia superba - Google Patents
Method for preparing and detecting oleic acid in degreased euphausia superba Download PDFInfo
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- CN105062664A CN105062664A CN201510439314.6A CN201510439314A CN105062664A CN 105062664 A CN105062664 A CN 105062664A CN 201510439314 A CN201510439314 A CN 201510439314A CN 105062664 A CN105062664 A CN 105062664A
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- ether
- oleic acid
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- methyl alcohol
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- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 title claims abstract description 31
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 title claims abstract description 31
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 title claims abstract description 31
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 239000005642 Oleic acid Substances 0.000 title claims abstract description 31
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 title claims abstract description 31
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 23
- 241000239370 Euphausia superba Species 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 102
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 78
- 239000012259 ether extract Substances 0.000 claims abstract description 23
- 238000000605 extraction Methods 0.000 claims abstract description 21
- 238000002425 crystallisation Methods 0.000 claims abstract description 20
- 230000008025 crystallization Effects 0.000 claims abstract description 19
- 238000010438 heat treatment Methods 0.000 claims abstract description 12
- 238000010992 reflux Methods 0.000 claims abstract description 12
- 241000239366 Euphausiacea Species 0.000 claims description 43
- 238000005238 degreasing Methods 0.000 claims description 34
- 239000007788 liquid Substances 0.000 claims description 7
- 230000004304 visual acuity Effects 0.000 claims description 5
- 238000001514 detection method Methods 0.000 abstract description 14
- 241000239368 Euphausia Species 0.000 abstract 3
- 235000021313 oleic acid Nutrition 0.000 description 26
- 229960002969 oleic acid Drugs 0.000 description 26
- 239000000706 filtrate Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 5
- 238000002390 rotary evaporation Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 239000013049 sediment Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 241001465754 Metazoa Species 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
- 230000000694 effects Effects 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000012795 verification Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YZAZXIUFBCPZGB-QZOPMXJLSA-N (z)-octadec-9-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O YZAZXIUFBCPZGB-QZOPMXJLSA-N 0.000 description 1
- 241000238421 Arthropoda Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229960005069 calcium Drugs 0.000 description 1
- 235000001465 calcium Nutrition 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229960004232 linoleic acid Drugs 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000001055 magnesium Nutrition 0.000 description 1
- 229940091250 magnesium supplement Drugs 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 235000008935 nutritious Nutrition 0.000 description 1
- 235000021315 omega 9 monounsaturated fatty acids Nutrition 0.000 description 1
- 230000021715 photosynthesis, light harvesting Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 235000007686 potassium Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
The invention discloses a method for preparing and detecting oleic acid in degreased euphausia superb. The method comprises the following steps of: (1) performing heating reflux extraction on the degreased euphausia superb by adopting methanol, and removing methanol to obtain paste; (2) extracting the paste in the step (1) by adopting ethyl ether, and removing ethyl ether in extraction liquor to obtain ethyl ether extract; (3) adding ethyl ether into the ethyl ether extract in the step (2), performing crystallization at the low temperature, centrifuging the liquor at the low temperature, and removing ethyl ether to obtain an orange red oily matter; and (4) performing mid-infrared absorptivity detection. The invention provides a method for extracting and detecting oleic acid in the degreased euphausia superb, the detection method is simple, quick, accurate, stable and reliable, and the yield can reach 8.82%.
Description
Technical field
The invention belongs to food and chemical field, be specifically related to a kind of method of preparation and detection oleic acid from degreasing krill.
Background technology
Krill (EuphausiasuperbaDana) has another name called large krill or Antarctic krill, is subordinate to Arthropoda, Crustachia, Euphausiacea, is maximum, procreation one of the most successful single Biological resources of quantity on the earth.Krill resource standing stock are huge, estimate in (6.5 ~ 10) × 10
8t is the one can enriched the most for standing stock in the marine animal resource of human use.Krill is nutritious, except being rich in albumen, also containing the necessary whole amino acid of human body, be rich in the multi mineral prime element such as the unsaturated fatty acids such as linolic acid, linolenic acid and calcium, potassium, magnesium, and carotenoid pigment content is high.Along with the problem sharply expanding, be short of food of population in the world becomes increasingly conspicuous, be badly in need of the Biological resources that exploitation is new.The huge resources bank that krill enriches as comprehensive nutrition, has wide exploitation prospect.
Oleic acid (Oleicacid) is a kind of cholesterol Omega-9 lipid acid, certain effectiveness is had to vessel softening, also play an important role in the metabolic processes of humans and animals, but the oleic acid of human body self synthesis can not be satisfied the demand, will absorb from food, therefore the higher edible oil of oleic acid content is good for health.
Not yet have the report about extracting preparation and detection oleic acid from degreasing krill at present, therefore, develop the method for isolation and determination oleic acid in a kind of degreasing krill, the exploitation tool for krill resource is of great significance.
Summary of the invention
The object of this invention is to provide a kind of method of preparation and detection oleic acid from degreasing krill.
The technical solution used in the present invention is:
From degreasing krill, prepare a method for oleic acid, comprise the following steps:
(1) degreasing krill is adopted methyl alcohol heating and refluxing extraction, the mass volume ratio of described degreasing krill and methyl alcohol is 1g:(6 ~ 10) mL, removing methyl alcohol, obtains paste;
(2) paste in step (1) adopts ether lixiviate, and the mass volume ratio of described paste and ether is 1g:(6 ~ 10) mL, vat liquor removing ether, obtains ether extract;
(3) step (2) gained ether extract, add ether crystallization at 4 ~ 8 DEG C again, described ether extract and ether mass volume ratio are 1g:(2 ~ 4) mL, the liquid cryogen after crystallization is centrifugal, obtains orange red oily matter after removing ether.
From degreasing krill, detect a method for oleic acid, comprise the following steps:
(1) degreasing krill is adopted methyl alcohol heating and refluxing extraction, the mass volume ratio of described degreasing krill and methyl alcohol is 1g:(6 ~ 10) mL, removing methyl alcohol, obtains paste;
(2) paste in step (1) adopts ether lixiviate, and the mass volume ratio of described paste and ether is 1g:(6 ~ 10) mL, vat liquor removing ether, obtains ether extract;
(3) step (2) gained ether extract, add ether again 4 ~ 8 DEG C of crystallizations, described ether extract and ether mass volume ratio are 1g:(2 ~ 4) mL, the liquid cryogen after crystallization is centrifugal, obtains orange red oily matter after removing ether.
(4) oily matter of gained in step (3) is done middle infrared absorbency to detect.
In step (1), described degreasing krill adopts hydrophobic solvent except degrease, and described hydrophobic solvent is normal hexane, vegetables oil extractant or sherwood oil.
In step (1), preferably, the mass volume ratio of described degreasing krill and methyl alcohol is 1g:6mL, adopts methyl alcohol heating and refluxing extraction 2 ~ 5 times, and be preferably 3 times, Extracting temperature is 70-80 DEG C, and extraction time is 60min.
Adopt the oleic acid that methyl alcohol heating and refluxing extraction is not only effectively isolated in degreasing krill for 2 ~ 5 times, the energy dissipation that the increase that can also as far as possible reduce extraction time brings.
In step (1), the water content of described degreasing krill is 7 ~ 8%.
In step (2), preferably, the mass volume ratio of described paste and ether is 1g:8mL.
Through experimental verification and analysis, when the mass volume ratio of described paste and ether is 1g:8mL, extracting effect is best, and ratio is comparatively large, and extracting effect is undesirable; Ratio is less, not only contaminate environment but also waste ether.
In step (3), preferably, described crystallization condition is: ether extract and ether mass volume ratio are 1g:3mL, Tc 8 DEG C, time 18 ~ 36h.
Add the reason of ether: one be ether easily volatilize in case with object product separation; Two is that ether easily makes solution supersaturation, is easier to the process of crystallization.Through experimental verification, when Tc 8 DEG C, time are 24h, must be able to be separated better for impurity.
In step (3), described centrifugal condition is 4 DEG C, 6000 ~ 8000r/min, time 10 ~ 30min, and the preferred time is 15min.
In step (4), described middle infrared absorbency (MIR-ATR) testing conditions is resolving power 4cm
-1, sweep time 16s, mid-infrared light source, KBr beam splitter.
The invention has the beneficial effects as follows:
The present invention provides the preparation and determination methods method of degreasing krill oleic acid first, and detection method is simple, quick, accurate, stable, reliable, can reach 8.82% through calculating oleic acid yield.
The preparation and determination methods method of oleic acid in degreasing krill of the present invention, simple to operate, cost is low.
The present invention makes krill use value obtain further exploitation, and thinking has been widened in the exploitation for Biological resources, has broad application prospects.
Accompanying drawing explanation
The infared spectrum of oleic acid in Fig. 1: Bruker infrared picture library.
Fig. 2: the infrared figure of embodiment 1 sample.
Fig. 3: the infrared figure of embodiment 2 sample.
Fig. 4: the infrared figure of embodiment 3 sample.
Embodiment
Embodiment 1
A method for preparation and detection oleic acid from degreasing krill, comprises the following steps:
The dry krill 100g of degreasing, adds methyl alcohol 600mL, heating and refluxing extraction 5 times in 70 DEG C of water-baths, filters after each extraction 60min.Merging filtrate, rotary evaporation removing methyl alcohol obtains paste 60g.In paste, add 360mL ether, stirring and dissolving, sediment obtains filtrate, and evaporation removing ether obtains ether extract 15.1g.
Get 1.93g ether extract, add 4mL ether, put into 8 DEG C of refrigerator crystallizations, time 18h.After crystallization, liquid is carried out low-temperature and high-speed centrifugal, centrifugal condition is 4 DEG C, 8000r/min, time 10min, obtains orange red oily matter after volatilizing ether.Get an oily matter and do MIR-ATR detection, detecting this material is oleic acid, and (Fig. 1 is oleic acid infared spectrum in Bruker picture library as shown in the figure; Fig. 2 is the infrared figure of embodiment 1 sample).MIR-ATR testing conditions is resolving power 4cm
-1, sweep time 16s, mid-infrared light source, KBr beam splitter.
Claim orange red oily matter quality is 1.11g.The dry krill of 100g degreasing can be obtained as calculated and prepare oleic acid 8.68g.
Embodiment 2
The dry krill 100g of degreasing, adds methyl alcohol 800mL, heating and refluxing extraction 5 times in 75 DEG C of water-baths, and each extraction is filtered for 60 minutes afterwards.Merging filtrate, rotary evaporation removing methyl alcohol obtains paste 60.9g.Add 488mL ether to paste, obtain ether extract 15.3g.Get 1.97g ether extract, add 6mL ether, put into 8 DEG C of refrigerator crystallizations, time 24h.After crystallization, liquid is centrifugal through low-temperature and high-speed, centrifugal condition is 4 DEG C, 8000r/min, time 15min, obtains orange red oily matter after volatilizing ether.Get an oily matter and do MIR-ATR detection, analyzing this material is oleic acid, as shown in Figure 2.MIR-ATR testing conditions is resolving power 4cm
-1, sweep time 16s, mid-infrared light source, KBr beam splitter.
Claim orange red oily matter quality is 1.12g.Obtain the dry krill of 100g degreasing as calculated and prepare oleic acid 8.70g.
Embodiment 3
The dry krill 100g of degreasing, adds methyl alcohol 1000mL, heating and refluxing extraction 2 times in 80 DEG C of water-baths, and each extraction is filtered for 60 minutes afterwards.Merging filtrate, rotary evaporation removing methyl alcohol obtains paste 61g.Add 660mL ether to paste, obtain ether extract 15.3g.Get 1.96g ether extract, add 8mL ether, put into 6 DEG C of refrigerator crystallizations, time 36h.Post-crystallization liquor is centrifugal through low-temperature and high-speed, and described centrifugal condition is 4 DEG C, 8000r/min, time 30min, obtains orange red oily matter after volatilizing ether.Get an oily matter and do MIR-ATR detection, detecting this material is oleic acid, as shown in Figure 3.MIR-ATR testing conditions is resolving power 4cm
-1, sweep time 16s, mid-infrared light source, KBr beam splitter.
Claim orange red oily matter quality is 1.13g.Obtain the dry krill of 100g degreasing as calculated and prepare oleic acid 8.82g.
Embodiment 4
The dry krill 100g of degreasing, adds methyl alcohol 600mL, heating and refluxing extraction 5 times in 80 DEG C of water-baths, and each extraction is filtered for 60 minutes afterwards.Merging filtrate, rotary evaporation removing methyl alcohol obtains paste 61g.In paste, add 363mL ether, stirring and dissolving, sediment obtains filtrate, and evaporation removing ether obtains ether extract 15.2g.
Get 2g ether extract, add 6mL ether, put into 4 DEG C of refrigerator crystallizations, time 24h.After crystallization, liquid is carried out low-temperature and high-speed centrifugal, described centrifugal condition is 4 DEG C, 6000r/min, time 15min, obtains orange red oily matter after volatilizing ether.Claim to obtain orange red oily matter.Get an oily matter and do MIR-ATR detection, detecting this material is oleic acid, and testing conditions is with embodiment 1.
Claim orange red oily matter quality is 1.15g.The dry krill of 100g degreasing can be obtained as calculated and prepare oleic acid 8.74g.
Embodiment 5
The dry krill 100g of degreasing, adds methyl alcohol 600mL, heating and refluxing extraction 3 times in 80 DEG C of water-baths, and each extraction is filtered for 60 minutes afterwards.Merging filtrate, rotary evaporation removing methyl alcohol obtains paste 60.6g.In paste, add 606mL ether, stirring and dissolving, sediment obtains filtrate, and evaporation removing ether obtains ether extract 15.3g.
Get 2g ether extract, add 6mL ether, put into 8 DEG C of refrigerator crystallizations, time 24h.After crystallization, liquid is carried out low-temperature and high-speed centrifugal, described centrifugal condition is 4 DEG C, 7000r/min, time 15min, obtains orange red oily matter after volatilizing ether.Get an oily matter and do MIR-ATR detection, analyzing this material is oleic acid, and detection method is with embodiment 1.
Claim orange red oily matter quality is 1.15g.The dry krill of 100g degreasing can be obtained as calculated and prepare oleic acid 8.80g.
The dry krill of degreasing described in embodiment 1 ~ 5, its water content is 7 ~ 8%.
Claims (6)
1. from degreasing krill, prepare a method for oleic acid, it is characterized in that, comprise the following steps:
(1) degreasing krill is adopted methyl alcohol heating and refluxing extraction, the mass volume ratio of described degreasing krill and methyl alcohol is 1g:(6 ~ 10) mL, removing methyl alcohol, obtains paste;
(2) paste in step (1) adopts ether lixiviate, and the mass volume ratio of described paste and ether is 1g:(6 ~ 10) mL, vat liquor removing ether, obtains ether extract;
(3) step (2) gained ether extract, add ether crystallization at 4 ~ 8 DEG C again, described ether extract and ether mass volume ratio are 1g:(2 ~ 4) mL, the liquid cryogen after crystallization is centrifugal, obtains orange red oily matter after removing ether.
2. the method for claim 1, is characterized in that: in step (1), and the mass volume ratio of described degreasing krill and methyl alcohol is 1g:6mL, and adopt methyl alcohol heating and refluxing extraction 2 ~ 5 times, Extracting temperature is 70-80 DEG C, and extraction time is 60min.
3. the method for claim 1, is characterized in that: in step (2), and the mass volume ratio of described paste and ether is 1g:8mL.
4. the method for claim 1, is characterized in that: in step (3), described crystallization condition is: ether extract and ether mass volume ratio are 1g:3mL, Tc 8 DEG C, time 24h.
5. the method for claim 1, is characterized in that: in step (3), and described centrifugal condition is 4 DEG C, 6000 ~ 8000r/min, time 10 ~ 30min.
6. from degreasing krill, detect a method for oleic acid, it is characterized in that, comprise the following steps:
S1: adopt the arbitrary described method of Claims 1 to 5 to prepare orange red oily matter;
S2: the oily matter of gained in step S1 is done middle infrared absorbency and detect, described middle infrared absorbency testing conditions is: resolving power 4cm
-1, sweep time 16s, mid-infrared light source, KBr beam splitter.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3504309A4 (en) * | 2016-08-24 | 2020-07-29 | Samuel Philip | Improved method for processing and extracting oil from marine organisms |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3504309A4 (en) * | 2016-08-24 | 2020-07-29 | Samuel Philip | Improved method for processing and extracting oil from marine organisms |
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