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CN103773596A - Preparation method of krill oil - Google Patents

Preparation method of krill oil Download PDF

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Publication number
CN103773596A
CN103773596A CN201310754432.7A CN201310754432A CN103773596A CN 103773596 A CN103773596 A CN 103773596A CN 201310754432 A CN201310754432 A CN 201310754432A CN 103773596 A CN103773596 A CN 103773596A
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krill
alcohol
preparation
extraction agent
time
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CN103773596B (en
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陆文达
陈永
陈光华
李剑英
郑卫琴
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Jiucong (Shanghai) Biotechnology Co., Ltd
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SHANGHAI FULI BIO-PHARMACEUTICAL Co Ltd
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Abstract

The invention discloses a preparation method of krill oil. The preparation method comprises the following steps of (1) uniformly mixing krill and an extracting agent, and cutting the mixture, wherein one liter of extracting agent is added into every 0.5kg to 1.5kg of krill; (2) separating solid from liquid to obtain krill paste; (3) uniformly mixing the krill paste with the extracting agent, extracting the krill paste to obtain extracting liquid, and removing solvent, wherein 1 to 2 liters of extracting agent are added into every 1kg of krill, and the extracting agent is C2-4 alcohol or C2-4 alcohol aqueous solution. Due to the adoption of the preparation method, the existing conventional dehydration process is not needed, the preparation method is simple, the prepared krill oil is good in mobility, high in transparency and less in soluble impurity, the content of phospholipid is more than 40 percent, and the content of phosphatidylcholine in the phospholipid is more than 60 percent.

Description

The preparation method of krill oil
Technical field
The present invention relates to a kind of preparation method of krill oil.
Background technology
Krill is the krill of one way of life in waters, the Antarctica, is also the most ripe single one of Biological resources of planting of quantity maximum on the earth.The krill oil extracting from krill is rich in the compositions such as phosphatide (mainly take Yelkin TTS as main), and the lipid acid of phosphatide mainly comprises timnodonic acid (EPA) and docosahexenoic acid (DHA), and the content sum of the two accounts for the more than 40% of fatty acids in phospholipids total amount.Antarctic krill oil has the cardiovascular disorder of reduction, prevention senile dementia and improves the multiple physiologically active such as immunity of organisms, and its activity is better than the lecithin product (in its lipid acid composition containing EPA and DHA) in triglyceride type EPA/DHA product in the market and terrestrial plant source.
Unsaturated fatty acids docosahexenoic acid (DHA) is mainly combined on glyceryl 2 (Sn2 positions) of phosphatide, DHA is the basis that forms brain cell membrane, the g and D of division to brain cell, propagation, nerve conduction, cynapse plays a part very important, is the essential material that human brain forms and IQ is developed.And DHA is on vision, brain activity, metabolism of fat, fetal growth and immunologic function and avoid senile dementia to have very big impact.DHA when shortage, can cause series of symptoms, comprises growth retardation, the skin abnormality scales of skin that peel off, sterile, dysnoesia etc.
But common DHA arranges in random mode, in unordered state, cannot guarantee to be absorbed by the body completely, the DHA on Sn1, Sn3 position is digested in human body conventionally, produces heat, only has the DHA on Sn2 position to be absorbed completely by human body.In krill oil, DHA is combined on the glyceryl Sn2 position of phosphatide, therefore can be absorbed by people completely, and biological activity and the bioavailability of the DHA on the Sn2 position of krill are very high, is 3-5 times of common fish oil DHA activity.
By krill oil be simultaneously raw material by the way of biological enzyme, can change into phosphatidylserine (PS).The function of phosphatidylserine (PS) is mainly to improve neurocyte function, regulates the conduction of Nerve impulse, promotes brain memory function.Relevant expert generally acknowledges: be attached to phosphatidylserine (PS) from unsaturated fatty acids two dodecahexaenes (DHA) in krill oil source, the two comprehensive action, can improve brain neuroblastoma cell function and brain activity, improve memory and promote infant's brain grow and safeguard brain health, there is great economy and theory value.
Based on the critical role of krill resource, countries in the world are all using krill as important food resource, and start expedition krill in the phase at the beginning of the sixties in last century.Produce so far, krill total catch has exceeded 6,000,000 tons.But at present, the krill that fish for countries in the world is processed to the feed of aquaculture mostly, and its economic worth and social value find full expression far away.Under the realistic background sharp rising in energy prices and labor cost etc., make full use of the krill oil resource in krill, exploitation high value added product, is the important channel that krill utilizes.
Enter after 21st century, the krill oil demand rapid growth of market to medical-grade, krill industry has been caught this opportunity.Owing to containing abundant phosphatide in krill oil, attract showing great attention to of dietary supplements industries.The fast development of krill health-product market and other marine organism health care product have formed day by day fierce market competition simultaneously.The Aker Biomarine company of Norway and Canadian Neptune Technologies company are the main medical-grade krill oil manufacturing enterprises in the whole world at present.Particularly Aker Biomarine company, the enterprise that sea-food of Qi Shi Norway is fished for and processed, research and development, the production and selling of being engaged in high-end krill product are existing for many years, and only 2009, the krill oil healthcare products of 100 tons of left and right were just sold by company.
Domesticly be engaged in the recent period krill oil research and development and production unit gets more and more.The extracting method of krill oil is in the past that hot-pressing method fork-like farm tool used in ancient China extracts, but this method yield is low, and service temperature is high, and quality product is had to impact, is eliminated gradually.In prior art, generally adopt take dry krill meal (moisture 8%-10%) as raw material, extract krill oil with solvent method, but the method also has certain defect, the first, krill meal has strict requirement for water content, general requirement water content is at 8%-10%, can have a great impact extraction yield because water content is too high, and can make a large amount of harmful water solubility impurities can enter in extracting solution, increase aftertreatment cleaning section difficulty; The second, krill body contains a kind of enzyme, after fishing for, can be rapidly protein digestion in krill in conventional lower a few hours of temperature, become toxic substance, be commonly called as the self-dissolving into krill, the krill after self-dissolving can not human consumption, therefore the preparation of krill meal is generally to carry out on dredger, but dredger space is little, and treatment capacity is limited, add market large for the demand of krill meal, there is the phenomenon that supply falls short of demand in krill meal, expensive.
On the other hand, on dredger, can also krill is freezing to below-20 ℃, to freeze shrimp form storage and transport rapidly.In prior art, it is that raw material directly extracts krill oil that people also attempt freezing shrimp.Extracting method is generally first to remove moisture, then extracts krill oil.The method of removing moisture generally adopts the dehydration of low-temperature frozen dry method fork-like farm tool used in ancient China, the method service temperature low (30 degree are following), and dewatering time is long, and cost is higher.Another kind of dewatering is thermal dehydration under vacuum, the method power consumption is large, and because phosphatide in krill oil is heat-sensitive substance, temperature is high can decompose in a large number, make the dehydration temperaturre can not be too high, thereby make dewatering time become very long, generally need 7-8 hour, be not suitable for large-scale industrial production.
And, obtain after krill oil in extraction, the process such as also need to refine, remove the impurity in krill oil.In a word, the extracting method extraction process step complexity of krill oil in prior art, composition is very high.This phenomenon has increased the making composition of phosphatide, urgently to be resolved hurrily.Therefore, develop-kind directly take freezing krill as raw material, and preparation technology is simple, and the method that time consumption and energy consumption is few, extracts krill oil, is very urgent.
Summary of the invention
Technical problem to be solved by this invention is to overcome in prior art that extract the method for krill oil take krill meal as raw material large to the demand of krill meal, raw material supply is inadequate, be that raw material extraction krill oil preparation time is long and adopt freezing krill, the defect that energy consumption is large, a kind of preparation method of krill oil is provided, described preparation method does not need the dehydration through existing routine, preparation method is simple, the krill oil good fluidity making, transparency is high, water-soluble impurity is (as polysaccharide, the materials such as low molecular polypeptide) few, extraction yield obviously improves, phospholipids content is more than 40%, in phosphatide, lecithin content is more than 60%.
In prior art, in the extracting method of krill oil, the dewatering dewatering time of krill is long, and cost is higher.On this basis, contriver removes moisture by the extraction agent that adds certain concentration in krill.But great many of experiments shows: extraction agent removes for moisture in krill, and not as easy in the imagination.In great many of experiments, the extraction yield of krill oil is almost 0, that is to say: simple extraction agent, cannot extract and obtain krill oil at all.Its former because: ethanol can extract moisture and phosphatide simultaneously, but the present invention but needs by moisture and phosphatide separately, to obtain target extract---phosphatide, and, in the time that first moisture can not be removed, cannot extract and obtain phosphatide.This is also in prior art, still not use C 2-4alcohol remove the reason of moisture in krill.
But contriver is through further research, find: the extraction agent of specific consumption, coordinate again specific processing step and condition, not only can remove the moisture in krill, and can not cause the loss of phosphatide, on this basis, can also remove the impurity in krill oil, thus, not need just can obtain through treating process the krill oil that purity is high, the extraction yield of krill oil is also improved, and has realized the effect of achieving many things at one stroke.So far, just obtained technical scheme of the present invention.
The object of the invention is to: a kind of preparation method of krill oil is provided, and described preparation method comprises the following steps:
(1) krill is mixed with extraction agent, obtain mixture A, shear; Described extraction agent is C 2-4alcohol or C 2-4the aqueous solution of alcohol, in the krill that the addition of described extraction agent is every 0.5-1.5kg, add the extraction agent of 1L;
(2) solid-liquid separation, obtains shrimp mud;
(3) described shrimp mud is mixed with extraction agent, obtain mixture B, extract, obtain extracting solution, desolvation; Described extraction agent is C 2-4alcohol or C 2-4the aqueous solution of alcohol, in the krill that the addition of described extraction agent is every 1kg, add the extraction agent of 1-2L.
Be described further for above-mentioned preparation method below:
In step (1), before described krill is mixed with extract, preferably described krill is carried out to certain pre-treatment; Described pretreated method is the method for this area routine, as cleaned, drains etc.The described method draining is the method for this area routine, preferably for naturally draining.
Those skilled in the art all understand: because krill self-dissolving is at normal temperatures rapid, quality changes very fast, generally speaking needs freezing storage; In the time that described krill is freezing krill, preferably needs krill to thaw, then drain.The described method of thawing is the method for this area routine, is preferably under 10-20 ℃ of condition, and described freezing krill is mixed with water, soak.The described time of thawing is the time of this area routine, is preferably in 30min; The consumption of described water is the consumption of this area routine, preferably for not having described freezing krill.The method that immersion is thawed is naturally thawed in air than by krill or is heated thaw effective.After described thawing, after preferably described krill being cleaned, then drain.Generally speaking, described thaws to the process draining, and can remove a large amount of water-soluble impurity on krill surface, as NaCl, thereby reduces the foreign matter content in finished product.
In the present invention, described alcohol is preferably C 2-3alcohol, be more preferably one or more in ethanol, n-propyl alcohol and Virahol.
In step (1), the addition of described extraction agent is preferably for adding the extraction agent of 1L in the krill of every 1kg.
In step (1), after described mixing, the content of the alcohol in described mixture A is preferably 40%-80%, is more preferably 50%-70%; Described per-cent is the volume percent that described alcohol accounts for the liquid in described mixture A.
In step (1), after mixing, krill fully contacts with extraction agent, in krill, large quantity of moisture discharges, and Extractant concentration further reduces, under this concentration, krill oil can not be leached, and impurity (as polysaccharide, low molecular polypeptide etc.) in shrimp can be leached.This step has not only removed the moisture in krill, for the extraction of follow-up krill is laid a good foundation, can remove the impurity in krill simultaneously, extract after krill oil without carrying out again loaded down with trivial details treating process consuming time.
In step (1), the concentration of the aqueous solution of described alcohol is preferably more than 90%, is more preferably 95%, and described per-cent is the volume percent that described alcohol accounts for the aqueous solution of alcohol.
In step (1), preferably, before described shearing, described krill and described extraction agent are stirred, and tentatively pulverize.The method of described pulverizing is preferably for being used toothed gear pump to pulverize.
In step (1), preferably, the method for described shearing and condition are method and the condition of this area routine.The speed of described shearing is preferably 5000-12000rpm, is more preferably 10000rmp.The time of described shearing is preferably 5-15min, is more preferably 10min.Described shearing is preferably carried out in high-speed shearing machine.
In step (2), the method for described solid-liquid separation and condition are method and the condition of this area routine.The method of described solid-liquid separation is preferably centrifugation; The separating factor (ratio of centrifugal force and gravity) of described whizzer, preferably for being greater than 2500G, is more preferably 2500-3000G.The residence time of described centrifugation is preferably 10-20min, is more preferably 15min.Described centrifugation is preferably for being used desk centrifuge or horizontal screw centrifuge centrifugal.
In step (2), preferably, the fluent meterial containing alcohol that described solid-liquid separation obtains can reclaim according to the recovery method of the alcohols material of this area routine; Described recovery method is preferably distillation; Described distillation preferably for to adopt tower equipment to carry out under normal pressure.
In step (3), the addition of described extraction agent is preferably the extraction agent that adds 1L in the krill of every 1kg.
In step (3), after described mixing, the content of the alcohol in described mixture B is preferably 90%-95%, and described per-cent is the volume percent that described alcohol accounts for the liquid in described mixture B.
In step (3), described extraction is preferably extracted for stirring.The time of described extraction is preferably 20-40min, is more preferably 30min.
In step (3), preferably, the number of times of described extraction is the number of times of this area routine, and the number of times of described extraction is preferably 2-3 time.In the time that described extraction time is greater than 1 time, according to this area routine, united extraction liquid.
In step (3), the method for described desolvation and condition are method and the condition of this area routine; The method of described desolvation is preferably vacuum removal solvent under the temperature condition below 60 ℃.The described temperature of deviating from solvent is preferably 40-55 ℃.The time of described desolvation is preferably 10-30min.Described desolvation preferably successively water-ring vacuum pump take out with rubbing board oil-sealed rotary pump in carry out, or carry out in revolution rubbing board vaporizer.
Meeting on the basis of this area general knowledge, above-mentioned each optimum condition, can arbitrary combination, obtains the preferred embodiments of the invention.
Agents useful for same of the present invention and raw material be commercially available obtaining all.
Positive progressive effect of the present invention is: the extracting method preparation method of krill oil of the present invention is simple, the krill oil good fluidity, the transparency that make are high, water-soluble impurity (as the material such as polysaccharide, low molecular polypeptide) is few, extraction yield obviously improves, phospholipids content is more than 40%, and in phosphatide, lecithin content is more than 60%.
Embodiment
Mode below by embodiment further illustrates the present invention, but does not therefore limit the present invention among described scope of embodiments.The experimental technique of unreceipted actual conditions in the following example, according to ordinary method and condition, or selects according to catalogue.
Embodiment 1
(1) hydrostatic thaws: get the freezing krill of 190g, be added to containing in water-soluble device, under 18 ℃ of conditions of water temperature, hydrostatic soaks after 15min, freezes shrimp and melts, and now water temperature is reduced to 12 ℃ of left and right; Use funnel drain well, use again if desired a small amount of 4~6 ℃ of pure water drip washing, except the NaCl of deentrainment;
(2) 95% ethanol of 200mL and the shrimp body draining are mixed, obtain mixed liquor A, in mixed liquor A, the content of ethanol is the volume percent that 60%(ethanol accounts for the liquid in mixture A), pulverize, join high-shear machine and shear 10min at 10000rpm;
(3) with desk centrifuge centrifugal 15min under 3000G centrifugal force, obtain shrimp mud;
(4) to 95% ethanol that adds 200mL in shrimp mud, mix, obtain mixture B, in mixture B, the content of ethanol is the volume percent that 90%(ethanol accounts for the liquid in mixture B), stir 30min, static layering, elimination ethanol phase; Add again the dehydrated alcohol of 200mL, repeat to extract, merge secondary raffinate; At 60 ℃, in glass revolution vaporizer, vacuumize with water-ring vacuum pump, slough ethanol, then use rubbing board oil-sealed rotary pump, under high vacuum condition, continue to remove residual ethanol and micro-moisture (10 points of kinds).
The product making is reddish brown, can flow, and this product energy encapsulating ball, capsule and pill inclusion is not aobvious muddy, illustrates that the product making is transparence, and Product Status is good.
Recording phospholipids content in krill oil product with molybdenum blue colorimetric method is 41%, lecithin content 70% in phosphatide.
Embodiment 2
(1) hydrostatic thaws: get the freezing krill of 400g, be added to containing in water-soluble device, under 20 ℃ of conditions of water temperature, hydrostatic soaks 15min, freezes shrimp and melts; Use funnel drain well, use again if desired a small amount of 4~6 ℃ of pure water drip washing;
(2) Virahol of 500mL is joined to above-mentioned thawing in the shrimp body draining, fully mix, obtain mixed liquor A, in mixed liquor A, the content of Virahol is the volume percent that 70%(Virahol accounts for the liquid in mixture A), pulverize, and join high-shear machine at 10000rpm down cut 10min;
(3) with desk centrifuge, centrifugal 15min under 3000G centrifugal force, obtains shrimp mud;
(4) to the Virahol that adds 500mL in shrimp mud, mix, obtain mixture B, in mixture B, the content of Virahol is the volume percent that 90%(Virahol accounts for the liquid in mixture B), stir 30min, static layering, elimination Virahol phase; Add again the Virahol of 500mL, repeat to extract, merge secondary raffinate, at 60 ℃, in glass revolution vaporizer, vacuumize de-Virahol with water-ring vacuum pump, vacuumize with rubbing board oil-sealed rotary pump again, under high vacuum condition, continue to remove residual Virahol and de-micro-moisture (15min).
The product making is reddish brown, can flow, and this product energy encapsulating ball, capsule and pill inclusion is not aobvious muddy, illustrates that the product making is transparence, and Product Status is good.
Recording phospholipids content in krill oil product with molybdenum blue colorimetric method is 43%, lecithin content 65% in phosphatide.
Embodiment 3
(1) hydrostatic thaws: get 500 kilograms of freezing krills, join 1500 liters of stainless steels and extract in narrow-necked earthen jar, after topped up with water, the static 20min that thaws under 15 ℃ of conditions of water temperature, freezes shrimp and melt; Emit immersion water from narrow-necked earthen jar bottom, then with the pure water drip washing of 100 liters 4~6 ℃ and drain;
(2) 500 liter of 95% ethanol being joined to above-mentioned stainless steel extracts in narrow-necked earthen jar, mix, obtain mixed liquor A, in mixed liquor A, the content of ethanol is the volume percent that 70%(ethanol accounts for the liquid in mixture A), play circulation with toothed gear pump, make two-phase fully be uniformly mixed pulverizing, then insert high-shear machine from top, 15min turns round under 10000rpm;
(3) start horizontal screw centrifuge, the material in toothed gear pump is joined in horizontal screw centrifuge entrance, flow out respectively ethanol and the very low shrimp mud of water capacity at two ends of whizzer;
(4) shrimp mud being joined together with 500 liters of dehydrated alcohols to stainless steel extracts in narrow-necked earthen jar, mix, obtain mixture B, in mixture B, the content of ethanol is the volume percent that 90%(ethanol accounts for the liquid in mixture B) stir 30min leach, static layering, elimination alcohol phase; Add 500 liters of dehydrated alcohols again, repeat to extract, united extraction liquid removes ethanol with turning round rubbing board vaporizer under vacuum condition.In process, with the heating of low-pressure steam chuck, collect from the liquid krill of the oily of revolution rubbing board base of evaporator exit outflow; ; After filter residue in stainless steel narrow-necked earthen jar is taken out, with the de-ethanol of 80 ℃ of warm airs, the dry-matter after precipitation completes can be used as feed and uses.
The product making is reddish brown, can flow, and this product energy encapsulating ball, capsule and pill inclusion is not aobvious muddy, illustrates that the product making is transparence, and Product Status is good.
The phospholipids content recording with molybdenum blue colorimetric method is 40.5%, and in phosphatide, lecithin content is more than 70%.

Claims (10)

1. a preparation method for krill oil, is characterized in that: described preparation method comprises the following steps:
(1) krill is mixed with extraction agent, obtain mixture A, shear; Described extraction agent is C 2-4alcohol or C 2-4the aqueous solution of alcohol, in the krill that the addition of described extraction agent is every 0.5-1.5kg, add the extraction agent of 1L;
(2) solid-liquid separation, obtains shrimp mud;
(3) described shrimp mud is mixed with extraction agent, obtain mixture B, extract, obtain extracting solution, desolvation; Described extraction agent is C 2-4alcohol or C 2-4the aqueous solution of alcohol, in the krill that the addition of described extraction agent is every 1kg, add the extraction agent of 1-2L.
2. preparation method as claimed in claim 1, is characterized in that: described alcohol is C 2-3alcohol, be preferably one or more in ethanol, n-propyl alcohol and Virahol.
3. preparation method as claimed in claim 1, is characterized in that: in step (1), add the extraction agent of 1L in the krill that the addition of described extraction agent is every 1kg;
In step (1), after described mixing, the content of the alcohol in described mixture A is preferably 40%-80%, is more preferably 50%-70%; Described per-cent is the volume percent that described alcohol accounts for the liquid in described mixture A;
In step (3), the shrimp mud that the addition of described extraction agent is every 1kg adds the extraction agent of 1L;
In step (3), after described mixing, the content of the alcohol in described mixture B is preferably 90%-95%, and described per-cent is the volume percent that described alcohol accounts for the liquid in described mixture B.
4. preparation method as claimed in claim 1, is characterized in that: in step (1), the speed of described shearing is 5000-12000rpm, is preferably 10000rmp; The time of described shearing is 5-15min, is preferably 10min; Described shearing is preferably carried out in high-speed shearing machine.
5. preparation method as claimed in claim 1, is characterized in that: in step (2), the method for described solid-liquid separation is centrifugation; The separating factor of described centrifugation, preferably for being greater than 2500G, is more preferably 2500-3000G; The time of described centrifugation is preferably 10-20min, is more preferably 15min; Described centrifugation is preferably for being used desk centrifuge or horizontal screw centrifuge centrifugal.
6. preparation method as claimed in claim 1, is characterized in that: in step (3), the method for described desolvation is vacuum removal solvent under the temperature condition below 60 ℃; The described temperature of deviating from solvent is preferably 40-55 ℃; The time of described desolvation is preferably 10-30min.
7. the preparation method as described in claim 1-6 any one, is characterized in that:
In step (1), the concentration of the aqueous solution of described alcohol is more than 90%, is preferably 95%, and described per-cent is the volume percent that described alcohol accounts for the aqueous solution of alcohol.
8. the preparation method as described in claim 1-6 any one, is characterized in that:
In step (1), before described krill is mixed with extract, described krill is carried out to pre-treatment; Described pre-treatment is preferably for cleaning and draining; Described drains preferably for naturally draining;
In the time that described krill is freezing krill, preferably krill is thawed, then drain; The described method of thawing is: under 10-20 ℃ of condition, described freezing krill mixed with water, soaks; The described time of thawing is in 30min; The consumption of described water is not have described freezing krill; After described thawing, after described krill is cleaned, then drain.
9. the preparation method as described in claim 1-6 any one, is characterized in that: in step (1), before described shearing, described krill and described extraction agent are stirred, and pulverize; The method of described pulverizing is preferably for being used toothed gear pump to pulverize.
10. the preparation method as described in claim 1-6 any one, is characterized in that:
In step (3), described being extracted as stirred and extracted; The time of described extraction is preferably 20-40min, is more preferably 30min;
In step (3), the number of times of described extraction is the number of times of this area routine, and the number of times of described extraction is preferably 2-3 time; In the time that described extraction time is greater than 1 time, united extraction liquid.
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CN103981021A (en) * 2014-05-31 2014-08-13 山东乾清翔泰生物制品有限公司 Method for refining krill oil from Antarctic krill powder
US20180133263A1 (en) * 2014-01-10 2018-05-17 Aker Biomarine Antarctic As Phospholipid compositions and their preparation
US10456412B2 (en) 2015-02-11 2019-10-29 Aker Biomarine Antarctic As Lipid extraction processes

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CN101652462A (en) * 2006-11-16 2010-02-17 普罗诺瓦生物医药挪威公司 Process for production of omega-3 rich marine phospholipids from krill
CN102899165A (en) * 2012-10-25 2013-01-30 山东师范大学 Technology for extracting bright red shrimp oil crude product from euphausia superba

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Publication number Priority date Publication date Assignee Title
US4219470A (en) * 1978-10-23 1980-08-26 Dravo Corporation Process for preparing a protein concentrate and the product obtained thereby
CN1269940C (en) * 1998-10-21 2006-08-16 舍布鲁克大学 Method for extracting lipid from marine and aquatic animal tissues
EP1331972A2 (en) * 2000-09-11 2003-08-06 Novartis AG Pharmaceutical compositions
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20180133263A1 (en) * 2014-01-10 2018-05-17 Aker Biomarine Antarctic As Phospholipid compositions and their preparation
CN103981021A (en) * 2014-05-31 2014-08-13 山东乾清翔泰生物制品有限公司 Method for refining krill oil from Antarctic krill powder
US10456412B2 (en) 2015-02-11 2019-10-29 Aker Biomarine Antarctic As Lipid extraction processes

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