WO2010035750A1 - 脂質の製造方法 - Google Patents
脂質の製造方法 Download PDFInfo
- Publication number
- WO2010035750A1 WO2010035750A1 PCT/JP2009/066530 JP2009066530W WO2010035750A1 WO 2010035750 A1 WO2010035750 A1 WO 2010035750A1 JP 2009066530 W JP2009066530 W JP 2009066530W WO 2010035750 A1 WO2010035750 A1 WO 2010035750A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- lipid
- water
- solid content
- krill
- washing
- Prior art date
Links
Images
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
- A23J7/00—Phosphatide compositions for foodstuffs, e.g. lecithin
-
- 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
- C11B13/00—Recovery of fats, fatty oils or fatty acids from waste materials
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
- A23J1/00—Obtaining protein compositions for foodstuffs; Bulk opening of eggs and separation of yolks from whites
- A23J1/04—Obtaining protein compositions for foodstuffs; Bulk opening of eggs and separation of yolks from whites from fish or other sea animals
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K10/00—Animal feeding-stuffs
- A23K10/20—Animal feeding-stuffs from material of animal origin
- A23K10/22—Animal feeding-stuffs from material of animal origin from fish
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/158—Fatty acids; Fats; Products containing oils or fats
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L17/00—Food-from-the-sea products; Fish products; Fish meal; Fish-egg substitutes; Preparation or treatment thereof
- A23L17/40—Shell-fish
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
- A61K35/56—Materials from animals other than mammals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
- A61K35/56—Materials from animals other than mammals
- A61K35/612—Crustaceans, e.g. crabs, lobsters, shrimps, krill or crayfish; Barnacles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C11B1/06—Production of fats or fatty oils from raw materials by pressing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/74—Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes
Definitions
- the present invention relates to a method for efficiently producing lipids contained in crustaceans, particularly phospholipids, and in particular, a method for producing them without causing malodor.
- Edible lipids have been industrially manufactured for a long time.
- soybean oil which is currently produced in the largest amount
- the raw soybean is washed, peeled off if necessary, crushed and compacted, and often extracted with an organic solvent such as hexane at about 50 to 60 ° C.
- the extract is then filtered and desolventized (often distilled) to obtain a crude oil.
- This crude oil is further filtered to remove the insoluble fraction by filtration or centrifugation, and water is added to remove water-soluble substances (degumming), followed by deoxidation, decolorization, and deodorization steps to obtain a product.
- Non-patent Document 1 In general, it is relatively easy to produce lipids from plant materials containing a high amount of lipids such as plant seeds (Non-patent Document 1).
- the oil components are separated by simply heating the raw materials after washing them, so that they can be manufactured more easily.
- fish oil is produced by refining it (Non-patent Document 2).
- the lipids obtained by these methods are mainly triglycerides.
- Phospholipids one of the lipids, are known to improve fatty liver derived from choline deficiency, reduce blood LDL (bad cholesterol), increase blood HDL (good cholesterol), and other health functions. Improvement of neuropathy resulting from hypertension and acetylcholine deficiency, and promotion of absorption of fat-soluble vitamins are expected.
- phospholipids are often separated and purified from soybean and chicken egg yolk. In the case of soybean, phospholipid is contained in the fraction removed as insoluble in the degumming step in the soybean oil production process, and this is decolorized and dried to obtain a phospholipid product called lecithin (Non-patent Document 3). ).
- Soybean oil is a very large market and phospholipids as a derivative can be obtained in large quantities.
- lipid In the case of chicken egg yolk, about one third of its weight is lipid, and about one third of the lipid is phospholipid, so that extraction and purification of phospholipid is relatively easy but efficient.
- it is necessary to remove water from the raw egg yolk in advance, and dry egg yolk is produced by adding heat costs, from which phospholipids are extracted.
- a method of extracting a lipid after drying the raw material in advance for example, a method of extracting a lipid after previously drying the raw material marine product to a moisture of 10% by weight or less (Patent Document 1)
- a method of extracting lipids after freeze-drying the raw material Patent Document 2
- a method using an organic solvent for example, extracting a lipid using a mixture of acetone and water for raw fish and shellfish
- Patent Document 3 a method of using acetone as a first step
- polyunsaturated fatty acids are known for prevention and improvement of lifestyle-related diseases (arteriosclerosis, hyperlipidemia, dementia, etc.) and immunosuppressive action (allergy and atopy reduction).
- lifestyle-related diseases arteriosclerosis, hyperlipidemia, dementia, etc.
- immunosuppressive action allergy and atopy reduction.
- Prevention of cardiovascular diseases such as reduction and platelet aggregation inhibitory action, and DHA are expected to have effects such as growth and maintenance of nerve tissue, and improvement of visual acuity (Non-Patent Document 4).
- Seafood lipids are promising as a source of phospholipids and at the same time as a source of highly unsaturated fatty acids such as EPA and DHA.
- extraction and purification of lipids has not been easy.
- lipids containing highly unsaturated fatty acids from crustacean krill. Since krill contains a lot of proteolytic enzymes, even if it is attempted to concentrate lipids from krill in a state where protein is not denatured without heating (hereinafter referred to as unheated), the protein components of krill are immediately decomposed and krill An emulsion is formed together with the phospholipids abundantly contained in the water and flows out into the aqueous layer, making it difficult to recover the lipids.
- a method has been employed in which krill knead is dried to obtain krill meal, and concentrated from here.
- Non-patent Document 5 a method for extracting protein from krill, which is a crustacean
- a method for obtaining protein by coagulating a protein component of krill with heat has been known (Patent Document 5).
- the coagulated product “Okean” obtained by this method is intended to obtain a protein and not a lipid (Non-patent Document 5).
- krill is heated as it is to about 60-75 ° C. and heated, and the resulting aqueous solution as a supernatant is heated to 90 ° C. or higher.
- a method for obtaining a coagulated product by reheating is disclosed (Patent Document 6).
- JP-A-8-325192 Japanese Patent No. 2909508 JP 2004-26267 A International Publication No. 00/23546 Russian Inventor's Certificate No. 227041 International Publication No. 09/027692
- An object of the present invention is to efficiently produce lipids, particularly phospholipids, from crustaceans.
- it is an object to produce lipids of a quality preferable for food applications such as supplements that do not have a bad odor.
- the present inventors have conducted extensive studies on a method for easily separating and concentrating crustacean-derived lipids.
- liquid portions such as crustacean shells, internal organs other than muscles, and internal tissues of craniothoracic regions
- the lipid is localized in the solid part by heating the liquid part containing the water-soluble contaminants and heat-coagulating the protein, and further water-soluble organic acids, amino acids, and peptides. It was found that contaminants can be removed from this solid part by simple methods such as filtration and centrifugation. Further, the solid part was washed with water, and then the lipid was extracted to remove the causative substance of bad odor, and the present invention was completed.
- the gist of the present invention is the following (1) to (11).
- (1) The whole crustacean or its part is squeezed to obtain a squeezed solution, the squeezed solution is heated to a temperature at which the protein contained in the squeezed solution coagulates, and a solid content containing a lipid component and moisture containing a water-soluble component are added.
- Solid-liquid separation, the obtained lipid-containing solid content or the lipid-containing dried product obtained by drying it is washed with water, dehydrated and / or dried, and then the lipid is extracted from the lipid-containing solid content or lipid-containing dried product.
- a method for producing lipids characterized by the following.
- lipids rich in phospholipids from crustaceans it is possible to easily and inexpensively produce lipids rich in phospholipids from crustaceans.
- lipids rich in phospholipids from crustaceans.
- FIG. 1 is the chromatogram obtained in Example 18.
- the present invention extracts a lipid from a solid content obtained by heating a compressed liquid obtained by squeezing the entire crustacean or a part thereof, and solid-liquid separation of a solid content containing a lipid component and water containing a water-soluble component.
- the present invention relates to a method for producing lipids contained in crustaceans.
- the crustacea that is the raw material of the present invention is not particularly limited as long as it belongs to the soft crustacean (shrimp class), but those belonging to the krill or decapod are used in particular. Specific examples include krill, shrimp, crab, and the like, and shrimp head and chest, shrimp gall meal, krill meal, and the like.
- the kind of krill is not particularly limited, but particularly preferred is Euphausia superba.
- These raw materials may be either heated or unheated as long as they contain lipids, but preferably unheated products such as fresh fish (raw), frozen, or thawed frozen products are used. It is done.
- the squeezing method is not particularly limited as long as it is generally used. For example, a hydraulic squeezing machine, a screw press, a meat mining machine, a press dehydrator, a centrifuge, or the like is used in combination.
- the whole shellfish or a part thereof may be pressed to obtain a compressed liquid in an amount corresponding to 5 to 50% of the wet weight.
- 5% or less of the squeezing is not enough to extract and extract the lipid, and 50% or more of the squeezing can sufficiently squeeze the lipid, but there are other contaminants such as water-soluble organic acids, amino acids, peptides, and proteins. It is because the process at the time of mixing and separating and extracting a lipid will become complicated after that. However, when it is intended to obtain a solid content containing a lipid component, it may be compressed by 50% or more. In addition, the compressed rattle that is generated when the compressed liquid is obtained can be used as a feed raw material in accordance with a normal method for using krill.
- the heating method is not particularly limited, and any conventional method may be used.
- the heating temperature may be heated to a temperature at which the protein coagulates, for example, 50 ° C. or higher, preferably 70 to 150 ° C., particularly preferably 85 to 110 ° C. is there. You may heat under pressure or pressure reduction. Thereby, it isolate
- the lipid extraction method is not particularly limited as long as it is a commonly used method, but it is a solvent extraction, pH adjustment or separation / removal of protein components by enzyme treatment such as protease or lipase, supercritical extraction, or a combination thereof.
- the method is used, preferably extraction with an organic solvent, enzymatic treatment followed by extraction with an organic solvent, or supercritical carbon dioxide extraction.
- an appropriate organic solvent for example, alcohols such as methanol, ethanol, propanol, isopropanol, butanol, propylene glycol, butylene glycol, methyl acetate, ethyl acetate, acetone, chloroform, toluene, pentane, hexane, Cyclohexane or the like can be used alone or in combination of two or more.
- lipid is extracted using ethanol or a hexane-ethanol mixture.
- the solvent mixing ratio or the raw material: solvent ratio may be set arbitrarily.
- the enzyme used in the enzyme treatment is not particularly limited as long as it is used in foods, but a protease such as Alcalase (registered trademark) (manufactured by Novozyme), protease A, M, P, pancreatin F (Amano) Enzyme) etc. are used.
- the pH and temperature conditions of the enzyme treatment may be set according to the enzyme used, for example, the method described in Takashi Yamashita, “New Food Processing Technology I” (Industrial Technology Association, 1986, p. 204-284). Etc. can be referred to.
- the supercritical carbon dioxide extraction method may be carried out in accordance with a conventional method, for example, edited by Takashi Yamashita, “New Food Processing Technology I”, Industrial Technology Association, 1986, p. Reference can be made to the method described in 79-102.
- lipids rich in phospholipids from crustaceans can be easily and inexpensively produced.
- the lipid-containing solid content obtained by the above-mentioned method is one in which lipids are efficiently concentrated.
- This lipid-containing solid content contains 35% by weight or more, preferably 40% by weight or more of the lipid based on the whole, and 40% by weight or more of the lipid is characterized by being phospholipid.
- This lipid-containing solid or dried product thereof, or the lipid extracted therefrom by the above method is rich in phospholipids, and lipids containing highly unsaturated fatty acids such as EPA and DHA are obtained. It can be used as a raw material, a food material, or a feed material.
- the method for drying the solid content may follow a conventional method. For example, hot air drying or steam drying may be performed.
- drying by high frequency / microwave heating, vacuum / vacuum drying, freeze-thawing, drying with a desiccant, or a combination thereof may be performed. If the temperature becomes too high during drying, the oxidized lipid will give off a bad odor. Therefore, drying should be performed at 90 ° C. or lower, preferably 75 ° C. or lower, more preferably 55 ° C. or lower. Drying may be performed after producing the lipid-containing solid content, or may be performed after washing with water described below (hereinafter, what has been dried after washing with water may be referred to as a washed / dried product). When producing lipid-containing solids at sea using caught krill, it is better to dry before transportation in consideration of transportation costs.
- the lipid-containing solid content obtained by the above method can be further washed with water to remove the source of krill odor and bad odor.
- Krill odor and bad odor are particularly problematic when concentrated lipids are edible. It is difficult to remove these from the lipid after extraction.
- Phospholipids themselves are both water-soluble and fat-soluble, and cannot be washed with water without being fixed to anything. Therefore, in order to remove odorous components by washing with water, a support that does not adsorb odorous components and adsorbs phospholipids and becomes insoluble in water is required.
- a heat coagulated product of protein contained in the compressed solution of krill is suitable as such a support, and lipids that do not smell are concentrated from krill using the properties.
- the volatile component adsorbed on the column is specified as the original component of krill odor or malodor. That is, the source of krill or malodor in the present invention is a column that adsorbs a volatile component having a molecular weight of 100 to 200, more preferably a column that adsorbs a volatile component having a molecular weight of 100 to 150, more preferably Can be adsorbed with Porapak Q, and no odor remains in the lipid after adsorbed.
- a column distilled at 60 ° C. or lower for 30 minutes or longer may be passed through a column. In this case, it is preferable to gradually raise the temperature from 25 ° C. in order to avoid bumping.
- the lipid-containing solid content obtained by the above-described method can further remove some of the ash and water-soluble protein by washing with water.
- Ash is mainly composed of sodium chloride, potassium and calcium chloride contained in body fluids and seawater adhering to the body surface. Chlorine salts may precipitate as chlorine salts during drying or distillation during the lipid concentration process. Most of the ash is dissolved in water like phospholipids. For this reason, most of the ash is removed by washing with water under conditions where the phospholipid does not dissolve.
- sodium chloride when sodium chloride is deposited, it easily corrodes a metal machine such as a concentrator. For this reason, the amount of sodium chloride in the deposited ash is preferably as small as possible.
- a method for relatively reducing sodium chloride there is a method in which calcium contained in the shell is dissolved by squeezing the entire crustacean or a part thereof.
- the squeezing method is not particularly limited as long as it is generally used.
- a hydraulic squeezing machine, a screw press, a meat mining machine, a press dehydrator, a centrifuge, or the like is used in combination.
- the more squeezed the more calcium chloride is increased and the sodium chloride is relatively decreased.
- the whole crustacean or a part thereof is squeezed to obtain a pressing solution corresponding to 5 to 50% of the wet weight. It is better to squeeze.
- much of the ash is contained in sodium chloride, which is not suitable for such purposes. Washing with water is effective for removing ash from the lipid-containing solid content obtained by heating and coagulating the compressed solution thus obtained.
- Ash is water-soluble as a chlorine salt, but is difficult to elute when confined in a lipid-containing solid. Therefore, it is preferable to finely grind the lipid-containing solid content.
- the ash content can be reduced to 10% or less, preferably 5% or less. Further, sodium chloride in the ash can be reduced to 40% or less, preferably 30% or less, more preferably 20% or less, and even more preferably 10% or less.
- water-soluble proteins include various proteins produced by denaturation by heating in addition to proteins that are inherently water-soluble, and include actin, myosin, troponin, tropomyosin, ATPase, calmodulin and the like.
- 5% or more, preferably 10% or more, more preferably 20% or more of proteins are washed away with respect to the lipid-containing solid content before washing with water.
- the lipid content in the lipid-containing solid content by washing with water is 5% or more per dry matter weight, preferably 10%, compared with the lipid content in the lipid-containing solid content before washing with water. More preferably, it can be increased by 15% or more, and more preferably by 20% or more.
- the ratio of the lipid contained in the lipid-containing solid content can be contained at a ratio of 45% or more, more preferably 50% or more.
- Washing with water to remove krill-smelling components, ash, and water-soluble protein is performed with fresh water and / or seawater in an amount of 4 times the amount of dry matter in the lipid-containing solid, preferably 10 times or more.
- the washing is preferably performed twice or more, more preferably three times or more.
- Washing with water can be performed by pouring water into the lipid-containing solid content in the container, leaving it for 5 minutes or more, and then separating the water. It is effective to sufficiently stir depending on the shape of the lipid-containing solid content.
- the washing with water can also be performed by washing the lipid-containing solid content in a container with running water.
- the lipid-containing solid content obtained by the above method is insoluble in water, the more it is washed, the more it can remove the source of krill or bad odor, ash and water-soluble protein. It is better to keep the lipid-containing solids with a fine mesh so that the solid fragments do not flow out.
- the diameter of the mesh may be fine enough not to be clogged, and is preferably 1 mm or less, more preferably 250 ⁇ m or less.
- the lipid-containing solid is too large, it is difficult to remove the odor source. It is preferably crushed to a diameter of 10 cm or less, more preferably 5 cm or less. However, it is better not to make it less than 1 cm in diameter to prevent spillage.
- the lipid-containing solid can have various specific gravity depending on the content ratio of the protein having a specific gravity higher than water and the lipid having a specific gravity lighter than water. For this reason, even if it centrifuges after water washing, a water
- a press machine such as a screw press to squeeze the lipid-containing solid content
- the lipid-containing solid content obtained by the above method contains a lot of astaxanthin. Since crustacean astaxanthin is contained in a large amount in the tissue inside the shell, and the destruction of the tissue inside the shell is not sufficient only by heat treatment or the like, lipids rich in astaxanthin can be concentrated because the krill is squeezed.
- the squeezing method is not particularly limited as long as it is generally used. For example, a hydraulic squeezing machine, a screw press, a meat mining machine, a press dehydrator, a centrifuge, or the like is used in combination.
- the lipid-containing solid content thus obtained can contain astaxanthin in the lipid at a ratio of 100 ppm, preferably 150 ppm.
- the lipid-containing solid content of the present invention is a composition containing lipids and proteins derived from crustacean pressing liquid, and can contain at least 30% by weight, preferably 40% by weight or more of lipids. Furthermore, sodium chloride can be reduced to 40% or less of the ash by washing with water. Furthermore, it contains 100 ppm or more of astaxanthin.
- the lipid contained in the lipid-containing solid content of the present invention is 50% by weight or more of phospholipid, and 15% by weight or more of EPA and / or DHA.
- This composition contains phospholipids and lipids rich in polyunsaturated fatty acids such as EPA and DHA, which can be used as pharmaceutical raw materials, food raw materials, feed raw materials and the like.
- the compressed liquid is united with the previously obtained thawing drip, heated in a steam-type heating kettle (kneader) with a capacity of 1 t, the temperature reached 95 ° C., and the heating is stopped.
- the solid content) was fractionated by a natural drop method in a stainless steel commercial colander.
- the thermally coagulated product was dried using a steam heating vacuum dryer (Ribocorn manufactured by Okawara Seisakusho, model RM200VD) to obtain 9.0 kg (lot 1) and 15.8 kg (lot 2) of dried products.
- the components of the raw material krill and the dried product of the heat-coagulated product are shown in Table 1.
- the fatty acid composition was analyzed by gas chromatography (Agilent Technology, Model 6890N) after converting the constituent fatty acid to methyl ester in boron trifluoride.
- the gas chromatography column used was J & W Scientific, DB-WAX (model number 122-7032), and the carrier gas was helium, which was detected with a flame ionization detector.
- the dried product of the present heat-coagulated product was not denatured by smell, color, etc. even when stored for 1 year at room temperature, and its lipid component was not oxidized and kept stable.
- the components of the heat coagulated product of the present invention are useful as raw materials for livestock and aquatic feeds.
- each compressed liquid is heated in a 50 L steam-type heating kettle (rice boiler), the temperature reached 95 ° C., heating is stopped, and the generated thermal coagulum (solid content containing lipid) Were separated by a natural drop method in a stainless steel colander.
- Table 3 shows the yield and components of the obtained heat coagulated product of each lot. The yield indicates a weight ratio with respect to the thawing raw material used. The dry weight% indicates the weight% of each component per weight obtained by subtracting the weight of water from the total weight (the same applies to the following examples unless otherwise specified).
- Mass production of heat-coagulated krill press (1) 10 tons of Antarctic krill having a total length of 45 mm or more caught in the Antarctic Ocean in late March 2008 was squeezed with a meat mining machine (Bader, model BAADER 605) immediately after fishing to obtain 3 t of a pressing solution. This pressed solution was treated with an instantaneous heat dryer (manufactured by Nishimura Seiko Co., Ltd., CD dryer CD-500) to obtain 1080 kg of a heat coagulated product. The components of the obtained heat-coagulated product are shown in Tables 17 and 18. The dry weight% indicates the weight% of each component per weight obtained by subtracting the weight of water from the total weight (the same applies to the following examples unless otherwise specified).
- Tables 17 and 18 show the average values and standard deviations of a total of 5 lots produced in the same method in 5 independent experiments, and produced in March and April of the same year.
- the fatty acid composition was analyzed by gas chromatography (Agilent Technology, Model 6890N) after converting the constituent fatty acid to methyl ester in boron trifluoride.
- the gas chromatography column used was J & W Scientific, DB-WAX (model number 122-7032), and the carrier gas was helium, which was detected with a flame ionization detector.
- Mass production of heat-coagulated krill press (2) An Antarctic krill 10t having a total length of 45 mm or more caught in the Antarctic Ocean in mid-June 2008 was compressed with a meat mining machine (Bader, model BAADER605) immediately after the fishing to obtain 3t of a pressing solution. 800 kg of this compressed liquid was stored in a stainless steel tank and heated by directly adding 140 ° C. water vapor. The heating was stopped after confirming that the temperature reached 85 ° C. in heating for about 60 minutes.
- Tables 19 and 20 show the components of the obtained heat-coagulated product. Tables 19 and 20 show the average values and standard deviations of a total of 8 lots produced 8 times in the same year from May to August of the same year. In the table, TG represents triglyceride, FFA represents free fatty acid, and PL represents phospholipid.
- the final salt concentration of the soaking solution at this time was recorded as 0.12% with a refractometer (manufactured by ATAGO).
- the bag was again treated with a centrifugal dehydrator (1 minute), and the solid content (water content 67%) was taken out of the bag.
- 300 g of tocopherol was added thereto and mixed well with a mixer, and dried for 4 hours while stirring with hot air at 60 ° C.
- 48.08 kg of a washed / dried product having a final product temperature of 54 ° C. and a water content of 2.9% was obtained.
- Table 21 and Table 22 show the components of the obtained washed / dried product.
- Table 21 and Table 22 show the average values and standard deviations of the analysis values of 27 lots of washed and dried products produced in the same process 27 times in the same process.
- the components of the obtained extracted lipid are shown in Table 25 and Table 25.
- moisture was measured by AOAC International Standard Method (18th edition) 984.20, and phospholipid was subjected to silica gel chromatography using 300 mg of extracted lipid as a hexane solution, and the adsorbed fraction was collected with chloroform and eluted. The solvent was distilled off under reduced pressure, and the weight was measured. Moreover, a part of solid content a and b was fractionated, and operation after 92% ethanol addition was performed, and the extract liquids K and L for a comparison were obtained, respectively.
- thermocoagulated product and extraction of lipid from dried product To 70 kg of washed and dried product of thermocoagulated product produced in Example 12, 210 liters of 95% ethanol was added and stirred at 50C for 2 hours. did. This was subjected to solid-liquid separation by a 60-mesh natural drop method to obtain an extract A and a solid content a. To the solid a, 210 L of 95% ethanol was added and stirred at 50 ° C. for 2 hours. This was subjected to solid-liquid separation by a 60-mesh natural drop method to obtain an extract B and a solid content b. To the solid content b, 210 L of 95% ethanol was added and stirred at 50 ° C. for 2 hours.
- Extract A, Extract B, and Extract C were combined, and the fine solid content was removed with a filter paper and concentrated under reduced pressure to obtain 24.0 kg of extracted lipid.
- Tables 29 and 30 show the components of the extracted lipid.
- Table 31 shows the analysis value of each heat-coagulated product. Lipids, proteins, and ash in the table indicate weight% with respect to the total weight, and the water content of the thermocoagulated material was calculated by subtracting these from the total 100%. Each lipid composition represents the weight percent of each composition component relative to the total lipid. The total lipid represents the total solid content, that is, the weight percentage of lipid relative to the total weight of lipid, protein and ash.
- “Okean (dry paste)” described in Non-Patent Document 5 has a lipid content of 23.0% to 28.4%, whereas the total lipid content (dried product) of the pressed and heated agglomerates is 34.4% to 48.4% It can be seen that the lipid content of the pressed heated aggregate is very high. Moreover, since water-soluble protein and ash are washed away by water washing, it turns out that the weight% of lipid per solid content has increased from before water washing.
- Example 18 Sensory test of extracted lipids
- Krill oil extracted in Example 18 was sample 1
- Krill odor sample was sample 2
- lipid extracted in example 14 was sample 3
- lipid extracted in example 15 was sample 4
- example 16 The lipid extracted in step 1 was used as a sample 5, 50 ml of each was placed in a vial, and the odor was evaluated by 6 subjects for a sensory test. The results are shown in Table 34.
- the krill odor and bad odor that come out when lipid is extracted from krill are components captured by the rapPorapakQ column when the extracted oil is extracted with superheated steam, and the origin of krill odor and bad odor is heat coagulation It was considered that the product could be removed by washing with water before extracting the lipid.
- the present invention is useful as a simple and inexpensive method for producing lipids rich in phospholipids.
- a composition rich in useful lipids derived from the lipids and crustaceans extracted by the method is useful as a pharmaceutical raw material, a food raw material, or a feed raw material.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Zoology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Marine Sciences & Fisheries (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Husbandry (AREA)
- Nutrition Science (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Neurosurgery (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Neurology (AREA)
- Insects & Arthropods (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Physiology (AREA)
- Pulmonology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Immunology (AREA)
Abstract
Description
そこで従来、オキアミから脂質を濃縮する場合には、粉砕したオキアミを乾燥してオキアミミールを得て、ここから濃縮する方法が採られていたが、この方法では乾燥の過程で悪臭が生じ、食用に耐えられる脂質を得ることが難しい。また方法によっては精製時に灰分が多いため、しばしば装置に付着して装置の腐食や連続運転の妨げとなる。
一方、甲殻類であるオキアミからタンパク質を抽出する方法として従来から、オキアミのタンパク成分を熱により凝固させることでタンパク質を得る方法が知られている(特許文献5)。しかし、この方法で得られる凝固物“Okean”はタンパク質を得ることを目的としており、脂質を得ることは目的としていない(非特許文献5)。
また、本願出願後、優先権主張期間内に開示された発明として、オキアミをそのまま60~75℃付近になるまで熱水を入れて加熱して、得られた上澄みである水溶液を90℃以上に再加熱して凝固物を得る方法が開示されている(特許文献6)。
(1)甲殻類全体またはその部分を圧搾して圧搾液を得、圧搾液に含まれるタンパク質が凝固する温度に圧搾液を加熱し、脂質成分を含む固形分と水溶性成分を含む水分とを固液分離し、得られた脂質含有固形分又はそれを乾燥させた脂質含有乾燥物を水洗いし、脱水及び/又は乾燥した後、それら脂質含有固形分又は脂質含有乾燥物から脂質を抽出することを特徴とする脂質の製造方法。
(2)水洗いにおいて脂質含有固形分又は脂質含有乾燥物の乾物重量あたり4倍以上の水を用いるものである(1)の方法。
(3)水洗いを2回以上行う(1)又は(2)の方法。
(4)脂質含有固形分又は脂質含有乾燥物を直径1cm以上10cm以下に裁断して水洗いを行う(1)乃至(3)いずれかの方法。
(5)水洗い及び/又は脱水を脂質含有固形分又は脂質含有乾燥物をメッシュバッグに入れて行う(1)乃至(4)いずれかの方法。
(6)分子量100~200の揮発成分を吸着する吸着剤で吸着される成分の匂いがで感知できない程度、水洗いを行うことを特徴とする(1)乃至(5)いずれかの方法。
(7)脂質含有乾燥物の乾物重量あたりの灰分が5%以下になる程度、水洗いすることを特徴とする(1)乃至(5)いずれかの方法。
(8)脂質を抽出する方法が、有機溶媒抽出、酵素処理した後有機溶媒抽出、超臨界抽出のいずれかの方法によることを特徴とする(1)乃至(7)いずれかの方法。
(9)甲殻類がオキアミ目に属する甲殻類である、(1)乃至(8)いずれかの方法。
(10)(1)乃至(9)いずれか記載の方法により得た脂質含有組成物。
(11)分子量100~200の揮発成分を吸着するカラムで吸着される成分匂いが官能検査で感知できない程度に除去された(10)の脂質含有組成物。
圧搾方法としては一般に用いられるものであれば特に限定されないが、例えば油圧式圧搾機、スクリュープレス、採肉機、プレス脱水機、遠心分離機等、あるいはこれらを組み合わせて用いる。脂質を取得することを目的とする場合には、甲殻類全体またはその部分を圧搾して湿重量の5~50%に相当する量の圧搾液を得るように圧搾を行うと良い。5%以下の圧搾では脂質を十分に圧搾抽出できていないこと、また50%以上の圧搾では脂質は十分に圧搾できているものの、水溶性有機酸、アミノ酸、ペプチド、タンパク質等他の夾雑物が混入し、その後脂質を分離抽出する際の工程が煩雑になってしまうことからである。但し、脂質成分を含む固形分を取得することを目的とする時には、50%以上圧搾しても構わない。また、圧搾液を得た際に発生する圧搾ガラについては、通常のオキアミの利用方法に準じて飼料原料等に利用することが可能である。
固形分を乾燥する方法は、常法に従えば良い。例えば、熱風乾燥、蒸気での乾燥を行ってもよい。また高周波・マイクロ波加熱での乾燥、真空・減圧乾燥、凍結融解、乾燥剤による乾燥を行ってもよいし、これらを組み合わせてもよい。乾燥する際に高温になりすぎると酸化した脂質が悪臭を発するので、乾燥は90℃以下、好ましくは75℃以下、より好ましくは55℃以下で行うとよい。乾燥は脂質含有固形分を作製した後に行ってもよいし、後述の水洗いの後に行ってもよい(以下、水洗いの後に乾燥を行ったものを洗浄・乾燥物ということもある)。漁獲したオキアミを用いて洋上で脂質含有固形分を作製する場合には、輸送のコストを考えて輸送前に乾燥したほうがよい。洋上乾燥の場合は機器の性能等を考慮して途中で一端止めて、陸揚げしてから再度乾燥を行ってもよい。洋上乾燥から陸上での乾燥をする間に脂質含有固形分が高温に晒されてしまうことによる悪臭の発生がなければ、その後に行う水洗いによりオキアミ臭及び悪臭の元が除去できるからである。また輸送期間が長い場合には腐敗してしまう恐れがあるため、冷蔵又は冷凍で輸送することが好ましい。
Porapak Qで吸着させることができ、吸着させた後の脂質には臭いが残らない。吸着に際しては60℃以下で30分以上蒸留したものをカラムに通せばよく、この際の加熱は突沸を避けるために25℃から徐々に昇温させることが好ましい。ただしカラムに吸着させる方法で脂質からオキアミ臭あるいは悪臭の元の成分を除去すると、膨大な手間と費用を要するので実用的ではない。このため、本発明のように、水洗いという簡便な操作で除去することはたいへん実用的である。
また特に塩化ナトリウムが析出すると濃縮装置など金属製の機械を腐食させやすい。このため析出した灰分の中の塩化ナトリウムはできるだけ少ないほうがよい。塩化ナトリウムを相対的に減らす方法として、甲殻類全体またはその部分を圧搾して、その殻に含まれるカルシウムを溶解させておく方法がある。圧搾方法としては一般に用いられるものであれば特に限定されないが、例えば油圧式圧搾機、スクリュープレス、採肉機、プレス脱水機、遠心分離機等、あるいはこれらを組み合わせて用いる。多く圧搾すればするほど塩化カルシウムが相対的に増加して、塩化ナトリウムが相対的に減少するが、多く圧搾しすぎると上述のように脂質の濃縮という点においては問題となる。このため、脂質中に含まれる灰分に含まれる塩化ナトリウムを相対的に減少させるためには、甲殻類全体またはその部分を圧搾して湿重量の5~50%に相当する量の圧搾液を得るように圧搾を行うと良い。甲殻類全体またはその部分を圧搾しない方法では灰分に含まれる多くが塩化ナトリウムとなってしまい、このような目的には適さない。
このようにして得られた圧搾液を加熱凝固して得られる脂質含有固形分から灰分を除去するためには、水洗いすることが有効である。灰分は塩素塩としては水溶性であるが、脂質含有固形分の中に閉じ込められた状態では溶出しにくい。そこで、脂質含有固形分を細かく粉砕して行うことが好ましい。このようにして脂質含有固形分を水洗いすることにより灰分が10%以下、好ましくは5%以下に低減させることができる。また、灰分のうち塩化ナトリウムは、40%以下、好ましくは30%以下、より好ましくは20%以下、さらに好ましくは10%以下に低減することができる。
脂質含有固形分は水より比重が重いタンパク質と水より比重が軽い脂質の含有比率により様々な比重を持ち得る。このため水洗い後に遠心分離を行っても効率的に水分を除去することができない。水分の分離は脂質含有固形分をスクリュープレスなどの圧搾機を用いるか、又は脂質含有固形分を留めるサイズのメッシュを用いた自然落下法又はメッシュで区切りを持たせた遠心管若しくはメッシュの袋に脂質含有固形分を閉じ込めて行う遠心分離を行うことが好ましい。このようにして、脂質含有固形分から臭いの成分、灰分及び/又は水溶性タンパク質を除去することができる。
2005年7月下旬に南極海にて漁獲し、直ちに-30℃に冷凍した全長45mm以上のナンキョクオキアミ400kgを室温(15℃)にて通風解凍した。この解凍オキアミを油圧式圧搾機(東京テクノ社製、原料セル約2m×約68cm×約40cmH)を用いて搾液率(解凍オキアミ投入量に対する圧搾液の収量)13重量%(ロット1)及び26重量%(ロット2)にて圧搾した。圧搾液は先に得られた解凍ドリップと合一し、容量1tの蒸気式加熱釜(ニーダー)にて加熱し、95℃達温を確認して加熱を停止し、発生した熱凝固物(脂質含有固形分)をステンレス製市販ザルにて自然落下法にて分別した。熱凝固物は蒸気加熱型真空乾燥機(大川原製作所製リボコーン、型式RM200VD)を用いて乾燥し、乾燥物9.0kg(ロット1)及び15.8kg(ロット2)を得た。原料のオキアミ及び得られた熱凝固物の乾燥物の成分を表1に示す。
本熱凝固物の乾燥物は、室温で1年間保存した場合でも、におい、色などで判別される変性はなく、その脂質成分が酸化されず安定に保持された。また、表1および表2に示されるように、本発明の熱凝固物の成分は畜産及び水産飼料原料として有用である。
実施例1と同じオキアミを室温(8℃)で通風解凍し、解凍ドリップを除去した。この解凍オキアミをスクリュープレス脱水機(富国工業社製SHX-200型×1.5ML)に投入して、搾液率(解凍オキアミ投入量に対する圧搾液の収量)17~36重量%にて圧搾液を得た(ロット3~6)。それぞれの圧搾液の約5kgを容量50Lの蒸気式加熱釜(ライスボイラー)にて加熱し、95℃達温を確認して加熱を停止し、発生した熱凝固物(脂質を含有する固形分)をステンレス製市販ザルにて自然落下法にて分別した。得られた各ロットの熱凝固物の収率及び成分を、表3に示す。収率は用いた解凍原料に対する重量比率を示す。なお乾重%とは全重量から水分重量を引いた重量あたりの各成分の重量%を示す(特に記載のある場合の除き、以下の実施例で同じ)。
2006年7月中旬に南極海にて漁獲した全長45mm以上のナンキョクオキアミ10tを漁獲直後に採肉機(バーダー社製、型式BAADER605)にて圧搾し、圧搾液3tを得、直ちに冷凍した。この冷凍圧搾液を蒸気式加熱釜中加熱し、95℃達温を確認して加熱を停止した。加熱物全量を200メッシュの濾布を用いて遠心脱水機(大栄製作所製型式DT-1)に投入し、エキス(濾液)を分離し熱凝固物(脂質含有固形分)を得た。原料及び得られた熱凝固物の成分を、表6に示す。
実施例3にて製造した熱凝固物(脂質含有固形分)の乾燥品10gを用い、100mLのクロロホルム中にてホモジナイズ処理し、抽出油3.71gを得た。この抽出油をシリカゲル(旭硝子社製、マイクロスフェアゲル、型番M.S GEL SIL、300g)カラムに吸着させ、クロロホルムにて中性脂質など洗脱した。その後移動層をメタノールに変更してリン脂質0.228gを回収した。熱凝固物乾燥品10g中の脂質の分析値は4.72gであった。本リン脂質についてイアトロスキャン法(展開溶媒はクロロホルム:メタノール:水=65:25:4)で検討したところ、このリン脂質はホスファチジルコリンが96重量%、ホスファチジルエタノールアミンが4重量%を占めることがわかった。また、本実施例により得られたリン脂質の脂肪酸組成について、実施例1と同様に分析した。結果を表8に示す。
実施例3にて製造した熱凝固物(脂質を含有する固形分)の乾燥品2.00g(総脂質含有量の分析値は0.94g)を用い、50mLのヘキサン-エタノール混液にて脂質を抽出した(原料:溶媒=1:25)。この脂質を用い、2種類の溶媒の混合比を100:0から0:100まで変更して抽出効率を比較した。抽出油の収量と、これをイアトロスキャン法にて脂質分析したリン脂質の純度を表9に示す。
実施例3にてオキアミ圧搾液から得た熱凝固物(脂質を含有する固形分)乾燥品を用い、これからヘキサン-エタノール混合比60:40の溶媒を用いて、実施例5と同様の手順で抽出油を得た。ただし、原料:溶媒比を1:5~1:20に変更した。抽出油について分析結果を表10に示す。
実施例3において製造した熱凝固物(脂質を含有する固形分)3gに対し、蒸留水30gを加えてホモジナイズ処理した。熱凝固物は均一に分散した。この液(pH7.5)に対し、市販液状酵素(ノボザイム社製アルカラーゼ2.4L)を1μLまたは市販粉末状酵素(天野エンザイム製プロテアーゼA、プロテアーゼM、プロテアーゼPまたはパンクレアチンF)を1mg添加して、50℃で2時間酵素反応を作用させた。その後反応液のpHを2規定濃度塩酸で1.4に調整し、50℃で遠心分離(2230g、10分)処理した。表層に分離した油を含む液層全体を回収した。この液層全体と沈殿物とに含まれる脂質をそれぞれクロロホルム:メタノール=2:1混合溶媒にて定量し、回収率を求めた。結果を表11に示す。
実施例3において製造した熱凝固物(脂質を含有する固形分;水分61.2重量%のもの)またはこれから得た乾燥物(水分2.0重量%)を用い、34.3MPa、40℃の条件にて超臨界二酸化炭素による脂質成分の抽出を実施し、抽出物と抽出残渣とを得た。結果を表12に示す。
2007年4~8月に南極海にて漁獲後直ちに-30℃に冷凍した全長30mm~44mmのナンキョクオキアミ20kgを冷蔵庫内(4℃)にて一晩通風解凍した。この解凍オキアミをフィルタースクリュープレス(荒井鉄工所製、型式MM-2)を用いて、搾液率(解凍オキアミ投入量に対する圧搾液の収量)40~45重量%にて圧搾した。得られた圧搾液の約5kgを容量50Lの蒸気式加熱釜(ライスボイラー)にて加熱し、95℃達温を確認して加熱を停止し、発生した熱凝固物(脂質を含有する固形分)をステンレス製市販ザルにて自然落下法にて分別した。同じ実験を異なるオキアミのロットで3回行い、原料及び得られた熱凝固物の成分を表14及び表15にそれぞれ示す。また、熱凝固物の脂質組成及び脂肪酸組成を表16に示す。
2008年3月下旬に南極海にて漁獲した全長45mm以上のナンキョクオキアミ10tを漁獲直後に採肉機(バーダー社製、型式BAADER605)にて圧搾し、圧搾液3tを得た。この圧搾液を瞬間加熱乾燥機(西村鐵工所製、CDドライヤー CD-500)にて処理し、熱凝固物を1080kg得た。得られた熱凝固物の成分を表17、表18に示す。乾重%とは全重量から水分重量を引いた重量あたりの各成分の重量%を示す(特に記載のある場合の除き、以下の実施例で同じ)。また同様の方法で独立に5回の実験を行い、同年3~4月の間に生産した合計5ロットの平均値と標準偏差を表17、表18に示す。
なお、脂質組成はベンゼン:クロロホルム:酢酸=150:60:1.5の展開溶媒により分離した各脂質成分を薄層自動検出装置(三菱化学ヤトロン社製、型式イアトロスキャン(登録商標)MK-6)を用いて定量した。また、脂肪酸組成は構成脂肪酸を三フッ化ホウ素中メチルエステル化してガスクロマトグラフィー(アジレント・テクノロジー社、型式6890N)により分析した。使用したガスクロマトグラフィー用カラムはJ&W Scientific社、DB-WAX(型番122-7032)、キャリアガスはヘリウムを使用し、水素炎イオン化検出器で検出した。
2008年6月中旬に南極海にて漁獲した全長45mm以上のナンキョクオキアミ10tを漁獲直後に採肉機(バーダー社製、型式BAADER605)にて圧搾し、圧搾液3tを得た。この圧搾液800kgをステンレスタンクに収納し、140℃の水蒸気を直接投入することにより加熱した。約60分の加熱において85℃達温を確認して加熱を停止した。タンク底部のバルブを開放し、目合い2mmメッシュを通過する液状成分を自然落下により除去し、固形分(熱凝固物)は同量の水をシャワリングすることにより洗浄した後、アルミ製のトレイに12kgずつ収納してコンタクトフリーザにより急速冷凍した。得られた熱凝固物の成分を表19、表20に示す。また同様の実験を8回行い、同年5~8月の間に生産した合計8ロットの平均値と標準偏差を表19、表20に示す。尚、表中TGはトリグリセリド、FFAは遊離脂肪酸、PLはリン脂質をそれぞれ表す。
実施例11で製造し、冷凍庫で3ヶ月保管した熱凝固物300kgをフローズンカッター(湘南産業社製、FZ型)にて粉砕し、ナイロン袋(20メッシュ)に収納した。これを75℃の温水900リットルに投入して60分間漬け込んだ(終温度36℃)。次いで遠心脱水機(タナベ製遠心分離機 O-30、60秒)で処理し、袋を75℃温水900リットル(新たに調製)に40分間漬け込んだ(終温度61℃)。このときの漬け込み液の塩分終濃度は屈折率計(ATAGO社製)にて0.12%と記録された。袋を再度遠心脱水機処理(1分)し、固形分(水分67%)を袋から取り出した。これにトコフェロールを300g添加してミキサーにてよく混和し、60℃の熱風にて撹拌しながら4時間乾燥した。その結果、最終品温54℃、水分2.9%の洗浄・乾燥物48.08kgを得た。得られた洗浄・乾燥物の成分を表21、表22に示す。また同様の実験を27回行い、同工程で製造した洗浄・乾燥物合計27ロットの分析値の平均値と標準偏差を表21、表22に示す。
実施例11で製造し、冷凍庫で3ヶ月保管した熱凝固物1トンを3000リットルの水に投入し、これを撹拌しながら加熱して65℃に達温後10分保持した。24メッシュナイロンを用いて水切りし、固形分を3000リットルの水(20℃)に投入した。15分の撹拌後、24メッシュナイロンにて水切りし、さらに遠心脱水機(タナベ製遠心分離機 O-30、15秒)で処理して固形分564kg(水分73%)を得た。このものにトコフェロール1.54kgを添加し、ミキサーでよく混和し、熱風温度60℃にて3.2時間乾燥し、洗浄・乾燥物148.4kgを得た。得られた洗浄・乾燥物の成分を表23、表24に示す。
実施例10で製造し、冷凍庫で3ヶ月保管した熱凝固物1トンをフローズンカッターにて粉砕し、80~90℃の熱水3000リットル中に投入した。これを温度を保持したまま30分間撹拌し、60メッシュにてろ過し、固形分aを得た。固形分aに対し、80~90℃の熱水3000リットルを添加し、温度を保持したまま30分間撹拌し、さらに60メッシュにて排水して固形分bを得た。同じ操作を繰り返し、固形分cを得て、再度同じ操作にて固形分dを得た。固形分dに対して、92%エタノールを3000リットル添加して、15分間撹拌し、60メッシュにて排液することにより固形分eおよびエタノール置換液Fを得た。固形分eに92%エタノールを3000リットル添加して常圧で2時間還流させ脂質を抽出した。脂質抽出液Gは60メッシュにてろ過し、残渣Hを得た。残渣Hに対し、3000リットルの92%エタノールを添加して常圧で2時間還流させたのち60メッシュで処理し、脂質抽出液Iおよび残渣Jを得た。エタノール置換液F、脂質抽出液G、脂質抽出液Iを合一して減圧濃縮機でエタノールおよび水を溜去し、抽出脂質88kgを得た。得られた抽出脂質の成分を表25、表25に示す。なお、表25において水分はAOAC国際基準法(第18版)984.20により測定し、またリン脂質は抽出脂質300mgをヘキサン溶液としてシリカゲルクロマトグラフィに供し、吸着画分をクロロホルムにて回収し、溶出させ溶媒を減圧溜去させた後に重量にて計測した。また固形分a、bの一部を分取して92%エタノール添加以後の操作を行って比較用抽出液K、Lをそれぞれ得た。
実施例13にて製造した洗浄・乾燥物299.6kgに99%エタノール1200リットルを添加し、60℃に加温して2時間撹拌した。その後ナイロンの100メッシュを用い自然落下法により固液分離して抽出液Aおよび抽出粕aを得た。抽出粕aに99%エタノール800リットルを添加し、60℃に加温して2時間撹拌後ナイロン100メッシュを用いて固液分離し、抽出液Bおよび抽出粕bを得た。抽出粕bに99%エタノール700リットルを添加し、60℃に加温して2時間撹拌後ナイロン100メッシュを用いて固液分離し、抽出液Cおよび390kg(うち105℃、4時間の乾燥減量は61.8%)の抽出粕cを得た。抽出液A、抽出液B及び抽出液Cを合一すると2089kgとなった。これを液温60℃以下で減圧濃縮し、エタノールおよび水を溜去し、抽出脂質141.6kgを得た。得られた抽出脂質の成分を表27、表28に示す。
実施例12にて製造した熱凝固物の洗浄・乾燥物70kgに対し、95%エタノール210リットルを加え、50℃にて2時間撹拌した。これを60メッシュ自然落下法により固液分離して、抽出液Aおよび固形分aを得た。固形分aに対し95%エタノール210Lを加え、50℃にて2時間撹拌した。これを60メッシュ自然落下法により固液分離して、抽出液Bおよび固形分bを得た。固形分bに対し95%エタノール210Lを加え、50℃にて2時間撹拌した。これを60メッシュ自然落下法により固液分離して、抽出液Cおよび固形分c(抽出残渣:58.7kg)を得た。抽出液A、抽出液B及び抽出液Cを合一し、ろ紙にて微小な固形分を排除したものを減圧濃縮し、抽出脂質24.0kgを得た。この抽出脂質の成分を表29、表30に示す。
2008年6~7月に南極海にて漁獲し、冷凍したオキアミ(生冷)を室温で解凍した。このオキアミを30メッシュのナイロンシーブを用いて圧搾し、全重量に対して5~53重量%の圧搾液を得るような圧搾率で圧搾した。得られた各圧搾液を85℃以上で5分間加熱し、熱凝固物を調製した。また圧搾率50%の圧搾液から得られた熱凝固物を4倍量の水で2回洗浄し、得られた洗浄物を60℃の熱風にて撹拌しながら4時間乾燥して、熱凝固物の洗浄・乾燥物を得た。各熱凝固物の分析値を表31に示す。表中の脂質、タンパク質、灰分は全体重量に対しての重量%を示し、熱凝固物の水分についてはこれらを全体100%から引いたものとして計算した。各脂質組成は全脂質に対しての各組成成分の重量%を示す。総脂質は全体固形分すなわち、脂質とタンパク質と灰分を足した重量に対しての脂質の重量%を示す。
また、水洗いにより水溶性のタンパク質と灰分が洗い流されるため、固形分あたりの脂質の重量%は水洗い前より増加していることが分かる。
実施例10に示した加熱凝集物(乾燥)Fを原料にし、99.8%エタノール(9倍量)を用いることによりオキアミ油を抽出した。
この抽出油に15倍量の蒸留水を加えて加熱し、生じた水蒸気を捕集した後にPorapakQ(Waters社製、50~80mesh)に吸着させ、エチルエーエーテルにより溶出させてオキアミ臭気サンプルとした。
更にこのオキアミ臭気サンプルを表32の条件に設定したGCを用いて匂い嗅ぎ法(スニッフィング)によりオキアミ臭気成分の画分を確認した。
実施例18で抽出したオキアミ油をサンプル1、オキアミ臭気サンプルをサンプル2、実施例14で抽出した脂質をサンプル3、実施例15で抽出した脂質をサンプル4、実施例16で抽出した脂質をサンプル5とし、それぞれ50mlずつバイアル瓶に入れ、臭いの評価を6人の被験者で官能検査を行った。結果を表34に示す。
Claims (11)
- 甲殻類全体またはその部分を圧搾して圧搾液を得、圧搾液に含まれるタンパク質が凝固する温度に圧搾液を加熱し、脂質成分を含む固形分と水溶性成分を含む水分とを固液分離し、得られた脂質含有固形分又はそれを乾燥させた脂質含有乾燥物を水洗いし、脱水及び/又は乾燥した後、それら脂質含有固形分又は脂質含有乾燥物から脂質を抽出することを特徴とする脂質の製造方法。
- 水洗いにおいて脂質含有固形分又は脂質含有乾燥物の乾物重量あたり4倍以上の水を用いるものである請求項1の方法。
- 水洗いを2回以上行う請求項1又は2の方法。
- 脂質含有固形分又は脂質含有乾燥物を直径1cm以上10cm以下に裁断して水洗いを行う請求項1乃至3いずれかの方法。
- 水洗い及び/又は脱水を脂質含有固形分又は脂質含有乾燥物をメッシュバッグに入れて行う請求項1乃至4いずれかの方法。
- 分子量100~200の揮発成分を吸着する吸着剤で吸着される成分の匂いが感知できない程度、水洗いを行うことを特徴とする請求項1乃至5いずれかの方法。
- 脂質含有乾燥物の乾物重量あたりの灰分が5%以下になる程度、水洗いすることを特徴とする請求項1乃至5いずれかの方法。
- 脂質を抽出する方法が、有機溶媒抽出、酵素処理した後有機溶媒抽出、超臨界抽出のいずれかの方法によることを特徴とする請求項1乃至7いずれかの方法。
- 甲殻類がオキアミ目に属する甲殻類である、請求項1乃至8いずれかの方法。
- 請求項1乃至9いずれか記載の方法により得た脂質含有組成物。
- 分子量100~200の揮発成分を吸着するカラムで吸着される成分匂いが官能検査で感知できない程度に除去された請求項10の脂質含有組成物。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010530853A JP5703022B2 (ja) | 2008-09-26 | 2009-09-24 | 脂質の製造方法 |
CN200980142656.4A CN102202519B (zh) | 2008-09-26 | 2009-09-24 | 脂质的制造方法 |
CA2738285A CA2738285C (en) | 2008-09-26 | 2009-09-24 | Method for producing lipids |
EP09816165.6A EP2332424B1 (en) | 2008-09-26 | 2009-09-24 | Method for producing lipid |
US13/120,842 US8568819B2 (en) | 2008-09-26 | 2009-09-24 | Solid composition containing lipids from crustaceans |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008-248986 | 2008-09-26 | ||
JP2008248986 | 2008-09-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2010035750A1 true WO2010035750A1 (ja) | 2010-04-01 |
Family
ID=42059748
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2009/066530 WO2010035750A1 (ja) | 2008-09-26 | 2009-09-24 | 脂質の製造方法 |
PCT/JP2009/066529 WO2010035749A1 (ja) | 2008-09-26 | 2009-09-24 | 脂質の濃縮方法 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2009/066529 WO2010035749A1 (ja) | 2008-09-26 | 2009-09-24 | 脂質の濃縮方法 |
Country Status (7)
Country | Link |
---|---|
US (2) | US8784921B2 (ja) |
EP (2) | EP2332424B1 (ja) |
JP (2) | JP5703021B2 (ja) |
KR (3) | KR20180010325A (ja) |
CN (3) | CN102202519B (ja) |
CA (2) | CA2738282C (ja) |
WO (2) | WO2010035750A1 (ja) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011116680A (ja) * | 2009-12-02 | 2011-06-16 | Nippon Suisan Kaisha Ltd | 生活習慣病予防又は改善剤 |
WO2012029898A1 (ja) * | 2010-09-01 | 2012-03-08 | 日本水産株式会社 | アルコール性障害緩和剤 |
JP2012051865A (ja) * | 2010-09-03 | 2012-03-15 | Nippon Suisan Kaisha Ltd | 鎮静および睡眠促進剤 |
WO2012165586A1 (ja) * | 2011-05-31 | 2012-12-06 | 日本水産株式会社 | 脳機能改善剤 |
WO2013002404A1 (ja) * | 2011-06-29 | 2013-01-03 | 日本水産株式会社 | 恐怖記憶の軽減方法 |
JP2013053109A (ja) * | 2011-09-05 | 2013-03-21 | Teikyo Univ | リン脂質結合型dha増加剤 |
JP2013053110A (ja) * | 2011-09-05 | 2013-03-21 | Teikyo Univ | 経口投与剤 |
JP2013216654A (ja) * | 2012-04-05 | 2013-10-24 | Nippon Suisan Kaisha Ltd | 脳萎縮抑制剤 |
JP2014509339A (ja) * | 2011-02-11 | 2014-04-17 | テドク・エフアールディー・カンパニー・リミテッド | オキアミ油の製造方法およびこの方法で製造されたオキアミ油 |
CN103687603B (zh) * | 2011-06-29 | 2016-11-30 | 日本水产株式会社 | 磷虾油在制备心理创伤后应激障碍的治疗或预防的制剂中的用途 |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102202519B (zh) * | 2008-09-26 | 2014-12-17 | 日本水产株式会社 | 脂质的制造方法 |
WO2012103685A1 (en) * | 2011-02-01 | 2012-08-09 | Nippon Suisan Kaisha, Ltd. | Sexual function improving agent |
ES2402723B1 (es) * | 2011-10-31 | 2014-03-12 | Restaurante Casa José Aranjuez S.L. | Procedimiento para la elaboración de un concentrado de marisco rico en grasa |
CN103356664A (zh) * | 2012-04-05 | 2013-10-23 | 日本水产株式会社 | 脑萎缩预防剂 |
CN102876444A (zh) * | 2012-09-18 | 2013-01-16 | 中国水产科学研究院东海水产研究所 | 一种虾类油脂的无溶剂制备方法 |
AU2014203179C1 (en) | 2013-06-14 | 2017-05-04 | Aker Biomarine Antarctic As | Lipid extraction processes |
US20180207204A1 (en) * | 2014-02-11 | 2018-07-26 | Enzymotec Ltd. | Krill oil preparations with optimal mineral and metal composition, low impurities and low and stable tma levels |
CA2967772C (en) * | 2014-11-14 | 2021-08-10 | Tharos Ltd. | Solvent-free process for obtaining phospholipids and neutral enriched krill oils using melting and evaporation |
CN104479850B (zh) * | 2014-12-15 | 2015-10-21 | 中国水产科学研究院黄海水产研究所 | 从鲜南极磷虾中提取高磷脂含量磷虾油的方法 |
CN107429194A (zh) * | 2015-03-18 | 2017-12-01 | 株式会社Ihi | 脂质组合物及其制造方法 |
WO2016161575A1 (zh) * | 2015-04-08 | 2016-10-13 | 江南大学 | 一种对南极磷虾脱水提取虾油的方法 |
CN109054989A (zh) * | 2018-08-27 | 2018-12-21 | 浙江工业大学 | 一种热敏性南极磷虾油脂的萃取方法 |
US11186597B1 (en) | 2021-06-24 | 2021-11-30 | King Abdulaziz University | Method of extracting phospholipids from fish roe |
CL2022000259A1 (es) * | 2022-01-31 | 2023-01-20 | Proceso de fabricacion de harina de crustaceos; proceso de extraccion de componentes nutricionales; suplemento alimenticio. | |
KR102609642B1 (ko) | 2022-12-27 | 2023-12-05 | 휴먼이엔씨주식회사 | 인도 및 자전거 교량용 길이 변경이 가능한 보강캡 구조물 |
Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5276455A (en) * | 1975-12-23 | 1977-06-27 | Nikken Chemicals Co Ltd | Method of producing highhprotein solution and powder |
JPS52114046A (en) * | 1976-03-19 | 1977-09-24 | Nikken Chemicals Co Ltd | Method of producing protein solution and powder |
JPS5476858A (en) * | 1977-11-28 | 1979-06-19 | Tokai Suisan Kikai Kk | Production of protein concentrate of *okiami* |
JPH08325192A (ja) | 1995-05-25 | 1996-12-10 | Bizen Kasei Kk | ドコサヘキサエン酸含有リン脂質の製造方法 |
JPH10179038A (ja) * | 1996-12-21 | 1998-07-07 | Advanced Protein Technol Inc | 筋肉源から蛋白質組成物を分離するプロセス及び蛋白質組成物 |
JP2909508B2 (ja) | 1989-02-14 | 1999-06-23 | マルハ株式会社 | オキアミリン脂質の分取方法 |
WO2000023564A2 (en) | 1998-10-16 | 2000-04-27 | Xencor, Inc. | Protein design automation for protein libraries |
WO2000023546A1 (en) * | 1998-10-21 | 2000-04-27 | Universite De Sherbrooke | Method of extracting lipids from marine and aquatic animal tissues |
JP2003003190A (ja) * | 2001-06-25 | 2003-01-08 | Yaizu Suisankagaku Industry Co Ltd | 高度不飽和脂肪酸供給組成物 |
JP2004026267A (ja) | 2002-06-28 | 2004-01-29 | Fuji Photo Film Co Ltd | 記録媒体包装体 |
WO2007105734A1 (ja) * | 2006-03-13 | 2007-09-20 | Nippon Suisan Kaisha, Ltd. | 不凍活性を有する甲殻類由来タンパク質 |
WO2009027692A2 (en) | 2007-08-29 | 2009-03-05 | Aker Biomarine Asa | A new method for making krill meal |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2528788B2 (ja) * | 1994-05-16 | 1996-08-28 | 有限会社アイテック | 飼料添加剤 |
US6399105B1 (en) * | 1999-01-20 | 2002-06-04 | Peter Donald Collin | Sea cucumber carotenoid lipid fraction products and methods of use |
CN100403917C (zh) * | 2000-04-12 | 2008-07-23 | 威斯特伐利亚分离器股份公司 | 含油和极性脂质的天然原料的分级分离方法 |
DE10018213A1 (de) * | 2000-04-12 | 2001-10-25 | Westfalia Separator Ind Gmbh | Verfahren zur Fraktionierung von öl-und lecithinhaltigen nativen Rohstoffen |
JP2004026767A (ja) | 2002-06-27 | 2004-01-29 | Asahi Kasei Chemicals Corp | 魚介類由来のリン脂質の製造方法 |
AR059659A1 (es) * | 2006-01-13 | 2008-04-23 | Alfa Copenhagen S S | Metodo para la extraccion |
AR059012A1 (es) * | 2006-01-13 | 2008-03-05 | Aker Biomarine Asa | Extractos derivados del krill |
JP2010510208A (ja) * | 2006-11-16 | 2010-04-02 | プロノヴァ バイオファーマ ノルゲ アーエス | オキアミ油およびミールの製造方法 |
EP2144618B1 (en) | 2007-03-28 | 2013-05-15 | Aker Biomarine ASA | Bioeffective krill oil compositions |
US20100226977A1 (en) * | 2007-08-29 | 2010-09-09 | Aker Biomarine Asa | Low viscosity phospholipid compositions |
CN102202519B (zh) * | 2008-09-26 | 2014-12-17 | 日本水产株式会社 | 脂质的制造方法 |
JP5276455B2 (ja) | 2009-01-23 | 2013-08-28 | スタンレー電気株式会社 | 光半導体装置モジュール |
-
2009
- 2009-09-24 CN CN200980142656.4A patent/CN102202519B/zh not_active Expired - Fee Related
- 2009-09-24 CA CA2738282A patent/CA2738282C/en not_active Expired - Fee Related
- 2009-09-24 EP EP09816165.6A patent/EP2332424B1/en not_active Not-in-force
- 2009-09-24 CN CN200980142700.1A patent/CN102196733B/zh not_active Expired - Fee Related
- 2009-09-24 US US13/120,875 patent/US8784921B2/en not_active Expired - Fee Related
- 2009-09-24 WO PCT/JP2009/066530 patent/WO2010035750A1/ja active Application Filing
- 2009-09-24 JP JP2010530852A patent/JP5703021B2/ja not_active Expired - Fee Related
- 2009-09-24 KR KR1020187001606A patent/KR20180010325A/ko not_active Application Discontinuation
- 2009-09-24 KR KR20117007027A patent/KR20110073481A/ko active Application Filing
- 2009-09-24 CN CN201410646212.7A patent/CN104522293B/zh not_active Expired - Fee Related
- 2009-09-24 JP JP2010530853A patent/JP5703022B2/ja not_active Expired - Fee Related
- 2009-09-24 US US13/120,842 patent/US8568819B2/en not_active Expired - Fee Related
- 2009-09-24 WO PCT/JP2009/066529 patent/WO2010035749A1/ja active Application Filing
- 2009-09-24 CA CA2738285A patent/CA2738285C/en not_active Expired - Fee Related
- 2009-09-24 EP EP09816164A patent/EP2335494A4/en not_active Withdrawn
- 2009-09-24 KR KR1020117007028A patent/KR101650596B1/ko active IP Right Grant
Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5276455A (en) * | 1975-12-23 | 1977-06-27 | Nikken Chemicals Co Ltd | Method of producing highhprotein solution and powder |
JPS52114046A (en) * | 1976-03-19 | 1977-09-24 | Nikken Chemicals Co Ltd | Method of producing protein solution and powder |
JPS5476858A (en) * | 1977-11-28 | 1979-06-19 | Tokai Suisan Kikai Kk | Production of protein concentrate of *okiami* |
JP2909508B2 (ja) | 1989-02-14 | 1999-06-23 | マルハ株式会社 | オキアミリン脂質の分取方法 |
JPH08325192A (ja) | 1995-05-25 | 1996-12-10 | Bizen Kasei Kk | ドコサヘキサエン酸含有リン脂質の製造方法 |
JPH10179038A (ja) * | 1996-12-21 | 1998-07-07 | Advanced Protein Technol Inc | 筋肉源から蛋白質組成物を分離するプロセス及び蛋白質組成物 |
WO2000023564A2 (en) | 1998-10-16 | 2000-04-27 | Xencor, Inc. | Protein design automation for protein libraries |
WO2000023546A1 (en) * | 1998-10-21 | 2000-04-27 | Universite De Sherbrooke | Method of extracting lipids from marine and aquatic animal tissues |
JP2003003190A (ja) * | 2001-06-25 | 2003-01-08 | Yaizu Suisankagaku Industry Co Ltd | 高度不飽和脂肪酸供給組成物 |
JP2004026267A (ja) | 2002-06-28 | 2004-01-29 | Fuji Photo Film Co Ltd | 記録媒体包装体 |
WO2007105734A1 (ja) * | 2006-03-13 | 2007-09-20 | Nippon Suisan Kaisha, Ltd. | 不凍活性を有する甲殻類由来タンパク質 |
WO2009027692A2 (en) | 2007-08-29 | 2009-03-05 | Aker Biomarine Asa | A new method for making krill meal |
Non-Patent Citations (9)
Title |
---|
"Atarashii Shokuhin Kako Gijutsu I", 1986, KOGYO CIJUTSUKAI, pages: 79 - 102 |
"Atarashii Shokuhin Kako Gijutsu I", 1986, KOGYO GIJUTSUKAI, pages: 204 - 284 |
"Bailey's Industrial Oil and Fat Products", vol. 1, 1996, JOHN WILEY & SONS, pages: 336 |
"Gyoyu to Maiwasi", 1991, KOSEISHA KOSEIKAKU, pages: 21 - 28 |
"Saishin Shokuhin Kakou Koza - Shokuyo Yushi to Sono Kako", 1981, KENPAKUSHA, pages: 49 - 74 |
A. CLARKE, JOURNAL OF EXPERIMENTAL MARINE BIOLOGY AND ECOLOGY, vol. 43, no. 3, 1980, pages 221 - 236 |
See also references of EP2332424A4 |
VOPR PITAN, 1977, pages 70 - 73 |
Z.E.SIKORSKI ET AL.: "THE UTILIZATION OF KRILL FOR FOOD", FOOD PROCESS ENG, vol. 1, 1980, pages 845 - 855, XP008136640 * |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011116680A (ja) * | 2009-12-02 | 2011-06-16 | Nippon Suisan Kaisha Ltd | 生活習慣病予防又は改善剤 |
WO2012029898A1 (ja) * | 2010-09-01 | 2012-03-08 | 日本水産株式会社 | アルコール性障害緩和剤 |
US9061035B2 (en) | 2010-09-01 | 2015-06-23 | Nippon Suisan Kaisha, Ltd. | Alcoholic injury mitigating agent |
JP5271454B2 (ja) * | 2010-09-01 | 2013-08-21 | 日本水産株式会社 | アルコール性障害緩和剤 |
US8691297B2 (en) | 2010-09-01 | 2014-04-08 | Nippon Suisan Kaisha, Ltd. | Alcoholic injury mitigating agent |
JP2012051865A (ja) * | 2010-09-03 | 2012-03-15 | Nippon Suisan Kaisha Ltd | 鎮静および睡眠促進剤 |
JP2014509339A (ja) * | 2011-02-11 | 2014-04-17 | テドク・エフアールディー・カンパニー・リミテッド | オキアミ油の製造方法およびこの方法で製造されたオキアミ油 |
CN103608022A (zh) * | 2011-05-31 | 2014-02-26 | 日本水产株式会社 | 脑功能改善剂 |
WO2012165586A1 (ja) * | 2011-05-31 | 2012-12-06 | 日本水産株式会社 | 脳機能改善剤 |
WO2013002404A1 (ja) * | 2011-06-29 | 2013-01-03 | 日本水産株式会社 | 恐怖記憶の軽減方法 |
CN103687603A (zh) * | 2011-06-29 | 2014-03-26 | 日本水产株式会社 | 恐怖记忆的减轻方法 |
JPWO2013002404A1 (ja) * | 2011-06-29 | 2015-04-30 | 日本水産株式会社 | 恐怖記憶の軽減方法 |
US9107891B2 (en) | 2011-06-29 | 2015-08-18 | Nippon Suisan Kaisha, Ltd. | Method for alleviating fear memory |
CN103687603B (zh) * | 2011-06-29 | 2016-11-30 | 日本水产株式会社 | 磷虾油在制备心理创伤后应激障碍的治疗或预防的制剂中的用途 |
JP2013053110A (ja) * | 2011-09-05 | 2013-03-21 | Teikyo Univ | 経口投与剤 |
JP2013053109A (ja) * | 2011-09-05 | 2013-03-21 | Teikyo Univ | リン脂質結合型dha増加剤 |
JP2013216654A (ja) * | 2012-04-05 | 2013-10-24 | Nippon Suisan Kaisha Ltd | 脳萎縮抑制剤 |
Also Published As
Publication number | Publication date |
---|---|
KR20110074973A (ko) | 2011-07-05 |
CA2738285A1 (en) | 2010-04-01 |
US8784921B2 (en) | 2014-07-22 |
CN104522293B (zh) | 2017-10-10 |
JPWO2010035749A1 (ja) | 2012-02-23 |
EP2335494A4 (en) | 2013-03-27 |
EP2332424A1 (en) | 2011-06-15 |
CA2738285C (en) | 2017-03-07 |
CN102202519B (zh) | 2014-12-17 |
US20110189760A1 (en) | 2011-08-04 |
EP2335494A1 (en) | 2011-06-22 |
JP5703022B2 (ja) | 2015-04-15 |
JPWO2010035750A1 (ja) | 2012-02-23 |
KR101650596B1 (ko) | 2016-08-23 |
EP2332424B1 (en) | 2014-06-18 |
JP5703021B2 (ja) | 2015-04-15 |
CN102196733A (zh) | 2011-09-21 |
KR20110073481A (ko) | 2011-06-29 |
US8568819B2 (en) | 2013-10-29 |
CA2738282A1 (en) | 2010-04-01 |
CA2738282C (en) | 2016-05-24 |
CN102196733B (zh) | 2014-11-26 |
WO2010035749A1 (ja) | 2010-04-01 |
CN104522293A (zh) | 2015-04-22 |
EP2332424A4 (en) | 2013-03-13 |
CN102202519A (zh) | 2011-09-28 |
US20110189374A1 (en) | 2011-08-04 |
KR20180010325A (ko) | 2018-01-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5703022B2 (ja) | 脂質の製造方法 | |
JP6308950B2 (ja) | 甲殻類を処理し、その低フッ化物/低トリメチルアミン産物を生成する方法 | |
JP4181305B2 (ja) | 海産および淡水産動物の組織から脂質を抽出する方法 | |
US20140031569A1 (en) | Process for the isolation of a phospholipid | |
CN102311868B (zh) | 一种无溶剂提取富含磷脂和中性油脂的磷虾油的方法 | |
JP2010022289A (ja) | ニンニクの脱臭方法、及びアリイン含有量の高い脱臭ニンニク食品素材、並びにこれを使用した食品 | |
US2503312A (en) | Simultaneous defatting and dehydrating of fatty substances | |
JP2004026767A (ja) | 魚介類由来のリン脂質の製造方法 | |
KR101022137B1 (ko) | 함초유의 제조방법 | |
JPH0145520B2 (ja) | ||
CA3178567A1 (en) | Method for producing fish oil | |
JPH0453895A (ja) | 天然抗酸化剤の製造法 | |
JPH07503840A (ja) | 低コレステロールのダイエット用卵全体製品又は卵黄製品の製造方法並びにそれらの製品の食品への2次加工方法 | |
JPH01294649A (ja) | スケトウタラ精巣よりドコサへキサエン酸およびエイコサペンタエン酸を高濃度で抽出する方法 | |
JP2002265975A (ja) | 高度不飽和脂肪酸含有油脂の製造方法 | |
Tzia et al. | 12 Fat and Oil Processing Technology | |
JP2022521181A (ja) | 高レベルの遊離脂肪酸を含むオキアミ抽出物から濃縮された治療用リン脂質組成物を製造する方法 | |
KR100718551B1 (ko) | 멸치 또는 그 가공물에 있어 농축 멸치육과 멸치유로분리하는 방법 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 200980142656.4 Country of ref document: CN |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 09816165 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2010530853 Country of ref document: JP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2009816165 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2738285 Country of ref document: CA |
|
ENP | Entry into the national phase |
Ref document number: 20117007028 Country of ref document: KR Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 13120842 Country of ref document: US |