EP0322425A1 - Procede pour preparer une composition d'huile - Google Patents

Procede pour preparer une composition d'huile

Info

Publication number
EP0322425A1
EP0322425A1 EP88903343A EP88903343A EP0322425A1 EP 0322425 A1 EP0322425 A1 EP 0322425A1 EP 88903343 A EP88903343 A EP 88903343A EP 88903343 A EP88903343 A EP 88903343A EP 0322425 A1 EP0322425 A1 EP 0322425A1
Authority
EP
European Patent Office
Prior art keywords
omega
fatty acids
species
acid
fat
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP88903343A
Other languages
German (de)
English (en)
Inventor
Tibor Farkas
Anikó NAGYN VANICSEK
László M RTON
László PELLE
Gábor TÖRÖK
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Teva Pharmaceutical Works PLC
Original Assignee
Biogal Gyogyszergyar Rt
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Biogal Gyogyszergyar Rt filed Critical Biogal Gyogyszergyar Rt
Publication of EP0322425A1 publication Critical patent/EP0322425A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B1/00—Production of fats or fatty oils from raw materials
    • C11B1/10—Production of fats or fatty oils from raw materials by extracting
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12—Fatty acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • 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
    • A61K35/60—Fish, e.g. seahorses; Fish eggs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • A61P9/08—Vasodilators for multiple indications
    • 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
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/007—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids using organic solvents
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
    • C11C1/025—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by saponification and release of fatty acids

Definitions

  • the present invention relates to the preparation of oil compositions with high omega-3 unsaturated fatty acids from Hypophthalmichthis and Abramis species.
  • fatty acids are precursors of a family of compounds metabolized in the organism, the said compounds having important regulation function. If the food lacks of a certain group of unsaturated fatty acids, thefunctional equilibrium of the regulating compounds thus obtained be come s unbalanced leading to serious consequence in the health.
  • the fatty acids occur in the organism in the form of phospholipids , triglycerides and free fatty acids . According to their origin and function they can be distributed in four main groups :
  • Characteristic and starting material of this group is the linoleic acid. They are present in plant tissues , in the first line in seeds.
  • the characteristic and starting material of this group is linolenic acid. They are synthetized by microorganisms living in the water and deposited in the tissues of fishes feeding on the said organisms. As human food they can be taken up only by eating fishes but get into the organism in very small quantities only. The importance thereof is proved by the fact that this small amount mostly occurs in the brain tissues. They are non-essential compounds but in the absence thereof regulation disturbances and illnesses might occur and the deficiency thereof indirectly and together with other factors may cause even death.
  • the fatty acids are labelled as X:Y omega Z/number of carbon atoms: number of double bonds and Z means the length of the saturated carbon chain after the last double bond including the terminal methyl group/.
  • the group of C 20 fatty acids is that of eicosaic acids including the 20:/ omega-6 arachidonic acid /AA/ and 20:5 omega-3 eicosa-pentaenoic acid /EPA/.
  • the group of C 22 fatty acids is that of docosaic acids including among others the 22:1 omega-9 erucidic acid and 22:6 omega-3 docosa-hexaenoic acid /DHA/.
  • C 20 eicosaic acids play an important role and the group of C 20 compounds thus obtained are named as eicosanoides.
  • Functional derivatives obtained therefrom are the thromboxanes formed by ring closure /Proc. Natl. Acad. Sci., 1975, Hamberg/ and the prostaglandines.
  • the latter group has already previously been known but only recently discovered that they are derived from tne eicosaic acid /Nature, 1976, Moncada/.
  • the leukotrienes are also obtained through additional metabolic routes /Proc. Natl. Acad. Sci. , 1979, Murphy/ and even nowdays further metabolites and functions have become known.
  • the biosynthetic route of eicosanoids is illustrated by Fig, 1.
  • the natural starting material thereof is the arachidonic acid /AA/ which can be found in the phospholipids.
  • this group is also named as "diene metabolites" .
  • the functions of the metabolites illustrated on Fig. 1 areas follows:
  • PGH 2 vasoconstrictor, A DP-releasing, blood platelet acviating.
  • the adhesion of active blood plateles increases and a hormone will be produced which stimulates the proliferation of vessel wall cells. They also promote the release of serotonin and the production of thromboxane .
  • PXA 2 aggregates blood platelets, promotes thrombus formation.
  • LTB 4 induces inflammations, stimulates the immune reactions.
  • TXB 2 and 6-keto-PGF 1 byproducts which are secreted from the organism.
  • the system of eicosanoides responses to the damaging influences such as penetration and deposit of foreign materials , vessel wall lesions, etc. with inflammation, allergic reactions, thickening of vessel wall and vasoconstnction, as well a d blood clogging at the area of lesion.
  • the basic principle of each regulation that the responses on the effect should be repressed in certain extent, otherwise the activated regulation system turns the conditions into the opposite, also non-desired direction.
  • the organism responses so that the eicosapentaenic acid /EPA/ and derivatives thereof are analogous substrates of the same enzyme systems. These molecules compete with the corresponding members of AA metabolites and push the former off the surface of the enzymes while their own metabolites are practically. ineffective.
  • the two starting materials and metabolites thereof differ from each other in the delta-17 double bound.
  • the metabolites of EPA origin are called as "triene" metabolites. Accordingly, the balance of organism depends on the equilibrium of the diene vs. triene metabolites /Nature 307, 165, 1984/.
  • PGI 3 substantially as vasodilating as PGI 2 .
  • the triene metabolites increase the cyclic AMP level which inhibits phospholipase A 2 and, accordingly, the formation of AA.
  • the 22:6 omega-3 docosahexaenic acid /DHA/ has an effect identical to that of EPA.
  • the omega-3 acids having lower carbon atom number are transformed into EPA in the organism by the so-called "elongation process".
  • the metabolic passway and metabolite functions are described e. g. in the following literatures: Proc. Natl. Acad. Sci., 76 , 944 /1979/; B. B. A., 875, 369 /1986/: New England j. of Med., 314 , 937 /1986/; Thrombosis Res., 42 , 99 /1986/: Nutr. Reviews, 44 , 205 /1986/.
  • the article of Aquaculture Hungarica 1, 35 /1978/ reports on examinations for the fatty acid content of Hypophthalmichthis species which widely bred in Hungary.
  • the article reports on the influence of feeding.
  • the EPA-content in the said species may amount to 8, 3 or even 9, 9 % of the total fat content.
  • the corresponding AA -values were found as 7 ,5 and 8,5 %, respectively.
  • the extensive fish consumption might cause pesticide poisoning as the said chemicals are deposited in fishes in the first line. For this reason, and to ensure a reproducible administration the production and sale of compositions containing omega-3 unsaturated fatty acids was first introduced in the USA. These are most frequently capsulated oils with a content of 20 to 50 % of omega-3 unsaturated fatty acids /EPA and DHA/.
  • the C 22 erucaic acid can be found in rape oil in greater quantity. Even nowdays great efforts are being made to improve rape free from erucaic acid [Lipids, 746 and 548 /1972 /].
  • compositions like PROMEGA, PROTOCHOL or O MEGA-3-EPA contain 55 to 86 % mixed ballast material beside the active material.
  • the present invention aim s to provide a solution to elimin ate the above harmful effects. Disclosure of invention
  • a preparation with high content of omega-3 unsaturated fatty acid and free from 20: 1 and 22: 1 fatty acids can be prepared by using intra-abdominal fat of wild or bred Hypophthalmichthis species: silver carp [H. molitry /Valucianne/] and big head carp [H. nolibis /Richardson/ ] and certain bream /Abramis/ species, preferably Abramis brama, respectively, as starting material.
  • the lipids are extracted therefrom with organic solvent, solvent mixture, hot water or steam and the lipid mixture thus obtained is enriched in fatty acid of higher unsaturation by forming lipid-urea complexes and separating the same.
  • the tissues of Hypophthalmichthis and Abramis species, respectively, are characterized by essentially not containing 20: 1 and 22: 1 fatty acids and by a relatively high EPA- and DHA-content.
  • the fat content of muscles is low /3 %/, i. e . about one tenth of that of the sea fishes listed hereabove but a substantial quantity of fat deposit can be found on the viscera which have previously been treated as debris.
  • the fatty tissue separated from the intestines and omentum besides a fat content of almost 100 %, surprisingly and preferably shows a very low AA-content.
  • the main part of fatty acids consists of saturated fatty acids and oleic acid, the amount of which may be decreased substantially by urea-complex forming and thus the active ingredient content /E PA, DHA and omega-3 fatty acid transformed to C 18 polyene EPA/ can be increased up to 60 %.
  • the characteristic lipid composition of the starting material ensures to obtain a composition with high active ingredient content and free of harmful material by using simple , one-step purification
  • compositions obtained according to the present invention serve for food completion and health care . As such , it is superior due to the high active ingredient content /EPA + DHA/ and preferably low AA-content thereof and is harmful as even traces of 20: 1 and 22: 1 acids cannot be found therein.
  • a further advantage of the process according to the present invention is that the lipid extraction is carried out on valueless waste material, the quantity of which is substantially less than that of the flesh or whole fish.
  • the crude product obtained can effectively be purified by a simple single step.
  • compositions prepared according to the present invention may be used, by mixing in the food or capsulated against vasoconstriction, artheriosclerosis, vascular obstruction, allergic dermatitis and for preventing tumorous methastases.
  • the compositions can also be used for adjusting the correct diet in case of the aforesaid illnesses.
  • the daily doses can vary between 0, 2 to 2,0 g, depending on the indication and duration of treatment.
  • Fig. 1 shows the biosynthetic route of eicosanoids.
  • FLg. 2 shows the biosynthetic routes starting from EPA .
  • Fig. 3 shows the fatty acid composition of the starting oil in Example 9.
  • Fig. 4 shows the analysis of the fatty acid mixture obtained in Example 9.
  • Example 1 In processing silver carp 3 years old /weighing 1,2 kg bred in pond/ the inner parts w ere removed and the thick fatty tissue deposited on the viscera was manually separated. The amount of tissue obtained from one animal averaged 135 g. Fro m the fat tissue and flesh each 1 g samples were taken and extracted three times with each 5 ml of petroleum ether so that the tissue was homogenized in the presence of 2 g of dry sodium sulfate with the first charge of solvent, the solid parts were filtered off, and suspended cm the filter twice with each 5 ml of peiroleum ether. The three solvent fractions were combined and distilled in vacuo until oily residue was obtained. T he oi) *as subjected to gas chromatography. The result obtained were compared with those obtained from the extract of carp flesh.
  • the fat from the abdominal cavity did not contain 20:1 and
  • Example 2 Processing of big head carp, 3 years old, weighing 2100 g.
  • the fatty acid composition of the fat tissue from the abdominal cavity of big head carp was similar to that of the silver carp, the fat composition of the flesh altered in a higher AA-content and the percentage of EPA- and DHA-content.
  • the weight of material to be extracted was again multiple.
  • mackerel though it constitutes a good source of EPA and DHA, the high 20:1 and 22:1 content of the product could be detected.
  • the emulsion thus obtained was allowed to stand for 3 hours, then the proteins forming the precipitate were removed by filtering on Whatman IPS paper and to the filtrate 400 ml of 0,2 M aqueous potassium chloride solution was added.
  • the system was allowed to separate into two layers and after completion of the separation the lower phase containing the lipids was separated and the upper phase discarded.
  • the chloroform solution was dried over dry sodium sulfate, filtered and the solvent was distilled off from the filtrate.
  • 83,2 g of colourless or slight yellow oil was obtained and the fatty acid composition was identical with that obtained according to example 1.
  • Example 4 100 g of fatty tissue obtained according to example 2 was extracted with 800 ml of petroleum ether by homogenizing in the presence of 200 g of dry sodium sulfate. The tissue residues and salts were filtered off, the precipitate was washed with 2 ⁇ 100 ml of petroleum ether and the washings were combined with the extract. The solvent was distilled off in vacuo from the lipid solution thus obtained, 91 g of slightly yellow oil was obtained, the fatty acid composition being identical with that of the product obtained in example 2.
  • fatty tissue was collected from the abdominal cavity.
  • the material was stored in plastic container filled with ice and transported to the place of extraction at the temperature of melting ice.
  • Example 8 From the fatty acids in the oil obtained according to any of examples 3, 4 and 5 methyl esters were formed by adding to the oil sodium meth ⁇ xide dissolved in half volume of methanol. The sodium methoxide added was in molar equivalent with the fatty acid content. The reaction mixture was allow ed to stand at room temperature for 10 to 16 hours and then a 10-fold volume of petroleum ether based on the fatty acids and water in an amount necessary for the separation of layers were added. The lower layer was discarded , the petroleum ether solution was washed with water and the solvent was distilled off. The oil thus obtained contained fatty add methyl esters.
  • Figures 3 and 4 show the urea purification of fatty acids obtained from fat tissues of silver carp by hot water extraction, saponification and liberation.
  • Fig. 3 shows the fatty acid composition of the starting oil.
  • Fig. 4 shows the analysis of the polyenerich fatty acid mixture obtained by adduct forming according to the present example.
  • deep freezing, or addition of antioxidants e. g . 0, 1 % of tokoferol or 0,05 % of butylated hydroxytoluene can be used.
  • the solvent extraction can be carried out e . g. in counter-current extractor while the aqueous extraction may be accomplished in autoclave by steaming the fat tissue .
  • the free fatty acids may also be liberated in. buffered aqueous medium by enzymatic decomposition, e. g. with lipase.
  • the urea complex forming can be performed by heating at 50 to 70 °C for 30 to 60 minutes. To precipitate the adduct, the system is cooled below 30 °C .
  • the fatty acids can also be extracted from the aqueous solution thereof with other fat solvents, e. g. n-hexane , benzene, ethylacetate, etc. Before distilling off the solvent, those containing water, e . g. ethyl acetate, should be dried with sodium sulfate, resin treatment, etc.
  • other fat solvents e. g. n-hexane , benzene, ethylacetate, etc.
  • those containing water, e . g. ethyl acetate should be dried with sodium sulfate, resin treatment, etc.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Epidemiology (AREA)
  • Cardiology (AREA)
  • Microbiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Immunology (AREA)
  • Polymers & Plastics (AREA)
  • Dermatology (AREA)
  • Urology & Nephrology (AREA)
  • Pulmonology (AREA)
  • Hematology (AREA)
  • Mycology (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Vascular Medicine (AREA)
  • Marine Sciences & Fisheries (AREA)
  • Diabetes (AREA)
  • Fats And Perfumes (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Meat, Egg Or Seafood Products (AREA)
  • Edible Oils And Fats (AREA)

Abstract

Procédé pour préparer des compositions d'huile à partir d'un groupe de poissons constitué des espèces Hypophthalmichthis et Abramis, lesdites compositions étant utiles pour compléter l'alimentation afin de prévenir les conséquences pathologiques de l'artériosclérose. Le procédé décrit utilise comme matière première les tissus gras provenant de la cavité abdominale des espèces précitées. Les compositions ainsi préparées présentent une teneur très élevée en acides gras oméga-3.
EP88903343A 1987-04-23 1988-04-22 Procede pour preparer une composition d'huile Withdrawn EP0322425A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
HU871757A HU203660B (en) 1987-04-23 1987-04-23 Improved process for producing food-additive composition rich in omega-3-unsaturated fatty acids
HU175787 1988-03-31

Publications (1)

Publication Number Publication Date
EP0322425A1 true EP0322425A1 (fr) 1989-07-05

Family

ID=10956039

Family Applications (1)

Application Number Title Priority Date Filing Date
EP88903343A Withdrawn EP0322425A1 (fr) 1987-04-23 1988-04-22 Procede pour preparer une composition d'huile

Country Status (10)

Country Link
EP (1) EP0322425A1 (fr)
JP (1) JPH01502345A (fr)
KR (1) KR890701718A (fr)
AU (1) AU1627188A (fr)
DK (1) DK709488D0 (fr)
FI (1) FI885929A7 (fr)
HU (1) HU203660B (fr)
MC (1) MC2012A1 (fr)
NO (1) NO885731L (fr)
WO (1) WO1988008444A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2218984B (en) * 1988-05-27 1992-09-23 Renafield Limited Process for preparing high-concentration mixtures of polyunsaturated fatty acids & their esters and their prophylactic or therapeutic uses
GB8819110D0 (en) * 1988-08-11 1988-09-14 Norsk Hydro As Antihypertensive drug & method for production
US6340705B1 (en) * 1999-09-10 2002-01-22 Monsanto Technology, Llc Use of α-linolenic acid metabolites for treatment or prevention of cancer
SE0202188D0 (sv) 2002-07-11 2002-07-11 Pronova Biocare As A process for decreasing environmental pollutants in an oil or a fat, a volatile fat or oil environmental pollutants decreasing working fluid, a health supplement, and an animal feed product
EP2295529B2 (fr) 2002-07-11 2022-05-18 Basf As Procédé de diminution des polluants environnementaux dans une huile ou une graisse et produit d'alimentation pour poissons
CN102031201B (zh) * 2010-11-03 2012-08-15 西安应化生物技术有限公司 一种共轭亚麻酸分子蒸馏纯化方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4377526A (en) * 1981-05-15 1983-03-22 Nippon Suisan Kaisha, Ltd. Method of purifying eicosapentaenoic acid and its esters

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8808444A1 *

Also Published As

Publication number Publication date
DK709488A (da) 1988-12-20
NO885731D0 (no) 1988-12-22
JPH01502345A (ja) 1989-08-17
AU1627188A (en) 1988-12-02
KR890701718A (ko) 1989-12-21
NO885731L (no) 1988-12-22
WO1988008444A1 (fr) 1988-11-03
MC2012A1 (fr) 1990-02-16
HUT46211A (en) 1988-10-28
DK709488D0 (da) 1988-12-20
HU203660B (en) 1991-09-30
FI885929L (fi) 1988-12-21
FI885929A7 (fi) 1988-12-21

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