EP2152094A2 - Desodorierung und stabilisierung von meeresölen - Google Patents

Desodorierung und stabilisierung von meeresölen

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Publication number
EP2152094A2
EP2152094A2 EP08758456A EP08758456A EP2152094A2 EP 2152094 A2 EP2152094 A2 EP 2152094A2 EP 08758456 A EP08758456 A EP 08758456A EP 08758456 A EP08758456 A EP 08758456A EP 2152094 A2 EP2152094 A2 EP 2152094A2
Authority
EP
European Patent Office
Prior art keywords
food
oil
marine oil
deodorized
marine
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Withdrawn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
EP08758456A
Other languages
English (en)
French (fr)
Inventor
Andreas Keller
Ingo Koschinski
Albert Lustenberger
Neil Macfarlane
Thomas Meierhans
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.)
DSM IP Assets BV
Original Assignee
DSM IP Assets BV
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
Priority claimed from EP07009539A external-priority patent/EP1992233A1/de
Application filed by DSM IP Assets BV filed Critical DSM IP Assets BV
Priority to EP08758456A priority Critical patent/EP2152094A2/de
Publication of EP2152094A2 publication Critical patent/EP2152094A2/de
Withdrawn legal-status Critical Current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
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
    • C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
    • 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
    • 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
    • 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
    • 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
    • A23L5/21—Removal of unwanted matter, e.g. deodorisation or detoxification by heating without chemical treatment, e.g. steam treatment, cooking
    • 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
    • C11B3/00—Refining fats or fatty oils
    • C11B3/12—Refining fats or fatty oils by distillation
    • C11B3/14—Refining fats or fatty oils by distillation with the use of indifferent gases or vapours, e.g. steam
    • 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
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants

Definitions

  • the present invention relates to a process for the deodorization and stabilization of marine oils and to the marine oils thus obtained.
  • Marine oils have attracted substantial interest as a source of polyunsaturated fatty acids (PUFAs), particularly eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) are of dietary significance, including PUFA esters, in the form of their naturally occurring glycerides as well as in the form of ethyl esters.
  • PUFA esters in the form of their naturally occurring glycerides as well as in the form of ethyl esters.
  • PUFA esters in the form of their naturally occurring glycerides as well as in the form of ethyl esters.
  • EP 340 635 A describes a process of treating oils, especially fish oils, containing EPA and DHA by vacuum steam distillation under mild conditions (between 30 0 C and 150°C, preferably 60-100 0 C, for 2-5 hours) to reduce low temperature boiling and less polar volatile _ .
  • flavour compounds and contacting said oil with an adsorbent, e.g., silica gel, to reduce high temperature boiling and more polar volatile flavor compounds.
  • an adsorbent e.g., silica gel
  • the thus purified oil is combined with a rosemary extract antioxidant.
  • rosemary extract antioxidant is characterized by rosemary extract taste and smell which renders it unsuitable for many food applications, especially in dairy products.
  • dairy applications such as yoghurts and milk drinks, which are particularly sensitive to smell, the development of unacceptable unpleasant smell and taste was observed on some occasions.
  • This procedure provides stabilized food grade marine oils with excellent smell and taste characteristics and a rancimat induction time value of 4.1 to 6.2 hours. The quality of these oils is so far the best obtainable and renders them suitable for various food applications including dairy products, e.g., milk and yoghurts.
  • US 4,996,072 discloses a method of deodorizing and/or reducing the cholesterol level of fats and oils, particularly fish oils or marine oils, by a multiple step process under vacuum which " compTises " Reatlng such oil to a temperature of about 400 - 550 0 F (204 - 288°C), flash vaporizing said heated oil yielding a par-treated oil liquid phase which oil is then thin- film stripped with 1 - 15% (by weight) counter-current steam at 1 - 7 mmHg.
  • a clean oil is obtained characterized by the bland flavour of clean fish oil, with reduced cholesterol content and at least 95% of the n-3 unsaturated fatty acid content of the starting material.
  • US 4,810,330 describes a specific embodiment of a continuous deodorizing process for relatively small charges of high boiling liquids such as fatty acids, edible oils, fats, glycerides and other high-boiling esters, particularly palm oil and other vegetable oils which in addition to the fatty acid glycerides contain about 5 wt.-% of light ends (free fatty acids, water, pigments, odorous and/or flavouring compounds), by contacting a falinf film of the liquid with a continuous stripping stem in a counter-current column.
  • high boiling liquids such as fatty acids, edible oils, fats, glycerides and other high-boiling esters, particularly palm oil and other vegetable oils which in addition to the fatty acid glycerides contain about 5 wt.-% of light ends (free fatty acids, water, pigments, odorous and/or flavouring compounds)
  • JP 2007 014263 A describes the purification of edible fats and oils of vegetable and animal _ _
  • the oil obtained has low acidity, low colour, good taste and stability and low trans fatty acid levels.
  • Through the superior distillation efficiency of structured packings it is possible to trim the deodorizer both for tocopherol removal or tocopherol retention simply by adjusting the stripping steam.
  • Superiority of thin-film stripping using packed columns to tray stripping systems on the one hand and of structured packings to random-dumped packings on the other hand in thin-film deodorization of edible seed oils had already been found by Stenberg et al. (INFORM, 7 (12), 1296 - 1304, Dec. 1996).
  • WO 2006/1185518 describes a semi-continuous or continuous method for deodorizing organic or inorganic fluids in a column having one or more trays by contacting the fluid with a sparging gas which can be water vapor, preferably introduced at the bottom level of the trays.
  • a sparging gas which can be water vapor, preferably introduced at the bottom level of the trays.
  • the Sulzer Company on their website offers plants comprising packed columns containing structured packings for the preparation of edible fat and for oil deodorization by removal of free fatty acids from vegetable oils at a very low vacuum. Sulzer also offers different kinds of structured packings of different materials useful in such columns.
  • the present invention therefore, relates to a process for the preparation of deodorized and stabilized food-grade marine oils (compositions) which process comprises submitting a marine oil to a counter-current steam distillation (CCSD) in a thin film column containing a structured packing, preferably in the presence of herbal extract deodorants, and, if desired, adding anti-oxidant(s), e.g., ascorbyl palmitate and/or tocopherol and/or citric acid.
  • CCSD counter-current steam distillation
  • anti-oxidant(s) e.g., ascorbyl palmitate and/or tocopherol and/or citric acid.
  • the term "marine oil in the presence of herbal extract deodorants” comprises marine oil containing herbal extract deodorants or herbal extracts and marine oils to which herbal extract _ _
  • the present invention also relates to the deodorized and stabilized food-grade marine oils (compositions) obtained or obtainable by this process, to their use as dietary or health supplements and for the manufacture of preparations such as food applications, fortified food (functional food) as well as to the dietary and health supplements and the food fortified with these marine oils themselves.
  • marine oil as used herein is to be interpreted broadly and comprises oils from marine organisms which include algae, plankton, fish, preferably cold water fish and seal, including genetically manipulated / transformed organisms, as well as parts or fractions and components of such marine oils containing at least one long-chain (LC) PUFA.
  • LC long-chain
  • marine oil comprises oils obtainable from any organism which oils may upon degradation give rise to the occurrence of aldehydes and ketones responsible for development of "fishy” or other unpleasant smell and taste.
  • Such organisms include animals, microorganisms (e.g., yeasts) and plants as well as parts of the foregoing, e.g., seeds.
  • polyunsaturated fatty acid relates to n-3, n-6 and n-9 (or omega-3, omega-6 and omega-9) fatty acids, preferably n-3 fatty acids, with at least two C-C double bonds and esters thereof with glycerol or alkanols, preferably lower alkanols such as ethanol.
  • LC n-6 PUFAs are linoleic acid (C18:2), ⁇ -linolenic acid (GLA, C18:3), dihomo- ⁇ -linolenic acid (DGLA, C20:3) and arachidonic acid (ARA, C20:4).
  • LC n-3 PUFAs are ⁇ -linolenic acid (C18:3), octadecatetraenoic acid (C18:4; 6, 9, 12, 15), eicosapentaenoic acid (EPA, C20:5; 5, 8, 11, 14, 17), docosapentaenoic acid (DPA, C22:5; 7, 10, 13, 16, 19) and docosahexaenoic acid (DHA, C22:6; 4, 7, 10, 13, 16, 19).
  • C18:3 ⁇ -linolenic acid
  • octadecatetraenoic acid C18:4; 6, 9, 12, 15
  • EPA eicosapentaenoic acid
  • DPA docosapentaenoic acid
  • DHA docosahexaenoic acid
  • EPA and DHA have attracted interest of the food industry during the last years and marine oils containing them in form of their glyceryl, or alkyl, e.g., methyl or ethyl, esters, particularly in concentrated form, are of preferred interest in connection with the present invention.
  • the PUFA glycerol esters - which can be natural or reconstituted - comprise mono-, di- and tri-glycerides, the latter being of particular interest.
  • Methyl or ethyl esters are obtained from marine oils by transesterification.
  • the marine oil or fraction thereof which is used as starting material in the process of the present invention may be an unrefined, a degummed, deacidified, neutralized, partly oxidized, partly refined, refined, bleached and/or deodorized marine oil to which a herbal _ _
  • extract deodorant has been added, e.g., rosemary or sage extract.
  • Preferred starting materials have undergone pre-refinement, such as adsorption on silica with or without carbon and/or short path distillation.
  • the amount of the herbal extract to be added before the CCSD depends on its quality. The chemical nature of the components responsible for the deodorizing power of the herbal extracts and the mechanism(s) of their action are not clear today. With amounts in the range of 0,1 - 0,4% (w/w) of deodorized rosemary or sage extract excellent results are obtainable. However, this range is not a limitation.
  • the deodorized and stabilized food-grade marine oils are characterized by a low number in the FAST indexTM, viz., below 2 or 1.5, preferably between 1 and 2; 1 and 1.5; 1 and 1.3; more preferably between 1 and 1.1 and most preferably by a number of 1.0.
  • the index correlates exactly with trained taste panels to give a scale for fishy-ness.
  • the acronym "FAST” stands for "Fatty Acid Smell and Taste”.
  • SPME solid phase micro extraction
  • the FAST indexTM has been calibrated with human taste panels such that a score of 1-7 reflects the range of taste sensitivity experienced by human subjects.
  • a score of 1 indicates a complete lack of fishy taste (i.e. "not"), a score of 2 "very slightly”, a score of 3 "slightly”, a score of 4 "middle”, a score of 5 “strong", a score of 6 " very strong", whereas a score of 7 indicates an extreme fishy taste.
  • the human taste sensation is saturated at a score of 7 or little above, the FAST indexTM can measure taste and smell molecules up to a score of several hundred.
  • a further embodiment of the present invention is the removal or reduction of these molecules to concentrations that the FAST index TM is 1.0 wherein it is to be understood that 1.0 is less than 1.1 but comprises 1.01.
  • alkanals penentanal - blue cheese; hexanal - cut grass; heptanal - chemical, unpleasant; octanal - chemical, plastic; nonanal - chemical, plastic
  • alkenals (2-hexenal - bitter; 2-heptenal - bitter; 2-octenal - nutty; 2-nonenal -chemical, unpleasant)
  • alkadienals (2,4-heptadienal - rancid; 2,4- nonadienal -rancid) and ketones (1-penten-3-one - chemical, plastic; 1-octen-3-one - mushroom; 3,5-octadien-2-one - metallic).
  • the stability of a marine oil is given by its Rancimat induction time (RIT) value.
  • This value represents the time interval in hours until the oil reaches the onset of rancidity.
  • the value is measured using a Rancimat RTM apparatus (Metrohm Ltd., CH- 9101 Herisau, Switzerland) at 100 0 C. From this value measured at high temperature the stability of the oil at lower temperatures, e.g., 2O 0 C or 10 0 C can be extrapolated.
  • the marine oils of the present invention are characterized by a rancimat stability at 100°C of more than 2, preferably more than 3.8, more preferably more than 5.2, 6 or 6.2 and most preferably in the range of 10.15 - 20 hours.
  • the marine oils of the present invention are further processed into powders, premixes, granulates, beadlets, supplement forms, tablets, pills, lotions, solutions or emulsions in accordance with known techniques.
  • compositions and preparations or formulations containing / on the basis of a marine oil of the present invention can further comprise organic carrier molecules common in food, animal feed, cosmetic or pharmaceutical formulations.
  • stabilizers/antioxi- dants are methods of the state of the art and in combination with the present invention are preferred embodiments of the invention.
  • Particular examples of stabilizers include ascorbic acid, ascorbyl palmitate, BHT 1 t-butyl-hydroquinone (TBHQ), rosemary extracts, e.g.,
  • the invention provides a breakthrough in industrial processes for the preparation of stabilized and deodorized marine oils.
  • amounts of more than 10 kg per hour can be achieved.
  • the yield of product is more than 100 kg per hour or even 1000 kg per hour which represent industrially meaningful quantities of marine oils or fractions of marine oils.
  • Preferred packaging sizes include samples of more than 4 kg, preferably of more than 19 kg, more preferably of more than 170 kg, and most preferably of more than 900 kg.
  • the contacting with steam can be done in a variety of ways.
  • the marine oil or fraction of a marine oil is added on top or upper part of the column and the steam is added at the bottom or lower part thus running the column in counter-current modus.
  • the column is operated as a continuous counter-current steam column and the process is a counter-current steam distillation (CCSD).
  • CCSD counter-current steam distillation
  • the thin film column containing a highly efficient structured packing is operated with an NTS (number of theoretical stages) of more than 10 1 preferably more than 50 and more preferably with about
  • the column has no physical plates at all, although it is currently believed that 1 physical plate will not reduce the advantages of the process of the invention and even 2 physical plates are acceptable.
  • the difference in pressure (pressure drop) between the top of the column and the bottom of the column has in some instances an influence on the composition that is produced. Therefore in a preferred embodiment of the invention the pressure drop between bottom and top of the column is less than 2mbar/m, preferably between 0.01 and 1 mbar/m and more preferably between 0.8 and 1.0 mbar/m.
  • the ratio between the marine oil and the steam provides for differences in the results of the process. It is currently preferred in some embodiments to operate the thin film column at a marine oil to steam ratio (w/w) between 1000 : 1 to 10 : 1 , preferably 500 :1 to 20 :1 , more preferably 200 :1 to 50 :1 , and most preferably 160 :1 to 70 :1. Actually, very good results are obtained with a ratio of 120 :1.8.
  • the current process provides for effective usage of raw materials. It has been observed that it can reduce the waste considerably. It is, of course, evident that the nature and quality of the raw material has an influence on the mass balance.
  • the mass balance of the marine oil i.e., the difference between before and after having been contacted with the steam, is less than 5% by weight.
  • the metric dimensions of the column have an impact on the economics of the process. It is preferable to use columns containing 0.5 to 20 m, preferably 1 to 12 m, more preferably 2 - 10 m and most preferably more than 7 m of active structured packings. It is an essential advantage of the present invention that the average contact time of the marine oil with the steam is relatively short and, consequently, the production time per unit of deodorized and stabilized marine oils in accordance with the present process is considerably shortened. -
  • the residence time of the liquid phase in the column is between 0.5 and 60 minutes, more preferably between 5 and 30 minutes, 2 and 20 minutes or 5 and 10 minutes. It is especially preferred to have a residence time of the gas phase in the column of between 0.5 and 10 seconds.
  • the invention does not only relate to the stabilization and deodorization of complete oils directly obtained from marine organisms but also to fractions of marine oils. It is apparent for the skilled person that there are various qualities of marine oils available as raw materials for this process which qualities are dependent on their age. Some may have already undergone one or more purification steps before they are processed according to the process of the present invention. Therefore, the starting or raw materials for the process of the present invention comprise unpurified, unrefined marine oils, degummed marine oils, deacidified marine oils, decolourized, partly and completely refined marine oils, neutralized marine oils, bleached marine oils, stabilized and/or deodorized marine oils and mixtures thereof. In the most preferred embodiment of the present process the raw materials have undergone adsorption on silica and contain already herbal extract deodorants or such herbal extract deodorants are added to them more or less immediately before submitting them to the present process.
  • the marine oil is a food oil and comprises polyunsaturated fatty acids in form of their glycerides, mainly triglycerides, naturally occurring or reconstituted.
  • the oil is fed and treated at a temperature of between 80 0 C and 250 0 C, preferably between 100°C and 230 0 C, more preferably between 180°C and 220°C.
  • the marine oil comprises polyunsaturated fatty acids in form of alkyl esters, preferably methyl or ethyl esters, and is fed and treated at a temperature of between 60 0 C and 200 0 C, preferably between 8O 0 C and 180 0 C, more preferably between 105°C and 150°C or between 120°C and 160°C.
  • the temperature of the steam is between 100 0 C and 29O 0 C 1 preferably between 140 0 C and 16O 0 C.
  • the thin film column is run under a pressure of between 0.1 and 10 hPa, preferably between 0.5 and 10 hPa and more preferably between 1 and 5 hPa .
  • a variety of additional routine process steps can be performed in connection with the execution of the process of the present invention.
  • One preferred step is degassing.
  • the process comprises degassing the marine oil, preferably before contacting it with the steam, to less than 1 ppm (by volume of the marine oil) of O 2 , preferably to less than 0,5 ppm.
  • Another special favourable measure is the evaporation of water. It is an improvement to evaporate the marine oil, preferably shortly before contact with the steam, to less than 50 ppm water (based on the weight of the marine oil), preferably to between 1 and 50 ppm of water.
  • the steam should be free of oxidizing components, e.g., O 2 . It has been found that steam from normal tap water is sufficient.
  • stabilizers e.g., antioxidants
  • additional deodorants e.g., herbal extracts
  • the marine oils of the present invention can advantageously replace PUFA-containing marine oils as such and in compositions and preparations or formulations, nutritional supplements and dietetic or fortified / functional food of the state of the art and on the marketplace in view of their advantageous organoleptic qualities and high stability.
  • the main market for deodorized and stabilized marine oils of the present invention is the food market. But it is also conceivable that there are interesting aspects of applications in the feed market.
  • the pet food market is also of interest in the context of the present invention. There are several applications contemplated in the cosmetic and pharmaceutical markets as well.
  • the compositions obtained according to the process of the invention can be used as health supplements and may be contained in food applications.
  • a special field of interest in pure and stable marine oils are dairy products, infant nutrition products or baby food products. Specific examples include beverages or cereals.
  • the compositions can be applied advantageously in milk, yoghurts and fruit juices which products are most sensitive to alterations in taste and smell in view of oxidation and degradation of marine oil components.
  • the present invention therefore, also relates to dietary or health supplements as well as fortified or functional food containing a deodorized and stabilized food-grade marine oil according to the present invention and a process-for-the-preparation-of-such-products- which are rich in n-3 PUFA(s).
  • the marine oils of the present invention which are rich in PUFAs, especially n-3 or ⁇ -3 PUFAs, particularly EPA and DHA, can be used advantageously for the production of a dietary, health or nutritional supplement or food fortified with n-3 fatty acids (functional food) in accordance with known methods, e.g., as described in US2007/0298079.
  • a fortified food is produced from an intermediate food product or its components by adding to it/them an amount of the marine oil in liquid form, as such or in form of an emulsion or a gel or in dry form, e.g., as powder, encapsulated in a matrix, containing the desired amount of n-3 fatty acid(s), normally 5 - 5000 mg, preferably at least 16 mg per serving of the food product, dispersing it by intensive mixing and, if desired, further processing and post-processing the substantially homogeneous blend thus obtained into the desired product.
  • the intermediate food product may be a juice (FC or NFC), e.g., citrus juices, non-citrus juices, dairy drinks, energy drinks, sports drinks, fortified/enhanced water drinks, soy drinks, fermented drinks, carbonated drinks, mixtures of such juices and drinks, yoghurt, oatmeal, cereals, cakes, snack bars, puddings, cheese and combinations thereof.
  • Further processing and post-processing is effected in accordance with methods well-known in the art and includes, e.g., pasteurization and cooling or filling into containers and packaging, respectively.
  • marine oils of the present invention can be used in a method for the manufacture of a liquid nutritional and refreshing preparations, e.g., orange juices, of the type described in WO 0147377 and EP 1 241 955, contents of which documents are incorporated by reference into the present specification.
  • Refreshing preparations as described therein and similar ones with respect to their qualitative and quantitative composition are exemplary of food applications of the marine oils of the present invention.
  • the present marine oils can also be part of and useful in the manufacture of dietetic compositions and food preparations comprising in addition to such oils at least one dietary fiber, such as resistant starch, fructooligosaccharides, oligofructosides and inulin in the context of reduced-fat diets with the purpose of weight reductions or weight control as described, e.g., US 2007/0010480, contents of which document is incorporated by reference into the present specification.
  • Dietetic compositions and food preparation thereof with the at least one n-3 fatty acid component is a present marine oil are also exemplary of dietary or health supplements and fortified/functional food of the present-invention.
  • examples of another specific embodiment of the present invention are nutritional supplements and functional food as described in WO 2006/117164, contents of which document is incorporated by reference into the present specification, wherein the n-3 fatty acid source is a marine oil of the present invention and which in addition comprise at least one nut oil and a flavor carrier, such as salad dressings.
  • citrus flavors are added to compensate for off-smell and -taste of marine oils and/or fractions of marine oils and/or PUFA's and PUFA (alkyl)esters and (tri)glycerides. While the final products obtainable in accordance with the present invention do not need such additives combinations with citrus flavors including citric acid are encompassed. In fact it is preferred not to add citrus flavors because they may interfere with the natural defense mechanism of the human body in the detection of spoiled food.
  • marine oils of the present invention can be used for the preparation of galenical formulations in the cosmetic and pharmaceutical industry in accordance with well-known methods.
  • a distilled ethyl-ester concentrate of a marine oil was subjected to a counter-current steam distillation in a thin film column (length: 8 m; diameter: 250 mm; stainless steel column with Sulzer BX gauze packing) under the following operation conditions: - -
  • Table 1 shows the oxidative stabilities of several commercially available n-3 PUFA ester products and of the product obtained according to Example 1
  • a partly refined marine oil was preheated in a thin film evaporator at 150 0 C and under reduced pressure of 30 mbar. Immediately thereafter the oil was subjected to a counter- - -
  • Table 2 gives FAST Index values of commercially available ester concentrates and reconstituted triglycerides and of samples obtained according to the present invention
  • TBHQ has long been known to be a powerful anti-oxidant. Unexpectedly we have found it to be a strong synergist with rosemary oil.
  • Ropufa® food oil containing 0.2% rosemary extract, 200 ppm ascorbyl palmitate and 1000 ppm mixed tocopherols has a Rancimat
  • Vitamin A max. 100 IU / ml
  • Vitamin D3 max. 50 IU / ml
  • Silika was added and agitation was started.
  • the pressure in the vessel was reduced to 40 hPa.
  • the vessel content was heated to 70 0 C. Agitation, temperature and pressure were maintained for 2 hours. Then the pressure was set to normal and 2% of activated carbon were added.
  • the pressure in the vessel was again reduced to 40 hPa. Agitation, a temperature of 7O 0 C and pressure were maintained for another 3 hours.
  • the vessel content was then cooled down to 40°C and filtrated first over a 10 micro Bag Filter followed by a 1 micro candle filter. To half of the filtered oil 2000 ppm of Herbalox were added.
  • PUFA oil was deodorized by a continuous counter current steam distillation (CCSD). Before the oil was fed into the deodorizer column the oil was degassed in a degassing unit at a temperature of 14O 0 C and a pressure of 40 hPa. After degassing the oil was further preheated in a heat exchanger to a temperature of 21O 0 C and then fed to the top of the deodorizing column.
  • the column of the deodorizer had an inner diameter of 50 mm and was equipped with a structured packing (type K ⁇ hni Rombopak S6M). The length of the struc- tured packing in the column was 4 m. Below the packing steam from a standard steam generation unit was continuously fed into the column.
  • the pressure of the steam was about 4 bar (4000 hPa) and the temperature approx. 144 0 C.
  • a very low vacuum was maintained by a 3-stage vacuum pump unit.
  • a pressure of 2 hPa was adjusted.
  • the mass flown of the oil amounted to 11 kg/h and the mass flow of the steam amounted to 0.1 kg/h.
  • the deodorized oil was cooled down to 80 0 C and finally three different antioxidants were added (tocopherol: 1000 ppm; ascorbyl palmitate: 250 ppm; citric acid: 25 ppm).
  • a sensory test provides the most useful information because it relates to the consumer acceptance of the food based on smell and taste.
  • the method is very sensitive and provides information on flavour stability.
  • Example 3 In analogy to the method described in Example 3 a transesterified marine fish oil from Ocean Nutrition, Canada (ONC) 1 was deodorized.
  • the EE75 fish oil ethyl ester from ONC had the following specification:

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PCT/EP2008/003782 WO2008138575A2 (en) 2007-05-11 2008-05-09 Deodorization and stabilization of marine oils
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CA2718525C (en) 2008-03-17 2016-05-24 Lipid Nutrition B.V. Process for refining a triglyceride oil
CN102461677B (zh) * 2010-11-19 2014-06-18 嘉里特种油脂（上海）有限公司 一种提高长链多不饱和脂肪酸稳定性的组合物及其用途
JP5858712B2 (ja) * 2011-09-30 2016-02-10 日清オイリオグループ株式会社 薄膜蒸発処理油脂の製造方法
PL2773216T3 (pl) 2011-11-01 2021-05-04 Dsm Ip Assets B.V. Stabilny oksydacyjnie olej zawierający wielonienasycone kwasy tłuszczowe
CN104507324A (zh) * 2012-07-31 2015-04-08 帝斯曼营养产品股份公司 使用绿茶提取物抗氧化剂精制油
JP6166983B2 (ja) * 2013-08-23 2017-07-19 花王株式会社 精製油脂の製造方法
PL3077489T3 (pl) 2013-12-04 2021-11-08 Nippon Suisan Kaisha, Ltd. Olej drobnoustrojowy zawierający kwas dihomo-gamma-linolenowy i biomasa drobnoustrojowa zawierająca kwas dihomo-gamma-linolenowy
JP6226089B2 (ja) * 2015-04-27 2017-11-08 不二製油株式会社 長鎖多価不飽和脂肪酸含有油脂の製造方法
AU2019395263B2 (en) 2018-12-14 2025-10-30 Dsm Ip Assets B.V. Polyunsaturated fatty acid containing food ingredient with enhanced palatabilty and method for manufacturing the same
CN113528235A (zh) * 2020-04-22 2021-10-22 华中农业大学 一种食用油的乙醇蒸汽蒸馏的脱臭工艺
EP4183462A1 (de) 2021-11-23 2023-05-24 TotalEnergies OneTech Verfahren zur desodorierung von regenerierten schmierölen mit überkritischem co2
JP7737518B2 (ja) * 2023-12-25 2025-09-10 マルハニチロ株式会社 脂質組成物

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JP2014128273A (ja) 2014-07-10
JP2010526896A (ja) 2010-08-05
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CN105029138A (zh) 2015-11-11
CN101677600A (zh) 2010-03-24

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