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WO2009132463A1 - Nouveau procédé de désodorisation et amélioration organoleptique d'extraits d'huile d'animal marin - Google Patents

Nouveau procédé de désodorisation et amélioration organoleptique d'extraits d'huile d'animal marin Download PDF

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Publication number
WO2009132463A1
WO2009132463A1 PCT/CA2009/000600 CA2009000600W WO2009132463A1 WO 2009132463 A1 WO2009132463 A1 WO 2009132463A1 CA 2009000600 W CA2009000600 W CA 2009000600W WO 2009132463 A1 WO2009132463 A1 WO 2009132463A1
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Prior art keywords
oil
marine
deodorization
food composition
krill
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PCT/CA2009/000600
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English (en)
Inventor
Tina Sampalis
Wael Massrieh
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Neptune Technologies and Bioressources Inc
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Neptune Technologies and Bioressources Inc
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Publication of WO2009132463A1 publication Critical patent/WO2009132463A1/fr
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    • 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
    • A61K35/618—Molluscs, e.g. fresh-water molluscs, oysters, clams, squids, octopus, cuttlefish, snails or slugs
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/52—Adding ingredients
    • 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
    • A23L33/135—Bacteria or derivatives thereof, e.g. probiotics
    • 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
    • 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
    • A23L5/23—Removal of unwanted matter, e.g. deodorisation or detoxification by extraction with solvents
    • 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
    • A23L5/27—Removal of unwanted matter, e.g. deodorisation or detoxification by chemical treatment, by adsorption or by absorption
    • A23L5/273—Removal of unwanted matter, e.g. deodorisation or detoxification by chemical treatment, by adsorption or by absorption using adsorption or absorption agents, resins, synthetic polymers, or ion exchangers
    • 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
    • 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
    • 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

Definitions

  • the present invention relates to a process for deodorizing fish or marine oil, and to the now acceptable use of such deodorized fish or marine oil in the food industry.
  • KhII is the common name for small, shrimp-like crustaceans that swarm in dense shoals, especially in Antarctic waters. It is one of the most important food sources for fish, some kind of birds and especially for whales as being an important source of protein.
  • Krill is also a good source of omega-3 fatty acids, which are well known for their health benefits.
  • krill and/or marine oil may be used for the treatment of autoimmune murine lupus and other autoimmune diseases and can also be used for treating cardiovascular diseases.
  • the krill and/or marine oil used for these treatments has only conserved its omega-3 fatty acid as active ingredient, which is a very small part of all the active ingredients of the krill and/or marine oil itself. This fact reduces the potential of the krill and/or marine oil as a treatment for these diseases.
  • United States Patent No. 5,434,183 describes a phospholipid emulsion derived from marine and/or synthetic origin comprising polyunsaturated fatty acids and having anti-inflammatory and immunosuppressive effects and which promotes normal brain or retinal development and function. US 5,434,183 does not disclose the presence of antioxidants or nervonic acid (a mono-unsaturated fatty acid) in the composition.
  • Japanese patent application No 2215351 discloses a method for extracting and purifying phospholipids from fresh krill. Krill is lyophilized and then extracted with ethanol to produce an extract which is fractionated by absorption column chromatography to produce high purity phosphatidylcholine and phosphatidyl ethanolamine. There is no disclosure of a phospholipid extract comprising an antioxidant or nervonic acid.
  • Krill is subjected to autolysis caused by endogenous proteases and lipases, autolytic enzymes that cause oxidation and disintegration of krill proteins and fat.
  • Autolysis for the purpose of preserving the krill proteins in order to increase the yield of krill meal preparation is also responsible for the unpleasant odor and taste of krill and/or marine extracts caused by a rapid oxidation and hydrolysis of the krill lipids forming a high amount of free fatty acids, lysophospholipids and volatile compounds which in turn reduce the stability of krill extracts.
  • Various extraction/deodorization methods developed for fish oil have been tested on krill oil, but none of them reported to be promising. Some method removed desirable components from the oil that would need to be artificially added back after the process. Some other method clearly changed the nature of the oil, changing the color of the oil from orange/red to black, with a burnt smell.
  • DMS dimethyl-sulfide
  • volatile amines Frozen krill contains 50- 3700 ng/g of DMS, more in the cephalothorax than in telson. DMS evokes a flavor specific to crustaceans when its concentration is below about 100 ng/g. The aroma becomes unpleasant when it exceeds the concentration of 1 ⁇ g/g, and it becomes offensive when it exceeds several ⁇ g/g. DMS is enzymatically formed from dimethyl-/?-propiocetine in phytoplanktons which serve as food for krill.
  • Trimethylamine comes from trimethylamineoxide (Tokunaga et al., 1977, Nippon Suisan Gakkai shi, 43: 1209-1217; Yamanishi, 1978, "Comprehensive studies on the effective utilization of krill resources in Antarctic Ocean,” Science and Technology Agency, Japan, pp. 71-75).
  • a process for deodorization of marine extracted oil comprising the steps of: washing said marine extracted oil with a strong acid; rinsing the marine extracted oil obtained with water; and optionally treating the marine oil obtained with activated carbon to remove amine groups responsible in part for odours; and/or distilling under vacuum the marine oil.
  • the strong acid is preferably selected from the group consisting of HCIO 4 , HI, HBr, HCI, H 2 SO 4 , HNO 3 , HCIO 3 , HBrO 3 , HBrO 4 , HIO 3 , and HIO 4 .
  • the most preferred strong acid is however HCI.
  • a process for deodorization of marine extracted oil comprising the steps of washing said marine extracted oil with a water-soluble salt; and washing the marine oil treated with water.
  • the water-soluble salt is preferably selected from the group consisting of NaCI, CaCI 2 , KCI, NaF, NaBr, NaI, KBr, Kl, KF, CaF 2 , CaBr 2 , and CaI 2 .
  • the most preferred salt is NaCI, for its relative cheap price and ease of availability.
  • a process for deodorization of marine extracted oil comprising the steps of eluting marine oil on an ammonia removing ion exchange resin; and optionally treating the marine oil obtained with activated carbon to remove amine groups responsible in part for odors; and/or distilling under vacuum the marine oil.
  • a food composition comprising: a masked and/or deodorized marine oil; and an acceptable carrier.
  • a food composition as defined herein for the treatment and/or prevention of diseases selected from the group consisting of cardiovascular diseases, plaque reduction, arthritis, diabetes, premenstrual syndrome, psychiatric diseases, learning and developmental disorders and neurodegenerative diseases.
  • a process for extracting marine oil from a marine or aquatic biomass comprising the steps of: treating said marine organism with an enzymatic cocktail for preventing enzymatic autolysis, and blanching the marine organism so treated in boiling water, wherein steps are effected in a process for extracting oil either as preliminary steps before oil extraction.
  • the present invention provides a food composition or product comprising a multi-therapeutic oil extract, preferably free of protein.
  • the food composition comprises a lipid extract that may be extracted from a variety of marine or aquatic biomass sources.
  • Preferred sources of the oil extract are crustaceans, in particular, zooplankton.
  • mollusc and fish in particular squid.
  • the lipid can be extracted from at least one marine and/or aquatic biomass source, preferably two marine or aquatic biomass sources.
  • the food product can be dairy, beverage, cereal, confectionary, fruit nuggets, biscuit, protein bars among others.
  • a particularly preferred zooplankton is krill.
  • Krill can be found in any marine environment around the world. For example, the Antarctic Ocean (where the krill is Euphasia superba), the Pacific Ocean (where the krill is Euphasia pacifia), the Atlantic Ocean and the Indian Ocean all contain krill habitats.
  • Autolysis of the krill and/or marine biomass starts within the first 60 minutes and more accurately within the first 30 minutes after the biomass exits the water.
  • krill and/or marine biomass must be treated within the first 60 minutes, preferably 30 minutes and preferably within 15 minutes from exiting the water or during its exit from water.
  • Krill is treated with proteolytic enzyme preparations containing among others papain and/or bromelain. This allows to degrade enzymes responsible for the autolysis of the krill and/or marine biomass. As such, any proteolitic enzyme or cocktail of same that can prevent autolysis will be acceptable.
  • Krill is then cooked in a continuous cooker in which the raw material takes 5 minutes to pass through hot water at 9O 0 C to deactivate the enzymes in the hepatopancreas. This step allow to further reduce or prevent autolysis, allows to remove any volatiles compounds therein, and by deactivating the enzymes in the hepatopancreas, it also prevents the formation of lysophospholipid. Then the material is frozen and stored.
  • the so called boiled krill is frozen immediately after boiling by means of a contact plate freezer at -4O 0 C, preferably at -6O 0 C and better at -8O 0 C. The key point of this procedure is to freeze and store the material below -2O 0 C, as rapidly as possible, and preferably within the first 60 minutes.
  • Undesirable odours and taste of marine/krill oils can be removed or further removed by washing with HCI, preferably dilute 0.1 N HCI, and/or NaCI 1 preferably from 0.1-1 M, (more preferably at 0.1 mM or 0.5mM or 0.75mM), and if desired, followed by activated carbon treatment and vacuum distillation.
  • the wash can also be followed by a second wash with water, preferably distilled water.
  • the wash is preferably done with one part NaCI (1 OmM - 100OmM and preferred washing with 10OmM or 50OmM, or 75OmM and further preferred with 10OmM) for one part oil followed by a second wash with one or two parts water for one part oil.
  • the NaCI or HCI wash can be replaced by a run down of the extracted oil on Ammonia Removing Ion Exchange Resin. These additional steps completely eliminate or remove DMS and odor-causing amines such as trimethylamine (TMA) from the extract. No appreciable weight loss or color loss occurs in the oil following this treatment. After the deodorization process, a slightly fruity odour appears indicating a distinct decrease in the extract odour and its improvement in palatability. Appearance of a slightly fruity odour originates from the reduced carbonyl and TMA like compounds in the oil. Table 2 describes the improved stability indexes of the marine extract after complete treatment (inhibition of autolysis and elimination of volatiles and amines.
  • Table 3 describes the improved organoleptic indexes as measured by Gas chromatography mass spectrometry olphactory (GC-MS-O). The lower the percent of ash, protein and carbohydrates (protein degradation materials), the better the odour of the material tested.
  • the stable, deodorized oil extracts disclosed herein are capable of being used in food product compositions at high concentrations without imparting an unpleasant odour to such compositions.
  • compositions of the present formulation may be prepared by a process involving the steps of: admixing a deodorized and/or masked extracted oil with the given botanical formulation, aging the mixture for a given period of time; and admixing all other ingredient and other adjuvants and the aged mixture. Aging the mixture is only done to test the stability of the extract and it involves keeping the extract at extreme high, low and normal room and refrigerator temperature for 3 months.
  • An alternative process for the preparation of compositions in accordance with the present disclosure involves the step of: admixing deodorized or masked oil and at least one botanical extract.
  • the extracted oil described herein is one rich in phospholipids.
  • the phospholipids containing extracted oil is preferably a product of initial processing of the biomass by supercritical extraction (see Yamaguchi et a/., J. Agric. Food Chem., 34: 904-907, 1986) and/or by a process as described in PCT publication number WO 03/011873, the disclosure of which is incorporated herein by reference.
  • the phospholipids contained in the original starting material are extracted from the biomass meat and/or grease.
  • the deodorized oil as described herein has a very high natural stability with a peroxide value of zero or approaching zero and a good Oil Stability Index of less than about 0.2 Meq/kg after 20 or more hours.
  • Extraction of the oil and phospholipids composition from the biomass may generally be carried out by a method similar, but not restricted to, to the one described in PCT publication number WO 00/23546, the disclosure of which is incorporated herein by reference.
  • the extraction may generally be carried out by one or successive acetone treatments or acetone and alcohol treatments.
  • the deodorization process described herein can be carried out on any marine oil, including Krill oil, whether it be on freshly extracted oil or on oil that has been extracted before and bottled or stored for a while.
  • the oil tested (the original or raw material) is a krill oil as obtained commercially through Mercola.com (the authorized distributor of the Neptune Krill Oil, for Neptune Technologies & Bioressources Inc., the Applicant). When other oils are being treated herein, their nature will be specifically mentioned.
  • the preferred treatment involves the use of >60% acetone in the first extraction followed by extraction with a mixture of organic solvents at 65-95%/45-50% preferably acetone, ethyl acetate/ethanol mixture.
  • the most preferred extraction solvent system is 100% acetone in the first extraction followed with a 95%/5% ethyl acetate/ethanol mixture.
  • other ketones can also be used in combination with or in place of acetone.
  • the above extraction can be made directly on krill or other marine material, but is preferably performed following the enzymatic treatment with a cocktail of proteolitic enzymes and then boiled and cooled down or frozen, as described hereinabove.
  • the alcohol can be other than ethanol, e.g., isopropanol or t- butanol.
  • the acetate may also vary. Further, the ratio of alcohol to acetate may vary widely from 100:0 to 0:100. The procedure produces one or two successive lipid fractions and a dry residue enriched in protein, including active enzymes.
  • the phospholipids and oil extract disclosed herein may be used with or without other additives. Preferably, no other additives are used. However, if other additives are used, nutraceutical formulations may be made by methods known in the art. For example, the compositions of the present invention may be formulated in a conventional manner using one or more nutraceutically acceptable carriers.
  • the food or nutraceutical composition may be formulated for administration utilising a suitable route.
  • the nutraceutical composition may be formulated for oral, intravenous, intramuscular, intrarectal, transdermal, sublingual or subcutaneous administration. An oral route is preferred.
  • the nutraceutical composition may be formulated as a food additive, tablet, capsule, caplet, lozenge, syrup, suspension, emulsion or the like, all within the skill of a person knowledgeable in the art, having in hand the method for reducing the smell/taste of krill oil, or any fish oil.
  • the nutraceutically acceptable carrier may constitute from approximately 1% to 50% by weight, preferably approximately 10% to 30% by weight, based on the total weight of the active composition.
  • the nutraceutically acceptable composition may include additional carriers or excipients, lubricants, fillers, buffers, antibacterials, bulking agents, plasticisers, binding agents, colourants, anti-oxidants and stabilizing agents.
  • Suitable fillers or excipients may be selected from the group consisting of talc, titanium dioxide, starch, cornstarch, modified cornstarch, kaolin, cellulose (microcrystalline or powdered) and mixtures thereof.
  • Suitable binding agents include polyvinyl pyrrolidine, hydroxypropyl cellulose and hydroxypropyl methyl cellulose and mixtures thereof.
  • Suitable solution vehicles include, but are not limited to, ethanol, water, propylene glycol, butylene glycol, acetone, or other pharmaceutically acceptable vehicle.
  • the oil and phospholipids extract are masked and/or deodorized.
  • Refined marine oils have been known to be initially free from an off flavour/odour taste and smell of fish, but that reversion through oxidation occurs rapidly.
  • Various companies have conducted numerous experiments to deodorize and stabilize marine oils using chemicals and physical methods with final addition of ⁇ -tocopherol or mixed tocopherols at various concentrations. All those additions have resulted only in a short term improvement in odor/flavor and stability.
  • Stable, deodorized oils may be prepared by removing the cause of bad odour or by adding an amount of a deodorizing agent or a combination thereof, effective enough to substantially reduce and stop further formation of mal odour/flavour.
  • This objective is achieved for example by washing (1 :1 ) with dilute 0.1 N HCI followed preferably by activated carbon treatment and vacuum distillation.
  • the wash can also be done with one part NaCI to one part oil followed by a second wash with two parts water, preferably distilled water.
  • the oil can be run down on an ammonia removing ion exchange resin.
  • Appearance of a slightly fruity odour originates from the reduced carbonyl and TMA like compounds in the oil.
  • Other acid such as H 2 SO 4 have been tested and have showed similar efficacy with respect to the deodorization process, in eliminate or remove DMS and odour-causing amines such as trimethylamine (TMA) from the extract.
  • TMA trimethylamine
  • other salts other than NaCI
  • calcium salts have been tested and have showed suitable for use in the deodorization process described herein.
  • Table 4 below reports data showing the odor/taste improvement in the krill oil.
  • SO1C1 Obtained from Krill that has not been boiled during the extraction process to inactivate degradation enzymes that may be present in the krill extract, but the sample oil of which has not been washed, but has been heated to 95°C as previously described to evaporate volatile agents therefrom
  • the botanical formula is able to halt the oil from further development of odour caused by degradation or oxidation.
  • the deodorization or masking of this type can be carried out in a simple and affordable manner by the method described herein.
  • the deodorization and masking of the oil using the botanical formula renders a unique flavour that made it possible to incorporate the oil in, for example, ice creams, yoghurt, smoothies and other food products.
  • An extracted and deodorized oil, as an active nutraceutical ingredient has been developed.
  • the botanical formula does not adversely affect the activity of the oil as a whole or its individual components.
  • the present formulation does not substantially adversely affect the structure and/or function of the oil components.
  • additional acceptable adjuvant may be added to the composition of the present formulations.
  • Botanical extracts and oils were formulated and mixed with the extracted oil.
  • Examples of botanical extracts are dried thyme leaf total extract (1 :5), thyme leaf oil (10% linalool, 35% thymol, 20% carvacrol), lemongrass leaf oil, lime oil and vanilla beans total extract.
  • the total microbial level in deodorized oil was determined using the method described by the Food and Drug Administration (FDA). It is necessary that the total plate count should be brought down to zero or a minimum acceptable level of less than 10 CFU/g. Methods that can be used for the total plate, yeasts and mould counts are based on 3M & MFHPB-34 microbiology, which is certified to ISO 9001 for design and manufacturing of food and ingredients.
  • Total plate count CFU/g 3M & MFHPB-33; Yeast and Mould 3M & MFHPB-32; and Conforms 3M & MFHPB-34.
  • vanilla beans total extract 3.1 ml vanilla beans total extract; and 2.0 grams of thyme total extract.
  • Yoghurt strawberry flavored
  • deodorized krill oil 100 g. of Yoghurt (strawberry flavored) containing 500 mg of deodorized krill oil
  • the resulting deodorized krill oil was more stable for a longer period of time, compared to untreated krill oil.
  • the yoghurt matrix did not in any way modify the stability of the krill oil.
  • follow-ups on the omega-3 fatty acids, phospholipids, lipid classes, such as triglycerides, phospholipids and free fatty acids, and astaxanthine pigments parameters revealed that these parameters remained stable throughout the entire study, i.e. throughout 55 days.
  • the deodorization process does allow for a marked improvement in the removal of the fishy odours and flavour in krill oil, such that krill oil can now be more widely commercially used, especially in the food industry.
  • krill oil can now be utilized in either yoghurt or energy bars ("bars", “food bars” or “functional food bars”).
  • bars "food bars” or “functional food bars”
  • omega-3 including EPA and DHA
  • Marine phospholipids such as krill oil, represent only a fraction of the total phospholipid that may be found in the fat of these bars. Since they only represent a fraction of it, no evidence was observed of any decrease in the marine phospholipid concentration over time, i.e. either due to degradation or other processes.
  • the acid indicator remained stable, which is a very good indicator of the stability of the phosphatidylcholine present in the phospholipids in the bars, thereby evidencing the stability of the whole oil.
  • the carotenoids along with vitamin A are the compounds most susceptible to degradation, and are the first one to degrade in any marine oil that has not been treated.
  • the concentration of the carotenoids monitored remained stable over time in these bars and all during the stability study, these bars maintained a very pleasant odour of cranberries and oranges.
  • krill oil as now deodorized with the process of the present invention can be incorporated into bars and can remain very stable in these bars for a period of more than 59 days at room temperature (23 0 C).
  • the oil can be directly mixed with the herbal formula, if desired.
  • This can be conducted under lab conditions or in a continuous system where more than 1 ton can be mixed using batch to batch operations.
  • the operation temperature can range from 35 0 C to 60 0 C to ease the mixing of the product for about 15 to 30 minutes by continuous steering.
  • the time of mixing can be longer, depending on the volume of the starting oil and temperature. The higher the temperature (above room temperature) the faster the mixing process is.
  • the deodorized oil manufactured in accordance with the processes described herein to remove or mask off odour/flavour is useful for direct incorporation into foodstuffs such as yoghurt, mayonnaise, smoothies, margarines, spreads, ice creams, peanut butter or any type of butter that is used as spread and the like.
  • a deodorized marine oil and composition containing same for the treatment and/or prevention of diseases for which marine and especially krill oil has already been recognized to be useful for.
  • diseases include for example cardiovascular diseases, arthritis, diabetes, premenstrual syndrome and central and peripheral nervous system.
  • Such composition reduces plaque formation, low-density lipoprotein (LDL) and triglyceride (TG), and increases high-density lipoprotein (HDL).
  • LDL low-density lipoprotein
  • TG triglyceride
  • HDL high-density lipoprotein
  • the composition comprises a therapeutically effective amount of krill and/or marine oil in association with a nutraceutically acceptable carrier or excipient.
  • the functions of a composition rich in phospholipids are multiple and different.
  • the membranes of brain cells depend on phospholipids as part of their structure. Phospholipids are required for the production of neurotransmitters. Without adequate levels of acetylcholine, the brain cannot store or retrieve information efficiently. Lower choline levels in the brain are an underlying factor for age-related cognitive disorders. Women treated with phospholipids functionalizing long chain polyunsaturated fatty acids have been shown to improve hormonal related physical and emotional symptoms. Patients submitted to increased choline uptake show significant improvement in their ability to recall information and perform on memory retention tests, suggesting a causal relationship between poor choline status and cognition.
  • Dementia is the deterioration of mental function, particularly affecting memory, concentration, and judgment.
  • a frequent cause of dementia is Alzheimer's disease.
  • the first double-blind trial of phospholipids for memory and learning of a phospholipds-treated group was significantly improved over a placebo group, as well as certain emotional and behavior components of Alzheimer's disease.
  • Supplements of phospholipids have also shown impressive results in older populations with memory impairment unrelated to Alzheimer's disease.
  • the memory function of men and women initially averaged that of a typical 64 years old. After taking phospholipids supplements, the average memory function was 52 years old (a mental gain of 12 years; Crook et a/., 1991 , Neurology, 41 : 644-649).
  • KO before or after deodorization processing and/or accelerated aging were sealed ( ⁇ 1 .0 g) in 6 ml size headspace vials fitted with Teflon-faced silicone septa crimp closures. Samples were matrix-spiked with 10 pg of toluene-ds to serve as internal standard and the vials were incubated at 100 0 C for 30 minutes. Following incubation, 1.0 ml of headspace vapor were withdrawn and injected into the GC-MS for analysis using a pre-heated gas-tight syringe equipped with an on/off valve.
  • the KO before or after deodorization processing and/or accelerated aging were weighed ( ⁇ 1 g) and then rapidly sealed into the purge & trap apparatus (SIS Liquid Sample Purge & Trap System). The samples were heated to 100 0 C and purged with nitrogen at a rate of 50 ml/min. for a total of 30 minutes. The volatile out-gas products from the samples were trapped and concentrated on adsorbent cartridges containing Tenax-TA. Before analysis the samples were matrix-spiked with internal standards (-10.0 PPM each of d-8 toluene & d-8 naphthalene) to facilitate quantification.
  • internal standards -10.0 PPM each of d-8 toluene & d-8 naphthalene
  • the charged adsorbent traps were then connected to the Short Path Thermal Desorption system and thermally desorbed directly into the GC-MS system for final analysis.
  • the thermal desorption conditions were 250 0 C for 5 minutes.
  • the resulting P&T-TD-GC-MS chromatograms were then subjected to a thorough scan-by-scan search of the data to identify all semi-volatile flavor components and especially those with potential for imparting "fishy" flavor.
  • TMA trimethylamine
  • Another class of volatile compound present are called Maillard reaction products (Non- Enzymatic Browning products). These result from the reaction of amines with reducing sugars and result in "cooked" or "heated” aromas.
  • thermal reaction products include sulfides such as dimethylsulfide, methyl thiirane and dimethyfdisulfide which are thermal decomposition products of sulfur-containing amino acids such as cysteine or methionine.
  • sulfides such as dimethylsulfide, methyl thiirane and dimethyfdisulfide which are thermal decomposition products of sulfur-containing amino acids such as cysteine or methionine.
  • the KO has a "cooked shrimp" or slightly nutty, roasted aroma.
  • the Maillard reaction products and the sulfides are responsible for these aroma attributes.
  • the semi-volatile flavor compounds in KO show a complex mixture that is composed of fishy smelling alkyl-substituted amines, Maillard reaction products (alkyl pyrazines & pyridines) and traces of lipid oxidation products (aldehydes, ketones, alcohols & hydrocarbons). Traces of N,N-dimethylfomamide (DMF) and N-methylpyrrolidinone (NMP) were detected at trace level in KO. These compounds are noteworthy because they are known or suspected carcinogens. They may be natural products or they may form as artifacts in the KO production process.
  • deodorization processing by washing with dilute HCI (See Tables 5, 6, 12 & 13) completely removes DFM, NMP and odor- causing amines such as TMA from the samples. No appreciable weight loss or color loss occurs in KO following this treatment.
  • the other deodorization treatments such as cation exchange resin (AMMO Chips) and AMMO Chips plus activated carbon were not completely effective at removing the DMF, NMP or amines (See Tables 8-12).
  • a third class of compound in the aroma and flavor of NKO are lipid oxidation products that arise from autoxidation of polyunsaturated fatty acids in the sample. These compounds are a complex mixture of low molecular weight carbonyl compounds (aldehydes & ketones), alcohols, furans and hydrocarbons.
  • Examples of lipid oxidation products in the volatile aroma fraction include acrolein, acetaldehyde, propanal, 2-methyl-l-propen-l-one, MEK, 2- methylfuran, l-penten-3-ol, 2-ethylacrolein, 2-ethylfuran, 2-methyl-2-pentenal and 2-pentenal.
  • Examples of lipid oxidation products in the semi-volatile flavor fraction of KO include 2-hexanone, hexanal, octadiene, trans-2-hexenal, octatriene, 2-heptanone, heptanal, 7-octen-2-one, 2-octanone, 6-methyl-5- hepten-2-one, 2-pentylfuran, 2,4-heptadienal, decatrienal isomers, and others.
  • the decatrienal isomers that result from autoxidation of polyunsaturated fatty acids with 4 or more double bonds. These compounds have a very low sensory threshold and despite their low concentration in the sample they contribute greatly to the fishy aftertaste that lingers on the palate after eating KO.
  • the lipid oxidation levels were still quite low in the KO even after the accelerated aging indicating that the processed sample has at least a one year shelf life at room temperature storage. Storage under nitrogen in leak-tight containers and refrigerated or frozen would greatly inhibit lipid oxidation and extend the KO shelf life much longer.

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Abstract

La présente invention porte sur un procédé pour la désodorisation d'huile extraite d'un animal marin comprenant les étapes consistant à i) laver avec HCl ou avec NaCl ou éluer l'huile d'animal marin sur une résine échangeuse d'ions enlevant l'ammoniac, ii) traiter l'huile d'animal marin avec du charbon actif pour enlever les groupes amines responsables en partie des odeurs ; et iii) distiller sous vide l'huile d'animal marin. La présente invention porte en outre sur une composition alimentaire comprenant une telle huile d'animal marin désodorisée et sur des utilisations correspondantes.
PCT/CA2009/000600 2008-05-02 2009-05-01 Nouveau procédé de désodorisation et amélioration organoleptique d'extraits d'huile d'animal marin Ceased WO2009132463A1 (fr)

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US8609157B2 (en) 2009-10-30 2013-12-17 Tharos Ltd. Solvent-free process for obtaining phospholipids and neutral enriched krill oils
CN104719994A (zh) * 2015-04-14 2015-06-24 江苏优远生物科技有限公司 一种秘鲁鱿鱼排酸过程中产生氨味的抑制剂及方法
WO2016130670A1 (fr) * 2015-02-11 2016-08-18 Orochem Technologies, Inc. Raffinerie d'huile de krill pour la purification d'extrait d'huile de krill
CN107853704A (zh) * 2017-11-19 2018-03-30 荣成海锐芯生物科技有限公司 一种海参油软胶囊的制备方法
CN108424811A (zh) * 2018-04-03 2018-08-21 青岛科技大学 一种精制核桃油气味去除的方法
US10130644B2 (en) 2009-10-29 2018-11-20 Acasti Pharma Inc. Concentrated therapeutic phospholipid compositions
CN108913352A (zh) * 2018-07-27 2018-11-30 山东鲁华海洋生物科技有限公司 一种脱胺低腥磷虾油及其制备方法
CN110650633A (zh) * 2017-05-18 2020-01-03 弗门尼舍有限公司 具有减少的恶臭的海洋蛋白水解产物组合物

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US10130644B2 (en) 2009-10-29 2018-11-20 Acasti Pharma Inc. Concentrated therapeutic phospholipid compositions
US10617702B2 (en) 2009-10-29 2020-04-14 Acasti Pharma Inc. Concentrated therapeutic phospholipid compositions
US9011942B2 (en) 2009-10-30 2015-04-21 Tharos, Ltd. Solvent-free process for obtaining phospholipids and neutral enriched krill oils
US9150815B2 (en) 2009-10-30 2015-10-06 Tharos Ltd. Solvent-free process for obtaining phospholipids and neutral enriched krill oils
US8865236B2 (en) 2009-10-30 2014-10-21 Tharos Ltd. Solvent-Free Process for Obtaining Phospholipids and Neutral Enriched Krill Oils
US8609157B2 (en) 2009-10-30 2013-12-17 Tharos Ltd. Solvent-free process for obtaining phospholipids and neutral enriched krill oils
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CN104719994B (zh) * 2015-04-14 2017-11-21 江苏优普保鲜技术有限公司 一种秘鲁鱿鱼排酸过程中产生氨味的抑制剂及方法
CN104719994A (zh) * 2015-04-14 2015-06-24 江苏优远生物科技有限公司 一种秘鲁鱿鱼排酸过程中产生氨味的抑制剂及方法
CN110650633A (zh) * 2017-05-18 2020-01-03 弗门尼舍有限公司 具有减少的恶臭的海洋蛋白水解产物组合物
CN107853704A (zh) * 2017-11-19 2018-03-30 荣成海锐芯生物科技有限公司 一种海参油软胶囊的制备方法
CN108424811A (zh) * 2018-04-03 2018-08-21 青岛科技大学 一种精制核桃油气味去除的方法
CN108424811B (zh) * 2018-04-03 2021-06-18 青岛科技大学 一种精制核桃油气味去除的方法
CN108913352A (zh) * 2018-07-27 2018-11-30 山东鲁华海洋生物科技有限公司 一种脱胺低腥磷虾油及其制备方法

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