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Title:
NEW DEODORIZATION METHOD AND ORGANOLEPTIC IMPROVEMENT OF MARINE OIL EXTRACTS
Document Type and Number:
WIPO Patent Application WO/2009/132463
Kind Code:
A1
Abstract:
The present invention relates to a process for deodorization of marine extracted oil comprising the steps of i) washing with HCI or with NaCl or eluting marine oil on an ammonia removing ion exchange resin, ii) treating the marine oil with activated carbon to remove amine groups responsible in part for odours; and iii) distilling under vacuum the marine oil. The present invention further provides for a food composition comprising such deodorized marine oil, and uses therefor.

Inventors:
SAMPALIS TINA (CA)
MASSRIEH WAEL (CA)
Application Number:
PCT/CA2009/000600
Publication Date:
November 05, 2009
Filing Date:
May 01, 2009
Export Citation:
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Assignee:
NEPTUNE TECHNOLOGIES & BIORESS (CA)
SAMPALIS TINA (CA)
MASSRIEH WAEL (CA)
International Classes:
C11B3/12; A23D9/00; A23L1/30; A23L5/20; A61K35/56; A61K35/612; A61K35/618; A61P3/06; A61P25/00; C11B1/02; C11B3/00; C11B3/04; C11B3/10; C11B5/00
Domestic Patent References:
WO2005025586A12005-03-24
WO1999064547A11999-12-16
WO2000044862A12000-08-03
Foreign References:
EP0999259A12000-05-10
EP0773283A21997-05-14
EP0507363A11992-10-07
US5006281A1991-04-09
US4915876A1990-04-10
US20030113432A12003-06-19
CA2362663A12001-06-14
JP2002186428A2002-07-02
JPH08302382A1996-11-19
JP2005124439A2005-05-19
JPS5523949A1980-02-20
JP2003313578A2003-11-06
Other References:
WONG C.: "Krill Oil", ALTERNATIVE MEDICINE, 1 February 2008 (2008-02-01), Retrieved from the Internet
BUNEA ET AL.: "Evaluation of the Effects of Neptune Krill Oil on Clinical Course of Hyperlipidemia.", ALTERATIVE MEDICINE REVIEW, vol. 9, no. 4, pages 420 - 428
Attorney, Agent or Firm:
OGILVY RENAULT LLP/S.E.N.C.R.L., S.R.L. (1 Place Ville Mari, Montréal Québec H3B 1R1, CA)
Download PDF:
Claims:

WHAT IS CLAIMED IS:

1. A process for deodorization of marine extracted oil comprising the steps of:

a) washing said marine extracted oil with a strong acid;

b) washing the marine extracted oil obtained at step a) with water;

and optionally at least one of the following steps:

c) treating the marine oil obtained at step a) or b) with activated carbon to remove amine groups responsible in part for odours; and

d) distilling under vacuum the marine oil of step a) or b).

2. A process for deodorization of marine extracted oil comprising the steps of:

a) washing said marine extracted oil with a water-soluble salt; and

b) washing the marine oil treated in step a) with water;

and optionally at least one of the following steps:

c) treating the marine oil obtained at step a) or b) with activated carbon to remove amine groups responsible in part for odours; and

d) distilling under vacuum the marine oil of step a) or b).

3. A process for deodorization of marine extracted oil comprising the steps of:

a) eluting marine oil on an ammonia removing ion exchange resin;

and optionally at least one of the following steps:

b) treating the marine oil obtained at step a) with activated carbon to remove amine groups responsible in part for odours; and

c) distilling under vacuum the marine oil of step b).

4. A process for deodorization of marine extracted oil comprising the steps of:

a) treating marine oil with activated carbon to remove amine groups responsible in part for odours;

and optionally at least one of the following steps:

b) eluting marine oil on an ammonia removing ion exchange resin and

c) distilling under vacuum the marine oil of step b).

5. The process for deodorization of marine extracted oil of claim 1 , wherein the strong acid is 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 .

6. The process for deodorization of marine extracted oil of claim 1 , wherein the strong acid is HCI.

7. The process for deodorization of marine extracted oil of claim 2, wherein the water-soluble salt is selected from the group consisting of NaCI, CaCI 2 , KCI, NaF, NaBr 1 NaI, KBr, Kl, KF, CaF 2 , CaBr 2 , and CaI 2 .

8. The process for deodorization of marine extracted oil of claim 2, wherein the water-soluble salt is NaCI.

9. The process for deodorization of marine extracted oil of claim 8, wherein NaCI is used at a concentration varying from 10 mM to 1 M.

10. The process for deodorization of marine extracted oil of claim 9, wherein said washing step with NaCI consists of washing with at least one part 10OmM to 75OmM NaCI to one part oil.

11. The process for deodorization of marine extracted oil of claim 1 , 2, 5, 6, 7 8, 9 or 10, wherein said washing step with water consists of washing with at least one part water to one part oil.

12. The process for deodorization of marine extracted oil of claim 6, wherein HCI is used at a normality of 0.1 N HCI.

13. The process according to any one of claims 1 to 12, wherein said marine extracted oil is obtained from at least one marine or aquatic biomass.

14. The process of claim 13, wherein the biomass is crustaceans.

15. The process according to claim 13 or 14, wherein the biomass is zooplankton.

16. The process according to claim 15, wherein the zooplankton is krill.

17. The process according to claim 13, wherein the biomass is squid.

18. The process according to any one of claims 1 to 17, wherein said marine extracted oil further comprises an antioxidant.

19. The process according to any one of claims 1 to 18, further comprising the step of admixing marine oil with a masking formulation.

20. The process according to claim 19, wherein elements of said masking formulation are selected from the group consisting of dried thyme leaf total

extract, thyme leaf oil linalool, lemongrass leaf oil, lime oil and vanilla beans total extract, Water, Arabic gum, Medium chain triglycerides, Lecithin of soya or toumesol, Citric acid, Alpha-tocopherols (Vitamine E), Sodium benzoate and Potassium sorbate.

21. A method of masking smell/taste of marine oil, said method comprising the steps of admixing marine oil with a masking formulation.

22. The method of claim 21 , wherein elements of said masking formulation are selected from the group consisting of dried thyme leaf total extract, thyme leaf oil linalool, lemongrass leaf oil, lime oil and vanilla beans total extract, Water, Arabic gum, Medium chain triglycerides, Lecithin of soya or toumesol, Citric acid, Alpha-tocopherols (Vitamine E), Sodium benzoate and Potassium sorbate.

23. A food composition comprising:

a) a masked and/or deodorized marine oil; and

b) an acceptable carrier.

24. The food composition of claim 23, wherein said deodorized marine oil is derived from at least one marine or aquatic biomass.

25. The food composition of claim 24, wherein the biomass is crustaceans.

26. The food composition as according to claim 24 or 25, wherein the biomass is zooplankton.

27. The food composition according to claim 26, wherein the zooplankton is krill.

28. The food composition according to claim 24, wherein the biomass is squid.

29. The food composition according to any one of claims 23 to 28, further comprising an antioxidant.

30. The food composition according to any one of claims 23 to 29, wherein said food composition is incorporated in a food product selected from the group consisting of a dairy product, a beverage, a cereal, a confectionary product, fruit nuggets, biscuits and nutritional bars.

31. Use of a food composition as defined in any one of claims 23 to 30 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.

32. The use of claim 23, wherein the neurodegenerative or psychiatric diseases are selected from the group consisting of dementia, Parkinson's, Alzheimer's, autism, attention deficit disorder, learning disorders, mood disorders, behavioural disorders, multiple sclerosis and muscular dystrophy.

33. The use of claim 23, wherein said food composition reduces plaque formation.

34. The use of claim 23, wherein said food composition reduces the concentration of low-density lipoprotein (LDL).

35. The use of claim 23, wherein said food composition reduces the concentration of triglyceride (TG).

36. The use of claim 23, wherein said food composition increases the concentration of high-density lipoprotein (HDL).

37. In a process for extracting marine oil from a marine or aquatic biomass, said process comprising the steps of:

a) treating said marine organism with an enzymatic cocktail for preventing enzymatic autolysis, and

b) blanching the marine organism so treated at step a) in boiling water,

wherein steps a) and b) are effected in a process for extracting oil either as preliminary steps before oil extraction.

38. In the process of claim 37, said enzymatic cocktail comprising at least one enzyme selected from the group consisting of papain and bromelain.

39. In the process of claim 37 or 38, the marine or aquatic biomass being crustaceans.

40. In the process of any one of claims 37, 38 or 39, the biomass being zooplankton.

41. In the process of claim 40, the zooplankton being krill.

42. In the process of claim 37 or 38, the biomass being squid.

43. In the process of any one of claims 37 to 42, said marine extracted oil further comprising an antioxidant.

Description:

NEW DEODORIZATION METHOD AND ORGANOLEPTIC IMPROVEMENT OF MARINE OIL EXTRACTS

TECHNICAL FIELD

[0001] 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.

BACKGROUND OF THE INVENTION

[0002] 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.

[0003] It is known in the art to use krill and/or marine enzymes for the treatment of a great variety of diseases in human and animals such as infections, inflammations, cancers, HIV/AIDS, pain, polyps, warts, hemorrhoids, plaque, wrinkles, thin hairs, allergic itch, anti-adhesion, eye disease, acne, cystic fibrosis and immune disorders including autoimmune disease and cancer.

[0004] It is also known in the art that 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.

[0005] However, 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.

[0006] 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.

[0007] 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.

[0008] Extract consisting of a pure oil rich in phospholipids, omega-3 and antioxidants from Antarctic krill are known. The synergy between these components creates a remarkably nutritious complex that offers significant health benefits. International patent application publication No WO 00/23546 discloses methods for extracting lipid fractions from marine and aquatic animal material by acetone extractions. The resulting non-soluble and particulate fraction may be further solvent extracted with ethanol or ethyl acetate to achieve further lipid extractions.

[0009] Most marine oils obtained from normal fish contain polyunsaturated fatty acids (PUFA) such as 5 or 6 double bonds, which render them prone to atmospheric oxidation. It is believed that peroxides are produced in this oxidation break down into secondary oxidation products, which exhibit a pronounced taste and smell of fish and shellfish oils. The "fishy odour/flavour" of marine oil is one of the most important problems in the preparation of nutraceuticals for oral consumption. The odor can be extremely stubborn and may remain after transesterification. This odor is due to a large number of volatile matter as well as compounds which are formed by oxidative degradation of highly unsaturated fatty acids. These are predominantly unsaturated carbonyl compounds, which can have an intense odor even at very low concentrations. Even if the problem of oral contact is avoided, the problem still remains intact

after ingestion where the unpleasant regurgitation and breathing with the undesirable odor can be a real problem.

[0010] 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.

[0011] More specifically, the specific smell of frozen krill is found to be caused by dimethyl-sulfide (DMS) and 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 μg/g, and it becomes offensive when it exceeds several μg/g. DMS is enzymatically formed from dimethyl-/?-propiocetine in phytoplanktons which serve as food for krill. Storage at -3O 0 C is desirable to prevent formation of DMS whereas storage at -2O 0 C is insufficient. The offensive odor of krill is also caused by the large amounts of trimethylamine and isobutylamine in 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). Other source of smell is caused by the highly vulnerability of free fatty acids to oxidation caused mainly by the hydrolysis of one fatty acid off the phospholipid creating an increase in the amount of free fatty acids and lysophospholipids in the marine biomass and/or marine extracts.

[0012] Taking measures to inhibit/reduce autolysis and/or hydrolysis will improve the stability and organoleptic properties of marine and/or krill extracts making them suitable for direct consumption or for inclusion in a suitable nutraceutical and/or pharmaceutical and/or cosmetic carrier. It would be highly desirable to be provided with an extract consisting of a pure oil rich in phospholipids, omega-3 and antioxidants of pleasant odor and taste suitable for it to be incorporated in food as a dietary ingredient. It would also be desirable to be provided with a pure oil rich in phospholipids, omega-3 and antioxidants for use in conventional food products.

SUMMARY OF THE INVENTION

[0013] In accordance with the present description, there is now provided 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.

[0014] In an alternate embodiment, it is provided 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.

[0015] In another embodiment, it is disclosed 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.

[0016] It is also provided a method of masking smell/taste of marine oil, said method comprising the steps of admixing marine oil with a masking formulation.

[0017] In an alternate embodiment, it is disclosed a food composition comprising: a masked and/or deodorized marine oil; and an acceptable carrier.

[0018] It is also disclosed the use of 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.

[0019] In another embodiment, it is provided a process for extracting marine oil from a marine or aquatic biomass, said process 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.

DETAILED DESCRiPTION OF THE PREFERRED EMBODIMENT

[0020] The present invention provides a food composition or product comprising a multi-therapeutic oil extract, preferably free of protein.

[0021] 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. Also encompassed is 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.

[0022] The food product can be dairy, beverage, cereal, confectionary, fruit nuggets, biscuit, protein bars among others.

[0023] 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.

[0024] In particular, the coastal regions of Mauritius Island and/or Reunion Island off Madagascar, the Canadian West Coast, the Japanese Coast, the Gulf of St. Lawrence and the Bay of Fundy are krill habitats.

[0025] 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. To inhibit autolysis 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.

[0026] After inhibiting autolysis by rapid enzymatic treatments and/or boiling of the freshly harvested and/or deep frozen raw biomass, there is a marked

reduction of free fatty acids and lysophospholipids detected as described in Table 1.

Table 1

Comparative analysis of treated krill vs non-treated krill after exiting the water

Treated krill Non-treated krill

Parameters Units

S1 S2 S3 S1 S2 S3

Lysophosph

% 1.2 1.0 0.7 7.9 6.7 7.1 atidylcholine

Mg

Acid value 11.4 11.5 12.9 26.7 25.7 26.6 KOH/g

Free fatty g/100g 1.7 1.6 1.6 11.9 10.8 12.2 acids mEq

Peroxide peroxide 0.0 0.0 0.0 0.0 0.0 0.0 value

/Kg

[0027] 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 2

Improved stability indexes of the marine extracts after complete treatment

Parameters S1 S2

Lysophosphatidylcholine 0.0 0.0

Acid value 5.6 7.1

Free fatty acids 1.6 1.6

Peroxide value 0.0 0.0

[0028] 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.

Table 3

Tested marine extracts after washing for improved organoleptic indexes

Protein,

Treatment Total solids Ash sugars.etc

Wash NaCI 1OmM 1 er 0.40 0.21 0.15

Wash Water 2 e 0.17 0.06 0.04

Mean: 0.29 0.14 0.09

Wash NaCI 10OmM 1 er 0.76 0.43 0.16

Wash Water 2 e

0.28 0.06 0.03

Mean: 0.52 0.25 0.09

Wash NaCI 25OmM 1 er 0.97 0.79 0.13

2 e

Wash Water 0.24 0.14 0.03

Mean: 0.61 0.47 0.08

Protein,

Treatment Total solids Ash sugars.etc

Wash NaCI 50OmM 1 er 1.58 1.35 0.15

Wash Water 2 e 0.29 0.21 0.01

Mean: 0.94 0.78 0.08

Wash NaCI 75OmM 1 er 2.13 1.91 0.12

Wash Water 2 e 0.40 0.31 0.01

Mean: 1.27 1.11 0.06

Wash NaCI 1M 1 er 2.87 2.61 0.16

Wash Water 2 e 0.44 0.35 0.02

Mean: 1.66 1.48 0.09

[0029] 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.

[0030] There is also provided a new formulation, which comprises a stable, deodorized oil extract and botanical extracts or other extracts to eliminate/mask the unpleasant odour.

[0031] The 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.

[0032] The extracted oil described herein is one rich in phospholipids.

[0033] 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.

[0034] 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. Unless specifically mentioned herein, 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.

[0035] For the best extraction, 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. However, 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.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] When an oral route is chosen, 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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] Suitable binding agents include polyvinyl pyrrolidine, hydroxypropyl cellulose and hydroxypropyl methyl cellulose and mixtures thereof.

[0044] Suitable solution vehicles include, but are not limited to, ethanol, water, propylene glycol, butylene glycol, acetone, or other pharmaceutically acceptable vehicle.

[0045] Furthermore, it is provided that 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 σ-tocopherol or mixed tocopherols at various concentrations. All those additions have resulted only in a short term improvement in odor/flavor and stability. Treatment of the oil with silica and incorporating a tocopherol, ascorbyl palmitate and lecithin, have been described which thereby subject the silica treated oil in a vacuum steam deodorization at a temperature reaching as high as 21 O 0 C. Processing of oils or extracts under such high temperatures is detrimental to numerous biologically active compounds contained in the product, rending the substance ineffective, unstable and creating artifacts that can in fact may have negative health effect in the long run.

[0046] Stabilization using other compounds such as tetrabutylhydroquinone has also been known to have resulted in a very little success due to short period effect and very bitter after taste of this compound.

[0047] 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.

[0048] It is provided herein a process for removing undesirable odours (deodorizing) or masking off the odour/flavour from the oil extract. The process allows also to obtain a more stable oil extract, allowing the use now of such

deodorized extract to be incorporated in various nutraceutical, personal care and pet food formulations. The deodorization process does not adversely affect the composition of the oil.

[0049] 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. Alternatively, the oil can be run down on an ammonia removing ion exchange resin. These additional steps completely eliminate or remove DMS and odour- 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. 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. Similarly, other salts (other than NaCI), such as calcium salts have been tested and have showed suitable for use in the deodorization process described herein.

[0050] Table 4 below reports data showing the odor/taste improvement in the krill oil.

Table 4

Tests made on various sample showing the odor improvement of krill oil

- Arbitrary values taking into consideration the intensity of the smell and the appreciation of the product; - Values represents the integration under the curse obtained for the GC-MS analysis for this volatile compound (x 10 6 ); and - Values represents the integration under the curse of all the curves obtained for the GC-MS analysis for every volatile compound in the oil (x 10 6 ).

Description of the Krill oil samples tested herein

SSN 80-15 washed with water and then stored at -80 0 C for 15 months

B2O1 C1 washed twice with Acetone, and then with water, as previously described

B2O1 C2 not washed, but heated to 95°C as previously described to evaporate volatile agents therefrom

B2O2C1 washed once with water, and then heated to 95°C as previously described to evaporate volatile agents therefrom

B2O1 C1 Washed three times with acetone, then with Calcium (Ca ++ )

B2O4C1 Washed twice with water and then heated to 65°C to evaporate volatile agents therefrom

SSN2 Obtained from Krill that has not been boiled during the extraction process to inactivate degradation enzymes that may be present in the krill extract

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

B2O6C1 Washed with 100 mM NaCI, then with water (ratio 1 :2), and then heated to 45°C to evaporate volatile agents therefrom

B2O5C1 Washed with 250 mM NaCI, then with water, and then heated to 45 0 C to evaporate volatile agents therefrom

B2O3C1 Washed with 100 mM NaCI, then with water (ratio 1 :2), and then heated to 65°C to evaporate volatile agents therefrom

B2O5C1 Washed with 100 mM NaCI, then with water (ratio 1 :2), and then heated to 45°C as previously described to evaporate volatile agents therefrom

[0051] Furthermore, it is disclosed an effective masking and stabilization process of the marine oil using a botanical formula. 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.

[0052] 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. Furthermore, additional acceptable adjuvant may be added to the composition of the present formulations.

[0053] Using samples from extracted oil, tests were conducted to find and develop formulations based on single substance or combinatorial methods that would help mask off odour/flavour and stabilize the oil. 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.

[0054] After conducting numerous tests for optimum quantity and combinations of the botanical extracts and oils, the formulation containing the amount indicated herein below were found to be acceptable from the point of view of eliminating off odour/flavour. Of course this is only one possible formulation, and alternate combination of the elements of the formulation is also possible. Rigorous organoleptic tastes were conducted by organizing voluntary tasting tests for palatability.

[0055] 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.

[0056] The following methods were used to determine the total microbial counts:

Total plate count: CFU/g 3M & MFHPB-33;

Yeast and Mould 3M & MFHPB-32; and Conforms 3M & MFHPB-34.

[0057] The following formulation was found to be acceptable for changing the off odour/flavour of 1 kg of krill extracted oil:

10 ml of thyme essential oil; 10 ml rosemary total extract; 10 ml of Aloe extract; 5.0 ml of rosemary essential oil;

5.0 ml of lemon grass essential oil;

3.1 ml vanilla beans total extract; and 2.0 grams of thyme total extract.

[0058] The following formulation was found to be acceptable for changing the off odour/flavour of 1 kg of krill extracted oil after "deodorization":

Water;

Arabic gum;

Medium chain triglycerides;

Lecithin of soya or toumesol;

Citric acid;

Alpha-tocopherols (Vitamine E);

Sodium benzoate; and

Potassium sorbate.

[0059] The following samples have been prepared using deodorized krill oil as disclosed herein:

100 g. of Yoghurt (strawberry flavored) containing 500 mg of deodorized krill oil;

100 g. of Yoghurt plain (a) containing 500 mg of deodorized krill oil;

100 g. of Yoghurt plain (a) containing 350 mg of deodorized krill oil; and

100 g. of Smoothie (strawberry flavored) containing 100 mg of deodorized krill oil.

[0060] Under the deodorization process described herein, significantly low temperature (45 0 C, vacuum steam deodorization) was used while removing the solvent from the oil. The resulting deodorized sample was superior in taste and smell compared to the original extracted oil and to other fish oils sold in super markets.

[0061] Moreover, with the deodorization process described herein, the resulting deodorized krill oil was more stable for a longer period of time, compared to untreated krill oil.

[0062] One fact to note is that untreated krill oil as commercially known and available on the market does not produce homogeneous mix with yoghurt, and this, even though the oil is formulated as an emulsion with PROMILK 801™. By opposition, when using krill oil such as the one obtained from Neptune, which has been extracted from krill that has been boiled during the extraction process to inactivate degradation enzymes that may be present in the krill extract is a very good candidate for preparing a stable and homogenous emulsion and thereby is more appropriate to be incorporated in yoghurt.

[0063] 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.

[0064] Finally, it was not possible to make any follow-up tests on the concentration of volatile compounds generated by the degradation of molecules of either protein or peptide molecules. Alternative to these tests, organoleptic tests were carried out to determine the evolution of the product over time. These tests revealed that the treated krill oil was clearly different from the untreated krill oil. It should be noted that the treatment is supposedly carried out to reduce the presence of these volatile compounds, confirming that the

treated oil maintained its properties better that the untreated oil over time since these volatile compounds were not present, thereby avoiding any further degradation caused by these volatile compounds.

[0065] As may be apparent from the data reported herein, 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.

[0066] As a result, krill oil can now be utilized in either yoghurt or energy bars ("bars", "food bars" or "functional food bars"). The content in omega-3, including EPA and DHA, remains stable in these bars for a period of more than 59 days, i.e. the whole length of time of the study for the stability of the krill oil in the bars.

[0067] 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.

[0068] The results of the phospholipid were expressed in molar concentration due to the fact that it was not possible to obtain an average molecular weight for this mixture of phospholipids of diverse origin (marine and animal or vegetal).

[0069] 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. In the present study, 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.

[0070] In light of the above, it is thus clear that 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).

[0071] After vacuum steam deodorization, running down on Ammonia removing ion exchange resin column or washing with NaCI or with HCI, 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. However, it should be noted that 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.

[0072] 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.

[0073] There is also provided 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. These 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). The composition comprises a therapeutically effective amount of krill and/or marine oil in association with a nutraceutically acceptable carrier or excipient.

[0074] 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.

[0075] 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).

Deodorization Processes (more embodiement)

[0076] The data reported herein detail the analytical chemistry documentation of the deodorization processing on krill oil. Comparison of the aroma and flavor profile of krill oil without treatment and after various deodorization strategies and accelerated aging was made and designed to predict a one-year shelf life at room temperature.

[0077] For initial deodorization, 5.0 grams of extracted oil (as obtained from Mercola.com as previously mentioned) was weighed and washed with 40 ml diluted acid solution (0.1 N HCI), followed by centrifugation for 30 minutes at 2500 RPM. The samples were filtered though a filter paper and subjected to thin film vacuum steam distillation using 95% ethanol and water. Following this,

volatile and semi-volatile analyses were conducted by HS-GC-MS and P&T-TD- GC-MS to document efficacy of deodorization treatment. After the acid washing, the sample was processed and treated (P&T) using the solid P&T apparatus rather than liquid bubbler apparatus due to foaming of the sample. 1.25 g of the washed oil sample was used for further analysis.

[0078] An alternate deodorization of the oil by taking 5.0 grams (three times) of the sample with 15.0 grams of Ammonia Removing Ion Exchange Resin (AMMO Chips Cationic Resin, Aquarium Pharmaceuticals Inc, P.O.Box 218, Chalfont, PA 18914, 614604-0204) three times was accomplished. Following the above procedure, the samples were dissolved with 50 ml petroleum ether and an equal amount of 95% ethanol, shaken vigorously for 2 minutes and was then left at room temperature for one hour. The solution was then filtered through 20/v filter paper, followed by thin film vacuum steam distillation using 95% ethanol and water. Volatile and semi-volatile analyses by HS-GC-MS and P&T-TD-GC-MS to document efficacy of deodorization treatment. Similar operation conditions as indicated previously were used for P&T.

Analysis Methodology

[0079] This is a summary of krill Oil (KO) potential and/or alternate deodorization treatments (used in combination) and analyses performed:

1 ) Profiling of KO by Headspace-GC-MS (HS-GC-MS) "as received" to determine the volatile aroma components responsible for the characteristic "fishy" odor;

2) Profiling of KO by Purge & Trap-Thermal Desorption-GC-MS (P&T-TD-GC-MS) without treatment to screen for semi-volatile compounds that are responsible or characteristic of the "fishy" taste;

3) Deodorization of KO by washing with dilute acid solution (0.1 N HCI) followed by thin film vacuum steam distillation. Repeat

volatile and semi-volatile analyses by HS-GC-MS and P&T-TD- GC-MS to document efficacy of deodorization treatment;

4) Deodorization of KO by treating with Ammonia Removing Ion Exchange Resin (AMMO Chips Cationic Resin) followed by thin film vacuum steam distillation. Repeat volatile and semi-volatile analyses by HS-GC-MS and P&T-TD-GC-MS to document efficacy of deodorization treatment;

5) Deodorization of KO by treating with Ammonia Removing Ion Exchange Resin (AMMO Chips Cationic Resin) plus activated carbon followed by thin film vacuum steam distillation. Repeat volatile and semi-volatile analyses by HS-GCMS and P&T-TD-GC- MS to document efficacy of deodorization treatment;

6) Deodorization of KO by washing with dilute acid solution (0.1 N HCI) plus activated carbon treatment followed by thin film vacuum steam distillation. Processed KO sample was subjected to accelerated aging for 10 days at 40 0 C to simulate a one year shelf life at room temperature. Repeat volatile and semi volatile analyses by HS-CC-MS and P&T-TD-GC-MS to document efficacy of deodorization treatment and accelerated aging; and

7) Other deodorization treatments such as washing with dilute caustic soda (0.1 N NaOH) were unsuccessful due to problematic emulsion formation and other issues.

[0080] Details of the analysis methodology are given as follows:

Headspace-GC-MS Analyses for Volatile Aroma Profile

[0081] 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 resulting Headspace-GC-MS chromatograms were then subjected to a thorough scan-by-scan search of the data to identify all volatile aroma components (compounds with boiling points below toluene) and especially those with potential to cause "fishy" off-odor.

Purge & Trap-Thermal Desorption-GC-MS Analyses for Flavor Profile

[0082] In these analyses, 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. 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.

[0083] The volatile and semi-volatile aroma/flavor profiles of the KO samples as measured by Headspace-CC-MS and Purge & Trap-Thermal Desorption- GC-MS are presented in Tables 5 - 14. Each Table lists the MS Scan # of the peaks detected, the peak area integration values, the peak assignment and the concentration of each component calculated in parts per million on a weight to weight basis (PPM w/w). The volatile aroma compounds (compounds w/ boiling points < toluene) are reported in the Headspace data in Tables 5, 7, 9, 11 and 12. The semi-volatiles flavor compounds (compounds w/ boiling points > toluene) are reported in the P&T-TD-GC-MS data in Tables 5, 7, 9, 11 and 13.

[0084] Most noteworthy in the volatile aroma profile of KO before treatment (See Table 5) is the presence of trimethylamine (TMA). TMA is very strongly fishy smell and this and several of the other amines found at lesser concentration are primarily responsible for the fishy odor of the sample. 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. There are a series of so called "Strecker Aldehydes" in the data that are reaction products of amino acids such as alanine, valine, leucine and isoleucine with reducing sugars such as glucose. These compounds are telltale signs that the product has undergone some type of thermal processing at one point in its processing history.

[0085] Other 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. In addition to the fishy note, the KO has a "cooked shrimp" or slightly nutty, roasted aroma. The Maillard reaction products and the sulfides are responsible for these aroma attributes.

[0086] The semi-volatile flavor compounds in KO (See Table 6) 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. They are found at exceedingly trace level and should not be problematic with respect to health hazard at the observed concentrations. In any event, 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.

[0087] 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).

[0088] 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.

[0089] 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. Among the most responsible for the "fishy" flavor are 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.

[0090] Basically, of all of the deodorization treatments, the washing with dilute 0.1 N HCI followed by activated carbon treatment and vacuum distillation was found to be most efficacious. This combination of treatment was found to be completely effective at removing amines (such as TMA, pyridine, pyrazlnes etc.), DMF, NMP, sulfur-containing compounds and many highly water soluble components such as acetone and alcohols. However, this treatment was not effective at removing most lipid oxidation products. A moderate increase in lipid oxidation levels was noted immediately following the dilute acid washing procedure and a gradual increase was observed after accelerated aging at 40 0 C for 10 days (See Tables 7, 8, 13 and 14). 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.

Table 5

Headspace GG-MS Volatile Odor Profile on Krill Oil without treatment

Total Headspace Volatiles @ 100°C/30 Min. 111.68 (Compds. W/Boiling Points < Toluene

Table 6

Purge & Trap-Thermal Desorption-GC-MS Semi-Volatile Odor Profile on untreated Krill Oil

Total Semi-Volatile Out-Gas Products @ 100°C/30 Min. 33.85 (Compds. with Boiling Points > Toluene)

Table 7

Headspace GC-MS Volatile Odor Profile on Acid Washed and Vacuum

Distilled KO

Total Meadspace Volatϋes @ 100CI30 Min. 19.59 (Compds. wl Boiling Pohts < Toluene)

Table 8

Purge & Trap-Thermal Desorption-GC-MS Semi-Volatile Odor Profile on Acid Washed and Vacuum Distilled KO

Table 9

Headspace GC-MS Volatile Odor Profile on KO Treated with Ammonia Removing Ion Exchange Resin & Vacuum Distilled

Table 10

Purge & Trap-Thermal Desorption-GC-MS Semi-Volatile Odor Profile on KO Treated w/ AMMO Chips & Vacuum Distilled

Table 11

Headspace GC-MS Volatile Odor Profile on KO Treated with AMMO Chips + Activated Carbon + Vacuum Distilled

Table 12

Purge & Trap-Thermal Desorption-GC-MS Semi-Volatile Odor Profile on KO Treated w/ AMMO Chips + Activated Carbon + Vacuum Distilled

Table 13

Headspace GC-MS Volatile Odor Profile on KO Acid Washed + Activated

Carbon + Vacuum Distilled Accelerated Aging at 40°C/10 Days

Table 14

Purge 4% Trap-Thermal Desorption-GC-MS Semi-Volatile Odor Profile on

KO Acid Washed + Activated Carbon + Vacuum Distilled

Accelerated Aging at 40°C/10 Days

[0091] While the invention has been described in connection with specific embodiments thereof, it will be understood that it is capable of further

modifications and this application is intended to cover any variations, uses, or adaptations of the invention following, in general, the principles of the invention and including such departures from the present disclosure as come within known or customary practice within the art to which the invention pertains and as may be applied to the essential features hereinbefore set forth, and as follows in the scope of the appended claims.