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`the
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`International application number: PCT /N02007 /000402
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`International filing date:
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`15 November 2007 (15.11.2007)
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`Number:
`60/859,289
`Filing date:
`16 November 2006 (16.11.2006)
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`World Intellectual Property Organization (WIPO) - Geneva, Switzerland
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`RIMFROST EXHIBIT 1036 page 0001
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`PCT/NO 0 7 0 0 4 0 2
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`PA 1669084
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`11Q)NIID,11Q)WU:.f!M('!lllfE·S.iID ~!JJESlE~~ S~Is,~MfE:;;
`UNITED STATES DEPARTMENT OF COMMERCE
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`PROVISIONAL APPLICATION FOR PATENT COVER SHEET
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`Given Name (first and middle (if any))
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`Family Name or Surname
`
`Harald
`
`Breivik
`
`Residence
`(City and either State or Foreign Country)
`Porsgrunn, Norway
`
`INVENTOR(S)
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`0 Additional inventors are being named on the
`separately numbered sheets attached hereto
`TITLE OF THE INVENTION (280 characters max)
`
`PROCESSES FOR PRODUCTION OF OMEGA-3 RICH MARINE PHOSPHOLIPIDS FROM KRILL
`
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`Copy provided by USPTO from the IFW Image Database on 11/08/2007
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`RIMFROST EXHIBIT 1036 page 0003
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`
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`rli
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`15.11.2006
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`P60602925USOO
`krill
`
`Pronova Biocare AS
`P.O. Box420
`N-1327 Lysak.er
`NORWAY
`
`> •
`
`Inventor:
`
`Harald Breivik
`Uranusvn. 22
`N-3942 Porsgrunn
`NORWAY
`
`Title: "Processes for production of omega-3 rich marine phospholipids from krill"
`
`Copy provided by USPTO from the IFW Image Database on 11/0812007
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`RIMFROST EXHIBIT 1036 page 0004
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`
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`Field of the invention
`
`The present invention relates to a process for preparing a substantially total lipid
`fraction from fresh krill, and a process for separating phospholipids from the other
`lipids.
`
`s
`
`Background of the invention
`
`Marine phospholipids are useful in medical products, health food and human nutrition,
`as well as in fish feed and means for increasing the rate of survival of fish larval and fry
`of marine species like cod, hali.but and turbot.
`
`Phospholipids from marine organisms comprise omega-3 fatty acids. Omega-3 fatty
`acids bound to marine phospholipids are assumed to have particularly useful properties.
`
`10
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`IS
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`Products such as fish milt and roe are traditional raw materials for marine
`phospholipids. However, these raw materials are available in limited volumes and the
`price of said raw materials is high.
`
`20 Krill are small, shrimp-like animals, containing relatively high concentrations of
`phospholipids. In the group Euphasiids, there is more than 80 species, of which the
`Antarctic krill is one of these. The current greatest potential for commercial utilisation is
`the Antarctic Euphausia superba. E. superba has a length of2-6 cm. Another krill
`species is £. crystallorphias.
`
`Fresh krill contains up to around 10 % of lipids, of that approximately 50 of%
`phospholipids. Phospholipids from krill comprise a very high level of omega-3 fatty
`acids, whereof the content of eicosapentaenoic acid (EPA) and docosahexaenoic acid
`(DHA) is above 40 %. The approximate composition of lipids from the two main
`species of Antarctic krill is given in Table 1.
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`25
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`35
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`Copy provided by USPTO from the IFW Image Database on 11/08/2007
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`RIMFROST EXHIBIT 1036 page 0005
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`2
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`Table 1: Composition of krill lipids. Lipid classes, (ar:, oroximate sum EPA + DHA)
`Wax esters
`Glycerides
`Phospholipids
`Ratio
`EPA/DHA
`1.4-1.5
`
`1
`
`50 (7)
`
`50 (40-45)
`
`Euphausia
`superba
`Euphausia
`crysta/lorphias
`
`40
`
`20 (4)
`
`40 (30-33)
`
`1.3
`
`Furthermore, Antarctic krill has lower level of environmental pollutants than traditional
`fish oils.
`
`s
`
`The krill has a digestive system with enzymes, including lipases, that are very active
`around 0° C. The lipases stay active after the krill is dead, hydrolysing part of the krill
`lipids. An unwanted effect of this is that krill oil normally contains several percents of
`free fatty acids. If the krill has to be cut into smaller fragments before being processed,
`the person skilled in the art will immediately realise that this will increase the degree of
`hydrolysis. Thus, it is a desire to find a process that can utilise whole, fresh krill, or
`whole body parts from krill, as such a process will provide a product with improved
`quality and low degree of hydrolysis of lipids. This improved quality will affect all
`groups of krill lipids, including phospholipids, triglycerides and astaxanthin esters.
`
`Krill lipids are to a large extent located in the animals' head. A process that can utilise
`fresh krill is therefore also well suited for immediate processing of the by-products from
`krill wherefrom the head is peeled off, a product that can be produced onboard the
`fishing vessel.
`
`From US Patent No. 6,800,299 of Beaudion et al. it is disclosed a method for extracting
`total lipid fractions from krill by successive extraction at low temperatures using
`organic solvents like acetone and ethanol. This process involves extraction with large
`amounts of organic solvents which is unfavourable.
`
`K. Yamaguchi eta/. (J. Agric. Food Chem. 1986 34, 904-907) showed that
`supercritical fluid extraction with carbon dioxide, which is the most common solvent for
`supercritical fluid extraction, of Antarctic krill resulted in a product mainly consisting of
`unpolar lipids (mostly triglycerides), and no phospholipids.
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`Copy provided by USPTO from the IFW Image Database on 11/08/2007
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`RIMFROST EXHIBIT 1036 page 0006
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`
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`3
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`Y. Tanaka and T. Ohkubo (J. Oleo. Sci.(2003), 52, 295-301) quotes the work of
`Y amaguci et al. in relation to their own work on extraction of lipids from salmon roe. In
`a more recent publication (Y. Tanaka et al. (2004), J. Oleo. Sci., 53, 417-424) the same
`authors try to solve this problem by using a mixture of ethanol and C02 for extracting
`the phospholipids. By using C02 with 5 % ethanol no phospholipids were removed
`from freeze dried salmon roe, while by adding 10 % ethanol, 30 % of the phospholipids
`were removed, and by adding as much as 30 % ethanol, more than 80 % of the
`phospholipids were removed. Freeze drying is a costly and energy consuming process,
`and not suited for treatment of the very large volumes of raw materials that will become
`available by commercial krill fisheries.
`
`Tanaka et al. tried to optimise the process by varying the temperature of the extraction,
`and found that low temperatures gave the best results. 33°C, a temperature just above
`the critical temperature for C02, was chosen as giving best results.
`
`5
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`10
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`15
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`Contrary to these findings, we have surprisingly found a process for extraction of a
`substantially total lipid fraction from fresh krill, without the need for complicated and
`costly pre-treatment like freeze drying of large volumes. The lipid fraction contained
`triglycerides, astaxanthin and phospholipids. We did not have to dry or deoil the raw
`20 material before processing. Contrary to Tanaka et al. we have found that a short heating
`of the marine raw material was positive for the extraction yield. It was also shown that
`pre-treatment like a short-time heating to moderate temperatures, or contact with a solid
`drying agent like molecular sieve, of the krill can make ethanol wash alone efficient in
`removing phospholipids from fresh krill.
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`25
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`30
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`35
`
`Summary of the invention
`
`It is a main object of the present invention to provide a process for preparing a
`substantially total lipid fraction from fresh krill without using organic solvents like
`acetone.
`
`The exposure to the supercritical fluid will prevent oxidation from taking place, and the
`combined carbon dioxide/ethanol is expected to deactivate any enzymatic hydrolysis of
`the krill lipids. As the process according to the invention requires a minimum of
`handling of the raw materials, and is well suited to be used on fresh krill, for example
`onboard the fishing vessel, the product according to the invention is expected to contain
`substantially less hydrolysed and/or oxidised lipids than lipid produced by conventional
`
`I·
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`Copy provided by USPTO from the IFW Image Database on 11/08/2007
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`RIMFROST EXHIBIT 1036 page 0007
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`4
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`processes. This also means that there is expected to be less deterioration of the krill lipid
`antioxidants than from conventional processing. The optional pre-treatment involving
`short-time heating of the fresh krill will also give an inactivation of enzymatic
`decomposition of the lipids, thus ensuring a product with very low levels of free fatty
`acids.
`
`Another object of the present invention is to provide a process for preparing a
`substantially total lipid fraction from other marine raw materials like fish gonads,
`Ca/anus species, or high quality krill meal.
`
`Another object of the present invention is to provide a substantially total lipid fraction
`high in long chain polyunsaturated omega-3 fatty acids .
`.
`These and other objects are obtained by the process and lipid fraction as defined in the
`accompanying claims.
`
`According to the invention it is provided a process for extracting a substantially total
`lipid fraction from fresh krill, comprising the steps of:
`a) reducing the water content of krill raw material; and
`b) extracting the water reduced krill material from step a) with supercritical C02
`containing ethanol, methanol, propanol and/or iso-propanol.
`
`In a preferred embodiment the invention it is provided a process for extracting a
`substantially total lipid fraction from fresh krill, comprising the steps of:
`a) reducing the water content of krill raw material; and
`b) extracting the water reduced krill material from step a) with supercritical C02
`containing ethanol.
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`25
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`In a preferred embodiment of the invention, step a) comprises washing of the krill raw
`30 material with ethanol, methanol, propanol and/or iso-propanol in a weight ratio 1 :0.5 to
`1 :5. Preferably, the krill raw material is heated to 60-100 °C, more preferably 70-95 °C
`before washing. Furthermore, the krill raw material is preferably heated for about 1 to
`15 minutes, more preferably for about 1 to 5 minutes, before washing.
`
`35
`
`In another preferred embodiment of the invention, step a) comprises bringing the krill
`raw material in contact with molecular sieve or an other form of membrane for removal
`of water.
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`Copy provided by USPTO from the IFW Image Database on 11/08/2007
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`RIMFROST EXHIBIT 1036 page 0008
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`
`
`5
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`Preferably, the amount of ethanol, methanol, propanol and/or iso-propanol in step b) is
`5-20 % by weight, more preferably 10-15 % by weight.
`
`5
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`10
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`In addition to producing a product containing the total lipids of krill, the invention also
`can be used for separating phospholipids from the other lipids. To make separate the
`total lipids obtained by the supercritical extraction of the present invention into the
`different lipid classes, extraction of the said total lipids with pure carbon dioxide will
`remove the nonpolar lipids from the omega-3 rich phospholipids. Extraction of the total
`lipids with carbon dioxide containing less than 5 % ethanol or methanol is another
`option.
`
`15
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`•
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`As the phospholipids are much richer in the valuable omega-3 fatty acids than the other
`lipid classes, this makes the invention useful for producing high concentrates of omega-
`3 fatty acids. While commercially available fish oils contain 11-33% total omega-3
`fatty acids (Hjaltason, B and Haraldsson, GG (2006) Fish oils and lipids from marine
`sources, In: Modifying Lipids for Use in Food (FD Gunstone, ed), Woodhead
`Publishing Ltd, Cambridge, pp. 56-79), the phospholipids of krill contain much higher
`levels (Ellingsen, TE ( 1982) Biokjemiske studier over antarktisk krill, PhD thesis,
`20 Norges tekniske lwyskole, Trondheim. English summary in Publication no. 52 of the
`Norwegian Antarctic Research Expeditions (1976/77 and 1978179)), see also Table 1.
`The omega-3 rich phospholipids can be used as they are, giving the various positive
`biological effects that are attributed to omega-3 containing phospholipids.
`Alternatively, the phospholipids can be transesterified or hydrolysed in order to give
`esters (typically ethyl esters) or free fatty acids or other derivatives that are suitable for
`further concentration of the omega-3 fatty acids. As examples, the ethyl esters of krill
`phospholipids will be valuable as an intermediate product for producing concentrates
`that comply with the European Pharmacopoeia monographs no. 1250 (Omega-3-acid
`ethyl ester 90), 2062 (Omega -3-acid ethyl esters 60) and 1352 (Omega-3-acid
`triglycerides). At the same time, the remaining lipids (astaxanthin, antioxidants,
`triglycerides, wax esters) can be used as they are for various applications, including feed
`in aquaculture, or the lipid classes can be further separated.
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`25
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`Thus, still another object of the present invention is to provide a process for separating
`phospholipids from the other lipids as described above.
`
`35
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`Detailed description of the invention.
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`Copy provided by USPTO from the IFW Image Database on 11/08/2007
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`RIMFROST EXHIBIT 1036 page 0009
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`6
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`The process can be performed with a wide variety of processing conditions, some of
`which are exemplified below.
`
`5
`
`In the following "fresh" krill is defined as krill that is treated immediately after
`harvesting, or sufficiently short time after harvesting to avoid quality deterioration like
`hydrolysis or oxidation of lipids, or krill that is frozen immediately after harvesting.
`Fresh krill can be the whole krill, or by-products from fresh krill (i.e. after peeling).
`
`10 Moreover "krill" also includes krill meal.
`
`Examples
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`15
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`Example 1
`Processing of freeze dried krill
`Freeze dried krill was extracted with supercritical C02. This gave a product of 90 g/kg.
`Analysis showed that the extract contained a sum of EPA plus DHA of only 5.4%,
`showing that this did not contain a significant amount of the omega-3 rich
`phospholipids. A second extraction with C02 containing 10 % ethanol resulted in an
`extract of lOOg/kg (calculated from starting sample weight). 31P NMR showed that the
`product contained phospholipids. The extract contained a sum of EPA plus DHA of
`33.5 %.
`
`In both steps the extraction conditions were 300 bar, 50°C.
`
`Thus, it is possible substantially to separate the omega-3 rich phospholipids from the
`less omega-3 rich components of the krill lipids.
`
`In a second experiment the freeze dried krill was extracted twice with the same pressure
`and temperature as above, first with 167 parts (weight) of pure C02, and then with 167
`part (weight) of C02 containing 10 % ethanol. The combined extract (280 g/kg raw
`material) was analysed by 13C and 31P NMR. The analyses showed that the product
`contained triglycerides and phospholipids as major components. Like the previous
`extracts the dark red colour showed that the extract contained astaxanthin.
`
`We are not aware that a process according to Example I has been used for freeze dried
`krill. It could be argued that this could be anticipated from Y. Tanaka et al. (2004) J.
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`Copy provided by USPTO from the IFW Image Database on 11/08/2007
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`RIMFROST EXHIBIT 1036 page 0010
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`7
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`Oleo Sci. 53, 417-424. However, in this prior art C02 with 10 % ethanol resulted in
`only 30 % of the phospholipids being extracted. 20 % ethanol had to be used in order to
`extract 80 % of the phospholipids.
`
`Examples according to the invention:
`
`Example2
`Fresh E. superba (200 g) was washed with ethanol (1: 1, 200 g) at around 0°C. The
`ethanol extract (1.5 %) contained inorganic salts (mainly NaCl) and some organic
`material.
`
`The ethanol washed krill was extracted with C02 containing 10 % ethanol. This gave an
`extract of 12 g (6 % based on starting krill). Analysis (TLC and NMR) showed that the
`extract contained phospholipids, triglycerides and astaxanthin.
`
`The person skilled in the art will realise that supercritical carbon dioxide can act as a
`solvent for ethanol. Thus, an alternative procedure for modifying the solvent power of
`the C02 is to utilise pressure/temperature conditions so that ethanol is dissolve directly
`from the ethanol containing krill raw material, without having to be added by a pre(cid:173)
`treatment of the C02• This also applies for the examples below.
`
`Example 3
`Fresh E. superba (200 g) was washed with ethanol (1:3, 600 g) at around 0°C. The
`ethanol extract (7.2 %) contained phospholipids, triglycerides and astaxanthin, and
`some inorganic salts. The extract contained 26.3 % (EPA + DHA), showing that the
`relative content of phospholipids was high.
`
`The ethanol washed krill was extracted with C02 containing I 0 % ethanol. This gave an
`extract of 2.2 % based on starting krill. Analysis (TLC and NMR) showed that the
`extract contained phospholipids, triglycerides and astaxanthin. However, as the extract
`contained only 8.1 % (EPA + DHA) it was concluded that the phospholipids content
`was low.
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`Copy provided by USPTO from the IFW Image Database on 11/08/2007
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`RIMFROST EXHIBIT 1036 page 0011
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`8
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`Example4
`Fresh E. superba was treated with the same two-step process as above, except that the
`ethanol amount in the washing step was increased to 4:1. The ethanol extract was 7.2 %
`compared to the starting material, while the supercritical fluid extract was 2.6 %.
`
`Examples
`Fresh£. superba (200 g) was put in contact with molecular sieve (A3, 280 g) in order to
`remove water from the krill raw material. Extraction with C02 containing I 0 % ethanol
`gave an extract of 5.2 % calculated from the starting weight of krill. Analyses showed
`that the extract contained triglycerides, phospholipids and astaxanthin. The extracted,
`whole krill, was completely white, except for the black eyes.
`
`Example 5 shows the effect of removing water. Molecular sieve was chosen as an
`alternative to ethanol. These examples are not intended to be limiting with regard to
`potential agents for removal of water. Molecular sieve and other drying agents can be
`mild and cost effective alternatives to freeze drying.
`
`Example6
`Fresh E. superba (200 g) was washed with ethanol (1:1) as in example 2, but with the
`difference that the raw material had been pre-treated at 80°C for 5 minutes. This gave
`an ethanol extract of 7 .3 %. Supercritical fluid extraction with C02 containing I 0 %
`ethanol gave an additional extract of 2.6 % calculated from the fresh raw material. The
`total e~tract was 9.9%, and analyses (TLC, NMR) showed that the extract was rich in
`phospholipids, and also contained triglycerides and astaxanthin. The remaining, whole
`krill was completely white, except for the black eyes.
`
`The results show that beat-treatment gives an increased yield of lipids compared to
`the same treatment with no heating. After heat-treatment of the raw material, one part
`(weight) of ethanol gave the same result as four parts of ethanol without heat treatment.
`
`The heat treatment gives as additional result that the highly active krill digestive
`enzymes are inactivated, reducing the potential lip.id hydrolysis.
`
`The person skilled in the art will realise that the processes described above also can be
`used for other raw materials than krill, for example the isolation of omega-3 rich
`phospholipids from fish gonads, or from Ca/anus species. Some krill species are rich in
`wax esters (example: E. crystallorphias), and the same will be the case for Ca/anus
`
`s
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`Copy provided by USPTO from the IFW Image Database on 11/08/2007
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`RIMFROST EXHIBIT 1036 page 0012
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`species. The person skilled in the art will realise that by processing as described above,
`the wax esters will be concentrated in the unpolar lipid fractions~
`
`9
`
`Furthermore, the person skilled in the art will realise that combination of process steps
`as given above can be used for separating the polar (i.e. phospholipids) and unpolar
`lipids of krill. It will also be possible to make an extract of the total lipids of krill
`according to one of the examples above, and then make a second extraction of this
`intermediary product in order to separate the lipid classes. For example, an extraction
`with pure carbon dioxide would remove the nonpolar lipids from the omega-3 rich
`phospholipids.
`
`In another embodiment, the process according to the invention is used to extract krill
`meal, wherein provided the krill meal has been produced in a sufficiently mild way to
`avoid deterioration of the krill lipids.
`
`The person skilled in the art will also realise that a process as described above can be
`used to extract other marine raw materials like fish gonads and Ca/anus species.
`
`s
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`10
`
`IS
`
`A lipid fraction, or lipid product, derived from the process according to the invention
`20 may have some additional advantages related to quality compared to known krill oil
`products (produced by conventional processes), such as for instance a krill oil from
`Neptune Biotechnologies & Bioresources extracted from a Japanese krill source
`(species not specified) with the following composition:
`
`2S Total Phospholipids
`
`Esterified astaxanthin
`
`Vitamin A
`
`Vitamin E
`
`Vitamin D
`
`30 Total Omega-3
`
`EPA
`
`DHA
`
`~40.0%
`
`~ 1.0 mg/g
`
`~ 1.0 IU/g
`
`~ 0.005 IU/g
`
`~ 0,1 IU/g
`
`~ 30.0 %
`
`~ 15.0%
`
`~9.0%
`
`A lipid product or fraction according to the invention is expected to;
`
`35
`
`Copy provided by USPTO from the IFW Image Database on 11/0812007
`
`RIMFROST EXHIBIT 1036 page 0013
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`
`
`•
`
`10
`contain substantially less hydrolysed and/or oxidised lipids than lipid produced
`by conventional processes,
`be less deterioration of the krill lipid antioxidants than from conventional
`processing,
`•
`contain very low levels of free fatty acids, and/or
`• be substantially free from trace of organic solvents.
`
`•
`
`By "oxidised" lipids is meant both primary oxidation products (typically measured as
`peroxide value), secondary oxidation products (typically carbonyl products, often
`analysed as anisidine value) and teritiary oxidation products (oligomers and polymers).
`
`Thus, the invention includes commercial lipid or krill oil products produced by the
`process according to the invention.
`
`s
`
`10
`
`15 Moreover, examples of a lipid compositions obtained by the process according to the
`invention are presented in the tables below, and also included herein.
`
`Table 2
`
`Lipid composition
`Phospholipids
`EPA
`DHA
`
`> 30 - 40 % by weight
`> 5 -15 % by weight
`> 5 - 15 % by weight
`
`20 According to the invention, the extract can be concentrated with respect to the content
`of phospholipids. Some typical lipid compositions are illustrated by table 3-5, and
`included herein:
`
`25
`
`Table 3
`Lipid composition
`Phospholipids
`EPA
`DHA
`
`Table 4
`Lipid composition
`Phospholipids
`EPA
`DHA
`
`:::: 50 % by weight
`:::: 15 %
`::::10%
`
`:::: 80 % by weight
`::::20%
`::::13%
`
`Copy provided by USPTO from the IFW Image Database on 11/08/2007
`
`RIMFROST EXHIBIT 1036 page 0014
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`
`
`Table 5
`Lipid composition
`Phospholipids
`EPA
`DHA
`
`·.
`
`11
`
`> 90 % by weight
`>23%
`
`~15%
`
`The invention shall not be limited to the shown embodiments and examples.
`
`Copy provided by USPTO from the IFW Image Database on 11/08/2007
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`RIMFROST EXHIBIT 1036 page 0015
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`
`
`P a t e n t
`
`c 1 a
`
`m s
`
`12
`
`s
`
`A process for extracting a substantially total lipid fraction from fresh krill,
`1.
`comprising the steps of:
`a) reducing the water content of krill raw material; and
`b) extracting the water reduced krill material from step a) with supercritical C02
`containing ethanol, methanol, propanol or iso-propanol.
`
`·.
`
`A process of claim 1, wherein step a) comprises washing of the krill raw
`2.
`10 material with ethanol.
`
`A process of claim 1, wherein step a) comprises washing of the krill raw
`3.
`material with ethanol, methanol, propanol or iso-propanol in a weight ratio 1 :0.5 to 1 :5.
`
`15
`
`4.
`A process of claim 1, wherein the krill raw material was heated to 60-100 °C
`before washing.
`
`A process of claim 4, wherein the krill raw material was heated to 70-95 °C
`5.
`before washing.
`
`20
`
`A process of claims 4 or 5, wherein the krill raw material was heated for about 1
`6.
`to 15 minutes before washing.
`
`A process of claim 6, wherein the krill raw material was heated for about 1 to 5
`7.
`25 minutes before washing.
`
`A process of claim 1, wherein step a) comprises bringing the krill raw material
`8.
`in contact with molecular sieve.
`
`30
`
`A process of claim l, wherein the amount of ethanol, methanol, propanol or iso-
`9.
`propanol in step b) is 5-20 % by weight.
`
`A process of claim 9, wherein the amount of ethanol, methanol, propanol or iso-
`10.
`propanol in step b) is 10-15 % by weight.
`
`35
`
`A substantially total lipid fraction comprising triglycerides, astaxanthin and
`11.
`phospholipids obtainable by the process of claim 1.
`
`Copy provided by USPTO from the IFW Image Database on 11/08/2007
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`RIMFROST EXHIBIT 1036 page 0016
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`
`
`13
`
`12.
`
`A lipid fraction of claim 11, being substantially free from oxidised lipids.
`
`A total lipid fraction according to any one of claims 11 or 12, for use as a
`13.
`s medicament and/or as a food supplement.
`
`14.
`A process for separating phospholipids from the other lipids, comprising
`extracting the total lipid fraction obtained by the process of claim I, with pure carbon
`dioxide, or carbon dioxide containing less than 5 % ethanol, methanol, propanol or iso-
`propanol.
`
`10
`
`15.
`
`A phospholipids fraction obtainable by the process of claim 14.
`
`The phospholipids of claim 15, wherein the phospholipids are further
`16.
`transesterified or hydrolysed.
`
`1s
`
`The phospholipids of claim 14, wherein the concentration of omega-3 fatty acids
`17.
`is at least 40 % by weight.
`
`20
`
`2S
`
`•
`
`Copy provided by USPTO from the IFW Image Database on 11/08/2007
`
`RIMFROST EXHIBIT 1036 page 0017
`
`
`
`Abstract
`
`0.nr.P60601677no00
`
`The present invention relates to a process for preparing a substantially total lipid
`fraction from fresh krill, and a process for separating phospholipids from the other
`lipids.
`
`\
`
`•
`
`Copy provided by USPTO from the IFW Image Database on 11/08/2007
`
`RIMFROST EXHIBIT 1036 page 0018
`
`, .,· ....
`
`· ·
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`·· · ·
`
`::..;. '-a:.:.J
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`