# US 10,499,673 B2 · Method for processing crustaceans to produce low fluoride/low trimethyl amine products thereof > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,499,673 B2 - Document ID: US10499673B2 - Status: Granted - Kind: B2 - Application number: 15/171,886 - Filed: 2016-06-02 - Published: 2016-12-01 - Granted: 2019-12-10 - Earliest claimed: 2008-09-12 - Assignees: Rimfrost Technologies AS - Applicants: Rimfrost Technologies AS - Inventors: Inge Bruheim; Stig Rune Remoy; John Cameron - Web page: https://patentgrep.com/patent/US10499673B2 ## CPC - A23L 17/40: Shell-fish - A23D 9/007: characterised by ingredients other than fatty acid triglycerides - A23D 9/013: Other fatty acid esters, e.g. phosphatides - A23D 9/02: characterised by the production or working-up - A23J 1/04: from fish or other sea animals - A23J 3/34: using enzymes - A23K 20/158: Fatty acids; Fats; Products containing oils or fats - A23L 5/23: {by extraction with solvents} - A23L 5/25: {using enzymes} - A23L 17/65: {Addition of, or treatment with, microorganisms or enzymes} - A23L 33/115: Fatty acids or derivatives thereof; Fats or oils - A23L 33/18: Peptides; Protein hydrolysates - C11B 1/025: {by enzymes or microorganisms, living or dead} - C11B 1/10: by extracting - C11B 1/104: {using super critical gases or vapours} - A23V 2002/00: Food compositions, function of food ingredients or processes for food or foodstuffs - Y02P 20/54: using solvents, e.g. supercritical solvents or ionic liquids - A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B) - A23D: EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS (preservation thereof A23B20/00; production, refinement or preservation of animal or vegetable fats or oils C11B, C11C) - A23J: PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS - A23K: FODDER - 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 (drying-oils C09F) - A23V: INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION - Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS ## Abstract The present invention contemplates the creation of a low fluoride crustacean oil processed from a phospholipid-protein complex (PPC) formed immediately upon a crustacean (i.e., for example, krill) catch. Further, the crustacean oil may also have reduced trimethyl amine and/or trimethyl amino oxide content. The process comprises disintegrating the crustaceans into smaller particles, adding water, heating the result, adding enzyme(s) to hydrolyze the disintegrated material, deactivating the enzyme(s), removing solids from the enzymatically processed material to reduce fluoride content of the material, separating and drying the PPC material. Then, using extraction with supercritical CO2 or supercritical dimethyl ether, and/or ethanol as solvents, krill oil, inter alia, is separated from the PPC. In the extraction the krill oil can be separated almost wholly from the feed material. ## Claims ### Claim 1 An extracted crustacean oil composition comprising a total phospholipid content ranging between 39-52 wt % of said composition and less than 1 mg N-trimethylamine/100 g, wherein said total phospholipid content comprises approximately 65 wt % phosphatidylcholine. ### Claim 2 (depends on 1) The crustacean oil composition of claim 1, further comprising approximately 1.4-4.9 wt % phosphatidylethanolamine and less than approximately 2.4 wt % lysophosphatidylcholine of said total phospholipid content. ### Claim 3 (depends on 1) The crustacean oil composition of claim 1, further comprising, triglycerides, neutral lipids, and approximately 20-30 wt % polyunsaturated omega-3 fatty acids. ### Claim 4 (depends on 1) The crustacean oil composition of claim 1, further comprising approximately 12 wt % eicosapentaenoic fatty acid. ### Claim 5 (depends on 1) The crustacean oil composition of claim 1, further comprising approximately 6 wt % docosahexaenoic fatty acid. ### Claim 6 (depends on 1) The crustacean oil composition of claim 1, further comprising at least 115 mg/kg astaxanthin. ### Claim 7 (depends on 1) The crustacean oil composition of claim 1, wherein said crustacean oil composition is a krill oil. ### Claim 8 (depends on 1) The crustacean oil composition of claim 1, wherein said crustacean oil comprises less than approximately 0.5 ppm fluoride. ### Claim 9 (depends on 1) The crustacean oil of claim 1, wherein said clear red color results from a minimal formation of a dark brown color. ### Claim 10 (depends on 9) The crustacean oil of claim 9, wherein said minimal formation of said dark brown color is due to tertiary oxidation product formation or astaxanthin degradation. ### Claim 11 (depends on 1) The crustacean oil composition of claim 1, wherein said composition has a clear red color. ### Claim 12 (depends on 1) The crustacean oil composition of claim 1, wherein said crustacean oil composition is an 80-90% efficient extraction product of a crustacean phospholipid-protein complex (PPC). ### Claim 13 (depends on 12) The crustacean oil composition of claim 12, wherein said PPC comprises approximately 2 wt % polyunsaturated omega-6 fatty acids. ### Claim 14 (depends on 12) The crustacean oil composition of claim 12, wherein said PPC comprises a peroxide level of less than 0.1% (mEq/kg). ### Claim 15 (depends on 12) The crustacean oil composition of claim 12, wherein said PPC comprises a cholesterol level of between approximately 1-2% (w/w). ### Claim 16 (depends on 12) The crustacean oil composition of claim 12, wherein said PPC comprises a cholesterol ester of less than 0.5% (w/w). ### Claim 17 An extracted crustacean oil comprising at least 40 wt % total phospholipids and less than 20 mg N-trimethylamine oxide/100 g of said crustacean oil and less than 1 mg N-trimethylamine/100 g of said crustacean oil, wherein said total phospholipids comprise at least 75 wt % phosphatidylcholine and at least 2% phosphatidylethanolamine of the total phospholipids. ### Claim 18 (depends on 17) The crustacean oil composition of claim 17, wherein said trimethylamine is less than approximately 0.001% (w/w). ### Claim 19 (depends on 17) The crustacean oil composition of claim 17, wherein said trimethylamine oxide is less than approximately 0.02% (w/w). ### Claim 20 (depends on 17) The crustacean oil composition of claim 17, further comprising triglycerides, neutral lipids and approximately 20-30 wt % polyunsaturated omega-3 fatty acids. ### Claim 21 (depends on 17) The crustacean oil composition of claim 17, further comprising approximately 12 wt % eicosapentaenoic fatty acid. ### Claim 22 (depends on 17) The crustacean oil composition of claim 17, further comprising approximately 6 wt % docosahexaenoic fatty acid. ### Claim 23 (depends on 17) The crustacean oil composition of claim 17, further comprising at least 115 mg/kg astaxanthin. ### Claim 24 (depends on 17) The crustacean oil composition of claim 17, wherein said crustacean oil composition is a krill oil. ### Claim 25 (depends on 17) The crustacean oil composition of claim 17, wherein said crustacean oil comprises less than approximately 0.5 ppm fluoride. ### Claim 26 (depends on 17) The crustacean oil composition of claim 17, wherein said crustacean oil composition has a clear red color. ### Claim 27 (depends on 26) The crustacean oil of claim 26, wherein said clear red color results from a minimal formation of a dark brown color. ### Claim 28 (depends on 27) The crustacean oil of claim 27, wherein said minimal formation of said dark brown color is due to tertiary oxidation product formation or astaxanthin degradation. ### Claim 29 (depends on 17) The crustacean oil composition of claim 17, wherein said crustacean oil composition is an 80-90% efficient extraction product of a crustacean phospholipid-protein complex (PPC). ### Claim 30 (depends on 29) The crustacean oil composition of claim 29, wherein said PPC comprises approximately 2 wt % polyunsaturated omega-6 fatty acids. ### Claim 31 (depends on 29) The crustacean oil composition of claim 29, wherein said PPC comprises a peroxide level of less than 0.1% (mEq/kg). ### Claim 32 (depends on 29) The crustacean oil composition of claim 29, wherein said PPC comprises a cholesterol level of between approximately 1-2% (w/w). ### Claim 33 (depends on 29) The crustacean oil composition of claim 29, wherein said PPC comprises a cholesterol ester of less than 0.5% (w/w).