US20140275596A1 - Algal omega 7 and algal omega 3 blend compositions - Google Patents

Algal omega 7 and algal omega 3 blend compositions Download PDF

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US20140275596A1
US20140275596A1 US14/025,756 US201314025756A US2014275596A1 US 20140275596 A1 US20140275596 A1 US 20140275596A1 US 201314025756 A US201314025756 A US 201314025756A US 2014275596 A1 US2014275596 A1 US 2014275596A1
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approximately
algal
fatty acid
composition
saturated
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James Astwood
Leslie van der Meulen
Michelle Collins
Jeffrey Gerard Hippler
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Aurora Algae Inc
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Aurora Algae Inc
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Priority to US14/025,756 priority Critical patent/US20140275596A1/en
Priority to US14/025,772 priority patent/US9445619B2/en
Assigned to AURORA ALGAE, INC. reassignment AURORA ALGAE, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: VAN DER MEULEN, LESLIE, HIPPLER, Jeffrey Gerard, ASTWOOD, James, COLLINS, Michelle L.
Publication of US20140275596A1 publication Critical patent/US20140275596A1/en
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    • 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
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Definitions

  • This invention relates to algal biochemistry, and more specifically, to blended algal oil compositions.
  • exemplary algal fatty acid compositions comprising by dry weight approximately 0.5% to approximately 99% C20:5 n3 Eicosapentaenoic acid (EPA) and approximately 0.5% to approximately 99% C16:1 n7 palmitoleic acid (POA).
  • Further exemplary algal fatty acid compositions may comprise (in addition to the above) one or more of the following by dry weight: between approximately 0% and 99% arachidonic acid; between approximately 0% and 99% docosahexaenoic acid; and/or less than approximately 10% saturated fatty acids (including 0% saturated fatty acids or substantially saturated fatty acid free).
  • the exemplary algal fatty acid compositions herein may be unsaturated (i.e.
  • an exemplary saturated fatty acyl moiety-rich algal composition comprising by total weight approximately 50% POA, approximately 50% PA and substantially no DHA.
  • the exemplary saturated fatty acyl moiety-rich algal compositions may be processed from an exemplary total algal oil composition comprising by total weight approximately 30% EPA, approximately 27% POA, approximately 0% to 20% saturated fats, less than approximately 10% ARA, and substantially no DHA.
  • the exemplary saturated fatty acyl moiety-rich algal compositions may also be processed from an exemplary total algal oil composition comprising by total weight between approximately 0% and 99% EPA, and one or more of the following: between approximately 0% and 99% POA, less than approximately 20% saturated fats (including 0% saturated fats or substantially saturated fat free), between approximately 0% and 99% ARA, and/or between approximately 0% and 99% DHA.
  • the saturated fats may comprise PA.
  • saturated fatty acyl moiety-rich algal compositions may be in a form of an ethyl ester (EE), a mono, di- or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), free fatty Acid (FFA), or a sulfoquinovosyl diacylglycerol (SQDG).
  • EE ethyl ester
  • MAG mono, di- or triacylglycerol
  • PL phospholipid
  • GL galactolipid
  • FFA free fatty Acid
  • SQLDG sulfoquinovosyl diacylglycerol
  • exemplary algal fatty acid compositions comprising by dry weight approximately 0.5% to approximately 99% C20:5 n3 Eicosapentaenoic acid (EPA) and approximately 0.5% to approximately 99% C16:1 n7 palmitoleic acid (POA).
  • Further exemplary algal fatty acid compositions may comprise one or more of the following by dry weight: less than approximately 5% arachidonic acid; substantially no docosahexaenoic acid; and/or less than approximately 20% saturated fatty acids.
  • the exemplary algal fatty acid compositions herein may be unsaturated (i.e.
  • an exemplary saturated fatty acyl moiety-rich algal composition comprising by total weight approximately 50% POA, approximately 50% PA and substantially no DHA.
  • the exemplary saturated fatty acyl moiety-rich algal compositions may be processed from an exemplary total algal oil composition comprising by total weight approximately 30% EPA, approximately 27% POA, approximately 0% to 20% saturated fats, less than approximately 10% ARA, and substantially no DHA.
  • saturated fatty acyl moiety-rich algal compositions may be in a form of an ethyl ester (EE), a mono, di- or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), free fatty Acid (FFA), or a sulfoquinovosyl diacylglycerol (SQDG).
  • EE ethyl ester
  • MAG mono, di- or triacylglycerol
  • PL phospholipid
  • GL galactolipid
  • FFA free fatty Acid
  • SQLDG sulfoquinovosyl diacylglycerol
  • FIG. 1 is a flow chart for an exemplary process for removing saturated fats from whole cut oil to produce a low-saturated product that comprises O3 EPA esters, O7 palmitoleate esters, and O6 arachidonic acid esters.
  • FIG. 2 is a flow chart for an exemplary process for mixing a concentrated EPA O3 stream with a concentrated TAO O7 stream to produce a mixed stream.
  • a fatty acid is a carboxylic acid with a long aliphatic tail (chain), which is either saturated or unsaturated. Most naturally occurring fatty acids have a chain of an even number of carbon atoms, from 4 to 28. Saturated fatty acids have no double bonds between carbon atoms. Unsaturated fatty acids have one or more double bonds between carbon atoms. When counting from the terminal methyl carbon toward the carbonyl carbon on an unsaturated fatty acid, the first double bond signifies the omega double bond, such as observed in omega 3, omega 6, or omega 7 fatty acids.
  • Palmitoleic acid is an omega-7 monounsaturated fatty acid with a 16-carbon chain with one double bond, denoted as C16:1 n7. A beneficial fatty acid, it has been shown to suppress inflammation. Dietary sources of omega-7 are found in animal and plant sources, including sea buckthorn berries, macadamia nuts, cold water fish and dairy fat. These sources, however, are not concentrated and/or purified sources of POA and often contain a mixed fatty acid profile of saturated and polyunsaturated fats.
  • Palmitic acid is a saturated fatty acid with a 16-carbon chain and no double bonds, denoted as C16:0. Consumption of saturated fats such as palmitic acid is believed to increase the risk of developing diabetes, obesity, stroke and cardiovascular diseases.
  • Alpha linolenic acid is an omega-3 polyunsaturated fatty acid (PUFA) with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the methyl end of the fatty acid chain, denoted as C18:3 n3.
  • PUFA polyunsaturated fatty acid
  • Oleic acid is an omega-9 monounsaturated fatty acid with an 18-carbon chain with one double bond denoted as C18:1 n9.
  • OA is a main component of olive oil, macadamia oil and other monounsaturated fats.
  • Arachidonic acid is an omega-6 PUFA with a 20-carbon chain and four cis-double bonds; the first double bond is located at the sixth carbon from the omega end.
  • ARA is also denoted as C20:4 n6.
  • Examples of dietary sources of omega-6 PUFAs include refined vegetable oils, such as corn and soy oil, seeds and nuts and the oils extracted from them. Consumption is therefore sufficient in the average diet.
  • Eicosapentaenoic acid is an omega-3 fatty acid PUFA with the following connotation C20:5 n3. It is a carboxylic acid with a 20-carbon chain and five cis double bonds; the first double bond is located at the third carbon from the omega end.
  • Docosahexaenoic acid is an omega-3 fatty acid PUFA. It is a carboxylic acid with a 22-carbon chain and six cis double bonds; the first double bond is located at the third carbon from the omega end. DHA is also denoted as C22:6 n3.
  • exemplary algal fatty acid compositions comprising by dry weight approximately 0.5% to approximately 99% C20:5 n3 Eicosapentaenoic acid (EPA) and approximately 0.5% to approximately 99% C16:1 n7 palmitoleic acid (POA).
  • Further exemplary algal fatty acid compositions may comprise (in addition to the above) one or more of the following by dry weight: between approximately 0% and 99% arachidonic acid; between approximately 0% and 99% docosahexaenoic acid; and/or less than approximately 20% saturated fatty acids (including 0% saturated fatty acids or substantially saturated fatty acid free).
  • the exemplary algal fatty acid compositions herein may be unsaturated (i.e. removing the saturated fatty acids from the monounsaturated and/or polyunsaturated fatty acids) from an exemplary saturated fatty acyl moiety-rich algal composition comprising by total weight approximately 50% POA, approximately 50% PA and substantially no DHA.
  • the exemplary saturated fatty acyl moiety-rich algal compositions may be processed from an exemplary total algal oil composition comprising by total weight approximately 30% EPA, approximately 27% POA, approximately 0% to 20% saturated fats, less than approximately 10% ARA, and substantially no DHA.
  • the exemplary saturated fatty acyl moiety-rich algal compositions may also be processed from an exemplary total algal oil composition comprising by total weight between approximately 0% and 99% EPA, and one or more of the following: between approximately 0% and 99% POA, less than approximately 20% saturated fats (including 0% saturated fats or substantially saturated fat free), between approximately 0% and 99% ARA, and/or between approximately 0% and 99% DHA.
  • the saturated fats may comprise PA.
  • Further exemplary saturated fatty acyl moiety-rich algal compositions may be in a form of an ethyl ester (EE), a mono, di- or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), free fatty Acid (FFA), or a sulfoquinovosyl diacylglycerol (SQDG).
  • EE ethyl ester
  • MAG mono, di- or triacylglycerol
  • PL phospholipid
  • GL galactolipid
  • FFA free fatty Acid
  • SQLDG sulfoquinovosyl diacylglycerol
  • the exemplary compositions herein may be processed from total algal oil compositions comprising by total weight between approximately 0% and 99% OA and none, or one or more of the following: between approximately 0% and 99% EPA, between approximately 0% and 99% POA, less than approximately 20% saturated fats (including 0% saturated fats or substantially saturated fat free), between approximately 0% and 99% ARA, and/or between approximately 0% and 99% DHA.
  • the saturated fats may comprise PA.
  • saturated fatty acyl moiety-rich algal compositions may be in a form of an ethyl ester (EE), a mono, di- or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), free fatty Acid (FFA), or a sulfoquinovosyl diacylglycerol (SQDG).
  • EE ethyl ester
  • MAG mono, di- or triacylglycerol
  • PL phospholipid
  • GL galactolipid
  • FFA free fatty Acid
  • SQLDG sulfoquinovosyl diacylglycerol
  • exemplary algal fatty acid compositions comprising by dry weight approximately 0.5% to approximately 99% C20:5 n3 Eicosapentaenoic acid (EPA) and approximately 0.5% to approximately 99% C16:1 n7 palmitoleic acid (POA).
  • Further exemplary algal fatty acid compositions may comprise one or more of the following by dry weight: less than approximately 5% arachidonic acid; substantially no docosahexaenoic acid; and/or less than approximately 20% saturated fatty acids.
  • the exemplary algal fatty acid compositions herein may be unsaturated (i.e.
  • an exemplary saturated fatty acyl moiety-rich algal composition comprising by total weight approximately 50% POA, approximately 50% PA and substantially no DHA.
  • the exemplary saturated fatty acyl moiety-rich algal compositions may be processed from an exemplary total algal oil composition comprising by total weight approximately 30% EPA, approximately 27% POA, approximately 0% to 20% saturated fats, less than approximately 10% ARA, and substantially no DHA.
  • the total algal oil compositions may be processed from an algal biomass composition comprising approximately 10% lipids, at least approximately 15% carbohydrates, at least approximately 25% protein, at least approximately 3% moisture and at least approximately 5% ash.
  • saturated fatty acyl moiety-rich algal compositions may be in a form of an ethyl ester (EE), a mono, di- or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), free fatty Acid (FFA), or a sulfoquinovosyl diacylglycerol (SQDG).
  • EE ethyl ester
  • MAG mono, di- or triacylglycerol
  • PL phospholipid
  • GL galactolipid
  • FFA free fatty Acid
  • SQLDG sulfoquinovosyl diacylglycerol
  • Table 1 below shows some of the exemplary blends provided herein.
  • the exemplary compositions herein may include algal fatty acid compositions comprising by dry weight approximately 0.5% to approximately 99% C18:1n9 Oleic acid (OA) and none, one or both of the following: 0.5% to approximately 99% C20:5 n3 Eicosapentaenoic acid (EPA), and approximately 0.5% to approximately 99% C16:1 n7 palmitoleic acid (POA).
  • Further exemplary algal fatty acid compositions may comprise (in addition to the above) one or more of the following by dry weight: between approximately 0% and 99% arachidonic acid; between approximately 0% and 99% docosahexaenoic acid; and/or less than approximately 20% saturated fatty acids (including 0% saturated fatty acids or substantially saturated fatty acid free).
  • the saturated fats may comprise PA.
  • Further exemplary saturated fatty acyl moiety-rich algal compositions may be in a form of an ethyl ester (EE), a mono, di- or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), free fatty acid (FFA), or a sulfoquinovosyl diacylglycerol (SQDG).
  • EE ethyl ester
  • MAG mono, di- or triacylglycerol
  • PL phospholipid
  • GL galactolipid
  • FFA free fatty acid
  • SQLDG sulfoquinovosyl diacylglycerol
  • Algae are mostly aquatic photosynthetic organisms that range from microscopic flagellate to giant kelp. Algae may be loosely grouped into seven categories: Euglenophyta (euglenoids), Chrysophyta (golden-brown algae), Pyrrophyta (fire algae), Dinoflagellata, Chlorophyta (green algae), Rhodophyta (red algae), Paeophyta (brown algae), and Xanthophyta (yellow-green algae).
  • Lipid extracted from any algae genus may be used in the various embodiments of the present invention, including Amphora, Anabaena, Anikstrodesmis, Botryococcus, Chaetoceros, Chlorella, Chlorococcum, Cyclotella, Cylindrotheca, Dunaliella, Emiliania, Euglena, Glossomastix, Haematococcus, Isochrysis, Monochrysis, Monoraphidium, Nannochloris, Nannochloropsis, Navicula, Nephrochloris, Nephroselmis, Nitzschia, Nodularia, Nostoc, Oochromonas, Oocystis, Oscillatoria, Pavlova, Phaeodactylum, Picochloris, Platymonas, Pleurochrysis, Porphyra, Pseudoanabaena, Pyramimonas, Scenedesmus, Stichococcus, Synecho
  • FIG. 1 is a flow chart for an exemplary process for removing saturated fats from whole cut oil to produce a low-saturated product which comprises O3 EPA esters, O7 palmitoleate esters, and O6 Arachidonic acid esters.
  • U.S. Non-Provisional patent application Ser. No. ______ filed on ______ concurrently with the present application and titled “Conversion of Free Fatty Acids to Ethyl Esters,” which is hereby incorporated by reference discusses how whole-cut algal oil is produced from algae.
  • This oil is a mixture which includes esters of Arachidonic acid (ARA), palmitoleic acid (POA), palmitic acid, (PA) and eicosapentaenoic acid (EPA).
  • ARA Arachidonic acid
  • POA palmitoleic acid
  • PA palmitic acid
  • EPA eicosapentaenoic acid
  • solvent may be added to the mixture of esters.
  • the solvent may be an alcohol such as methanol, ethanol, or isopropanol.
  • the solvent may be a hydrocarbon such as a hexane, heptane, or octane.
  • the solvent may be an aldehyde or ketone such as acetone or diethyl ketone, or the solvent may be an ester or ether, such as ethyl acetate or dimethyl ether.
  • the solvent may be in the form of a liquid or a supercritical carbon dioxide.
  • the solvent may be a mixture of these solvents or solvent classes. Or the separation may be performed without a solvent.
  • the mixture is chilled to form crystals.
  • the temperature to which the mixture is chilled is dependent upon the composition of the mixture, with temperatures ranging from approximately ⁇ 30° C. to +15° C.
  • the mixture is held within this temperature range while the crystals are formed.
  • the mixture may be cooled quickly or slowly to the target temperature.
  • the mixture is filtered to separate the crystals from the liquid phase mixture.
  • this step needs to be performed in such a way so as to minimize the melting or dissolution of the crystals. This is usually accomplished by performing the filtration at a reduced temperature. This filtration is usually done by maintaining a negative-pressure vacuum downstream of the filter.
  • the crystalline phase is rich in the saturated PA, while the liquid phase has a reduced PA concentration.
  • the mixture may be recrystallized and re-filtered at a lower temperature to crystallize out more saturated fatty moieties, if desired. This may be repeated numerous times.
  • the mixture may be heated (and optionally held under vacuum) and the solvent may be stripped from the ester mixture. This results in an O3, O6, O7 mixture with a reduced saturated moiety level.
  • FIG. 2 is a flow chart for an exemplary process for mixing a concentrated EPA O3 stream with a concentrated TAO O7 stream to produce a mixed stream.
  • a concentrated omega-3 EPA mixture is produced from algal oil or other sources. This is described in U.S. Provisional Patent Application Ser. No. 61/800,114 filed on Mar. 15, 2013 and titled “(EPA) Algal Biomass and Oil Compositions and Impact on Health,” which is hereby incorporated by reference.
  • a concentrated omega-7 POA mixture is produced from algal oil or other sources. This is described in U.S. Non-Provisional patent application Ser. No. ______filed on ______ concurrently with the present application and titled “Algal Omega 7 Compositions,” which is hereby incorporated by reference.
  • the two concentrated mixtures are combined together in the desired proportion.
  • the proportion of either of the mixtures may range from zero to one hundred percent.
  • the combined mixture is mixed to produce a homogeneous mixture.
  • the POA and the EPA mixtures are completely miscible in each other, thus no special mixing requirements are needed. They can be shaken, stirred, agitated intensely, or agitated gently.
  • the various algal oil compositions provided herein may further be in ethyl ester form.
  • ethyl esters are derived by reacting free fatty acids with ethanol. Called -esterification, the resulting ethyl ester allows for the fractional distillation (concentration) of the long chain fatty acids at lower temperatures. This step allows for the selective concentration of the fatty acids to levels greater than found in nature.
  • the ethyl ester forms of the various exemplary algal oil compositions provided herein may be converted to a triglyceride form by performing an enzymatic reaction with the ethyl ester form in the presence of glycerol, heating under a vacuum, and filtering out the enzymes.
  • immobilized lipase enzymes such as that isolated from Candida Antarctica and/or commercially available from Novozyme or Sigma Aldrich may be used.

Abstract

Provided herein are exemplary algal fatty acid compositions comprising by dry weight approximately 0.5% to approximately 99% C20:5 n3 Eicosapentaenoic acid (EPA) and approximately 0.5% to approximately 99% C16:1 n7 palmitoleic acid (POA). Further exemplary algal fatty acid compositions may comprise (in addition to the above) one or more of the following by dry weight: between approximately 0% and 99% arachidonic acid; between approximately 0% and 99% docosahexaenoic acid; and/or less than approximately 10% saturated fatty acids (including 0% saturated fatty acids or substantially saturated fatty acid free). Further exemplary saturated fatty acyl moiety-rich algal compositions may be in a form of an ethyl ester (EE), a mono, di- or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), free fatty Acid (FFA), or a sulfoquinovosyl diacylglycerol (SQDG).

Description

    CROSS-REFERENCE TO RELATED APPLICATIONS
  • The present application claims the benefit and priority of U.S. Provisional Patent Application Ser. No. 61/800,114 filed on Mar. 15, 2013 and titled “(EPA) Algal Biomass and Oil Compositions and Impact on Health,” which is hereby incorporated by reference.
  • The present application claims the benefit and priority of U.S. Provisional Patent Application Ser. No. 61/800,029 filed on Mar. 15, 2013 and titled “Microalga Species and Industrial Applications,” which is hereby incorporated by reference.
  • The present application is related to U.S. Non-Provisional patent application Ser. No. ______ filed on ______ concurrently with the present application and titled “Algal Omega 7 Compositions,” which is hereby incorporated by reference.
  • The present application is related to U.S. Non-Provisional patent application Ser. No. ______ filed on ______ concurrently with the present application and titled “Algal Oil Compositions,” which is hereby incorporated by reference.
  • The present application is related to U.S. Non-Provisional patent application Ser. No. ______ filed on ______ concurrently with the present application and titled “Conversion of Free Fatty Acids to Ethyl Esters,” which is hereby incorporated by reference.
  • The present application is related to U.S. Non-Provisional patent application Ser. No. ______ filed on ______ concurrently with the present application and titled “Compositions and Methods for Utilization of Algal Compounds,” which is hereby incorporated by reference.
    • BACKGROUND OF THE INVENTION Field of the Invention
  • This invention relates to algal biochemistry, and more specifically, to blended algal oil compositions.
    • SUMMARY OF THE INVENTION
  • Provided herein are exemplary algal fatty acid compositions comprising by dry weight approximately 0.5% to approximately 99% C20:5 n3 Eicosapentaenoic acid (EPA) and approximately 0.5% to approximately 99% C16:1 n7 palmitoleic acid (POA). Further exemplary algal fatty acid compositions may comprise (in addition to the above) one or more of the following by dry weight: between approximately 0% and 99% arachidonic acid; between approximately 0% and 99% docosahexaenoic acid; and/or less than approximately 10% saturated fatty acids (including 0% saturated fatty acids or substantially saturated fatty acid free). The exemplary algal fatty acid compositions herein may be unsaturated (i.e. removing the saturated fatty acids from the monounsaturated and/or polyunsaturated fatty acids) from an exemplary saturated fatty acyl moiety-rich algal composition comprising by total weight approximately 50% POA, approximately 50% PA and substantially no DHA. Additionally, the exemplary saturated fatty acyl moiety-rich algal compositions may be processed from an exemplary total algal oil composition comprising by total weight approximately 30% EPA, approximately 27% POA, approximately 0% to 20% saturated fats, less than approximately 10% ARA, and substantially no DHA. The exemplary saturated fatty acyl moiety-rich algal compositions may also be processed from an exemplary total algal oil composition comprising by total weight between approximately 0% and 99% EPA, and one or more of the following: between approximately 0% and 99% POA, less than approximately 20% saturated fats (including 0% saturated fats or substantially saturated fat free), between approximately 0% and 99% ARA, and/or between approximately 0% and 99% DHA. According to further exemplary total algal oil compositions, the saturated fats may comprise PA. Further exemplary saturated fatty acyl moiety-rich algal compositions may be in a form of an ethyl ester (EE), a mono, di- or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), free fatty Acid (FFA), or a sulfoquinovosyl diacylglycerol (SQDG).
  • Provided herein are exemplary algal fatty acid compositions comprising by dry weight approximately 0.5% to approximately 99% C20:5 n3 Eicosapentaenoic acid (EPA) and approximately 0.5% to approximately 99% C16:1 n7 palmitoleic acid (POA). Further exemplary algal fatty acid compositions may comprise one or more of the following by dry weight: less than approximately 5% arachidonic acid; substantially no docosahexaenoic acid; and/or less than approximately 20% saturated fatty acids. The exemplary algal fatty acid compositions herein may be unsaturated (i.e. removing the saturated fatty acids from the monounsaturated and/or polyunsaturated fatty acids) from an exemplary saturated fatty acyl moiety-rich algal composition comprising by total weight approximately 50% POA, approximately 50% PA and substantially no DHA. Additionally, the exemplary saturated fatty acyl moiety-rich algal compositions may be processed from an exemplary total algal oil composition comprising by total weight approximately 30% EPA, approximately 27% POA, approximately 0% to 20% saturated fats, less than approximately 10% ARA, and substantially no DHA. Further exemplary saturated fatty acyl moiety-rich algal compositions may be in a form of an ethyl ester (EE), a mono, di- or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), free fatty Acid (FFA), or a sulfoquinovosyl diacylglycerol (SQDG).
    • BRIEF DESCRIPTION OF THE DRAWINGS
  • FIG. 1 is a flow chart for an exemplary process for removing saturated fats from whole cut oil to produce a low-saturated product that comprises O3 EPA esters, O7 palmitoleate esters, and O6 arachidonic acid esters.
  • FIG. 2 is a flow chart for an exemplary process for mixing a concentrated EPA O3 stream with a concentrated TAO O7 stream to produce a mixed stream.
    •  DETAILED DESCRIPTION OF THE INVENTION
  • A fatty acid is a carboxylic acid with a long aliphatic tail (chain), which is either saturated or unsaturated. Most naturally occurring fatty acids have a chain of an even number of carbon atoms, from 4 to 28. Saturated fatty acids have no double bonds between carbon atoms. Unsaturated fatty acids have one or more double bonds between carbon atoms. When counting from the terminal methyl carbon toward the carbonyl carbon on an unsaturated fatty acid, the first double bond signifies the omega double bond, such as observed in omega 3, omega 6, or omega 7 fatty acids.
  • Palmitoleic acid (POA) is an omega-7 monounsaturated fatty acid with a 16-carbon chain with one double bond, denoted as C16:1 n7. A beneficial fatty acid, it has been shown to suppress inflammation. Dietary sources of omega-7 are found in animal and plant sources, including sea buckthorn berries, macadamia nuts, cold water fish and dairy fat. These sources, however, are not concentrated and/or purified sources of POA and often contain a mixed fatty acid profile of saturated and polyunsaturated fats.
  • Palmitic acid (PA) is a saturated fatty acid with a 16-carbon chain and no double bonds, denoted as C16:0. Consumption of saturated fats such as palmitic acid is believed to increase the risk of developing diabetes, obesity, stroke and cardiovascular diseases.
  • Alpha linolenic acid (ALA) is an omega-3 polyunsaturated fatty acid (PUFA) with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the methyl end of the fatty acid chain, denoted as C18:3 n3.
  • Oleic acid (OA) is an omega-9 monounsaturated fatty acid with an 18-carbon chain with one double bond denoted as C18:1 n9. OA is a main component of olive oil, macadamia oil and other monounsaturated fats.
  • Arachidonic acid (ARA) is an omega-6 PUFA with a 20-carbon chain and four cis-double bonds; the first double bond is located at the sixth carbon from the omega end. ARA is also denoted as C20:4 n6. Examples of dietary sources of omega-6 PUFAs include refined vegetable oils, such as corn and soy oil, seeds and nuts and the oils extracted from them. Consumption is therefore sufficient in the average diet.
  • Eicosapentaenoic acid (EPA) is an omega-3 fatty acid PUFA with the following connotation C20:5 n3. It is a carboxylic acid with a 20-carbon chain and five cis double bonds; the first double bond is located at the third carbon from the omega end.
  • Docosahexaenoic acid (DHA) is an omega-3 fatty acid PUFA. It is a carboxylic acid with a 22-carbon chain and six cis double bonds; the first double bond is located at the third carbon from the omega end. DHA is also denoted as C22:6 n3.
  • Provided herein are exemplary algal fatty acid compositions comprising by dry weight approximately 0.5% to approximately 99% C20:5 n3 Eicosapentaenoic acid (EPA) and approximately 0.5% to approximately 99% C16:1 n7 palmitoleic acid (POA). Further exemplary algal fatty acid compositions may comprise (in addition to the above) one or more of the following by dry weight: between approximately 0% and 99% arachidonic acid; between approximately 0% and 99% docosahexaenoic acid; and/or less than approximately 20% saturated fatty acids (including 0% saturated fatty acids or substantially saturated fatty acid free). The exemplary algal fatty acid compositions herein may be unsaturated (i.e. removing the saturated fatty acids from the monounsaturated and/or polyunsaturated fatty acids) from an exemplary saturated fatty acyl moiety-rich algal composition comprising by total weight approximately 50% POA, approximately 50% PA and substantially no DHA.
  • Additionally, the exemplary saturated fatty acyl moiety-rich algal compositions may be processed from an exemplary total algal oil composition comprising by total weight approximately 30% EPA, approximately 27% POA, approximately 0% to 20% saturated fats, less than approximately 10% ARA, and substantially no DHA. The exemplary saturated fatty acyl moiety-rich algal compositions may also be processed from an exemplary total algal oil composition comprising by total weight between approximately 0% and 99% EPA, and one or more of the following: between approximately 0% and 99% POA, less than approximately 20% saturated fats (including 0% saturated fats or substantially saturated fat free), between approximately 0% and 99% ARA, and/or between approximately 0% and 99% DHA. According to further exemplary total algal oil compositions, the saturated fats may comprise PA. Further exemplary saturated fatty acyl moiety-rich algal compositions may be in a form of an ethyl ester (EE), a mono, di- or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), free fatty Acid (FFA), or a sulfoquinovosyl diacylglycerol (SQDG).
  • The exemplary compositions herein may be processed from total algal oil compositions comprising by total weight between approximately 0% and 99% OA and none, or one or more of the following: between approximately 0% and 99% EPA, between approximately 0% and 99% POA, less than approximately 20% saturated fats (including 0% saturated fats or substantially saturated fat free), between approximately 0% and 99% ARA, and/or between approximately 0% and 99% DHA. According to further exemplary total algal oil compositions, the saturated fats may comprise PA. Further exemplary saturated fatty acyl moiety-rich algal compositions may be in a form of an ethyl ester (EE), a mono, di- or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), free fatty Acid (FFA), or a sulfoquinovosyl diacylglycerol (SQDG).
  • Provided herein are exemplary algal fatty acid compositions comprising by dry weight approximately 0.5% to approximately 99% C20:5 n3 Eicosapentaenoic acid (EPA) and approximately 0.5% to approximately 99% C16:1 n7 palmitoleic acid (POA). Further exemplary algal fatty acid compositions may comprise one or more of the following by dry weight: less than approximately 5% arachidonic acid; substantially no docosahexaenoic acid; and/or less than approximately 20% saturated fatty acids. The exemplary algal fatty acid compositions herein may be unsaturated (i.e. removing the saturated fatty acids from the monounsaturated and/or polyunsaturated fatty acids) from an exemplary saturated fatty acyl moiety-rich algal composition comprising by total weight approximately 50% POA, approximately 50% PA and substantially no DHA. Additionally, the exemplary saturated fatty acyl moiety-rich algal compositions may be processed from an exemplary total algal oil composition comprising by total weight approximately 30% EPA, approximately 27% POA, approximately 0% to 20% saturated fats, less than approximately 10% ARA, and substantially no DHA.
  • According to various exemplary methods, the total algal oil compositions may be processed from an algal biomass composition comprising approximately 10% lipids, at least approximately 15% carbohydrates, at least approximately 25% protein, at least approximately 3% moisture and at least approximately 5% ash.
  • Further exemplary saturated fatty acyl moiety-rich algal compositions may be in a form of an ethyl ester (EE), a mono, di- or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), free fatty Acid (FFA), or a sulfoquinovosyl diacylglycerol (SQDG).
  • Table 1 below shows some of the exemplary blends provided herein.
  • TABLE 1
    Example Blends
    Blend Omega-3 Omega-7
    Options 65% EPA (%) 70% POA (%)
    1 0 70
    2 25 50
    3 35 35
    4 50 25
    5 65 0
  • The exemplary compositions herein may include algal fatty acid compositions comprising by dry weight approximately 0.5% to approximately 99% C18:1n9 Oleic acid (OA) and none, one or both of the following: 0.5% to approximately 99% C20:5 n3 Eicosapentaenoic acid (EPA), and approximately 0.5% to approximately 99% C16:1 n7 palmitoleic acid (POA). Further exemplary algal fatty acid compositions may comprise (in addition to the above) one or more of the following by dry weight: between approximately 0% and 99% arachidonic acid; between approximately 0% and 99% docosahexaenoic acid; and/or less than approximately 20% saturated fatty acids (including 0% saturated fatty acids or substantially saturated fatty acid free). According to further exemplary total algal oil compositions, the saturated fats may comprise PA. Further exemplary saturated fatty acyl moiety-rich algal compositions may be in a form of an ethyl ester (EE), a mono, di- or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), free fatty acid (FFA), or a sulfoquinovosyl diacylglycerol (SQDG).
  • In various embodiments, various algae species may be the source of the compositions provided herein. Algae are mostly aquatic photosynthetic organisms that range from microscopic flagellate to giant kelp. Algae may be loosely grouped into seven categories: Euglenophyta (euglenoids), Chrysophyta (golden-brown algae), Pyrrophyta (fire algae), Dinoflagellata, Chlorophyta (green algae), Rhodophyta (red algae), Paeophyta (brown algae), and Xanthophyta (yellow-green algae). Lipid extracted from any algae genus may be used in the various embodiments of the present invention, including Amphora, Anabaena, Anikstrodesmis, Botryococcus, Chaetoceros, Chlorella, Chlorococcum, Cyclotella, Cylindrotheca, Dunaliella, Emiliania, Euglena, Glossomastix, Haematococcus, Isochrysis, Monochrysis, Monoraphidium, Nannochloris, Nannochloropsis, Navicula, Nephrochloris, Nephroselmis, Nitzschia, Nodularia, Nostoc, Oochromonas, Oocystis, Oscillatoria, Pavlova, Phaeodactylum, Picochloris, Platymonas, Pleurochrysis, Porphyra, Pseudoanabaena, Pyramimonas, Scenedesmus, Stichococcus, Synechococcus, Synechocystis, Tetraselmis, Thalassiosira, and Trichodesmium.
  • FIG. 1 is a flow chart for an exemplary process for removing saturated fats from whole cut oil to produce a low-saturated product which comprises O3 EPA esters, O7 palmitoleate esters, and O6 Arachidonic acid esters. U.S. Non-Provisional patent application Ser. No. ______ filed on ______ concurrently with the present application and titled “Conversion of Free Fatty Acids to Ethyl Esters,” which is hereby incorporated by reference discusses how whole-cut algal oil is produced from algae. This oil is a mixture which includes esters of Arachidonic acid (ARA), palmitoleic acid (POA), palmitic acid, (PA) and eicosapentaenoic acid (EPA). In certain applications, it is desirable to remove the PA from the other components. This can be done by selective crystallization, also known as winterization in the biodiesel area.
  • At step 110, solvent may be added to the mixture of esters. According to various exemplary methods, the solvent may be an alcohol such as methanol, ethanol, or isopropanol. In other exemplary methods, the solvent may be a hydrocarbon such as a hexane, heptane, or octane. According to further exemplary methods, the solvent may be an aldehyde or ketone such as acetone or diethyl ketone, or the solvent may be an ester or ether, such as ethyl acetate or dimethyl ether. The solvent may be in the form of a liquid or a supercritical carbon dioxide. In yet further exemplary methods, the solvent may be a mixture of these solvents or solvent classes. Or the separation may be performed without a solvent.
  • At step 120, the mixture is chilled to form crystals. According to some exemplary methods, the temperature to which the mixture is chilled is dependent upon the composition of the mixture, with temperatures ranging from approximately −30° C. to +15° C. In various exemplary methods, the mixture is held within this temperature range while the crystals are formed. According to further exemplary methods, the mixture may be cooled quickly or slowly to the target temperature.
  • At step 130, the mixture is filtered to separate the crystals from the liquid phase mixture. In some exemplary methods, this step needs to be performed in such a way so as to minimize the melting or dissolution of the crystals. This is usually accomplished by performing the filtration at a reduced temperature. This filtration is usually done by maintaining a negative-pressure vacuum downstream of the filter. According to various exemplary methods, the crystalline phase is rich in the saturated PA, while the liquid phase has a reduced PA concentration.
  • At step 140, the mixture may be recrystallized and re-filtered at a lower temperature to crystallize out more saturated fatty moieties, if desired. This may be repeated numerous times.
  • At step 150, if a solvent was used, according to various exemplary methods, the mixture may be heated (and optionally held under vacuum) and the solvent may be stripped from the ester mixture. This results in an O3, O6, O7 mixture with a reduced saturated moiety level.
    • Example One
  • 100 grams of dewaxed total algal ethyl esters are dissolved in ethanol to 500 mls. The mixture is chilled to −20° C. and allowed to crystallize for 6 hours. The slurry is vacuum filtered through a whatman #1 filter in a Buchner funnel chilled to −20° C. The filter cake is desolventized to yield high purity ethyl palmitate. The filtrate is stripped of ethanol under vacuum to yield an omega-7/omega-3 blend substantially reduced in ethyl palmitate.
  • FIG. 2 is a flow chart for an exemplary process for mixing a concentrated EPA O3 stream with a concentrated TAO O7 stream to produce a mixed stream.
  • At step 210, a concentrated omega-3 EPA mixture is produced from algal oil or other sources. This is described in U.S. Provisional Patent Application Ser. No. 61/800,114 filed on Mar. 15, 2013 and titled “(EPA) Algal Biomass and Oil Compositions and Impact on Health,” which is hereby incorporated by reference.
  • At step 220, a concentrated omega-7 POA mixture is produced from algal oil or other sources. This is described in U.S. Non-Provisional patent application Ser. No. ______filed on ______ concurrently with the present application and titled “Algal Omega 7 Compositions,” which is hereby incorporated by reference.
  • At step 230, the two concentrated mixtures are combined together in the desired proportion. According to some exemplary methods, the proportion of either of the mixtures may range from zero to one hundred percent.
  • At step 240, the combined mixture is mixed to produce a homogeneous mixture. In various exemplary methods, the POA and the EPA mixtures are completely miscible in each other, thus no special mixing requirements are needed. They can be shaken, stirred, agitated intensely, or agitated gently.
  • Additionally, the various algal oil compositions provided herein may further be in ethyl ester form. Such ethyl esters are derived by reacting free fatty acids with ethanol. Called -esterification, the resulting ethyl ester allows for the fractional distillation (concentration) of the long chain fatty acids at lower temperatures. This step allows for the selective concentration of the fatty acids to levels greater than found in nature.
  • The ethyl ester forms of the various exemplary algal oil compositions provided herein may be converted to a triglyceride form by performing an enzymatic reaction with the ethyl ester form in the presence of glycerol, heating under a vacuum, and filtering out the enzymes. Per some exemplary methods, immobilized lipase enzymes such as that isolated from Candida Antarctica and/or commercially available from Novozyme or Sigma Aldrich may be used.
  • While various embodiments have been described above, it should be understood that they have been presented by way of example only, and not limitation. Thus, the breadth and scope of a preferred embodiment should not be limited by any of the above-described exemplary embodiments.

Claims (28)

What is claimed is:
1. An algal fatty acid composition comprising by dry weight approximately 0.5% to approximately 99% C20:5 n3 Eicosapentaenoic acid (EPA) and approximately 0.5% to approximately 99% C16:1 n7 palmitoleic acid (POA).
2. The algal fatty acid composition of claim 1, further comprising by dry weight less than approximately 10% arachidonic acid.
3. The algal fatty acid composition of claim 1, further comprising by dry weight substantially no docosahexaenoic acid.
4. The algal fatty acid composition of claim 1, further comprising by dry weight less than approximately 20% saturated fatty acids.
5. The algal fatty acid composition of claim 1, as unsaturated from a saturated fatty acyl moiety-rich algal composition comprising by total weight approximately 50% POA, approximately 50% PA and substantially no DHA.
6. The saturated fatty acyl moiety-rich algal composition of claim 5, as processed from a total algal oil composition comprising by total weight approximately 30% EPA, approximately 27% POA, approximately 0% to 20% saturated fats, less than approximately 10% ARA, and substantially no DHA.
7. An algal fatty acid composition comprising by dry weight approximately 50% POA and approximately 25% EPA and less than approximately 20% saturated fatty acids.
8. The algal fatty acid composition of claim 7, further comprising by dry weight less than approximately 10% arachidonic acid.
9. The algal fatty acid composition of claim 7, further comprising by dry weight substantially no docosahexaenoic acid.
10. The algal fatty acid composition of claim 7, further comprising by dry weight less than approximately 20% saturated fatty acids.
11. The algal fatty acid composition of claim 7, as processed from saturated fatty acyl moiety-rich algal composition comprising by total weight approximately 50% POA, approximately 50% PA and substantially no DHA.
12. The saturated fatty acyl moiety-rich algal composition of claim 11, as processed from a total algal oil composition comprising by total weight approximately 30% EPA, approximately 27% POA, approximately 0% to 20% saturated fats, less than approximately 10% ARA, and substantially no DHA.
13. An algal fatty acid composition comprising by dry weight approximately 35% POA and approximately 35% EPA and less than approximately 20% saturated fatty acids.
14. The algal fatty acid composition of claim 13, further comprising by dry weight less than approximately 10% arachidonic acid.
15. The algal fatty acid composition of claim 13, further comprising by dry weight substantially no docosahexaenoic acid.
16. The algal fatty acid composition of claim 13, further comprising by dry weight less than approximately 20% saturated fatty acids.
17. The algal fatty acid composition of claim 13, as processed from saturated fatty acyl moiety-rich algal composition comprising by total weight approximately 50% POA, approximately 50% PA and substantially no DHA.
18. The saturated fatty acyl moiety-rich algal composition of claim 17, as processed from a total algal oil composition comprising by total weight approximately 30% EPA, approximately 27% POA approximately 0% to 20% saturated fats, less than approximately 10% ARA, and substantially no DHA.
19. An algal fatty acid composition comprising by dry weight approximately 25% POA and approximately 50% EPA, less than approximately 20% saturated fatty acids, less than approximately 10% arachidonic acid, substantially no docosahexaenoic acid, and less than approximately 20% saturated fatty acids.
20. The algal fatty acid composition of claim 1, as processed from saturated fatty acyl moiety-rich algal composition comprising by total weight approximately 50% POA, approximately 50% PA and substantially no DHA.
21. The saturated fatty acyl moiety-rich algal composition of claim 20, as processed from a total algal oil composition comprising by total weight approximately 30% EPA, approximately 27% POA, approximately 0% to 20% saturated fats, less than approximately 10% ARA, and substantially no DHA.
22. The algal fatty acid composition of claim 1, wherein the composition is in a form of an ethyl ester (EE), a mono, di- or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), Free fatty Acid (FFA), or a Sulfoquinovosyl diacylglycerol (SQDG).
23. The algal fatty acid composition of claim 7, wherein the composition is in a form of an ethyl ester (EE), a mono, di- or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), Free fatty Acid (FFA), or a Sulfoquinovosyl diacylglycerol (SQDG).
24. The algal fatty acid composition of claim 13, wherein the composition is in a form of an ethyl ester (EE), a mono, di- or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), Free fatty Acid (FFA), or a Sulfoquinovosyl diacylglycerol (SQDG).
25. The algal fatty acid composition of claim 19, wherein the composition is in a form of an ethyl ester (EE), a mono, di- or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), Free fatty Acid (FFA), or a Sulfoquinovosyl diacylglycerol (SQDG).
26. The algal fatty acid composition of claim 6, wherein the composition is in a form of an ethyl ester (EE), a mono, di- or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), Free fatty Acid (FFA), or a Sulfoquinovosyl diacylglycerol (SQDG).
27. The algal fatty acid composition of claim 12, wherein the composition is in a form of an ethyl ester (EE), a mono, di- or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), Free fatty Acid (FFA), or a Sulfoquinovosyl diacylglycerol (SQDG).
28. The algal fatty acid composition of claim 18, wherein the composition is in a form of an ethyl ester (EE), a mono, di- or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), Free fatty Acid (FFA), or a Sulfoquinovosyl diacylglycerol (SQDG).
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9445619B2 (en) 2013-03-15 2016-09-20 Aurora Algae, Inc. Compositions and methods for utilization of algal compounds
US9629820B2 (en) 2012-12-24 2017-04-25 Qualitas Health, Ltd. Eicosapentaenoic acid (EPA) formulations
US10123986B2 (en) 2012-12-24 2018-11-13 Qualitas Health, Ltd. Eicosapentaenoic acid (EPA) formulations
US10188596B2 (en) 2016-04-01 2019-01-29 Qingdao Institute Of Bioenergy And Bioprocess Technology, Chinese Academy Of Science Omega-7 fatty acid composition, methods of cultivation of tribonema for production of composition and application of composition
WO2021111452A1 (en) * 2019-12-05 2021-06-10 Vaxa Technologies Ltd. Nutritional supplement for animal and aquaculture diet and method of making same

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9101942B2 (en) 2009-06-16 2015-08-11 Aurora Algae, Inc. Clarification of suspensions
CA2892821C (en) 2012-12-06 2022-04-26 Synthetic Genomics, Inc. Algal mutants having a locked-in high light acclimated phenotype
US9266973B2 (en) 2013-03-15 2016-02-23 Aurora Algae, Inc. Systems and methods for utilizing and recovering chitosan to process biological material
US9919016B2 (en) * 2015-02-10 2018-03-20 Bilal Qizilbash Product and method of deploying kale derivatives for anti-cancer effects
US11446348B2 (en) 2017-12-30 2022-09-20 Bilal Qizilbash Vegetable powders, methods for manufacturing vegetable powders, and kits thereof
EP3890761A4 (en) * 2018-12-06 2022-11-30 James Cook University Novel composition
WO2021077027A1 (en) * 2019-10-17 2021-04-22 The Regents Of The University Of California Biologically-derived fatty acids and polymers

Family Cites Families (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1271516A (en) * 1968-08-30 1972-04-19 British Petroleum Co Method of separating carboxylic acids or esters thereof
GB8819110D0 (en) 1988-08-11 1988-09-14 Norsk Hydro As Antihypertensive drug & method for production
AU6821294A (en) * 1993-04-30 1994-11-21 Rodner R. Winget Anti-inflammatory compositions containing eicosapentaenoic acid bearing monogalactosyldiacylglycerol and methods relating thereto
AU5137901A (en) * 2000-04-06 2001-10-23 Coastside Res Method to inhibit lipoxygenase and cancer cell proliferation
JPWO2002077105A1 (en) 2001-03-22 2004-07-15 富士化学工業株式会社 Stable astaxanthin-containing powder composition and method for producing the same
US7119117B2 (en) * 2001-08-21 2006-10-10 Galileo Pharmaceuticals, Inc. Tocopherol enriched compositions and amelioration of inflammatory symptoms
CA2656311C (en) * 2006-07-05 2016-06-21 Photonz Corporation Limited Ultra pure epa and polar lipids produced in largely heterotrophic culture
CN101932714A (en) 2007-12-04 2010-12-29 俄亥俄州立大学研究基金会 Optimization of biofuel production
US20090311367A1 (en) 2008-06-17 2009-12-17 Perry Stephen C Dietary Supplement
WO2010027505A2 (en) * 2008-09-05 2010-03-11 Doron Eisenstadt Decreasing rubisco content of algae and cyanobacteria cultivated in high carbon dioxide
US8367392B2 (en) * 2008-09-05 2013-02-05 Transalgae Ltd. Genetic transformation of algal and cyanobacteria cells by microporation
US20100130608A1 (en) * 2008-10-01 2010-05-27 Martek Biosciences Corporation Compositions and methods for reducing triglyceride levels
US9187778B2 (en) * 2009-05-04 2015-11-17 Aurora Algae, Inc. Efficient light harvesting
US20110072713A1 (en) * 2009-09-30 2011-03-31 Daniel Fleischer Processing Lipids
WO2011097276A1 (en) * 2010-02-02 2011-08-11 Martek Biosciences Corporation Methods and compositions for treating arthritis with docosahexaenoic acid
CA2794854A1 (en) * 2010-04-06 2011-10-13 Heliae Development, Llc Methods of and systems for producing biofuels
US8603094B2 (en) * 2010-07-26 2013-12-10 Spinal Usa, Inc. Minimally invasive surgical tower access devices and related methods
WO2012052468A2 (en) * 2010-10-21 2012-04-26 Basf Plant Science Company Gmbh Novel fatty acid desaturases, elongases, elongation components and uses therof
WO2012109539A1 (en) 2011-02-11 2012-08-16 E. I. Du Pont De Nemours And Company An eicosapentaenoic acid concentrate
US20120213713A1 (en) * 2011-02-18 2012-08-23 Chifu Huang Compositions of omega fatty acids for the prevention and treatment of dental caries resulting from oral infections
KR20140010126A (en) 2011-03-03 2014-01-23 터서스 파마수티칼 엘엘씨 Compositions and methods comprising c16:1n7-palmitoleate
US8569530B2 (en) * 2011-04-01 2013-10-29 Aurora Algae, Inc. Conversion of saponifiable lipids into fatty esters
ES2857173T3 (en) * 2011-07-21 2021-09-28 Dsm Ip Assets Bv Microbial oils enriched in polyunsaturated fatty acids
WO2013075116A2 (en) 2011-11-17 2013-05-23 Heliae Development, Llc Omega 7 rich compositions and methods of isolating omega 7 fatty acids
US20140275613A1 (en) 2013-03-15 2014-09-18 Aurora Algae, Inc. Conversion of free fatty acids to ethyl esters

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Kitano, M., Matsukawa, R., & Karube, I. (1998). Enhanced eicosapentaenoic acid production by Navicula saprophila. Journal of applied phycology, 10(1), 101-105. *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9629820B2 (en) 2012-12-24 2017-04-25 Qualitas Health, Ltd. Eicosapentaenoic acid (EPA) formulations
US10039734B2 (en) 2012-12-24 2018-08-07 Qualitas Health, Ltd. Eicosapentaenoic acid (EPA) formulations
US10123986B2 (en) 2012-12-24 2018-11-13 Qualitas Health, Ltd. Eicosapentaenoic acid (EPA) formulations
US9445619B2 (en) 2013-03-15 2016-09-20 Aurora Algae, Inc. Compositions and methods for utilization of algal compounds
US10188596B2 (en) 2016-04-01 2019-01-29 Qingdao Institute Of Bioenergy And Bioprocess Technology, Chinese Academy Of Science Omega-7 fatty acid composition, methods of cultivation of tribonema for production of composition and application of composition
DE112016001656B4 (en) 2016-04-01 2022-06-30 Qingdao Institute Of Bioenergy And Bioprocess Technology, Chinese Academy Of Sciences Method of culturing Tribonema
WO2021111452A1 (en) * 2019-12-05 2021-06-10 Vaxa Technologies Ltd. Nutritional supplement for animal and aquaculture diet and method of making same
CN115003154A (en) * 2019-12-05 2022-09-02 瓦克萨科技有限公司 Nutritional supplement for animal and aquatic feeds and method of making same
EP4068951A4 (en) * 2019-12-05 2023-11-22 Vaxa Technologies Ltd. Nutritional supplement for animal and aquaculture diet and method of making same

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