Patent Application
20140275596
This invention relates to algal biochemistry, and more specifically, to blended algal oil compositions.
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).
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.
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.
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.
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.
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.
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.
| Number | Date | Country | |
|---|---|---|---|
| 61800114 | Mar 2013 | US | |
| 61800029 | Mar 2013 | US |
