AU2012227298A1

AU2012227298A1 - Co-precipitated salts of fatty acids

Info

Publication number: AU2012227298A1
Application number: AU2012227298A
Authority: AU
Inventors: Doug CASKEY; John Gleason; Douglas JOST; Philip H. Merrell
Original assignee: Jost Chemical Co
Current assignee: Jost Chemical Co
Priority date: 2012-09-25
Filing date: 2012-09-25
Publication date: 2014-04-10
Anticipated expiration: 2032-09-25
Also published as: AU2012227298B2

Abstract

A co-salt of a polyunsaturated fatty acid and a non-fatty acid is formed as a precipitate. The co-salt formed is free flowing and does not tend to agglomerate (cake) in storage. The resultant co-salt product will be easy to blend with other products to produce dietary supplements. These novel co-salt products may also tablet very well and may be added to current dietary supplement tablets.

Description

P/00/001 Regulation 3.2 AUSTRALIA Patents Act 1990 (Cth) COMPLETE SPECIFICATION FOR A STANDARD PATENT (ORIGINAL) TO BE COMPLETED BY APPLICANT Name of Applicant: Jost Chemical Co. Actual Inventor(s): John GLEASON Douglas JOST Philip H. MERRELL Doug CASKEY Address for Service: EKM patent & trade marks Level 1, 38-40 Garden Street South Yarra Victoria 3141 Australia Invention Title: Co-precipitated salts of fatty acids The following statement is a full description of this invention, including the best method of performing it known to us: CO-PRECIPITATED SALTS OF FATTY ACIDS [0001] This application is related to corresponding co-owned US Pat. No. 8178707 and Pub. No. US 2012/0116106. BACKGROUND [0002] The present invention relates to the preparation of co-salts of polyunsaturated fatty acids (PUFA) and another anion such as citrate, phosphate, lactate, fumarate, gluconate, carbonate, bicarbonate, malate, or other anions of common acids and the co-precipitated salts of the fatty acid and the anion; the co-salt being used as a food/feed additive or nutritional supplement. The present invention particularly relates to mixtures of monovalent and divalent metal salts rich in omega-3 and omega-6 fatty acids including eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), docosapentaenoic acid (DPA), eicosatetraenoic acid (ETA), heneicosatetraenoic acid (HPA), linoleic acid (LA), alpha linolenic acid (ALA) and arachidonic acid (ARA), in general known as omega-3 or -6 fatty acids. [0003] Several salts, such as calcium, magnesium, copper, zinc, iron, manganese, potassium, ammonium, sodium, and several others have long been recognized as beneficial mineral nutrients for humans and certain companion animals and livestock, such as dogs, cats, cattle, horses, goats, pigs, birds, fish and others. Calcium is known to be essential for the maintaining of bones and teeth. It is also responsible for a normal heartbeat and helps regulate blood pressure. The divalent cation magnesium acts as a calcium antagonist at the cell membrane level which is necessary to maintain normal electrical potentials and to coordinate muscle contraction-relaxation responses. Additionally, magnesium has roles in energy metabolism as a required cofactor for enzymes that catalyze fatty acid synthesis, protein synthesis, and glucose metabolism. Copper is utilized as an enzyme for many biochemical reactions within the biological system of birds and mammals. Copper deficiency is known to cause anemia, bone 2 disorders, neonatal ataxia, cardiovascular disorders, and many other maladies due to the inability of certain enzymes functioning properly. [0004] Zinc also is essential for protein synthesis, integrity of cell membranes, maintenance of DNA and RNA, tissue growth and repair, wound healing, taste acuity, prostaglandin production, bone mineralization, proper thyroid function, blood clotting and cognitive functions. [0005] A variety of omega-3 fatty acids have been identified as desirable for producing a diversity of nutritional and physiological benefits in humans and lower animals and accordingly have found value as nutritional supplements for a wide variety of animals. In certain animals, omega-3 fatty acids, for example, have been discovered to promote fertility, promote healthy skin and coat, reduce inflammation, and have other nutritional and physiological properties as well. In humans, it is believed that omega-3 fatty acids such as EPA and DHA support healthy cardiovascular function and are important for visual and neuronal development, support healthy blood levels of cholesterol, triglycerides and very low density lipoproteins, ease the inflammation associated with overuse of joints, and improve carbohydrate metabolism. The FDA allows the following claim to be added to products that contain omega-3: "Supportive but not conclusive research shows that consumption of EPA and DHA omega-3 fatty acids may reduce the risk of coronary heart disease." [0006] In developing fetuses and children, omega-3 fatty acids have been shown to be necessary for the eyes, brain, and developing central nervous system, In adults, omega-3 fatty acids have been shown to maintain normal cardiovascular function and maintain healthy brain and immune system function. [0007] It has also been shown that supplementing the diet of livestock with omega-3 fatty acids will alter the livestock fatty acid profile, so that, for example, feeding dairy cows and beef cattle a source of these unsaturated fatty acids will yield dairy and beef 3 products for human consumption enriched with the beneficial polyunsaturated fatty acids (PUFA). SUMMARY [0008] Generally salts of PUFA's have poor flow and processing characteristics. We have found, for example, that Ca and Mg salts of mixed anions comprised of a portion of omega fatty acids and a portion of at least one co-anion such as citrate and phosphate yield new chemical entities that are easy to handle during manufacture, and thus are easier to centrifuge, wash, and dry. Other salts of mixed cations, such as salts of Cu, Zn, Na, K, Mn Fe, Cu, NH 4 should also produce acceptable products. Other co anions include, lactic acid, fumaric acid, malic acid, gluconic acid, acetic acid, ascorbic acid, aspartic acid, carbonic acid, sulfuric acid, phosphoric acid, formic acid, propionic acid, succinic acid, adipic acid, salicyclic acid, benzoic acid, phthalic acid, maleic acid, malonic acid, pyruvic acid, sorbic acid, caprylic acid, glutaric acid, pimelic acid, glucoheptanoic acid, glycerophosphoric acid, glutamic acid, glutathione, lecithin, phenylalanine, valine, leucine, isoleucine, threonine, methionine, lysine, arginine, histidine as well as others. The polyprotic acids may be present in their respective states of protonation. The co-salt products are free flowing and do not tend to agglomerate (cake) in storage. The co-salt may be crystalline. The resultant co-salt product will be easy to blend with other products to produce dietary supplements. These novel co-salt products may also tablet very well and may be added to current dietary supplement tablets. [0009] Briefly stated, a co-salt of the claimed invention is comprised of at least a PUFA anion and at least one non-fatty acid co-anion. The co-anion is less waxy, less hydrophobic and more structurally rigid than the PUFA anion. The co-salt contains at least one cation which is ionically bonded with the PUFA anion and at least one co anion, 4 [0010] The co-salt has an infrared spectrum in which characteristic modes for the co salt are off-set from corresponding characteristic modes for an admixture of the fatty acid salt and co-anion salt of the co-salt. Thus, for example, in a calcium phosphate co salt, in which the co-salt has a calcium fatty acid salt component and a calcium phosphate component, the characteristic P-O stretching mode for the phosphate group in the co-salt is shifted relative to the characteristic P-O stretching mode for the phosphate group for an admixture of calcium fatty acid salt and calcium phosphate. Similarly, the COO' modes for the co-salt are off-set from the COO' modes for the calcium fatty acid salt. [0011] The fatty acid anion and the co-anion vary in relative concentrations from about 10% fatty acid anion and 90% co-anion to about 90% fatty acid anion and 10% co-anion; and preferably the co-salt is about 40% to about 80% fatty acid anion and about 60% to about 20% co-anion. The cation is chosen from the group consisting of calcium, magnesium, zinc, iron, manganese, copper, potassium, sodium, ammonium, and combinations thereof. [0012] The at least one co-anion is chosen from one of the groups consisting of amino acids, polyprotic inorganic acids, sugar acids, six-carbon polyprotic organic acids, alpha-hydroxy substituted acids, monoprotic short chain organic acids, aromatic acids short chain diprotic organic acids, and phosphoric acid glycerol esters. The amino acids are chosen from the group consisting of lysine, glutamic acid, methionine, aspartic acid, glutathione, phenylalanine, valine, leucine, isoleucine, threonine, arginine, and histidine. The polyprotic inorganic acid is chosen from the group consisting of phosphoric acid (monobasic, dibasic and tribasic), carbonic acid (as carbonate and bicarbonate), sulfuric acid (as both sulfate and bisulfate ions), glycerophosphoric acid, and combinations thereof. The sugar acid is chosen from the group consisting of gluconic acid, glucoheptanoic acid, and combinations thereof. The six-carbon polyprotic organic acid is chosen from the group consisting of citric acid, adipic acid, and combinations thereof. The alpha-hydroxy substituted acid is chosen from the group consisting of ascorbic acid, lactic acid, malic acid, methionine hydroxyl analog and combinations thereof. The 5 monoprotic short chain organic acid is chosen from the group consisting of acetic acid, caprylic acid, formic acid, propionic acid, pyruvic acid, sorbic acid, and combinations thereof. The aromatic acid is chosen from the group consisting of benzoic acid, salicylic acid, phthalic acids, and combinations thereof. Finally, the short chain diprotic organic acid is chosen from the group consisting of malic acid, fumaric acid, succinic acid, maleic acid, malonic acid, glutaric acid, pimelic acid, and combinations thereof. [0013] The fatty acid anion comprises at least one omega-3 or omega-6 fatty acid. The fatty acid anion is least 5% by weight omega-3 or omega-6 fatty acids; and preferably, 15% to 95% omega-3 or omega-6 fatty acids. [0014] The omega-3 fatty acid is chosen from the group consisting of alpha-linolenic acid (C18:3, n-3), eicosatetraenoic acid (C20:4, n-3), moroctic acid (C18:4, n-3), eicosapentaenoic acid (EPA) (C20:5, n-3), heneicosapentaenoic acid (C21:5, n-3), docosapentaenoic acid (C22:5, n-3), and docosahexaenoic acid (DHA) (C22:6, n-3), and combinations thereof. The omega-6 fatty acid is chosen from the group consisting of linoleic acid 18:2 (n-6), eicosatrienoic acid 20:3 (n-6), arachidonic acid 20:4 (n-6), and combinations thereof. [0015] In accordance with one aspect, the fatty acid anion comprises a complex mixture of multiple omega fatty acid anions and other fatty acid anions. This complex mixture of fatty acids can be derived from: (a) fish oils, seed oils, krill oil, or microbial oils, or (b) esters of fish oils, seed oils, krill oil, or microbial oils, or (c) triglycerides resulting from the re-esterification of purified esters from fish oils, seed oils, krill oil, microbial oils. [0016] In accordance with one aspect of the co-salt, the fish oil is 18% by weight EPA and 12% by weight DHA.

6 [0017] In accordance with one aspect of the co-salt, the ratio of the fatty acid anion to the non-fatty acid co-anion ranges from about 50:50 to 70:30, the cation for the salts is calcium or magnesium, the non-fatty acid salt is citrate or phosphate; and the omega 3 fatty acid content comprises about 15-47% of the weight of the co-salt. [0018] In accordance with one embodiment, the co-salt is produced by forming a salt solution comprised of a soluble fatty acid salt and a soluble non-fatty acid salt; adding a water solution of MX or MX 2 to the salt solution to form a reaction solution, where M is a divalent or monovalent cation, or mixtures of divalent and/or monovalent cations, and X is a water soluble anion; and then filtering the co-salt precipitate from the solution. After the precipitate has been filtered, it can be dried. It will be appreciated that the soluble fatty acid salt may, in fact, be a mixture of fatty acid salts. [0019] The MX or MX 2 is added to the salt solution in an equimolar amount of the cation to the combined molar amount of the anions of salt solution. [0020] In accordance with one aspect of the method, the salt solution is formed by combining a solution of a soluble fatty acid salt and a solution of a soluble non-fatty acid salt. In a preferred method, the soluble non-fatty acid salt solution is added to the soluble fatty acid salt in solution. In accordance with another aspect of the method, the salt solution is formed by producing an anion solution comprised of a fatty acid anion and a non-fatty acid anion; and adding a cation to the anion solution which will combine with the fatty acid and non-fatty acid to form soluble fatty acid salts and soluble non-fatty acid salts. The salt solution comprises sodium, potassium or ammonium fatty acid and non-fatty acid salts. Hence, in the second method of forming the salt solution, the cation is sodium, potassium or ammonium. [0021] In the cation solution which is added to the salt solution, M is chosen from the group consisting of Ca, Mg, Cu, Zn, Fe, Mn, K, Na, NH 4 and combinations thereof; and X is chosen from the group consisting of Cl", N0 3 , SO 4 , acetate, formate, carbonate, bicarbonate, and the like and combinations thereof.

7 BRIEF DESCRIPTION OF THE DRAWINGS (0022] FIG. 1 shows X-ray Diffraction Patterns of (1) a 50:50 Calcium Citrate Calcium/Fatty Acid Co-Salt (bottom line) prepared in accordance with the claimed invention; (2) Calcium Citrate (top line) and (3) a 50:50 admixture of Calcium Fatty Acid Salt and Calcium Citrate salt (middle line); [0023] FIG. 2 is an infrared spectra of calcium citrate tetrahydrate, a calcium salt derived from an omega-3 fish oil, and a co-precipitated calcium co-salt containing citrate anion and an omega-3 anion; [0024] FIG. 3 contains infrared spectra of calcium phosphate tribasic, a calcium salt derived from omega-3 fish oil, and a co-precipitated calcium co-salt containing phosphate and the omega-3 anion; [0025] FIG. 4 contains x-ray diffraction patterns for calcium omega-3 ascorbate co salt (top), calcium omega-3 salt (middle) and calcium ascorbate salt (bottom); (0026] FIG. 5 contains x-ray diffraction patterns for manganese omega-3 gluconate co-salt (top), manganese omega-3 salt (middle), and manganese gluconate salt (bottom); [0027] FIG. 6 contains x-ray diffraction patterns for zinc omega-3 methionate hydroxy analog co-salt (top), zinc omega-3 salt (middle), and zinc methionate hydroxy analog salt (bottom); [0028] FIG. 7 contains x-ray diffraction patterns for calcium omega-3 methionate hydroxy analog co-salt (top), calcium omega-3 salt (middle) and, calcium methionate hydroxy analog salt (bottom); 8 [0029] FIG. 8 contains x-ray diffraction patterns for magnesium omega-3 malate co salt (top), magnesium omega-3 salt (middle), and magnesium malate salt (bottom); [0030] FIG. 9 contains x-ray diffraction patterns for zinc omega-3 caprylate co-salt (top), zinc omega-3 salt (middle), and zinc caprylate salt (bottom); [0031] FIG. 10 contains x-ray diffraction patterns for magnesium omega-3 citrate co salt (top), magnesium omega-3 salt (middle), and magnesium citrate salt (bottom); [0032] FIG. 11 contains infrared spectra for calcium omega-3 ascorbate co-salt (top), calcium omega-3 salt (middle), and calcium ascorbate salt (bottom); [0033] FIG. 12 contains infrared spectra for magnesium omega-3 ascorbate co-salt (top), magnesium omega-3 salt (middle), and magnesium ascorbate salt (bottom); [0034] FIG. 13 contains infrared spectra for calcium omega-3: lysinate co-salt (top), calcium omega-3 salt (middle), and calcium lysinate salt (bottom); [0035] FIG. 14 contains infrared spectra for calcium stearate gluconate co-salt (top), calcium stearate salt (middle), and calcium gluconate salt (bottom): [0036] FIG. 15 contains infrared spectra for zinc stearate gluconate co-salt (top), zinc stearate salt (middle), zinc gluconate salt (bottom); [0037] FIG. 16 contains infrared spectra for zinc omega-3 citrate co-salt (top), zinc omega-3 salt (middle), and zinc citrate salt (bottom); [0038] FIG. 17 contains infrared spectra for zinc omega-3 gluconate co-salt (top), zinc omega-3 salt (middle), and zinc gluconate salt (bottom); 9 [0039] FIG. 18 contains infrared spectra for calcium omega-3 methionate (top), calcium omega-3 salt (middle), and calcium methionate salt (bottom); [0040] FIG. 19 contains infrared spectra for ferrous omega-3 gluconate co-salt (top), ferrous omega-3 salt (middle), and ferrous gluconate salt (bottom); [0041] FIG. 20 contains infrared spectra for cupric omega-3 gluconate co-salt (top), cupric omega-3 salt (middle), and cupric gluconate salt (bottom); [0042] FIG. 21 contains infrared spectra for zinc omega-3 acetate co-salt (top), zinc omega-3 salt (middle), and zinc acetate salt (bottom); [0043] FIG. 22 contains infrared spectra for magnesium omega-3 benzoate co-salt (top), magnesium omega-3 salt (middle), and magnesium benzoate salt (bottom); [0044] FIG. 23 contains infrared spectra for zinc omega-3 glutamate co-salt (top), zinc omega-3 salt (middle), and zinc glutamate salt (bottom); [0045] FIG. 24 contains infrared spectra for sodium omega-3 benzoate co-salt (top), sodium omega-3 salt (middle), sodium benzoate salt (bottom); and [0046] FIG. 25 contains infrared spectra for calcium omega-3 glycerophosphate co salt (top), calcium omega-3 salt (middle), and calcium glycerophosphate salt (bottom). [0047] Corresponding reference numerals will be used throughout the several figures of the drawings. DETAILED DESCRIPTION [0048] The following detailed description illustrates the invention by way of example and not by way of claimed limitation. This description will clearly enable one skilled in 10 the art to make and use the claimed invention, and describes several embodiments, adaptations, variations, alternatives and uses of the claimed invention, including what we presently believe is the best mode of carrying out the claimed invention. Additionally, it is to be understood that the claimed invention is not limited in its application to the details of construction and the arrangements of components set forth in the following description or illustrated in the drawings. The claimed invention is capable of other embodiments and of being practiced or being carried out in various ways. Also, it is to be understood that the phraseology and terminology used herein is for the purpose of description and should not be regarded as limiting. [0049) It has been found that co-precipitated anion co-salts can be produced that yield easy to handle free flowing compounds, which can then be used as additives in food or feed. These co-precipitated salts can be comprised of a cation such as Ca or Mg and a mixture of at least one fatty acid anion and at least one non-fatty acid co anion. Other cations, such as Fe, Mn, K, Cu, Zn, and Na or other divalent or monovalent metal ions may also be acceptable. The fatty acid anion for the co-salt can be a mixture of omega fatty acids obtained from commercial fish oils or seed oils or their esters or re esterified products by saponification as well as DHA/EPA enhanced fatty acids or esters that are commercially available. These fatty acids can be obtained from microbial products (algae) as well. These fatty acids can also be obtained from krill oil as well. The mixture of omega fatty acids can include alpha-linolenic acid, moroctic acid, eicosatetraenoic acid, eicosapentaenoic acid (EPA), heneicosapentaenoic acid, docosapentaenoic acid, docosahexaenoic acid (DHA), arachidonic acid (ARA), and alpha linoleic acid. The co-anion of the co-salt can be selected from any of a large number of commercial acids such as citric, lactic, phosphoric, fumaric, malic, gluconic, carbonic, sulfuric, and the like. Acetic acid, ascorbic acid and aspartic acid or any other organic or inorganic acid that will form salts with the above-noted cations can be used for the second anion. Additionally, formic acid, propionic acid, succinic acid, adipic acid, salicyclic acid, benzoic acid, phthalic acid, maleic acid, malonic acid, pyruvic acid, sorbic acid, caprylic acid, glutaric acid, pimelic acid, glucoheptanoic acid, glycerophosphoric acid, glutamic acid, glutathione, lecithin, phenylalanine, valine, 11 leucine, isoleucine, threonine, methionine, lysine, arginine, histidine could be used as well. The co-anions can be sub-grouped, as described below, into the following sub groups: (a) amino acids, (b) polyprotic inorganic acid, (c) sugar acids, (d) six carbon polyprotic organic acids, (e) alpha-hydroxy substituted acids, (f) monoprotic short chain organic acids, (g) aromatic acids (h) short chain diprotic organic acids, and (i) phosphoric acid glycerol esters. It will be understood that the polyprotic acids may be present in their respective states of protonation. The final product (i.e., the co-salt) is granular and free flowing, and can be utilized in products (i.e., food or feed) that are meant to be fortified with mineral salts and omega fatty acids. The product can be crystalline (or can exhibit some degree of crystallinity). [00503 In practice, a complex and variable mixture of omega fatty acids is expected to be used in producing the co-salt. Thus, for example, a final product of a 50:50 co precipitated calcium co-salt with citric acid and omega-3 acid anions will contain various mixtures of the individual fatty acids obtained from the original oil. For example, menhaden oil, a common fish oil, can provide the acids found in Table 1, below. Table 1: MENHADEN OIL - TYPICAL FREE FA TTY ACID PROFILE Fatty Acid Weight % in (Chain Length : Number of Double Bonds) Menhaden Oil Myristic Acid 14:0 10.86 15:0 0.67 Palmitic Acid 16:0 18.20 Palmitoleic 16:1 (n-7) 13.79 16:2 (n-4) 2.35 16:4 (n-1) 2.34 17:0 0.64 Stearic Acid 18:0 2.89 Oleic Acid 18:1 (n-9) 9.60 18:1 n-7 3.57 18:2 n-6 1.60 Linoleic Acid 18:2 (n-6) 1.60 alpha-Linolenic Acid 18:3 (n-3) 1.23 Stearidonic Acid 18:4 (n-3) 3.63 20:1 (n-9) 1.53 Eicosatrienoic Acid 20:3 (n-6) 0.19 Arachidonic Acid 20:4 (n-6) 10.89 12 20:4 (n-3) 11.43 lEicosapentaenoic Acid 20:5 (n-3) (EPA) 113.87 Docosap~entaenoic Acid 22:5 (n-3) 11.86 IDocosahexaenoic Acid 22:6 (n-3) (DHA 17.10 Reference: Yang, L.Y.; Kuksis, A.; Myher, J. J., Journal of Lipid Research, Vol.31, 1990, p.37 [0051] Each of these fatty acids will be contained in the final product as the salt of the particular fatty acid in the same mole ratio found in the original oil. The mixture of fatty acids has a fixed average molecular weight that is determined by titration. The total variety of acid anions obtained from each oil will be called, for ease, "omega-ate" when these anions are incorporated in a salt. For example, in a 50:50 co-salt of calcium citrate with the fatty acids of the above fish oil, the initial amount of DHA would be 50% of 7.1% or 3.55% based on the chart above factored down to account for the calcium and water in the final product. The co-anion would be citrate and the mixture of the above fatty acids from the fish oil would be "omega-ate". [0052] In naming these co-precipitated co-salts, the nominal ratio, (say for a 70:30 co-salt) describes the relative weights of the two salts present in the product. The first value describes the weight percent of the fatty acid salt. The second value describes the weight percent of the non-fatty acid salt. For example, a "70:30 calcium citrate co-salt" would describe a co-salt comprised of 70% by weight calcium omega-ate salt and 30% by weight calcium citrate. [0053] The Tables 2-4 below show results of calculations of theoretical total percent of calcium (or magnesium) of the co-precipitated salt using fish oil having different amounts of omega fatty acids and for varying ratios of the free fatty acid to the secondary non-free fatty acid anion. The calculations are based on a single admixture of a calcium fatty acid salt and calcium citrate-tetrahydrate. Tables 2-4 are intended to depict the range of possible product concentrations of both the mineral nutrient, either calcium or magnesium, and the omega-3 content from varying the omega-3 content of 13 the starting fish oil or from varying the ratio of the two anions. It will be understood that any co-salt produced will also include a fatty acid component as well. [0054] The cations that can be used to produce the co-salts include calcium (Ca), Magnesium (Mg), copper (Cu), zinc (Zn), Iron (Fe), manganese (Mn), potassium (K), sodium (Na), and ammonium

(NH

4 ). [0055] The co-anions can be an amino acid, a polyprotic inorganic acid, a sugar acid, a six-carbon polyprotic organic acid, an alpha-hydroxy substituted acid, a monoprotic short chain organic acid, an aromatic acid, a short chain diprotic organic acid and/or a phosphoric acid glycerol ester. e The amino acids can be lysine, glutamic acid, methionine, aspartic acid, glutathlone, phenylalanine, valine, leucine, isoleucine, threonine, arginine, and/or histidine. - The polyprotic inorganic acid can be phosphoric acid, carbonic acid, and/or sulfuric acid. * The sugar acid can be gluconic acid and/or glucoheptanoic acid. - The six-carbon polyprotic organic acid can be citric acid and/or adipic acid. - The alpha-hydroxy substituted acid can be ascorbic acid, lactic acid, methionine hydroxyl analog, and/or malic acid. - The monoprotic short chain organic acid can be acetic acid, caprylic acid, formic acid, propionic acid, pyruvic acid, and/or sorbic acid. - The aromatic acid can be benzoic acid, salicylic acid, and/or phthalic acids. e The short chain diprotic organic acid can be malate, fumaric acid, succinic acid, maleic acid, malonic acid, glutaric acid, and/or pimelic acid. e Finally, the phosphoric acid glycerol ester can be glycerophosphoric acid or lecithin. [0056] In preparing the co-salt, any of the cations can be paired with any of the co anions. Thus, the co-salt can be made using calcium as the cation and citric acid as the 14 co-anion. Alternatively, sodium (Na) can be used as the cation with ascorbic acid as the co-anion. Further, although the examples below disclose compounds which use only a single co-anion and only a single cation, it is expected that the co-salt can be formed using two or more cations and/or using two or more co-anions. Hence, for example a co-salt could be prepared using, as anions, an omega-ate, citric acid and malic acid. Similarly, a co-salt could be prepared using calcium and magnesium as cations. If a single cation (e.g., calcium) is used with the two co-anions (e.g., citric acid and malic acid), a calcium-omega-ate/malate/citrate co-salt would be produced. If only one secondary anion (e.g., citric acid) and two cations (e.g., calcium and magnesium) were used, a calcium/magnesium-omega-ate/citrate co-salt would be produced. Finally, if two secondary anions (e.g., citric acid and malic acid) and two cations (e.g., calcium and magnesium) were used, the resulting co-salt would be a calcium/magnesium omega-ate/citrate/malate co-salt. The co-salt could also be prepared using more than two cations and/or more than two secondary anions. [0057] The concentration of the omega-3 of the co-salt is fixed by the origin of the free fatty acid (FFA). For the "70:30 calcium citrate co-salt" example of Table 2, below, if the original free fatty acid contained 30% EPA+DHA, then the final product would contain 21% by weight calcium salts of EPA+DHA, and would contain 10.9% by weight calcium. As can be appreciated, the percent by weight calcium in the co-salt includes the calcium in both the fatty acid salt and the non-fatty acid salt. [0058] The ratio of the FFA anions to the non-fatty acid anion can range from about 90% FFA by weight (i.e., about a 90:10 ratio) to about 90% non-fatty acid by weight (i.e., about a 10:90 ratio). Thus, for example, in a citrate co-salt, a co-salt can be produced that contains about 90% fatty acid and about 10% of the citrate (about 90:10) while a product at the opposite end of the range can contain about 10% fatty acid and about 90% citrate (about 10:90). Table 2 summarizes an example of the range of products made from a 35% omega-3 fish oil and citrate anions with calcium as the metal ion.

15 Table 2 % 0mega-3 Salt and %Calcium Contents for Various Co-Salt Compositions Wt % Wt %Ca--3 wt% Ca- as as Total wt % Ca- o-3' Calcium Total wt% FFA EPA DHA (EPA+DHA) Citrate Calcium 10 1.8 1.2 3.0 90 19.6 30 5.4 3.6 9.0 70 16.7 45 8.1 5.4 13.5 55 14.5 50 9.0 6.0 15.0 50 13.8 60 10.8 7.2 18.0 40 12.3 65 11.7 7.8 19.5 35 11.6 70 12.6 8.4 21.0 30 10.9 90 16.2 10.8 27.0 10 8.0 *This column contains the % by weight calcium EPA+DHA. Actual EPA+DHA content, as the free acid, is calculated based on the starting average free fatty acid molecular weight. For example, a 1,000 mg tablet of a "70:30 calcium citrate co-salt" would contain 196 mg EPA+DHA, and 109 mg calcium. (0059] Table 3 shows the same 35% omega-3 fish oil product using magnesium phosphate as the co-salt. Table 3 % Omega-3 Salt and % Magnesium Contents for Various Co-Salt Compositions wt% Mg-Q-3 wt% as as Total %Mg-03 wt% Mg total Mg-FFA EPA DHA (EPA+DHA) Phosphate wt% Mg 30 5.4 3.6 9.0 70 15.7 _45 8.1 5.4 13.5 55 13.2 50 9.0 6.0 15.0 50 12.4 60 10.8 7.2 18.0 40 10.7 65 11.7 7.8 19.5 35 9.9 90 16.2 10.8 27.0 10 5.8 16 [0060] If the omega-3 percentage in the starting oil is increased to 66%, the results in Table 4 are produced for an array of calcium phosphate co-salts: Table 4 %Omega-3 Salt and %Calcium Contents for Various Co-Salt Compositions wt% Ca-fl-3___ wt% as as Total %Ca-3 wt% Ca total Ca-FFA DEPA HA (EPA-DHA) Phosphate wt% Ca 30 1 1. 30 11.7 7.8 19.5 70 29.8 45 17.6 11.7 29.3 55 24.8 50 19.5 13.0 32.5 50 23.1 60 23.4 15.6 39.0 40 19.7 65 25.4 16.9 42.3 35 181 901 35.1 23.4 58.51 10 [0061] It is clear that there is a wide variety of products that will contain different amounts of the cation and the omega-ate anions. Evidence of New Compound [0062] Figure 1 shows X-ray Diffraction Patterns of (1) a 50:50 Calcium Citrate Calcium/Fatty Acid Co-Salt (bottom line) prepared in accordance with the method described below; (2) Calcium Citrate (top line) and (3) a 50:50 admixture of Calcium Fatty Acid Salt and Calcium Citrate salt (middle line). An admixture is defined simply as a mixture in which the mixture components (calcium fatty acid salt and calcium citrate salt in this example) are dry-blended together. As seen from Figure 1, the X-ray diffraction patterns indicate that there is some crystallinity in the co-salt. The X-ray diffraction of Figure 1 makes clear that the 50:50 precipitated co-salt product is different from a 50:50 dry blend or admix of the calcium citrate and calcium fatty acid salt. [0063] Figure 2 shows the infrared spectra of calcium phosphate (top line), a calcium salt derived from fish oil (middle line), and a co-precipitated calcium salt containing phosphate ion and an omega-ate anion (bottom line). The strong band at 1026 cm 1 in 17 the spectrum of calcium phosphate is characteristic of a P-O stretching mode for an ionic phosphate group (tetrahedral symmetry). The shift to lower wave numbers (5cm") observed for the P-O stretching mode of the phosphate ion in the spectrum of the co precipitated salt demonstrates that a novel calcium omega-ate phosphate co-salt has formed. The bands of interest in the spectrum of the Ca omega-ate co-salt are the asymmetric and symmetric COO~ stretching modes centered at 1540 cm- 1 and 1434 cm, respectively, in the middle line. The shift to higher wave numbers in the spectrum of the co-precipitated co-salt also indicate a novel calcium omega-ate phosphate co-salt has been formed as opposed to a simple mixture of the two salts. [0064] Figure 3 shows the infrared spectra of calcium citrate (top line), a calcium salt derived from omega-ate fish oil fatty acids (middle line), and a co-precipitated calcium co-salt containing citrate and omega-ate anions (bottom line), hereafter called calcium citrate 50:50 co-salt. The bands of interest are the asymmetric and symmetric COO stretching vibrations centered at approximately 1550 cm- 1 and 1430 cm", respectively, in the middle line, and the wagging and scissoring modes in the region of 600 to 1310 cm which are more well defined in the spectra of calcium citrate (top line) and the co precipitated co-salt (bottom line). The change in splitting patterns and shifts in wave number of the COO- stretching vibrations observed in the spectrum of the co precipitated salt relative to the same modes in the spectra of calcium citrate or calcium omega-ate demonstrate the formation of a novel compound, as opposed to a simple mixture of the two salts. For example, the symmetric COO- stretching vibrations mode is characterized by a strong doublet observed at 1433 cm 1 and 1386 cm-' in the spectrum of calcium citrate, whereas the symmetric COO- stretching vibrations mode is characterized by a unique singlet at 1429 cm"' in the spectrum of the co-precipitated co salt. Furthermore, the wagging and scissoring modes observed in the region of 600 cm-1 to 1310 cm" remain well defined in the spectrum of the co-precipitated co-salt but are shifted to higher wave numbers, further demonstrate the formation of a novel species.

18 General Preparation and Working Examples [0065] The co-precipitated co-salt may be produced by preparing a solution of a soluble fatty acid (omega-ate) salt and a co-anion salt. The salt solution is prepared at ambient or room temperature (i.e., approximately 25-32*C). The salt of the anions can be a sodium salt. Potassium or ammonium are expected to work as well. The soluble salt solution can be prepared two ways. In a first method, a co-anion salt solution is added to a fatty acid salt solution. In a second method, the anions (i.e., the omega-ate ions and the co-anion) are combined and, for example, a sodium solution (i.e., an NaOH solution) is added to the anion solution to form the fatty acid and co-anion salts. In the first noted method, the sodium salt solution of the free fatty acid can be derived from saponifying fish oils, the ethyl or methyl esters of fish oil fatty acids or from transesterification of those oils. The same technique can be applied to seed oils, microbial oils, krill oil, and re-esterified omega-3 acid products. Possible choices for co anions include citric acid, lactic acid, phosphoric acid, fumaric acid, malic acid, gluconic acid, acetic acid, ascorbic acid, aspartic acid, carbonic acid, or sulfuric acid, formic acid, propionic acid, succinic acid, adipic acid, salicyclic acid, benzoic acid, phthalic acid, maleic acid, malonic acid, pyruvic acid, sorbic acid, caprylic acid, glutaric acid, pimelic acid, glucoheptanoic acid, glycerophosphoric acid, glutamic acid, glutathione, lecithin, phenylalanine, valine, leucine, isoleucine, threonine, methionine, lysine, arginine, histidine and the like and combinations thereof. As noted above, the polyprotic acids may be present in their respective states of protonation. [0066] After the soluble salt solution has been prepared, an exchange reaction is performed in which, with vigorous stirring, a water solution of MX or MX 2 is added (where M can be Ca, Mg, Cu, Zn, Fe, Mn, or other divalent or monovalent cations and X is a water soluble anion such as Cl', N0 3 , SO 4 , acetate, formate, and the like). The co salt immediately begins precipitating with the addition of the metal salt solution (different metal salts have slightly different solubilities). After addition of at least a stoichiometrically equivalent amount of cation to the combined molar amount of the two 19 anions, the solution is digested for an hour. It is then filtered, washed with water, and dried. The final product is a solid free flowing material. [0067] Without the second anion, it has been demonstrated that many of the metal salts of the pure fatty acids are waxy and do not filter or dry well. They also do not blend well with other products. The reaction of the second anion (i.e., the co-anion) contributes to improved handling properties of these products. Examples [0068] Table 5 below presents experimental data showing various co-salts that have been produced employing the general co-precipitation procedure described above. Specific and detailed "working examples", described later, elaborate on the concept. In addition, Table 5 provides the theoretical weight percents of the omega-3 fatty acid (i.e., combined EPA and DHA) and the theoretical weight percent of the cation (i.e., calcium or magnesium). As described above, the theoretical weight percents are calculated assuming an admixture of the omega-ate salt with calcium citrate tetrahydrate, calcium phosphate, and magnesium phosphate.

'a) Cu 0L) c o ) 0) ~ C\JLOO() CD0)C)c o )c : 6(6 C 6 CWS C6o 6 0 .2 + oo0" 0000 c0oo000 0< .cv) 0 0 -~ '~9 Nc ~CV OO CI N 4Lj) d c6 cocJ a) 066 CN-C CL 0 U) 0 0U Go W.O 00 0o 0 c X 0 1 r Y c 0 CON 0 'l £0 ___ o)EiE Dc)c oC OT M~CD a'- CD CD CD CD - C 0. <00NO0o 0 0 0 0~o 0 -D LL in o 6 - c0cN In ")U UL.OO~ 0O0OL In_ ~ .

21 [0069] The fact that the experimental data differed from the theoretical calculations, as shown in Table 5 above, is further evidence that the co-salt is a novel compound and not simply an admixture of two salts. Working Example A [0070] Preparation of 50:50 Calcium Omega-3 Salt: Calcium Citrate Tetrahydrate Co-Salt 1. Preparation of Free Fatty Acid Sodium Salt Solution: Assemble a round bottom 2-Liter three-necked flask equipped with a motor-driven Teflon paddle stirrer, a nitrogen purge inlet, a heating mantle, and a 130 mL capacity addition funnel with pressure-equalizing sidearm. Purge thoroughly with nitrogen. Then add 320 mL's degassed demonized water. Continue a slow nitrogen purge throughout the remaining steps. 2. Next, add 46.9 grams of a "free fatty acid" mixture derived from menhaden oil by saponification and having an average equivalent weight of 288 grams/mole. 3. Adjust the temperature of the stirring mixture to 30-32* C. Then add dropwise a solution of 13.0 grams 60% sodium hydroxide dissolved in 100 mL's of degassed deionized water. 4. Preparation of Trisodium Citrate Solution: In a separate 400mL glass beaker equipped with a magnetic stirbar, and using a stirrer/hot-plate, make a solution by mixing 150 mL's deionized water, 33.7 grams citric acid, and 42.0 grams 50% sodium hydroxide. Use a cooling water bath to cool the solution to 30-32 0 C. 5. Over a 10-minute period and with rapid stirring, add all of the "Trisodium Citrate solution" to the "Free Fatty Acid Sodium Salt solution". As the addition proceeds, add 200mL's more degassed deionized water to the stirring mixture. 6. When the addition of the "Trisodium Citrate solution" to the "Free Fatty Acid Sodium Salt solution" is complete, continue rapid stirring of the somewhat viscous solution. 7. Next, begin the dropwise addition of 163mL's of a 21.5% aqueous solution of calcium chloride. The addition rate is such that about one hour is required for complete addition of the 163 mL's of calcium chloride solution. Precipitation occurs 22 throughout the addition. The final resulting reaction mixture is a thick slurry of white solids. 8. Stir for an additional one hour. 9. Collect the product by vacuum filtering the slurry on a 12.5-cm Buchner Funnel, using a Fisherbrand number 6, glass fiber filter medium. Wash the product with 200 mL's degassed deionized water. 10. Dry the wet product in a vacuum oven to constant weight. The theoretical weight of dry product is 100 grams. Actual obtained dry weight is 98.5 grams. PRODUCT ANALYSIS [0071] 50:50 Calcium Omega-3 Salt: Calcium Citrate Co-Salt % Calcium = 12.6% % EPA + DHA, by GC Analysis, as fatty acid methyl esters (FAMES) = 11.5% Theoretical Expected %[EPA + DHA] = 15.0% Thermogravimetric Analysis of %Weight Loss on Heating to 120* C = 3.0% The product is a solid free flowing material. Working Example B [0072] Preparation of 50:50 Calcium High-Omega-3 Salt: Calcium Phosphate Co-Salt 1. Preparation of Free Fatty Acid Sodium Salt Solution: Assemble a round bottom 2-Liter three-necked flask equipped with a motor-driven Teflon paddle stirrer, a nitrogen purge inlet, a heating mantle, and a 130mL capacity addition funnel with pressure-equalizing sidearm. Purge thoroughly with nitrogen. Then add 320mL's degassed deionized water. Continue a slow nitrogen purge throughout the remaining steps. 2. Next, add 47.1 grams of a "free fatty acid" mixture derived by saponification from a highly refined re-esterified fish oil. The free fatty acid has an average equivalent weight of 313 grams/mole. The gas chromatographic assay of the starting re esterified oil, by fatty acid methyl ester (FAME) analysis was 94 % (EPA + DHA).

23 3. Adjust the temperature of the stirring mixture to 29-31 C. Then add dropwise a solution of 11.5 grams 50% sodium hydroxide dissolved in 100 mL's of degassed deionized water. Adjust the temperature of the solution to 30 0 C. 4. Preparation of Trisodium Phosphate Solution: In a separate 600 mL glass beaker equipped with a magnetic stirbar, and using a stirrer/hot-plate, make a solution by adding 420 mL's deionized water, followed by 34.6 grams 85% Phosphoric Acid. To the diluted phosphoric acid solution, add dropwise 72.5 grams 50% sodium hydroxide (0.906 mole). Use a cooling water bath to cool the solution to 30-32'C. 5. Over a 10-minute period and with rapid stirring, add all of the "Trisodium Phosphate solution"to the "Free Fatty Acid Sodium Salt solution". As the addition proceeds, add 300 mL's more degassed deionized water to the stirring mixture. 6. When the addition of the "Trisodium Phosphate solution"to the "Free Fatty Acid Sodium Salt solution" is complete, continue rapid stirring of the somewhat viscous solution. Adjust the temperature to 26 0 C. 7. Next, begin the dropwise addition of 260 mL's of a 21.5% aqueous solution of calcium chloride. The addition rate is such that about one hour is required for complete addition of the 260 mL's of calcium chloride solution. Precipitation of very small, white solids occurs throughout the addition. The final resulting reaction mixture is a thick slurry of white solids. 8. Stir for an additional one hour. 9. Collect the product by vacuum filtering the slurry on a 12.5 cm Buchner Funnel, using a Fisherbrand number 6, glass fiber filter medium. Wash the product with 300 mL's degassed deionized water. 10. Dry the wet product in a vacuum oven to constant weight. The theoretical weight of dry product is 100 grams. Actual obtained dry weight is 102 grams.

24 PRODUCT ANALYSIS (0073] 50:50 Calcium High-Omega-3 Salt: Calcium Phosphate Co-Salt: %Calcium = 20.8% % EPA + DHA, by GC Analysis, as fatty acid methyl esters (FAMES) = 46.3% Theoretical Expected % [EPA + DHAJ = 47.0% Thermogravimetric Analysis of %Weight Loss on Heating to 1200 C = 2.2% The product is a solid free flowing material. Working Example C [0074] Preparation of 50:50 Magnesium Omega-3 Salt: Magnesium Phosphate Co-Salt 1. Preparation of Free Fatty Acid Sodium Salt Solution: Assemble a round bottom 2-Liter three-necked flask equipped with a motor-driven Teflon paddle stirrer, a nitrogen purge inlet, a heating mantle, and a 130 mL capacity addition funnel with pressure-equalizing sidearm. Purge thoroughly with nitrogen. Then add 320 mL's degassed demonized water. Continue a slow nitrogen purge throughout the remaining steps. 2. Next, add 46.9 grams of a 'free fatty acid" mixture derived from menhaden oil by saponification and having an average equivalent weight of 288 grams/mole. 3. Adjust the temperature of the stirring mixture to 30-32*C. Then add dropwise a solution of 13.0 grams 50% sodium hydroxide dissolved in 100 mL's of degassed deionized water. 4. Preparation of Trisodium Phosphate Solution: In a separate 600 mL glass beaker equipped with a magnetic stirbar, and using a stirrer/hot-plate, make a solution by adding 420 mL's deionized water, followed by 32.6 grams 85% Phosphoric Acid. To the diluted Phosphoric Acid Solution, add dropwise 67.9 grams 50% Sodium Hydroxide .Use a cooling water bath to cool the solution to 30-32"C. 5. Over a 10-minute period and with rapid stirring, add all of the "Trisodium Phosphate solution" to the "Free Fatty Acid Sodium Salt solution". As the addition proceeds, add 200 mL's more degassed deionized water to the stirring mixture.

25 6. When the addition of the "Trisodium Phosphate solution" to the "Free Fatty Acid Sodium Salt solution" is complete, continue rapid stirring of the somewhat viscous solution. Adjust the temperature to 26 0 C. 7. Prepare an aqueous solution of magnesium chloride at a concentration of 16% by weight, on an anhydrous MgCl 2 basis. 8. Next, begin the dropwise addition of 318g of the 16% magnesium chloride solution to the stirring mixture of trisodium phosphate and free fatty acid sodium salts. The addition rate for the magnesium chloride solution is such that about one hour is required for complete addition of the 318g of solution. Precipitation of very small, white solids occurs throughout the addition. 9. Once the addition of the magnesium chloride solution is complete, stir the slurry for 1.5 hours at 25- 27*C. The final resulting reaction mixture is a thick slurry of white solids. 10. Collect the product in two separate loads on a lab-scale "lEC Clinical Centrifuge" having a stainless steel basket with a diameter of 5-inches, and using a polypropylene cloth as the filter medium. Each load is washed with 150 mL's deionized water. 11. Dry the wet product in a vacuum oven to constant weight. The theoretical weight of dry product is 100 grams. Actual obtained dry weight is 75 grams, since a portion of the product slurry was used for testing the centrifuge cloth prior to filtration. PRODUCT ANALYSIS [0075] 50:50 Magnesium Omega-3 Salt: Magnesium Phosphate Co-Salt % Magnesium = 9.7% % EPA + DHA, by GC Analysis, as fatty acid methyl esters (FAMES) = 15.3% Theoretical Expected % EPA + DHA = 15.0% Thermogravimetric Analysis of %Weight Loss on Heating to 120" C = 5.7% The product is a solid free flowing material.

26 Working Example D [0076] Preparation of 90:10 Calcium Omega-3 Salt: Calcium Citrate Tetrahydrate Co-Salt 1. Preparation of Mixed Sodium Salt Solution: Assemble a round bottom 2- Liter three-necked flask equipped with a motor-driven Teflon paddle stirrer, a nitrogen purge inlet, a heating mantle, and a 130 mL capacity addition funnel with pressure equalizing sidearm, Purge thoroughly with nitrogen. Then add 600 mL's degassed deionized water. Continue a slow nitrogen purge throughout the remaining steps. 2. Next add 6.74 grams citric acid. 3. Next, add 84.1 grams of a "free fatty acid" mixture derived from menhaden oil by saponification and having an average equivalent weight of 288 grams/mole. 4. Adjust the temperature of the stirring mixture to 30-32'C. Then add dropwise a solution of 32.0 grams 50% sodium hydroxide dissolved in 100 mL's of degassed demonized water. 5. Cool the solution to <30 0 C. 6. Exchange Reaction: Next, begin the dropwise addition of 100 mL's of a 21 % aqueous solution of calcium chloride. The addition rate is such that about 45 minutes is required for complete addition of the 100 mL's of calcium chloride solution. Precipitation occurs throughout the addition. The final resulting reaction mixture is a thick slurry of white solids. 7. Stir for an additional one hour. Then, shut off the agitator and allow to sit overnight under nitrogen blanket. 8. Collect the product by vacuum filtering the slurry on a 12.5-cm Buchner Funnel, using a Fisherbrand number 6, glass fiber filter medium. Wash the product with 200 mL's degassed deionized water. 9. The wet product was next reslurried in 400 mL's degassed deionized water. Then, it was again collected on a Buchner Funnel employing a Fisherbrand No.6 glass fiber filter. 10. Dry the wet product in a vacuum oven to constant weight. The theoretical weight of dry product is 100 grams. Actual obtained dry weight is 104 grams.

27 PRODUCT ANALYSIS [0077] 90:10 Calcium Omega-3 Salt: Calcium Citrate Co-Salt % Calcium = 7.0% % EPA + DHA, by GC Analysis, as fatty acid methyl esters (FAMES) = 24.9% Theoretical Expected %[EPA + DHA] = 27.0% Thermogravimetric Analysis of %Weight Loss on Heating to 120' C = 2.0% The product is a solid free flowing material. [0078] The working examples A-D use a fish oil that is either 30% or 94% by weight omega-3 fatty acids; they use citrate or phosphate as the co-anion, and calcium or magnesium as the mineral. There was one experiment in which co-salts did not form. In this experiment, a 50:50 calcium citrate co-salt was attempted to be made using a fish oil that was 94% omega-3 fatty acid by weight (that is, the oil had a very high concentration of omega-3 fatty acids). Calcium citrate co-salts did not form when the fatty acid starting material had an omega-3 concentration above about 50%. However, if the starting material is less than 50% omega-3 fatty acid, the calcium citrate co-salt was formed. In fact, as seen in Table 5, calcium citrate co-salts were formed with starting material having an omega-3 concentration of up to about 25%. Working Example E [0079] Preparation of 1:1 Molar Ratio Zinc Omega-3 Salt: Zinc Gluconate Co Salt 1. Assemble a 500-mL capacity round bottom three-necked flask, equipped with a motor-driven Teflon paddle stirrer, a nitrogen inlet and outlet, a thermometer, and a heating mantle. Charge 150-mL's deionized water. Stir vigorously for about 30-minutes under a slow nitrogen purge to degas the water. Maintain a nitrogen purge throughout the remaining steps. 2. Next charge to the degassed water 6.11 grams 6 -gluconolactone. Stir the lactone solution 2 hours at 45 - 62 0

C.

28 3. Cool to 35 - 40 0 C. Next add 9.88 grams of a 'free fatty acid" mixture having an average equivalent weight of about 288 grams/EW, and derived from saponification of an omega-3 fish oil. 4. Next add dropwise a total of about 5.49 grams of 50% sodium hydroxide solution to a final pH of 10.2 - 10.6. 5. Stir the mixture until the pH is stable and the reaction mixture is transparent. The temperature is kept at 35 - 40*C during this stir period. 6. Next the solution is concentrated by evaporation of most of the water solvent under vacuum and temperature conditions of about 29 inches Hg and 55 0 C. 7. The resulting concentrated equimolar mixture of sodium salts is next reacted with an aqueous solution of 4.86 grams zinc chloride dissolved in 15 mL's deionized water. Agitation for this final exchange reaction is provided by mortar and pestle, or other suitable high shear type mixing techniques. 8. The uniformly mixed product is dried in a vacuum oven at 60 - 65 0 C and vacuum of minimally 29 inches Hg to a constant weight. The dry product weighed 22.8 grams. PRODUCT ANALYSIS [0080] An FT-IR spectrum was obtained for the dry product. The FT-IR spectrum shows that characteristic vibration modes for the product are offset from those of an admixture of the substituent salts, namely the simple zinc free fatty acid salt and zinc gluconate. Hence, the FT-IR spectrum confirmed the formation of a co-salt. [0081] The formation of the Zinc Gluconate co-salt additionally confirms that the co salt can be formed with a co-anion that is significantly water soluble. [0082] Working Example B used a fatty acid starting material that was about 94% fatty acid by weight. Hence, co-salts can be formed using highly concentrated (or very pure) omega-3 fatty acid compositions.

29 [0083] Table 6 below lists co-salts produced in accordance with the method described above using different combinations of co-anions and cations. In the Table 6, compound numbers 1-4 correspond to Working Examples A-D. TABLE 6 - Co-Salts Produced No. Compound weight Fatty Cation Co-anion FIG. No/ ratio Acid graph type omega-3: co-anion 1 calcium omega-3 citrate, Ex."A" 50/50 Omega-3 Ca Citrate I - XRD calcium omega-3 phosphate, 50/50 Omega-3 Ca Phosphate 3 - FT-IR Ex. "B" 3 magnesium omega-3 50/50 Omega-3 Mg Phosphate calcium omega- citrate, Ex."D" 90/10 Omega-3 Ca Citrate 2- XRD 5 calcium omega-3 ascorbate 61/39 Omega-3 Ca Ascorbate 4- XRD 11 - FT-IR 6 magnesium omega-3 ascorbate 62/38 Omega-3 Mg scorbate 12 - FT-IR 7 calcium omega-3 lysinate 66/35 Omega-3 Ca Lysinate 13 - FT-IR 8 calcium stearate gluconate 57/43 stearate Ca Gluconate 14 - FT-IR 9 zinc stearate gluconate 57/43 stearate Zn Gluconate 15 - FT-IR 10 zinc mega-3 citrate 3/47 Omega-3 Zn Citrate 16 - FT-IR 11 zinc omega-3 gluconate 58/42 Omega-3 n Gluconate 17 - FT-IR 12 calcium omega-3 methionate 65/35 Omega-3 Ca methionate 18 - FT-R 13 manganese omega-3 gluconate 59/41 Omega-3 Mn Gluconate 5 - XRD 14 zinc omega-3 methionate 64/36 Omega-3 Zn methionate 6 -XRD hydroxy analog hydroxy analog 15 calcium omega-3 methionate 64/36 Omega-3 Ca methionate 7-XRD hydroxy analog hydroxy analog 16 ferrous omega-3 gluconate 59/41 Omega-3 Fe Gluconate 19 - FT-IR 17 cupric omega-3 gluconate 33/67 Omega-3 Cu Gluconate 20 - FT-IR 18 Zinc omega-3 acetate 78/22 Omega-3 n cetate 21 - FT-IR 19 Magnesium omega-3 malate 79/21 Omega-3 Mg Malate 8 - XRD 0 Magnesium omega-3 benzoate 69/31 Omega-3 Mg Benzoate 2 - FT-IR 2 Zinc omega-3 glutamate 75/25 Omega-3 Zn Glutamate 3 - FT-IR Zinc omega-3 caprylate 65/35 Omega-3 Zn Caprylate 9-XRD 3 Sodium omega-3 benzoate 68/32 Omega-3 Na Benzoate 24 - FT-IR 30 24 Calcium omega-3 75/25 Omega-3 Ca glycerophos 25 - FT-IR glycerophosphate phate 25 Magnesium omega-3 citrate 50/50 Omega-3 Mg citrate 10 - XRD [0084] As described below, from the FT-IR spectra and the XRD patterns of the figures, it is evident the co-salt that was formed is not merely an admixture of the two associated simple salts. This is evident from the fact that the characteristic modes of the co-salt are off-set from the off-set from corresponding characteristic modes for an admixture of the fatty acid salt and co-anion salt of the co-salt. [0085] Figure 4 contains FT-IR spectra of calcium omega-3:ascorbate co-salt (top), the simple calcium omega-ate (middle) and calcium ascorbate (bottom). The bands of greatest interest are the carboxylate bands at 1573 cm" and 1416 cm 1 , the asymmetric and symmetric stretching modes respectively. The peak positions have shifted from those found in the calcium omega-ate to higher wavenumbers for the asymmetric stretch and lower wavenumbers for the symmetric stretch. Also, the carbonyl peak of the calcium ascorbate at 1570 cm" has been shifted to the higher wavenumber at 1572 cmd along with the carboxylate peak of the omega-3 anion. These shifts indicate a novel calcium omega-3:ascorbate co-salt has been formed as opposed to a simple mixture of the two salts. [0086] Figure 12 contains FT-IR spectra of magnesium omega-3:ascorbate co-salt (top), the simple magnesium omega-ate (middle) and magnesium ascorbate (bottom). The bands of greatest interest are the carboxylate bands at 1577 cm" and 1406 cm", the asymmetric and symmetric stretching modes respectively. The peak positions have shifted from those found in the magnesium omega-ate to higher wavenumbers for the asymmetric stretch and lower wavenumbers for the symmetric stretch. Also, the carbonyl peak of the magnesium ascorbate at 1584 cm' has been shifted to the lower wavenumber at 1577 cm 1 along with the carboxylate peak of the omega-3 anion. These shifts indicate a novel magnesium omega-3:ascorbate co-salt has been formed as opposed to a simple mixture of the two salts.

31 [0087] Figure 13 contains FT-IR spectra of calcium omega-3:lysinate co-salt (top), the simple calcium omega-ate (middle) and calcium lysinate (bottom). The bands of greatest interest are the carboxylate bands at 1560 cm~ 1 and 1462 cm", the asymmetric and symmetric stretching modes respectively. The symmetric peak position has shifted from that found in the calcium omega-ate to a higher wavenumber. The carboxyl peak of the calcium lysinate at 1560 cm" has not shifted, but the N-H stretches of the lysinate have become essentially one broad peak indicating the freer rotation of the amine group. These shifts indicate a novel calcium omega-3:lysinate co-salt has been formed as opposed to a simple mixture of the two salts. [0088] Figure 14 contains FT-IR spectra of calcium stearate:gluconate co-salt (top), the simple calcium stearate (middle) and calcium gluconate (bottom). The bands of greatest interest are the carboxylate bands at 1554 cm- 1 and 1469, 1436, and 1419 cm , the asymmetric and symmetric stretching modes respectively. The asymmetric peaks positions have shifted from those found in the calcium stearate from two peaks at 1574 and 1538 cm', which is common for some calcium carboxylate salts, to one peak at 1554 cm 1 in the co-salt spectrum. Also, the carboxyl peak of the calcium gluconate at 1609 cm-1 has shifted to the lower wavenumber at 1554 cm" along with the carboxylate peak of the stearate anion. These shifts indicate a novel calcium strearate:gluconate co-salt has been formed as opposed to a simple mixture of the two salts. [0089] Figure 15 contains FT-IR spectra of zinc stearate:gluconate co-salt (top), the simple zinc stearate (middle) and zinc gluconate (bottom). The bands of greatest interest are the carboxylate bands at 1555 cm' and 1468 cm", the asymmetric and symmetric stretching modes respectively. The peaks positions have shifted from those found in the zinc stearate at 1535 and 1455 cm" to higher wavenumbers in the co-salt spectrum. Also, the carboxyl peak of the zinc gluconate at 1593 cm 1 has shifted to the higher wavenumber at 1594 cm". These shifts indicate a novel zinc strearate:gluconate co-salt has been formed as opposed to a simple mixture of the two salts.

32 [0090] Figure 16 contains FT-IR spectra of zinc omega-3:citrate co-salt (top), the simple zinc omega-ate (middle) and zinc citrate (bottom). The bands of greatest interest are the carboxylate bands at 1544 cm" and 1390 cm- 1 , the asymmetric and symmetric stretching modes respectively. The peaks positions have shifted from those found in the zinc omega-ate at 1536 and 1437 cm" to higher wavenumbers in the co salt spectrum. Also, the asymmetrical carboxyl peak of the zinc citrate at 1548 cm" has shifted to the lower wavenumber at 1544 cm" along with the carboxyl peak of the omega-3 anion and the symmetrical stretches have shifted to lower wavenumbers as well, from 1394 cm- 1 to 1390cm- 1 . These shifts indicate a novel zinc omega-3:citrate co salt has been formed as opposed to a simple mixture of the two salts. [0091] Figure 17 contains FT-IR spectra of zinc omega-3:gluconate co-salt (top), the simple zinc omega-ate (middle) and zinc gluconate (bottom). The bands of greatest interest are the carboxylate bands between 1590 - 1529 cm' and 1398 - 1453 cm", the asymmetric and symmetric stretching modes respectively. The peaks positions have shifted from those found in the zinc omega-ate at 1536 and 1436 cm- 1 to higher wavenumbers in the co-salt spectrum at 1547cm 1 and 1453 cm 1 . Also, the carboxyl peaks of the zinc gluconate at 1593 cm- and 1390 cm- has shifted to a lower wavenumber at 1590 cm" and a higher wavenumber 1398 cm". These shifts indicate a novel zinc omega-3:giuconate co-salt has been formed as opposed to a simple mixture of the two salts. [0092] Figure 18 contains FT-IR spectra of calcium omega-3:methionate co-salt (top), the simple calcium omega-ate (middle) and calcium methionate (bottom). The bands of greatest interest are the carboxylate bands at 1541 cm" and 1417 cm^, the asymmetric and symmetric stretching modes respectively. The asymmetric peak position has shifted from that found in the calcium omega-ate at 1537 cm- 1 to 1541 cm" in the co-salt spectrum and the symmetric stretch at 1420 cm- 1 has shifted to the lower wavenumber peak position at 1417 cm". Also, the carboxyl peak of the calcium methionate at 1560 cm" has shifted to the lower wavenumber at 1541 cm" along with 33 the carboxylate peak of the omega-3 anion. These shifts indicate a novel calcium omega-3:methionate co-salt has been formed as opposed to a simple mixture of the two salts. [0093] Figure 19 contains FT-IR spectra of ferrous omega-3:gluconate co-salt (top), the simple ferrous omega-ate (middle) and ferrous gluconate (bottom). The bands of greatest interest are the carboxylate bands at 1577 cm" and 1443 cm", the asymmetric and symmetric stretching modes respectively. The asymmetric peak position have shifted from that found in the ferrous omega-ate at 1559 cm 1 to 1577 cm 1 in the co-salt spectrum and the symmetric stretch at 1443 cm" did not shift in the co-salt spectrum. Also, the carboxyl peak of the ferrous gluconate at 1595 cm- 1 has shifted to the lower wavenumber at 1577 cm" along with the carboxylate peak of the omega-3 anion. These shifts indicate a novel ferrous omega-3:gluconate co-salt has been formed and not a simple mixture of the two salts. [0094] Figure 20 contains FT-IR spectra of cupric omega-3:gluconate co-salt (top), the simple cupric omega-ate (middle) and cupric gluconate (bottom). Again the bands of greatest interest are the carboxylate bands at 1560 cm 1 and 1443 cm" as well as 1397 cm- 1 the asymmetric and symmetric stretching modes respectively. The asymmetric peak position has shifted from that found in the cupric omega-ate at 1583 cm" to a lower wavenumber at 1560 cm 1 in the co-salt spectrum and the symmetric stretch at 1419 cm" shifted to a higher wavenumber at 1443 cm 1 co-salt spectrum. Also, the asymmetric carboxyl stretch of the cupric gluconate is split at 1649 and 1613 cm 1 has merged into a broader peak and shifted to the lower wavenumber at 1560 cm-1 along with the carboxylate peak of the omega-3 anion. The symmetric stretch for the cupric gluconate at 1392 cm- 1 has shifted to a higher position at 1397 cm 1 in the spectrum of the co-salt These shifts indicate a novel cupric omega-3:gluconate co-salt has been formed as opposed to a simple mixture of the two salts. [0095] Figure 21 contains FT-IR spectra of zinc omega-3:acetate co-salt (top), the simple zinc omega-ate (middle) and zinc acetate (bottom). The bands of greatest 34 interest are the carboxylate bands at 1548-1528 cm- 1 and 1452-1400 cm 1 , the asymmetric and symmetric stretching modes respectively. The peaks positions have shifted from those found in the zinc omega-ate at 1536 cm" to lower wavenumbers for the asymmetric stretch (1528 cm- 1 ) in the co-salt spectrum. Also, the asymmetrical carboxyl peak of the zinc acetate at 1545 cm" has shifted to the higher wavenumber at 1548 cm-1 separate from the carboxyl peak of the omega-3 anion and the symmetrical stretch has shifted from 1437 cm- 1 to either 1452 cm" or to 1400 cm 1 . These shifts indicate a novel zinc omega-3:acetate co-salt has been formed as opposed to a simple mixture of the two salts. [0096] Figure 22 contains FT-IR spectra of magnesium omega-3:benzoate co-salt (top), the simple magnesium omega-ate (middle) and magnesium benzoate (bottom). The bands of greatest interest are the carboxylate bands at 1553 cm' and 1411 cm 1 , the asymmetric and symmetric stretching modes respectively. The peaks positions have shifted from those found in the magnesium omega-ate at 1558 cm 1 to lower wavenumbers for the asymmetric stretch (1552 cm") in the co-salt spectrum and the symmetric stretch have shifted from 1429 cm 1 to 1411 cm 1 . Also, the asymmetrical carboxyl peak of the magnesium benzoate at 1555 cm" has shifted to the lower wavenumber at 1552 cm- along with the carboxyl peak of the omega-3 anion and the symmetrical stretch has merged with the symmetric stretch of the other anion at 1411 cm-1. These shifts indicate a novel magnesium omega-3:benzoate co-salt has been formed as opposed to a simple mixture of the two salts. [0097] Figure 23 contains FT-IR spectra of zinc omega-3:glutamate co-salt (top), the simple zinc omega-ate (middle) and zinc glutamate (bottom). Again the bands of greatest interest are the carboxylate bands between 1547 cm 1 and 1452 - 1400 cm", the asymmetric and symmetric stretching modes respectively. The peaks positions have shifted from those found in the zinc omega-ate at 1536 and 1436 cm 1 to higher wavenumbers in the co-salt spectrum at 1547 cm" and 1452 cm 1 . Also, the carboxyl peaks of the zinc glutamate at 1557 cm- and 1406 cm' has shifted to a lower 35 wavenumbers at 1547 cm 1 and 1400 cm- 1 . These shifts indicate a novel zinc omega-3: glutamate co-salt has been formed as opposed to a simple mixture of the two salts. [0098] Figure 24 contains FT-IR spectra of sodium omega-3:benzoate co-salt (top), the simple sodium omega-ate (middle) and sodium benzoate (bottom). The bands of greatest interest are the carboxylate bands at 1550 cm" and 1395 cm- 1 , the asymmetric and symmetric stretching modes respectively. The peaks positions have shifted from those found in the sodium omega-ate at 1558 cm" to lower wavenumbers for the asymmetric stretch (1550 cm") in the co-salt spectrum and the symmetric stretch have shifted from 1419 cm" to 1394 cm~1. Also, the asymmetrical carboxyl peak of the sodium benzoate at 1547 cm-1 has shifted to the higher wavenumber at 1550 cm 1 along with the carboxyl peak of the omega-3 anion and the symmetrical stretch has shifted lower and merged with the symmetric stretch of the omega-3 anion at 1394 cm"'. These shifts show a novel sodium omega-3:benzoate co-salt has been formed as opposed to a simple mixture of the two salts. [0099] Figure 25 contains FT-IR spectra of calcium omega-3:glycerophosphate co salt (top), the simple calcium omega-ate (middle) and calcium glycerophosphate (bottom). The bands of interest are the carboxylate bands at 1558 cm-1 and 1444 cm", the asymmetric and symmetric stretching modes respectively, well as the phosphate peaks at 1105 and 998 cm-1. The asymmetric peaks positions have shifted from those found in the calcium omega-ate from 1537 cm- 1 to a peak at 1558 cm 1 in the co-salt spectrum, and the symmetric stretch at 1419 cm" shifts higher to 1444 cm". Also, the phosphate peaks of the calcium glycerophosphate at 1126, 1085, and 1007 cm"' become two peaks in the co-salt spectrum at 11105 and 998 cm". These shifts indicate a novel calcium omega-3:glycerophosphate co-salt has been formed as opposed to a simple mixture of the two salts. [00100] Figure 4 shows the X-ray diffraction (XRD) powder patterns for calcium omega-3:ascorbate co-salt along with the simple salts of calcium omega-ate and calcium ascorbate. From these powder patterns the clear difference in the co-salt 36 powder pattern and the two other salts is clear. Likewise differences were found between the x-ray powder patterns of the co-salts of manganese omega-3:gluconate (Figure 5), zinc omega-3:methionate hydroxyl analog (Figure 6), calcium omega 3:methionate hydroxyl analog (Figure 7), magnesium omega-3:maiate (Figure 8), zinc omega-3:caprylate (Figure 9), magnesium omega-3:citrate (Figure 10) and the corresponding salts of the individual anions, thus showing that novel compounds have been produced for each of these co-salts. It is noted that NaCl peaks are also present in many of the x-ray powder patterns. [00101] Table 7 below is a two-axis table showing, along the vertical axis, the various co-anions that can be used, and along the horizontal axis, the various cations that can be used in the production of the co-salt. The numbers in the various cells correspond to the compounds listed above in Table 6, and give a visual image of the spectrum of co-salts that have been produced. The letters under the "Co-anion subgroup" column refer to the various subgroups of co-anions as noted above, as follows: (a) amino acids, (b) polyprotic inorganic acids, (c) sugar acids, (d) six-carbon polyprotic organic acids, (e) alpha-hydroxy substituted acids, (f) monoprotic short chain organic acids, (g) aromatic acids, (h) short chain diprotic organic acids, and (i) phosphoric acid glycerol esters. As can be seen from the table below, co-salts have been produced from each of the nine subgroups of co-anions. Although actual co-salts have not been produced using all the co-anions in each of the subgroups, the similarities of the compounds in the various subgroups would lead one of skill in the art to expect to be able to produce co-salts using all the co-anions and cations. For example, the amino acids lysine, glutamic acid and methionine readily form co-salts. Thus, it would be expected that the remaining listed amino acids would also produce co salts.

37 Table 7 Co-anion - Cation table Co-anion Ca Mg Cu Zn Fe Mn K Na NH 4 -_-_-_--_-sug-o up----_-_- - . 2 acetic acid f 18 arginine a ascorbic acid e 5 6 as artic acid a benzoic acid 2 0 __ -- 23 caprlic acid f _ ____22 carbonic acid b__I -__I citric acid d_11.4_25_1 formic acid fumanmmmmcmmm acid h numo anocacidrmmamme m 2Frm ed wci th m ete h21 Jlutathione a-4 glycerophasphoric acid i 2 histidine a isoleucine a lactic acid e-

-

_ lecithin ethiine a rosinic acid ruveic acid sai lic acid h soic acid h succiyni e a psulfuric acid b 2 3 vhali a Formecacd wihhert prormeacd wihmtinnf hdoyaao 38 [00102] Tables 6 and 7 also demonstrate that different but related cations also react to form co-salts. Calcium, magnesium, sodium, iron, copper, zinc and manganese show that formation of co-salts occurs with cations that represent the chemical subdivisions of metals and transition metals with equal facility. In view of the formation of co-salts with these metals and transition-metals, one would expect the same ease of co-salt formation ought to be found with potassium and ammonium. The ammonium ion while not an alkali, alkaline earth, or transition metal is a compact polyatomic cation with a localized ionic charge capable of interacting with the polyunsaturated fatty acids and the co-anion in the same mode as the metal cations. Thus, one of ordinary skill in the art would also expect ammonium to form a co-salt. [00103] In accordance with the various aspects of the method, the method for producing a co-salt of a fatty acid anion and a non-fatty acid co-anion comprises (a) forming a salt solution comprised of a soluble fatty acid salt and a soluble non-fatty acid salt; and (b) adding a water solution of MX or MX2 to the salt solution to form a reaction solution, where M is a divalent or monovalent cation, or mixtures of divalent and/or monovalent cations, and X is a water soluble anion; and filtering the co-salt precipitate from the solution. [00104] In accordance with one aspect of the method, the step of forming the salt solution comprises combining a solution of a soluble fatty acid salt and a solution of a soluble non-fatty acid salt. The step of forming the salt solution can additionally comprise adding the soluble non-fatty acid salt solution to the soluble fatty acid salt solution. [00105] In accordance with another aspect of the method, the step of forming the salt solution comprises forming an anion solution comprised of a fatty acid and a non fatty acid; and adding a cation to the anion solution which will combine with the fatty acid and non-fatty acid to form soluble fatty acid salts and soluble non-fatty acid salts.

39 [00106] The salt solution comprises sodium, potassium or ammonium fatty acid and non-fatty acid salts. [00107] M is chosen from the group consisting of Ca, Mg, Cu, Zn, Fe, Mn, K, Na, NH4, and combinations thereof; and X is chosen from the group consisting of C1, NOj, S04-2, acetate, formate, and combinations thereof. [00108] The method can further comprise steps of washing and drying the co-salt precipitate after it has been filtered from the solution. [00109] The step of adding MX or MX 2 to the salt solution comprises adding at least a stoichiometrically equivalent amount of the cation to the combined stoichiometrically equivalent amounts of the anions of salt solution. [00110] The method can further comprise a step of stirring the reaction solution for a predetermined period of time prior to filtering. [00111] As various changes could be made in the above constructions without departing from the scope of the claimed invention, it is intended that all matter contained in the above description or shown in the accompanying drawings shall be interpreted as illustrative and not in a limiting sense. For example, although the working examples use a fish oil that 35% or 65% omega-3 fatty acids by weight, the starting oil could have an omega-3 content as low as 5% by weight and as high as 100% by weight (i.e., pure omega-3 fatty acid). This example is merely illustrative.

Claims

1. A co-salt comprised of at least one polyunsaturated fatty acid anion and at least one co-anion; said co-anion being an anion which is not a fatty acid anion and that is less waxy, less hydrophobic and more structurally rigid than said at least one polyunsaturated fatty acid anion; said co-salt further comprising at least one cation which is ionically bonded with said at least one polyunsaturated fatty acid anion and said at least one co-anion to define a fatty acid salt component of the co-salt and a co-anion salt component of the co-salt; wherein the at least one polyunsaturated fatty acid anion comprises at least one omega-3 fatty acid and/or at least one omega-6 fatty acid; said at least one co-anion is chosen from the group consisting of amino acids, polyprotic inorganic acids, sugar acids, six-carbon polyprotic organic acids, alpha-hydroxy substituted acids, monoprotic short chain organic acids, aromatic acids, short chain diprotic organic acids, phosphoric acid glycerol esters, and combinations thereof; said at least one cation being chosen from the group consisting of calcium, magnesium, zinc, iron, manganese, copper, potassium, sodium, ammonium, and combinations thereof; and the weight ratio of the fatty acid anion to the non-fatty acid co-anion in the co-salt ranges from about 90:10 to about 10:90.

2. The co-salt of claim 1 wherein: a. said amino acid is chosen from the group consisting of lysine, glutamic acid, methionine, aspartic acid, glutathione, phenylalanine, valine, leucine, isoleucine, threonine, arginine, histidine, and combinations thereof; b. said polyprotic inorganic acid is chosen from the group consisting of phosphoric acid, carbonic acid, sulfuric acid, and combinations thereof; c. said sugar acid is chosen from the group consisting of gluconate, glucoheptanoic acid, and combinations thereof; 41 d. said six-carbon polyprotic organic acid is chosen from the group consisting of citric acid, adipic acid and combinations thereof; e. said alpha-hydroxy substituted acid is chosen from the group consisting of ascorbic acid, lactic acid, methionine hydroxyl analog, and malic acid and combinations thereof; f. said monoprotic short chain organic acid is chosen from the group consisting of acetic acid, caprylic acid, formic acid, propionic acid, pyruvic acid, sorbic acid and combinations thereof; g. said aromatic acid is chosen from the group consisting of benzoic acid, salicylic, phthalic acids, and combinations thereof; h. said short chain diprotic organic acid is chosen from the group consisting of malic acid, fumaric acid, succinic acid, maleic acid, malonic acid, glutaric acid, lactic acid, pimelic acid and combinations thereof; and i. said phosphoric acid glycerol esters being chosen from the group consisting of glycerophosphoric acid and lecithin, and combinations thereof.

3. The co-salt of claim I wherein the co-salt has at least one of an infrared spectrum and an x-ray diffraction pattern in which characteristic modes for the co-salt are off-set from corresponding characteristic modes for an admixture of the fatty acid salt and co-anion salt of the co-salt.

4. The co-salt of claim 1 wherein the at least one cation for the co-salt is chosen from the group consisting of calcium, magnesium, zinc, iron and combinations thereof.

5. The co-salt of claim 1 wherein the co-anion is chosen from the group consisting of citric acid, lactic acid, phosphoric acid, fumaric acid, sulfuric acid, and combinations thereof. 42

6. The co-salt of claim 1 wherein said fatty acid anion is at least 5% by weight omega-3 or omega-6 fatty acids.

7. The co-salt of claim 5 wherein the omega-3 fatty acid content of the fatty acid anion varies from 15% to 95% by weight.

8. The co-salt of claim 1 wherein said at least one omega-3 fatty acid is chosen from the group consisting of alpha-linolenic acid (C1 8:3, n-3), eicosatetraenoic acid (C20:4, n-3), moroctic acid (C18:4, n-3), eicosapentaenoic acid (EPA) (C20:5, n-3), heneicosapentaenoic acid (C21:5, n-3), docosapentaenoic acid (C22:5, n-3), and docosahexaenoic acid (DHA) (C22:6, n-3), and combinations thereof; and wherein the omega-6 fatty acid is chosen from the group consisting of linoleic acid 18:2 (n-6), eicosatrienoic acid (C20:3, n-6), arachidonic acid 20:4 (n-6), and combinations thereof.

9. The co-salt of claim I wherein the fatty acid anion comprises a complex mixture of multiple omega fatty acid anions and non-omega fatty acid anions.

10. The co-salt of claim 9 wherein said complex mixture of fatty acids is derived from: (a) fish oils, seed oils, krill oil, or microbial oils, or (b) esters of fish oils, seed oils, krill oil, or microbial oils, or (c) triglycerides resulting from the re-esterification of purified esters from fish oils, seed oils, krill oil, microbial oils.

11. The co-salt of claim I wherein the composition is about 40% by weight to about 80% by weight fatty acid anion and about 60% by weight to about 20% by weight co-anion.

12. The co-salt of claim 1 wherein the co-anion is carbonic acid. 43

13. A co-salt comprised of a fatty acid salt component and a non-fatty acid salt component; the co-salt being granular and free flowing; the co-salt having at least one of an infrared spectra and an X-ray diffraction pattern in which characteristic modes for the co-salt are off-set from corresponding characteristic modes for an admixture of the fatty acid salt and co-anion salt of the co-salt; wherein the fatty acid comprises at least one omega-3 fatty acid and/or at least one omega 6 fatty acid; and said at least one co-anion is chosen from the group consisting of amino acids, polyprotic inorganic acids, sugar acids, six carbon polyprotic organic acids, alpha-hydroxy substituted acids, monoprotic short chain organic acids, aromatic acids, short chain diprotic organic acids, phosphoric acid glycerol esters, and combinations thereof.

14. The co-salt of claim 13 wherein the weight ratio of the fatty acid anion to the non-fatty acid co-anion in the co-salt ranges from about 90:10 to about 10:90.

15. The co-salt of claim 13 wherein the fatty acid has an omega-3 fatty acid content of up to 95% by weight.

16. The co-salt of claim 13 wherein the omega-3 fatty acid is selected from the group consisting of alpha-linolenic acid, moroctic acid, eicosatetraenoic acid, eicosapentaenoic acid (EPA), heneicosapentaenoic acid, docosapentaenoic acid, docosahexaenoic acid (DHA), and combinations thereof.

17. The co-salt of claim 13 wherein the co-anion is selected from the group consisting of citric acid, lactic acid, phosphoric acid, fumaric acid, malic acid, gluconic acid, acetic acid, ascorbic acid, aspartic acid, sulfuric acid, formic acid, propionic acid, succinic acid, adipic acid, salicyclic acid, benzoic acid, phthalic acid, maleic acid, malonic acid, pyruvic acid, sorbic acid, caprylic acid, glutaric acid, pimelic acid, glucoheptanoic acid, glycerophosphoric acid, glutamic acid, glutathione, lecithin, phenylalanine, valine, leucine, isoleucine, threonine, methionine, lysine, arginine, histidine, and combinations thereof. 44

18. The co-salt of claim 13 wherein the salts contain a cation, the cation for the salts being selected from the group consisting of Ca, Mg, Cu, Zn, Fe, Mn, K, Na, NH 4 and combinations thereof.

19. The co-salt of Claim 13 in which the weight ratio of the fatty acid anion to the non-fatty acid co-anion ranges from about 60:50 to 70:30, and wherein the cation for the salts is calcium or magnesium, the omega-3 fatty acid content comprises about 15 47% of the weight of the co-salt, and the non-fatty acid salt is citrate or phosphate.

20. The co-salt of Claim 19 in which the fatty acid component is derived from fish oil.

21. The co-salt of Claim 20 wherein the fatty acid is 18% by weight EPA and 12% by weight DHA.

22. The co-salt of claim 13 wherein the co-anion is carbonic acid.

23. A co-salt comprised of at least one polyunsaturated fatty acid anion and one co-anion; said co-anion being an anion which is not a fatty acid anion and that is less waxy, less hydrophobic and more structurally rigid than said at least one polyunsaturated fatty acid anion; said co-salt further comprising one cation which is ionically bonded with said at least one polyunsaturated fatty acid anion and said one co-anion to define a fatty acid salt component of the co-salt and a co-anion salt component of the co-salt; wherein the at least one polyunsaturated fatty acid anion comprises at least one omega-3 fatty acid and/or at least one omega-6 fatty acid; said one co-anion is chosen from the group consisting of amino acids, polyprotic inorganic acids, sugar acids, six carbon polyprotic organic acids, alpha-hydroxy substituted acids, monoprotic short chain organic acids, aromatic acids, short chain diprotic organic acids, and phosphoric acid glycerol esters; 45 said one cation being chosen from the group consisting of calcium, magnesium, zinc, iron, manganese, copper, potassium, sodium, and ammonium; and the weight ratio of the fatty acid anion to the non-fatty acid co-anion in the co-salt ranges from about 90:10 to about 10:90.