WO2009105620A1 - Huiles mono-insaturées à chaîne courte sélectives - Google Patents

Huiles mono-insaturées à chaîne courte sélectives Download PDF

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Publication number
WO2009105620A1
WO2009105620A1 PCT/US2009/034649 US2009034649W WO2009105620A1 WO 2009105620 A1 WO2009105620 A1 WO 2009105620A1 US 2009034649 W US2009034649 W US 2009034649W WO 2009105620 A1 WO2009105620 A1 WO 2009105620A1
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Prior art keywords
oil
sscmo
vol
fatty acid
cooking
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PCT/US2009/034649
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English (en)
Inventor
John M. Burke
Bruce V. Mavec
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Cco Technology, Ltd.
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Publication of WO2009105620A1 publication Critical patent/WO2009105620A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0085—Substances of natural origin of unknown constitution, f.i. plant extracts
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12—Fatty acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/10—General methods of cooking foods, e.g. by roasting or frying
    • A23L5/11—General methods of cooking foods, e.g. by roasting or frying using oil

Definitions

  • the present invention relates to a cooking oil such as corn oil, olive oil, canola, sunflower oil, etc., having blended therein typically lesser amounts of a selective short-chain monounsaturated oil comprising a fatty acid, or a fatty alcohol derivative thereof, or a di or triglyceride containing ester side chains of said monounsaturated fatty acid.
  • a selective short-chain monounsaturated oil comprising a fatty acid, or a fatty alcohol derivative thereof, or a di or triglyceride containing ester side chains of said monounsaturated fatty acid.
  • These blends have improved properties such as extended cooking life, extended high heat stability, and extended taste life. It has also been found that food selectively absorbs the selective short chain monounsaturated oil.
  • oils utilized in the food industry for cooking and baking inherently contained saturated fats, monounsaturated fats, as well as polyunsaturated fats, and also trans (hydrogenated) fats. It is generally believed by the health and medical professions that trans fats and saturated fats are unhealthy to humans and can lead to a host of medical problems including arteriosclerosis and heart attacks. Recently, oils have been produced that do not contain trans fats. However, the need still exists to reduce the amounts of saturated fats and polyunsaturated fats in oils and to extend the cooking life, stability, and taste of cooking oils as well as to improve the taste and texture thereof.
  • Unsaturated fatty acids have a vinylic or carbon-carbon double bond at one or more positions along the acyl hydrocarbon chain.
  • the structure of the fatty acids will be characterized by notations such as Cx:yn-a.
  • Cx indicates that the fatty acyl group contains x carbon atoms; y indicates die number of carbon-carbon double bonds in the acyl chain; and n-a indicates that the most distal double bond terminates on the "a" the carbon counting from the terminal methyl end.
  • the naturally occurring fatty acids are almost exclusively in the cis configuration, and all further references to unsaturated fatty acids will indicate the cis isomer unless explicitly stated otherwise.
  • PUFA polyunsaturated fatty acid
  • the most widely occurring dietary PTJFA is linoleic acid (C18:2n-6, or 9,12-octadecadienoic acid), which constitutes more than half of the fatty acid triglycerides of corn, soy, and safflower vegetable oils.
  • the cholesterol lowering ability of PUFAs is believed to result from increased LDL receptor activity. See, Spady & Dietschy, 82 Proc. Nat. Acad. Sci. USA 4576 (1985).
  • PUFAs have significant deleterious health consequences as well as beneficial ones.
  • Several negative effects of PUFAs may be ascribed to their increased rate of reaction via free-radical mechanisms. See, e.g,, B. Halliwell and J. Gutteridge, "Lipid Peroxidation,” Ch. 4 in Free Radicals in Biology and Medicine, (2d ed. 1989).
  • PUFAs usually have two vinylic groups separated by a methylene carbon, as is exemplified by the 9,12 diene structure of linoleic acid.
  • the bridging methylene carbon e.g., CIl of linoleic acid
  • free-radical substitution reactions by both of the adjacent vinylic groups.
  • PUFAs lower the level of beneficial HDL cholesterol as well as the level of harmful LDL cholesterol. Since high HDL levels protect against atherosclerosis, the HDL-lowering effect of PUFAs could make them more rather than less atherogenic than saturated fatty acids.
  • PUFAs monounsaturated fatty acids
  • oleic acid C18:ln-9
  • Oleic acid is a major component of olive oil
  • some epidemiological evidence suggests that Mediterranean populations with high olive oil consumption have a reduced incidence of atherosclerosis and associated heart disease.
  • oleic acid caused no reduction in HDL cholesterol levels. Based on this reported HDL sparing property of oleic acid, some researchers have urged that oleic acid should become a major source of dietary fat, whereas linoleic acid should be restricted to modest intakes. See, S. M. Grundy, "Monounsaturated Fatty Acids and Cholesterol Metabolism: Implications for Dietary Recommendations," 119 J. Nutrition 529-533 (1989).
  • Medicinal properties also have been asserted for a particular type of C16: 1 MUFA.
  • Iwamura, et al. in U.S. Pat. No. 4,239,756 have disclosed the use of a compound which is a positional and geometric isomer of palmitoleic acid in a method for treating diabetes or improving lipid metabolism.
  • the fatty acids disclosed are therefore C14:ln-12, C16:ln-14, C18:l ⁇ -16, and C20:ln-18.
  • A. Hydrolysis of Fats [00121 Like other esters, glycerides can be hydrolyzed readily. Partial hydrolysis of triglycerides will yield mono- and diglycerides and fatty acids. When the hydrolysis is carried to completion with water in the presence of an acid catalyst, the mono-, di-, and triglycerides will hydrolyze to yield glycerol and fatty acids. With aqueous sodium hydroxide, glycerol and the sodium salts of the component fatty acids (soaps) are obtained, m the digestive tracts of humans and animals and in bacteria, fats are hydrolyzed by enzymes (lipases). Lypolytic enzymes are present in some edible oil sources (i.e., palm fruit, coconut). Any residues of these lipolytic enzymes present in some crude fats and oils are deactivated by the temperatures used in oil processing, so enzymatic hydrolysis is unlikely in refined fats and oils.
  • Autoxidation Of particular interest in the food field is the process of oxidation induced by air at room temperature referred to as "autoxidation.” Ordinarily, this is a slow process which occurs only to a limited degree. In autoxidation, oxygen reacts with unsaturated fatty acids. Initially, peroxides are formed which in turn break down to hydrocarbons, ketones, aldehydes, and smaller amounts of epoxides and alcohols. Heavy metals present at low levels in fats and oils can promote autoxidation. Fats and oils often are treated with chelating agents such as citric acid to inactivate heavy metals.
  • Glycerides are subject to chemical reactions (oxidation, polymerization, hydrolysis) which can occur particularly during deep fat frying.
  • the extent of these reactions which may be reflected as a decrease in iodine value of the fat and an increase in free fatty acids, depends on the frying conditions, principally the temperature, aeration, and duration.
  • the composition of a frying fat also may be affected by the kind of food being fried. For example, when frying high fat foods such as chicken, some fat from the food will be rendered and blend with the frying fat and some frying fat will be absorbed by the food. In this manner the fatty acid composition of the frying fat will change as frying progresses.
  • the "smoke,” “flash,” and “fire points” of a fatty material are standard measures of its thermal stability when heated in contact with air.
  • the smoke point is the temperature at which smoke is first detected in a laboratory apparatus protected from drafts and provided with special illumination. The temperature at which the fat smokes freely is usually somewhat higher.
  • the flash point is the temperature at which the volatile products are evolved at such a rate that they are capable of being ignited but not capable of supporting combustion.
  • the fire point is the temperature at which the volatile products will support continued combustion. For typical fats with a free fatty acid content of about 0.05%, the smoke, flash, and fire points are around 420°, 620°, and 670° F, respectively.
  • the degree of unsaturation of an oil has little, if any, effect on its smoke, flash, or fire points.
  • Oils containing fatty acids of low molecular weight such as coconut oil, however, have lower smoke, flash, and fire points than other animal or vegetable fats of comparable free fatty acid content.
  • Oils subjected to extended use will have increased free fatty acid content resulting in a lowering of the smoke, flash and fire points. Accordingly used oil freshened with new oil will show an increased smoke, flash and free points.
  • Bailey's Industrial Oil and Fat Products see Bailey's Industrial Oil and Fat Products.
  • Cooking oils are blended with one or more of a low melting point, selective short-chain monounsaturated oil (SSCMO) per se or optionally contained in a carrier oil.
  • SSCMO selective short-chain monounsaturated oil
  • the SSCMO comprises a selective short-chain monounsaturated fatty acid, a selective short-chain monounsaturated fatty alcohol, or a selective short-chain monounsaturated diglyceride or triglyceride having an ester group therein that is the same as the selective short-chain monounsaturated fatty acid without the acid end hydrogen atom.
  • the SSCMO comprises a selective short-chain monounsaturated fatty acid or an alcohol, diglyceride, triglyceride or salt thereof.
  • the cooking oil optionally can also contain generally small amounts of SSCMO.
  • SSCMO SSCMO
  • Such blends have an extended cooking life, an extended high heat stability, as well as an extended taste life.
  • foods selectively up-take more of the SSCMO as opposed to the cooking oil.
  • the inventive cooking oil comprises a blend of
  • the cooking oil comprises a blend formed by combining A) an SSCMO component comprising one or more SSCMO fatty acid oils as described above, or an alcohol, d ⁇ glyceride, triglyceride or salt of such an acid, or a mixture of any of these components with B) one or more cooking oils comprising a vegetable oil, a seed or nut oil, a fish oil, an animal fat, an aquatic plant oil, or any combination thereof.
  • Cooking Oil B may also contain one or more of the above SSCMO components, although this is not required.
  • an optional carrier oil as further described below may also be included in the blend.
  • a method for extending the life of a cooking oil comprises combining A) an SSCMO component comprising one or more SSCMO fatty acid oils as described above, or an alcohol, diglyceride, triglyceride or salt of such an acid, or a mixture of any of these components with B) one or more cooking oils comprising a vegetable oil, a seed or nut oil, a fish oil, an animal fat, an aquatic plant oil, or any combination thereof.
  • Cooking Oil B may also contain one or more of the above SSCMO components, although this is not required.
  • this method may include combining an optional carrier oil, as further described below, with A) and B).
  • this invention provides an edible oil comprising a blend of a vegetable oil and an algae oil, wherein the algae oil comprises
  • SSCMO selective short-chain monounsaturated oil
  • SSCMUFA selected short chain monounsaturated fatty acids
  • this invention provides algae oil containing (a) at least about 20 vol.%, based on the total volume of fatty acid components in the algae oil, of a selective short-chain mono ⁇ nsaturated oil (SSCMO) as described above,
  • this invention provides an extended-life cooking oil comprising a blend of
  • SSCMO selective short-chain monounsaturated oil
  • one or more cooking oils comprising a vegetable oil, a seed or nut oil, a fish oil, an animal fat, an aquatic plant oil, or any combination thereof; wherein the total amount of A) in the blend is sufficient to extend the useful life of the blend when used for deep fat frying of foods by at least 15% relative to an otherwise identical cooking oil B) not blended with A).
  • this invention provides a concentrate comprising a blend of
  • this invention provides a process for extending the useful life of a vegetable oil when used in a method for frying foods in which multiple food items are successively fried in the vegetable oil until the useful life of the vegetable expires after which the vegetable oil is replaced with a fresh batch of vegetable oil, the process comprising selecting as the vegetable oil that is used a vegetable oil composition blended to contain a sufficient amount of a selective short-chain monounsaturated oil (SSCMO) as described above to increase its useful life.
  • SSCMO selective short-chain monounsaturated oil
  • this invention provides a composition for preparing French fried potatoes (pommes frites) comprising
  • a modified vegetable oil modified to contain at least about 4 vol.%, based on the total volume of fatty acid components in the modified vegetable oil, of a C 12 -C 16 methyl-terminated monounsaturated carboxylic acid or derivative in which the carbon atom of the carbonyl group is spaced from the nearer atom of the monounsaturated group by an aliphatic chain of at least 7 carbon atoms, and
  • this invention provides a composition for preparing a fried foodstuff comprising a modified base oil, the base oil
  • Algae oil means a source oil, whether refined or unrefined, which is obtained by treating algae to recover the fatty acids and corresponding alcohols, diglycerides, triglycerides and salts contained therein.
  • algae oil refers to both unmodified algae oil, that is oil derived from algae and not processed to increase the amount of the SSCMO ingredients thereof, as well as to refined algae oil which has been subjected to various processes to increase its SSCMO concentration.
  • Carrier oil means an edible oil containing less than 4 vol.% SSCMO 1 based on the total volume of fatty acid components in the oil, which is intended to be mixed with a source oil, whether refined or unrefined, for the purpose of making concentrate. Normally, the carrier oil will contain less than 1 vol.% SSCMO.
  • Constant means a composition formed by combining a source oil, whether refined or unrefined, with a carrier oil to produce an oil composition containing at least about 20 vol.% SSCMO.
  • Edible oil means an oil which is generally recognized as safe for consumption by humans.
  • Fatty acid components means, in connection with the concentration of a particular fatty acid or derivative in a composition, the total amount of fatty acids and derivatives in the composition.
  • the "fatty acid components” will be understood as including all fatty acids as well as all fatty acid derivatives (Le., ingredients containing fatty acid moieties) such as alcohols, salts and glycerides.
  • “Refined source oil” means a source oil which has been subjected to one or more process steps to increase the concentration of SSCMO therein.
  • "Refining” means a process for treating an oil composition, usually a source oil, to increase the concentration of one or more of its fatty acid (or corresponding alcohol, diglyceride, triglycerides or salt) ingredients.
  • Source oil means an oil product which is recovered by extracting fatty acids and/or their corresponding alcohols, diglycerides, triglycerides and salts from the naturally occurring plant or animal materials in which these ingredients are produced before this oil product is refined to increase it concentration of one or more of these ingredients.
  • SSCMO selective short chain monounsaturated oil
  • SSCMUFA selective short chain monounsaturated fatty acids of interest in this document (i.e., the "SSCMUFA” described immediately below) as well as their corresponding alcohols, diglycerides, triglycerides and salts.
  • SSCMUFA or "selective short chain monounsaturated fatty acid” means the particular fatty acids of interest in this document. As further discussed below, these fatty acids can be described as including palmitoleic (hexadecenoic) acid (C16:ln-7) and its positional isomers C16:ln-6, C16:ln-5, C16:ln-4, and C16:ln-3, myristoleic (tetradecenoic) acid (C14:ln-5) and its positional isomers C14:ln-4 and C14:ln-3, and lauroleic (dodecenoic) acid (C12:ln-3), as well as any combination thereof.
  • palmitoleic (hexadecenoic) acid C16:ln-7) and its positional isomers C16:ln-6, C16:ln-5, C16:ln-4, and C16:ln-3
  • myristoleic (tetradecenoic) acid C14
  • fatty acids can also be described as Ci 2 -C 16 methyl-terminated monounsaturated carboxylic acids in which the carbon atom of the carbonyl group is spaced from the nearer atom of the monounsaturated group by an aliphatic chain of at least 7 carbon atoms.
  • the SSCMO The SSCMO
  • the selective short-chain monounsaturated oils (SSCMO) of the present invention comprise various types of fatty acids, fatty alcohols, and fatty acid diglycerides or triglycerides (and salts).
  • the selective short-chain monounsaturated fatty acids comprise one or more of a palmitoleic (hexadecenoic) acid (C16:ln-7) and its positional isomers C16:ln-6, C16:ln-5, C16:ln-4, and C16:ln-3, myristoleic (tetradecenoic) acid (C14:ln-5) and its positional isomers C14:ln-4 and C14:ln-3, and lauroleic (dodecenoic) acid (C12:ln-3), or any combination thereof, whether as the free acids (i. e. , the "SSCMUFA”) or salts thereof.
  • the SSCMO can also be in the form of a diglyceride or triglycer
  • the above fatty acids can also be described as Ci 2 - Ci 6 methyl-terminated monounsaturated carboxylic acids in which the carbon atom of the carbonyl group is spaced from the nearer atom of the monounsaturated group by an aliphatic chain of at least 7 carbon atoms.
  • “Methyl-terminated” in this context merely means that the terminal carbon atom in the hydrocarbon chain is aliphatic, i.e., the bond between it and its adjacent carbon atom is saturated. It does not imply that this terminal carbon atom must be unsubstituted.
  • these fatty acids as well as alcohols, diglycerides, triglycerides, salts and mixtures thereof can be used in this invention.
  • the selective short-chain monounsaturated fatty alcohols can be derived from the above monounsaturated fatty acids by reduction thereof as known to the literature and to the art as by a strong base such as lithium aluminum hydride.
  • the fatty alcohol derivative will thus have the same number of total carbon atoms therein, will be monounsaturated, and will contain the double bond at the same location as set forth with regard to the monounsaturated fatty acids listed hereinabove.
  • the one or more short-chain monounsaturated fatty acid triglycerides or diglycerides are of course, an ester of the triol glycerol wherein the ester group is the same as the above-noted monounsaturated fatty acid compounds set forth above and thus are fully incorporated by reference.
  • the two, or the three ester groups of the diglyceride and the triglyeride, respectively, can either be all the same (preferred), or two such groups can be the same, or they all can be different.
  • the diglyceride or triglyceride can contain the ester group C16:ln-7, or C16:ln-6, etc.
  • Suitable salts of the above short-chain monounsaturated fatty acids, or the short-chain monounsaturated fatty alcohols, or the short-chain monounsaturated fatty acid di- or triglyceride include the various halides such as chlorine.
  • the melting point (i.e. titer) of the one or more short-chain monounsaturated fatty acids of the present invention are generally about 5°C or less and preferably about 3 0 C or less.
  • the iodine values of the one or more monounsaturated fatty acids are generally from about 80 to 110, desirably from about 82 to about 105, and preferably from about 85 to about 95 with approximately 90 being highly preferred.
  • Desired SSCMO fractions can be readily obtained from various types of oil (i.e., various source oils) such as vegetable oils, seed or nut oils, fish oils, animal fats, or aquatic plants oil, such as salt water or fresh water plants, by conventional cooling and distillation techniques, and/or solvent extraction ("refining" techniques).
  • vegetable oils as well as nut or seed oils are not high in the desired short-chain monounsaturated fatty acid content of the above noted C16:ln-7 series, the C14:ln-5 series and the C12:ln-3.
  • Oil sources that have high amounts of the selective short-chain unsaturated compounds of the present invention include fish oils such as sardine and menhaden that can contain from about 10% to about 16% by weight of C16:ln-7 whereas whale oil can contain about 13% or more by weight.
  • fish oils such as sardine and menhaden that can contain from about 10% to about 16% by weight of C16:ln-7 whereas whale oil can contain about 13% or more by weight.
  • such oils also contain undesirably large amounts of long-chain fatty acids of C20:x and greater that have been reported to contribute to arteriosclerosis and the like.
  • nut oils generally do not have C16:ln-7 fatty acids, an exception is macadamia nut oil that contains C16:ln-7 in amounts of from about 16% to about 25% by total weight of the oil but it also contains other undesirable fatty acids.
  • Animal fats such as butter oil, chicken fat, lard, and beef tallow generally have high contents of C16:ln-7.
  • the selective C16:ln-7, etc., C14:ln-5, etc., and C12:ln-3 short-chain monounsaturated fatty acids ⁇ i.e., the SSCMUFA, as well as the corresponding alcohols, diglycerides, triglycerides and salts) can be extracted from the above-noted types of oil (i.e., the source oils) by initially cooling the oil to a temperature below the solidification or melting point temperature of the desired CI6:ln-7, etc., C14:ln-5, etc., and C12:ln-3, and then removing the remaining liquid portion.
  • oil i.e., the source oils
  • the removed liquid oil can then be subjected to distillation wherein compounds having higher boiling points than the C16:ln-7, etc., C14:ln-5, etc., C12:ln-3, can be removed.
  • the cooling-distillation process can be repeated until the selective short-chain monounsaturated fatty acid (and/or corresponding alcohol, d ⁇ glyceride, triglyceride and/or salt) is obtained in concentrated amounts.
  • various one or more solvents can be utilized that dissolve a selective short-chain monounsaturated fatty acid (and/or corresponding alcohols, diglycerides, triglycerides and salts) but not other components of the oil so that upon vaporization of the solvent, the selective fatty acid (and/or corresponding alcohols, diglycerides, triglycerides and salts) is obtained.
  • a selective short-chain monounsaturated fatty acid and/or corresponding alcohols, diglycerides, triglycerides and salts
  • Such techniques and processes are well known to the art and to the literature. For example, see the description of the same as set forth in U.S. Patent 5,198,250, hereby fully incorporated by reference, such as in Example 1 thereof.
  • high or concentrated amounts of the SSCMO can be obtained such as from about 10% to about 35% or about 50% or about 75% or about 90%, desirably from about 11% to about 30%, and preferably from about 15% to about 25% by volume therein based on the total volume of fatty acid components in the composition.
  • Such refined source oils also desirably contain low amounts of various saturated fatty acid components such as C 12, C 14, C16, and C18, e.g., ⁇ 20 vol.%, ⁇ 15 vol.%, ⁇ 12 vol.%, ⁇ 10 vol.%, and even ⁇ 5 vol.%, based on the total amount of fatty acid components in the composition.
  • the refined source oils also desirably contain low amounts of polyunsaturated fatty acid oil components such as C12:2 or C12:3, C14:2 or C14:3, Cl 6:2 or Cl 6:3, C18:2 or Cl 8:3, and the like, e.g., ⁇ 20 vol.%, ⁇ 15 vol.%, ⁇ 12 vol.%, ⁇ 10 vol.%, and even ⁇ 5 vol.%, based on the total amount of fatty acid components in the composition.
  • polyunsaturated fatty acid oil components such as C12:2 or C12:3, C14:2 or C14:3, Cl 6:2 or Cl 6:3, C18:2 or Cl 8:3, and the like, e.g., ⁇ 20 vol.%, ⁇ 15 vol.%, ⁇ 12 vol.%, ⁇ 10 vol.%, and even ⁇ 5 vol.%, based on the total amount of fatty acid components in the composition.
  • the refined source oils can contain at least about 20 vol.% SSCMO, at least about 30 vol.% SSCMO, at least about 40 vol.% SSCMO, or even at least about 50 vol.% SSCMO.
  • such refined source oils can also contain, if desired, ⁇ 20 vol.%, ⁇ 15 vol.%, ⁇ 12 vol.%, ⁇ 10 vol.%, and even ⁇ 5 vol.% saturated fatty acids, ⁇ 20 vol.%, ⁇ 15 vol.%, ⁇ 12 vol.%, ⁇ 10 vol.%, and even ⁇ 5 vol.% polyunsaturated fatty acids, or both.
  • SSCMO From Algae 10056 Various strains of algae are suitable with regard to producing the desired SSCMO of this invention, i.e., the C16:ln-7, etc., C14:ln-5, etc., and C12:ln-3 described above.
  • the algae can be grown in tanks containing nutrients therein such as phosphates.
  • Numerous strains of algae have relatively high contents of palmitoleic acid such as cyanobacteria, Phormidium sp. NKBG 041105 and Oscillatoria sp. NKBG 091600, that have high cis-palmitoleic acid content (54.5% and 54.4% of total fatty acid, respectively). Phormidium sp.
  • NKBG 041105 had the hightest cis- palmitoleic acid content per biomass (46.3 mg (g dry cell weight) — 1), and cis- palmitoleic acid compostion was found to be constant with varying temperature.
  • other aquatic plants such as sea buckthorn can also be grown and utilized.
  • the algae, sea buckthorn, etc. can then be processed by known techniques such as cooling-distillation or solvent extraction to obtain moderate to high concentrations of C16:ln-7, etc., C14:ln-5, etc., and C12:ln-3, oil fractions.
  • the algae oils of the present invention can be utilized per se, i.e., unmodified (“source oils”), or refined so that they have significant amounts of one or more SSCMO components therein (“refined source oils”). These algae oils also desirably have low amounts of saturated oils as well as low amounts of polyunsaturated oils, hi other words, these algae oils can be refined in the same way as the other source oils, as described above, to produce algae source oils having the same ingredient concentrations described above.
  • algae oils are used as the predominant source of SSCMO for making the oil blends of this invention, it may be desirable at least in some embodiments to limit the amount of other sources of SSCMO for formulating these blends. That is to say, it may be desirable in these embodiments to limit the amount of other oils high in SSCMO concentration used to make these blends, as this may help in limiting the amount of undesirable oils (e.g., saturated and polyunsaturated oils) in these blends.
  • undesirable oils e.g., saturated and polyunsaturated oils
  • algae oils when used as the source of the SSCMO, it may be desirable to limit the total amount of macadamia nut oil, animal fat oil such as butter fat, chicken fat oil, lard, beef tallow, various fish oils such as shrimp oil, menhaden oil, and menhaden PHO oil, whale oil and the like used to these same blends to no more than about 5% or less, desirably no more than about 3%, more desirably no more than about 1% by volume based on the total amount of fatty acid components in the composition.
  • animal fat oil such as butter fat, chicken fat oil, lard, beef tallow
  • various fish oils such as shrimp oil, menhaden oil, and menhaden PHO oil, whale oil and the like used to these same blends to no more than about 5% or less, desirably no more than about 3%, more desirably no more than about 1% by volume based on the total amount of fatty acid components in the composition.
  • Microalgae are the most primitive form of plants. While the mechanism of photosynthesis in microalgae is similar to that of higher plants, they are generally more efficient converters of solar energy because of their simple cellular structure. In addition, because the cells grow in aqueous suspension, they have more efficient access to water, CO 2 , and other nutrients. For these reasons, microalgae are capable of producing at least 30 times the amount oil per unit area of land, compared to terrestrial oilseed crops. Thus, microalgae are very efficient plants that are capable of taking waste or carbon dioxide and converting it to a high density liquid form of oil.
  • algae can be produced by bubbling carbon dioxide such as from a power plant into a pond containing the algae, m one such embodiment, the ponds have a raceway design in which the algae, water and nutrients such as potassium and phosphorus circulate around a racetrack. Paddlewheels can be used to provide flow. The algae are thus kept suspended in water. Algae are circulated back up to the surface at a regular frequency. The ponds are kept shallow to keep the algae exposed to sunlight in view of the limited depth to which sunlight can penetrate pond water. The ponds are operated continuously. That is, water and nutrients are constantly fed to the pond, while algae-containing water is removed at the other end. Some kind of harvesting system is required to recover the algae, which contains substantial amounts of natural oil.
  • Diatoms (Bacillariophyceae). These algae dominate the phytoplankton of the oceans, but are also found in fresh and brackish water. Approximately 100,000 species are known to exist. Diatoms contain polymerized silica (Si) in their cell walls. All cells store carbon in a variety of forms. Diatoms store carbon in the form of natural oils or as a polymer of carbohydrates known as chyrosolaminarin.
  • the green algae (Chlorophyseae). These are also quite abundant, especially in freshwater. They can occur as single cells or as colonies. Green algae are the evolutionary progenitors of modern plants. The main storage compound for green algae is starch, though oils can be produced under certain conditions.
  • the blue algae (Cyanophyceae). Much closer to bacteria in structure and organization, these algae play an important role in fixing nitrogen from the atmosphere. There are approximately 2,000 known species found in a variety of habitats.
  • the golden algae (Chrysophyceae), This group of algae is similar to the diatoms. They have more complex pigment systems, and can appear yellow, brown or orange in color. Approximately 1,000 species are known to exist, primarily in freshwater systems. They are similar to diatoms in pigmentation and biochemical composition. The golden algae produce natural oils and carbohydrates as storage compounds.
  • Any algae which produces the SSCMO component described above can be used to formulate the oil blends of this invention.
  • Specific examples are identified in the following Table 1: naturally derived from algae (Le., algae oil per se) but most often derived by refinement of the oil are generally any of the numerous types of algae plants that are known to exist as well as other algae plants not yet identified. The following is a list of strains being maintained and generally contain fatty acid oils and hence can be used in the present invention.
  • Table 1 Micraalgal Strains for Producing SSCMO
  • enus S nechococcus strains containin monounsaturated fatt acids
  • suitable amounts of SSCMO monounsaturated fatty acid components are naturally produced by algae.
  • the first six examples yield high amounts of polyunsaturated fatty acid components and the same are desirably reduced by refining.
  • undesirable amounts of saturated fatty acid components are also produced and the same are desirably refined out of the algae oil in a manner as noted hereinabove.
  • Suitable low levels of both saturated fatty acid and polyunsaturated fatty acid components are set forth hereinabove such as being generally less than about 20% by volume, desirably less than about 15% by volume and preferably less than about 10% by volume based upon the total volume of all the fatty acid components in the composition.
  • Algae strain 6808 is an example of an algae oil that can be utilized per se, i.e. a natural oil and not modified or refined inasmuch as the monounsaturated oil components such as C16 and C14 are very high, approximately 59% by volume of the algae oil fatty acid components whereas the amount of saturated fatty acid components is about 27% by volume of the algae oil and the amount of polyunsaturated components is very low, for example about 3% by volume of the algae oil.
  • Suitable algae containing fatty acids include those set forth in WO 2008/036654, published March 27, 2008, hereby fully incorporated by reference. As set forth in Figure 1 thereof, the algae strains of Bidduphia aurita, Crypthecodinium cohnii, Nitzschia alba, and Skeletonema costatum contain significant amounts of C16:l and C14:l that can be utilized as a source of the SSCMO monounsaturated fatty acid components of the present invention.
  • the SSCMO component can be blended with one or more liquid cooking oils at the end use site, such as a fast food restaurant, for cooking foods such as fruits, vegetables, meats, fish, and grains that are administered or fed to animals or humans.
  • the SSCMO can be in substantially a pure form or optionally but desirably is contained in a carrier oil that independently can be the same type of oil as the cooking oil but (because of the added SSCMO) has high amounts of SSCMO therein.
  • the carrier oil can be a fish oil or chicken fat, etc.
  • a cooking oil can be olive oil, canola oil, palm oil, or coconut oil, etc.
  • the carrier oil can also be a vegetable oil such as olive oil, canola oil, palm oil, or coconut oil, etc.
  • the amount of the SSCMO can be from about 3% to about 100%, and desirably from about 5%, or about 10%, or about 15%, or about 20% to about 30%, or about 50%, or about 70% or about 90% by volume based upon the total volume of the SSCMO and the carrier oil, based on the entire volume of fatty acid component is the concentrate.
  • the amount of SSCMO in the concentrate is at least about 20 vol.%, at least about 30 vol.%, at least about 40 vol.%, and even at least about 50 vol.%, are contemplated.
  • Such concentrates desirably, may also contain no more than about 20 vol.% polyunsaturated fatty acids, no more than about 20 vol.% saturated fatty acids, or both.
  • Such concentrates may also contain no more than about 20 vol.%, or even 10 vol.%, of Cl 8 and Cl 8+ monounsaturated fatty acids. Such concentrates may also contain >40 vol.%, >50 vol.% or even >60 vol.% carrier oils.
  • the SSCMO per se or desirably the same in a carrier oil may be added to and blended with a cooking oil.
  • the carrier oil and independently, the cooking oil can be hydrogenated or partially hydrogenated, and contain saturated fats or polyunsaturated fats as well as conventional monounsaturated fats such as oleic acid, i.e. C 18:1.
  • oils i.e. the cooking oil and the carrier oil whether hydrogenated or preferably nonhydrogenated, independently, as noted above, can be vegetable oils, seed or nut oils, fish oils, animal fats that if a solid become an oil upon heating, and aquatic plant oils.
  • Suitable vegetable oils include coconut, palm kernel, cocoa butter, corn, cottonseed, olive, peanut, rapeseed, canola, safflower, high oleic saf ⁇ lower, soybean, sunflower, and high oleic sunflower.
  • seed and nut oils include macadamia, peanut, almond, cashew, pecan, walnut, and sesame seed.
  • Fish oils include any type of fish such as tilapia, salmon, tuna, halibut, sardine, menhaden, blue fish, and the like.
  • Animal fats that are soluble at higher temperatures include butter oil, chicken fat, lard (which is beef fat), tallow (beef), horse fat, horse milk, pigs, and the like.
  • Aquatic plant oils can be derived from plants that grow either in salt water or fresh water (not salt) or both and include seaweed, sea buckthorn, various strains of algae as noted above, and the like. Various mixtures or combinations of various types of oils such as vegetable oil, fish oil, etc., can also be utilized.
  • the cooking oils are generally vegetable oils inasmuch as the same are readily available and economical.
  • the cooking oils can contain one or more SSCMO compounds although the amount thereof is generally small, that is usually less than about 4% by volume, often less than about 1% by volume, and even less than about 0.5% by volume based upon total volume of cooking oil and the SSCMO compound therein (Le., based on the total volume of fatty acid components in the cooking oil.)
  • the total amount utilized of the one or more SSCMO per se or contained a carrier oil as well as the one or more total amounts of SSCMO contained in the cooking oil generally is from about 4% to about 15%, desirably from about 6% to about 14%, and preferably from about 8% to about 12% by volume based upon all of the SSCMO, regardless of source, for example in the carrier oil and the cooking oil, and the total amount of all carrier oils and cooking oils not counting the SSCMO therein (i.e., based on the total volume of fatty acid components in the finished blend).
  • the remaining percent volume or difference constitutes only the cooking oil and any optional carrier oil per se, that is not any SSCMO therein.
  • the key aspect is that one or more SSCMO compounds regardless of source (i.e. carrier oil or cooking oil) be utilized in sufficient amounts so that when blended with a cooking oil, the above noted improved properties are obtained.
  • concentration of the SSCMO in the cooking oil blend of this invention is at least about 4 vol.%, at least about 6 vol.%, at least about 8 vol.%, and even at least about 10 vol.%, based on the total amount of fatty acid components in the cooking oil blend as a whole.
  • Embodiments in which the useful life of the oil is extended by at least about 30%, at least about 50%, at least about 70%, and even at least about 90% are contemplated. Improvements in other "cooking properties" of the inventive cooking oil blends, e,g. , stability of cooking oil at elevated temperatures and preferential take-up of the SSCMO by the cooked foods, have also been found.
  • mixtures of the one or more of the selective short-chain monounsaturated fatty acids, or short chain monounsaturated fatty alcohols, or the short-chain monounsaturated di- or triglycerides (i.e., the SSCMO) with one or more of the above-noted cooking oils has been found yield unexpected results with regard to cooking oil life, stability of cooking oil at elevated temperatures, longer retention times of taste before the oil mixture becomes bitter, and better take-up by foods of the selective short-chain monounsaturated oil such as C16:ln-7 etc.
  • the SSCMO modified cooking oil of the present invention can be used for baking, grilling, and broiling various foods and is desirably utilized for frying food.
  • any type of food can be utilized, such as any type vegetable, for example broccoli, squash, potatoes, and the like, any type of fruit such as bananas, apples, and the like, any type of bread including breaded products such as breaded fruit, vegetables, or meat, any type of cheese, and any type of meat such as beef, lamb, poultry, and fish.
  • the life extension of a cooking oil was at least about 15%, desirably at least about 30% or at least about 50% and more desirably at least about 70% and preferably at least about 90%.
  • the increased stability time at an elevated temperature of 355°F was at least about 20%, desirably at least about 30%, and preferably at least about 40%.
  • the taste retention was maintained at least about 3 days, desirably at least about 5 days or at least about 7 days, and preferably at least about 9 days or at least about 11 days.
  • the take-up content of the SSCMO of the present invention was increased generally at least about 20%, desirably at least about 30%, and preferably at least about 40% or at least about 50% by volume after nine days.
  • a 75% by volume of a macadamia nut oil was blended with 25% by volume of a base oil that was a partially hydrogenated canola based vegetable cooking oil.
  • the resulting blend contained approximately 13.4% by volume of C16:ln-7 therein.
  • This blend of oil was utilized to fry breaded chicken 40 times a day at 355°F for 4 minutes for each flying cycle.
  • a separate example of the same oil was utilized to fry breaded fish 40 times a day at 355 0 F for 4 minutes for each frying cycle.
  • the blend of the oil mixture of the present invention did not fail, i.e. develop a bad taste or become unstable, until after 11 or 12 days of usage.
  • the partially hydrogenated canola based vegetable cooking oil when utilized the same number of times per day at the same temperature for the same number of minutes for each frying sample with regard to both breaded chicken and breaded fish began to fail after 7 days.
  • the cooking oil blend of the present invention containing SSCMO such as C16:ln-7 etc. yielded a cooking life extension of from about 57% to about 71%.
  • a cooking oil blend of 25% by volume of a macadamia nut oil and 75% by volume of Melfry ® partially hydrogenated vegetable cooking oil was blended to yield a cooking oil having approximately 4.5% by volume of C16:ln-7 derived from the macadamia nut oil.
  • This blend was utilized to fry potatoes (French style), i.e. 500 pounds.
  • This experimental blend was taste tested by people and generally it was reported that at the end of three days the french fries had better taste, crispness, texture and color, as compared to the same amount of french fries fried in Melfry ® partially hydrogenated vegetable cooking oil after 3 days that was favored by only 1% of the taste testers.
  • a cooking oil mixture was made containing 75% by volume of macadamia nut oil and 25% by volume of a base oil that was partially hydrogenated canola based cooking oil.
  • the volume of C16:ln-7 derived from the macadamia nut oil was about 13.4% based on the total volume of the macadamia nut oil and partially hydrogenated canola based cooking oil.
  • This mixture of oil was utilized to fry breaded chicken 40 times a day at 355°F for 4 minutes for each fry cycle.
  • a separate sample of same oil was utilized to fry breaded fish 40 times a day at 355°F for 4 minutes for each fry cycle.
  • the oil utilized for the chicken as well as the oil utilized for frying the breaded fish were separately sampled at the end of 3 days, 6 days, and 9 days and the percentage volume of various fatty acids was determined and the same is set forth in Table 4.
  • the take-up food ratio of monounsaturated fats to the saturated and polyunsaturated fats is furthermore increased inasmuch as the cooking oil removed some of the saturated and polyunsaturated fats from the food product.
  • Scientific data generally states that higher amounts of monounsaturated fats are healthy for human beings such as with respect to lower total cholesterol, lower triglycerides, and lower LDL values.

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Abstract

L'invention concerne l'extension de la durée de vie utile d'une huile de cuisson par l'inclusion dans l'huile d'huiles à base d'acide palmitoléïque et/ou d'analogues de celles-ci. Certaines souches d'algue représentent une source abondante de ces additifs huileux.
PCT/US2009/034649 2008-02-20 2009-02-20 Huiles mono-insaturées à chaîne courte sélectives WO2009105620A1 (fr)

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Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015011307A1 (fr) * 2013-07-26 2015-01-29 Universidad De Cádiz (Otri) Produit alimentaire bénéfique pour la santé
WO2015164550A1 (fr) * 2014-04-23 2015-10-29 Solazyme, Inc. Utilisations d'ordre alimentaire d'une huile à haute stabilité
US9200236B2 (en) 2011-11-17 2015-12-01 Heliae Development, Llc Omega 7 rich compositions and methods of isolating omega 7 fatty acids
US9249252B2 (en) 2013-04-26 2016-02-02 Solazyme, Inc. Low polyunsaturated fatty acid oils and uses thereof
US9255282B2 (en) 2010-05-28 2016-02-09 Solazyme, Inc. Tailored oils produced from recombinant heterotrophic microorganisms
US9353389B2 (en) 2008-11-28 2016-05-31 Solazyme, Inc. Nucleic acids useful in the manufacture of oil
US9388435B2 (en) 2010-11-03 2016-07-12 Terravia Holdings, Inc. Microbial oils with lowered pour points, dielectric fluids produced therefrom, and related methods
US9394550B2 (en) 2014-03-28 2016-07-19 Terravia Holdings, Inc. Lauric ester compositions
US9499845B2 (en) 2011-05-06 2016-11-22 Terravia Holdings, Inc. Genetically engineered microorganisms that metabolize xylose
US9551017B2 (en) 2012-04-18 2017-01-24 Terravia Holdings, Inc. Structuring fats and methods of producing structuring fats
US9719114B2 (en) 2012-04-18 2017-08-01 Terravia Holdings, Inc. Tailored oils
US9969990B2 (en) 2014-07-10 2018-05-15 Corbion Biotech, Inc. Ketoacyl ACP synthase genes and uses thereof
US10053715B2 (en) 2013-10-04 2018-08-21 Corbion Biotech, Inc. Tailored oils
US10100341B2 (en) 2011-02-02 2018-10-16 Corbion Biotech, Inc. Tailored oils produced from recombinant oleaginous microorganisms
US10119947B2 (en) 2013-08-07 2018-11-06 Corbion Biotech, Inc. Protein-rich microalgal biomass compositions of optimized sensory quality
US10138435B2 (en) 2007-06-01 2018-11-27 Corbion Biotech, Inc. Renewable diesel and jet fuel from microbial sources
US10264809B2 (en) 2013-01-28 2019-04-23 Corbion Biotech, Inc. Microalgal flour
WO2020240261A1 (fr) * 2019-05-31 2020-12-03 Tarzi Bahareh Procédé de combinaison d'huile de colza et de safran

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5198250A (en) * 1990-07-16 1993-03-30 Lipotech Partners Limited Partnership Food and pharmaceutical compositions containing short chain monounsaturated fatty acids and methods of using
US20030215557A1 (en) * 2002-05-20 2003-11-20 Gus Papathanasopoulos Micro-molecular hyper-saturation of conventional cooking oils for high altitude and confined space applications
WO2006006856A1 (fr) * 2004-07-13 2006-01-19 Friesland Brands B.V. Compositions en poudre contenant une huile comestible et leur utilisation dans des produits alimentaires
US20060247454A1 (en) * 2001-02-01 2006-11-02 Carolina Soy Products Llc Vegetable oil process
US20070243307A1 (en) * 2006-04-11 2007-10-18 Martek Biosciences Corporation Food Products Comprising Long Chain Polyunsaturated Fatty Acids and Methods for Preparing the Same

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5198250A (en) * 1990-07-16 1993-03-30 Lipotech Partners Limited Partnership Food and pharmaceutical compositions containing short chain monounsaturated fatty acids and methods of using
US20060247454A1 (en) * 2001-02-01 2006-11-02 Carolina Soy Products Llc Vegetable oil process
US20030215557A1 (en) * 2002-05-20 2003-11-20 Gus Papathanasopoulos Micro-molecular hyper-saturation of conventional cooking oils for high altitude and confined space applications
WO2006006856A1 (fr) * 2004-07-13 2006-01-19 Friesland Brands B.V. Compositions en poudre contenant une huile comestible et leur utilisation dans des produits alimentaires
US20070243307A1 (en) * 2006-04-11 2007-10-18 Martek Biosciences Corporation Food Products Comprising Long Chain Polyunsaturated Fatty Acids and Methods for Preparing the Same

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10138435B2 (en) 2007-06-01 2018-11-27 Corbion Biotech, Inc. Renewable diesel and jet fuel from microbial sources
US9353389B2 (en) 2008-11-28 2016-05-31 Solazyme, Inc. Nucleic acids useful in the manufacture of oil
US9279136B2 (en) 2010-05-28 2016-03-08 Solazyme, Inc. Methods of producing triacylglyceride compositions comprising tailored oils
US9657299B2 (en) 2010-05-28 2017-05-23 Terravia Holdings, Inc. Tailored oils produced from recombinant heterotrophic microorganisms
US9255282B2 (en) 2010-05-28 2016-02-09 Solazyme, Inc. Tailored oils produced from recombinant heterotrophic microorganisms
US10006034B2 (en) 2010-05-28 2018-06-26 Corbion Biotech, Inc. Recombinant microalgae including keto-acyl ACP synthase
US10167489B2 (en) 2010-11-03 2019-01-01 Corbion Biotech, Inc. Microbial oils with lowered pour points, dielectric fluids produced therefrom, and related methods
US10344305B2 (en) 2010-11-03 2019-07-09 Corbion Biotech, Inc. Microbial oils with lowered pour points, dielectric fluids produced therefrom, and related methods
US9388435B2 (en) 2010-11-03 2016-07-12 Terravia Holdings, Inc. Microbial oils with lowered pour points, dielectric fluids produced therefrom, and related methods
US10100341B2 (en) 2011-02-02 2018-10-16 Corbion Biotech, Inc. Tailored oils produced from recombinant oleaginous microorganisms
US9499845B2 (en) 2011-05-06 2016-11-22 Terravia Holdings, Inc. Genetically engineered microorganisms that metabolize xylose
US9200236B2 (en) 2011-11-17 2015-12-01 Heliae Development, Llc Omega 7 rich compositions and methods of isolating omega 7 fatty acids
US10287613B2 (en) 2012-04-18 2019-05-14 Corbion Biotech, Inc. Structuring fats and methods of producing structuring fats
US9551017B2 (en) 2012-04-18 2017-01-24 Terravia Holdings, Inc. Structuring fats and methods of producing structuring fats
US10683522B2 (en) 2012-04-18 2020-06-16 Corbion Biotech, Inc. Structuring fats and methods of producing structuring fats
US9719114B2 (en) 2012-04-18 2017-08-01 Terravia Holdings, Inc. Tailored oils
US11401538B2 (en) 2012-04-18 2022-08-02 Corbion Biotech, Inc. Structuring fats and methods of producing structuring fats
US9909155B2 (en) 2012-04-18 2018-03-06 Corbion Biotech, Inc. Structuring fats and methods of producing structuring fats
US10264809B2 (en) 2013-01-28 2019-04-23 Corbion Biotech, Inc. Microalgal flour
US9249252B2 (en) 2013-04-26 2016-02-02 Solazyme, Inc. Low polyunsaturated fatty acid oils and uses thereof
ES2539844A1 (es) * 2013-07-26 2015-07-06 Universidad De Cádiz Producto alimenticio saludable
WO2015011307A1 (fr) * 2013-07-26 2015-01-29 Universidad De Cádiz (Otri) Produit alimentaire bénéfique pour la santé
US10119947B2 (en) 2013-08-07 2018-11-06 Corbion Biotech, Inc. Protein-rich microalgal biomass compositions of optimized sensory quality
US10053715B2 (en) 2013-10-04 2018-08-21 Corbion Biotech, Inc. Tailored oils
US9796949B2 (en) 2014-03-28 2017-10-24 Terravia Holdings, Inc. Lauric ester compositions
US9394550B2 (en) 2014-03-28 2016-07-19 Terravia Holdings, Inc. Lauric ester compositions
WO2015164550A1 (fr) * 2014-04-23 2015-10-29 Solazyme, Inc. Utilisations d'ordre alimentaire d'une huile à haute stabilité
US10316299B2 (en) 2014-07-10 2019-06-11 Corbion Biotech, Inc. Ketoacyl ACP synthase genes and uses thereof
US9969990B2 (en) 2014-07-10 2018-05-15 Corbion Biotech, Inc. Ketoacyl ACP synthase genes and uses thereof
WO2020240261A1 (fr) * 2019-05-31 2020-12-03 Tarzi Bahareh Procédé de combinaison d'huile de colza et de safran

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