WO2009105620A1 - Selective short chain monounsaturated oils - Google Patents

Abstract

The useful life of a cooking oil is extended by including in the oil palmitoleic acid based oils and/or analogs. Certain strains of algae represent a fertile source of these oil additives.

Description

UMTED STATES PATENT APPLICATION

TITLE OF THE INVENTION

SELECTIVE SHORT CHAIN MONOUNSATURATED OILS

RELATED APPLICATION

[0001] This patent document claims the benefit and priority of U.S. provisional application 61/066,370, filed February 20, 2008 for SELECTIVE SHORT CHAIN MONOUNSATURATED OILS, which is incorporated by reference in its entirety.

FIELD OF THE INVENTION

10002] 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. 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.

BACKGROUND OF THE INVENTION

[0003] Heretofore, 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.

[0004] With regard to lipids in and the pathology of cooking oils, the following is noted:

[0005] Unsaturated fatty acids have a vinylic or carbon-carbon double bond at one or more positions along the acyl hydrocarbon chain. Hereinafter 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.

[0006] One established approach to reducing plasma cholesterol levels is to consume a large proportion of dietary triglycerides as polyunsaturated fatty acid (PUFA) derivatives. 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). This well established lowering of plasma LDL cholesterol concentration when PUFAs are substituted for dietary saturated fatty acids provides the rationale for the widespread substitution of a variety of vegetable oils for animal fats in cooking and food formulations. The American Heart Association in its Phase I and Phase 13 Recommended Diets has approved the use of PUFAs as part of a large scale dietary modification for the purpose of lowering cholesterol levels in the general population. See, e.g., S. M. Grundy, Disorders of Lipids and Lipoproteins, in Interna] Medicine, Stein, ed. 2035, 2046 (2nd ed. 1987).

[0007] However, 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) is activated towards free-radical substitution reactions by both of the adjacent vinylic groups. Consequently this methylene carbon reacts 10 to 20 times more readily in free radical reactions than does a methylene adjacent to only a single vinyl group. Their susceptibility to peroxidation and polymerization reactions implicates PUFAs in several undesirable processes such as tissue aging and tumorigenesis. PUFAs have been implicated in increasing the incidence of human bowel cancer, in suppression of the immune system, in increasing the risk of cholesterol gallstones, and in promoting the oxidation of LDL trapped within the arterial wall.

[0008] Moreover, 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.

[0009J Because of these drawbacks of PUFAs, some investigators have advocated the use of monounsaturated fatty acids (MUFAs). In particular, oleic acid (C18:ln-9) has been suggested as a nonatherogenic substitute for PUFAs. Oleic acid is a major component of olive oil, and some epidemiological evidence suggests that Mediterranean populations with high olive oil consumption have a reduced incidence of atherosclerosis and associated heart disease. Controlled human feeding studies, in which oleic acid was compared versus linoleic acid or saturated fats, reveal that oleic acid lowers serum LDL cholesterol about as well as does linoleic acid. However, unlike linoleic acid, 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).

[0010] 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 method involves oral or parenteral administration of alpha, betaunsarurated fatty acids of the structure H₃C(CH₂XCH=CHCOOH, where n=10, 12, 14, or 16. The fatty acids disclosed are therefore C14:ln-12, C16:ln-14, C18:lπ-16, and C20:ln-18.

[0011] With regard to the reactions of fats and oils, the following is noted:

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.

B. Oxidation of Fats

[0013] 1. 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.

[0014] The result of the autoxidation of fats and oils is the development of objectionable flavors and odors characteristic of the condition known as "oxidative rancidity." Some fats resist this change to a remarkable extent while others are more susceptible depending on the degree of unsaturation, the presence of antioxidants, and other factors. The presence of light, for example, increases the rate of oxidation. It is a common practice in the industry to protect fats and oils from oxidation to preserve their acceptable flavor and shelf life.

[0015] When rancidity has progressed significantly, it is apparent from the flavor and odor of the oil. Expert tasters are able to detect the development of rancidity in its early stages. The peroxide value determination, if used judiciously, may be helpful in measuring the degree of oxidative rancidity in the fat. [0016] It has been found that oxidatively abused fats can complicate nutritional and biochemical studies in animals because they can affect food consumption under ad libitum feeding conditions and reduce the vitamin content of the food. If the diet has become unpalatable due to excessive oxidation of the fat component and is not accepted by the animal, a lack of growth by the animal could be due to its unwillingness to consume the diet. Thus, the experimental results might be attributed unwittingly to the type of fat or other nutrient being studied rather than to the condition of the ration. Knowing the oxidative condition of unsaturated fats is extremely important in biochemical and nutritional studies with animals.

[0017] 2. Oxidation at Higher Temperatures. Although the rate of oxidation is greatly accelerated at higher temperatures, oxidative reactions which occur at higher temperatures may not follow precisely the same routes and mechanisms as the reactions at room temperatures. Thus, differences in the stability of fats and oils often become more apparent when the fats are used for frying or slow baking. The more unsaturated the fat or oil, the greater will be its susceptibility to oxidative rancidity. Predominantly unsaturated oils such as soybean, cottonseed, or corn oil are less stable than predominantly saturated oils such as coconut oil. Oxidative stability has been increased in many of the oils developed through biotechnological engineering. The stability of a fat or oil may be predicted to some degree by the oxidative stability index (OSI).

C. Polymerization of Fats

[0018] All commonly used fats and particularly those high in polyunsaturated fatty acids tend to form some larger molecules known broadly as polymers when heated under extreme conditions of temperature and time. Under normal processing and cooking conditions polymers are formed in insignificant quantities. Although the polymerization process is not understood completely, it is believed that polymers in fats and oils arise by formation of either carbon to carbon bonds or oxygen bridges between molecules. When an appreciable amount of polymer is present, there is a marked increase in viscosity. Animal studies have shown that any polymers that may be present in a fat or oil are absorbed poorly from the intestinal tract and are excreted as such in the feces. D. Reactions during Heating and Cooking

[0019} 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. Since absorption of fat by the fried food may be extensive, it is often necessary to replenish the fryer with fresh fat. This replacement with fresh fat tends to dilute overall compositional changes of the fat during prolonged frying. Frying conditions do not, however, saturate the unsaturated fatty acids, although the ratio of saturated to unsaturated fatty acids will change due to some polymerization of unsaturated fatty acids.

[0020] It is the usual practice to discard frying fat when (1) prolonged frying causes excessive foaming of the hot fat, (2) the fat tends to smoke excessively, usually from prolonged frying with low fat turnover, or (3) an undesirable flavor or dark color develops. Any or all of these qualities associated with the fat can decrease the quality of the fried food.

[00211 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. For additional details see Bailey's Industrial Oil and Fat Products.

[0022] Considerable work has been done studying the effects of elevated temperatures on the composition and biological qualities of edible fats and oils. Much of this work has been done with temperatures and other conditions which simulated those experienced in commercial deep frying operations, such as in restaurants or food processing establishments. Other studies, however, have exposed the foods to exaggerated conditions that are unrealistic and not indicative of actual use conditions. Under these unrealistic conditions, some substances are formed in small amounts that when isolated and fed at concentrated levels can be shown to be toxic to laboratory animals. The practical significance of these observations was defined more clearly in a two-year animal feeding study by Nolen et al. This work showed that animals consuming used typical frying fats as the sole source of fat in the diet throughout their life span thrived equally as well as control animals consuming the same fat that had not been subjected to frying conditions. Clark, et al. also have reviewed the nutritional aspects of heated fats.

SUMMARY OF THE INVENTION

|0023] 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. 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. (In other words, the SSCMO comprises a selective short-chain monounsaturated fatty acid or an alcohol, diglyceride, triglyceride or salt thereof. Mixtures of these ingredients can also be used.) The cooking oil optionally can also contain generally small amounts of SSCMO. Such blends have an extended cooking life, an extended high heat stability, as well as an extended taste life. Moreover, foods selectively up-take more of the SSCMO as opposed to the cooking oil.

[0024] In general, the inventive cooking oil comprises a blend of

A) one or more selective short chain monounsaturated oils (SSCMO) per se or optionally in a carrier oil, said SSCMO comprising one or more of a) a selective short chain monounsaturated fatty acid (SSMUFA) comprising C16:ln-7, C16:ln-6, C16:ln-5, C16:ln-4, C16:ln-3, C14:ln-5, C14:ln-4, C14:ln-3, or C12:ln-3, or any combination thereof; or b) a selective short chain monounsaturated fatty alcohol derived from said a) selective fatty acid, or c) a selective short chain monounsaturated triglyceride or diglyceride containing said a) selective fatty acid, or d) salts of any of said a, b, or c, or, any combination of a, or b, or c, or d; said optional carrier oil comprising one or more of a vegetable oil, a seed or nut oil, a fish oil, an animal fat, an aquatic plant oil, or any combination thereof; and

B) one or more cooking oils optionally and independently containing one or more SSCMO (as defined above), said one or more cooking oils, independently, comprising a vegetable oil, a seed or nut oil, a fish oil, an animal fat, an aquatic plant oil, or any combination thereof. 10025] In other words, 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, dϊglyceride, 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. In addition, an optional carrier oil as further described below may also be included in the blend.

10026] 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. Moreover, this method may include combining an optional carrier oil, as further described below, with A) and B).

]0027] In accordance with another aspect of this invention, it has also been found that various strains of algae represent a fertile source for the SSCMO of this invention.

[0028] Thus, in one embodiment, this invention provides an edible oil comprising a blend of a vegetable oil and an algae oil, wherein the algae oil comprises

(a) at least about 20 vol.%, based on the total volume of fatty acid components in the algae oil, of a selective short-chain monounsaturated oil (SSCMO) comprising one or more selected short chain monounsaturated fatty acids (SSCMUFA) selected from C16:ln-7, C16:ln-6, C16:ln-5, C16:ln-4, C16:ln-3, C14:ln-5, C14:lnΛ C14:ln-3, C12:ln-3, or any combination thereof, or an alcohol, diglyceride, triglyceride or salt of said SCMUFA, or mixtures thereof,

(b) no more than about 20 vol.% saturated fatty acids, and

(c) no more than about 20 vol.% polyunsaturated fatty acids.

[0029] In another embodiment, 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 monoυnsaturated oil (SSCMO) as described above,

(b) no more than about 20 vol.% saturated fatty acids, and

(c) no more than about 20 vol.% polyunsaturated fatty acids.

[0030] In still another embodiment, this invention provides an extended-life cooking oil comprising a blend of

A) a selective short-chain monounsaturated oil (SSCMO) as described above, and

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; 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).

[0031] hi yet another embodiment, this invention provides a concentrate comprising a blend of

(A) a source oil, the source oil being unrefined or refined, or a mixture of unrefined and refined source oils, the source oil comprising

(a) at least about 40 vol.%, based on the total volume of fatty acid components in the source oil, of a selective short-chain monounsaturated oil (SSCMO) as described above,

(b) no more than about 20 vol.% saturated fatty acids, and

(c) no more than about 20 vol.% polyunsaturated fatty acids, and

(B) a carrier oil, the carrier oil containing less than 4 vol.% SSCMO, based on the total volume of fatty acid components in the carrier oil, wherein the concentrate comprises at least about 20 vol.% SSCMO, based on the total volume of fatty acid components in the concentrate.

[0032] In still another embodiment, 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.

[0033] In yet another embodiment, this invention provides a composition for preparing French fried potatoes (pommes frites) comprising

(a) 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 C₁₂-C₁₆ 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

(b) potatoes.

[0034] In still another embodiment, this invention provides a composition for preparing a fried foodstuff comprising a modified base oil, the base oil

(i) being selected from a vegetable oil, seed oil, nut oil, fish oil, animal fat, aquatic plant oil, or mixtures thereof, which contains less than 4 vol.%, based on the total volume of fatty acid components in the base oil, of a Q₂-C₁₆ 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,

(ii) having been modified by blending or refining or both to contain at least about 4 vol.% of this C^-C₁₆ methyl-terminated monounsaturated carboxylic acid or derivative oil, and

(iii) being heated hot enough to fry the foodstuff. DETAILED DESCRIPTION Terminology

[0035] Unless otherwise indicated expressly or by context, the following terms have the following meanings in this document:

10036] "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. Thus it will be understood that "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.

10037] "Carrier oil" means an edible oil containing less than 4 vol.% SSCMO₁ 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.

[0038] "Concentrate" 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.

[0039] "Edible oil" means an oil which is generally recognized as safe for consumption by humans.

[0040] "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. For example, in a composition described as containing "13 vol.% oleic acid based on the fatty acid components 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.

[0041] "Refined source oil" means a source oil which has been subjected to one or more process steps to increase the concentration of SSCMO therein. [0042] "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.

[0043] "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.

[0044] "SSCMO" or "selective short chain monounsaturated oil" refers to the portion of an oil composition composed solely of the 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.

[0045] "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. These fatty acids can also be described as Ci₂-C₁₆ 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

[0046] 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 triglyceride. Mixtures of these SSCMO ingredients can also be used.

[0047] The above fatty acids (i.e., the "SSCMUFA") can also be described as Ci₂- Ci₆ 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. As indicated above, these fatty acids as well as alcohols, diglycerides, triglycerides, salts and mixtures thereof can be used in this invention.

[0048] 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.

[0049] 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. Thus, the diglyceride or triglyceride can contain the ester group C16:ln-7, or C16:ln-6, etc.

[0050] 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.

[0051] 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 3⁰C 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.

Obtaining the SSCMO

[0052J The above selected short-chain monounsaturated fatty acids or di or triglycerides are available in naturally occurring oils ("source oils") although generally in small amounts. 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). Generally 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. However, 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. Although 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.

[0053] 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. 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. As should be apparent to one skilled in the art, the cooling-distillation process can be repeated until the selective short-chain monounsaturated fatty acid (and/or corresponding alcohol, dϊglyceride, triglyceride and/or salt) is obtained in concentrated amounts. Alternatively 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. 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.

[0054] By refining the SSCMO containing (source) oil, 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. Similarly, 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.

[0055] So, for example, in one embodiment 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. In addition, 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. In a similar manner, 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.

10057] 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.

[0058] When 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. So, for example, when algae oils are 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.

[0059] 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, CO₂, 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.

[0060] The production of algae such as in algae farms is well known. For example, in one embodiment 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.

[0061] Many other production methods or systems can also be utilized and the same are well known to the literature and to the art. See, for example U.S. 7,351,558, the entire disclosure of which is incorporated herein by reference.

[00621 Biologists have categorized microalgae in a variety of classes, mainly distinguished by their pigmentation, life cycle and basic cellular structure. Perhaps the most important types of algae with respect to abundance are as follows:

[0063] The 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.

[0064] 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.

[0065] 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.

[0066] 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.

[00671 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

[0068} Various unicellular strains of Blue-Green algae have been found to contain high amounts of C16:ln-7 (that is hexadeca-9-enoic fatty acid). The same are set forth in the article "Fatty Acid Composition of Unicellular Strains of Blue-Green Algae, Kenyon, Journal of Bacteriology, Feb. 1972, p. 827-834. Such strains can be grown in 1,400 ml of BGIl medium in a Fernbach flask with stirring at 33°C, as described there. Strain 6304 was grown in 75 ml of Kratz and Meyers medium at 30⁰C. The atmosphere was 0.5% CO₂, balance was nitrogen, and the fluorescent light intensity was about 100 foot candles. Some major fatty acids of rod-shaped unicellular blue-green algae: genus Synechococcus (strains containing monounsaturated fatty acids) are set forth in the Table 2 of the Kenyon article, which is reproduced below:

Table 2

Major fatty acids of rod-shaped unicellular blue-green algae: enus S nechococcus strains containin monounsaturated fatt acids

Values in all tables given as percentage of total fatty acids as determined by gas-liquid chromatography.

Defined in Stanier et al. c As described in Table 1 d Content of 18-carbon polyunsaturated fatty acids as a percentage by weight of the total C14, and C18 acids identified in each strain. e Not detected under conditions employed. * Trace, less than 1% of total. g Van Baalen's medium with 10 times the Ca²⁺ content.

[0069] As apparent from Table 2, high amounts of SSCMO monounsaturated fatty acid components are naturally produced, especially by strains 6307, 6603, 6708, 6709, 6301, 6311, and 6312. Cl 8:1 fatty acids are also produced. However, high amounts of undesirable saturated fatty acid components are also produced and thus these various strains of algae oil can be refined to reduce the total amount of the saturated fatty acid components to generally less than about 20 parts, desirably less than about 15 parts and preferably less than about 5 parts by volume based upon the total volume all of the fatty acid components in the composition.

[0070] Some coccoid unicellular blue-green algae strains: such as genera Aphanocapsa, Gloeocapsa, Microcystis, Chlorogloea that give fair amounts of C16:ln-7, etc., are listed in Table 3. Table 3

Major fatty acids of coccoid unicellular blue-green algae:

[0071] As apparent from Table 2, suitable amounts of SSCMO monounsaturated fatty acid components are naturally produced by algae. However, the first six examples yield high amounts of polyunsaturated fatty acid components and the same are desirably reduced by refining. Generally in all of the examples, 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.

10072] Of the above-algae strains set forth in Table 3, desired algae oils are numbers 6308, 6701, 6711, 6807, 6808, 66804, 6501, and 6712. 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. [0073] Other 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.

Concentrates

[0074] It is often desirable to store, transport and/or deliver the SSCMO component (whether in the form of a concentrated, refined source oil or in the form of an unrefined source oil) in a liquid carrier oil thereby forming a concentrated food oil additive that can be shipped to an end use site thereby saving on delivery and shipping expense. Subsequently, the food oil additive 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.

[0075] Thus, 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. For example, the carrier oil can be a fish oil or chicken fat, etc., whereas a cooking oil can be olive oil, canola oil, palm oil, or coconut oil, etc. Alternatively, the carrier oil can also be a vegetable oil such as olive oil, canola oil, palm oil, or coconut oil, etc. When the carrier oil is concentrated, 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. Embodiments in which 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.

Cooking Oil Blends Containing the SSCMO

[0076] 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. Examples of such 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 safϊlower, soybean, sunflower, and high oleic sunflower. Examples of 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.

[0077] It is to be understood that 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.)

[0078] 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). Thus, 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.

[0079] Thus, embodiments are contemplated in which the concentration of the SSCMO in the cooking oil blend of this invention (regardless of source) 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. As further discussed below, it has been found in accordance with this invention that including this SSCMO component in the cooking oil blend at these concentration levels can achieve a significant improvement in the useful life of the blend relative to the unmodified base oil when used in a typical commercial application such as occurs, for example, when French fries (pommes frites) are fried in a fast food restaurant, Le., applications in which multiple food items are successively fried in a batch of vegetable oil until the useful life of the batch runs out after which the original batch is replaced with a fresh batch of the oil. For example, it has been found possible to increase the useful life of the cooking oil used by as much as about 15%, as measured by the time the cooking oil can be used before needing to be replaced by a fresh batch. 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.

[0080] Thus, 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.

[0081] That an increase in the extended cooking life would be obtained was unexpected because one would expect that the addition of the low melting point of a SSCMO to the cooking oil upon heating would distill off more quickly, and that the polyunsaturated components of the cooking oil would polymerize and thus shorten the life of the cooking oil. That the oil blend would have extended high heat stability was also unexpected because heat causes the polyunsaturated components to break down and advance rancidity by polymerization. It was also unexpected that the blend would have extended taste life because heat causes rancidity which of course affects taste. That various foods would have a preference for up-take of the selective short-chain monounsaturated oil was also unexpected because up-take would be expected to be uniform and show no preference between saturated, monounsaturated, or polyunsaturated fatty acids. Moreover, foods cooked in the cooking oils of the present invention had a better cooking finish, that is they were more crispy and contained a brown appealing finish and had improved texture and taste.

[0082) 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. Generally 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.

[0083J More specifically, when tested in a manner as set forth in Example 1, 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%. With respect to the stability of the cooking oil at elevated temperatures, when tested in a manner as set forth in Example 1, 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%. With regard to retention of cooking oil taste when tested in a manner as set forth in Example 3, 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. With regard to the food take-up test, when tested in a manner as set forth in Example 4, 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.

[0084] The following examples set forth data with respect to these improved properties. It is to be understood that the examples and data is representative and that the specification as a whole is not limited thereto.

EXAMPLE l

Cooking Life Extension

[0085] 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 355⁰F 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. In contrast, 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. Thus, 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%.

EXAMPLE 2

Stability of Cooking Oil at Elevated Temperatures

[0086] As apparent from Example 1, the SSCMO cooking oil blends of the present invention had good high temperature stability for extended periods of time. EXAMPLE 3

Longer Retention of Cooking Oil Taste

[0087] 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.

EXAMPLE 4

Food Take-up Test

[0088] 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. Table 4

10089] As apparent from Table 4, when the amount by volume of the selective short-chain monounsaturated fatty acid, C16:ln-7, etc., of the present invention was 13.5%, the amount of this fraction for the chicken test went from 13.5% volume down to 6.7% by volume after 9 days. A decrease of 6.8% by volume or a take-up by the chicken of 50% by volume of the original C16:ln-7, etc., fatty acid. It is also apparent from Table 4, that the take-up amounts of all the remaining 16 oil fractions was essentially the same as in the initial oil with the exception of saturated C16 saturated fatty acids, C 18-2 polyunsaturated fatty acids, and Omega-6 fatty acids wherein the amount in the cooking oil actually increased. This was a result of the oil actually absorbing these undesirable fats from the chicken. With regard to the fish test, the original volume went from 13.5% down to 7.7% by volume or a decrease of 5.8% by volume. This corresponds to a take-up amount of 43% by volume of the original C16:ln-7, etc., fatty acid by the fish. Again, all remaining components were essentially the same with the exception of Cl 6 saturated fatty acids, Cl 8-2 polyunsaturated acids, and Omega-6 fatty acids which were absorbed by the cooking oil from the fish. Thus, the selective short-chain monounsaturated oils of the present invention are selectively absorbed by various food products and thus the monounsaturated fat ratio thereof to other fats, Le., saturated and polyunsaturated was increased. 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.

[0090] While it will be apparent that the preferred embodiments of the invention have been disclosed, it will be appreciated that the invention is susceptible to modification, variation, and change without departing from the intended scope or fair meaning of the subjoined claims.

Claims

1. An edible oil comprising a blend of a vegetable oil and an algae oil, wherein the algae oil comprises

(a) at least about 20 vol.%, based on the total volume of fatty acid components in the algae oil, of a selective short-chain monounsaturated oil (SSCMO) comprising one or more selected short chain monounsaturated fatty acids (SSCMUFA) selected from C16:ln-7, C16:ln-6, C16:ln-5, C16:ln-4, C16:ln-3, C14:ln-5, C14:ln-4, C14:ln-3, C12:ln-3, or any combination thereof, or an alcohol, diglyceride, triglyceride or salt of said SCMUFA, or mixtures thereof,

(b) no more than about 20 vol.% saturated fatty acids, and

(c) no more than about 20 vol.% polyunsaturated fatty acids.

2. The edible oil of claim 1, wherein the blend comprises at least 4 vol. % of the SSCMO, based on the total volume of fatty acid components in the blend.

3. The edible oil of claim 2, wherein the algae oil is refined.

4. The edible oil of claim 2, wherein the algae oil contains at least about 50 vol.% of SSCMO.

5. The edible oil of claim 2, wherein the vegetable oil is derived from one or more of coconut, palm kernel, coco butter, com, cottonseed, olive, peanut, rapeseed, canola, safflower, high oleic safflower, soybean , sunflower and high oleic sunflower, vegetable

6. The edible oil of claim 5, wherein the vegetable oil is derived from one or more of corn oil, olive oil, canola oil, sunflower oil, or mixtures thereof.

7. The edible oil of claim 1, wherein the edible oil is a concentrate containing at least about 20 vol. % SSCMO, based on the total volume of fatty acid components in the concentrate.

8. The edible oil of claim 7, wherein the concentrate contains at least about 50 vol. % SSCMO.

9. 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 monounsaturated oil (SSCMO) comprising one or more selected short chain monounsaturated fatty acids (SSCMUFA) selected from C16:ln-7_} C16:ln-6, C16:ln-5, C16:ln-4, C16:ln-3, C14:ln-5, C14:ln-4, C14:ln-3, C12:ln-3, or any combination thereof, or an alcohol, diglyceride, triglyceride or salt of said SSCMUFA, or mixtures thereof,

(b) no more than about 20 vol.% saturated fatty acids, and

(c) no more than about 20 vol.% polyunsaturated fatty acids.

10. The algae oil of claim 9, wherein the algae oil contains at least about 50 vol.% SSCMO.

11. An extended-life cooking oil comprising a blend of

A) a selective short-chain monounsaturated oil (SSCMO) comprising one or more selected short chain monounsaturated fatty acids (SSCMUFA) selected from C16:ln-7, C16:ln-6, C16:ln-5, C16:ln-4, C16:ln-3, C14:ln-5, C14:ln-4, C14:ln-3, C12:ln-3, or any combination thereof, or an alcohol, diglyceride, triglyceride or salt of said SSCMUFA, or mixtures thereof; and

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; wherein the total amount of A) in the blend is sufficient to extend the useful life of said 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).

12. The cooking oil blend of claim 11, wherein the cooking oil is corn oil. cottonseed oil, olive oil, peanut oil, rapeseed oil, canola oil, safflower oil, high oleic safflower oil, soybean oil, sunflower oil, and high oleic sunflower oil, or any combination thereof.

13- The cooking oil blend of claim 12, wherein the cooking oil further contains a carrier oil containing less than 4 vol. % SSCMO, based on the total volume of fatty acid components in the carrier oil, the carrier oil being independently selected from corn oil, cottonseed oil, olive oil, peanut oil, rapeseed oil, canola oil, safflower oil, high oleic safflower oil, soybean oil, sunflower oil, and high oleic sunflower oil, or any combination thereof.

14. The cooking oil blend of claim 11, wherein the cooking oil blend contains at least about 4 vol. % SSCMO, based on the total volume of fatty acid components in the blend.

15. A concentrate comprising a blend of

(A) a source oil, the source oil being unrefined or refined, or a mixture of unrefined and refined source oils, the source oil comprising

(a) at least about 40 vol.%, based on the total volume of fatty acid components in the source oil, of a selective short-chain monounsaturated oil (SSCMO) comprising one or more selected short chain monounsaturated fatty acids (SSCMUFA) selected from C16:ln- 7, C16:ln-6, C16:ln-5, C16:ln-4, C16:ln-3, C14:ln-5, C14:ln-4, C14:ln-3, C12:ln-3, or any combination thereof, or an alcohol, diglyceride, triglyceride or salt of said SSCMUFA, or mixtures thereof,

(b) no more than about 20 vol.% saturated fatty acids, and (c) no more than about 20 vol.% polyunsaturated fatty acids, and (B) a carrier oil, the carrier oil containing less than 4 vol.% SSCMO, based on the total volume of fatty acid components in the carrier oil, wherein the concentrate comprises at least about 20 vol.% SSCMO, based on the total volume of fatty acid components in the concentrate.

16. The concentrate of claim 15, wherein the concentrate contains at least 50 vol.% carrier oil, based on the volume of the concentrate as a whole.

17. The concentrate of claim 15, wherein the source oil is refined.

18. In a method for frying foods in which multiple food items are successively fried in vegetable oil, wherein the food items are Med in a first batch of vegetable oil until the useful life of the first batch expires after which the first batch is replaced with a second batch of vegetable oil, a process for extending the useful life of the vegetable oil in the first batch comprising selecting as the vegetable oil used in the first batch a vegetable oil blended to contain a sufficient amount of a selective short-chain monounsaturated oil (SSCMO) to increase the useful life of the first batch, wherein the SSCMO is

(a) a selective short-chain monounsaturated fatty acid (SSCMUFA) selected from C16:ln-7, C16:ln-6, C16:ln-5, C16:ln-4, C16:ln-3, C14:ln-5, C14:ln-4, C14:ln-3, C12:ln-3, or combinations thereof,

(b) a fatty derivative of (a) wherein the derivative is selected from an alcohol, diglyceride, triglyceride or salt of (a), or mixtures thereof, or

(c) mixtures of (a) and (b).

19. The process of claim 18, wherein the vegetable oil is blended to contain at least about 4 vol.% SSCMO, based on the total volume of fatty acid components in the vegetable oil blend.

20. The process of claim 19, wherein the vegetable oil is blended to contain at about 4 vol.% to about 15 vol.% SSCMO.

21. The process of claim 20, wherein the vegetable oil is blended to contain at about 6 vol.% to about 14 vol.% SSCMO.

22. The process of claim 18, wherein the vegetable oil is blended to contain a sufficient amount of SSCMO to increase the useful life of the vegetable oil by at least about 15%.

23. The process of claim 18, wherein frying is accomplished at about 355° F (180° C), and further wherein the vegetable oil is blended to contain a sufficient amount of SSCMO to increase the useful life of the vegetable oil by at least about 20%.

24. The process of claim 18, wherein the oil is derived from one or more of coconut, palm kernel, coco butter, corn, cottonseed, olive, peanut, rapeseed, canola, safflower, high oleic safflower, soybean , sunflower and high oleic sunflower.

25. The process of claim 24, wherein the vegetable oil is derived from one or more of com oil, olive oil, canola oil, sunflower oil, or mixtures thereof.

26. The process of claim 24, wherein the SSCMO is derived from aquatic plant life.

27. The process of claim 26, wherein the SSCMO is derived from algae.

28. The process of claim 24, wherein the food items being fried are uncooked French fried potatoes (pommes frites).

29. In a method for frying foods in which multiple food items are successively fried in a base cooking oil containing less than 4 vol.%, based on the total volume of fatty acid components in the base cooking oil, of a selective short- chain monounsaturated oil (SSCMO), the SSCMO comprising

(a) a selective short-chain monounsaturated fatty acid selected from C16:ln-7, C16:ln-6, C16:ln-5, C16:ln-4, C16:ln-3, C14:ln-5, C14:ln-4, C14:ln-3, C12:ln-3, or combinations thereof,

(b) a fatty derivative of (a) wherein the derivative is selected from an alcohol, diglyceride, triglyceride or salt of (a), or mixtures thereof, or

(c) mixtures of (a) and (b), wherein the foods are fried in a first batch of the cooking oil until the useful life of the first batch expires after which the first batch is replaced with a second batch of the cooking oil, a process for extending the useful life of the base cooking oil in the first batch comprising selecting as the cooking oil used in the first batch a modified cooking oil blended to contain a sufficient amount of SSCMO to increase the useful life of the first batch.

30. The process of claim 29, wherein the cooking oil is a vegetable oil, a seed oil, a nut oil, a fish oil, an animal fat, or mixture thereof.

31. The process of claim 29, wherein the cooking oil is a vegetable oil, a seed oil, a nut oil, or mixtures thereof.

32. The process of claim 29, wherein the SSCMO is derived from aquatic plant life.

33. The process of claim 32, wherein the SSCMO is derived from algae.

34. The process of claim 29, wherein the vegetable oil is blended to contain a sufficient amount of SSCMO to increase the useful life of the cooking oil by at least about 15%.

35. The process of claim 29, wherein the food items being fried are uncooked French fried potatoes (pommes frites), and further wherein the cooking oil is a vegetable oil.

36. A process for cooking French fried potatoes (pommes frites) in which multiple batches of uncooked French fried potatoes are successively fried in a vegetable oil batch until the useful life of the vegetable oil batch expires, wherein the vegetable oil batch is modified to contain at least about 4 vol.%, based on the total volume of fatty acid components in the vegetable oil batch, of a Cn-C^ 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.

37. The process of claim 36, wherein the

methyl-terminated monounsaturated carboxylic acid or derivative is a fatty acid, a fatty acid alcohol, a fatty acid salt, a fatty acid diglyceride ester, a fatty acid triglyceride ester, or mixture thereof.

38. A composition for preparing French fried potatoes (pommes frites) comprising

(a) 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 C₁₂-CiO 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

(b) potatoes.

39. The composition of claim 38, wherein the C₁₂-C₁₆ memyl4erminated monounsaturated carboxylic acid or derivative is a fatty acid, a fatty acid alcohol, a fatty acid salt, a fatty acid diglyceride ester, a fatty acid triglyceride ester, or mixture thereof.

40. The composition of claim 39, wherein the modified vegetable oil is heated hot enough to fry the potatoes.

41. A composition for preparing a fried foodstuff comprising (a) a modified base oil, the base oil

(i) being selected from a vegetable oil, seed oil, nut oil, fish oil, animal fat, aquatic plant oil, or mixtures thereof, which contains less than 4 vol.%, based on the total volume of fatty acid components in the base oil, of a C₁₂-C_1S 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,

(ii) the base vegetable oil having been modified by blending or refining or both to contain at least about 4 vol.% of this Ci₂-C_1G methyl-terminated monounsaturated carboxylic acid or derivative oil, and (iii) being heated hot enough to fry the foodstuff and (b) a foodstuff comprising at least one of a vegetable, a fruit, a bread or breaded product, a meat and a cheese.

42. The composition of claim 41, wherein the C₁₂-Ci_O methyl-terminated monounsaturated carboxylic acid or derivative is a fatty acid, a fatty acid alcohol, a fatty acid salt, a fatty acid diglyceride ester, a fatty acid triglyceride ester, or mixture thereof.

43. A composition for preparing a fried foodstuff comprising a modified base oil, the base oil

(i) being selected from a vegetable oil, seed oil, nut oil, fish oil, animal fat, aquatic plant oil, or mixtures thereof, which contains less than 4 vol.%, based on the total volume of fatty acid components in the base oil, of a Ci2-Ci6 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.,

(ii) having been modified by blending or refining or both to contain at least about 4 vol,% of ibis C^-C₁O methyl-terminated monounsaturated carboxylic acid or derivative oil, and

(ϋi) being heated hot enough to fry the foodstuff.

44. The edible oil of claim 1, wherein the vegetable oil is non- hydrogenated.

45. The cooking oil blend of claim 11, wherein the cooking oil is non- hydrogenated.

46. The concentrate of claim 15, wherein the carrier oil is non- hydrogenated.

47. The method of claim 18, wherein the vegetable oil is non- hydrogenated.

48. The method of claim 29, wherein the base cooking oil is non- hydrogenated.

49. The process of claim 36, wherein the vegetable oil is non- hydrogenated.

50. The composition of claim 38, wherein the modified vegetable oil is a non-hydrogenated modified vegetable oil.

51. The composition oil of claim 41, wherein the base oil is non- hydrogenated.

52. The composition of claim 43, wherein the base oil is non- hydrogenated.