VEGETABLE-OIL-BASED FAT SYSTEMS COMPRISING LONG-CHAIN POLYUNSATURATED FATTY ACIDS AND USES THEREOF

TECHNICAL FIELD

[0001 ] The present disclosure relates generally to vegetable-oil-based fat systems including long-chain polyunsaturated fatty acids and uses of the same.

BACKGROUND

[0002] Consumers are paying increasing attention to not only the total fat content in food products, but also the nature of those fats. In general, foods low in saturated fats and trans-fats are viewed as healthier. Consumers also perceive some health benefits in increasing the levels of omega-3 fatty acids in one's diet.

[0003] Omega-3 fatty acids, also referred to as n-3 fatty acids, are polyunsaturated fatty acids having a carbon-carbon double bond in the third position from the end of the carbon chain. From a nutritional standpoint, the most important omega-3 fatty acids are probably a- linolenic acid ("ALA"), eicosapentaenoic acid ("EPA"), and docosahexaenoic acid ("DHA"). ALA is an 18-carbon fatty acid moiety having three carbon-carbon double bonds (commonly referred to as CI 8:3 in shorthand notation), one of which is at the n-3 position. EPA is a 20- carbon fatty acid moiety having 5 carbon-carbon double bonds ("C20:5") and DHA is a 22- carbon fatty acid moiety having 6 carbon-carbon double bonds ("C22:6").

[0004] Unfortunately, ALA, EPA, and DHA are all polyunsaturated fats that tend to oxidize, and thus rancidify, fairly readily. EPA (with 5 carbon-carbon double bonds) is significantly more prone to oxidation than ALA; DHA (with 6 carbon-carbon double bonds) is even more prone to oxidation than EPA. As a consequence, increasing the omega-3 fatty acid content tends to reduce the shelf life of many food products. These problems become particularly acute with fat systems including significant amounts of EPA and DHA.

SUMMARY

[0005] In one aspect, provided is a vegetable-oil-based fat system including long-chain polyunsaturated fatty acids, where the polyunsaturated fatty acids are selected from the group consisting of EPA and DHA. In some embodiments, the EPA and/or DHA are derived from a canola plant source. [0006] In another aspect, provided are methods for making vegetable-oil-based fat systems of the present disclosure.

[0007] In another aspect, provided are food products including the vegetable-oil-based fat systems.

DETAILED DESCRIPTION

[0008] Disclosed herein are vegetable-oil-based fat systems comprising canola oil including long-chain polyunsaturated fatty acids, where the polyunsaturated fatty acids are selected from the group consisting of EPA and DHA.

Vegetable Oil

[0009] As used herein, the term "vascular plant" refers to a plant having the vascular tissues xylem and phloem (e.g., palm plant, canola plant, cotton plant).

[0010] As used herein, the term "vegetable-oil-based fat system" means a solid fat composition including fats and/or oils derived entirely from a vascular plant source or more than one vascular plant source, such as, for example, a mixture of a palm oil, palm stearin, and a canola oil, or a mixture of a fully hydrogenated cotton oil and a canola oil. A vegetable-oil-based fat system of the present disclosure does not include fats and/or oils such as, for example, fats and/or oils derived from an animal source (e.g., butter, lard), a marine animal source (e.g., menhaden, anchovy), or a non- vascular plant source (e.g., an algae).

[001 i] As used herein, the term "canola oil" means an oil derived from a Brassica napus plant which produces seed that yields oil having less than 2% erucic acid and meal that contains no more than 30 micromoles of the following glucosinolates per gram of air-dry, oil- free solid: 3-butenyl glucosinolate, 4-pentenyl glucosinolate, 2-hydroxy-3 butenyl glucosinolate, and 2-hydroxy-4-pentenyl glucosinolate, i.e., a canola plant. The canola oil may include one or more omega-3 fatty acids, such as, for example, a-linolenic acid

("ALA"), docosahexaenoic acid ("DHA"), eicosapentaenoic acid ("EPA"), and stearidonic acid ("SDA"). In some embodiments, the DHA and EPA in the canola oil are produced by a vascular plant. In some embodiments, the vascular plant is selected from the plant family Brassicaceae. In some embodiments, the vascular plant is a canola plant.

[0012] In some aspects, vegetable-oil-based fat systems of the present disclosure may comprise a canola oil including long-chain polyunsaturated fatty acids, where the polyunsaturated fatty acids are selected from the group consisting of EPA and DHA and where the EPA and/or DHA are derived from a vascular plant source.

[0013] In some embodiments, the canola oil may include at least 0.05 wt.%, at least 0.1 wt.%, at least 0.2 wt.%, at least 0.3 wt.%, at least 0.4 wt.%, at least 0. 5 wt.%, at least 0.6 wt.%, at least 0.7 wt.%, at least 0.8 wt.%, at least 0.9 wt.%, at least 1 wt.%, at least 1.5 wt.%, at least 2 wt.%, at least 2.5 wt.%, at least 3 wt.%, at least 3.5 wt.%, at least 4 wt.%, at least 4.5 wt.%, at least 5 wt.%, at least 5.5 wt.%, at least 6 wt.%, at least 6.5 wt.%, at least 7 wt.%, at least 7.5 wt.%, at least 8 wt.%, at least 8.5 wt.%, at least 9 wt.%, at least 9.5 wt.%, at least 10 wt.%, at least 12 wt.%, at least 14 wt.%, at least 16 wt.%, at least 18 wt.%, at least 20 wt.%, at least 22 wt.%, at least 24 wt.%, at least 26 wt.%, or at least 28 wt.% EPA.

[0014] In some embodiments, the canola oil may include at least 0.05 wt.%, at least 0.1 wt.%, at least 0.2 wt.%, at least 0.3 wt.%, at least 0.4 wt.%, at least 0. 5 wt.%, at least 0.6 wt.%, at least 0.7 wt.%, at least 0.8 wt.%, at least 0.9 wt.%, at least 1 wt.%, at least 1.5 wt.%, at least 2 wt.%, at least 2.5 wt.%, at least 3 wt.%, at least 3.5 wt.%, at least 4 wt.%, at least 4.5 wt.%, at least 5 wt.%, at least 5.5 wt.%, at least 6 wt.%, at least 6.5 wt.%, at least 7 wt.%, at least 7.5 wt.%, at least 8 wt.%, at least 8.5 wt.%, at least 9 wt.%, at least 9.5 wt.%, at least 10 wt.%, at least 12 wt.%, at least 14 wt.%, at least 16 wt.%, at least 18 wt.%, at least 20 wt.%, at least 22 wt.%, at least 24 wt.%, at least 26 wt.%, or at least 28 wt.% DHA.

[0015] In some embodiments, the canola oil may include at least 0.05 wt.%, at least 0.1 wt.%, at least 0.2 wt.%, at least 0.3 wt.%, at least 0.4 wt.%, at least 0. 5 wt.%, at least 0.6 wt.%, at least 0.7 wt.%, at least 0.8 wt.%, at least 0.9 wt.%, at least 1 wt.%, at least 1.5 wt.%, at least 2 wt.%, at least 2.5 wt.%, at least 3 wt.%, at least 3.5 wt.%, at least 4 wt.%, at least 4.5 wt.%, at least 5 wt.%, at least 5.5 wt.%, at least 6 wt.%, at least 6.5 wt.%, at least 7 wt.%, at least 7.5 wt.%, at least 8 wt.%, at least 8.5 wt.%, at least 9 wt.%, at least 9.5 wt.%, at least 10 wt.%, at least 12 wt.%, at least 14 wt.%, at least 16 wt.%, at least 18 wt.%, at least 20 wt.%, at least 22 wt.%, at least 24 wt.%, at least 26 wt.%, or at least 28 wt.% combined EPA and DHA.

[0016] In some embodiments, the canola oil may be a refined oil. As used herein, the term "refined oil" refers to a vegetable oil which has undergone a refining process. Refining is a process in which unwanted constituents are removed from an oil. Oils can be refined to varying degrees, and it is the desired quality of the refined oil which determines the degree of refining. Additionally, depending upon the properties of the oil desired, different processing steps can be included. Processes of refining oils are well known in the art; an exemplary description of a refining process is provided in Perkins et al., Deep Frying: Chemistry, Nutrition, and Practical Applications, pp. 12-24, AOCS Press, 1996.

Vegetable-oil-based Fat System

[0017] Vegetable-oil-based fat systems of the present disclosure may include canola oil including long-chain polyunsaturated fatty acids, where the polyunsaturated fatty acids are selected from the group consisting of EPA and DHA, as described above, and at least one of palm oil, palm stearin, and fully-hydrogenated cotton seed oil.

[0018] In some embodiments, the vegetable-oil-based fat system of the present disclosure may include at least 30 wt.%, at least 40 wt.%, at least 50 wt.%, at least 60 wt.%, at least 70 wt.%, or at least 80 wt.% canola oil including long-chain polyunsaturated fatty acids, where the polyunsaturated fatty acids are selected from the group consisting of EPA and DHA. In some embodiments, the EPA and/or DHA are derived from a canola plant source.

[0019] Palm oil useful in embodiments of the present disclosure is commercially available as product P-100 from Cargill, Incorporated, Wayzata, MN, USA.

[0020] In some embodiments, the vegetable-oil-based fat system of the present disclosure may include at least 15 wt.%, at least 20 wt.%, at least 25 wt.%, at least 30 wt.%, at least 35 wt.%, or at least 40 wt.% palm oil.

Palm stearin useful in embodiments of the present disclosure is commercially available as product P-130 from Cargill, Incorporated, Wayzata, MN, USA.

[0021 ] In some embodiments, the vegetable-oil-based fat system of the present disclosure may include at least 15 wt.%, at least 20 wt.%, at least 25 wt.%, at least 30 wt.%, at least 35 wt.%, at least 40 wt.%, at least 45 wt.%, at least 50 wt.%, or at least 55 wt.% palm stearin.

Fully-hydrogenated cotton seed oil useful in embodiments of the present disclosure is commercially available as product CGFLKHYDCOTKPZT from Cargill, Incorporated, Wayzata, MN, USA.

[0022] In some embodiments, the vegetable-oil-based fat system of the present disclosure may include at least 30 wt.%, at least 40 wt.%, at least 50 wt.%, at least 60 wt.%, at least 70 wt.%, or at least 15 wt.% fully-hydrogenated cotton seed oil. [0023] In some embodiments, the vegetable-oil-based fat system of the present disclosure may include about 34 wt.% of a canola oil including long-chain polyunsaturated fatty acids, where the polyunsaturated fatty acids are selected from the group consisting of EPA and DHA, about 42 wt.% palm oil, and about 23 wt.% palm stearin. In some embodiments, the EPA and/or DHA in the canola oil are derived from a canola plant source.

[0024] In some embodiments, the vegetable-oil-based fat system of the present disclosure may include about 45 wt.% of a canola oil including long-chain polyunsaturated fatty acids, where the polyunsaturated fatty acids are selected from the group consisting of EPA and DHA and about 55 wt.% palm stearin. In some embodiments, the EPA and/or DHA in the canola oil are derived from a canola plant source.

[0025] In some embodiments, the vegetable-oil-based fat system of the present disclosure may include about 83 wt.% of a canola oil including long-chain polyunsaturated fatty acids, where the polyunsaturated fatty acids are selected from the group consisting of EPA and DHA and about 17 wt.% fully hydrogenated cotton seed oil. In some embodiments, the EPA and/or DHA in the canola oil are derived from a canola plant source.

Preparation of a Vegetable-oil-based Fat System

[0026] Vegetable-oil-based fat systems of the present disclosure may be prepared by methods known to those or ordinary skill in the relevant arts. Preparation of fat systems are disclosed, for example, in U.S. Patent Pub. 2015/0064329.

Food Products

[0027] The vegetable-oil-based fat systems described herein can be incorporated into food products such as, for example, doughs or mixes to make food products such as donuts pizzas, crusts (e.g., pie crusts), cookies, biscuits, pastries (e.g., toaster pastries), bread, coffee creamers, the cream in a cream-filled food product, a frosting, or an icing.

[0028] Nutrition Facts label serving sizes are based on the amount of food customarily eaten at one time (called the "reference amount") as reported from nationwide food consumption surveys. (USDA & DHHS, 2000, Nutrition and Your Health: Dietary

Guidelines for Americans, Fifth Ed., Home and Garden Bulletin No. 23). Serving sizes are based on reference amounts in one of three ways (FDA Center for Food Safety and Applied Nutrition, 2000, Food Labeling and Nutrition). For bulk products, such as cereals and flour, the Nutrition Facts labels use common household terms such as cup, tablespoon, teaspoon, and fluid once at a quantity that is closest to the reference amount for that item. For products that are usually divided from consumption, such as cake or pizza, the serving size is a fractional amount of the product (e.g., " 1/4 pizza"). Products that come in defined, discrete units— such as eggs and sliced products-are normally listed as the number of whole units that most closely approximates the reference amount. For example, cookies have a reference amount of 30 g. Thus, the serving size on a package of cookies weighing about 30 g each would be " 1 cookie."

[0029] Food products can be evaluated using mechanized procedures such as DIPIX instrumentation (Ottawa, Canada). DIPIX technology provides inspection systems for food products. DIPIX Inspection Systems can inspect the 3-dimensional features such as thickness, height, and end-to-end or center-to-end slope, the 2-dimensional features such as length, width, minimum diameter, maximun diameter, and ovality, and bake color features such as bake color of edges, background, and ridges and valleys. DIPIX Inspection Systems also can inspect the optical density of a food product to detect holes and/or uncooked portions of a food product.

[0030] A food product and the effect of a particular ingredient or process also can be evaluated by examining the sensory attributes of a food product. Sensory attributes include, for example, color, tenderness, amount of cracking, gumminess, chewiness, moistness, hardness, flavor quality, mouth coating, finger oiliness, and graininess. Sensory attributes of food products may be determined by a trained sensory panel. A sensory panel refers to those individuals involved in the sensory evaluation of the edible food product. Panelists are pre- screened to be able to detect the flavor differences in the particular product tested and are trained in sensory descriptions. A panel provides qualitative and quantitative scores for the sensory evaluation that are referenced against calibrated standards.

[0031] Either or both the DIPIX results and the sensory panel results can be analyzed for statistical significance. Statistical significance generally refers to a p- value of less than 0.05, e.g., a p-value of less than 0.025 or a p-value of less than 0.01, using an appropriate parametric or non-parametric measurement, e.g., a one-tailed two-sample t-test. Standard deviation may also be measured for many features. EXAMPLES

[0032] Aspects of certain embodiments in accordance with aspects of the disclosure are illustrated in the following Examples. The materials and methods described in these

Examples are illustrative and not intended to be limiting.

Experimental Procedures

[0033] Dropping Point: dropping point measurements are carried out in accordance with AOCS Standard Procedure Cd 12b-92, Reapproved 2009 using a Mettler FP90 control unit and FP83HT dropping point furnace (Mettler Instrument Corp., Hightstown, NJ, USA) or their equivalent.

Solid Fat Content Analysis ("SFC"): measurement of solid fat contents of samples is carried out in accordance with AOCS Standard Procedure Cd 16-b-93 using an Benchtop NMR MQC Analyser pulsed nuclear magnetic resonance spectrometer (Oxford Instruments, Abingdon, United Kingdom).

Materials

[0034] Canola oil including 2.15 wt% combined EPA and DHA, the EPA and DHA both produced by a canola plant("EPA-DHA Canola Oil"); palm oil P-100 from Cargill, Incorporated, Wayzata, MN, USA; palm stearin P-130 from Cargill, Incorporated, Wayzata, MN, USA; fully-hydrogenated cotton seed oil CGFLKHYDCOTKPZT from Cargill, Incorporated, Wayzata, MN, USA; and CLEAR VALLEY 65-brand canola oil ("CV65") from Cargill, Incorporated, Wayzata, MN, USA.

Example 1 : Vegetable-oil-based Fat System - Prototype 1

[0035] Vegetable-oil-based fat systems Prototype 1 and Control 1 are prepared using the ingredients in amounts as shown in Table 1. Vegetable-oil-based fats are prepared by: a) combining all ingredients to provide a mixture;

b) heating the mixture to a temperature sufficient to provide a liquid;

c) cooling the liquid to about 13 °C with stirring; and

d) allowing the cooled liquid to warm to room temperature (about 23 °C) and sit undisturbed for about 12 to about 48 hours. [0036] A dropping point test and solid fat content ("SFC") test are conducted on samples of Prototype 1 and Control 1 as set forth above. The results of the dropping point test and solid fat content determination at different temperatures are set forth in Table 1.

Table 1. Vegetable-oil-based Fat Systems and Associated Dropping Points

[0037] As shown in Table 1, Prototype 1 prepared with EPA-DHA canola oil (102 mg EPA-DHA/14 g Fat System) unexpectedly exhibited a dropping point value and SFC very similar to those of Control 1 prepared with a canola oil that did not include DHA or EPA.

Example 2: Vegetable-oil-based Fat System - Prototype 2

[0038] Vegetable-oil-based fat systems Prototype 2 and Control 2 are prepared using the ingredients in amounts as shown in Table2. Vegetable-oil-based fat systems Prototype 2 and Control 2 are prepared according to the procedure described in Example 1.

[0039] A dropping point test and solid fat content ("SFC") test are conducted on samples of Prototype 2 and Control 2 as set forth above. The results of the dropping point test and solid fat content determination at different temperatures are set forth in Table 2. Table 2. Vegetable-oil-based Fat Systems and Associated Dropping Points

[0040] As shown in Table 2, Prototype 2 prepared with EPA-DHA canola oil (135 mg EPA-DHA/14 g Fat System) unexpectedly exhibited a dropping point value and SFC very similar to those of Control 2 prepared with a canola oil that did not include DHA or EPA. Example 3: Vegetable-oil-based Fat System - Prototype 3

[0041 ] Vegetable-oil-based fat systems Prototype 3 and Control 3 are prepared using the ingredients in amounts as shown in Table 3. Vegetable-oil-based fat systems Prototype 3 and Control 3 are prepared according to the procedure described in Example 1.

[0042] A dropping point test and solid fat content ("SFC") test are conducted on samples of Prototype 3 and Control 3 as set forth above. The results of the dropping point test and solid fat content determination at different temperatures are set forth in Table 1.

Table 3. Vegetable-oil-based Fat Systems and Associated Dropping Points

SFC % (70° F) 15.8 15.55

SFC % (80° F) 14.85 14.55

SFC % (92° F) 13.1 12.85

SFC % (104° F) 10.55 10

[0043] As shown in Table 3, Prototype 3 prepared with EPA-DHA canola oil (250 mg

EPA-DHA/14 g Fat System) unexpectedly exhibited a dropping point value and SFC very similar to those of Control 3 prepared with a canola oil that did not include DHA or EPA.

Example 4. Sugar Cookies Including Vegetable-oil-based Fat Systems

[0044] The recipe shown in Table 4 is used to evaluate the prototype vegetable-oil- based fat systems in sugar cookies. The control sugar cookies included a Control Formula vegetable-oil-based fat systems in the dough instead of a Prototype vegetable-oil-based fat system.

Table 4. Sugar Cookie Recipe

[0045] The sugar, vegetable-oil-based fat system, salt, sodium bicarbonate and vanilla are mixed in a KITCHEN AID. 5 quart mixer on low speed (1) for 3 min. The eggs are added and mixed on low speed for 3 min. The milk is added and mixed on low speed for 1 min. The flours are sifted and added to the mixture. The mixture is mixed on low speed for 1 min. The cookie dough was deposited on a sheet pan liner using an ice cream scoop. The dough is baked at 400°F. for 12 min, and the cookies were placed on a rack to cool.

[0046] The cooled cookies were visually evaluated for size and color. Cookies prepared using Prototypes 1-3 were visually comparable (e.g., in size, color, surface texture, flatness, edge appearance) to cookies prepared using Control Formula 2. Oven smell and aroma of cooled cookies prepared using Prototypes 1-3 were comparable to cookies prepared using Control Formula 2. Surprisingly, cookies prepared using Prototypes 1-3 exhibited no "fishy" or other off-aromas.