WO2014150029A1 - Method of preparing highly dispersible whole grain flour with an increased avenanthramide content - Google Patents
Method of preparing highly dispersible whole grain flour with an increased avenanthramide content Download PDFInfo
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- WO2014150029A1 WO2014150029A1 PCT/US2014/021913 US2014021913W WO2014150029A1 WO 2014150029 A1 WO2014150029 A1 WO 2014150029A1 US 2014021913 W US2014021913 W US 2014021913W WO 2014150029 A1 WO2014150029 A1 WO 2014150029A1
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- whole grain
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- oat flour
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- enzyme
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/88—Liliopsida (monocotyledons)
- A61K36/899—Poaceae or Gramineae (Grass family), e.g. bamboo, corn or sugar cane
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
- A23P10/00—Shaping or working of foodstuffs characterised by the products
- A23P10/20—Agglomerating; Granulating; Tabletting
- A23P10/22—Agglomeration or granulation with pulverisation of solid particles, e.g. in a free-falling curtain
-
- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D6/00—Other treatment of flour or dough before baking, e.g. cooling, irradiating, heating
-
- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D6/00—Other treatment of flour or dough before baking, e.g. cooling, irradiating, heating
- A21D6/003—Heat treatment
-
- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D6/00—Other treatment of flour or dough before baking, e.g. cooling, irradiating, heating
- A21D6/006—Agglomeration of flour
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L7/00—Cereal-derived products; Malt products; Preparation or treatment thereof
- A23L7/10—Cereal-derived products
- A23L7/104—Fermentation of farinaceous cereal or cereal material; Addition of enzymes or microorganisms
- A23L7/107—Addition or treatment with enzymes not combined with fermentation with microorganisms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L7/00—Cereal-derived products; Malt products; Preparation or treatment thereof
- A23L7/10—Cereal-derived products
- A23L7/198—Dry unshaped finely divided cereal products, not provided for in groups A23L7/117 - A23L7/196 and A23L29/00, e.g. meal, flour, powder, dried cereal creams or extracts
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L9/00—Puddings; Cream substitutes; Preparation or treatment thereof
- A23L9/10—Puddings; Dry powder puddings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
Definitions
- the present invention relates generally to a method for preparing a highly dispersible, otherwise referred to as "soluble" whole grain flour. More specifically, the present invention relates to methods of making highly dispersible oat flour with an increased avenanthramide content.
- the present invention overcomes the aforementioned problems and provides consumers with a hydrolyzed whole grain flour that maintains its whole grain structure and nutritional value, and is highly dispersible in liquid and semi-solid media, thereby having an improved mouthfeel and improved consumer acceptance.
- Avenanthramides are antioxidants uniquely found in oats. Since their first isolation in the 1980's, more than 30 congeners have been characterized and the most abundant avenanthramides in oats are 2p, 2f and 2c. These polyphenols demonstrate potent antioxidant, anti-inflammatory and anti-atherosclerotic properties, and may be beneficial to people with chronic inflammatory diseases, allergy and cardiovascular disease. Beyond the food industry, avenanthramides' benefits have also been well documented. Tranilast, an analogue of avenanthramides, has been approved for treating inflammation-related disease and the skin care product AveenoTM is based on the proven benefits of avenanthramides.
- avenanthramides In order to achieve beneficial effects on human health, avenanthramides must be ingested in a sufficient amount. In a 1999 Tufts University study, avenanthramides were confirmed to be bioavailable and remain bioactive in humans after ingestion. After 60 or 120 mg consumption, the maximum concentrations of total plasma avenanthramide were 168 and 560 nM, respectively. A more recent study performed by the University of Minnesota showed that consumption of avenanthramides at doses as low as 0.4 or 9.2 mg/day for 8 weeks increased plasma total antioxidant activity and had dose-response effects on several antioxidant and anti-inflammatory parameters. These effects are probably due to the accumulation and high concentration of avenanthramides in different tissues and organs.
- Avenanthramide content in oat grains varies based on cultivars and food processing methods. For example, heat treatment generally reduces avenanthramide 2f, 2c, and more profoundly 2p. The processing methods that increase avenanthramide content are of great importance to help people reach health benefits through regular consumption of oat products.
- Nuclear factor-kappa B NF- ⁇ is a family of eukaryotic nuclear transcription factors that regulate the transcription of DNA and are involved in the activation of genes related to inflammatory and immune responses.
- NF- ⁇ The regulation of the inflammatory response by NF- ⁇ occurs via the enhancement of the expression of genes encoding proinflammatory cytokines, such as tumor necrosis factor (TNF)-a, interleukin (IL)-6, and interleukin (IL)-l ⁇ .
- cytokines such as tumor necrosis factor (TNF)-a, interleukin (IL)-6, and interleukin (IL)-l ⁇ .
- IL interleukin
- IL interleukin
- IL interleukin
- aspects of the invention relate to soluble oat flour having an increased avenanthramide content. Additional aspects of the present invention relate to a method for preparing a hydrolyzed whole grain flour. In one aspect of the present invention, an enzyme hydrolyzes the whole grain flour while maintaining the integrity of the whole grain.
- a whole grain is finely milled and subsequently agglomerated to improve dispersibility of the grain in liquid or semisolid media.
- the grain used for agglomeration may be untreated/native, pre- gelatinized, or hydrolyzed.
- FIG. 1 illustrates the comparison of the pre-extrusion and the post-extrusion starch values of corn and whole wheat flour prepared in accordance with the present invention.
- FIG. 2 illustrates a comparison of the starch content of whole oat flour samples pre and post processing via extrusion and pre and post processing via extrusion and enzyme addition.
- Figure 3A compares the avenanthramide levels (2C, 2P, 2F and the total level of these avenanthramides) found in whole oat flour formed using the methods described herein ("SoluOats").
- Figure 3B compares the avenanthramide levels (2C, 2P, 2F and the total level of these avenanthramides) found in whole oat flour formed using the methods described herein ("SoluOats").
- Figure 4 compares the amount of avenanthramide identified in the oat flour as a result of the various processing conditions set forth in Table 2.
- Figure 5 depicts the percent change in NF- ⁇ inhibition activity among whole oat flour, the methods described herein ("SoluOats"), and a blank.
- the present invention relates to soluble oat flour having an increased level of avenanthramides over soluble oat flour prepared in accordance with prior known methods.
- the present invention relates to a method for preparing a highly dispersible whole grain flour.
- the present invention relates to a hydrolyzed whole grain flour that maintains its whole grain status throughout processing and is highly dispersible in liquid and semi-solid media.
- the whole grain may be any suitable cereal grain such as oat, wheat, corn (maize), rice, barley, rye, quinoa, sorghum, millet, triticale or combinations thereof.
- whole grain status shall mean whole grains consisting of the intact, ground, cracked or flaked caryopsis, whose principal anatomical components - the starchy endosperm, germ and bran - are present in the same relative proportions as they exist in the intact caryopsis.
- the dispersibility of the flour was measured in water observing formation of a lump and size of the lumps and formation of the lumps on the top and bottom of the water after stirring for five (5) seconds. With respect to the flour made in accordance with the instant disclosure, no lumps were present or formed after stirring the mixture for about five (5) seconds.
- the method of hydrolyzing the whole grain flour includes hydrolyzing, milling, and agglomerating the whole grain flour. More specifically, the flour is hydrolyzed using an enzyme.
- the enzyme used in accordance with the present invention allows the whole grain flour to maintain its standard of identity as whole grain.
- an enzyme that hydrolyzes the whole grain flour while maintaining the integrity of the whole grain is alpha amylase.
- the enzyme used in accordance with the present invention may be any enzyme that hydrolyzes the alpha 1-4 bonds on the amlyopectin molecule that makes up the starch portion of the whole grains.
- the enzyme may also hydrolyze the amylose molecules of the whole grain.
- Suitable enzymes include a-amylase in the range of about 0.01- 0.5%, for example about 0.1-0.2%.
- the a- amylase used may be Validase BAA 1000L having approximately 1,000,000 MWU/g (MWU - Modified Wohlgemuth Unit).
- MWU MWU - Modified Wohlgemuth Unit
- the dry whole grain flour is preconditioned by hydrating a whole grain flour starting mixture with water and steam to an overall moisture of about 30% (dw). At least one enzyme that hydrolyzes the whole grain flour while maintaining the integrity of the whole grain is then added to the mixture.
- the dry whole grain flour may be mixed with sugar, maltodextrin and/or mixed tocopherols.
- the enzyme-treated mixture is then subjected to an extrusion process to continue to break down and hydrolyze the whole grain flour and to gelatinize and cook the mixture to form a cooked hydrolyzed whole grain dough.
- the mixture resides in the extruder for a time sufficient to gelatinize and cook the starch, but not long enough to dextrinize to the point where it is no longer whole grain or otherwise modify the starch to void the whole grain aspect, generally at least 1 minute, typically, about 1 to about 1.5 minutes.
- the material is heated from an initial inlet temperature to a final exit temperature in order to provide the energy for starch gelatinization.
- the dough pressure at the exit of the cooking extruder is about 900-1000 psi.
- the dough Prior to exiting the cooking extruder, the dough is heated to about 260-300° F, for instance about 265-285° F to fully deactivate the enzyme.
- Starch gelatinization requires water and heat.
- the gelatinization temperature range for oats is 127 °F to 138 °F (53 - 59 °C). If the moisture is less than about 60% then higher temperatures are required.
- Heat may be applied through the extruder barrel wall such as with a jacket around the barrel through which a hot medium like steam, water or oil is circulated, or electric heaters imbedded in the barrel.
- a hot medium like steam, water or oil is circulated, or electric heaters imbedded in the barrel.
- the extrusion occurs at barrel temperatures between 140 °F and 350 °F, for example between 175 °F and 340 °F, more specifically about 180 °F-300 °F.
- Heat is also generated within the material by friction as it moves within the extruder by the dissipation of mechanical energy in the extruder, which is equal to the product of the viscosity and the shear rate squared for a Newtonian fluid. Shear is controlled by the design of the extruder screw(s) and the screw speed. Viscosity is a function of starch structure, temperature, moisture content, fat content and shear. The temperature of the dough increases in the extruder to approximately 212 °F and 300 °F.
- Low shear is applied to the mixture in the extruder. As the enzyme has preconditioned the starch to about 30% moisture, high shear is not required for this process. It can also increase the dough temperature excessively, which can overcook it resulting in too much cooked grain flavor. It is noted that the barrel temperature and the dough temperature may be different.
- the process balances limiting the dough temperature to avoid too much cooked grain flavor and to keep the enzyme active.
- the process is balanced such that the dough temperature rises to a sufficient temperature to deactivate the enzyme.
- Such temperatures are at least 280 °F, generally 212 °F to 300 °F.
- the temperature used to deactivate the enzyme is dependent on the time it is held at this temperature.
- a low shear extrusion process is characterized relative to high shear extrusion by high moisture and a low shear screw design versus low moisture and a high shear screw design.
- Any suitable extruder may be used including suitable single screw or twin screw extruders. Typical, but not limiting, screw speeds are 200-300 rpm. As one of ordinary skill in the art would recognize, screw speed is dependent upon the screw design.
- the resulting product may be pelletized using a forming extruder and dried.
- the process takes about 9-10 minutes from the preconditioner step through the extruder and forming extruder.
- the pellets may be finely milled to about 50-200 microns.
- One type of milling process that can be used to finely mill the pellets includes gradual reduction roller mill processing.
- the pellets may be dried to about 8 ⁇ 2% moisture prior to milling.
- the finely milled hydrolyzed grain flour may be agglomerated to about 150-700 microns. Fine milling of the pellets improves the mouthfeel of the resulting hydrolyzed oat flour and therefore improves consumer acceptance of the resulting product.
- the agglomeration step post-milling is advantageous in that it optimizes and drastically improves dispersibility and lends itself to many applications for preparing comestible products.
- the fine whole grain particles are agglomerated using a 2% sugar binder solution.
- the agglomerated hydrolyzed grain flour can be added to, and is highly dispersible in, liquid and semi-solid media such as water, milk, juice, yogurts, puddings and other drinkable snack forms.
- the agglomerated hydrolyzed grain flour made in accordance with the present invention makes it easy for consumers to effortlessly and efficiently stir the flour into the liquid or semi-solid of their choosing using common household utensils due to the rapid dispersion of the hydrolyzed grain flours into these liquids or semi-solids.
- the agglomerated hydrolyzed grain flour made in accordance with this invention may be dispersed into liquid media by simply shaking to mix the constituents.
- the agglomerated hydrolyzed oat flour made in accordance with the present invention exhibits the properties identified in Table 2 below:
- untreated/native whole grain is finely milled to a particle size of about 50-420 microns, such as about 50-200 microns. These finely milled particles are then agglomerated to about 150-1000 microns, such as about 400-700 microns.
- the finely milled native whole grain flour may be agglomerated using any methods known in the industry, including, without limitation, using a sugar binder solution.
- pre-gelatinized whole grain flour is finely milled to a particle size of about 50-420 microns, such as 50-200 microns.
- the whole grains may be pre-gelatinized or pre-treated using any commercially acceptable means, including, without limitation steam treating and boiling. These finely milled pre-gelatinized whole grain particles are then agglomerated to about 150-1000 microns, such as 400-700 microns.
- Another aspect of this invention includes finely milling one or more whole grain flours selected from the group consisting of native, pre-gelatinized and hydrolyzed whole grain flours made in accordance with this disclosure.
- the whole grain flours are finely milled to a particle size of about 50-420 microns, such as 50-200 microns.
- These finely milled pre-gelatinized whole grain particles are then agglomerated to about 150-1000 microns, such as 150-700 microns, including 400-700 microns.
- the agglomerated whole grain flours made in accordance with aspects of this invention maintain the whole grain status throughout processing. Therefore, "whole grain” health claims may be made with respect to the flour made in accordance with the present invention.
- the highly dispersible whole grain flour prepared in accordance with the present invention may be used to provide the consumer with a drinkable grain product.
- hydrolyzed oat flour prepared in accordance with the present invention may be added to water, milk, juice, yogurts, puddings, etc., to make a whole grain oat drinkable snack that is nutritious and easy to consume.
- the hydrolyzed whole grain flour is highly dispersible in liquids and semi-solids, the drinkable snack is also fast and easy to prepare.
- the native and pre- gelatinized agglomerated flours may be added to the water, milk, juice, yogurts, puddings, etc. to make a whole grain drinkable snack.
- the highly dispersible oat flour made in accordance with the processes described herein contains an increased avenanthramide level compared to unprocessed oats or native oat flour.
- native oat flour contains about 0.0002-0.03% total avenanthramides.
- Avenanthramides are polyphenols found only in oats. Avenanthramides have been shown to have significant antioxidant activity and have been linked to many beneficial health activities due to their potent antioxidant activities. In vivo testing has shown that the antioxidant capacity for avenanthramides provides health benefits such as a reduced rate of LDL oxidation thus protecting against cancers and heart disease.
- the structure of avenanthramide 2c is shown below:
- Applicants have found that the levels of the three main avenanthramides present in oat - 2c, 2p and 2f - are all increased as a result of the processes described herein.
- the total avenanthramide level (including 2c, 2p and 2f) is elevated by about 20-35% compared to native whole oat flour by the methods used to prepare the soluble oat flour described above.
- Clause 3 The highly dispersible whole grain oat flour of clause 1 or clause 2 wherein the oat flour exhibits NF- ⁇ inhibition activity wherein the NF- ⁇ inhibition activity is at least about 25% greater than native whole grain oat flour.
- Clause 8 The highly dispersible whole grain oat flour of any of clauses 4-7 wherein the starting mixture further comprises sugar and optionally maltodextrin.
- Clause 9 The highly dispersible whole grain oat flour of any of clauses 4-8 wherein the moisture content of the enzyme starting mixture in the extruder is about 28-32%.
- Clause 10 The highly dispersible whole grain oat flour of any of clauses 4-9 wherein the avenanthramide content of the flour is about 35% greater than native whole grain oat flour.
- Clause 11 The highly dispersible whole grain oat flour of any of clauses 4-10 wherein the oat flour exhibits NF- ⁇ inhibition activity wherein the NF- ⁇ inhibition activity is at least about 25% greater than native whole grain oat flour.
- Clause 13 The highly dispersible whole grain oat flour of clauses 4-12 wherein the starting mixture further comprises mixed tocopherols.
- the avenanthramide levels of the resulting soluble oat flour were measured using reverse-phase HPLC. Briefly dehulled grain was extracted, dried, and re-suspended into aliquots. Aliquots were analyzed by HPLC with a C-18 column using a diode array spectrophotometer detector with detection at 340 nm. The peaks were quantified by comparison to standard curves of authentic avenanthramides. The results of this testing are illustrated in Figure 1A and Figure IB.
- the avenanthramide content of the soluble oat flour made in accordance with the methods described herein were also found to have higher avenanthramide content than oat flour processed using solely extrusion (no enzyme.)
- Figure 3A depicts the levels of avenanthramide 2c, avenanthramide 2p, avenanthramide 2f and the total avenanthramide (2c + 2p + 2f) in samples of native whole oat flour, extruded flour and the SoluOat 100 flour made in accordance with the instant inventions.
- “SoluOat 100,” or “SoluOat 100 flour” whether singular or plural, shall mean 99.5% whole oat flour and 0.5% mixed tocopherol made in accordance with the methods set forth in the present disclosure.
- the highest level of avenanthramides 2c, 2p and 2f, and the total avenanthramide content was found in the SoluOat 100 flour.
- the native whole oat flour was found to contain about 35 ppm total avenanthramides whereas the SoluOat flour was found to contain over 40 ppm total avenanthramides resulting in a 20% increase in the level of avenanthramides in the SoluOat 100 flour compared to the native whole oat flour.
- Figure 3B a similar test was performed testing the avenanthramide content of native whole oat flour and the SoluOat 100 flour made in accordance with the instant invention.
- the native whole oat flour was found to have about 35 ppm of total avenanthramides whereas the SoluOat 100 flour contained about 45 ppm total avenanthramides.
- the SoluOat 100 flour exhibited a 35% increase in the level of total avenanthramides compared to the native whole oat flour.
- the increased avenanthramide content of the soluble oat fiber made via the embodiments described herein is surprising, since this antioxidant is a non-starch plant nutrient.
- this antioxidant is a non-starch plant nutrient.
- the enzymatic process described above is used to improve dispersibility and solubility of the flour.
- the table below identifies the avenanthramide level found in the oat flour under the different processing conditions along with the increase in avenanthramide content. All samples in the table that were extruded and hydrolyzed in accordance with the present disclosure are SoluOat 100, as defined above.
- WOF whole oat flour (unhydrolyzed); EXT: extrusion; E: enzyme; DE: deactivated enzyme; moisture; Ave: avenanthramide
- avenanthramide 2c has the highest antioxidant activity in vitro among the three major avenanthramides (2c, 2 p, 2f). With respect to in vivo activity, avenanthramide 2p has the highest bioavailability. Extrusion alone increased the total avenanthramide content slightly (3.72%), but dramatically increased avenanthramide 2p content (27.79%). Enzymatic digestion increased total and individual avenanthramide content, including that of 2c, 2p, and 2f.
- NF-KB is an immune response/inflammation trigger.
- reduced NF- ⁇ is clinically linked to reduced chronic inflammation.
- Anti-inflammatory activity was measured by NF-KB inhibitory assay.
- Human 293T cells were cultured overnight in standard medium with fetal bovine serum and antibiotics followed by a 4-hour serum free to "starve" period.
- "starved" cells are cells having a serum-free medium to eliminate the effects of fetal bovine serum and therefore the cells are more sensitive to TNF treatments.
- SoluOat 90 denotes that 90%> of SoluOat was whole oat flour ⁇ A11 samples were tested at concentration of 2 mg/mL
- Figure 5 illustrates the percent of NF- ⁇ inhibition in the samples.
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Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
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CN201480023500.5A CN105228639B (en) | 2013-03-15 | 2014-03-07 | Prepare the method with the full grain dust of polymolecularity of increased oat alkaloid |
BR112015022808A BR112015022808A8 (en) | 2013-03-15 | 2014-03-07 | Highly dispersible whole grain oatmeal with increased avenantramide content and method of preparation thereof |
RU2015144065A RU2606829C1 (en) | 2013-03-15 | 2014-03-07 | Method for producing fine whole grain flour with high content of aventramid |
AU2014237555A AU2014237555C1 (en) | 2013-03-15 | 2014-03-07 | Method of preparing highly dispersible whole grain flour with an increased avenanthramide content |
MX2015013033A MX346373B (en) | 2013-03-15 | 2014-03-07 | Method of preparing highly dispersible whole grain flour with an increased avenanthramide content. |
CA2905746A CA2905746C (en) | 2013-03-15 | 2014-03-07 | Method of preparing highly dispersible whole grain flour with an increased avenanthramide content |
EP14767672.0A EP2968432A4 (en) | 2013-03-15 | 2014-03-07 | Method of preparing highly dispersible whole grain flour with an increased avenanthramide content |
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US13/833,717 US9011947B2 (en) | 2009-06-14 | 2013-03-15 | Method of preparing highly dispersible whole grain flour with an increased avenanthramide content |
US13/833,717 | 2013-03-15 |
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US (1) | US9011947B2 (en) |
EP (1) | EP2968432A4 (en) |
CN (1) | CN105228639B (en) |
AU (1) | AU2014237555C1 (en) |
BR (1) | BR112015022808A8 (en) |
CA (1) | CA2905746C (en) |
MX (1) | MX346373B (en) |
RU (1) | RU2606829C1 (en) |
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US9504272B2 (en) | 2008-11-04 | 2016-11-29 | The Quaker Oats Company | Method of processing oats to achieve oats with an increased avenanthramide content |
US9510614B2 (en) | 2008-11-04 | 2016-12-06 | The Quaker Oats Company | Food products prepared with soluble whole grain oat flour |
US10689678B2 (en) | 2008-11-04 | 2020-06-23 | The Quaker Oats Company | Method and composition comprising hydrolyzed starch |
HUE048820T2 (en) | 2010-07-22 | 2020-09-28 | K Fee System Gmbh | Portion capsule with barcode |
WO2012128881A1 (en) | 2011-03-21 | 2012-09-27 | Pepsico, Inc. | Method for preparing high acid rtd whole grain beverages |
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TW201438593A (en) | 2014-10-16 |
CN105228639B (en) | 2019-04-02 |
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AU2014237555B2 (en) | 2016-06-09 |
US9011947B2 (en) | 2015-04-21 |
AU2014237555A1 (en) | 2015-11-05 |
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EP2968432A1 (en) | 2016-01-20 |
AU2014237555C1 (en) | 2017-06-22 |
CN105228639A (en) | 2016-01-06 |
MX2015013033A (en) | 2016-05-18 |
BR112015022808A2 (en) | 2017-07-18 |
EP2968432A4 (en) | 2016-07-27 |
CA2905746C (en) | 2016-11-08 |
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