EP3761807A1 - Flavour composition - Google Patents
Flavour compositionInfo
- Publication number
- EP3761807A1 EP3761807A1 EP19709049.1A EP19709049A EP3761807A1 EP 3761807 A1 EP3761807 A1 EP 3761807A1 EP 19709049 A EP19709049 A EP 19709049A EP 3761807 A1 EP3761807 A1 EP 3761807A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- bran
- treated
- heat
- flavour
- food product
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- 235000019634 flavors Nutrition 0.000 title claims abstract description 122
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- 239000002002 slurry Substances 0.000 claims abstract description 76
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- 239000000047 product Substances 0.000 claims description 52
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- 238000010438 heat treatment Methods 0.000 claims description 38
- 238000011282 treatment Methods 0.000 claims description 33
- 239000004615 ingredient Substances 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 claims description 23
- 235000013736 caramel Nutrition 0.000 claims description 23
- 239000000706 filtrate Substances 0.000 claims description 23
- YOMSJEATGXXYPX-UHFFFAOYSA-N 2-methoxy-4-vinylphenol Chemical compound COC1=CC(C=C)=CC=C1O YOMSJEATGXXYPX-UHFFFAOYSA-N 0.000 claims description 22
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims description 22
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 22
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims description 22
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- IAEGWXHKWJGQAZ-UHFFFAOYSA-N trimethylpyrazine Chemical compound CC1=CN=C(C)C(C)=N1 IAEGWXHKWJGQAZ-UHFFFAOYSA-N 0.000 claims description 14
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- 235000013325 dietary fiber Nutrition 0.000 description 21
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Classifications
-
- 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
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/201—Compounds of unspecified constitution characterised by the chemical reaction for their preparation
-
- 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
- A21D13/00—Finished or partly finished bakery products
- A21D13/02—Products made from whole meal; Products containing bran or rough-ground grain
-
- 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
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
-
- 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
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
- A21D2/36—Vegetable material
-
- 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
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3472—Compounds of undetermined constitution obtained from animals or plants
Definitions
- the present invention relates generally to the improvement of wholesome ingredients used in food and beverage products.
- the present invention relates to the use of bran to enhance the value of food and beverage products and impart appealing organoleptic properties, such as an improved flavour.
- the present invention provides methods involving thermal treatment of bran, such as grain bran, for the preparation of flavour compositions having properties delaying the development of rancid off-notes in a food product, as well as uses of thus prepared compositions in food and beverage products.
- Bran the outer layer of cereal grain, is particularly rich in dietary fibres and essential fatty acids.
- Bran also contains starch, protein, vitamins, dietary minerals, but also phytic acid, which is an anti-nutrient that prevents nutrient absorption.
- the high oil content of some brans makes them subject to rancidity.
- Table 1 Composition of bran of different cereal origins (i.a. "Bran”, Wikipedia, 2016;
- Bran is an inexpensive waste material or by-product from various cereal-processing industries.
- corn bran is a by-product from industrial production of corn flour and corn starch (Kamboj and Rana, 2014).
- bran is mainly used as an animal feed.
- bran is known for its high nutritional value. It is a source of essential whole grain elements (e.g. dietary fibre, phenolic compounds) and of important flavour precursors (e.g. five carbon monosaccharides) that can be of high interest for further use in the food industry.
- bran is an interesting ingredient due to the presence of dietary fibre polysaccharides, including arabinoxylans. Arabinoxylan chains are made of 1,4-linked xylose units. Xylose units may be substituted with 2-, 3- or 2,3-linked arabinose residues.
- bran Use of bran by the food industry is currently very limited. Some commercial food producers use bran as a filler in their foods to reduce the caloric value of snack foods. Bran is sometimes used to enrich breads (notably muffins) and breakfast cereals, especially for the benefit of those wishing to increase their intake in dietary fibre. Rice bran in particular finds many uses in traditional Japanese cuisine also for pickling, fermentation etc. In Romania and Moldova, fermented wheat bran is traditionally used when preparing bors soup. In Mexico, the ancient practice of "nixtamalization", a sort of cooking in alkaline conditions, maximized the benefit of maize, which was the staple food of the area.
- corn bran can be categorized as traditional insoluble dietary fibre with high bulking effect, as opposed to soluble fibre, more extensively fermented in the gut. Direct corn bran supplementation in foods to increase nutritional value has been assessed through preparation and evaluation of cakes, cupcakes, muffins and bread.
- corn bran As health beneficial food ingredient, the current route is rather to modify its structure or to extract valuable compounds from it, as Xylanase Modified corn Fibre (XMF) (Hu et al., 2010, 2008, 2008). Yet, both extensive presence of intra- and extra-molecular cross-linkage and presence of complex side chains renders corn bran cell wall structure difficult to access for enzymes. Release of hemicellulose fragments (i.e. (arabino)-xylo-oligosaccharides) from corn bran by either chemical (alkali, acidic or methanolic solutions) or physical treatments is a more popular approach. Corn bran may as well be valorised as a texture modifier.
- XMF Xylanase Modified corn Fibre
- Extrusion could be considered as a relevant technique to incorporate dietary fibre-rich components such as corn bran, yet increasing dietary fibre levels while maintaining palatability of products is always challenging.
- Increasing dietary fibre concentration in formulations has almost invariably been found to reduce expansion volume of extruded food. Resulting products are dense, tough and non-crispy (Pai et al., 2009).
- insoluble dietary fibers will often reduce expansion and lead to texture less preferred by consumers, soluble dietary fibers (e.g. inulin, polydextrose, pectins) seem to have more moderate effects on texture of extrudates (Robin et al., 2012). They, however, represent a less cost-effective solution than insoluble dietary fibers which are more readily available and still underevaluated in human nutrition.
- Extrusion cooking has been considered as an approach to modify the functionality of dietary fibres.
- US 4,500,558 reports a modification of functional properties of corn bran by applying high temperature and high shear during extrusion.
- insoluble dietary fibre may also be physically (e.g. milling or microwave treatment) or chemically (e.g. alkaline or acid treatment) treated prior to extrusion.
- US 2003/0104103 discloses how to reduce unpopular bitter taste associated with bran.
- the procedure is based on acidifying bran with an acid (pH 4-6) and treating with low levels of ozone to oxidize native bitter constituent, ferulic acid, preferably to vanillin to provide bran having a better flavour. It is claimed that during treatment concentration of ferulic acid decreases, whereas concentration of vanillin increases, both by factor of at least 50%.
- WO 2012/126972 describes a method for providing a whole grain cereal based extract, the method being based on grinding, hydrolysis of the macromolecular elements and separating of the insoluble fraction, which then undergoes a second grinding and/or enzymatic modification obtaining a fraction having improved suspension properties. This fraction is then incorporated into the soluble fraction thus obtaining the whole grain cereal based extract.
- WO 2006/127922 refers to stabilized whole grain corn flour having extended storage stability and modified functional properties as well as to methods of making the same.
- WO 2007/011685 discloses wet milling of a slurry from whole grain rice and wheat to release all the protein, fat, fibre, and starch components, resulting in a slurry that can be heated to gelatinize the starch and the subsequent product can be dried. The heated slurry can be treated by enzymatic hydrolysis via the process of liquefaction and optionally saccharification to produce whole grain rice milk products having diverse carbohydrate compositions.
- WO 2016/091952 concerns a process for preparing a wet-treated bran product, as well as the wet-treated bran product as such.
- the process provides a wet-treated bran product having a small particle size and improved expansion properties.
- US 2015/0359232 A1 discloses a wheat bran processed product which has a degree of gelatinization of 45% to 100%, a lipid content of 3.8 mass % or less, a moisture content of 2.5 mass% or more and a grain size of 0.1 mm or more.
- the product is obtained by heating a wheat bran slurry to a temperature from 60°C to 150°C.
- the wheat bran slurry contains 100 to 300 parts by mass of water per 100 parts by mass of wheat bran.
- the wheat bran is defatted by an overnight treatment in hexane. It is not clear from the disclosure which process parameter contributes to the target gelatinisation and lipid content.
- KR 2017/0077880 A discloses an extrusion process applied to a mixture comprising bran and 15% moisture at 100°C.
- the extruded bran is mixed with 10 times its weight of water, then it is then heated at 121°C for 1 hour under high pressure. After cooling, the slurry is hydrolysed with a cellulase.
- WO 2014/149810 A1 discloses a process to improve bran and germ flavour.
- NL 6613978 A discloses a method for the production of wheat bran with a nutty taste and smell, as well as a process for the preparation of bread.
- WO 2017/064172 A1 discloses a method of manufacturing a textured food product.
- Corn bran and corn fibre contain potentially useful components that may be harvested through physical, chemical or enzymatic means for the production of food ingredients or additives, including corn fibre oil, corn fibre gum, cellulosic fibre gels, xylo-oligosaccharides and ferulic acid. Components of corn bran and corn fibre may also be converted to food chemicals such as vanillin and xylitol.
- bran to become a useful and commercially valuable food ingredient has not been fully exploited yet. Namely, its potential for flavouring and shelf-life has not yet been exploited.
- the object of the present invention is to improve the state of the art, and in particular to provide compositions and methods that overcome the problems of the prior art and address the needs described above, or at least to provide a useful alternative.
- methods of treating bran are provided, thus preparing flavour compositions and compositions having properties delaying the development of rancid off-notes in a food product susceptible to rancidification.
- the inventors were surprised to see that the object of the present invention could be achieved by the subject matter of the independent claims.
- the dependent claims further develop the idea of the present invention.
- a first aspect of the invention relates to a method of preparing a flavour composition comprising the steps of:
- bran slurry comprising, or consisting of, bran and water, wherein the bran slurry comprises from 1% to 40% by weight of bran and has a water content of at least 20%, preferably at least 25%, by weight, based upon the weight of the bran slurry;
- step (b) subjecting the bran slurry provided in step (a) to a heat treatment at a temperature of from 155°C to 200°C for a holding time of 5 to 180 min;
- step (c) obtaining the heat-treated bran slurry produced in step (b) as the flavour composition.
- the method according to the first aspect may further comprise the steps of (d) filtering the heat-treated bran slurry to obtain a filtrate and residual solids, optionally drying the filtrate and/or the residual solids, optionally comminuting the dried filtrate and/or the dried residual solids.
- the method according to the first aspect may further comprise the steps of (e) drying the heat-treated bran slurry to obtain a dried heat-treated bran, and optionally comminuting the dried heat-treated bran.
- the bran is provided in the form of ground bran.
- the bran is bran from cereals selected from the group of barley, corn, millet, oat, rice, rye, sorghum, spelt or wheat, or from pseudo-cereals selected from the group of buckwheat or quinoa.
- the heat treatment is performed by microwave treatment, autoclaving, direct steam injection, treatment in a tubular heat exchanger, or treatment in a scrape surface heat exchanger.
- a second aspect of the invention relates to method of manufacturing a flavoured food product comprising the steps of:
- flavour composition obtainable or obtained by a method according to the first aspect
- step (b) blending said flavour composition and a food matrix; (c) optionally subjecting the blend provided in step (b) to a food processing treatment selected from the group of extrusion-cooking, drying, roller-drying, spray-drying, baking, retorting, or toasting; and
- a third aspect of the invention relates to a flavour composition comprising heat- treated bran obtainable or obtained by a method according to the first aspect, the flavour composition having properties delaying the development of rancid off-notes in a food product susceptible to rancidification.
- the flavour composition comprises an increased amount of a flavour compound selected from the group consisting of 2,3-butanedione, 2-acetylthiazole, guaiacol, 4-vinylguaiacol, vanillin, furfural, 4-hydroxy-2,5-dimethyl-3(2/-/)-furanone, 2-acetyl- 1-pyrroline, 2,3,5-trimethylpyrazine, 2-furylmethanethiol and 2-methyl-3-furanthiol, as compared to a composition comprising non-heat-treated bran.
- a flavour compound selected from the group consisting of 2,3-butanedione, 2-acetylthiazole, guaiacol, 4-vinylguaiacol, vanillin, furfural, 4-hydroxy-2,5-dimethyl-3(2/-/)-furanone, 2-acetyl- 1-pyrroline, 2,3,5-trimethylpyrazine, 2-furylmethanethiol and
- the flavour composition exhibits a flavour note selected from the group consisting of caramel, toasty, biscuity, vanilla-like, smoky, meaty, savoury, and spicy.
- Another aspect of the invention relates to the use of a flavour composition according to the third aspect as a flavour ingredient in a food product.
- Another aspect of the invention relates to the use of a flavour composition according to the third aspect as an ingredient for delaying the development of rancid off-notes in a food product susceptible to rancidification.
- Another aspect of the invention relates to a method of flavouring and/or of delaying the development of rancid off-flavours in a food product, said method comprising using a flavour composition according to the third aspect.
- Another aspect of the invention relates to a food product comprising a flavour composition according to the third aspect.
- the food product is obtainable or obtained by the method according to the second aspect.
- the food product, or flavoured food product is a roller-dried cereal product, a wafer, or an extruded product.
- the invention provides methods for efficiently valorisation of cereal bran by heat treatment.
- the inventors believe that the heat treatment may result in partial hydrolysis of the bran, which may develop antioxidative properties and may liberate some precursors, which may then become available for further reactions resulting in the formation of aroma compounds.
- the heat-treated bran exhibits several benefits, in particular (1) improved flavour properties, and (2) properties delaying the development of rancid off-notes.
- flavouring may be achieved either with natural flavours or ideally by application of "clean label” solutions.
- the latter and preferred alternative consists in generating flavour during the processing only from staple ingredients.
- the use of flavourings is restricted in several product categories such as for example the field of infant nutrition.
- the creation of intense and desirable flavour that is preferred by the consumers without using a flavouring ingredient is made possible by the present invention.
- heat treatment or “thermal treatment” shall be considered as having the same meaning.
- flavour composition refers to a composition which exhibits at least one flavour note and/or which contains at least one flavour compound.
- a “flavour note” relates to a flavour composition or compound, and is detectable by sensory evaluation, e.g. by sniffing or tasting.
- a “flavour ingredient” refers to a flavour composition or to one or more flavour compounds.
- rancid off-notes refers to the properties of some food ingredients to improve the preservation of the food into which they are incorporated, and it relates to the improvement of food shelf-life or food shelf-stability.
- a composition or a compound having "properties delaying the development of rancid off-notes” is considered to qualify as a food preservative or food preserving ingredient, in particular for preventing or delaying lipid oxidation. Lipid oxidation may result in the development of rancid off-notes.
- the development of rancid off-notes in a food product may be designated as "rancidification" of the food product.
- a soluble fraction of heat-treated bran is also referred to herein as “liquor” or “filtrate”.
- non-heat-treated bran herein also referred to as “native bran” or “original bran” refers to bran as obtained from a supplier and which has not been subjected to a thermal treatment. Also, native bran has not been subjected to a chemical treatment such as defatting with a solvent.
- an aspect of the invention is a method of preparing a flavour composition.
- This method uses wet heating to treat bran.
- wet heating of the bran is performed by autoclaving in a batch reactor, microwave heating, heating in a tubular heat exchanger or in a scrape surface heat exchanger.
- the present invention uses two procedures, i.e. microwave treatment and autoclaving, for treating bran.
- the bran is a crop grain bran.
- the bran may be a cereal grain bran or a pseudocereal grain bran.
- the bran is native bran.
- cereal grain bran include barley bran, corn bran, millet bran, oat bran, rice bran, rye bran, sorghum bran, spelt bran or wheat bran.
- pseudocereal grain bran include buckwheat bran or quinoa bran. Mixes of cereal grain brans, of pseudocereal grain brans, or of cereal and pseudocereal grain brans may be envisaged.
- the bran is a cereal grain bran selected from the group comprising, or consisting of, barley bran, corn bran, millet bran, oat bran, rice bran, rye bran, sorghum bran, spelt bran or wheat bran. More preferably, the bran is a cereal grain bran selected from the group comprising, or consisting of, wheat bran, corn bran, barley bran or spelt bran. In another preferred embodiment, the bran is a cereal grain bran selected from the group comprising, or consisting of, buckwheat bran or quinoa bran. Most preferably, the bran is corn bran, wheat bran or buckwheat bran. The choice of a specific crop grain bran may depend on the flavour notes that may be obtained from a given crop grain bran. Examples of flavour notes obtained from various brans are given in the examples below.
- the bran slurry comprises from 1% to 40% by weight of bran, preferably from 1% to 35% by weight of bran.
- the bran slurry may comprise from 5% to 40% by weight of bran, preferably from 5% to 35% by weight of bran.
- the bran slurry comprises from 1% to 30% by weight of bran, more preferably from 5% to 30% by weight, more preferably from 8% to 30% by weight, even more preferably from 8% to 27% by weight.
- the bran slurry comprises 10% to 30% by weight of bran.
- the bran slurry comprises a water content of at least 20%, 25% 30%, 40%, 50%, 60%, 70%, 80%, or 90% by weight, based upon the weight of the bran slurry.
- the bran slurry comprises a water content of from 20% to 99% by weight, preferably 25% to 95% by weight, preferably of from 30% to 95% by weight, more preferably of from 40% to 90% by weight, even more preferably of from 50% to 80% by weight, based upon the weight of the bran slurry.
- the bran slurry comprises a water content of from 80% to 99% by weight, preferably of from 85% to 95% by weight, more preferably of from 88% to 92% by weight, even more preferably of from 89% to 91% by weight, based upon the weight of the bran slurry.
- the bran slurry comprises at least 50% by weight of water and from 10% to 20% by weight of bran. In another preferred embodiment, the bran slurry comprises from 20% to 50% by weight of water and from 30% to 40% by weight of bran, based upon the weight of the bran slurry. In an embodiment, the bran slurry consists essentially of bran and water.
- the bran slurry comprises at least 50% by weight of water and from 10% to 20% by weight of bran and additional ingredients such as fats, protein sources, or carbohydrates. In another preferred embodiment, the bran slurry comprises from 20% to 50% by weight of water and from 30% to 40% by weight of bran, based upon the weight of the bran slurry, with additional ingredients such as fats, protein sources, or carbohydrates.
- the bran slurry may be prepared by mixing bran and water, and the optional additional ingredients mentioned above.
- the bran may be milled, ground or micronized.
- the bran is ground bran.
- the particle size of milled or ground bran is about 500 pm.
- the particle size of milled or ground bran ranges from 50 pm to 800 pm.
- the particle size of micronized bran is below 10 pm, such as below 1 pm.
- Ground bran may be used directly in the preparation of the bran slurry.
- native bran may be used in the preparation of a bran slurry. In such a case, the bran slurry may undergo a milling step in order to mill or grind the native bran. A milling step may also be used when the bran starting material is ground bran. This may be useful to further reduce the particle size of the ground bran.
- the bran slurry is subjected to a heat treatment.
- the heat treatment is performed at a temperature of from 155°C to 200°C for a holding time of 5 to 180 min, preferably of from 155°C to 200°C for 5 to 30 min, more preferably of from 155°C to 195°C for 5 to 20 min, or of from 175°C to 200°C for 5 to 15 min, even more preferably of from 160°C to 190°C for 5 to 15 min, or of 160°C to 175°C for 5 to 15 min, or of from 180°C to 200°C for 5 to 10 min.
- the heat treatment is performed at a temperature of 180°C for a holding time of 10 min, or of 160°C for 5 to 10 min, or of 200°C for 5 min.
- the inventors have found that a heat treatment of a bran slurry as defined above, at 155°C to 200°C for a holding time of 5 to 180 min, provides a flavour ingredient which is also suitable to reduce the development of rancid off-notes in food products susceptible to rancidification. This is shown in the examples.
- the heat treatment may be performed by direct steam injection, by treatment in a tubular heat exchanger, or by treatment in a scrape surface heat exchanger.
- the heat treatment is a microwave treatment, preferably performed at a temperature of 180°C for 10 min.
- the microwave treatment also involves a 15 to 25 minutes heating period, to reach 180°C to 200°C, starting from a temperature of 15°C to 30°C.
- the microwave treatment may be performed at 1,600 watts at 100% power of the microwave reactor, preferably at a power corresponding to 100% power of a MARS (Microwave Assisted Reaction Vessel, CEM) microwave laboratory reactor.
- the microwave treatment produces a pressure inside a vessel containing the bran slurry of about 7.5 bar. It is believed that apart from the heating effect, microwave radiation has also a physical impact on bran components that facilitates its hydrolysis.
- the heat treatment is performed by autoclaving preferably performed at a temperature of 160°C for 5 to 10 min.
- the autoclaving treatment involves a heating period of 15 to 150 min to reach 160°C, starting from a temperature of 15°C to 30°C. The heating period depends, i.a., on the type of equipment, on the batch size and on the total solids of the bran slurry.
- the heat treatment is performed in a closed vessel. This allows for building up pressure and for heating to a temperature beyond the boiling point of water.
- the bran slurry may be placed in a closed treatment vessel.
- the continuous heat- treatment device comprises pressure control devices to ensure that the heat treatment is performed under pressure.
- the heat-treated bran slurry may be subjected to further processing before being used in the preparation of flavoured food products.
- the heat-treated bran slurry may be filtered to obtain a soluble fraction of heat-treated bran slurry or liquor (filtrate) on the one hand, and residual solids on the other hand.
- the heat-treated bran slurry is cooled down to ambient temperature prior to being filtered.
- the filtrate and the residual solids retain specific flavour notes.
- the filtrate comprises mainly soluble components.
- the residual solids comprise mainly non-soluble components.
- the heat-treated bran slurry or the filtrate may be concentrated.
- the filtrate and the residual solids may both be dried.
- the heat-treated bran slurry itself may be dried. Drying may be performed, for instance, by vacuum drying, roller-drying, or spray drying. The appropriate drying method can be selected by the skilled person.
- the dried heat-treated bran slurry, the dried filtrate or the dried residual solids may then be comminuted, milled or ground to lower particle size.
- the heat-treated bran slurry, the filtrate, or the residual solids may be freeze-dried.
- the heat-treated bran slurry, the filtrate, or the residual solids may be frozen and stored at low temperatures, such as at -80°C.
- the freeze-dried or the frozen heat-treated bran slurry, filtrate or residual solids may be milled or ground, to reduce particle size.
- the heat-treated bran slurry, the filtrate and the residual solids, dried or not dried, may be used as a flavour composition, for flavouring foods or beverages.
- Another aspect of the invention is a method of manufacturing a flavoured food product.
- the method comprises a step of providing a flavour composition as described above, i.e. obtainable or obtained by the method of preparing a flavour composition according to the first aspect of the invention.
- the flavour composition may be a heat-treated bran slurry, a filtrate made from it, or the residual solids obtained after filtration of the heat-treated bran slurry.
- An aspect of the invention also includes the use of a heat-treated bran slurry as a flavour ingredient in a food product.
- a filtrate obtained by filtering said heat-treated bran slurry, or the residual solids obtained by filtering said heat-treated bran slurry, may also be used as a flavour ingredient in a food product.
- Examples of foods include, without being limited to, culinary aids, cereal products, bakery products, dairy products, dairy-like products, snacks, confectionery products, or sauces.
- Examples of cereal products include, without being limited to, infant cereals, breakfast cereals, confectionery cereals, porridge preparations, wafers, doughs, batters for ready-to- cook cakes, ice-cream cones, biscuits, cakes, or breads.
- Examples of bakery products include, without being limited to, bread, doughs, viennoiserie, and the like.
- Examples of confectionery products include, without being limited to, chocolate, chocolate bars, or wafer bars.
- dairy products include, without being limited to, chilled desserts, fermented milk products such as yoghurt, non-fermented milk products, dessert mousses, milk powders, concentrated milks, evaporated milks, or creams.
- beverages include, without being limited to, powdered beverages, such as soluble powdered beverages, soluble coffee beverages, soluble cocoa beverages, soluble malted beverages, or ready-to-drink beverages, such as cereal shakes, milk shakes, coffee shakes, cocoa beverages, dairy beverages, plant-based beverages, or sport drinks.
- feed products include, without being limited to, dry feed products and wet feed products, which may be based on vegetables, cereals, or animal proteins.
- the food product is a wafer, a roller-dried cereal product or an extruded cereal product.
- the food product comprises at least 25% dry weight of plant-based material, such as materials selected from cereals, pseudo-cereals, legumes and pulses.
- plant-based material such as materials selected from cereals, pseudo-cereals, legumes and pulses.
- the food product may also comprise mixes of such plant-based materials.
- a first step in the preparation of a flavoured food product comprises blending the flavour composition and a food matrix.
- food matrices include dry mixes, doughs, solutions or dispersions in a water-based or a fat-based liquid, or emulsions.
- food matrices comprise the standard ingredients useful for preparing a food product.
- the food matrices may be a dairy composition, a cereal composition, a vegetable composition, a protein composition, such as meat- or fish-based compositions, or a fat-based composition.
- the food matrix may be dry, fat or wet.
- a flavoured dry mix may be obtained directly.
- a flavoured ready-to-use cereal product may be obtained by mixing ready-to-use cereals, such a roller-dried cereals, with the dried flavour composition.
- the blend of the flavour composition with the food matrix is subjected to further food processing treatment(s), such as, without being limited to, extrusion-cooking, drying, roller-drying, spray-drying, baking, retorting, or toasting.
- the food processing treatment is roller-drying, extrusion cooking or baking.
- the flavour composition is blended with flour.
- the flour may be whole grain flour, refined flour, pseudo-cereal flour, or flour from other vegetables such as legumes (grains of Fabacae).
- the ratio of (dry) heat-treated bran to (whole grain) flour may range from 1:5 (w/w) to 1:3 (w/w).
- the ratio of (dry) heat-treated bran to (whole grain) flour is 1:4 (w/w).
- the blend may then be mixed with water, or other liquids, and subjected to standard processing of doughs.
- the food processing treatment is extrusion-cooking.
- the extrusion-cooking is performed at a temperature of from 100°C to 150°C, preferably of from 120°C to 140°C, more preferably of from 125°C to 135°C.
- the extrusion cooking may be performed at 22% humidity, 130°C and 400 rpm, preferably at rpm corresponding to 400 rpm of a laboratory extruder Eurolab 16 (Thermo Fischer).
- the food processing treatment is wafer-baking.
- wafer-baking is performed at a temperature of from 120°C to 170°C, more preferably at a temperature of 160°C for 110 s.
- the food processing treatment is wet-mixing.
- the heat- treated bran slurry, or preferably the concentrated filtrate, or the dried heat-treated bran slurry, or the dried filtrate, or the dried residual solids may be mixed in a standard process for preparing a ready-to-drink beverage.
- the food processing treatment is dry-mixing.
- the dried heat- treated bran slurry, or the dried filtrate, or the dried residual solids may be mixed in a standard process for preparing a powdered soluble beverage, or an infant cereal composition.
- flavour composition comprising heat-treated bran obtainable or obtained by a method according to the first aspect.
- the flavour composition comprising heat-treated bran has properties delaying the development of rancid off-notes in a food product susceptible to rancidification. Therefore, the flavour composition may be used to increase the shelf-life of a food product.
- the flavour composition comprising heat-treated bran may be considered as a natural food preservative.
- the flavour composition comprising heat-treated bran exhibits a flavour note, preferably a distinct flavour note, selected from the group consisting of caramel, sweet, vanilla-like, toasty, biscuity, smoky, meaty, savoury, and spicy.
- a flavour note preferably a distinct flavour note, selected from the group consisting of caramel, sweet, vanilla-like, toasty, biscuity, smoky, meaty, savoury, and spicy.
- the flavour- notes are detectable by sniffing or tasting, more preferably are identified by the aid of a trained assessor.
- the flavour composition comprising heat-treated bran exhibits caramel, sweet, vanilla-like, toasty, biscuity, smoky, and spicy flavour notes, preferably distinct flavour notes.
- the flavour composition comprising heat- treated bran exhibits meaty and savoury flavour notes, preferably distinct flavour notes.
- the flavour notes depend on the bran origin. For instance, heat-treated corn bran may exhibit caramel, sweet, vanilla-like, clove-like flavour notes. Also for instance, heat-treated wheat bran may exhibit biscuity, vanilla-like, toasty flavour notes. Also for instance, heat-treated buckwheat bran may exhibit meaty and savoury flavour notes.
- the flavour composition comprising heat-treated bran exhibits an enhanced flavour note selected from the group consisting of caramel, sweet, vanilla-like, toasty, biscuity, smoky, and spicy, as compared to a composition comprising non-heat-treated bran.
- the flavour composition comprising heat-treated bran exhibits an enhanced flavour note selected from the group consisting of meaty and savoury flavour notes, as compared to a composition comprising non-heat-treated bran.
- the flavour composition comprising heat-treated bran exhibits enhanced flavour notes of caramel, sweet, vanilla-like, toasty, biscuity, smoky, and spicy, as compared to a composition comprising non-heat-treated bran.
- the flavour composition comprising heat-treated bran exhibits enhanced flavour notes of meaty and savoury flavour notes, as compared to a composition comprising non-heat-treated bran.
- the flavour composition comprising heat-treated bran comprises a flavour compound selected from the group consisting of 2,3-butanedione, 2-acetylthiazole, guaiacol, 4-vinylguaiacol, vanillin, furfural, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, 2-acetyl- 1-pyrroline, 2,3,5-trimethylpyrazine, 2-furylmethanethiol and 2-methyl-3-furanthiol.
- a flavour compound selected from the group consisting of 2,3-butanedione, 2-acetylthiazole, guaiacol, 4-vinylguaiacol, vanillin, furfural, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, 2-acetyl- 1-pyrroline, 2,3,5-trimethylpyrazine, 2-furylmethanethiol and 2-methyl-3-furanthiol.
- the flavour composition comprising heat-treated bran comprises the flavour compounds 2,3-butanedione, 2-acetylthiazole, guaiacol, 4-vinylguaiacol, vanillin, furfural, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, 2-acetyl-l-pyrroline, 2,3,5- trimethylpyrazine, 2-furylmethanethiol and 2-methyl-3-furanthiol.
- flavour compounds are detectable and/or quantifiable using common laboratory methods, e.g. solid phase micro extraction, gas chromatography, tandem mass spectrometry, HS-SPME-GC/MS/MS, stable isotope dilution assay (SIDA).
- common laboratory methods e.g. solid phase micro extraction, gas chromatography, tandem mass spectrometry, HS-SPME-GC/MS/MS, stable isotope dilution assay (SIDA).
- the flavour composition comprising heat-treated bran comprises increased amounts of a flavour compound selected from the group consisting of 2,3- butanedione, 2-acetylthiazole, guaiacol, 4-vinylguaiacol, vanillin, furfural, 4-hydroxy-2,5- dimethyl-3(2H)-furanone, 2-acetyl-l-pyrroline, 2,3,5-trimethylpyrazine, 2-furylmethanethiol and 2-methyl-3-furanthiol, as compared to a composition comprising non-heat-treated or (native) bran.
- a flavour compound selected from the group consisting of 2,3- butanedione, 2-acetylthiazole, guaiacol, 4-vinylguaiacol, vanillin, furfural, 4-hydroxy-2,5- dimethyl-3(2H)-furanone, 2-acetyl-l-pyrroline, 2,3,5-trimethylpyrazine, 2-fur
- the flavour composition comprising heat-treated bran comprises an increased amount of a flavour compound selected from 4-hydroxy-2,5-dimethyl-3(2H)- furanone and/or 2-acetyl-l-pyrroline, as compared to a composition comprising non-heat- treated bran, when heat treatment is performed by autoclaving.
- the flavour composition comprising heat-treated bran comprises increased amounts of vanillin as compared to a composition comprising non-heat-treated treated bran.
- the amounts of vanillin are increased by at least 5-fold, 10-fold, 15- fold, or 20-fold as compared to a composition comprising non-thermally treated bran or native bran.
- the flavour composition comprising heat-treated bran does not comprise increased amounts of hexanal.
- the amounts of hexanal are lower by at least 20-fold, 30-fold, or 40-fold as compared to a composition comprising non-heat-treated or native bran.
- the amounts of hexanal are lower by about 40-fold, e.g. 36- fold as compared to a composition comprising non-heat-treated or native bran.
- the flavour composition comprising heat-treated bran has improved sensory characteristics.
- the flavour composition comprising heat-treated bran has properties delaying the development of rancid off-notes in a food product susceptible to rancidification. For instance, after storage, e.g. at 40°C for an extended period of time such as 30 to 40 weeks, an extrudate containing native corn bran is characterized by a strong rancid aroma, which is not present in an extrudate comprising heat-treated bran according to the present invention.
- flavour composition obtainable by, or obtained by, a method according to the first aspect of the invention, may be used as an ingredient for delaying the development of rancid off-notes in a food product susceptible to rancidification. This may improve the shelf- life of a food composition comprising such a flavour composition.
- Figure 1 shows the relative concentration of odorants (%) in corn bran after microwave-assisted heat-treatment in MARS reactor (original corn bran set at 100%).
- Figure 2 shows the relative concentration of odorants (%) in extrudate containing thermally-treated corn bran prepared by microwave-assisted heat-treatment in MARS reactor; concentration of odorants in extrudate containing original corn bran set as 100%.
- Figure 3 shows the relative concentration of odorants (%) in Wafer C prepared with the soluble fraction of heat-treated corn bran; concentration of odorants in Wafer B prepared with extract of native corn bran set as 100%.
- Figure 4 shows the relative concentration of odorants (%) in heat treated wheat bran prepared in a laboratory autoclave as compared to native wheat bran set as 100%.
- Figure 5 shows the relative concentration of odorants (%) in Wafer A prepared with heat treated wheat bran expressed to the concentration of odorants in Wafer B prepared with native (non-treated) wheat bran set as 100%.
- Figure 6 shows the evolution of pentane concentration along an accelerated shelf-life test, in a reference product (A), a product containing non-heat-treated bran (B) and a product containing heat-treated bran (C).
- the product is a roller-dried milky porridge composition. More details are found in Example 11.
- the sample (1 g ⁇ 0.002 g) was weighted into a 20 mL headspace vial.
- 500 mg cysteine was also added to the mixture in order to release both thiols from the disulphide bounding to the matrix.
- the vial was closed with a screw cap and the mixture was homogenized by means of a vortex agitator for 5 s and then stirred for 15 min using a magnetic stirrer.
- the analytes were identified by comparing their retention times and fragmentation patterns with corresponding standards.
- the concentrations were calculated from the abundances (peak areas) of the ions selected for the analytes and the internal standards and from the amounts of added internal standards.
- the quantities of the internal standards were adjusted to obtain a peak area ratio of analyte/standard between 0.2 and 5.
- the ions (transitions) used for the quantification by stable isotope dilution assay are listed together with applied collision energies in Table 2.
- Table 2 Selected ions used for the quantification of aroma compounds by means of stable isotope dilution assays
- Pentane is an autoxidation product of linoleic acid (C-18:2) that is formed by homolytic b-scission of corresponding 13-hydroperoxide. The scission on the other side of 13- hydroperoxide provides hexanal that is also often used a marker of lipid oxidation. While hexanal is a reactive aldehyde and may undergo different reactions with matrix components, pentane is a stable hydrocarbon that is cumulated over the storage and thus indicates well the extent of lipid oxidation.
- Pentane was determined in the headspace of sealed aluminium cans using an internally design prototype (Nestle PTC Orbe) coupling a sampler and gas chromatography analysis using flamme ionisation as detection system (GC-FID, Perkin Elmer Clarus 500). Quantification was done using pentane gas as standard.
- Aroma of thermally-treated corn bran exhibited distinct caramel, sweet, vanilla like, smoky, and spicy notes, as compared to native corn bran that was perceived rather bland with typical hey/straw-like and raw cereal notes.
- Freeze dried thermally-treated corn bran prepared as described in Example 2 was mixed with whole grain corn flour in ratio 1:5 (w/w) and was extruded using laboratory extruder Eurolab 16 (Thermo Fischer) at 22% humidity, 130°C and 400 rpm.
- a reference extrudate was prepared analogously employing native (non- treated) corn bran instead of thermally treated corn bran.
- Aroma of extrudate containing thermally treated corn bran was significantly improved as compared to aroma of extrudate containing original corn bran.
- Aroma of extrudate containing thermally treated corn bran exhibited caramel, sweet, vanilla-like, smoky, and spicy notes, while aroma of extrudate containing native corn bran was rather bland with typical raw cereal notes.
- Example 4 Shelf-life test with extrudate containing thermally treated corn bran
- Cereal extrudates prepared as described in Example 3 were subjected to accelerated shelf-life study. 1 g of milled extrudate containing either native corn bran (reference) or thermally treated corn bran were placed into 20 mL headspace vial. The vial was closed with a screw cap and stored in an oven at 40°C for 33 weeks.
- Non-soluble residues were filtered out using a paper filter and a Buchner funnel to obtain a liquor (soluble fraction).
- a corn bran extract (reference) was prepared by stirring of 25 g native corn bran in 250 mL water at ambient temperature for one hour using a magnetic stirrer. The extract was filtered using a paper filter and a Buchner funnel to obtain a soluble fraction.
- Aroma of soluble fraction of treated corn bran (liquor) and corn bran extract was evaluated by sniffing (10 assessors). Aroma of corn bran liquor was classified far stronger and much more pleasant as compared to aroma of corn bran extract. Aroma of corn bran liquor exhibited caramel, sweet, vanilla-like, smoky, and spicy notes, while aroma of corn bran extract was rather bland with some greenish and raw cereal notes.
- Example 6 Use of soluble fraction of thermally treated corn bran and corn bran extract in wafer baking
- Soluble fraction of thermally treated corn bran (liquor) and soluble fraction of corn bran extract prepared as described in Example 5 were applied in wafers in order to evaluate their potential to modulate flavour. Standard wafer without any addition of corn bran was also prepared. Batters were prepared with the following formulation (Table 3):
- Wafers (9-11 g each) were prepared by baking at 160°C for 110 s using laboratory equipment for production of wafer sheets (Hebenshaw).
- flavour of both wafers was described as bland with raw cereal notes.
- flavour of wafer containing liquor from treated corn bran was described as significantly improved, exhibiting caramel, sweet, burnt sugar, smoky, clove, and spicy attributes.
- Wafer containing corn bran liquor was also found crispier as compared to reference wafer or wafer with corn bran extract.
- Wafers were grinded using a coffee grinder (Tristar) and concentrations of selected odorants were determined. Analysis of aroma compounds revealed that the content of the following odorants was significantly higher in wafer with heat-treated corn bran (C) than in wafer with corn bran extract (B) (concentration ratio in brackets): 2,3-butanedione (buttery, 3), guaiacol (smoky, sweet 58), 4-vinylguaiacol (clove-like, 26), vanillin (vanilla-like, 190), furfural (caramel/bready, 182).
- Figure 3 shows the relative concentration of odorants (%) in Wafer C expressed to the concentration of odorants in Wafer B set arbitrary as 100 %.
- Aroma of the powder was evaluated by sniffing (10 assessors) and compared with aroma of the native wheat bran.
- Aroma of the treated wheat bran was classified far stronger and much more pleasant as compared to aroma of the native bran.
- Aroma of the treated bran exhibited caramel, biscuity, and spicy notes, while aroma of the native bran was rather bland with some greenish and raw cereal, straw-like notes.
- Example 8 Treatment of buckwheat bran in laboratory autoclave
- Buckwheat bran was treated in the laboratory autoclave and freeze-dried analogously as the wheat bran described in Example 7.
- the aroma of the obtained powder was evaluated by sniffing (10 assessors) and compared with that of the native buckwheat bran.
- Aroma of the treated bran was classified far stronger as compared to aroma of the native bran.
- Aroma of the treated bran exhibited distinct meaty, savoury, and sulphury notes, while aroma of the native bran was rather bland with some greenish and raw cereal, straw-like notes.
- the treated wheat bran prepared as described in Example 7 was applied in wafer preparation (Wafer D) in order to evaluate its potential to modulate flavour.
- a reference wafer (Wafer E) with addition of the native (non-treated) wheat bran was also prepared as well as a control wafer (Wafer F) without bran and based on refined wheat four. Batters were prepared with the following formulation: Table 5
- the ratio between the treated wheat bran and the refined wheat flour was intentionally set to 15% and 85% in order to reflect natural proportion of bran in whole grain flour.
- Wafers (9-11 g each) were prepared by baking at 160°C for 110 s using laboratory equipment for production of wafer sheets (Hebenrison).
- the ground wafers were subjected to an accelerated storage test. 5 g of ground wafer in 50 mL closed Pyrex bottle was stored in an oven at 40°C for 6 months. After storage, aroma was evaluated by 10 assessors. The aroma of Wafer E prepared with the original bran exhibited a distinct rancid off-note, while the aroma of Wafer D prepared with the treated bran remained pleasant with caramel, biscuity, and spicy notes. The control Wafer F, only made of refined flour also exhibited a distinct rancid off-note. This shows that the addition of bran was not the only driver to rancidity generation. To corroborate the different extent of rancidification, hexanal (marker of lipid oxidation) was determined in all samples.
- Wafer D prepared with the treated bran was 4 folds lower than in Wafer E prepared with the original bran (955 ppb) and up to 30 folds lower than in Wafer F with refined flour only (1763 ppb).
- Example 10 Treatment of wheat bran in a tubular heat exchanger
- a treated wheat bran slurry was produced at pilot scale by mixing native wheat bran and water at 80 °C using a ring layer mixer (AVA drynamix) and applying a ratio of 26 parts of bran for 64 parts of water.
- the bran slurry was then treated with water vapour to reach 160 °C and maintained at this temperature during 18 minutes (1090 seconds) by flowing in series of heat-jacketed tubes (Tubular Heat Exchanger, Nestle PTC Orbe). Steam was then released by flashing and the slurry collected once cooled below 60C. The product was kept at 4°C for 24 hours before incorporation in a full cereal-based recipe.
- Example 11 Use of the bran of example 10 in a roller dried milky porridge recipe
- the slurry was dried on a bi-cylinder roller dryer (ANDRYTZ Gouda) at 184 °C and 3 rpm and the dried film was milled using a 2 mm-sieve.
- the resulting powder was finally mixed with whole milk powder at a 87 :13 cereal powder : milk powder ratio.
- Product C prepared with the treated wheat bran as compared with Product B.
- Product C was also evaluated as more "toasty" than product B.
- Products were subjected to an accelerated storage test. 50 g of each product were packed in 1 L tin-cans, sealed and stored in a climatic chamber at 37 °C. Products were analysed every month for pentane (marker of lipid oxidation) and evaluated by sniffing. Sniffing assessment involved scoring the product on a scale from 0 to 10 for rancid notes. A score at 5 or below was considered as not acceptable.
- Figure 6 shows generation of pentane along the 6 months of storage in sealed tins at 37 °C.
- Product A reference product with preservatives
- Product B with native bran showed the highest pentane generation and scored at 5 or below by some assessors as early as after 3 months of storage.
- Product C with treated bran showed the smallest pentane generation and was never scored below 5.
Abstract
Description
Claims
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AU2011237844B2 (en) * | 2010-04-09 | 2015-01-22 | Dupont Nutrition Biosciences Aps | Bran modification |
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US20150250212A1 (en) * | 2012-09-26 | 2015-09-10 | Nederlandse Organisatie Voor Toegepast- Natuurwetenschappelijk Onderzoek Tno | New foods with modified cereal bran and methods for producing these |
WO2014104252A1 (en) | 2012-12-28 | 2014-07-03 | 花王株式会社 | Wheat bran processed product |
EP2983504B1 (en) * | 2013-03-15 | 2017-08-30 | Intercontinental Great Brands LLC | Bran and germ flavor and texture improvement |
WO2016091952A1 (en) | 2014-12-09 | 2016-06-16 | Nestec S.A. | Treatment of bran and products thereof |
CN105053757A (en) * | 2015-07-09 | 2015-11-18 | 安徽农业大学 | Rice bran stabilization treatment method |
ES2663326T3 (en) | 2015-10-16 | 2018-04-12 | Gold&Green Foods Oy | A method of manufacturing a textured food product and a textured food product |
KR101811701B1 (en) | 2015-12-28 | 2017-12-26 | 사조동아원 주식회사 | A working method of bran to improve immune function |
US10624356B2 (en) * | 2016-03-18 | 2020-04-21 | General Mills, Inc. | Refrigerated dough with extended shelf life made from white wheat flour |
JP6810543B2 (en) * | 2016-06-24 | 2021-01-06 | 昭和産業株式会社 | Processed wheat bran |
JP6755748B2 (en) * | 2016-08-23 | 2020-09-16 | 日東富士製粉株式会社 | Confectionery composition and method for improving confectionery composition |
-
2019
- 2019-03-07 EP EP19709049.1A patent/EP3761807A1/en active Pending
- 2019-03-07 CN CN201980013175.7A patent/CN111712138A/en not_active Withdrawn
- 2019-03-07 MX MX2020008281A patent/MX2020008281A/en unknown
- 2019-03-07 SG SG11202006789SA patent/SG11202006789SA/en unknown
- 2019-03-07 BR BR112020015988-3A patent/BR112020015988A2/en unknown
- 2019-03-07 WO PCT/EP2019/055732 patent/WO2019170813A1/en unknown
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RU2020131992A (en) | 2022-03-29 |
SG11202006789SA (en) | 2020-08-28 |
CN111712138A (en) | 2020-09-25 |
WO2019170813A1 (en) | 2019-09-12 |
MX2020008281A (en) | 2020-09-18 |
BR112020015988A2 (en) | 2020-12-15 |
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