Concentrated flavor composition

Abstract

The present invention relates to a method for preparing a dehydrated and dealcoholized flavor composition by reducing or removing water and ethanol from a flavor composition, comprising treating the flavor composition by a dehydration process and a dealcoholization process, as well as flavor compositions obtainable by this method, flavored consumer products containing them, and methods and uses thereof.

Description

[Technical Field]

[0001] The present invention relates to a method for preparing a dehydrated and dealcoholized flavor composition by reducing or removing water and ethanol from a flavor composition, comprising treating the flavor composition by a dehydration process and a dealcoholization process, as well as flavor compositions obtainable by this method, flavored consumer products containing them, and methods and uses thereof.

[0002] Background technology Water and ethanol may be present in a flavored product or composition due to manufacturing processes, for example in the beverage industry during the preparation of e.g., beer, sake, etc., or due to ethanol extraction of flavors from natural sources, e.g., plants, to obtain or concentrate specific flavor compounds. Reducing or removing water and / or ethanol from a flavored product or composition may be preferred, as a flavored product or composition obtained with reduced ethanol may be desirable from a health perspective and / or enrichment with flavor compounds within the flavored product or composition may be desirable from an organoleptic perspective.

[0003] WO 2008 / 099325 describes a process for concentrating the aroma profile of beverages, such as beer and wine, by extracting aromas from the original beverage using pervaporation and then adding the extracted aromas to the beverage after full or partial dealcoholization.

[0004] However, the prior art does not disclose or suggest the process according to the present invention.

[0005] One object of the present invention is to provide a method for reducing or preferably removing ethanol and water from a flavor composition in order to concentrate the flavor compounds in the flavor composition while avoiding the loss of volatile aroma compounds present in the flavor composition.

[0006] Another object of the present invention is a flavor composition for flavoring food compositions and products and beverage compositions and products, and / or comprising the proportion of flavor compounds of an initial flavor composition comprising water and ethanol.

[0007] Detailed Description of the Invention The present invention relates to a method for preparing a dehydrated and dealcoholized flavor composition by reducing or removing water and ethanol from a flavor composition, comprising treating the flavor composition by a dehydration process and a dealcoholization process, as well as flavor compositions obtainable by this method, flavored consumer products containing them, and methods and uses thereof. In other words, the present invention relates to a method for concentrating the amount of flavoring components in a flavor composition by reducing or removing water and ethanol from the flavor composition, comprising treating the flavor composition by a dehydration process and a dealcoholization process.

[0008] By "flavoring ingredient," "flavor compound," or similar phrases, we mean herein a compound used in a flavoring or perfuming preparation or composition to impart a pleasant effect. In other words, it should be recognized by those skilled in the art that such an ingredient to be considered a flavoring ingredient or perfuming ingredient is capable of imparting or modifying the taste or odor of the composition in a positive or desirable way, and does not merely have one taste or odor.

[0009] The flavor composition comprises water, ethanol, and a flavor-imparting component. In certain embodiments, the flavor composition is in the form of a solution or dispersion. Preferably, the flavor composition is in the form of a solution.

[0010] In certain embodiments, the flavor composition comprises ethanol in an amount of 5 to 95% by weight, preferably 40 to 90% by weight, more preferably 50 to 80% by weight, based on the total weight of the flavor composition, such that the flavor composition comprises ethanol in an amount of at least 5%, at least 40% and at least 50% by weight, and / or not more than 95%, not more than 90%, and not more than 80% by weight, based on the total weight of the flavor composition.

[0011] In certain embodiments, the flavor composition comprises water in an amount of 5 to 95% by weight, preferably 10 to 40% by weight, more preferably 20 to 30% by weight, based on the total weight of the flavor composition, such that the flavor composition comprises water in an amount of at least 5%, at least 10% and at least 20% by weight, and / or not more than 95%, not more than 90%, and not more than 80% by weight, based on the total weight of the flavor composition.

[0012] In a specific embodiment, the flavor composition comprises ethanol in an amount of 5 to 95% by mass, preferably 40 to 90% by mass, more preferably 50 to 80% by mass, and water in an amount of 5 to 95% by mass, preferably 10 to 40% by mass, more preferably 20 to 30% by mass, based on the total amount of the flavor composition. As a result, the flavor composition comprises ethanol in an amount of at least 5% by mass, at least 40% by mass, and at least 50% by mass, and / or not more than 95% by mass, not more than 90% by mass, and not more than 80% by mass, based on the total amount of the flavor composition, and water in an amount of at least 5% by mass, at least 10% by mass, and at least 20% by mass, and / or not more than 95% by mass, not more than 90% by mass, and not more than 80% by mass.

[0013] In certain embodiments, the flavor composition is a product from a dealcoholization process or a fermentation process or a product in distillation, whereby it is understood that the flavor composition may be an ethanol product, an intermediate product, and / or a by-stream product.

[0014] An alcohol product is understood as a desired end product of a dealcoholization process, a fermentation process, or a distillery, preferably in the beverage or food industry, which has an increased ethanol content compared to the starting material. An intermediate product is understood as a product of a dealcoholization process or a fermentation process, or a product in a distillery, preferably in the beverage or food industry, which cannot be used in the beverage or food industry itself, but must be further processed by additional processes in the beverage or food industry. The intermediate product may have an increased or decreased ethanol content compared to the starting material from the dealcoholization process.

[0015] A side stream product from a dealcoholization process is understood to be an undesired product of a delocalized process, preferably in the beverage or food industry, that has a reduced ethanol content compared to the starting material from the dealcoholization process. In a particular embodiment, the flavor composition is a side stream product of the dealcoholization process.

[0016] In certain embodiments, the flavor composition is a by-stream product from a dealcoholization process in the beverage or food industry.

[0017] In certain embodiments, the flavor composition is a by-stream product from a dealcoholization process in the beverage industry, for example in the dealcoholization process in the production of non-alcoholic or alcohol-free beer (i.e., beer having an ethanol content of less than 1.0% by weight, preferably less than 0.5% by weight, or more preferably less than 0.1% by weight) or low-alcohol beer (i.e., beer having an ethanol content of less than 4% by weight, preferably less than 2% by weight, more preferably less than 1.0% by weight).

[0018] In certain embodiments, the flavor composition is obtained by a reverse osmosis process, a spinning cone column process, or a distillation process, or by a fermentation process, or in a distillery.

[0019] In certain embodiments, the flavor composition is obtained as an ethanol product, intermediate product or by-stream product, preferably as a by-stream product, by a reverse osmosis process, a spinning cone column process or a distillation process.

[0020] In certain embodiments, the flavor composition is obtained by a reverse osmosis process as an ethanol product, intermediate product, or side stream product, preferably as a side stream product.

[0021] Reverse osmosis is understood as the process by which a solvent passes through a porous membrane in a direction opposite to the direction of natural osmosis when subjected to a hydrostatic pressure higher than the osmotic pressure.

[0022] In certain embodiments, the dehydration process is an adsorption process, a pervaporation process, or a forward osmosis process. Preferably, the dehydration process is a pervaporation process.

[0023] Pervaporation or pervaporation process is understood to be a process for separating a mixture of liquids by partial vaporization through a non-porous or porous membrane.

[0024] In certain embodiments, the dehydration process, preferably a pervaporation process, is carried out using a membrane, preferably a hydrophilic membrane.

[0025] By hydrophilic membrane is understood a membrane that is capable of moving or transporting water through the membrane and at the same time preventing the movement or transport of less hydrophilic and hydrophobic compounds.

[0026] In certain embodiments, the hydrophilic membrane is a porous hydrophilic membrane.

[0027] In certain embodiments, the hydrophilic membrane has a pore diameter in the range of 0.20 to 0.50 nm, preferably in the range of 0.23 to 0.42 nm, and more preferably in the range of 0.30 to 0.42 nm.

[0028] In a particular embodiment, the dehydration process, preferably the pervaporation process, is carried out using an organic or inorganic metal-containing membrane, preferably a hydrophilic membrane. Non-limiting examples of inorganic materials suitable for the membrane, preferably a hydrophilic membrane, include zeolites, and non-limiting examples of organic materials suitable for the membrane, preferably a hydrophilic membrane, include polyvinyl alcohol (PVA), chitosan, cellulose or its derivatives, polydimethylsiloxane (PDMS), poly(1-(trimethylsilyl)-1-propyne) (PTMSP), poly(styrene butadiene styrene) (SBS) or mixtures thereof. The choice of membrane is a function of the composition of the flavor composition, in particular the amount of water contained in the flavor composition, and those skilled in the art are fully capable of selecting the most suitable membrane in each case to optimize the dehydration process.

[0029] In certain embodiments, the membrane, preferably a hydrophilic membrane, comprises an inorganic material.

[0030] In certain embodiments, the hydrophilic membrane comprises a zeolite.

[0031] Zeolites are crystalline microporous aluminosilicates with an open framework structure of three-dimensional tetrahedral units that give rise to a network of pores and cavities with molecular dimensions.

[0032] In certain embodiments, the zeolite has a pore diameter in the range of 0.20 to 0.50 nm, preferably in the range of 0.23 to 0.42 nm, and more preferably in the range of 0.30 to 0.42 nm.

[0033] In certain embodiments, the hydrophilic membrane comprises NaA zeolite.

[0034] NaA zeolite is a + Type, Na 12 Al 12 Si 12 O 48It is understood as a synthetic zeolite with very small pores, usually synthesized at ≦27 H 2 O, and has a three-dimensional pore structure.

[0035] In certain embodiments, NaA has a pore diameter in the range of 0.20 to 0.50 nm, preferably in the range of 0.23 to 0.42 nm, and more preferably in the range of 0.30 to 0.42 nm.

[0036] In certain embodiments, the flavor composition is heated before being subjected to a dehydration process, preferably a pervaporation process.

[0037] In a particular embodiment, the flavor composition is heated to a temperature of 25 to 100°C, preferably 40 to 100°C, more preferably 60 to 100°C.

[0038] In another particular embodiment, the flavor composition is heated to a temperature of 25 to 100°C, preferably 30 to 80°C, more preferably 35 to 70°C.

[0039] Nevertheless, those skilled in the art will be well aware of suitable temperatures to use in this process step.

[0040] In certain embodiments, the dehydrated fraction comprises less than 50%, less than 40%, less than 25%, less than 5%, less than 1% water by weight based on the total dehydrated fraction.

[0041] In certain embodiments, the dehydrated fraction comprises the flavor compounds and / or ethanol of the flavor composition, i.e., at least 50% by weight of the flavor compounds and / or ethanol, at least 60% by weight of the flavor compounds and / or ethanol, at least 75% by weight of the flavor compounds and / or ethanol, and at least 95% by weight of the flavor compounds and / or ethanol, based on the total weight of the entire dehydrated fraction.

[0042] In certain embodiments, the hydrate fraction comprises the water of the flavor composition, i.e., at least 50% water, at least 60% water, at least 75% water, at least 95% water by weight relative to the total hydrate fraction.

[0043] In certain embodiments, the dehydration process, preferably the pervaporation process, results in a hydrate fraction that contains a small amount of water, e.g., less than 50%, less than 40%, less than 25%, less than 5%, less than 1% by weight of water relative to the total hydrate fraction, and a large amount of water, e.g., greater than at least 50%, at least 60%, at least 75%, at least 95% by weight of water relative to the total hydrate fraction.

[0044] In certain embodiments, the dehydrated fraction comprises the flavor compounds and / or ethanol of the flavor composition, i.e., at least 50% of the flavor compounds and / or ethanol, at least 60% of the flavor compounds and / or ethanol, at least 75% of the flavor compounds and / or ethanol, and at least 95% of the flavor compounds and / or ethanol, based on the total weight of the entire flavor composition.

[0045] In certain embodiments, the dehydrated fraction comprises less than 50%, less than 40%, less than 25%, less than 5%, less than 2% water by weight of the total flavor composition.

[0046] In certain embodiments, the hydrate fraction comprises the water of the flavor composition, i.e., at least 50% water, at least 60% water, at least 75% water, at least 95% water relative to the total flavor composition.

[0047] When the dehydration process is carried out by a pervaporation process, the hydrate side of the pervaporation module is under subatmospheric pressure.

[0048] In certain embodiments, the hydrate side of the pervaporation module has a subatmospheric pressure ranging from 1 mbar to 500 mbar, preferably from 1 to 200 mbar. Those skilled in the art will know how to select a suitable pressure for this process step.

[0049] In certain embodiments, the dealcoholization process is a distillation process, preferably a vacuum distillation process.

[0050] By this, it is understood that the ethanol contained in the dehydrated fraction from the dehydration step is removed, resulting in the flavor compounds remaining in the dehydrated fraction, thereby forming a dealcoholized fraction, with ethanol moving from the dehydrated fraction to the alcoholic fraction.

[0051] In a particular embodiment, the dealcoholization process, preferably the distillation process, is carried out at a temperature of 25 to 100°C, preferably 30 to 100°C.

[0052] In a particular embodiment, the dealcoholization process, preferably the distillation process, is carried out at a pressure between 1 mbar and 1 bar, preferably between 50 mbar and 500 mbar.

[0053] Preferably, the dealcoholization process, preferably a vacuum distillation process, is carried out at a pressure below atmospheric pressure, preferably in the range of 1 to 500 mbar, preferably 50 to 500 mbar.

[0054] In certain embodiments, the dealcoholized fraction comprises less than 90% by weight, less than 85% by weight, less than 80% by weight, less than 75% by weight, less than 70% by weight, less than 65% by weight, less than 60% by weight, less than 55% by weight, less than 50% by weight, less than 45% by weight, less than 40% by weight, less than 30% by weight, less than 25% by weight, less than 20% by weight, less than 15% by weight, less than 10% by weight, or less than 5% by weight of ethanol relative to the total dealcoholized fraction.

[0055] In certain embodiments, the dealcoholized fraction comprises the flavor compounds of the flavor composition, i.e., at least 5% by weight of the flavor compounds, at least 15% by weight of the flavor compounds, at least 25% by weight of the flavor compounds, and at least 35% by weight of the flavor compounds, relative to the total weight of the entire dealcoholized fraction.

[0056] In certain embodiments, the alcohol fraction comprises ethanol from the flavor composition, i.e., at least 50% by weight of ethanol, at least 60% by weight of ethanol, at least 75% by weight of ethanol, at least 95% by weight of ethanol relative to the total alcohol fraction.

[0057] In certain embodiments, the dealcoholization process, preferably the distillation process, results in a dealcoholized fraction comprising a small amount of ethanol, for example less than 90%, less than 85%, less than 80%, less than 75%, less than 70%, less than 65%, less than 60%, less than 55%, less than 50%, less than 45%, less than 40%, less than 30%, less than 25%, less than 20%, less than 15%, less than 10%, less than 5% by weight of ethanol relative to the total dealcoholized fraction, and a large amount of ethanol, for example an alcohol fraction of at least 50%, at least 60%, at least 75%, at least 95% by weight relative to the total alcoholized fraction.

[0058] In certain embodiments, the dealcoholized fraction comprises the flavor compounds of the flavor composition, i.e., at least 5% of the flavor compounds, at least 15% of the flavor compounds, at least 25% of the flavor compounds, and at least 35% of the flavor compounds relative to the total flavor composition.

[0059] In certain embodiments, the dealcoholized fraction comprises less than 90%, less than 85%, less than 80%, less than 75%, less than 70%, less than 65%, less than 60%, less than 55%, less than 50%, less than 45%, less than 40%, less than 30%, less than 25%, less than 20%, less than 15%, less than 10%, less than 5% ethanol by weight of the flavor composition.

[0060] In certain embodiments, the alcohol fraction comprises ethanol from the flavor composition, i.e., at least 50% ethanol, at least 60% ethanol, at least 75% ethanol, at least 95% ethanol relative to the total flavor composition.

[0061] In certain embodiments, treating the flavor composition with a dehydration and dealcoholization process results in a dehydrated and dealcoholized flavor composition, wherein the dehydrated and dealcoholized flavor composition is enriched in said flavor compared to the flavor composition.

[0062] By this it is understood that a dehydrated and dealcoholized flavor composition contains the same flavor compounds as a flavor composition, but in a higher weight percentage relative to the total flavor composition.

[0063] In certain embodiments, the amount of water and ethanol from the flavor composition is reduced by at least 1.5 fold, more preferably at least 20 fold, more preferably at least 40 fold, even more preferably at least 60 fold, and most preferably at least 70 fold, of said flavor compounds compared to a dehydrated and dealcoholized flavor composition.

[0064] In other words, the dehydrated and dealcoholized flavour composition is enriched in said flavour compounds by a factor of at least 1.5, more preferably at least 20, more preferably at least 40, even more preferably at least 60 and most preferably at least 70. Thereby it is understood that at least 3, preferably at least 5 and more preferably at least 7 of the flavour compounds must be enriched by said factor in the dehydrated and dealcoholized flavour composition compared to the flavour composition, i.e. the reference is the least enriched flavour compound in the dehydrated and dealcoholized flavour composition.

[0065] In certain embodiments, the dehydrated and dealcoholized flavor composition comprises the same ratio of flavor compounds relative to each other as the flavor composition, by which it is understood that the ratio of the major two, preferably three, more preferably four flavor compounds relative to each other is unchanged from the flavor composition compared to the dehydrated and dealcoholized flavor composition.

[0066] In certain embodiments, the flavor compounds are 1-propanol, isobutanol, 2-methyl-1-butanol, 3-methyl-1-butanol, ethyl octanoate, linalool, ethyl decanoate, phenylethyl acetate, octanoic acid, 2-methoxy-4-vinylphenol, dodecanoic acid, 3-methylbutyl acetate, ethylhexanoate, ethyl octanoate, ethyl dodecanoate, hexyl acetate, 3-methylbutyl butanoate, 3-methyl butyl hexanoate, 3-methylbutyl octanoate, 3-methylbutyl decanoate, propyl hexanoate, propyl octanoate, propyl decanoate, hexyl hexanoate, hexyl octanoate, isobutyl hexanoate, isobutyl decanoate, diisopentyl carbonate, 1-hexanol, 1-butanol, acetic acid, hexanoic acid, lactic acid, 2-phenylethanol, diethyl phthalate and / or 3-hydroxy-2-butanone.

[0067] In certain embodiments, the flavor compounds are 1-propanol, isobutanol, 2-methyl-1-butanol, 3-methyl-1-butanol, ethyl octanoate, linalool, ethyl decanoate, phenylethyl acetate, octanoic acid, 2-methyloxy-4-vinylphenol, and / or decanoic acid.

[0068] In a particular embodiment, the ratio of 1-propanol:2-methyl-1-butanol and 3-methyl-1-butanol is in the range of 1:2.5-8, preferably 1:3-6.5, more preferably 3.5-6.

[0069] In a specific embodiment, the ratio of 1-propanol:2-methyl-1-butanol and 3-methyl-1-butanol:isobutanol is in the range of 1:2.5-8.0:0.2-1.0, preferably 1:3.0-6.5:0.35-0.9, and more preferably 1:3.5-6.0:0.4-0.75.

[0070] In certain embodiments, the flavor compounds are 3-methylbutyl acetate, ethyl hexanoate, ethyl octanoate, ethyl decanoate, hexyl acetate, 3-methylbutyl butanoate, 3-methylbutyl hexanoate, 3-methylbutyl octanoate, 3-methylbutyl decanoate, propyl hexanoate, propyl octanoate, propyl decanoate, hexyl hexanoate, hexyl octanoate, isobutyl hexanoate, isobutyl decanoate, diisopentyl carbonate, 3-methyl-1-butanol, 2-methyl-1-butanol, 1-propanol, 1-hexanol, isobutanol, 1-butanol, acetic acid, hexanoic acid, octanoic acid, dodecanoic acid, lactic acid, 2-phenylethanol, phenylethyl acetate, 2-methoxy-4-vinylphenol, diethyl phthalate, and / or 3-hydroxy-2-butanone.

[0071] In a particular embodiment, the ratio of 1-propanol:2-methyl-1-butanol and 3-methyl-1-butanol is 1:2.5-16, preferably 1:3-13, more preferably 3.5-10.

[0072] In a specific embodiment, the ratio of 1-propanol:2-methyl-1-butanol and 3-methyl-1-butanol:3-methylbutyl acetate is in the range of 1:2.5-16:0.2-6, preferably 1:3.0-13:1-5, and more preferably 1:3.5-10:1.2-4.8.

[0073] In certain embodiments, the dehydration process and the dealcoholization process are carried out in two sequential processes.

[0074] Thereby it is understood that as a first step a dehydration process, preferably a pervaporation process, of the flavor composition is carried out, followed as a second step by dealcoholization, preferably distillation, of the dehydrated fraction from the dehydration process, without any additional processes between the two processes.

[0075] In certain embodiments, the dehydration process and the dealcoholization process are carried out in two consecutive processes and are included in one production line.

[0076] By this it is understood that the dehydration process and the dealcoholization process are spaced apart from one another but at the same time fluidly connected to one another.

[0077] In certain embodiments, the dehydration process and the dealcoholization process are carried out in two consecutive processes and are included in one production line in fluid connection with a preceding dealcoholization process from the beverage industry.

[0078] In an alternative embodiment, the dehydration process and the dealcoholization process are carried out in one single process.

[0079] By this it is understood that the dehydration and dealcoholization processes of the flavor composition are carried out in one single process, which can be done, for example, by selecting a particular hydrophilic membrane that is capable of reducing or removing both water and ethanol from the flavor composition.

[0080] In certain embodiments, the dehydration process and the dealcoholization process are carried out in one single process and are contained in one production line in fluid connection with a preceding dealcoholization process from the beverage industry.

[0081] The present invention also relates to a flavor composition obtainable by the process defined above.

[0082] In certain embodiments, the flavor composition obtainable by the method according to the present invention comprises a small amount of water, for example less than 50%, less than 40%, less than 25%, less than 5%, less than 1% by weight of water relative to the total flavor composition.

[0083] In certain embodiments, the flavour composition obtainable by the method according to the present invention comprises a small amount of ethanol, for example less than 90% by weight, less than 85% by weight, less than 80% by weight, less than 75% by weight, less than 70% by weight, less than 65% by weight, less than 60% by weight, less than 55% by weight, less than 50% by weight, less than 45% by weight, less than 40% by weight, less than 30% by weight, less than 25% by weight, less than 20% by weight, less than 15% by weight, less than 10% by weight, less than 5% by weight of ethanol relative to the total flavour composition.

[0084] In certain embodiments, the flavor composition obtainable by the method according to the present invention comprises a high amount of flavor compounds, such as at least 5% by weight of flavor compounds, at least 15% by weight of flavor compounds, at least 25% by weight of flavor compounds and at least 35% by weight of flavor compounds based on the total flavor composition.

[0085] In a particular embodiment, the flavor composition obtainable by the method according to the present invention is selected from the group consisting of 1-propanol, isobutanol, 2-methyl-1-butanol, 3-methyl-1-butanol, ethyl octanoate, linalool, ethyl decanoate, phenylethyl acetate, octanoic acid, 2-methoxy-4-vinylphenol, dodecanoic acid, 3-methylbutyl acetate, ethylhexanoate, ethyl octanoate, ethyl dodecanoate, hexyl acetate, 3-methylbutyl butanoate, 3-methylbutyl hexanoate. The flavor compounds may comprise at least one selected from the group consisting of methyl methyl octanoate, 3-methylbutyl decanoate, propyl hexanoate, propyl octanoate, propyl decanoate, hexyl hexanoate, hexyl octanoate, isobutyl hexanoate, isobutyl decanoate, diisopentyl carbonate, 1-hexanol, 1-butanol, acetic acid, hexanoic acid, lactic acid, 2-phenylethanol, diethyl phthalate, and / or 3-hydroxy-2-butanone.

[0086] In certain embodiments, the flavor composition obtainable by the method according to the present invention comprises at least one of 1-propanol, isobutanol, 2-methyl-1-butanol, 3-methyl-1-butanol, ethyl octanoate, linalool, ethyl decanoate, phenylethyl acetate, octanoic acid, 2-methyloxy-4-vinylphenol and / or decanoic acid flavor compounds.

[0087] Preferably, the flavor compositions obtained according to the invention comprise at least two, at least three, at least four, at least five, at least seven and at least nine of the above flavor compounds. In particularly preferred embodiments, the flavor compositions obtained according to the invention comprise all of the above flavor compounds.

[0088] In a particular embodiment, the flavour composition obtained according to the invention comprises at least 2.5%, preferably at least 3% and more preferably 4% by weight of 1-propanol relative to the total flavour composition.

[0089] In a particular embodiment, the flavour composition obtained according to the invention comprises at least 1% by weight, preferably at least 1.5% by weight and more preferably at least 2% by weight of isobutanol relative to the total flavour composition.

[0090] In a particular embodiment, the flavor composition obtained according to the present invention comprises at least 10% by weight, preferably at least 12.5% ​​by weight and more preferably at least 15% by weight of 2-methyl-1-butanol and 3-methyl-1-butanol relative to the total flavor composition.

[0091] In a particular embodiment, the flavor composition obtained according to the present invention comprises at least 0.001%, preferably at least 0.01% and more preferably at least 0.02% by weight of ethyl octanoate relative to the total flavor composition.

[0092] In a particular embodiment, the flavour composition obtained according to the invention comprises at least 0.001%, preferably at least 0.01% and more preferably at least 0.02% linalool by weight based on the total flavour composition.

[0093] In a particular embodiment, the flavour composition obtained according to the invention comprises at least 0.001%, preferably at least 0.01% and more preferably at least 0.02% by weight of decanoate relative to the total flavour composition.

[0094] In a particular embodiment, the flavour composition obtained according to the invention comprises at least 0.001%, preferably at least 0.01% and more preferably at least 0.02% by weight of phenylethyl acetate relative to the total flavour composition.

[0095] In a particular embodiment, the flavour composition obtained according to the invention comprises at least 0.001%, preferably at least 0.01% and more preferably at least 0.02% by weight of octanoic acid relative to the total flavour composition.

[0096] In a particular embodiment, the flavour composition obtained according to the invention comprises at least 0.001%, preferably at least 0.01% and more preferably at least 0.02% by weight of 2-methoxy-4-vinylphenol relative to the total flavour composition.

[0097] In a particular embodiment, the flavor composition obtained according to the invention comprises at least 0.001%, preferably at least 0.01% and more preferably at least 0.02% by weight of decanoic acid relative to the total flavor composition.

[0098] In a particular embodiment, the ratio of flavor compounds 1-propanol:2-methyl-1-butanol and 3-methyl-1-butanol is 1:2.5-8, preferably 1:3-6.5, more preferably 3.5-6.

[0099] In a particular embodiment, the ratio of flavor compounds 1-propanol:2-methyl-1-butanol and 3-methyl-1-butanol:isobutanol is in the range of 1:2.5-8.0:0.2-1.0, preferably 1:3.0-6.5:0.35-0.9, more preferably 1:3.5-6.0:0.4-0.75.

[0100] In certain embodiments, the flavor compositions obtained by the present invention contain 3-methylbutyl acetate, ethyl hexanoate, ethyl octanoate, ethyl decanoate, hexyl acetate, 3-methylbutyl butanoate, 3-methylbutyl hexanoate, 3-methylbutyl octanoate, 3-methylbutyl decanoate, propyl hexanoate, propyl octanoate, propyl decanoate, hexyl hexanoate, hexyl octanoate, isobutyl hexanoate, and / or 3-hydroxy-2-butanone.

[0101] In a particular embodiment, the ratio of 1-propanol:2-methyl-1-butanol and 3-methyl-1-butanol is 1:2.5-16, preferably 1:3-13, more preferably 3.5-10.

[0102] In a specific embodiment, the ratio of 1-propanol:2-methyl-1-butanol and 3-methyl-1-butanol:3-methylbutyl acetate is in the range of 1:2.5-16:0.2-6, preferably 1:3.0-13:1-5, and more preferably 1:3.5-10:1.2-4.8.

[0103] According to any embodiment of the present invention, at least one flavor carrier may be added to the flavor composition obtained by the present invention. The term "flavor carrier" refers to a material that is substantially neutral from the flavor point of view, as long as it does not significantly modify the organoleptic properties of the flavoring ingredient. The carrier may be liquid or solid.

[0104] Suitable liquid carriers include, for example, emulsifying systems, i.e., solvent and surfactant systems, or solvents commonly used in flavors or fragrances. A detailed description of the nature and type of solvents commonly used in flavors or fragrances is not exhaustive. Suitable solvents used in flavors include, for example, propylene glycol, triacetin, caprylic / capric triglyceride (neobee®), triethyl citrate, benzyl alcohol, ethanol, vegetable oils such as linseed oil, sunflower oil or coconut oil, or terpenes. Non-limiting examples of perfume solvents include solvents such as butylene or propylene glycol, glycerol, dipropylene glycol and its monoethers, 1,2,3-propanetriyl triacetate, dimethyl glutarate, dimethyl adipate, 1,3-diacetyloxypropan-2-yl acetate, diethyl phthalate, isopropyl myristate, benzyl benzoate, benzyl alcohol, 2-(2-ethoxyethoxy)-1-ethanol, or triethyl citrate, ethanol, water / ethanol mixtures, limonene, or other terpenes, isoparaffins such as those known under the trade name Isopar® (supplier: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trade name Dowanol® (supplier: Dow Chemical Company), or hydrogenated castor oil, such as those known under the trade name Cremophor® RH 40 (supplier: BASF), or mixtures thereof.

[0105] Suitable solid carriers include, for example, absorbent gums or polymers, or even encapsulating materials. Examples of such materials include wall-forming and plasticizing materials, such as mono-, di-, or polysaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetate, polyvinyl alcohol, proteins, or pectins, or further materials mentioned in references such as H. Scherz, Hydrokolloid: Stabilisatoren, Dickungs-und Geliermittel in Lebensmitteln, Band 2 der Schriftenreihe Lebensmittelchemie, Lebensmittelqualitaet, Behr's Verlag GmbH & Co., Hamburg, 1996. Encapsulation is a method well known to those skilled in the art and can be carried out using techniques such as spray drying, coagulation, extrusion, coating, plating, coacervation, etc.

[0106] According to any embodiment of the present invention, at least one flavor adjuvant may be added to the flavor composition obtained by the present invention. By "flavor adjuvant" is meant here an ingredient capable of imparting additional benefits, such as color (e.g., caramel), chemical stability, etc. A detailed description of the nature and type of adjuvants commonly used in flavoring compositions cannot be exhaustive. Nevertheless, such adjuvants are well known to those skilled in the art, who will be able to select them based on their general knowledge and according to the intended use or application. Specific, non-limiting examples include viscosity agents (e.g., emulsifiers, thickeners, gelling and / or rheology modifiers), stabilizers (e.g., antioxidants, heat / light and / or buffering agents), colorants (e.g., natural or synthetic substances or natural extracts that impart color), preservatives (e.g., antibacterial or antimicrobial or antifungal agents), vitamins, and mixtures thereof.

[0107] Furthermore, the flavor compositions obtained according to the invention can be advantageously used in the field of flavors to positively impart or improve the taste of consumer products to which said compositions are added. The present invention therefore relates to flavored consumer products comprising the flavor compositions obtained according to the invention.

[0108] For clarity, "flavored consumer products" refers to edible products or oral compositions, such as pharmaceutical compositions, edible gel mixtures and compositions, dental compositions, food beverages, and beverage products. Flavored consumer products may be in various forms. A non-exhaustive list of suitable forms of flavored consumer products may include fried, frozen marinated, battered, refrigerated, dehydrated, powder blended, canned, reconstituted, retorted, baked, cooked, fermented, microfiltered, pasteurized, blended, or preserved. Thus, a flavored consumer product according to the present invention comprises a flavor composition obtainable by the present invention and an optional active ingredient corresponding to the taste and flavor profile of the desired edible product, such as alcohol-free beer.

[0109] The nature and type of constituents of the food or beverage product do not warrant a more detailed description here, as those skilled in the art can choose the nature and type based on their general knowledge and in accordance with the nature of the product.

[0110] Typical examples of such flavored consumer products include: Baked goods (e.g. bread, dry biscuits, cakes, rice cakes, rice crackers, cookies, crackers, donuts, muffins, pastries, pre-mixes and other baked goods); Non-alcoholic beverages (e.g., alcohol-free beer, aqueous drinks, fortified / slightly sweetened water drinks, flavored carbonated and still mineral waters and table waters, carbonated drinks, non-carbonated drinks, sparkling water, still water, soft drinks, bottled drinks, sports / energy drinks, juice drinks, vegetable juices, vegetable juice preparations, broths), Alcoholic beverages (e.g., beer and malt beverages, low-alcohol beer, alcoholic drinks, wine, liquor), Instant or ready-to-drink beverages (e.g., instant vegetable drinks, powdered soft drinks, instant coffee and instant tea, black tea, green tea, oolong tea, herbal infusions, cocoa (e.g., water-based), tea-based beverages, coffee-based beverages, cocoa-based beverages, infusions, syrups, frozen fruit, frozen fruit juice, water-based ice, fruit ice, sorbet); Cereal products (e.g., breakfast cereals, cereal bars, energy / nutrition bars, granola, cooked rice products, rice flour products, millet and sorghum products, raw or cooked noodle and pasta products); Dairy-based products (e.g. fruit or flavored yogurt, ice cream, fruit ice, frozen desserts, fresh cheese, soft cheese, hard cheese, milk drinks, whey, butter, partially or totally hydrolyzed milk protein-containing products, fermented milk products, condensed milk and similar products) Dairy analogues (imitation dairy products) containing non-dairy ingredients (plant-based proteins, vegetable fats), Confectionery products (e.g. fillings, toppings, chewing gum, hard and soft candies), Chocolate and compound coatings (e.g. chocolate, spreads), Fats and oil or fat emulsion-based products (e.g., mayonnaise, spreads, regular or low-fat margarines, butter / margarine blends, flavored oils, shortenings, remoulades, dressings, salad dressings, spice products, peanut butter), Eggs or egg products (dried eggs, egg whites, egg yolks, custard), desserts (e.g. gelatin, pudding, dessert creams), Products made with soy protein or other soy ingredients (e.g., soy milk and products made therefrom, soy lecithin-containing products, fermented products such as tofu or tempeh or products made therefrom, soy sauce), Vegetable products (e.g., ketchup, sauces, processed and reconstituted vegetables, dried vegetables, frozen vegetables, cooked vegetables, pickled vegetables, vegetable concentrates or pastes, cooked vegetables, potato products), Fruit products (e.g. jams, marmalades, canned fruit) Vegetarian meat or meat substitutes, vegetarian burgers Spices or spice products (e.g. mustard products, horseradish products, pickles), spice mixtures and in particular seasonings used, for example, in the snack sector. snack products (e.g. baked or fried potato chips or potato dough products, bread dough products, corn, rice or peanut based extruded products); Ready-to-eat meals (e.g., instant noodles, rice, pasta, pizza, tortillas, wraps) and soups and stocks (e.g., stocks, savory cubes, dry soups, instant soups, prepared soups, retort soups), sauces (instant sauces, dry sauces, pre-made sauces, gravies, sweet sauces, relish sauces, sour sauces), Oral care products, such as toothpaste, mouthwash, dental care products (e.g. dental adhesives), dental rinses, mouth sprays, dental powders, dental gels, dental floss, Pet food or animal food.

[0111] Preferably, the flavored consumer product may be a non-alcoholic beverage, an alcoholic beverage, or an instant or ready-to-drink beverage.

[0112] Preferably, the flavored consumer products may be aqueous drinks, fortified / slightly sweetened water drinks, flavored carbonated and still mineral waters and table mineral waters, carbonated soft drinks, non-carbonated drinks, carbonated water, still water, soft, bottled water, sports / energy drinks, juice drinks, vegetable juices, vegetable juice products, alcohol-free beer, low-alcohol beer, beer and malt drinks, alcoholic beverages, wine, sake, instant vegetable drinks, powdered soft drinks, instant coffee and instant tea, black tea, green tea, oolong tea, herbal infusions, cocoa, tea-based drinks, coffee-based drinks, cocoa-based drinks, infusions and syrups.

[0113] Some of the flavored consumer products may be aggressive vehicles for the flavor compositions obtained according to the present invention and may therefore need to be protected from premature degradation, for example by encapsulation.

[0114] The proportion of the flavor composition obtained according to the invention that may be incorporated into the various said products varies within a wide range of values, depending on the nature of the consumer product to be flavored, as well as on the desired organoleptic effect and the nature of the auxiliary ingredients in a given base when the composition according to the invention is mixed with flavoring ingredients, solvents or additives customarily used in the prior art.

[0115] For example, in the case of flavored consumer products, typical concentrations are from 0.001 ppm to 10,000 ppm, more preferably from 0.1 ppm to 8,000 ppm, and even more preferably from 10 ppm to 5,000 ppm of the extract or composition of the present invention, based on the mass of the consumer product into which it is incorporated.

[0116] The present invention provides a) providing a food carrier or base or a beverage carrier or base, respectively; b) adding to a food carrier or base or a beverage carrier or base, respectively, the flavor composition obtained by the method defined above. The present invention relates to a method for producing a flavored food or beverage product, comprising:

[0117] It is thereby understood that the flavor compositions obtained by the method according to the present invention, when added to a food carrier or base or a beverage carrier or base, can increase, enhance, impart or modify the sensory profile of the food carrier or base or beverage carrier or base.

[0118] In certain embodiments, the food carrier or base may be fried or not fried, frozen or not frozen, low fat or not low fat, marinated, battered, refrigerated, dehydrated, instant, canned, reconstituted, retorted, or preserved.

[0119] In certain embodiments, the food carrier or base is a seasoning or spice, such as broth, savory cubes, or the like. cubes), powder mixes, flavored oils, sauces (e.g., relishes, barbecue sauces, dressings, gravies, or sweet and / or sour sauces), salad dressings, or mayonnaise; meat-based products, such as poultry, beef, or pork-based products, seafood, surimi, or fish sausages; soups, such as clear soups, cream soups, chicken or beef soup, tomato, or asparagus soup; carbohydrate-based products, such as instant noodles, rice, pasta, potato flakes or fries, noodles, pizza, tortillas, wraps; dairy or fat products, such as spreads, cheese, regular margarine, low-fat margarine, butter / margarine blends, butter, peanut butter, shortening, modified or flavored cheeses; flavored products, such as snacks, biscuits (such as chips or crisps) or egg products, potato / tortilla chips, microwave popcorn, nuts, pretzels, rice cakes, rice crackers, etc.; artificial products, such as dairy products (e.g., reformed cheeses made from oils, fats, and thickeners). Includes seafood or meat (e.g., vegetarian meat substitutes, veggie burgers) analogues; or pet or animal food.

[0120] In certain embodiments, the beverage carrier or base includes soft drinks, such as carbonated soft drinks, including cola, lemon-lime, root beer, heavy citrus ("dew-type"), fruit-flavored and cream sodas, and diet drinks; powdered soft drinks, and liquid concentrates, such as fountain syrups and cordials; coffee and coffee-based drinks, coffee substitutes, and cereal-based beverages; dry mix products and tea, including ready-to-drink teas (herbal and tea leaf-based); fruit and vegetable juices and juice-flavored beverages, as well as juice drinks, nectars, concentrates, and punches; carbonated and still sweetened and flavored waters; sports / energy / health drinks; alcoholic beverages, including beer and malt beverages, cider, and wine (still, sparkling, fortified wine, and wine coolers), and alcohol-free and other low-alcohol products; other beverages processed by heating (decoction, heat pasteurization, ultra-high temperature, ohmic heat, or industrial aseptic sterilization) and hot-fill packaging; and cool-fill products produced via filtration or other preservation techniques.

[0121] In certain embodiments, the method is preferably directed to producing a flavored beverage product.

[0122] The present invention also relates to the use of a flavor composition obtainable by the method defined above for producing a flavored food or beverage product.

[0123] Particular embodiments relating to methods of making flavored food or beverage articles apply mutatis mutandis to the use of the flavor compositions.

[0124] Example 1. Pervaporation Process The pervaporation membranes are made from NaA zeolites, a class of highly ordered, porous and crystalline silica-containing materials that exhibit uniform and very small pore sizes.

[0125] 300 cm in contact with the feed mixture2 Pervaporation experiments were carried out in a tubular laboratory stainless steel permeation cell with an effective membrane area of ​​1000 sq m. The feed liquid mixture was first heated by a heater before being pumped into the membrane module. A vacuum pump maintained the permeate side of the membrane module at subatmospheric pressure and provided the driving force for transporting water from the feed side to the permeate side. The permeate was condensed in two parallel glass cold traps cooled by liquid nitrogen to ensure complete collection of all permeate.

[0126] 2. Distillation Process Distillation experiments were carried out using standard laboratory units. A 1 L three-necked round-bottom flask stirred with a magnetic stirrer was used as the distillation pot. The column had a diameter of 25 mm and contained 33 cm of packing. All process parameters were controlled manually.

[0127] 3. Results and Discussion 3.1. Composition of the starting flavor composition The starting material, a side stream from a dealcoholization process in the beverage industry (beer) using reverse osmosis, was analyzed by GC-MS.

[0128] The main flavor compounds present in the side stream obtained from the dealcoholization process are shown in Table 1.

[0129] [Table 1]

[0130] In the starting material, the amounts of water and ethanol were about 74% and 25%, respectively, and the total aroma compounds were about 600 ppm.

[0131] 3.2. Aroma enrichment by direct distillation A side stream was subjected to direct distillation to concentrate the aroma or flavor compounds by removing ethanol and water. During the distillation process, the ratio of vacuum to reflux was adjusted. Initially, the vacuum was set to 125 mbar, the reflux ratio was set to 1, and the pot temperature was set to 37°C. At this stage, the results clearly show that 1-propanol and isobutanol were removed with ethanol and water. As the vacuum was reduced and the pot temperature increased in later distillation stages, more and more aroma or flavor compounds were distilled. These results indicate that aroma concentration by direct distillation did not work in this case.

[0132] 3.3. Water removal by pervaporation To remove water from the side stream, pervaporation experiments were carried out using the process reported in Example 1. The dehydration results are shown in Table 2. Because the experiment was carried out in batch mode, the concentration of water in the feed decreased over the experiment time. After 30 minutes, the water content had decreased to 0.2%.

[0133] This result indicates that the pervaporation process can efficiently remove water from the side stream.

[0134] [Table 2]

[0135] 3.4. Further concentration by distillation After dehydration, the resulting mixture was concentrated by distillation. The distillation conditions are listed in Table 3 using the settings reported in Example 2. A total of 857 grams of dehydrated material was subjected to distillation. After distillation, 832 grams of distillate and 7.8 grams of residue were collected.

[0136] [Table 3]

[0137] In the distillate portion, only ethanol and traces of water were found, and no aroma compounds were detected by GC. As shown in Table 4, after pervaporation and distillation, most of the major aroma compounds in the starting side stream increased by more than 80 times. This result indicates that a dehydration treatment is necessary and that further concentration would be beneficial.

[0138] [Table 4]

[0139] 4. Further Examples for Obtaining Flavor Compositions The starting material was wine. The dehydration and dealcoholization process was carried out as described in Examples 1-3.

[0140] [Table 5]

[0141] 5. Temperature Effects To understand the effect of temperature on the membrane performance, two experiments were carried out at 80° C. and 100° C. The material used was whiskey.

[0142] The experimental results are shown in Tables 6 and 7 below. This shows that a higher operating temperature can increase the flow rate, more specifically, the flow rate almost doubled from the initial state. On the other hand, it was found that the flow rate dropped sharply when the moisture content of the feedstock decreased to a certain level.

[0143] [Table 6]

[0144] [Table 7]

Claims

1. A method for producing a dehydrated and dealcoholized flavor composition by reducing or removing water and ethanol from a flavor composition obtained by a reverse osmosis process, comprising the steps of treating the flavor composition by a dehydration process and a dealcoholization process, wherein the dehydration process is an adsorption process or a pervaporation process carried out using a hydrophilic membrane, and the dealcoholization process is a distillation process.

2. 10. The method of claim 1, wherein the flavor composition is in the form of a solution or dispersion.

3. 3. The method according to claim 1 or 2, wherein the flavor composition comprises ethanol in an amount of 5 to 95% by weight and water in an amount of 5 to 95% by weight, based on the total amount of the flavor composition.

4. The method of any one of claims 1 to 3, wherein the membrane comprises a zeolite.

5. 5. The method of any one of claims 1 to 4, wherein the distillation process is a vacuum distillation process.

6. 6. The method of any one of claims 1 to 5, wherein the amount of water and alcohol from the flavor composition is reduced by at least a factor of two in the flavor composition.

7. The following steps, (a) providing a food carrier or base or a beverage carrier or base, respectively; (b) adding to a food carrier or base or a beverage carrier or base, respectively, a flavor composition obtainable by the method defined in any one of claims 1 to 6.

1. A method for producing a flavored food or beverage product, comprising:

8. 10. Use of a flavor composition obtainable by the method defined in any one of claims 1 to 6 for the preparation of a flavored food or beverage product.

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