Composition for determining unpleasant flavors derived from milk protein and composition for simulating unpleasant flavors derived from milk protein

Abstract

This invention provides a composition for determining unpleasant flavors derived from milk proteins and a composition for simulating unpleasant flavors derived from milk proteins. [Solution] A composition for determining unpleasant flavors derived from milk protein, containing one or more compounds selected from group A below, and a pseudo-unpleasant flavor composition of milk protein, containing one or more compounds selected from group A below. (Group A) 2-Propyl-2-octenal, 2-Pentylpyridine, 2-Butyl-2-octenal

Description

Technical Field

[0001] The present invention relates to a composition for determining an unpleasant flavor derived from milk protein, and a pseudo-unpleasant flavor composition for reproducing an unpleasant flavor derived from milk protein.

Background Art

[0002] Conventionally, casein and whey, which are the main components of milk proteins contained in the milk of dairy animals such as cows and goats, have high nutritional value and excellent solubility, emulsifying properties, and binding properties at low temperatures. Therefore, for these functions, in addition to infant formula milk, dairy products, and health foods, they are also used in liquid coffee creamers, processed meat products, etc. In particular, in recent years, the number of people consuming protein supplements (so-called protein) mainly composed of protein for the purpose of increasing muscle strength and muscle mass has been increasing. Various raw materials are used for commercially available protein, and as milk protein (milk protein) using milk as a raw material, there are mainly two types: whey protein and casein protein.

[0003] However, milk protein that has undergone concentration or drying processes in the manufacturing process has a specific unpleasant flavor known as so-called casein odor or whey odor (hereinafter referred to as "unpleasant flavor derived from milk protein" or "unpleasant flavor derived from milk protein"), and there is a problem that the palatability during eating and drinking is poor.

[0004] Patent Document 1 describes that the unpleasant flavor derived from milk protein is caused by methional, 2-methyl-3-furanthiol, and o-aminoacetophenone.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0006] However, the full extent of unpleasant flavors derived from milk proteins has not been elucidated. In the development of protein products, there has been a need for compositions to detect unpleasant flavors derived from milk proteins and for pseudo-unpleasant flavor compositions that reproduce these flavors, in order to efficiently identify these flavors and to develop masking flavors that suppress and / or improve them.

[0007] The object of the present invention is to provide a composition for determining unpleasant flavors derived from milk proteins and a pseudo-unpleasant flavor composition derived from milk proteins. [Means for solving the problem]

[0008] The present inventors conducted diligent research to solve the above problems and discovered that a component previously undetectable in milk protein significantly contributes to the unpleasant flavor derived from milk protein, thus completing the present invention.

[0009] Thus, a brief overview of some of the representative inventions disclosed in this application is as follows:

[0010] [1] A composition for determining unpleasant flavors derived from milk protein, containing one or more compounds selected from group A or group B below. (Group A) 2-Propyl-2-octenal, 2-Pentylpyridine, 2-Butyl-2-octenal (Group B) Methylmethylthioselenide, dimethyl diselenide, methylmethylselenyl disulfide [2] A composition for determining unpleasant flavors of consumer goods containing milk protein, comprising one or more compounds selected from group A or group B below. (Group A) 2-Propyl-2-octenal, 2-Pentylpyridine, 2-Butyl-2-octenal (Group B) Methylmethylthioselenide, dimethyl diselenide, methylmethylselenyl disulfide [3] A pseudo-unpleasant flavor composition of milk protein containing one or more compounds selected from group A or group B below. (Group A) 2-Propyl-2-octenal, 2-Pentylpyridine, 2-Butyl-2-octenal (Group B) Methylmethylthioselenide, dimethyl diselenide, methylmethylselenyl disulfide [4] A method for determining unpleasant flavors of consumer goods containing milk protein, using one or more compounds selected from Group A or Group B below as indicators. (Group A) 2-Propyl-2-octenal, 2-Pentylpyridine, 2-Butyl-2-octenal (Group B) Methylmethylthioselenide, dimethyl diselenide, methylmethylselenyl disulfide [5] A method for evaluating unpleasant flavors of consumer goods containing milk protein, comprising (a) a step of quantifying one or more compounds selected from the following group A or group B in the consumer goods. (Group A) 2-Propyl-2-octenal, 2-Pentylpyridine, 2-Butyl-2-octenal (Group B) Methylmethylthioselenide, dimethyl diselenide, methylmethylselenyl disulfide [6] A method for producing an unpleasant flavor composition derived from milk protein, comprising: (b) preparing a pseudo-unpleasant flavor composition of milk protein containing one or two compounds selected from the group consisting of group A or group B below; (c) preparing a plurality of candidate compositions for masking unpleasant flavors derived from milk protein; (d) adding each of the candidate compositions for masking unpleasant flavors to the pseudo-unpleasant flavor composition and evaluating the unpleasant flavor of the pseudo-unpleasant flavor composition after the addition; and (e) selecting from the candidate compositions for masking unpleasant flavors prepared in step (c) the one that shows the best evaluation result obtained in step (d) as the unpleasant flavor improving composition derived from milk protein. (Group A) 2-Propyl-2-octenal, 2-Pentylpyridine, 2-Butyl-2-octenal (Group B) Methylmethylthioselenide, dimethyl diselenide, methylmethylselenyl disulfide [Effects of the Invention]

[0011] According to the present invention, it is possible to provide a composition for determining unpleasant flavors derived from milk proteins and a pseudo-unpleasant flavor composition derived from milk proteins. [Modes for carrying out the invention]

[0012] The present invention will be described in more detail below with specific examples. In this specification, "~" means a range including the lower and upper limits, concentration (ppt, ppb, ppm, etc.) and % represent mass concentration and mass %, respectively unless otherwise specified, and concentration refers to the final concentration unless otherwise specified. In this specification, "greater than" means "above" and does not include the lower limit. In this specification, "flavor" means one or more senses that can be altered by aroma, typically including smell and / or taste. In this specification, the term "flavoring (to flavor)" includes adding a new flavor and / or enhancing a flavor, and also includes cases where the flavor is improved as a result of flavoring or enhancement. Furthermore, the term "flavoring" includes, as a result of flavoring, enhancing, suppressing, or improving sensations other than smell and / or taste, such as coldness, warmth, texture (including throat feel, firmness, viscosity, etc., also called texture), and stimulating sensations such as carbonation and spiciness. In this specification, the flavor of food and beverages may also be referred to as "flavor." In this specification, "addition" is almost synonymous with "combination," and includes at least one of simply adding to a substance by spraying, dropping, etc., and mixing with a substance.

[0013] In this specification, "unpleasant flavor derived from milk protein" means, as described above, the unpleasant flavor (unpleasant odor and / or unpleasant taste) that milk protein has undergone processing such as concentration and drying during the manufacturing process, and refers to the unpleasant flavor known as casein odor or whey odor.

[0014] [Composition for Judging Unpleasant Odor] The composition for judging unpleasant odor derived from milk protein according to one embodiment of the present invention (hereinafter sometimes referred to as "the present composition for judging unpleasant odor") contains one or more compounds selected from the following Group A (hereinafter sometimes referred to as "Group A compounds"). (Group A) 2-propyl-2-octenal, 2-pentylpyridine, 2-butyl-2-octenal

[0015] As described above, the present inventors conducted intensive studies to solve the above problems, and found that Group A compounds, which are components not detected conventionally from milk protein, greatly contribute to the unpleasant odor derived from milk protein. Thus, the present inventors found that a composition containing Group A compounds is useful as a composition for judging unpleasant odor derived from milk protein.

[0016] In the present embodiment, since the unpleasant odor derived from milk protein is substantially synonymous with the unpleasant odor of consumer goods containing milk protein, the composition containing Group A compounds is also useful as a composition for judging the unpleasant odor of consumer goods containing milk protein. Therefore, the composition for judging the unpleasant odor of consumer goods containing milk protein according to one embodiment of the present invention (hereinafter, unless it is necessary to distinguish from the composition for judging the unpleasant odor derived from milk protein according to the present embodiment, the composition for judging the unpleasant odor of consumer goods containing milk protein according to the present embodiment may also be referred to as "the present composition for judging unpleasant odor") contains one or more compounds (Group A compounds) selected from the following Group A. (Group A) 2-propyl-2-octenal, 2-pentylpyridine, 2-butyl-2-octenal

[0017] The composition for judging unpleasant odor derived from milk protein according to another embodiment of the present invention contains one or more compounds selected from the following Group B (hereinafter sometimes referred to as "Group B compounds"). (Group B) Methyl methylthioselenide, dimethyldiselenide, methyl methylselenyl disulfide

[0018] The inventors of the present invention conducted intensive research to solve the above problems, and as a result, found that group B compounds, which are components not previously detected from milk proteins, greatly contribute to the unpleasant odor derived from milk proteins. Thus, the inventors of the present invention found that a composition containing group B compounds together with group A compounds is useful as a composition for determining the unpleasant odor derived from milk proteins.

[0019] As described above, in the present embodiment, since the unpleasant odor derived from milk proteins is substantially synonymous with the unpleasant odor of consumer products containing milk proteins, the composition containing group B compounds is also useful as a composition for determining the unpleasant odor of consumer products containing milk proteins. Therefore, the composition for determining the unpleasant odor of consumer products containing milk proteins according to another embodiment of the present invention contains one or more compounds (group B compounds) selected from the following group B. (Group B) Methyl methylthioselenide, dimethyl diselenide, methyl methylselenyl disulfide

[0020] Further, as a preferred example, the composition for determining the unpleasant odor derived from milk proteins according to another embodiment of the present invention (hereinafter sometimes referred to as "the composition for determining the present unpleasant odor") contains one or more compounds (group A compounds) selected from the following group A and one or more compounds (group B compounds) selected from the following group B. (Group A) 2-Propyl-2-octenal, 2-Pentylpyridine, 2-Butyl-2-octenal (Group B) Methyl methylthioselenide, dimethyl diselenide, methyl methylselenyl disulfide

[0021] As described above, both group A compounds and group B compounds greatly contribute to the unpleasant odor derived from milk proteins. However, the inventors of the present invention found that by using group A compounds and group B compounds in combination, they contribute more greatly to the unpleasant odor derived from milk proteins than when group A compounds or group B compounds are used alone. Thus, the inventors of the present invention found that a composition containing group A compounds and group B compounds is even more useful as a composition for determining the unpleasant odor derived from milk proteins.

[0022] In this embodiment, since the unpleasant flavor derived from milk protein is substantially synonymous with the unpleasant flavor of consumer goods containing milk protein, a composition containing Group A compounds and Group B compounds is more useful as a composition for determining the unpleasant flavor of consumer goods containing milk protein than a composition containing Group A compounds or Group B compounds alone. Accordingly, a composition for determining the unpleasant flavor of consumer goods containing milk protein according to one embodiment of the present invention contains one or more compounds selected from Group A below (Group A compounds) and one or more compounds selected from Group B below (Group B compounds). (Group A) 2-Propyl-2-octenal, 2-Pentylpyridine, 2-Butyl-2-octenal (Group B) Methylmethylthioselenide, dimethyl diselenide, methylmethylselenyl disulfide

[0023] Compounds A and B (hereinafter sometimes collectively referred to as "the compounds in question") can be obtained by common methods such as commercially available reagents. Furthermore, the obtained compounds in question may be purified as needed using methods such as column chromatography or vacuum distillation.

[0024] Furthermore, when using the compound in question for the composition for determining unpleasant flavors, other components such as solvents for dissolution or dilution, stabilizers, antioxidants, fragrances, plant extracts, and other additives may be added together with the compound to prepare a composition suitable for practical use, such as for storage or use in determination tests.

[0025] One method of using the composition for determining unpleasant flavors is to qualitatively or quantitatively detect and measure the compound contained in the consumer product under evaluation, using the compound contained in the composition as a reference. Applicable equipment for this detection and measurement includes gas chromatography (GC) and high-performance liquid chromatography (HPLC). Alternatively, the compound contained in the consumer product under evaluation may be identified by GC / Olfactometry and its intensity compared to that of the compound in the composition for determining unpleasant flavors. Furthermore, a sensory evaluation may be conducted on both the composition for determining unpleasant flavors and the consumer product under evaluation, with scores assigned based on the compound contained in the composition. In addition, a combination of the above evaluation methods may be used.

[0026] In this embodiment, although not particularly limited, it was found that among the unpleasant flavors derived from milk protein (unpleasant flavors of consumer goods containing milk protein), 2-propyl-2-octenal, a group A compound, contributes to whey and mochi-like unpleasant flavors; 2-pentylpyridine contributes to earthy, earthy, roasty, and bitter unpleasant flavors; 2-butyl-2-octenal contributes to grassy, ​​metallic, and powdery unpleasant flavors; and methylmethylthioselenide, dimethyldiselenide, and methylmethylselenyl disulfide, all group B compounds, contribute significantly to animalic and vinyl-like unpleasant flavors.

[0027] In particular, it was found that combining 2-propyl-2-octenal with methylmethylthioselenide, dimethyl diselenide, or methylmethylselenyl disulfide contributes to the sticky, unpleasant flavor characteristic of whey, which is a milk protein; combining 2-pentylpyridine with methylmethylthioselenide, dimethyl diselenide, or methylmethylselenyl disulfide contributes to the earthy, unpleasant flavor characteristic of whey, which is a milk protein; and combining 2-butyl-2-octenal with methylmethylthioselenide, dimethyl diselenide, or methylmethylselenyl disulfide contributes to the grassy, ​​unpleasant flavor characteristic of milk proteins.

[0028] Therefore, the milk protein-derived unpleasant flavor determination composition according to this embodiment is useful as an unpleasant flavor determination composition derived from milk protein that has undergone processing such as concentration and drying, among other milk protein-derived unpleasant flavors, and is even more useful as an unpleasant flavor determination composition derived from various proteins, and is particularly useful as an unpleasant flavor determination composition derived from whey protein concentrate, whey protein isolate, milk protein concentrate, milk protein isolate, total milk protein, micellar casein isolate, micellar casein concentrate, acid casein, sodium caseinate, calcium caseinate, or rennet casein, as described later. Similarly, the composition for determining unpleasant flavors of consumer goods containing milk protein according to this embodiment is useful as a composition for determining unpleasant flavors of consumer goods containing milk protein that has undergone processing such as concentration or drying, is even more useful as a composition for determining unpleasant flavors of various proteins, and is particularly useful as a composition for determining unpleasant flavors of whey protein concentrate, whey protein isolate, milk protein concentrate, milk protein isolate, total milk protein, micellar casein isolate, micellar casein concentrate, acid casein, sodium caseinate, calcium caseinate, or rennet casein, as described later.

[0029] As mentioned above, the concentration of the compound in question in the composition for determining unpleasant flavors may be set to any appropriate concentration for the purpose of qualitatively or quantitatively detecting and measuring the compound in question contained in the consumer goods under evaluation, comparing its intensity with the compound detected from the consumer goods under evaluation by GC-Olfactometry, or performing a sensory evaluation together with the consumer goods under evaluation and assigning a score based on the compound in question contained in the composition for determining unpleasant flavors.

[0030] As shown in the examples, in consumer goods, 2-propyl-2-octenal, a Group A compound, is perceived as an unpleasant flavor when present at a concentration of 10 ppt or more; 2-pentylpyridine is perceived as an unpleasant flavor when present at a concentration of 10 ppt or more; 2-butyl-2-octenal is perceived as an unpleasant flavor when present at a concentration of 100 ppt or more; methylmethylthioselenide, a Group B compound, is perceived as an unpleasant flavor when present at a concentration of 1 ppt or more; dimethyldiselenide is perceived as an unpleasant flavor when present at a concentration of 1 ppt or more; and methylmethylselenyl disulfide is perceived as an unpleasant flavor when present at a concentration of 1 ppt or more. Therefore, the concentrations of 2-propyl-2-octenal, 2-pentylpyridine, 2-butyl-2-octenal, methylmethylthioselenide, and dimethyldiselenide in the present pseudo-unpleasant flavor composition can be determined by referring to the concentrations at which these compounds are perceived as unpleasant flavors.

[0031] However, when using GC to determine the compound in question in the composition for determining unpleasant flavors as a reference, the concentration of the compound in question in the composition for determining unpleasant flavors should be such that the compound is perceived as having an unpleasant flavor, based on the total mass of the composition for determining unpleasant flavors, that range from 10 ppt to 1 ppb for Group A compounds (excluding 2-butyl-2-octenal), 100 ppt to 10 ppb for Group A compounds (limited to 2-butyl-2-octenal), and 1 ppt to 100 ppt for Group B compounds. More specifically, the lower limit of the range is set to one of the following: 1 ppt (limited to group B compounds), 5 ppt (limited to group B compounds), 10 ppt (excluding 2-butyl-2-octenal), 50 ppt (excluding 2-butyl-2-octenal), 100 ppt (excluding group B compounds), 500 ppt (excluding group B compounds), 1 ppb (limited to 2-butyl-2-octenal), or 5 ppb (limited to 2-butyl-2-octenal), and the upper limit is set to 10 ppb (2-butyl-2-octenal). The concentration can be any combination of the following lower and upper limits: (limited to 2-butyl-2-octenal), 5 ppb (limited to 2-butyl-2-octenal), 1 ppb (excluding group B compounds), 500 ppt (excluding group B compounds), 100 ppt (excluding 2-butyl-2-octenal), 50 ppt (excluding 2-butyl-2-octenal), 10 ppt (limited to group B compounds), or 5 ppt (limited to group B compounds). However, depending on the flavor and type of consumer goods, an unpleasant flavor may be perceived even at concentrations below the above limits, and the concentration range for each compound is not limited to these ranges.

[0032] In this embodiment, a specific example of a consumer product containing milk protein is food and beverages containing milk protein. Food and beverages containing milk protein are food and beverages that use dairy products and other milk-based ingredients as their main raw material, and specific examples include protein supplements (so-called protein); dairy products such as cheese, yogurt, ice cream, butter, sweetened condensed milk, sweetened skim condensed milk, unsweetened condensed milk, unsweetened skim condensed milk, skim milk, concentrated milk, skim concentrated milk, buttermilk, buttermilk powder, skim milk powder, and whole milk powder; processed foods such as soups, stews, and gratins containing milk ingredients; cola drinks, fruit juices, milk drinks, whey drinks, coffee containing milk ingredients (milk coffee, café au lait, café latte, cappuccino, etc.), and various tea drinks containing milk ingredients (milk tea). Examples include functional beverages such as tea (black tea), matcha latte, matcha lattes, hojicha latte, hojicha lattes, etc., sports drinks, honey drinks, vitamin supplements, mineral supplements, energy drinks, nourishing drinks, and lactic acid bacteria drinks; non-alcoholic beverages such as alcohol-flavored beverages (beer-flavored, plum wine-flavored, chuhai-flavored, etc.); and other brewed alcoholic beverages (sparkling) or liqueurs (sparkling), such as wine, shochu, awamori, sake, beer, chuhai, cocktail drinks, sparkling wine, fruit wine, medicinal wine, and so-called "third beer," or alcoholic beverages containing these.

[0033] In this embodiment, a specific example of a food or beverage containing milk protein that may have an unpleasant taste derived from milk protein is a food or beverage containing milk protein that has undergone concentration or drying processing during the manufacturing process. Milk proteins mainly consist of whey protein and casein protein. Casein protein (also simply called casein) is the protein that precipitates when milk is adjusted to pH 4.6 at 20°C and accounts for about 80% of milk protein. Whey protein is the protein that remains in the supernatant (whey) after casein has precipitated and accounts for about 20% of milk protein.

[0034] Products containing milk protein include whey protein concentrate (WPC), whey protein isolate (WPI), milk protein concentrate (MPC), milk protein isolate (MPI), total milk protein (TMP), micellar casein isolate (MCI), micellar casein concentrate (MCC), acid casein, sodium caseinate, calcium caseinate, and rennet casein.

[0035] Here, whey protein concentrate (WPC) corresponds to "whey protein concentrate powder: a powder made by removing almost all the water from whey obtained by fermenting milk with lactic acid bacteria or by adding enzymes or acid to milk, from which lactose has been removed" as defined in Article 2, Item 12 of the "Ministerial Ordinance Concerning Standards for Ingredients of Milk and Dairy Products." Whey protein concentrate (WPC) contains whey protein, with a protein content of 15-80%. Whey protein isolate (WPI) is made by removing much of the lactose and fat from whey, increasing the protein content to 80-100%. Milk protein concentrate (MPC) and milk protein isolate (MPI) are made by separating and concentrating milk proteins by filtering skim milk. Milk protein concentrate (MPC) contains casein protein and whey protein, with a protein content of 15-80%. Milk protein isolate (MPI) contains casein protein and whey protein, with a protein content of 80-100%.

[0036] Examples of protein-containing foods and beverages derived from milk protein include protein drinks, coffee whiteners, bread, whipped cream, processed cheese, fermented milk, meat products, infant formula, beverages, liquid foods, oils and fats products, fortified foods, confectionery, infant formula, fermented milk, coffee creamer, infant formula, concentrated liquid foods, protein-fortified foods, nutritional foods, fish paste products, and fillings.

[0037] [Pseudo unpleasant flavor composition] A pseudo-unpleasant flavor composition of milk protein according to one embodiment of the present invention (hereinafter referred to as "the pseudo-unpleasant flavor composition") contains one or more compounds selected from the following group A (group A compounds). (Group A) 2-Propyl-2-octenal, 2-Pentylpyridine, 2-Butyl-2-octenal

[0038] As described above, the inventors conducted diligent research to solve the above problems and found that Group A compounds, which had not been previously detected in milk proteins, greatly contribute to the unpleasant taste derived from milk proteins. Thus, the inventors found that compositions containing Group A compounds are useful as pseudo-unpleasant taste compositions for milk proteins. Here, "pseudo-unpleasant taste composition for milk proteins" means a composition for reproducing the unpleasant taste of milk proteins (in other words, a composition for reproducing the unpleasant taste of milk proteins) (the same applies hereinafter in this specification).

[0039] Another embodiment of the present invention provides a pseudo-unpleasant flavor composition of milk protein containing one or more compounds selected from the following group B (group B compounds). (Group B) Methylmethylthioselenide, dimethyl diselenide, methylmethylselenyl disulfide

[0040] As described above, the inventors conducted diligent research to solve the above problems and discovered that Group B compounds, which had not been previously detected in milk proteins, significantly contribute to the unpleasant flavor derived from milk proteins. Thus, the inventors found that compositions containing Group B compounds are useful as pseudo-unpleasant flavor compositions for milk proteins.

[0041] As mentioned above, among the unpleasant flavors derived from milk protein (unpleasant flavors of consumer goods containing milk protein), it was found that 2-propyl-2-octenal, a group A compound, contributes to whey and mochi-like unpleasant flavors; 2-pentylpyridine contributes to earthy, roasty, and bitter unpleasant flavors; 2-butyl-2-octenal contributes to grassy, ​​metallic, and powdery unpleasant flavors; and methylmethylthioselenide, dimethyldiselenide, and methylmethylselenyl disulfide, all group B compounds, contribute significantly to animalic and vinyl-like unpleasant flavors.

[0042] In particular, it was found that combining 2-propyl-2-octenal with methylmethylthioselenide, dimethyl diselenide, or methylmethylselenyl disulfide contributes to the sticky, unpleasant flavor characteristic of whey, which is a milk protein; combining 2-pentylpyridine with methylmethylthioselenide, dimethyl diselenide, or methylmethylselenyl disulfide contributes to the earthy, unpleasant flavor characteristic of whey, which is a milk protein; and combining 2-butyl-2-octenal with methylmethylthioselenide, dimethyl diselenide, or methylmethylselenyl disulfide contributes to the grassy, ​​unpleasant flavor characteristic of milk proteins.

[0043] Therefore, the pseudo-unpleasant flavor composition of milk protein according to this embodiment is useful as a pseudo-unpleasant flavor composition of milk protein that has undergone processing such as concentration and drying, among the unpleasant flavors derived from milk protein, and is even more useful as a pseudo-unpleasant flavor composition of various proteins, and is particularly useful as a pseudo-unpleasant flavor composition of whey protein concentrate, whey protein isolate, milk protein concentrate, milk protein isolate, total milk protein, micellar casein isolate, micellar casein concentrate, acid casein, sodium caseinate, calcium caseinate, or rennet casein.

[0044] The concentration of the compound in the pseudo-unpleasant flavor composition may be set to any appropriate concentration for the purpose of qualitatively or quantitatively detecting and measuring the compound contained in the consumer goods under evaluation, comparing its intensity with that detected from the consumer goods under evaluation by GC-Olfactometry, or conducting a sensory evaluation together with the consumer goods under evaluation and assigning a score based on the compound contained in the pseudo-unpleasant flavor composition. However, when using GC to determine the concentration of the compound in the pseudo-unpleasant flavor composition based on odor detection or sensory evaluation, the concentration of the compound in the pseudo-unpleasant flavor composition should be such that the compound is perceived as having an unpleasant flavor, based on the total mass of the pseudo-unpleasant flavor composition, ranging from 10 ppt to 1 ppb for Group A compounds (excluding 2-butyl-2-octenal), 100 ppt to 10 ppb for Group A compounds (limited to 2-butyl-2-octenal), and 1 ppt to 100 ppt for Group B compounds. More specifically, the lower limit of the range is set to one of the following: 1 ppt (limited to group B compounds), 5 ppt (limited to group B compounds), 10 ppt (excluding 2-butyl-2-octenal), 50 ppt (excluding 2-butyl-2-octenal), 100 ppt (excluding group B compounds), 500 ppt (excluding group B compounds), 1 ppb (limited to 2-butyl-2-octenal), or 5 ppb (limited to 2-butyl-2-octenal), and the upper limit is set to 10 ppb (2-butyl-2-octenal). The concentration can be any combination of the following lower and upper limits: (limited to 2-butyl-2-octenal), 5 ppb (limited to 2-butyl-2-octenal), 1 ppb (excluding group B compounds), 500 ppt (excluding group B compounds), 100 ppt (excluding 2-butyl-2-octenal), 50 ppt (excluding 2-butyl-2-octenal), 10 ppt (limited to group B compounds), or 5 ppt (limited to group B compounds). However, depending on the flavor and type of consumer goods, an unpleasant flavor may be perceived even at concentrations below the above limits, and the concentration range for each compound is not limited to these ranges.

[0045] If the pseudo-unpleasant flavor composition contains only one of the compounds in question, the effect on the compound (1 type) contained in the pseudo-unpleasant flavor composition can be accurately confirmed when used to search for masking compounds that mask the unpleasant flavor of milk protein, or when used to confirm the effect of known masking compounds for the unpleasant flavor of milk protein. Furthermore, if the pseudo-unpleasant flavor composition contains two or more of the Group A compounds (and preferably in preferred concentration ratios of each compound), or even more, if it contains one or more of the Group A compounds (and preferably in preferred concentration ratios of each compound) and one or more of the Group B compounds (and preferably in preferred concentration ratios of each compound), then when searching for or confirming the aforementioned masking compounds, a pseudo-unpleasant flavor closer to the actual unpleasant flavor of milk protein can be reproduced, and the verification of the masking effect can be confirmed with less effort.

[0046] The pseudo-unpleasant flavor composition in question may contain, in addition to the compound in question, known substances that cause unpleasant flavors derived from milk proteins. Examples of known substances that cause unpleasant flavors derived from milk proteins include, but are not limited to, p-cresol, indole, skatole, 2-aminoacetophenone, dimethyl disulfide, dimethyl trisulfide, 1-octen-3-one, trans-2-nonenal, 2,4-decadienal, 2,4-nonadienal, trans-6-nonenal, and methional.

[0047] In addition to the various components mentioned above, this pseudo-unpleasant flavor composition may also contain consumer goods containing milk protein or components contained in such consumer goods.

[0048] [Method for evaluating unpleasant flavors of consumer goods] A method for determining unpleasant flavors of consumer goods containing milk protein according to one embodiment of the present invention (hereinafter sometimes referred to as "the present unpleasant flavor determination method") uses one or more compounds selected from the following group A as indicators. (Group A) 2-Propyl-2-octenal, 2-Pentylpyridine, 2-Butyl-2-octenal

[0049] As mentioned above, Group A compounds contribute very significantly to the unpleasant flavor of milk proteins. Therefore, by using Group A compounds as an indicator, the unpleasant flavor of consumer goods containing milk proteins can be accurately determined.

[0050] Another embodiment of the present invention provides a method for determining unpleasant flavors of consumer goods containing milk protein, using one or more compounds selected from the following group B as indicators. (Group B) Methylmethylthioselenide, dimethyl diselenide, methylmethylselenyl disulfide

[0051] As mentioned above, since group B compounds contribute very significantly to the unpleasant taste of milk proteins, using group B compounds as an indicator allows for accurate determination of the unpleasant taste of consumer goods containing milk proteins.

[0052] In this method for determining unpleasant flavors, the step of quantifying the compound in question is not essential; it is sufficient if the compound can be detected by any method. For example, when using GC, one method is to pre-measure the retention time of the compound in question and then analyze the consumer product to be evaluated to detect the compound (such as the internal standard method or standard addition method), or to have well-trained panelists detect the compound by GC-O. Another method is to have well-trained panelists perform a sensory evaluation of the consumer product to be evaluated to detect the compound in question.

[0053] Furthermore, in the method for determining unpleasant flavors, when multiple compounds are detected, the order of detection is not important, and each compound may be detected simultaneously or together in a single measurement.

[0054] In this method for determining unpleasant flavors, the compound in question can be used alone, or it can be combined with other components, such as solvents for dissolution or dilution, stabilizers, antioxidants, fragrances, plant extracts, and other additives, to prepare a composition suitable for practical use, such as for storage or in testing.

[0055] [Method for evaluating unpleasant flavors of consumer goods] A method for evaluating unpleasant flavors of consumer goods containing milk protein according to one embodiment of the present invention (hereinafter sometimes referred to as "the present unpleasant flavor evaluation method") includes the following steps. (a) A step of quantifying one or more compounds selected from the following group A in the consumer goods. (Group A) 2-Propyl-2-octenal, 2-Pentylpyridine, 2-Butyl-2-octenal

[0056] As mentioned above, Group A compounds contribute very significantly to the unpleasant flavor of milk proteins. Therefore, by using Group A compounds as an indicator and quantifying Group A compounds in consumer goods, the unpleasant flavor of consumer goods containing milk proteins can be evaluated with high accuracy.

[0057] Another embodiment of the present invention, a method for evaluating unpleasant flavors of consumer goods containing milk protein (hereinafter sometimes referred to as "the present unpleasant flavor evaluation method"), includes the following steps. (a) A step of quantifying one or more compounds selected from the following group B in the consumer goods. (Group B) Methylmethylthioselenide, dimethyl diselenide, methylmethylselenyl disulfide

[0058] As mentioned above, since group B compounds contribute very significantly to the unpleasant taste of milk protein, by using group B compounds as an indicator and quantifying group A compounds in consumer goods, the unpleasant taste of consumer goods containing milk protein can be evaluated with high accuracy.

[0059] In this unpleasant flavor evaluation method, the method for quantifying the compound in question is arbitrary. For example, when measuring by GC-MS, a calibration curve can be created using the compound in question as a standard, and the peak of the compound in question contained in the consumer product can be identified using that calibration curve, and its amount can be measured. Alternatively, when using sensory evaluation as the method for quantifying the compound in question, unpleasant flavor standard samples can be prepared by diluting the compound in question in several stages, and the odor of the evaluation sample prepared from the consumer product can be compared with the standard sample to determine the amount of the compound in question contained in the consumer product by sensory evaluation. As described above, in this unpleasant flavor evaluation method, a highly objective quantitative determination is possible whether the compound in question is quantified by instrumental analysis or sensory evaluation.

[0060] Furthermore, in this unpleasant flavor evaluation method, when quantifying multiple compounds, the order of quantification is not important, and each compound may be quantified simultaneously or collectively in a single measurement.

[0061] In methods for evaluating unpleasant flavors of consumer goods, the compound in question can be used alone, or it can be combined with other components, such as solvents for dissolution or dilution, or additives such as stabilizers, antioxidants, fragrances, or plant extracts, to prepare a composition suitable for practical use in storage or judgment tests.

[0062] [Method for producing a composition that improves unpleasant flavors derived from milk protein] A method for producing a milk protein-derived composition for improving unpleasant flavors according to one embodiment of the present invention (hereinafter sometimes referred to as "the method for producing the unpleasant flavor-improving composition") includes the following steps. (b) A step of preparing a pseudo-unpleasant flavor composition of milk protein containing one or two compounds selected from the group consisting of Group A or Group B below, (c) A step of preparing multiple candidate compositions for masking unpleasant flavors derived from milk protein, (d) A step of adding the candidate compositions for masking unpleasant flavors to the pseudo-unpleasant flavor composition and evaluating the unpleasant flavor of the pseudo-unpleasant flavor composition after the additions, (e) From among the candidate compositions for masking unpleasant flavors prepared in step (c), the one that yielded the best evaluation result obtained in step (d) is selected as the milk protein-derived unpleasant flavor improving composition.

[0063] In the method for producing the unpleasant flavor-improving composition, the candidate substances for masking unpleasant flavors derived from milk protein include both known unpleasant flavor-masking compounds derived from milk protein and compounds whose unpleasant flavor-masking effect on milk protein-derived unpleasant flavors is unknown, and which are compounds for which the masking effect on milk protein-derived unpleasant flavors is to be confirmed. In the method for producing the unpleasant flavor-improving composition, the masking effect of the candidate composition for masking unpleasant flavors derived from milk protein, prepared in step (c), on the milk protein-derived unpleasant flavor-causing substances can be confirmed by the pseudo-unpleasant flavor composition of milk protein prepared in step (b).

[0064] The present method for producing an unpleasant flavor-improving composition allows for the confirmation of the effectiveness of known unpleasant flavor-masking compounds derived from milk proteins, as well as the search for new unpleasant flavor-masking compounds derived from milk proteins, and ultimately the production of a novel unpleasant flavor-improving composition derived from milk proteins. [Examples]

[0065] The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to these examples.

[0066] [Example 1] Confirmation of unpleasant flavor-causing substances derived from milk protein [Example 1-1] Preparation of food and beverages containing milk protein As a food and beverage containing milk protein, Reference Sample 1 was prepared by diluting a commercially available whey protein concentrate (containing 80% whey protein as milk protein) with water until the milk protein concentration reached 1%.

[0067] Similarly, as a food and beverage containing milk protein, a commercially available whey protein concentrate (containing 80% whey protein as milk protein, different from Reference Sample 1) was diluted with water to a milk protein concentration of 1%, and this was designated as Reference Sample 2.

[0068] Similarly, as a food and beverage containing milk protein, Reference Sample 3 was prepared by diluting a commercially available whey protein isolate (containing 90% whey protein as milk protein) with water until the milk protein concentration reached 1%.

[0069] Similarly, as a food and beverage containing milk protein, Reference Sample 4 was prepared by diluting a commercially available milk protein concentrate (containing 80% milk protein, with a casein protein to whey protein ratio of 8:2) with water until the milk protein concentration reached 1%.

[0070] Similarly, as a food and beverage containing milk protein, Reference Sample 5 was prepared by diluting a commercially available milk protein isolate (containing 80% milk protein, with a casein protein to whey protein ratio of 8:2) with water until the milk protein concentration reached 1%.

[0071] [Examples 1-2] Confirmation of unpleasant flavor-causing substances derived from milk protein For reference samples 1-5 prepared in Example 1-1, aroma capture was performed using the SBSE (Stir Bar Sorptive Extraction) method with an adsorbent (Twister / Gerstel). After aroma capture, the adsorbent was subjected to GC-MS / Olfactometry to separate the aroma components using a thermal desorption apparatus (TDU / Gerstel). Among the aroma components separated by GC-MS / Olfactometry, a portion that caused an unpleasant taste was found in reference samples 1-5 by odor detection. This component was identified as 2-propyl-2-octenal, methylmethylthioselenide, dimethyldiselenide, methylmethylselenyl disulfide, 2-pentylpyridine, and 2-butyl-2-octenal, and these were confirmed to be substances causing the unpleasant taste derived from milk protein.

[0072] [Example 2] Preparation of a composition for determining unpleasant flavors derived from milk protein (a pseudo-unpleasant flavor composition of milk protein) [Example 2-1] Confirmation of the contribution of an unpleasant flavor-causing substance to the unpleasant flavor (1) In order to confirm the contribution of each compound used as an unpleasant flavor-causing substance derived from milk protein in Examples 1-2 to the unpleasant flavor, 2-propyl-2-octenal, methylmethylthioselenide, dimethyldiselenide, methylmethylselenyl disulfide, 2-pentylpyridine, and 2-butyl-2-octenal were added to water to the concentrations shown in Table 1 below, and compositions of products 1 to 18 of the present invention were prepared.

[0073] The compositions of the Inventive Products 1 to 18 obtained were subjected to sensory evaluation by 15 well-trained panelists (with more than 10 years of experience). The sensory evaluation was conducted by having the panelists comment on the differences in flavor when comparing Inventive Products 1 to 18 with water without the above compounds added as a control, and by averaging the scores that the panelists gave to the unpleasant flavor intensity compared to the control, according to the evaluation criteria below. <Evaluation Criteria for Unpleasant Flavor Intensity> Compared to the control product, the unpleasant taste characteristic of milk protein is significantly noticeable: 5 Compared to the control product, the unpleasant taste characteristic of milk protein is clearly noticeable: 4 Compared to the control product, a slight unpleasant taste characteristic of milk protein is noticeable: 3 Compared to the control product, a very slight unpleasant taste characteristic of milk protein is noticeable: 2 Equivalent to the control product (no unpleasant taste characteristic of milk protein): 1

[0074] The results of the sensory evaluation are shown in Table 1 below.

[0075] [Table 1]

[0076] As shown in Table 1, according to products 1 to 18 of the present invention, 2-propyl-2-octenal is perceived as an unpleasant flavor when present at a concentration of 10 ppt or more, 2-pentylpyridine is perceived as an unpleasant flavor when present at a concentration of 10 ppt or more, 2-butyl-2-octenal is perceived as an unpleasant flavor when present at a concentration of 100 ppt or more, methylmethylthioselenide is perceived as an unpleasant flavor when present at a concentration of 1 ppt or more, dimethyldiselenide is perceived as an unpleasant flavor when present at a concentration of 1 ppt or more, and methylmethylselenyl disulfide is perceived as an unpleasant flavor when present at a concentration of 1 ppt or more.

[0077] Based on the above, it was found that compositions containing 2-propyl-2-octenal, 2-pentylpyridine, 2-butyl-2-octenal, methylmethylthioselenide, dimethyldiselenide, and methylmethylselenyl disulfide are useful as compositions for determining unpleasant flavors derived from milk proteins, and as compositions for simulating unpleasant flavors of milk proteins.

[0078] [Example 2-2] Confirmation of the contribution of an unpleasant flavor-causing substance to the unpleasant flavor (2) In order to confirm the contribution to unpleasant flavor when each compound used in combination as an unpleasant flavor-causing substance derived from milk protein in Examples 1-2, compositions of products 19-45 of the present invention were prepared by adding 2-propyl-2-octenal, 2-pentylpyridine, and 2-butyl-2-octenal as additive compound 1 (group A compounds) and methylmethylthioselenide, dimethyldiselenide, and methylmethylselenyl disulfide as additive compound 2 (group B compounds) to water so that the concentrations in the water were as shown in Table 2 below.

[0079] The compositions 19-45 of the present invention were subjected to sensory evaluation by 15 well-trained panelists (with more than 10 years of experience). The sensory evaluation was conducted by having the panelists comment on the differences in flavor when comparing water without the above compounds to the control product, and by averaging the scores given by the panelists to the intensity of unpleasant flavors compared to the control product according to the evaluation criteria below. <Evaluation Criteria for Unpleasant Flavor Intensity> Compared to the control product, the unpleasant taste characteristic of milk protein is significantly noticeable: 5 Compared to the control product, the unpleasant taste characteristic of milk protein is clearly noticeable: 4 Compared to the control product, a slight unpleasant taste characteristic of milk protein is noticeable: 3 Compared to the control product, a very slight unpleasant taste characteristic of milk protein is noticeable: 2 Equivalent to the control product (no unpleasant taste characteristic of milk protein): 1

[0080] The results of the sensory evaluation are shown in Table 2 below.

[0081] [Table 2]

[0082] As shown in Table 2, according to products 19-45 of the present invention, it was found that using any of the Group A compounds (2-propyl-2-octenal, 2-pentylpyridine, 2-butyl-2-octenal) in combination with any of the Group B compounds (methylmethylthioselenide, dimethyldiselenide, methylmethylselenyl disulfide) resulted in a greater contribution to the unpleasant flavor characteristic of milk proteins compared to using each compound alone. In other words, by combining one or more Group A compounds with one or more Group B compounds, the characteristic aroma features of milk proteins, such as the mochi-like, earthy, and grassy flavors of whey, were more pronounced, resulting in a more distinguishable and distinctive flavor compared to using each compound alone.

Claims

1. A composition for determining unpleasant flavors derived from milk protein, containing one or more compounds selected from group A or group B below. (Group A) 2-propyl-2-octenal, 2-pentylpyridine, 2-butyl-2-octenal (Group B) Methylmethylthioselenide, dimethyl diselenide, methylmethylselenyl disulfide

2. A composition for determining unpleasant flavors of consumer goods containing milk protein, comprising one or more compounds selected from Group A or Group B below. (Group A) 2-propyl-2-octenal, 2-pentylpyridine, 2-butyl-2-octenal (Group B) Methylmethylthioselenide, dimethyl diselenide, methylmethylselenyl disulfide

3. A pseudo-unpleasant flavor composition of milk protein containing one or more compounds selected from group A or group B below. (Group A) 2-propyl-2-octenal, 2-pentylpyridine, 2-butyl-2-octenal (Group B) Methylmethylthioselenide, dimethyl diselenide, methylmethylselenyl disulfide

4. A method for determining unpleasant flavors of consumer goods containing milk protein, using one or more compounds selected from Group A or Group B below as indicators. (Group A) 2-propyl-2-octenal, 2-pentylpyridine, 2-butyl-2-octenal (Group B) Methylmethylthioselenide, dimethyl diselenide, methylmethylselenyl disulfide

5. A method for evaluating unpleasant flavors of consumer goods containing milk protein, (a) A step of quantifying one or more compounds selected from the following group A or group B in the consumer goods, A method for evaluating unpleasant flavors of consumer goods containing milk protein, including milk protein. (Group A) 2-propyl-2-octenal, 2-pentylpyridine, 2-butyl-2-octenal (Group B) Methylmethylthioselenide, dimethyl diselenide, methylmethylselenyl disulfide

6. (b) A step of preparing a pseudo-unpleasant flavor composition of milk protein containing one or two compounds selected from the group consisting of group A or group B below, (c) A step of preparing multiple candidate compositions for masking unpleasant flavors derived from milk protein, (d) A step of adding the candidate compositions for masking unpleasant flavors to the pseudo-unpleasant flavor composition and evaluating the unpleasant flavor of the pseudo-unpleasant flavor composition after the addition. (e) From among the candidate compositions for masking unpleasant flavors prepared in step (c), select the one that yielded the best evaluation result in step (d) and use it as a composition for improving unpleasant flavors derived from milk protein. A method for producing a composition for improving unpleasant flavors derived from milk protein, which includes the composition. (Group A) 2-propyl-2-octenal, 2-pentylpyridine, 2-butyl-2-octenal (Group B) Methylmethylthioselenide, dimethyl diselenide, methylmethylselenyl disulfide

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