Novel sucrose fatty acid esters

Abstract

The present invention provides a sucrose fatty acid ester having reduced bitterness and in which umami is easily perceived, and a food or the like using the sucrose fatty acid ester. A sucrose fatty acid ester characterized in that the content of palmitostearate in diesters contained in the sucrose fatty acid ester is relatively low. Specifically, the sucrose fatty acid ester is a sucrose fatty acid ester in which a part of the hydroxyl groups of sucrose is substituted with an aliphatic hydrocarbon group, and satisfies all of (1) to (3) below: (1) contains palmitopalmitate and stearostearate, (2) the content of palmitostearate is lower than the content of palmitopalmitate, and (3) the content of palmitostearate is lower than the content of stearostearate.

Description

Technical Field

[0001] This invention relates to novel sucrose fatty acid esters. Specifically, it relates to a sucrose fatty acid ester characterized in that the diester contained in the sucrose fatty acid ester contains a relatively low level of palmitic stearate. Background Technology

[0002] Sucrose fatty acid esters are compounds in which at least some of the eight hydroxyl groups in the sucrose molecular backbone are esterified with fatty acid hydrocarbon groups. Sucrose fatty acid esters include various ester bodies, ranging from monovalent to polyvalent, such as monoesters, diesters, and trimers.

[0003] It has been reported that when using sucrose fatty acid esters with specific ester compositions as emulsifiers in oil-in-water emulsion compositions, the viscosity of the composition can be increased (Patent Document 1). Furthermore, it has been reported that emulsion stability can be improved by controlling the molar ratio of sucrose fatty acid diesters to higher aliphatic alcohols and / or higher fatty acids (Patent Document 2).

[0004] Sucrose fatty acid esters with low substitution degree have high hydrophilicity and are used in the food emulsifier market as emulsifier stabilizers for oil-in-water (O / W) emulsions such as milk and coffee. However, there is a problem that the bitter taste from the emulsifier is easily perceived, making it difficult to perceive the umami flavor in the food.

[0005] To reduce the bitterness of sucrose fatty acid esters, methods have been reported to reduce the necessary amount of sucrose fatty acid esters in food by increasing the purity of the palmitate ester, and methods for manufacturing sucrose fatty acid esters by microwave irradiation. However, the problem that sucrose fatty acid esters with high palmitate purity and sucrose fatty acid esters manufactured by microwave irradiation tend to cause emulsification instability when incorporated into beverages, thus making it difficult to perceive the umami flavor in foods containing sucrose fatty acid esters, has not been fully resolved (see Patent Documents 3, 4, and 5).

[0006] Existing technical documents

[0007] Patent documents

[0008] Patent Document 1: Japanese Patent Application Publication No. 2009-214079

[0009] Patent Document 2: Japanese Patent Application Publication No. 8-268877

[0010] Patent Document 3: Japanese Patent Application Publication No. 2023-047770

[0011] Patent Document 4: WO 2017 / 013966

[0012] Patent Document 5: WO 19 / 235619 Summary of the Invention

[0013] The problem that the invention aims to solve

[0014] The main objective of this invention is to provide sucrose fatty acid esters with reduced bitterness and easily perceptible umami flavor, as well as foods using the aforementioned sucrose fatty acid esters.

[0015] Methods for solving problems

[0016] The inventors discovered that by making the proportion of palmitic stearate lower than that of palmitate palmitate and stearate stearate in the diester contained in sucrose fatty acid esters, the above-mentioned problem can be solved.

[0017] That is, the present invention provides the following [1] to [6]. It should be noted that, unless otherwise specified, "%" in this specification refers to "weight %".

[0018] [1] A sucrose fatty acid ester, wherein at least a portion of the hydroxyl groups of sucrose are replaced by aliphatic hydrocarbon groups, and satisfies all of the following (1) to (3):

[0019] (1) Contains sucrose palmitate and sucrose stearate.

[0020] (2) The content of sucrose palmitate stearate is below the content of sucrose palmitate stearate.

[0021] (3) The content of sucrose palmitic stearate is below that of sucrose stearate.

[0022] [2] According to the sucrose fatty acid ester described in [1], wherein the sucrose palmitic stearate is less than 31% of the total diester.

[0023] [3] According to [1] or [2], the proportion of monoesters to the total amount of esters is 50 to 90%, and the proportion of diesters to the total amount of esters is 5 to 45%.

[0024] [4] The sucrose fatty acid ester according to any one of [1] to [3], wherein the sucrose palmitate stearate accounts for 10% or more and 31% or less of the total diester.

[0025] [5] The sucrose fatty acid ester according to any one of [1] to [4], wherein the sucrose stearate is 15 to 35% of the total amount of diester.

[0026] [6] The sucrose fatty acid ester according to any one of [1] to [5], wherein the sucrose palmitate palmitate is 50% to 90% of the total diester.

[0027] [7] A sucrose fatty acid ester, wherein at least a portion of the hydroxyl groups of sucrose are replaced by aliphatic hydrocarbon groups, satisfying the following (1) and (2):

[0028] (1) Contains sucrose palmitate and sucrose stearate.

[0029] (2) The sucrose palmitate stearate content is less than 31% of the total diester.

[0030] [8] According to the sucrose fatty acid ester described in [7], wherein the proportion of monoesters to the total amount of esters is 50-90% and the proportion of diesters to the total amount of esters is 5-45%.

[0031] [9] The sucrose fatty acid ester according to [7] or [8], wherein the sucrose palmitate stearate is 10% or more and 31% or less relative to the total diester.

[0032]

[10] The sucrose fatty acid ester according to any one of [7] to [9], wherein the sucrose stearate is 15 to 35% of the total amount of diester.

[0033]

[11] The sucrose fatty acid ester according to any one of [7] to

[10] , wherein the sucrose palmitate palmitate is 50% to 90% of the total diester.

[0034]

[12] A food containing any one of the sucrose fatty acid esters described in [1] to

[11] .

[0035]

[13] A beverage containing any one of the sucrose fatty acid esters described in [1] to

[11] .

[0036]

[14] The beverage according to

[13] further comprises one or more stabilizers selected from organic monoglycerides and sodium caseinate.

[0037] This specification contains the disclosure of Japanese Patent Application No. 2024-060604, which forms the basis of the priority claim of this application.

[0038] Invention Effects

[0039] Compared to conventional sucrose fatty acid esters, the sucrose fatty acid esters of the present invention exhibit reduced bitterness and increased umami flavor when incorporated into food. Therefore, the sucrose fatty acid esters of the present invention are useful as emulsifiers in beverages and the like. Detailed Implementation

[0040] 1. The sucrose fatty acid ester of the present invention

[0041] Sucrose fatty acid esters are compounds in which at least a portion of the eight hydroxyl groups in the sucrose molecular backbone are esterified with fatty acid hydrocarbon groups. In other words, sucrose fatty acid esters refer to compounds having a structure in which at least a portion of the eight hydroxyl groups in the sucrose molecular backbone are replaced by fatty acids through esterification. Further, sucrose fatty acid esters have a structure in which at least a portion of the hydroxyl groups present in sucrose are esterified with fatty acids containing aliphatic hydrocarbon groups. The ester bodies contained in sucrose fatty acid esters can be classified into monoesters (degree of esterification 1), diesters (degree of esterification 2), and polyesters (degree of esterification 3 or higher) according to their degree of esterification.

[0042] The sucrose fatty acid esters of this invention are sucrose fatty acid esters containing palmitic acid and stearic acid as constituent fatty acids. As diesters, they can be divided into sucrose palmitate (hereinafter sometimes simply referred to as palmitate palmitate), formed by ester bonding of two palmitic acids with sucrose; sucrose stearate (hereinafter sometimes simply referred to as stearate stearate), formed by ester bonding of two stearic acids with sucrose; and sucrose palmitate stearate (hereinafter sometimes simply referred to as palmitate stearate), formed by ester bonding of palmitic acid and stearic acid one by one. It should be noted that sucrose has eight hydroxyl groups in its molecular backbone. Depending on which hydroxyl group in the sucrose molecular backbone the two fatty acids form an ester bond, there are multiple diester isomers. However, it is considered that the functional differences between isomers caused by the bonding sites of the diester are very small. Therefore, in this invention, isomers caused by the bonding sites of the diester are not distinguished.

[0043] The sucrose fatty acid ester of the present invention is characterized in that it contains at least palmitate palmitate and stearate stearate as diesters, and the content of palmitate stearate in the sucrose fatty acid ester is lower than the content of either palmitate palmitate or stearate stearate.

[0044] In the first embodiment, the sucrose fatty acid ester of the present invention satisfies all of the following (1) to (3).

[0045] (1) Contains palmitate palmitate and stearate stearate.

[0046] (2) The content of palmitic stearate is below the content of palmitic palmitate.

[0047] (3) The content of palmitic stearate is below the content of stearic acid stearate.

[0048] It is believed that by including palmitic palmitate and stearic acid stearate, the emulsifying properties are superior compared to each alone. Moreover, it is believed that by (2) having a palmitic acid stearate content of less than that of palmitic palmitate and (3) having a palmitic acid stearate content of less than that of stearic acid stearate, sucrose fatty acid esters with reduced bitterness and easily perceptible umami flavor can be produced.

[0049] In the first embodiment, palmitic palmitate is preferably 5% to 99% of the total diester, more preferably 20% to 99%, further preferably 40% to 95%, particularly preferably 50% to 90%, and most preferably 65% ​​to 85%.

[0050] In the first embodiment, the stearic acid stearate is preferably 5% to 99% of the total diester, more preferably 5% to 60%, further preferably 5% to 40%, particularly preferably 10% to 35%, and most preferably 15% to 35%.

[0051] The phrase “content below” in (2) and (3) above also includes cases where the content of palmitic stearate is “0”.

[0052] In the first embodiment, the content of palmitic stearate is preferably 31% or less relative to the total diester. From the viewpoint of good emulsification stability when compounded in food, the content of palmitic stearate is preferably 21% or less, more preferably 15% or less, further preferably 8% or less, particularly preferably 4% or less, and most preferably 1% or less. Furthermore, from the viewpoint of reducing bitterness and increasing umami when compounded in food, the content of palmitic stearate is preferably 2% or more, more preferably 5% or more, further preferably 10% or more, particularly preferably 12% or more, even more preferably 15% or more, and most preferably 18% or more.

[0053] In the second embodiment, the sucrose fatty acid ester of the present invention satisfies the following (1) and (2).

[0054] (1) Contains palmitate palmitate and stearate stearate.

[0055] (2) The palmitic stearate content is less than 31% of the total diester.

[0056] It is believed that by including palmitic palmitate and stearic acid stearate, the emulsifying properties are superior compared to each alone. Moreover, it is believed that by keeping the palmitic stearate content below 31% relative to the total diester, a sucrose fatty acid ester with reduced bitterness and easily perceptible umami flavor can be produced.

[0057] In the second embodiment, palmitic palmitate is preferably 5% to 99% of the total diester, more preferably 20% to 99%, further preferably 40% to 95%, particularly preferably 50% to 90%, and most preferably 65% ​​to 85%.

[0058] In the second embodiment, the stearic acid stearate is preferably 5% to 99% of the total diester, more preferably 5% to 60%, further preferably 5% to 40%, particularly preferably 10% to 35%, and most preferably 15% to 35%.

[0059] In the second embodiment, from the viewpoint of good emulsification stability when compounded in food, stearate palmitate is preferably 21% or less, more preferably 15% or less, further preferably 8% or less, particularly preferably 4% or less, and most preferably 1% or less. Furthermore, from the viewpoint of reducing bitterness and increasing umami when compounded in food, stearate palmitate is preferably 2% or more, more preferably 5% or more, further preferably 10% or more, particularly preferably 12% or more, even more preferably 15% or more, and most preferably 18% or more.

[0060] In the first and second embodiments (hereinafter the same), the ratio of palmitic palmitate to stearic acid in the diester of the sucrose fatty acid ester of the present invention is preferably 0.1 to 3 parts by weight of stearic acid relative to 1 part by weight of palmitic palmitate, more preferably 0.1 to 0.8 parts by weight, further preferably 0.15 to 0.6 parts by weight, and particularly preferably 0.15 to 0.3 parts by weight. If the ratio of palmitic palmitate to stearic acid is within the above range, it results in an excellent flavor in food and can exert a high emulsifying function.

[0061] In the sucrose fatty acid esters of the present invention, the ratio of palmitic acid ester to stearic acid ester is preferably 0.1 to 3 parts by weight of stearic acid ester, more preferably 0.1 to 0.8 parts by weight, further preferably 0.2 to 0.6 parts by weight, and particularly preferably 0.25 to 0.5 parts by weight, relative to 1 part by weight of palmitic acid ester. When the ratio of palmitic acid ester to stearic acid ester is within the above range, it can exert excellent antibacterial function in food.

[0062] In the sucrose fatty acid esters of the present invention, the proportions of monoesters and diesters relative to the total ester content are preferably 50% to 90% and 5% to 45%, more preferably 60% to 90% and 10% to 40%, further preferably 63% to 85% and 15% to 35%, particularly preferably 65% ​​to 80% and 20% to 30%, and most preferably 70% to 78% and 20% to 27%. If the ratio of monoesters to diesters is within the above range, it can exert excellent effects in dispersing, emulsifying, stabilizing, and antibacterial functions in food.

[0063] In the sucrose fatty acid ester of the present invention, the total amount of monoesters and diesters relative to the total amount of esters is preferably 60% or more, more preferably 70% or more, further preferably 80% or more, particularly preferably 90% or more, and most preferably 95% or more.

[0064] By defining this range, high dispersibility can be maintained when used in foods containing a large amount of moisture.

[0065] The sucrose fatty acid esters of the present invention may also have aliphatic hydrocarbon groups other than palmitic acid and stearic acid. To obtain an oil-in-water emulsion with high emulsification stability, the aforementioned aliphatic hydrocarbon groups are preferably saturated hydrocarbon groups. Furthermore, chain hydrocarbon groups are preferred, and straight-chain hydrocarbon groups are more preferred.

[0066] From the perspectives of hydrophilicity, dispersibility in water, and emulsification stability in oil-in-water emulsifiers, aliphatic hydrocarbon groups preferably have a higher number of carbon atoms. Specifically, from the perspective of emulsification stability, the aliphatic hydrocarbon groups preferably have 12 or more carbon atoms, more preferably 14 or more, and even more preferably 16 or more.

[0067] Specifically, the sucrose fatty acid esters of the present invention may contain hydrocarbon groups derived from oleic acid, myristic acid, lauric acid, and behenic acid, in addition to palmitic acid and stearic acid. From the viewpoint of having excellent flavor and antibacterial properties, the hydrocarbon groups derived from oleic acid, myristic acid, lauric acid, and behenic acid in the sucrose fatty acid esters of the present invention are preferably less than 1% of all aliphatic hydrocarbon groups, more preferably less than 0.5%, and even more preferably none.

[0068] The types of aliphatic hydrocarbon groups in the sucrose fatty acid esters of the present invention and their proportions relative to the total amount of aliphatic hydrocarbon groups can be identified by high performance liquid chromatography, as shown in the following example.

[0069] • Device: Thermo Fisher U3000 series

[0070] • Column: Inertsil C8 4.6×150mm, 5μm

[0071] Column temperature: 40℃

[0072] • Eluent: Eluent A (water) B (methanol / THF 9 / 1)

[0073] ·A / B=30 / 70(0)=>20 / 80(20)=>0 / 100(35)=>0 / 100(50)=>30 / 70(53)=>30 / 70(60)

[0074] When using the above-mentioned high performance liquid chromatography method, the diesters contained in the sucrose fatty acid esters of the present invention have a retention time of 35.9 minutes for palmitic stearate, a retention time of 35 minutes for palmitic palmitate, and a retention time of 36.7 minutes for stearic acid stearate.

[0075] The form of sucrose fatty acid esters is not particularly limited; for example, they can be in powder or flake form. The powder or flakes are dissolved in tetrahydrofuran, and as described above, high-performance liquid chromatography (HPLC) can be used to analyze the types of aliphatic hydrocarbon groups present in the sucrose fatty acid esters and their proportion relative to the total amount of aliphatic hydrocarbon groups.

[0076] For beverages containing sucrose fatty acid esters, as described later, the types of aliphatic hydrocarbon groups and their proportions relative to the total amount of aliphatic hydrocarbon groups in the sucrose fatty acid esters can also be analyzed using high-performance liquid chromatography (HPLC). For example, by adding ethyl acetate to a beverage sample, mixing, recovering the solvent phase, removing the solvent using an evaporator, and purifying the sucrose fatty acid esters from the beverage, as described above, the types of aliphatic hydrocarbon groups and their proportions relative to the total amount of aliphatic hydrocarbon groups in the sucrose fatty acid esters can be analyzed using HPLC.

[0077] In the general analytical method of gas chromatography for sucrose fatty acid esters, the peak sensitivity of sucrose fatty acid diesters is low, making them difficult to detect and quantify.

[0078] The sucrose fatty acid esters of the present invention can be manufactured by mixing one or more of the following reactants and purified products obtained by purifying these reactants using chromatography or the like. These reactants are obtained through esterification of sucrose with fatty acids, or esterification of sucrose-based fatty acyl chlorides or fatty acid anhydrides, transesterification of sucrose with lower ester compounds of fatty acids, enzyme-based reactions, or microwave irradiation of a mixture containing fatty acid esters and fatty acids. Low-substituted sucrose fatty acid esters can be manufactured by adjusting the ratio of fatty acid methyl esters to sucrose in the above manufacturing process.

[0079] As a method for manufacturing a sucrose fatty acid ester as described in the first embodiment, comprising (1) palmitate and stearate, (2) having a palmitate stearate content of less than or equal to the content of palmitate, and (3) having a palmitate stearate content of less than or equal to the content of stearate, for example, it can be manufactured by mixing sucrose stearate with sucrose palmitate. The sucrose stearate is prepared by reacting methyl stearate containing more than 99% stearic acid of the fatty acids in all esters with sucrose, and the sucrose palmitate is prepared by reacting sucrose with methyl palmitate containing more than 99% palmitic acid of the fatty acids in all esters. In addition, by further mixing with substances prepared by reacting methyl stearate and methyl palmitate with sucrose (including palmitate, stearate, and palmitate stearate), it is possible to include palmitate stearate. By adjusting the mixing ratio, the ratio of palmitate palmitate, stearate stearate, and palmitate stearate can be adjusted. Sucrose fatty acid esters prepared by reacting methyl stearate and methyl palmitate with sucrose generally have a higher content of palmitate stearate, in addition to improving the selectivity of the reaction (e.g., manufacturing example 1, manufacturing example 2).

[0080] As a method for manufacturing a sucrose fatty acid ester containing (1) palmitate and stearate, and (2) palmitate stearate having a content of 31% or less relative to the total diester, as in the second embodiment, it can be manufactured, for example, by mixing sucrose stearate with sucrose palmitate, wherein the sucrose stearate is prepared by reacting methyl stearate containing 99% or more of the stearic acid in the fatty acids of the entire ester with sucrose, and the sucrose palmitate is prepared by reacting sucrose with methyl palmitate containing 99% or more of the palmitic acid in the fatty acids of the entire ester. Furthermore, by further mixing with substances prepared by reacting methyl stearate and methyl palmitate with sucrose (including palmitate palmitate, stearate stearate, and palmitate stearate), it is possible to include palmitate stearate, and the ratio of palmitate palmitate, stearate stearate, and palmitate stearate can be adjusted by adjusting the mixing ratio. Sucrose fatty acid esters prepared by reacting methyl stearate and methyl palmitate with sucrose generally have a higher content of palmitate stearate, in addition to improving the selectivity of the reaction (e.g., manufacturing example 1, manufacturing example 2).

[0081] The sucrose fatty acid esters of the present invention can be used as emulsifying stabilizers (emulsifiers), lubricants, etc. The sucrose fatty acid esters of the present invention exhibit excellent oil-in-water emulsification properties when dispersed in water, and are therefore particularly suitable for use as oil-in-water (O / W) emulsifying stabilizers.

[0082] The sucrose fatty acid esters of the present invention, as oil-in-water (O / W) emulsion stabilizers, exhibit excellent stability over time. This stability over time can be evaluated by appearance.

[0083] Due to the properties described above, the sucrose fatty acid esters of the present invention can be used in food, medicine, cosmetics, industrial products, and other applications.

[0084] In particular, the sucrose fatty acid ester of the present invention has the advantages of being less likely to have the bitter taste characteristic of emulsifiers and having an excellent umami flavor, and therefore can be used as an emulsifier for food, especially beverages.

[0085] In addition to sensory tests, "bitterness" and "umami" can also be objectively evaluated using electronic taste systems. Examples of such electronic taste systems include Alpha MOS's ASTREE, but they are not limited to this.

[0086] 2. Foods containing sucrose fatty acid esters of the present invention

[0087] The sucrose fatty acid esters of the present invention are suitable for food applications due to their low bitterness and high umami flavor.

[0088] For example, the sucrose fatty acid esters of the present invention can be used as emulsifying stabilizers, particularly for oil-in-water emulsion compositions.

[0089] Foods suitable for using the sucrose fatty acid esters of the present invention are not particularly limited, but include: milk coffee, milk tea, milk cocoa and other dairy beverages; whipped cream, coffee creamer, coffee-containing soft drinks, tea drinks, cocoa drinks, almond drinks, oat drinks, coconut milk, rice milk, cashew milk, soy milk, pea milk, fruit juice drinks, walnut drinks, barley milk, macadamia nut milk, corn soup, soft ice cream mixes, chocolate, cakes, bread, sauces, salad dressings, curry cubes, etc.

[0090] The content of sucrose fatty acid esters in food is not particularly limited, but a higher content is preferred from the perspective of emulsification stability, while a lower content is preferred from the perspective of maintaining the original flavor of the food. Specifically, from the perspective of emulsification stability, the content of sucrose fatty acid esters in food is preferably 0.01% by weight or more, more preferably 0.03% by weight or more, and even more preferably 0.05% by weight or more. From the perspective of flavor, it is preferably 1% by weight or less, more preferably 0.5% by weight or less, and even more preferably 0.3% by weight or less.

[0091] In addition to the sucrose fatty acid ester of the present invention, the food may also contain emulsifiers other than the sucrose fatty acid ester of the present invention, water, oil, other food raw materials or food additives, etc.

[0092] Specifically, for example, if it is whipped cream, one could cite ingredients such as fresh cream, sodium caseinate, skim milk powder, thickeners and stabilizers.

[0093] 3. Beverages containing sucrose fatty acid esters of the present invention

[0094] The sucrose fatty acid esters of the present invention are particularly suitable for use in beverages.

[0095] The beverage containing the sucrose fatty acid esters of the present invention (hereinafter, sometimes simply referred to as "the beverage of the present invention") preferably contains a higher content of the sucrose fatty acid esters of the present invention in terms of emulsification stability and a lower content in terms of maintaining the original flavor of the food.

[0096] Specifically, from the viewpoint of emulsification stability, the content of sucrose fatty acid esters in the beverage of the present invention is preferably 100 ppm or more, more preferably 300 ppm or more, and even more preferably 500 ppm or more. From the viewpoint of flavor, it is preferably 3000 ppm or less, more preferably 2000 ppm or less, and even more preferably 1500 ppm or less.

[0097] The sucrose fatty acid ester contained in the beverage of the present invention can be directly incorporated into the beverage, or it can be incorporated in the form of an emulsion premixed with oil.

[0098] To further improve emulsification stability, the beverage of the present invention may contain other emulsifiers and stabilizers. Examples of such additional emulsifiers and stabilizers include ionic emulsifiers and sodium caseinate.

[0099] Organic monoglycerides (e.g., glyceryl monosuccinate, glyceryl monocitrate) are particularly preferred as ionic emulsifiers. The content of the ionic emulsifier is appropriately determined according to the composition of the beverage and the type of ionic emulsifier, with a lower limit preferably of 30 ppm or more, more preferably 75 ppm or more, and even more preferably 150 ppm or more. The upper limit is preferably 500 ppm or less, more preferably 350 ppm or less.

[0100] The sodium caseinate content is appropriately determined based on the composition of the beverage, with a lower limit preferably of 100 ppm or more, more preferably 150 ppm or more, further preferably 300 ppm or more, particularly preferably 600 ppm or more, and most preferably 800 ppm or more. The upper limit is preferably 1500 ppm or less, more preferably 1200 ppm or less.

[0101] Regarding the oils contained in the beverage of the present invention, from the viewpoint of making the beverage have a preferred flavor, milk fat, coconut oil, palm oil, palm kernel oil, sunflower seed oil, rapeseed oil, and oils obtained by hydrogenation of these oils, and oils obtained by transesterification of these oils are preferred, with milk fat, coconut oil, palm oil, and palm kernel oil being more preferred. From the viewpoint of flavor and emulsification stability, the content of oils contained in the beverage of the present invention is preferably 0.1 to 5% by weight, more preferably 0.3 to 3% by weight, further preferably 0.3 to 2.0% by weight, and particularly preferably 0.4 to 1.2% by weight.

[0102] The beverage of the present invention may contain organic acids and their salts, sodium bicarbonate, phosphates and other pH adjusters.

[0103] The beverage of the present invention may also contain sugars, sugar alcohols, sweeteners, flavorings, flavoring ingredients, mineral ingredients, nutritional ingredients, antioxidants, preservatives, and alcoholic beverages.

[0104] Examples of sugars include granulated sugar, white sugar, fructose, glucose, maltose, galactose, mannose, fucose, xylose, trehalose, lactose, mannan oligosaccharides, maltodextrin, and other monosaccharides and oligosaccharides.

[0105] Examples of sugar alcohols include erythritol, xylitol, maltitol, sorbitol, mannitol, and inositol.

[0106] Examples of sweeteners include sucralose, aspartame, acesulfame potassium, neotame, and stevia extract.

[0107] Examples of flavorings include lemon oil, orange oil, peppermint oil, coffee flavoring, black tea flavoring, butter flavoring, cream flavoring, and milk flavoring.

[0108] As flavoring ingredients, examples include beta-carotene, astaxanthin, lycopene, capsicum pigment, chlorophyll, and salt.

[0109] As a mineral raw material, examples include salts of calcium, iron, magnesium, potassium, etc.

[0110] Examples of nutritional raw materials include vitamins, coenzyme Q10, amino acids, peptides, DHA, and EPA.

[0111] Examples of antioxidants include vitamin C, sodium vitamin C, vitamin E, rosemary extract, tea extract, and bayberry extract.

[0112] Examples of preservatives include mustard extract, lysozyme, nisin, sorbic acid and its salts.

[0113] As for alcoholic beverages, examples include liqueurs, vodka, and spirits.

[0114] The above-mentioned components and the sucrose fatty acid ester of the present invention are emulsified by mixing appropriately with water or the like and then stirring. As for the emulsification method, any homogenization emulsification method commonly used in food can be used without particular limitation. Specifically, for example, methods using a homogenizer, methods using a colloid mill, methods using a homogenizer, etc., can all be used.

[0115] Homogenization and emulsification are typically performed at a temperature of 40–80°C. It should be noted that high-pressure emulsification is preferred when using a homogenizer for homogenization and emulsification. In a single-stage process, a stable beverage can be obtained by performing high-pressure emulsification at a processing pressure typically of 5 MPa or higher, preferably 10 MPa or higher, more preferably 15 MPa or higher, even more preferably 20 MPa or higher and typically 200 MPa or lower, preferably 100 MPa or lower, even more preferably 40 MPa or lower. In a multi-stage process, such as a two-stage process, a stable beverage can be obtained by performing at least one stage of high-pressure emulsification at a processing pressure typically of 5 MPa or higher, preferably 10 MPa or higher, more preferably 15 MPa or higher, even more preferably 20 MPa or higher and typically 200 MPa or lower, preferably 100 MPa or lower, even more preferably 40 MPa or lower.

[0116] After homogenization and emulsification, sterilization processes such as UHT sterilization and cooking sterilization are performed. Cooking sterilization is typically carried out at 110-140°C, for example, 121°C, for 10-40 minutes. On the other hand, UHT sterilization used for beverages in PET bottles is ultra-high temperature sterilization, with a sterilization temperature of 120-150°C and a sterilization value (Fo) of 10-50 at 121°C. UHT sterilization can be carried out by known methods such as direct heating methods (e.g., steam injection, where water vapor is directly blown into the beverage; steam immersion, where the beverage is sprayed into water vapor for heating); and indirect heating methods (e.g., using surface heat exchangers such as plates or tubes). For example, a plate sterilization device can be used.

[0117] Alternatively, the sucrose fatty acid ester of the present invention can be incorporated into an oil-in-water emulsion that does not contain coffee, tea, or cocoa components. The prepared oil-in-water emulsion is then mixed with coffee, tea, or cocoa components, and the above-mentioned homogenization and sterilization processes are performed to manufacture a beverage.

[0118] The sucrose fatty acid esters of this invention have a mildly unpleasant bitter taste and a high umami flavor, therefore they can be used in coffee, coffee beverages, caffeinated soft drinks, tea beverages, cocoa beverages, almond beverages, oat beverages, coconut milk, rice milk, cashew milk, soy milk, pea milk, fruit juice beverages, walnut beverages, barley milk, and macadamia nut milk. They are particularly suitable for coffee beverages, tea beverages, almond beverages, and oat beverages, and especially for coffee beverages.

[0119] The beverage of the present invention is suitable for packaged beverages, such as canned beverages, PET bottled beverages, carton-packaged beverages, glass bottled beverages, plastic container beverages, etc.

[0120] 4. Coffee and tea beverages containing sucrose fatty acid esters of the present invention

[0121] The coffee of the present invention comprises a liquid containing components derived from coffee beans, such as a solution obtained by extracting ground roasted beans with water or warm water, or a liquid obtained by dissolving a concentrated coffee extract or a dried instant coffee extract in water. The coffee beans used as the raw material for the coffee extract in the present invention can be Arabica or Robusta, without particular limitation. Examples of green beans include those selected from Mexico, Guatemala, Blue Mountain, Crystal Mountain, Costa Rica, Colombia, Venezuela, Brazil Santos, Hawaii Kona, Mocha, Kenya, Kilimanjaro, Mandheling, and Robusta, or blends thereof.

[0122] The coffee extract used in this invention is preferably extracted with 1L of water relative to 1-100g of coffee beans, more preferably relative to 20-80g, and the water temperature during extraction is preferably 60-95°C. Furthermore, the extraction time is preferably 30-120 minutes. The extraction method for the coffee extract of this invention is not particularly limited; for example, it can be extracted using conventional drip filtration, maceration, espresso, etc.

[0123] The tea beverage (tea-based beverage) of the present invention is a beverage based on tea and tea substitutes, including green tea beverages, black tea beverages, mixed tea beverages, oolong tea beverages, and barley tea beverages. The tea beverage of the present invention can be prepared from a tea extract, its concentrate, or its dilution, manufactured using methods commonly used in the preparation of tea extracts. For example, the tea extract used in the present invention can be obtained by mixing tea leaves with water (0°C to 100°C), or by mixing or dissolving a concentrate or refined product of tea extract such as tea extract or tea powder in water (0°C to 100°C). Alternatively, a substance obtained by mixing the tea extract obtained by mixing the tea leaves with water as described above, and a mixture of the tea extract or tea powder, can also be used as a tea extract in the tea beverage of the present invention. When mixing tea leaves with water, separation methods such as centrifugation or filtration can be used to separate the tea leaves from the tea extract. Furthermore, any raw material other than tea leaves can be added when preparing the tea extract.

[0124] From the viewpoint of emulsification stability and antibacterial properties, the content of sucrose fatty acid esters of the present invention in coffee or tea beverages is preferably higher, specifically, preferably 100 ppm or more, more preferably 200 ppm or more, further preferably 300 ppm or more, and particularly preferably 500 ppm or more. On the other hand, from the viewpoint of flavor, the content of sucrose fatty acid esters of the present invention is preferably lower, specifically, preferably 3000 ppm or less, more preferably 2000 ppm or less, further preferably 1500 ppm or less, and particularly preferably 1200 ppm or less.

[0125] Example

[0126] The present invention will be specifically described below through embodiments, but the present invention is not limited to these embodiments.

[0127] Manufacturing Example 1

[0128] 0.05 mol of methyl stearate and 0.2 mol of methyl palmitate were reacted with 1 mol of sucrose. DMSO was used as a solvent, with a relative content of 30% by weight of sucrose, methyl stearate, and methyl palmitate. The reaction was carried out under anhydrous conditions using potassium carbonate as a catalyst at 90 °C and 2.7 kPa. The byproduct lower alcohol was removed by distillation during the reaction. After the reaction was complete, the catalyst was neutralized with lactic acid to obtain crude sucrose fatty acid esters. The solvent was removed, and the crude sucrose fatty acid esters were purified to obtain sucrose fatty acid esters (powder).

[0129] Manufacturing Example 2

[0130] Following the method of Manufacturing Example 1, 0.20 mol of methyl stearate, 0.1 mol of methyl palmitate, and 1 mol of sucrose were reacted to obtain sucrose fatty acid ester (powder).

[0131] Manufacturing Example 3

[0132] Following the method of manufacturing Example 1, 0.67 moles of methyl palmitate were reacted with 1 mole of sucrose to obtain sucrose fatty acid ester (powder).

[0133] Manufacturing Example 4

[0134] Following the method of Manufacturing Example 1, 0.25 moles of methyl palmitate were reacted with 1 mole of sucrose to obtain sucrose fatty acid ester (powder).

[0135] Manufacturing Example 5

[0136] For the sucrose fatty acid ester of Example 1, separation was carried out under the following conditions, the liquid with a retention time of 35 minutes was collected, the solvent was removed by an evaporator and purified to obtain sucrose palmitate palmitate (powder).

[0137] • Device: Thermo Fisher U3000 series

[0138] • Column: Inertsil C8 4.6×150mm, 5μm

[0139] Column temperature: 40℃

[0140] • Eluent: Eluent A (water) B (methanol / THF 9 / 1)

[0141] ·A / B=30 / 70(0)=>20 / 80(20)=>0 / 100(35)=>0 / 100(50)=>30 / 70(53)=>30 / 70(60)

[0142] Manufacturing Example 6

[0143] The sucrose fatty acid ester of Production Example 1 was separated under the same conditions as in Production Example 5, the liquid with a retention time of 36.7 minutes was collected, and the solvent was removed using an evaporator for purification, to obtain sucrose stearic stearate (powder).

[0144] Production Examples 7 to 14

[0145] The sucrose fatty acid esters of Production Examples 1 to 6 were mixed at the ratios described in Table 1, to obtain the sucrose fatty acid esters of Production Examples 7 to 14.

[0146] [Table 1]

[0147]

[0148] The sucrose fatty acid esters of Production Examples 1, 2, and 7 to 11 were subjected to LC-CAD analysis, to quantify the monoester ratio and diester ratio of the sucrose fatty acid esters, the fatty acid composition of the monoester bodies (P body: sucrose monopalmitate, S body: sucrose monostearate), and the fatty acid composition of the diester bodies (PS body: sucrose palmitate stearate, PP body: sucrose palmitate palmitate, SS body: sucrose stearate stearate).

[0149] <LC-CAD Analysis>

[0150] ·Apparatus: Thermo Fisher U3000 series

[0151] ·Detector: Corona Veo RS

[0152] ·Column: Inertsil C8 4.6×150mm, 5μm

[0153] ·Column temperature: 40°C

[0154] ·Eluent: Eluent A (water) B (methanol / THF 9 / 1)

[0155] ·A / B=30 / 70(0)=>20 / 80(20)=>0 / 100(35)=>0 / 100(50)=>30 / 70(53)=>30 / 70(60)

[0156] [Table 2]

[0157]

[0158] Examples 1 to 5 and Comparative Examples 1, 2

[0159] After adjusting the pH of coffee extract with sodium bicarbonate dissolved in hot water, sugar, milk, and sucrose fatty acid esters from Examples 1, 2, and 7-11 were added in the amounts described in Table 3, mixed, and dissolved. Water was then added to bring the total volume to 100% (by weight). The liquid was heated to 65°C, homogenized at 20 MPa using a high-pressure homogenizer, filled into cans, sealed, and sterilized at 121°C for 30 minutes to prepare canned milk coffee. The pH of the sterilized beverage was 6.6-6.8.

[0160] Use raw materials

[0161] Coffee extract: "Coffee Extract COL-19" manufactured by Takasago Flavoring Co., Ltd.

[0162] Milk: Produced by MEGMILK SNOW BRAND

[0163] Sugar: Nisshin Sugar Co., Ltd.

[0164] The following evaluations were conducted on the obtained canned milk coffee. The results are summarized in Table 3.

[0165] [Taste Sensor]

[0166] For pasteurized milk coffee, taste properties were measured using the ASTREE electronic taste system (manufactured by Alpha MOS) under the following conditions.

[0167] • Sample volume: 25ml of coffee

[0168] Data acquisition time: 120 seconds

[0169] The measurement data were analyzed using AlphaSoft (manufactured by Alpha MOS). Specifically, the average values ​​of the sensor measurements were quantified according to taste attributes, using an intensity scale of 0-12, to compare the scores of umami and bitterness. Both the umami score (NMS) and bitterness score (SCS) are represented by 0 for the weakest taste and 12 for the strongest taste.

[0170] [Sensory Evaluation]

[0171] Using pasteurized milk coffee, trained subjects evaluated the flavor of the milk coffee according to the following criteria.

[0172] Good: weak bitterness, strong umami taste

[0173] No: Strong bitterness, weak umami flavor

[0174] Stability evaluation

[0175] Store each can of milk coffee at 60°C for 4 weeks, then let it stand overnight at 5°C. The next day, open the can and visually observe the oil droplets and oil separation when transferring the contents to a cup, and evaluate according to the following criteria.

[0176] 1: There are a lot of butter granules and separated oil.

[0177] 2: A small amount of cream granules and separated oil are present.

[0178] 3: A very small amount of cream granules and separated oil are present.

[0179] 4: A very small amount of either butter granules or separated oil is present.

[0180] 5: Completely free of butter lumps and oil separation, indicating a good condition.

[0181] [Table 3]

[0182]

[0183] Examples 1-4, and Comparative Examples 1 and 2, respectively contained 3.5% by mass of coffee extract, 5% by mass of sugar, 24% by mass of milk, and 0.1% by mass of sodium bicarbonate.

[0184] Stability evaluation: Dispersibility after storage at 60°C for 4 weeks

[0185] As shown in Tables 2 and 3, if sucrose fatty acid esters with fewer PS bodies than PP and SS bodies in the diester are used, the umami flavor increases and the bitterness decreases.

[0186] Example 6

[0187] The milk coffee prepared in Example 1 was prepared using the same method as in Example 1, except that the sucrose fatty acid ester from Manufacturing Example 12 was used instead of the sucrose fatty acid ester from Manufacturing Example 7 used in Example 1. Sensory evaluation was performed using the same method. Regarding the stability test, the evaluation was performed using the same method, except that the storage temperature was changed to 60°C for 2 weeks. The results are shown in Table 4.

[0188] [Table 4]

[0189]

[0190] As shown in Table 4, if sucrose fatty acid esters with less PS body than PP body and SS body are used in diesters, a beverage with strong umami flavor and weak bitterness can be obtained.

[0191] Comparative Examples 3 and 4

[0192] For the milk coffee prepared in Example 1, except that the sucrose fatty acid esters of Manufacturing Examples 13 and 14 were used instead of the sucrose fatty acid esters of Manufacturing Example 7 used in Example 1, the milk coffee was prepared using the same method as in Example 1, and sensory evaluation was performed using the same method. Regarding the stability test, except that it was changed to storage at 60°C for 2 weeks, the evaluation was performed using the same method. The results are shown in Table 5.

[0193] [Table 5]

[0194]

[0195] As shown in Table 5, it can be seen that when the diester in sucrose fatty acid esters is only PP, the stability deteriorates.

[0196] Examples 7 and 8 and Reference Examples 1 and 2

[0197] In the beverage prepared in Example 2, caseinate Na (Tatula 100), glyceryl monosuccinate (Poem B-30), and polyglycerol fatty acid ester (S-10D) were added in the amounts described in Table 6, mixed, and dissolved. Water was then added to bring the total amount to 100g by weight. The resulting liquid was heated to 65°C and homogenized to prepare milk coffee.

[0198] 20 ml of the prepared milk coffee was poured into a glass vial with an inner diameter of 25 mm, and backscattering was measured using a TURBISCAN TOWER (formulation-made). The degree of emulsification was evaluated by the increase in backscattering intensity (ΔB(%)) from 1 mm (39 mm to 40 mm) above the liquid surface of the vial containing the prepared milk coffee, after initial dispensing and after standing at 20°C for 12 hours. A higher amount of emulsification in the milk coffee resulted in increased backscattering intensity and a larger ΔB(%), which could be considered a sign of poor quality. The results are shown in Table 6.

[0199] [Table 6]

[0200]

[0201] The stability of beverages containing sucrose fatty acid esters with low PS content is improved by combining them with stabilizers such as glyceryl monosuccinate and sodium caseinate.

[0202] Based on the above results, sucrose fatty acid esters with lower PS content than PP and SS content exhibit lower bitterness and higher umami flavor when incorporated into food compared to sucrose fatty acid esters with higher PS content produced using existing methods. In particular, sucrose fatty acid esters with PS content below 31% of the total diester body show lower bitterness and higher umami flavor when incorporated into food.

[0203] It is presumed that when the PS ratio of the diester of sucrose fatty acid esters is below a certain level, the adsorption behavior of sucrose fatty acid esters onto the taste buds of the tongue changes, thus reducing the bitterness and increasing the umami flavor of beverages containing the sucrose fatty acid esters of the present invention. Specifically, with conventional sucrose fatty acid esters with a high PS ratio, bitterness is perceived through adsorption of sucrose fatty acid esters onto the bitter taste receptors of the taste buds, and umami flavor is difficult to perceive because sucrose fatty acid esters hinder the adsorption of umami components in the beverage onto the umami receptors of the taste buds. On the other hand, it is presumed that with the sucrose fatty acid esters of the present invention, since sucrose fatty acid esters do not readily adsorb onto the bitter taste receptors of the taste buds, bitterness is not easily perceived, and since sucrose fatty acid esters do not readily hinder the adsorption of umami components in the beverage onto the umami receptors of the taste buds, umami flavor is strongly perceived.

[0204] Industrial utilization potential

[0205] Compared to conventional sucrose fatty acid esters, the sucrose fatty acid esters of the present invention exhibit reduced bitterness and increased umami flavor when incorporated into food. Therefore, the sucrose fatty acid esters of the present invention are useful as emulsifiers in beverages and the like.

[0206] All prior art documents referenced in this specification are incorporated herein by reference.

Claims

1. A sucrose fatty acid ester, wherein at least a portion of the hydroxyl groups of sucrose are replaced by aliphatic hydrocarbon groups, and satisfies all of the following (1) to (3): (1) Contains sucrose palmitate and sucrose stearate. (2) The content of sucrose palmitate stearate is below the content of sucrose palmitate stearate. (3) The content of sucrose palmitic stearate is below that of sucrose stearate.

2. The sucrose fatty acid ester according to claim 1, wherein, The sucrose palmitate stearate accounts for less than 31% of the total diester.

3. The sucrose fatty acid ester according to claim 2, wherein, The proportion of monoesters to the total ester body is 50-90%, and the proportion of diesters to the total ester body is 5-45%.

4. The sucrose fatty acid ester according to claim 3, wherein, The sucrose palmitate stearate accounts for more than 10% and less than 31% of the total diester.

5. The sucrose fatty acid ester according to claim 4, wherein, The sucrose stearate is 15-35% of the total diester.

6. The sucrose fatty acid ester according to claim 5, wherein, The sucrose palmitate palmitate accounts for 50% to 90% of the total diester.

7. A sucrose fatty acid ester, wherein at least a portion of the hydroxyl groups of sucrose are replaced by aliphatic hydrocarbon groups, satisfying the following (1) and (2): (1) Contains sucrose palmitate and sucrose stearate. (2) The sucrose palmitate stearate content is less than 31% of the total diester.

8. The sucrose fatty acid ester according to claim 7, wherein, The proportion of monoesters to the total ester body is 50-90%, and the proportion of diesters to the total ester body is 5-45%.

9. The sucrose fatty acid ester according to claim 8, wherein, The sucrose palmitate stearate accounts for more than 10% and less than 31% of the total diester.

10. The sucrose fatty acid ester according to claim 9, wherein, The sucrose stearate is 15-35% of the total diester.

11. The sucrose fatty acid ester according to claim 10, wherein, The sucrose palmitate palmitate accounts for 50% to 90% of the total diester.

12. A food product containing any one of the sucrose fatty acid esters according to claims 1 to 11.

13. A beverage containing any one of the sucrose fatty acid esters according to claims 1 to 11.

14. The beverage according to claim 13, further comprising one or more stabilizers selected from organic monoglycerides and sodium caseinate.

Images