Novel sucrose fatty acid ester

Abstract

The present invention provides a sucrose fatty acid ester which has reduced bitterness and which facilitates perception of umami taste, a food in which the sucrose fatty acid ester is used, etc.　Provided is a sucrose fatty acid ester characterized in that a palmitic acid stearic acid ester in a diester contained in the sucrose fatty acid ester is relatively low. Specifically, provided is a sucrose fatty acid ester in which a part of a hydroxyl group of sucrose is substituted with an aliphatic hydrocarbon group, said sucrose fatty acid ester satisfying all of the following (1) to (3). (1) Said sucrose fatty acid ester contains a palmitic acid palmitic acid ester and a stearic acid stearic acid ester. (2) The content of a palmitic acid stearic acid ester is equal to or lower than the content of the palmitic acid palmitic acid ester. (3) The content of the palmitic acid stearic acid ester is equal to or lower than the content of the stearic acid stearic acid ester.

Description

Novel sucrose fatty acid esters

[0001] The present invention relates to a novel sucrose fatty acid ester, specifically a sucrose fatty acid ester characterized in that the content of palmitic acid stearate in the diesters contained therein is relatively low.

[0002] Sucrose fatty acid esters are compounds in which at least some of the eight hydroxyl groups in a sucrose molecular skeleton are esterified with fatty acid hydrocarbon groups. Sucrose fatty acid esters include monoesters, diesters, triesters, and other esters ranging from monovalent to polyvalent.

[0003] It has been reported that when a sucrose fatty acid ester having a specific ester composition is used as an emulsifier for an oil-in-water emulsion composition, the viscosity of the composition can be increased (Patent Document 1). It has also been reported that emulsion stability can be improved by controlling the molar ratio of the sucrose fatty acid diester to the higher fatty alcohol and / or higher fatty acid (Patent Document 2).

[0004] Sucrose fatty acid esters with a low degree of substitution are highly hydrophilic and are used in the food emulsifier market as emulsion stabilizers for oil-in-water (O / W) emulsions such as coffee with milk. However, they have problems in that they tend to give off a bitter taste derived from the emulsifier and further make it difficult to sense the umami flavor of foods.

[0005] In order to reduce the bitterness of sucrose fatty acid esters, methods have been reported in which the amount of sucrose fatty acid ester required to be incorporated into foods is reduced by increasing the palmitate ester purity of the sucrose fatty acid ester, and methods for producing sucrose fatty acid esters by irradiating with microwaves. However, the problems that sucrose fatty acid esters with high palmitate ester purity and sucrose fatty acid esters produced by irradiating with microwaves tend to destabilize emulsions when incorporated into beverages, and furthermore, make it difficult to sense the umami taste of foods containing sucrose fatty acid esters, have not been fully resolved (see Patent Documents 3, 4, and 5).

[0006] JP 2009-214079 A, ​​JP 8-268877 A, JP 2023-047770 A, WO 2017 / 013966, WO 19 / 235619

[0007] A main object of the present invention is to provide a sucrose fatty acid ester that has reduced bitterness and an easily perceived umami taste, and a food product and the like that uses the sucrose fatty acid ester.

[0008] The inventors have found that the above problem can be solved by making the proportion of palmitic acid stearate lower than the proportions of palmitic acid palmitate and stearic acid stearate in the diesters contained in the sucrose fatty acid ester.

[0009] That is, the present invention provides the following [1] to [6]. In this specification, unless otherwise specified, "%" means "% by weight". [1] A sucrose fatty acid ester in which at least a portion of the hydroxyl groups of sucrose are substituted with aliphatic hydrocarbon groups, the sucrose fatty acid ester satisfying all of the following (1) to (3): (1) containing sucrose palmitate palmitate and sucrose stearate stearate (2) the content of sucrose palmitate stearate is equal to or less than the content of sucrose palmitate palmitate (3) the content of sucrose palmitate stearate is equal to or less than the content of sucrose stearate stearate. [2] The sucrose fatty acid ester according to [1], in which the content of sucrose palmitate stearate is 31% or less of the total amount of diesters. [3] The sucrose fatty acid ester according to [1] or [2], wherein the proportion of monoesters is 50 to 90% and the proportion of diesters is 5 to 45% based on the total amount of esters. [4] The sucrose fatty acid ester according to any one of [1] to [3], wherein the sucrose palmitic acid stearate accounts for 10% to 31% based on the total amount of diesters. [5] The sucrose fatty acid ester according to any one of [1] to [4], wherein the sucrose stearate accounts for 15 to 35% based on the total amount of diesters. [6] The sucrose fatty acid ester according to any one of [1] to [5], wherein the sucrose palmitic acid palmitate accounts for 50 to 90% based on the total amount of diesters. [7] A sucrose fatty acid ester in which at least a portion of the hydroxyl groups of sucrose are substituted with aliphatic hydrocarbon groups, the sucrose fatty acid ester satisfying the following (1) and (2): (1) The sucrose fatty acid ester comprises sucrose palmitate palmitate and sucrose stearate stearate. (2) The content of sucrose palmitate stearate is 31% or less based on the total amount of diesters. [8] The sucrose fatty acid ester according to [7], in which the proportion of monoesters is 50 to 90% and the proportion of diesters is 5 to 45% based on the total amount of esters. [9] The sucrose fatty acid ester according to [7] or [8], in which the content of sucrose palmitate stearate is 10% or more and 31% or less based on the total amount of diesters.

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

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

[10] , wherein the sucrose palmitate palmitate accounts for 50 to 90% of the total amount of diesters.

[12] A food product containing the sucrose fatty acid ester according to any one of [1] to

[11] .

[13] A beverage containing the sucrose fatty acid ester according to any one of [1] to

[11] .

[14] The beverage according to

[13] , further comprising one or more stabilizers selected from organic monoglycerides and sodium caseinate. This specification incorporates the disclosure of Japanese Patent Application No. 2024-060604, from which the present application claims priority.

[0010] The sucrose fatty acid ester of the present invention has reduced bitterness and increased umami when incorporated into foods compared with conventional sucrose fatty acid esters, and is therefore useful as an emulsifier for beverages and the like.

[0011] 1. Sucrose Fatty Acid Esters of the Present Invention Sucrose fatty acid esters are compounds in which at least some of the eight hydroxyl groups in a sucrose molecular skeleton are esterified with aliphatic hydrocarbon groups. In other words, sucrose fatty acid esters are compounds having a structure in which at least some of the eight hydroxyl groups in a sucrose molecular skeleton are substituted by esterification with a fatty acid. In yet other words, sucrose fatty acid esters have a structure in which at least some of the hydroxyl groups in sucrose are esterified with a fatty acid containing an aliphatic hydrocarbon group. Depending on the degree of esterification, the esters contained in sucrose fatty acid esters can be classified into monoesters (esterification degree 1), diesters (esterification degree 2), and polyesters (esterification degree 3 or higher).

[0012] The sucrose fatty acid ester of the present invention is a sucrose fatty acid ester containing palmitic acid and stearic acid as constituent fatty acids, and the diesters can be classified into sucrose palmitate palmitate esters (hereinafter sometimes abbreviated as palmitate palmitate esters) in which two palmitic acids are ester-bonded to sucrose, sucrose stearate stearate (hereinafter sometimes abbreviated as stearic acid stearate esters) in which two stearic acids are ester-bonded to sucrose, and sucrose palmitate stearate esters (hereinafter sometimes abbreviated as palmitate stearate esters) in which one palmitic acid and one stearic acid are ester-bonded. Note that sucrose has eight hydroxyl groups in its molecular skeleton, and various diester isomers exist depending on which hydroxyl groups in the sucrose molecular skeleton are ester-bonded to the two fatty acids. However, since the difference in function between isomers depending on the diester bond position is considered to be very small, the present invention does not distinguish between isomers depending on the diester bond position.

[0013] The sucrose fatty acid ester of the present invention is characterized in that it contains at least palmitic acid palmitate and stearic acid stearate as diesters, and the content of palmitic acid stearate in the sucrose fatty acid ester is lower than the contents of either palmitic acid palmitate or stearic acid stearate.

[0014] In a first embodiment, the sucrose fatty acid ester of the present invention satisfies all of the following (1) to (3): (1) It contains palmitic acid palmitate and stearic acid stearate, (2) The content of palmitic acid stearate is equal to or less than the content of palmitic acid palmitate, and (3) The content of palmitic acid stearate is equal to or less than the content of stearic acid stearate.

[0015] It is believed that the inclusion of palmitic acid palmitate and stearic acid stearate results in superior emulsification performance compared to either of them alone. Furthermore, it is believed that the bitterness is reduced and a sucrose fatty acid ester with an easily perceived umami taste can be obtained by (2) having a palmitic acid stearate content equal to or less than that of palmitic acid palmitate, and (3) having a palmitic acid stearate content equal to or less than that of stearic acid stearate.

[0016] In the first embodiment, the palmitic acid palmitate ester is preferably 5% to 99%, more preferably 20% to 99%, even more preferably 40% to 95%, particularly preferably 50% to 90%, and most preferably 65% ​​to 85%, based on the total amount of the diester.

[0017] In the first embodiment, the stearate ester is preferably 5% to 99%, more preferably 5% to 60%, even more preferably 5% to 40%, particularly preferably 10% to 35%, and most preferably 15% to 35%, based on the total amount of the diester.

[0018] The phrase "content or less" in (2) and (3) above also includes the case where the palmitic acid stearate content is "0".

[0019] In the first embodiment, the content of palmitic acid stearate is preferably 31% or less based on the total amount of diesters. From the viewpoint of good emulsion stability when incorporated into foods, the content of palmitic acid stearate is preferably 21% or less, more preferably 15% or less, even more 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 incorporated into foods, the content of palmitic acid stearate is preferably 2% or more, more preferably 5% or more, even more preferably 10% or more, particularly preferably 12% or more, even more particularly preferably 15% or more, and most preferably 18% or more.

[0020] In a second embodiment, the sucrose fatty acid ester of the present invention satisfies the following (1) and (2): (1) it contains palmitic acid palmitate and stearate stearate; and (2) the content of palmitic acid stearate is 31% or less based on the total amount of diesters.

[0021] It is believed that the inclusion of palmitic acid palmitate and stearic acid stearate provides superior emulsifying performance compared to either of them alone, and that the palmitic acid stearate content of 31% or less of the total amount of diesters reduces bitterness, resulting in a sucrose fatty acid ester with a more easily perceived umami taste.

[0022] In the second embodiment, the palmitic acid ester is preferably 5% to 99%, more preferably 20% to 99%, even more preferably 40% to 95%, particularly preferably 50% to 90%, and most preferably 65% ​​to 85%, based on the total amount of the diester.

[0023] In the second embodiment, the stearate ester is preferably 5% to 99%, more preferably 5% to 60%, even more preferably 5% to 40%, particularly preferably 10% to 35%, and most preferably 15% to 35%, based on the total amount of the diester.

[0024] In the second embodiment, from the viewpoint of providing good emulsion stability when incorporated into foods, the palmitic acid stearate is preferably 21% or less, more preferably 15% or less, even more preferably 8% or less, particularly preferably 4% or less, and most preferably 1% or less. From the viewpoint of reducing bitterness and increasing umami when incorporated into foods, the palmitic acid stearate is preferably 2% or more, more preferably 5% or more, even more preferably 10% or more, particularly preferably 12% or more, even more particularly preferably 15% or more, and most preferably 18% or more.

[0025] In both the first and second embodiments (hereinafter the same), among the diesters contained in the sucrose fatty acid ester of the present invention, the ratio of palmitic acid palmitate to stearic acid stearate is preferably 0.1 to 3 parts by weight, more preferably 0.1 to 0.8 parts by weight, even more preferably 0.15 to 0.6 parts by weight, and particularly preferably 0.15 to 0.3 parts by weight, per part by weight of palmitic acid palmitate. When the ratio of palmitic acid palmitate to stearic acid stearate is within the above range, the resulting food product can have an excellent flavor and exhibit a high emulsifying function.

[0026] Among the monoesters contained in the sucrose fatty acid ester of the present invention, the ratio of palmitate ester to stearic acid ester is preferably 0.1 to 3 parts by weight, more preferably 0.1 to 0.8 parts by weight, even more preferably 0.2 to 0.6 parts by weight, and particularly preferably 0.25 to 0.5 parts by weight, per part by weight of palmitate ester. When the ratio of palmitate ester to stearic acid ester is within the above range, excellent bacteriostatic activity can be exhibited in foods.

[0027] In the sucrose fatty acid ester of the present invention, the proportions of the monoester and diester relative to the total amount of esters are preferably 50% to 90% and 5% to 45%, respectively, more preferably 60% to 90% and 10% to 40%, even more 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%. When the proportions of the monoester and diester are within the above ranges, the sucrose fatty acid ester can exhibit excellent dispersing, emulsion-stabilizing, and bacteriostatic effects in foods.

[0028] 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, even more preferably 80% or more, particularly preferably 90% or more, and most preferably 95% or more. By being in this range, high dispersibility can be maintained when used in foods containing a large amount of water.

[0029] The sucrose fatty acid ester of the present invention may have an aliphatic hydrocarbon group other than palmitic acid or stearic acid. In order to obtain an oil-in-water emulsion with high emulsion stability, the aliphatic hydrocarbon group is preferably a saturated hydrocarbon group. Furthermore, a chain hydrocarbon group is preferred, and a linear hydrocarbon group is more preferred.

[0030] The number of carbon atoms in the aliphatic hydrocarbon group is preferably large in terms of hydrophilicity, dispersibility in water, and emulsion stability in an oil-in-water emulsifier. Specifically, the number of carbon atoms in the aliphatic hydrocarbon group is preferably 12 or more, more preferably 14 or more, and even more preferably 16 or more, in terms of emulsion stability, etc.

[0031] Specifically, the sucrose fatty acid ester of the present invention may have hydrocarbon groups derived from oleic acid, myristic acid, lauric acid, or behenic acid in addition to palmitic acid and stearic acid. From the viewpoint of providing excellent flavor and bacteriostasis, the sucrose fatty acid ester of the present invention preferably contains hydrocarbon groups derived from oleic acid, myristic acid, lauric acid, or behenic acid in an amount of 1% or less, more preferably 0.5% or less, and even more preferably contains no hydrocarbon groups, based on the total aliphatic hydrocarbon groups.

[0032] The type of aliphatic hydrocarbon group contained in the sucrose fatty acid ester of the present invention and its proportion relative to the total amount of aliphatic hydrocarbon groups can be confirmed by high performance liquid chromatography, an example of which is shown below. Column: Inertsil C8 4.6×150 mm, 5 μm Column temperature: 40°C Eluent: A (water) B (methanol / THF 9 / 1) A / B=30 / 70(0) => 20 / 80(20) => 0 / 100(35) => 0 / 100(50) => 30 / 70(53) => 30 / 70(60) When the above-mentioned high performance liquid chromatography was used, of the diesters contained in the sucrose fatty acid ester of the present invention, palmitic acid stearate had a retention time of 35.9 minutes, palmitic acid palmitate had a retention time of 35 minutes, and stearic acid stearate had a retention time of 36.7 minutes.

[0033] The form of the sucrose fatty acid ester is not particularly limited, and may be, for example, powder or flake form. The powder or flake can be dissolved in tetrahydrofuran and analyzed by high performance liquid chromatography as described above to determine the type of aliphatic hydrocarbon group contained in the sucrose fatty acid ester and its proportion relative to the total amount of aliphatic hydrocarbon groups.

[0034] Similarly, high performance liquid chromatography can be used to analyze the types of aliphatic hydrocarbon groups in sucrose fatty acid esters, their proportions relative to the total amount of aliphatic hydrocarbon groups, etc. For example, ethyl acetate can be added to a beverage sample and mixed, followed by recovery of the solvent phase, and the solvent is removed using an evaporator to purify the sucrose fatty acid esters from the beverage. High performance liquid chromatography can then be used as described above to analyze the types of aliphatic hydrocarbon groups in the sucrose fatty acid esters, their proportions relative to the total amount of aliphatic hydrocarbon groups, etc.

[0035] When using the general analytical method for sucrose fatty acid esters, gas chromatography, the peak sensitivity of sucrose fatty acid diesters is low, making their detection and quantification difficult.

[0036] The sucrose fatty acid ester of the present invention can be produced by mixing one or more of the reaction products obtained by the esterification reaction of sucrose with a fatty acid, the esterification reaction of sucrose with a fatty acid chloride or a fatty acid anhydride, the transesterification reaction of sucrose with a lower ester compound of a fatty acid, an enzymatic reaction, or microwave irradiation of a mixture containing a fatty acid ester or a fatty acid, and purified products obtained by purifying these reaction products by chromatography, etc. Sucrose fatty acid esters with a low degree of substitution can be produced by adjusting the ratio of fatty acid methyl ester to sucrose in the above-mentioned production process.

[0037] As in the first embodiment, a method for producing a sucrose fatty acid ester that (1) contains palmitic acid palmitate and stearic acid stearate, (2) has a palmitic acid stearate content equal to or less than that of palmitic acid palmitate, and (3) has a palmitic acid stearate content equal to or less than that of stearic acid stearate can be achieved by, for example, mixing a sucrose stearate prepared by reacting sucrose with methyl stearate containing 99% or more of stearic acid among the fatty acids in all the esters, and a sucrose palmitate prepared by reacting sucrose with methyl palmitate containing 99% or more of palmitic acid among the fatty acids in all the esters. Furthermore, palmitic stearic acid ester can be contained by mixing with these esters a product prepared by reacting sucrose with methyl stearate and methyl palmitate (including palmitic palmitic ester, stearic stearic ester, and palmitic stearic ester), and the ratio of palmitic palmitic ester, stearic stearic ester, and palmitic stearic ester can be adjusted by adjusting the mixing ratio. Sucrose fatty acid esters prepared by reacting methyl stearate and methyl palmitate with sucrose usually have a high content of palmitic stearate (e.g., Production Examples 1 and 2), except for the purpose of increasing the selectivity of the reaction.

[0038] As in the second embodiment, a method for producing a sucrose fatty acid ester containing (1) palmitic acid palmitate and stearic acid stearate and (2) palmitic acid stearate accounting for 31% or less of the total amount of diesters can be achieved by, for example, mixing a sucrose stearate prepared by reacting sucrose with methyl stearate containing 99% or more of stearic acid among the fatty acids in all esters with sucrose, and a sucrose palmitate prepared by reacting sucrose with methyl palmitate containing 99% or more of palmitic acid among the fatty acids in all esters. Furthermore, palmitic acid stearate can be incorporated by mixing a product prepared by reacting methyl stearate and methyl palmitate with sucrose (including palmitic acid palmitate, stearic acid stearate, and palmitic acid stearate), and adjusting the mixing ratio allows the ratios of palmitic acid palmitate, stearic acid stearate, and palmitic acid stearate to be adjusted. Sucrose fatty acid esters prepared by reacting sucrose with methyl stearate and methyl palmitate usually have a high palmitic acid stearate content, except for cases where the selectivity of the reaction is increased (e.g., Production Examples 1 and 2).

[0039] The sucrose fatty acid ester of the present invention can be used as an emulsion stabilizer (emulsifier), a lubricant, etc. The sucrose fatty acid ester of the present invention is excellent in oil-in-water emulsification when dispersed in water, and therefore can be suitably used particularly as an oil-in-water (O / W) emulsion stabilizer.

[0040] The sucrose fatty acid ester of the present invention has excellent stability over time as an oil-in-water (O / W) emulsion stabilizer. The stability over time can be evaluated by appearance.

[0041] Due to the above-mentioned properties, the sucrose fatty acid ester of the present invention can be suitably used in applications such as food, medicine, cosmetics, and industrial products.

[0042] In particular, the sucrose fatty acid ester of the present invention has the advantage of being less likely to have the bitter taste characteristic of emulsifiers and having an excellent umami taste, and therefore can be suitably used as an emulsifier for foods, particularly beverages.

[0043] "Bitterness" and "umami" can be objectively evaluated using an electronic taste sensor system, such as, but not limited to, ASTREE from Alpha MOS.

[0044] 2. Foods containing the sucrose fatty acid ester of the present invention The sucrose fatty acid ester of the present invention has low bitterness and high umami taste, and can therefore be suitably used in food applications.

[0045] For example, the sucrose fatty acid ester of the present invention can be used as an emulsion stabilizer, particularly as an emulsion stabilizer for oil-in-water emulsion compositions.

[0046] Foods in which the sucrose fatty acid ester of the present invention can be used include, but are not limited to, milk drinks such as milk coffee, milk tea, and milk cocoa; whipped cream, coffee whitener, coffee-containing soft drinks, tea drinks, cocoa drinks, almond drinks, oat drinks, coconut milk, rice milk, cashew nut milk, soy milk, pea milk, fruit juice drinks, walnut drinks, barley milk, macadamia milk, corn soup, soft serve ice cream mix, chocolate, cake, bread, sauce, dressing, and curry roux.

[0047] The content of the sucrose fatty acid ester of the present invention in a food product is not particularly limited, but a high content is preferable in terms of emulsion stability, and a low content is preferable in terms of maintaining the original flavor of the food product. Specifically, the content of the sucrose fatty acid ester of the present invention in a food product is preferably 0.01% by weight or more in terms of emulsion stability, more preferably 0.03% by weight or more, and even more preferably 0.05% by weight or more. In terms of flavor, the content 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.

[0048] In addition to the sucrose fatty acid ester of the present invention, the food may contain, for example, an emulsifier other than the sucrose fatty acid ester of the present invention, water, oil, other food raw materials, food additives, etc. Specific examples of whipped cream include fresh cream, sodium caseinate, skim milk powder, and thickening stabilizers.

[0049] 3. Beverages Comprising the Sucrose Fatty Acid Ester of the Present Invention The sucrose fatty acid ester of the present invention can be suitably used particularly for beverage applications.

[0050] The content of the sucrose fatty acid ester of the present invention contained in a beverage containing the sucrose fatty acid ester of the present invention (hereinafter sometimes simply referred to as the "beverage of the present invention") is preferably high in terms of emulsion stability, and is preferably low in terms of maintaining the original flavor of the food. Specifically, the content of the sucrose fatty acid ester of the present invention in the beverage is preferably 100 ppm or more, more preferably 300 ppm or more, and even more preferably 500 ppm or more in terms of emulsion stability, and is preferably 3000 ppm or less, more preferably 2000 ppm or less, and even more preferably 1500 ppm or less in terms of flavor.

[0051] The sucrose fatty acid ester of the present invention contained in the beverage of the present invention may be blended directly into the beverage, or may be blended in the form of an emulsion in which the sucrose fatty acid ester is mixed with oil in advance.

[0052] The beverage of the present invention may contain other emulsifiers or stabilizers to further improve emulsion stability, such as ionic emulsifiers and sodium caseinate.

[0053] As the ionic emulsifier, organic monoglycerides (e.g., succinic acid monoglyceride, citric acid monoglyceride) are particularly preferred. The content of the ionic emulsifier is determined appropriately depending on the composition of the beverage and the type of ionic emulsifier, but the lower limit is preferably 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.

[0054] The content of sodium caseinate is determined appropriately depending on the composition of the beverage, etc., but the lower limit is preferably 100 ppm or more, more preferably 150 ppm or more, even more 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.

[0055] The oil contained in the beverage of the present invention is preferably milk fat, coconut oil, palm oil, palm kernel oil, sunflower oil, rapeseed oil, or hydrogenated or interesterified versions of these oils and fats, from the viewpoint of imparting a pleasant flavor to the beverage, and more preferably milk fat, coconut oil, palm oil, or palm kernel oil. From the viewpoint of flavor and emulsion stability, the content of the oil contained in the beverage of the present invention is preferably 0.1 to 5 wt %, more preferably 0.3 to 3 wt %, even more preferably 0.3 to 2.0 wt %, and particularly preferably 0.4 to 1.2 wt %.

[0056] The beverage of the present invention may contain a pH adjuster such as an organic acid and its salt, baking soda, or a phosphate.

[0057] The beverage of the present invention may contain sugars, sugar alcohols, sweeteners, flavorings, flavoring materials, mineral materials, nutritional materials, antioxidants, preservatives, alcoholic beverages, and the like.

[0058] Examples of sugars include monosaccharides and oligosaccharides such as sugar, granulated sugar, fructose, glucose, maltose, galactose, mannose, fucose, xylose, trehalose, lactose, mannooligosaccharides, and maltooligosaccharides.

[0059] Examples of sugar alcohols include erythritol, xylitol, maltitol, sorbitol, mannitol, and inositol.

[0060] Sweeteners include sucralose, aspartame, acesulfame potassium, neotame, stevia extract, etc.

[0061] Examples of flavorings include lemon oil, orange oil, mint oil, coffee flavor, tea flavor, butter flavor, cream flavor, milk flavor, and the like.

[0062] Flavoring materials include carotenoids such as β-carotene, astaxanthin, lycopene, and paprika pigments, pigments such as chlorophyll, and salt.

[0063] Mineral materials include salts of calcium, iron, magnesium, potassium, etc.

[0064] Nutritional ingredients include vitamins, coenzyme Q10, amino acids, peptides, DHA, EPA, etc.

[0065] Examples of antioxidants include vitamin C, sodium vitamin C, vitamin E, rosemary extract, tea extract, and bayberry extract.

[0066] Preservatives include shelf-life enhancers such as mustard extract and lysozyme, nisin, sorbic acid and its salts, and the like.

[0067] Examples of alcoholic beverages include liqueurs, vodka, and shochu.

[0068] The above-mentioned components and the sucrose fatty acid ester of the present invention are emulsified by mixing with water or the like as appropriate and then stirring. The emulsification method is not particularly limited as long as it is a homogeneous emulsification method commonly used for food. Specifically, for example, a method using a homogenizer, a method using a colloid mill, a method using a homomixer, or the like can all be used.

[0069] The homogenization process is usually carried out under heated conditions at 40 to 80°C. It is also preferable to apply high-pressure emulsification as the homogenization process using a homogenizer. A stable beverage can be obtained by performing high-pressure emulsification at a processing pressure of usually 5 MPa or more, preferably 10 MPa or more, more preferably 15 MPa or more, and even more preferably 20 MPa or more, and usually 200 MPa or less, preferably 100 MPa or less, and even more preferably 40 MPa or less, in a single-stage process, or in a multi-stage process such as a two-stage process, in at least one stage of high-pressure emulsification.

[0070] After the homogenization emulsification treatment, a sterilization treatment such as UHT sterilization or retort sterilization is performed. Retort sterilization is usually performed at 110 to 140°C, for example, 121°C, for 10 to 40 minutes. On the other hand, UHT sterilization used for beverages in PET bottles is an ultra-high temperature sterilization at a higher temperature, for example, 120 to 150°C, with a sterilization value (Fo) at 121°C equivalent to 10 to 50. UHT sterilization can be performed by known methods such as direct heating methods such as steam injection, in which steam is directly blown into the beverage, or steam infusion, in which the beverage is heated by injecting it into steam, or indirect heating methods using a surface heat exchanger such as a plate or tube; for example, a plate-type sterilizer can be used.

[0071] Alternatively, a beverage can be produced by incorporating the sucrose fatty acid ester of the present invention into an oil-in-water emulsion that does not contain a coffee component, a tea component, or a cocoa component, mixing the prepared oil-in-water emulsion with a coffee component, a tea component, a cocoa component, or the like, and then performing the above-mentioned homogenization step and sterilization step.

[0072] The sucrose fatty acid ester of the present invention has a less bitter taste and a strong umami flavor, and can therefore be used in coffee, coffee beverages, coffee-containing soft drinks, tea beverages, cocoa beverages, almond beverages, oat beverages, coconut milk, rice milk, cashew nut milk, soy milk, pea milk, fruit juice beverages, walnut beverages, barley milk, and macadamia milk. It is particularly suitable for coffee beverages, tea beverages, almond beverages, and oat beverages, and is particularly suitable for coffee beverages.

[0073] The beverage of the present invention is suitable for use as a packaged beverage, and can be applied to, for example, canned beverages, PET bottled beverages, paper-packaged beverages, bottled beverages, and plastic-packaged beverages.

[0074] 4. Coffee and Tea Beverages Comprising the Sucrose Fatty Acid Ester of the Present Invention Coffee according to the present invention includes liquids containing components derived from coffee beans, such as solutions obtained by extracting ground roasted beans with water or hot water, or liquids obtained by dissolving such solutions in water or the like to form coffee extracts or instant coffees obtained by drying such solutions. The coffee beans used as the raw material for the coffee extract used in the present invention may be either Arabica or Robusta, and are not particularly limited. For example, the raw coffee beans may be selected from Mexico, Guatemala, Blue Mountain, Crystal Mountain, Costa Rica, Colombia, Venezuela, Brazil Santos, Hawaii Kona, Mocha, Kenya, Kilimanjaro, Mandheling, and Robusta, or a mixture of these beans.

[0075] The coffee extract used in the present invention is preferably extracted with 1 L of water per 1 to 100 g, more preferably 20 to 80 g, of coffee beans, and the water temperature during extraction is preferably 60 to 95°C. The extraction time for the coffee extract is preferably 30 to 120 minutes. There are no particular limitations on the extraction method for the coffee extract of the present invention, and extraction can be performed using, for example, the common drip method, immersion method, or espresso method.

[0076] The tea beverages (tea-based beverages) of the present invention are beverages made from tea and non-tea teas, including green tea beverages, black tea beverages, blended tea beverages, oolong tea beverages, and barley tea beverages. The tea beverages of the present invention can be prepared from tea extracts or their concentrates or dilutions produced using methods commonly used to prepare tea extracts. For example, the tea extract used in the present invention can be obtained by mixing tea leaves with water (0-100°C) or by mixing or dissolving a concentrate or purified tea extract, such as tea extract or tea powder, in water (0-100°C). Alternatively, a mixture of the tea extract obtained by mixing tea leaves with water and the above-mentioned tea extract or tea powder may be used as the tea extract in the tea beverage of the present invention. When tea leaves are mixed with water, the tea leaves and the tea extract can be separated using separation means such as centrifugation or filtration. Furthermore, any ingredients other than tea leaves may be blended when preparing the tea extract.

[0077] The content of the sucrose fatty acid ester of the present invention contained in a coffee or tea beverage is preferably high in terms of emulsion stability and bacteriostasis, specifically, preferably 100 ppm or more, more preferably 200 ppm or more, even more preferably 300 ppm or more, and particularly preferably 500 ppm or more. On the other hand, the content of the sucrose fatty acid ester of the present invention is preferably low in terms of flavor, specifically, preferably 3000 ppm or less, more preferably 2000 ppm or less, even more preferably 1500 ppm or less, and particularly preferably 1200 ppm or less.

[0078] The present invention will be specifically explained below with reference to examples, but the present invention is not limited to these examples.

[0079] Production Example 1: 1 mole of sucrose was reacted with 0.05 moles of methyl stearate and 0.2 moles of methyl palmitate. The reaction was carried out using 70% by weight of DMSO as a solvent for 30% by weight of sucrose, methyl stearate, and methyl palmitate. The reaction was carried out under anhydrous conditions using potassium carbonate as a catalyst. The reaction was carried out at 90°C and 2.7 KPa. The by-product lower alcohol was distilled off during the reaction. After completion of the reaction, 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).

[0080] Production Example 2 According to the method of Production Example 1, 1 mole of sucrose was reacted with 0.20 mole of methyl stearate and 0.1 mole of methyl palmitate to obtain sucrose fatty acid ester (powder).

[0081] Production Example 3 According to the method of Production Example 1, 1 mole of sucrose was reacted with 0.67 moles of palmitic acid methyl ester to obtain sucrose fatty acid ester (powder).

[0082] Production Example 4 According to the method of Production Example 1, 1 mole of sucrose was reacted with 0.25 moles of palmitic acid methyl ester to obtain sucrose fatty acid ester (powder).

[0083] Production Example 5 The sucrose fatty acid ester of Production Example 1 was separated under the following conditions, and the liquid with a retention time of 35 minutes was collected and purified by removing the solvent using an evaporator to obtain sucrose palmitate (powder).

[0084] Apparatus: Thermo Fisher U3000 series Column: Inertsil C8 4.6 x 150 mm, 5 μm Column temperature: 40°C Eluent: A (water) B (methanol / THF 9 / 1) A / B = 30 / 70 (0) => 20 / 80 (20) => 0 / 100 (35) => 0 / 100 (50) => 30 / 70 (53) => 30 / 70 (60)

[0085] Production Example 6 The sucrose fatty acid ester of Production Example 1 was separated under the same conditions as in Production Example 5, and the liquid with a retention time of 36.7 minutes was collected. The solvent was removed using an evaporator and the mixture was purified to obtain sucrose stearate (powder).

[0086] Production Examples 7 to 14 The sucrose fatty acid esters of Production Examples 1 to 6 were mixed in the ratios shown in Table 1 to obtain the sucrose fatty acid esters of Production Examples 7 to 14.

[0087]

[0088] The sucrose fatty acid esters of Production Examples 1, 2, and 7 to 11 were subjected to LC-CAD analysis, and the monoester ratio, diester ratio, fatty acid composition of the monoester forms (P form: sucrose monopalmitate, S form: sucrose monostearate), and fatty acid composition of the diester forms (PS form: sucrose palmitate stearate, PP form: sucrose palmitate palmitate, SS form: sucrose stearate stearate) of the sucrose fatty acid esters were quantified.

[0089] <LC-CAD analysis> ・Apparatus: Thermo Fisher U3000 series ・Detector: Corona Veo RS ・Column: Inertsil C8 4.6 x 150 mm, 5 μm ・Column temperature: 40°C ・Eluent: Eluent: A (water) B (methanol / THF 9 / 1) ・A / B = 30 / 70 (0) => 20 / 80 (20) => 0 / 100 (35) => 0 / 100 (50) => 30 / 70 (53) => 30 / 70 (60)

[0090]

[0091] Examples 1 to 5 and Comparative Examples 1 and 2: After adjusting the pH of coffee extract by adding sodium bicarbonate dissolved in hot water, sugar, milk, and the sucrose fatty acid esters of Production Examples 1, 2, and 7 to 11 were added and dissolved to the amounts shown in Table 3, and water was added to bring the total to 100% (by weight). The resulting liquid was heated to 65°C and homogenized at 20 MPa using a high-pressure homogenizer. The liquid was then filled into cans, sealed, and retort sterilized at 121°C for 30 minutes to prepare canned milk coffee. The pH of the beverage after sterilization was 6.6 to 6.8. Ingredients used: Coffee extract: "Coffee Extract COL-19" manufactured by Takasago International Corporation; Milk: Megmilk Snow Brand Co., Ltd.; Sugar: Nissin Sugar Co., Ltd.

[0092] The canned milk coffees obtained were evaluated as follows, and the results are summarized in Table 3.

[0093] [Taste sensor] The taste attributes of the sterilized milk coffee were measured using the electronic taste system ASTREE (manufactured by Alpha MOS) under the following conditions: Sample volume: 25 ml of coffee Data acquisition time: 120 seconds

[0094] The measurement data was analyzed using AlphaSoft (Alpha MOS). Specifically, the average sensor measurement values ​​were quantified on an intensity scale of 0 to 12 according to taste attributes, and the umami and bitterness scores were compared. For both the umami score (NMS) and bitterness score (SCS), 0 indicates the weakest taste and 12 indicates the strongest taste.

[0095] [Sensory Evaluation] Using the pasteurized milk coffee, a trained panel evaluated the flavor of the milk coffee according to the following criteria: Good: Weak bitterness, strong umami; Bad: Strong bitterness, weak umami.

[0096] Stability evaluation Each can of milk coffee was stored at 60°C for 4 weeks, and then left to stand overnight at 5°C. The next day, the cans were opened and the contents were poured into cups, and the occurrence of oil particles and oil-off was visually observed and rated according to the following criteria: 1: Large amounts of cream particles and oil-off present. 2: Slight amounts of cream particles and oil-off present. 3: Very little cream particles and oil-off present. 4: Very little of either cream particles or oil-off present. 5: No cream particles or oil-off present, in good condition.

[0097]

[0098] As shown in Tables 2 and 3, when a sucrose fatty acid ester containing less PS diesters than PP or SS diesters is used, the umami taste is increased and the bitterness is reduced.

[0099] Example 6: Milk coffee was prepared in the same manner as in Example 1, except that the sucrose fatty acid ester of Production Example 12 was used instead of the sucrose fatty acid ester of Production Example 7 used in Example 1, and a sensory evaluation was carried out in the same manner. The stability test was also carried out in the same manner, except that the storage time was changed to 60°C for 2 weeks. The results are shown in Table 4.

[0100]

[0101] As shown in Table 4, when a sucrose fatty acid ester containing less PS diesters than PP or SS diesters is used, a beverage with a strong umami taste and a weak bitterness can be obtained.

[0102] Comparative Examples 3 and 4 Milk coffee was prepared in the same manner as in Example 1, except that the sucrose fatty acid esters of Production Examples 13 and 14 were used instead of the sucrose fatty acid ester of Production Example 7 used in Example 1, and a sensory evaluation was carried out in the same manner. The stability test was also carried out in the same manner, except that the samples were stored at 60°C for 2 weeks. The results are shown in Table 5.

[0103]

[0104] As shown in Table 5, if the diester contained in the sucrose fatty acid ester is only the PP form, the stability is poor.

[0105] Examples 7 and 8 and Reference Examples 1 and 2 To the beverage prepared in Example 2, casein sodium (Tatula 100), succinic acid monoglyceride (Poem B-30), and polyglycerol fatty acid ester (S-10D) were added and dissolved to the amounts shown in Table 6, and water was added to bring the total weight to 100. The resulting liquid was heated to 65°C and homogenized to prepare milk coffee.

[0106] 20 ml of the prepared milk coffee was placed in a glass vial with an inner diameter of 25 mm, and backscattered light was measured using a Turbiscan Tower (Formulation Co., Ltd.). The degree of creaming was evaluated by measuring the increase in backscattered light intensity (ΔB (%)) within 1 mm (39-40 mm) from the top of the liquid surface of the vial containing the prepared milk coffee immediately after dispensing into the vial and after leaving the coffee at 20°C for 12 hours. If the amount of creaming in the milk coffee is high, the backscattered light intensity increases, resulting in a large ΔB (%), which can be considered to be an indication of poor quality. The results are shown in Table 6.

[0107]

[0108] The stability of beverages containing sucrose fatty acid esters with low PS content can be improved by combining them with stabilizers such as succinic acid monoglyceride and sodium caseinate.

[0109] These results indicate that sucrose fatty acid esters with a lower PS content than the PP and SS diesters have a lower bitterness and a higher umami taste when added to food compared to sucrose fatty acid esters with a higher PS content produced by conventional methods. In particular, sucrose fatty acid esters with a PS content of 31% or less of the total diesters have a lower bitterness and a higher umami taste when added to food.

[0110] When the PS-form ratio of the diester of a sucrose fatty acid ester is below a certain level, the adsorption behavior of the sucrose fatty acid ester to the taste buds of the tongue changes, and it is therefore presumed that a beverage containing the sucrose fatty acid ester of the present invention will have a low bitterness and a high umami taste. Specifically, with conventional sucrose fatty acid esters with a high PS-form ratio, the sucrose fatty acid ester adsorbs to the bitter receptors in the taste buds, resulting in a bitter taste, while the sucrose fatty acid ester inhibits the adsorption of umami components in the beverage to the umami receptors in the taste buds, resulting in a poor umami taste. On the other hand, with the sucrose fatty acid ester of the present invention, the sucrose fatty acid ester is less likely to adsorb to the bitter receptors in the taste buds, resulting in a poor bitterness, and the sucrose fatty acid ester is less likely to inhibit the adsorption of umami components in the beverage to the umami receptors in the taste buds, resulting in a strong umami taste.

[0111] The sucrose fatty acid ester of the present invention has reduced bitterness and increased umami when incorporated into foods compared with conventional sucrose fatty acid esters, and is therefore useful as an emulsifier for beverages and the like.

[0112] All prior art documents cited herein are hereby incorporated by reference.

Claims

1. A sucrose fatty acid ester in which at least a portion of the hydroxyl groups of sucrose are substituted with aliphatic hydrocarbon groups, said sucrose fatty acid ester satisfying all of the following (1) to (3): (1) containing sucrose palmitate palmitate and sucrose stearate stearate; (2) the content of sucrose palmitate stearate is equal to or less than the content of sucrose palmitate palmitate; and (3) the content of sucrose palmitate stearate is equal to or less than the content of sucrose stearate stearate.

2. The sucrose fatty acid ester according to claim 1, wherein the sucrose palmitate stearate is present in an amount of 31% or less based on the total amount of diesters.

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

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

5. The sucrose fatty acid ester according to claim 4, wherein the sucrose stearate ester is present in an amount of 15 to 35% based on the total amount of the diester.

6. The sucrose fatty acid ester according to claim 5, wherein the sucrose palmitate is present in an amount of 50% to 90% based on the total amount of the diester.

7. A sucrose fatty acid ester in which at least a portion of the hydroxyl groups of sucrose are substituted with aliphatic hydrocarbon groups, and which satisfies the following (1) and (2): (1) It contains sucrose palmitate palmitate and sucrose stearate stearate. (2) The content of sucrose palmitate stearate is 31% or less of the total amount of diesters.

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

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

10. The sucrose fatty acid ester according to claim 9, wherein the sucrose stearate ester is present in an amount of 15 to 35% based on the total amount of the diester.

11. The sucrose fatty acid ester according to claim 10, wherein the sucrose palmitate is present in an amount of 50% to 90% based on the total amount of the diester.

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

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

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

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