Flavoring agents, their manufacturing methods, and methods for imparting flavor to glycerides

Abstract

This invention provides a flavoring agent based on oils, with improved flavor, particularly a sweet and / or frankincense aroma imparted by lactones having 6 to 14 carbon atoms. A specific amount of lactones having 6 to 14 carbon atoms is generated by oxidizing and heating glycerides containing specific constituent fatty acids at temperatures above 140°C, thereby obtaining a flavoring agent with a sweet and / or frankincense aroma.

Description

Technical Field ,

[0008] , , , ,

[0001] The present invention relates to a flavoring agent containing specific glycerides and lactones, and a method for producing the same. Prior Art

[0002] Fats and oils (lipids) are not only one of the three major nutrients but also an important component for imparting deliciousness to foods. Fats and oils make the taste of foods mild and impart richness. Examples of foods that become delicious due to the presence of fats and oils include tempura, fried foods, ramen, pies, chocolate, cream, and cheese. There are various fats and oils, from fats and oils that are almost odorless like salad oil to fats and oils with unique flavors like baked sesame oil and butter that are highly regarded. These fats and oils are used according to their uses.

[0003] As a method for improving the flavor of fat and oil compositions, particularly butter, a method of enriching lactones in fat and oil compositions in a non-enzymatic manner is known (Patent Document 1). Patent Document 1 specifically discloses a method for producing a fat and oil composition, including the steps of: maintaining a fat and oil composition having a water content of 300 ppm or more and 1200 ppm or less at a temperature at which solid fat exists in the fat and oil composition (preferably 10°C or more and 35°C or less), or adding an additive having the property of forming hydrogen bonds with water molecules to the fat and oil composition and maintaining it at a temperature of 40°C to 60°C, and non-enzymatically generating γ-lactone or δ-lactone from triglycerides containing 4-hydroxy fatty acids or 5-hydroxy fatty acids in the fat and oil composition, and enriching lactones in the method for producing the fat and oil composition.

[0004] In addition, as a method for enhancing the flavor of fats and oils, particularly the basic richness, a method of including a specific amount of a specific coconut oil in fats and oils is known (Patent Document 2). Patent Document 2 specifically discloses a fat and oil containing 0.001% by mass to 15% by mass of virgin coconut oil.

[0005] [Prior Art Documents]

[0006] [Patent Documents]

[0007] [Patent Document 1] Japanese Patent Re-Publication No. 2013 / 105624

[0008] [Patent Document 2] Japanese Patent Application Laid-Open No. 2017-213004 Summary of the Invention Problems to be Solved by the Invention

[0009] However, the manufacturing method in Patent Document 1, as shown in the first invention of Patent Document 1 or Figure 1, requires the presence of 4-hydroxy fatty acids or 5-hydroxy fatty acids. Without these fatty acids, lactones cannot be sufficiently generated. Furthermore, the oil composition in Patent Document 2 contains virgin coconut oil with a large amount of unsaturated fatty acids that contribute to the rancid odor, thus preventing the full appreciation of the lactone aroma in virgin coconut oil.

[0010] The objective of this invention is to provide a flavoring agent based on oils that improves flavor, particularly by providing a sweet and / or frankincense aroma from lactones having 6 to 14 carbon atoms. The means to solve the problem

[0011] The inventors conducted intensive research to solve the aforementioned problem and discovered that by oxidizing and heating glycerides with specific constituent fatty acids at temperatures above 140°C to generate a specific amount of lactones with 6 to 14 carbon atoms, a flavoring agent with a sweet and / or frankincense aroma can be obtained, thus completing the present invention.

[0012] That is, the present invention includes the following states.

[0013] [1] A method for manufacturing a flavoring agent, the method comprising the following steps: subjecting a glycerol ester to oxidative heating treatment at a temperature above 140°C to generate a lactone having 6 to 14 carbons, preparing a flavoring agent containing at least 5 ppm by mass of the lactone having 6 to 14 carbons, wherein at least 10% by mass of the constitutive fatty acids of the glycerol ester are straight-chain saturated fatty acids having 6 to 14 carbons, and the lactone is a γ-lactone and / or a δ-lactone.

[0014] [2] As described in [1], wherein 0% to 5% by mass of the constituent fatty acids of the glycerides are unsaturated fatty acids.

[0015] [3] The method as described in [1] or [2], wherein the constitutive fatty acid of the glyceride is at least 60% by mass of a straight-chain saturated fatty acid having 6 to 14 carbon atoms.

[0016] [4] The method as described in any one of [1] to [3], wherein the constitutive fatty acids of the glycerides comprise only straight-chain saturated fatty acids having 6 to 14 carbon atoms.

[0017] 〔5〕The method according to any one of 〔1〕 to 〔4〕 above, wherein the glyceride is triglyceride.

[0018] 〔6〕The method according to any one of 〔1〕 to 〔5〕 above, comprising the step of: further mixing an additional glyceride after the oxidative heat treatment to prepare a flavoring agent containing 5 mass ppm or more of lactones having 6 to 14 carbon atoms.

[0019] 〔7〕A flavoring agent, containing 80 mass % or more of glyceride and 5 mass ppm or more of lactones having 6 to 14 carbon atoms with respect to the total mass of the flavoring agent. In the flavoring agent, 0 mass % to 5 mass % of the constituent fatty acids of the glyceride are unsaturated fatty acids, 10 mass % or more of the constituent fatty acids of the glyceride are straight-chain saturated fatty acids having 6 to 14 carbon atoms, and the lactone is γ-lactone and / or δ-lactone.

[0020] 〔8〕The flavoring agent according to 〔7〕 above, wherein the glyceride has a peroxide value of 7.5 or more and / or an anisidine value of 1.0 or more.

[0021] 〔9〕The flavoring agent according to 〔7〕 or 〔8〕 above, wherein 60 mass % or more of the constituent fatty acids of the glyceride are straight-chain saturated fatty acids having 6 to 14 carbon atoms.

[0022] 〔10〕The flavoring agent according to any one of 〔7〕 to 〔9〕 above, wherein the constituent fatty acids of the glyceride contain only straight-chain saturated fatty acids having 6 to 14 carbon atoms.

[0023] 〔11〕The flavoring agent according to any one of 〔7〕 to 〔10〕 above, wherein the glyceride is triglyceride.

[0024] 〔12〕The flavoring agent according to any one of 〔7〕 to 〔11〕 above has a sweet fragrance and / or a milky fragrance.

[0025] 〔13〕A method for imparting flavor to a glyceride, the method comprising the steps of: subjecting the glyceride to an oxidative heat treatment at 140 °C or higher to generate 5 mass ppm or more of lactones having 6 to 14 carbon atoms, 10 mass % or more of the constituent fatty acids of the glyceride being straight-chain saturated fatty acids having 6 to 14 carbon atoms, and the lactone being γ-lactone and / or δ-lactone. Advantages of the Invention

[0026] According to the present invention, a flavoring agent based on oils and fats, with improved flavor, particularly sweet and / or frankincense aromas from lactones having carbon numbers of 6 to 14, can be provided. Simple Explanation of the Diagram

[0027] Figure 1 shows the analysis results of the time when the sample temperature reached 180°C after heating the raw material glyceride (ODO) to 180°C and the amount of lactone generated. Implementation

[0028] This invention relates to a method for manufacturing a flavor-imparting agent, the method comprising the following steps: subjecting a glycerol ester to oxidative heating treatment at a temperature above 140°C to generate a lactone having 6 to 14 carbon atoms, preparing a flavor-imparting agent containing at least 5 ppm by mass of the lactone having 6 to 14 carbon atoms, wherein at least 10% by mass of the constituting fatty acids of the glycerol ester are straight-chain saturated fatty acids having 6 to 14 carbon atoms, and the lactone is a γ-lactone and / or a δ-lactone.

[0029] In the glycerides used as raw materials, at least 10% by mass, for example, at least 30% by mass, at least 60% by mass, at least 75% by mass, at least 90% by mass, or all (100% by mass) of the constituting fatty acids are straight-chain saturated fatty acids with 6 to 14 carbon atoms. The straight-chain saturated fatty acids with 6 to 14 carbon atoms can be one type or two or more types. Examples of straight-chain saturated fatty acids with 6 to 14 carbon atoms include: hexanoic acid, caprylic acid, decanoic acid, lauric acid, myristic acid, etc., preferably caprylic acid and / or decanoic acid, or lauric acid and / or myristic acid. More preferably caprylic acid and / or decanoic acid, and most preferably caprylic acid. By using at least 10% by mass of straight-chain saturated fatty acids with 6 to 14 carbon atoms as constituting fatty acids, the required amount of lactones with 6 to 14 carbon atoms can be generated. Furthermore, the amount of lactone formed is extremely small compared to the amount of fatty acids constituting glycerides. Therefore, the amount of glycerides or the proportion of constituting fatty acids (mass ratio) is almost unaffected by the formation of lactones from fatty acids. Thus, the amount of glycerides or the mass ratio of constituting fatty acids remains essentially the same before and after the oxidative heat treatment.

[0030] When glycerides contain unsaturated fatty acids other than straight-chain saturated fatty acids with 6 to 14 carbon atoms, the rancid odor produced by the oxidation of unsaturated fatty acids may be added to the flavor enhancers; therefore, it is preferable that the amount of unsaturated fatty acids is small. For example, it is preferable that 0% to 5% by mass of the fatty acids constituting the glycerides are unsaturated fatty acids, more preferably 0% to 3% by mass. When unsaturated fatty acids are included, they are preferably straight-chain unsaturated fatty acids with 16 to 22 carbon atoms that constitute vegetable oils, more preferably one or more selected from oleic acid, linolenic acid, alpha-linolenic acid, and erucic acid.

[0031] The raw material glycerides may contain one or more of monoglycerides, diglycerides, or triglycerides, preferably 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, 95% by mass or more, or 100% by mass of triglycerides. These raw material glycerides can be obtained by esterification of fatty acids with glycerol, transesterification of fatty acid esters with glycerol, or transesterification of fatty acids with oils or fats, or transesterification of methyl or ethyl esters of fatty acids with glycerol or oils. Additionally, in cases containing unsaturated fatty acids, hydrogenation can be performed on the fatty acids, methyl or ethyl esters of fatty acids, or glycerides to reduce the number of unsaturated bonds. Hydrogenated coconut oil or palm kernel oil may also be used. Furthermore, other oils can be mixed within the range where more than 10% by mass of the fatty acids constituting the raw material glycerides are straight-chain saturated fatty acids with 6 to 14 carbon atoms. These include coconut oil, palm kernel oil, palm oil, palm fractionated oil (palm oil essence, palm super oil essence, palm middle fraction, palm stearin, etc.), shea butter, shea butter fractionated oil, shorea (sal) butter, shorea tree fractionated oil, shorea resin (illipe butter), soybean oil, rapeseed oil, cottonseed oil, safflower oil, sunflower oil, rice oil, corn oil, sesame oil, olive oil, perilla oil, linseed oil, peanut oil, dairy fat, cocoa butter, and other animal and vegetable oils or blends thereof, processed oils, etc.

[0032] As a raw material, refined glycerides are preferred for consumption, but refined and unrefined glycerides can also be used together. From the viewpoint of the flavor imparted by the obtained flavor agent, the content of unrefined glycerides relative to the total mass of the raw material glycerides is preferably 0% to 20% by mass, more preferably 0% to 10% by mass, and even more preferably 0% to 5% by mass. Refining processes for consumption include degumming, deoxidation, decolorization, and deodorization.

[0033] The temperature for the oxidative heat treatment of the raw material glycerides only needs to be the temperature at which lactones with 6 to 14 carbon atoms are formed, which is above 140°C, preferably 150°C to 250°C, more preferably 160°C to 225°C, and even more preferably 170°C to 200°C. The heating time depends on the heating temperature, but only needs to be sufficient to oxidize the raw material glycerides and form lactones. For example, when the heating temperature is above 180°C, the raw material glycerides can be heated for more than 5 minutes after reaching 180°C, preferably 10 to 120 minutes, 20 to 90 minutes, or 45 to 75 minutes. Alternatively, for example, when the heating temperature is between 160°C and 180°C, the raw material glycerides can be heated for more than 10 minutes after reaching 160°C, preferably 15 to 160 minutes or 30 to 120 minutes. Additionally, for example, when the heating temperature is 140°C to 160°C, the raw material glycerol ester can be heated for more than 15 minutes after reaching 140°C, preferably for 90 to 180 minutes or 90 to 160 minutes. As for the heat treatment conditions, there are no particular limitations as long as they are conditions that can oxidize the raw material glycerol ester and generate lactone, but it is preferable to heat the raw material glycerol ester in the presence of oxygen, such as in the atmosphere.

[0034] By means of oxidative heating treatment, lactones with a number of carbons corresponding to the constituent fatty acids in the raw glycerides are generated. In the method of the present invention, lactones with 6 to 14 carbons are generated, more preferably 8 to 14 carbons, even more preferably 8 to 10 carbons, and even more preferably 8 carbons.

[0035] In the method of the present invention, the content of lactones with carbon numbers 6 to 14 in the flavor-imparting agent is 5 ppm or more, preferably 15 ppm or more, 30 ppm or more, 60 ppm or more, 90 ppm or more, 120 ppm or more, 150 ppm or more, 200 ppm or more, 250 ppm or more, or 300 ppm or more. The content of lactones with carbon numbers 6 to 14 in the flavor-imparting agent can, for example, be less than 600 ppm, less than 500 ppm, less than 400 ppm, or less than 350 ppm. With a lactone content of 5 ppm or more, the flavor-imparting agent exhibits a sweet aroma and / or a frankincense aroma. As long as lactones with carbon numbers 6 to 14 are generated in this range, lactones with carbon numbers 5 or less or more than 15 can be generated.

[0036] As lactones with 6 to 14 carbon atoms, γ-lactones and / or δ-lactones with stable structures are formed. The mass ratio (γ:δ) of γ-lactones with 6 to 14 carbon atoms is not particularly limited, and can be, for example, 100:0 to 0:100. Alternatively, for example, in the case of γ-lactones with 6 to 10 carbon atoms, the mass ratio (γ:δ) of γ-lactones can be 90:10 to 10:90, 80:20 to 20:80, 70:30 to 30:70, 60:40 to 40:60, or 55:45 to 45:55. For example, in the case of the mass ratio (γ:δ) of γ-lactone to δ-lactone with carbon numbers of 11 to 14, it can be 50:50 to 0:100, 40:60 to 0:100, 30:70 to 0:100, 20:80 to 0:100, 10:90 to 0:100, or 5:95 to 0:100.

[0037] The method of the present invention may also include a step of further mixing an additional glycerol ester after the oxidative heat treatment of the raw glycerol ester to prepare a flavoring agent containing at least 5 ppm of lactones with carbon numbers 6 to 14. Previously known mixing methods may be used without particular limitation in mixing the additional glycerol ester. The additional glycerol ester may be the same as or different from the raw glycerol ester, and may be any glycerol ester as long as it is commonly added to food. The amount of the additional glycerol ester mixed is not particularly limited as long as it contains at least 5 ppm of lactones with carbon numbers 6 to 14 generated by the oxidative heat treatment in the final flavoring agent.

[0038] Furthermore, this invention relates to a method for imparting flavor to glycerides, the method comprising the steps of: subjecting the glycerides to an oxidative heat treatment at a temperature above 140°C to generate at least 5 ppm by mass of a lactone having 6 to 14 carbon atoms, wherein at least 10% by mass of the constituting fatty acids of the glycerides are straight-chain saturated fatty acids having 6 to 14 carbon atoms, and the lactone is a γ-lactone and / or a δ-lactone. The conditions for the oxidative heat treatment, including the raw glycerides or the generated 6- to 14 carbon-carbon lactones, are the same as those related to the method for manufacturing the flavor-imparting agent.

[0039] Furthermore, the present invention relates to a flavoring agent comprising, relative to the total mass of the flavoring agent, at least 80% by mass of a glycerol ester and at least 5 ppm of a lactone having 6 to 14 carbon atoms. In the flavoring agent, 0% to 5% by mass of the constituting fatty acids of the glycerol ester are unsaturated fatty acids, at least 10% by mass of the constituting fatty acids of the glycerol ester are straight-chain saturated fatty acids having 6 to 14 carbon atoms, and the lactone is a γ-lactone and / or a δ-lactone.

[0040] The glycerides contained in the flavor-imparting agent may be included in the product of the oxidation and heating of the raw material glycerides, and may optionally include the additional glycerides. The glycerides contained in the flavor-imparting agent constitute 10% or more, for example 30% or more, 60% or more, 80% or more, 90% or more, or all (100% by mass) of straight-chain saturated fatty acids having 6 to 14 carbon atoms. The straight-chain saturated fatty acids having 6 to 14 carbon atoms may be one type or two or more types. Examples of straight-chain saturated fatty acids having 6 to 14 carbon atoms include: hexanoic acid, caprylic acid, decanoic acid, lauric acid, myristic acid, etc., preferably caprylic acid and / or decanoic acid, or lauric acid and / or myristic acid. More preferably caprylic acid and / or decanoic acid, and most preferably caprylic acid.

[0041] When the glycerides contain unsaturated fatty acids other than straight-chain saturated fatty acids with 6 to 14 carbon atoms, the rancid odor produced by the oxidation of unsaturated fatty acids may be added to the flavor enhancer. Therefore, it is preferable to use a small amount of unsaturated fatty acids. In the flavor enhancer of the present invention, it is preferable that 0% to 5% by mass of the fatty acids constituting the glycerides are unsaturated fatty acids, more preferably 0% to 3% by mass. When unsaturated fatty acids are included, they are preferably straight-chain unsaturated fatty acids with 16 to 22 carbon atoms that constitute vegetable oils, more preferably one or more selected from oleic acid, linolenic acid, alpha-linolenic acid, and erucic acid.

[0042] The flavoring agent may contain glycerides obtained through esterification of fatty acids with glycerol, transesterification of fatty acid esters with glycerol, or transesterification of fatty acids with oils or fats, or transesterification of methyl or ethyl esters of fatty acids with glycerol or oils. Additionally, in cases where unsaturated fatty acids are included, hydrogenation of the fatty acids, methyl or ethyl esters of fatty acids, or glycerides can reduce the number of unsaturated bonds. Hydrogenated coconut oil or palm kernel oil may also be used. Furthermore, other oils, such as coconut oil, palm kernel oil, palm oil, palm fractionated oil (palm oil essence, palm super oil essence, palm middle fraction, palm stearin, etc.), shea butter, shea butter fractionated oil, bromelain, bromelain, bromelain, soybean oil, rapeseed oil, cottonseed oil, safflower oil, sunflower oil, rice oil, corn oil, sesame oil, olive oil, perilla oil, linseed oil, peanut oil, dairy fat, cocoa butter, etc., or blends and processed oils, can be mixed within the range where more than 10% by mass of the fatty acids constituting the glycerides contained in the flavoring agent are straight-chain saturated fatty acids with carbon numbers of 6 to 14.

[0043] The flavoring agent contains glycerides that may include one or more of monoglycerides, diglycerides, or triglycerides, preferably 50% or more, 60% or more, 70% or more, 80% or more, 90% or more, 95% or more, or 100% by mass of triglycerides.

[0044] The flavoring agent of the present invention is preferably a glycerol ester comprising an oxidative heat treatment as described in the manufacturing method of the flavoring agent. The degree of oxidation of the glycerol ester is represented by the peroxide value and the methoxyaniline value, which increase through oxidation.

[0045] The glycerides contained in the flavor-improving agent preferably have a peroxide value of 7.5 or higher. More preferably, the glycerides contained in the flavor-improving agent have a peroxide value of 10-100, 15-90, 20-80, 25-70, or 30-60. A peroxide value of 7.5 or higher for the glycerides confirms that they have undergone oxidation to a certain level. The peroxide value can be determined according to the Standard Oil and Fat Analysis Test Method (edited by the Japan Oil Chemistry Society) 2.5.2.1-2013 "Peroxide Value (Acetic Acid-Isooctane Method)".

[0046] Furthermore, through oxidative heating treatment, another oxidation indicator, the methoxyaniline value, also increases. The glycerides contained in the flavoring agent may have a methoxyaniline value of 0.8 or higher, preferably 1.0 or higher. More preferably, the glycerides contained in the flavoring agent may also have methoxyaniline values ​​of 0.9–10.0, 1.0–8.0, 1.5–6.0, 2.0–5.5, 2.5–5.0, or 3.0–4.5. A methoxyaniline value of 0.8 or higher for the glycerides confirms that they have undergone oxidation to a certain level. The methoxyaniline value can be determined according to the Standard Oil and Fat Analysis Test Method (Japan Oil Chemistry Society) 2.5.3-2013 "Methoxyaniline Value".

[0047] Furthermore, in the same oxidative heat treatment, the peroxide value tends to increase in the case of straight-chain saturated fatty acids with 6 to 10 carbon atoms, and the methoxyaniline value tends to increase in the case of straight-chain saturated fatty acids with 11 to 14 carbon atoms. The glycerides contained in the flavor-imparting agent preferably have a peroxide value of 7.5 or higher and / or a methoxyaniline value of 1.0 or higher. When the straight-chain saturated fatty acids with 6 to 10 carbon atoms are used as glycerides constituting fatty acids, it is more preferably that they have a peroxide value selected from any range of 10 to 100, 15 to 90, 20 to 80, 25 to 70, and 30 to 60, and more preferably that they have a methoxyaniline value selected from any range of 1.0 to 8.0, 1.5 to 6.0, 2.0 to 5.5, 2.5 to 5.0, and 3.0 to 4.5. Furthermore, when the straight-chain saturated fatty acid with 11 to 14 carbon atoms is set as a glycerol ester constituting the fatty acid, it is more preferable to have a methoxyaniline valence selected from any range of 1.0 to 8.0, 1.0 to 6.0, 1.0 to 5.0, 1.0 to 4.0, 1.0 to 3.0, or 1.0 to 2.0.

[0048] The content of glycerides in the flavoring agent is 80% by mass or more relative to the total mass of the flavoring agent, preferably 85% by mass or more, 90% by mass or more, 95% by mass or more, or 99% by mass or more. If the content of glycerides is within the aforementioned range, it has a sufficient effect as a base material for flavoring agents.

[0049] The flavoring agent contains γ-lactones and / or δ-lactones with carbon numbers 6 to 14, which may also be included in the product of the oxidation and heating of the raw material glycerides. The content of γ-lactones with carbon numbers 6 to 14 in the flavoring agent is 5 ppm or more relative to the total mass of the flavoring agent, preferably 15 ppm or more, 30 ppm or more, 60 ppm or more, 90 ppm or more, 120 ppm or more, 150 ppm or more, 200 ppm or more, 250 ppm or more, or 300 ppm or more. Alternatively, the content of γ-lactones with carbon numbers 6 to 14 in the flavoring agent may be, for example, less than 600 ppm, less than 500 ppm, less than 400 ppm, or less than 350 ppm. With a γ-lactone content of 5 ppm or more, the flavoring agent exhibits a sweet and / or frankincense aroma.

[0050] The mass ratio (γ:δ) of γ-lactones with carbon numbers 6 to 14 to δ-lactones contained in flavor-imparting agents is not particularly limited, and can be, for example, 100:0 to 0:100. Alternatively, for example, in the case of γ-lactones with carbon numbers 6 to 10 to δ-lactones, the mass ratio (γ:δ) can be 90:10 to 10:90, 80:20 to 20:80, 70:30 to 30:70, 60:40 to 40:60, or 55:45 to 45:55. For example, in the case of γ-lactones with carbon numbers 11 to 14 to δ-lactones, the mass ratio (γ:δ) can be 50:50 to 0:100, 40:60 to 0:100, 30:70 to 0:100, 20:80 to 0:100, 10:90 to 0:100, or 5:95 to 0:100.

[0051] According to the present invention, a flavoring agent having a sweet aroma and / or a frankincense aroma is provided. "Sweet aroma" refers to the aroma derived from γ-lactones and / or δ-lactones having carbon numbers 6 to 10. "Frankincense aroma" refers to the aroma derived from γ-lactones and / or δ-lactones having carbon numbers 11 to 14.

[0052] Flavor enhancers may contain any other ingredients typically added to food, provided that the sweet and / or frankincense flavor is not impaired. Examples of such other ingredients include: emulsifiers, antioxidants, alcohols, water, pH adjusters, flavorings, colorings, fragrances, defoamers, sugars, sugar alcohols, and stabilizers. Examples of emulsifiers include: polyglycerol fatty acid esters, polyglycerol condensed castor oil esters, sorbitan fatty acid esters, sorbitol fatty acid esters, sucrose fatty acid esters, propylene glycol fatty acid esters, organic acid monoglycerides, polysorbate esters, and lecithin. Examples of antioxidants include: tocopherols, tocotrienols, carotenoids, polyphenols, ascorbic acid, and ascorbic acid derivatives.

[0053] [Example]

[0054] (Raw material: glyceryl ester)

[0055] The following are used as raw material glycerides.

[0056] ODO (Medium-Chain Triglycerides, manufactured by Nisshin OilliO Group Co., Ltd., composed of fatty acids: 75% caprylic acid and 25% capric acid)

[0057] ODO+Toc (a sample in which 500 ppm of soybean-derived tocopherols are added to ODO)

[0058] C10R (Medium-Chain Fatty Acid Triglyceride, manufactured by Nisshin OilliO Group Co., Ltd., composed of fatty acids: 30% caprylic acid and 70% capric acid)

[0059] Caprylic / caprylic triglyceride (a medium-chain triglyceride manufactured by Nisshin OilliO Group Co., Ltd., composed of approximately 100% caprylic acid)

[0060] Tridecanoic acid glyceride (a medium-chain triglyceride manufactured by Nisshin OilliO Group Co., Ltd., whose constituent fatty acids are approximately 100% capric acid)

[0061] Trilaurin (manufactured by Tokyo Chemical Industry Co., Ltd., composed of fatty acids: approximately 98% lauric acid)

[0062] Trimyristin (manufactured by Tokyo Chemical Industry Co., Ltd., its constituent fatty acids: approximately 95% myristic acid)

[0063] (Oxidation heat treatment)

[0064] 50.00 g of ODO was taken as a sample in a 200 mL beaker and heated at 180 °C under ambient temperature using a heating mantle with PID temperature control. A sweet aroma began to develop when the sample temperature exceeded approximately 140 °C. Immediately after 0, 5, 15, 30, and 60 minutes from when the sample temperature reached 180 °C, the sample was transferred to a nitrogen-purified brown bottle, capped, and left to stand at 20 °C.

[0065] For ODO+Toc, C10R, tricaprylic acid glyceride, tricaprylic acid glyceride, trilaurylic acid glyceride, and trimyristate glyceride, the samples were transferred to brown bottles 60 minutes after the temperature reached 180°C, and otherwise treated in the same way as ODO.

[0066] (analyze)

[0067] For untreated ODO, trilaurate and trimyristic acid glycerides, as well as for treated samples, the peroxide value (POV) was determined according to the Standard Oil Analysis Test Method (edited by the Japan Oil Chemistry Society) 2.5.2.1-2013 "Peroxide Value (Acetic Acid-Isooctane Method)".

[0068] For untreated ODO, trilaurate and trimyristic acid, as well as for treated samples, the methoxyaniline value (AnV) was determined according to the Standard Oil Analysis Test Method (Japan Oil Chemistry Society) 2.5.3-2013 "Methoxyaniline Value".

[0069] For untreated ODO, trilaurate and trimyristic acid glycerides, as well as the treated samples, the lactone content was determined by GC / MS under the following conditions.

[0070] GC / MS conditions

[0071] .Tube string: DB-1HT (15m × Φ0.25mm × 0.1μm)

[0072] Heating conditions: 40℃ [3 minutes] - 4℃ / minute - 170℃ - 25℃ / minute - 370℃ [7 minutes]

[0073] Carrier gas: Helium

[0074] Inlet temperature: 370℃, split ratio: 20:1

[0075] Ion source: EI

[0076] Detector: MSD

[0077] Solution concentration: 0.1 mg / mL

[0078] Injection volume: 1 μL

[0079] Analysis method: Quantification (ppm) was performed using C8-C14 lactone STD solution as an external standard.

[0080] The analytical results of peroxide value (POV) and methoxyaniline value (AnV) are shown in Table 1, and the analytical results of lactone content are shown in Table 1 and Figure 1.

[0081] [Table 1]

[0082] No lactones were identified in untreated ODO, trilaurate, trimyristic acid, and ODO+Toc with added tocopherol as an antioxidant. Furthermore, in the samples after oxidative heat treatment, lactones were found only in those with 8, 10, 12, and / or 14 carbon atoms, corresponding to the carbon number of the constituent fatty acids of the raw glycerides. Additionally, the amount of glycerides or the mass ratio of the constituent fatty acids remained substantially unchanged before and after the oxidative heat treatment.

[0083] (Fragrance rating 1)

[0084] Ten sensory inspectors evaluated the aroma of untreated ODO and oxidized / heat-treated ODO, ODO+Toc, C10R, tricaprylic acid glyceride, and tricaprylic acid glyceride samples (20°C) according to the following criteria. The aroma of sample 2 was assigned a score of 2 for relative evaluation. The results (average scores) are shown in Table 2.

[0085] 0 points: No sweet aroma.

[0086] 1 point: I could detect a faint sweet aroma (weaker than sample 2).

[0087] 2 points: I could smell a sweet aroma (same as sample 2).

[0088] 3 points: The sweet aroma was slightly strong (stronger than sample 2, but not more than twice as strong).

[0089] 4 points: I strongly felt the sweet aroma (about twice as strong as sample 2).

[0090] 5 points: The sweet aroma was quite strong (about twice as strong as that of sample 2).

[0091]

[0092] Eight-carbon lactones are formed from eight-carbon fatty acids (octanoic acid), while ten-carbon lactones are formed from ten-carbon fatty acids (decanoic acid). The intensity of the sweet aroma was found to be related to the amount of lactones produced.

[0093] (Fragrance rating 2)

[0094] For each sample (20°C) of untreated trilaurate and trimyristic glycerides, and oxidized and heat-treated trilaurate and trimyristic glycerides, the presence or absence of frankincense was evaluated by 10 functional examiners according to the following criteria. The results (average scores) are shown in Table 3.

[0095] 0 points: No frankincense.

[0096] 1 point: I could smell the aroma of frankincense.

[0097]

[0098] 12-carbon lactones are formed from 12-carbon fatty acids (lauric acid), while 14-carbon lactones are formed from 14-carbon fatty acids (myristic acid). Samples containing 12-carbon or 14-carbon lactones have a frankincense aroma.

[0099] [Industrial Applicability]

[0100] The flavoring agent provided by this invention can be used to impart flavor to food.

Claims

1. A method for manufacturing a flavoring agent, comprising the following steps: subjecting a glycerol ester to oxidative heat treatment at a temperature above 140°C to generate a lactone having 6 to 14 carbon atoms; preparing a flavoring agent containing at least 5 ppm by mass of the lactone having 6 to 14 carbon atoms; wherein at least 10% by mass of the constituting fatty acids of the glycerol ester subjected to the oxidative heat treatment are straight-chain saturated fatty acids having 6 to 14 carbon atoms and 0% to 5% by mass are unsaturated fatty acids, or at least 30% by mass of the constituting fatty acids of the glycerol ester subjected to the oxidative heat treatment are straight-chain saturated fatty acids having 6 to 14 carbon atoms, wherein the lactone is a γ-lactone and / or a δ-lactone.

2. A method for manufacturing the flavor-imparting agent as described in claim 1, comprising: After the aforementioned oxidative heat treatment, additional glycerides are further mixed to prepare a flavor enhancer containing at least 5 ppm by mass of lactones with 6 to 14 carbon atoms.

3. A method for manufacturing a flavoring agent, comprising the following steps: subjecting a glycerol ester to oxidative heat treatment at a temperature above 140°C to generate a lactone having 6 to 14 carbon atoms; further mixing an additional glycerol ester after the oxidative heat treatment to prepare a flavoring agent containing at least 5 ppm by mass of the lactone having 6 to 14 carbon atoms, wherein at least 10% by mass of the constituting fatty acids of the glycerol ester subjected to the oxidative heat treatment are straight-chain saturated fatty acids having 6 to 14 carbon atoms, and the lactone is a γ-lactone and / or a δ-lactone.

4. A method for manufacturing a flavoring agent as claimed in any one of claims 1 to 3, wherein 0% to 5% by mass of the constituent fatty acids of the glycerol ester subjected to the oxidative heat treatment are unsaturated fatty acids.

5. A method for manufacturing a flavoring agent as claimed in any one of claims 1 to 3, wherein the constitutive fatty acids of the glycerol ester subjected to the oxidative heat treatment comprise at least 60% by mass of straight-chain saturated fatty acids having 6 to 14 carbon atoms.

6. A method for manufacturing a flavoring agent as claimed in any one of claims 1 to 3, wherein the constitutive fatty acids of the glycerides subjected to the oxidative heat treatment comprise only straight-chain saturated fatty acids having 6 to 14 carbon atoms.

7. A method for manufacturing a flavor-imparting agent as claimed in any one of claims 1 to 3, wherein the glycerol ester subjected to the oxidative heat treatment is a triglyceride.

8. A flavoring agent comprising, relative to the total mass of the flavoring agent, at least 80% by mass of a glycerol ester and at least 5 ppm by mass of a lactone having 6 to 14 carbon atoms, wherein, in the flavoring agent, 0% to 5% by mass of the constituting fatty acids of the glycerol ester are unsaturated fatty acids, at least 10% by mass of the constituting fatty acids of the glycerol ester are straight-chain saturated fatty acids having 6 to 14 carbon atoms, and the lactone is a γ-lactone and / or a δ-lactone.

9. The flavoring agent as claimed in claim 8, wherein the glycerol ester has a peroxide value of 7.5 or higher and / or a methoxyaniline value of 1.0 or higher.

10. The flavor-imparting agent as claimed in claim 8 or claim 9, wherein the constitutive fatty acid of the glyceride comprises at least 60% by mass of a straight-chain saturated fatty acid having 6 to 14 carbon atoms.

11. The flavor-imparting agent as claimed in claim 8 or claim 9, wherein the constituent fatty acids of the glycerol ester comprise only straight-chain saturated fatty acids having 6 to 14 carbon atoms.

12. The flavor-imparting agent as claimed in claim 8 or claim 9, wherein the glyceride is a triglyceride.

13. The flavoring agent as described in claim 8 or claim 9, having a sweet and / or frankincense aroma.

14. A method for imparting flavor to glycerides, comprising the steps of: subjecting the glycerides to oxidative heat treatment at a temperature above 140°C to generate at least 5 ppm by mass of lactones having 6 to 14 carbons, wherein at least 10% by mass of the constitutive fatty acids of the glycerides are straight-chain saturated fatty acids having 6 to 14 carbons and 0% to 5% by mass are unsaturated fatty acids, or wherein at least 30% by mass of the constitutive fatty acids of the glycerides subjected to the oxidative heat treatment are straight-chain saturated fatty acids having 6 to 14 carbons, wherein the lactones are γ-lactones and / or δ-lactones.

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