Flavoring agent and method for producing the same

Abstract

To provide a flavor-imparting agent which is based on oils and fats and has an improved flavor, particularly a sweet flavor and / or a milky flavor of a lactone having 6 to 14 carbon atoms.SOLUTION: A flavor-imparting agent having a sweet flavor and / or a milky flavor can be produced by subjecting a glyceride having a specific constituent fatty acid to oxidization by heating at 140°C or higher to produce a specific amount of a lactone having 6 to 14 carbon atoms.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to a flavoring agent containing a specific glyceride and a lactone, and a method for producing the same. [Background technology]

[0002] Fats and oils (lipids) are not only one of the three major nutrients, but also an important component that gives food its deliciousness. Fats and oils make food taste milder and richer. Examples of foods that taste better because of fats and oils include tempura, fried foods, ramen, pies, chocolate, cream, and cheese. There are a wide variety of fats and oils, ranging from nearly tasteless and odorless oils like salad oil to oils valued for their unique flavors like roasted sesame oil and butter. These fats and oils are used according to their purpose.

[0003] A method for non-enzymatically enriching an oil or fat composition with lactones is known as a method for improving the flavor of an oil or fat composition, particularly butter (Patent Document 1). Specifically, Patent Document 1 discloses a method for producing an oil or fat composition enriched in lactones, which includes the steps of: maintaining an oil or fat composition having a water content of 300 ppm to 1200 ppm at a temperature (preferably 10°C to 35°C) at which solid fat is present in the oil or fat composition; or adding an additive capable of forming hydrogen bonds with water molecules to the oil or fat composition; and maintaining the oil or fat composition at a temperature of 40 to 60°C to non-enzymatically produce γ-lactone or δ-lactone from triglycerides containing 4- or 5-hydroxy fatty acids in the oil or fat composition.

[0004] Furthermore, a method for enhancing the flavor of fats and oils, particularly the base richness, is known in which a specific amount of a specific coconut oil is added to the fat and oil (Patent Document 2). Specifically, Patent Document 2 discloses fats and oils containing 0.001 to 15% by mass of virgin coconut oil. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Re-tabled publication No. 2013 / 105624 [Patent Document 2] Japanese Patent Application Laid-Open No. 2017-213004 Summary of the Invention [Problem to be solved by the invention]

[0006] However, the production method of Patent Document 1 requires the presence of 4- or 5-hydroxy fatty acids, as shown in Claim 1 and Figure 1 of Patent Document 1, and lactones are not produced sufficiently in the absence of these fatty acids. Also, the virgin coconut oil contained in the oil and fat composition of Patent Document 2 contains a large amount of unsaturated fatty acids that cause rancidity, so the aroma of lactones in the virgin coconut oil is not fully perceived.

[0007] An object of the present invention is to provide a flavor enhancer based on fats and oils, which has an improved flavor, and in particular has a sweet and / or milky flavor exhibited by lactones having 6 to 14 carbon atoms. [Means for solving the problem]

[0008] As a result of intensive research to solve the above-mentioned problems, the present inventors have found that a flavor enhancer having a sweet aroma and / or a milky aroma can be obtained by oxidatively heating a glyceride having specific constituent fatty acids at 140°C or higher to produce a specific amount of lactone having 6 to 14 carbon atoms, thereby completing the present invention.

[0009] That is, the present invention includes the following aspects. [1] A method for producing a flavor imparting agent, The method includes a step of subjecting a glyceride to oxidative heat treatment at 140°C or higher to generate a lactone having 6 to 14 carbon atoms, and preparing a flavor-imparting agent containing the lactone having 6 to 14 carbon atoms in an amount of 5 ppm by mass or more, 10% by mass or more of the constituent fatty acids of the glyceride are straight-chain saturated fatty acids having 6 to 14 carbon atoms, The lactone is a gamma lactone and / or a delta lactone. method. [2] The method according to [1] above, wherein 0 to 5% by mass of the constituent fatty acids of the glyceride are unsaturated fatty acids. [3] The method according to [1] or [2] above, wherein 60% by mass or more of the constituent fatty acids of the glyceride are straight-chain saturated fatty acids having 6 to 14 carbon atoms. [4] The method according to any one of [1] to [3] above, wherein the constituent fatty acids of the glyceride consist solely of linear saturated fatty acids having 6 to 14 carbon atoms. [5] The method according to any one of [1] to [4] above, wherein the glyceride is a triglyceride. [6] The method according to any one of [1] to [5], further comprising a step of mixing additional glyceride after the oxidative heat treatment to prepare a flavor-imparting agent containing 5 ppm by mass or more of a lactone having 6 to 14 carbon atoms. [7] A flavor imparting agent containing 80% by mass or more of a glyceride and 5 ppm or more of a lactone having 6 to 14 carbon atoms, based on the total mass of the flavor imparting agent, 0 to 5% by mass of the constituent fatty acids of the glyceride are unsaturated fatty acids, 10% by mass or more of the constituent fatty acids of the glyceride are straight-chain saturated fatty acids having 6 to 14 carbon atoms, A flavor-imparting agent, wherein the lactone is a gamma lactone and / or a delta lactone. [8] The flavor enhancer according to [7], wherein the glyceride has a peroxide value of 7.5 or more and / or an anisidine value of 1.0 or more. [9] The flavor enhancer according to [7] or [8], wherein 60% by mass or more of the constituent fatty acids of the glyceride are straight-chain saturated fatty acids having 6 to 14 carbon atoms.

[10] The flavor enhancer according to any one of [7] to [9], wherein the constituent fatty acids of the glyceride consist solely of linear saturated fatty acids having 6 to 14 carbon atoms.

[11] The flavor enhancer according to any one of [7] to

[10] above, wherein the glyceride is a triglyceride.

[12] The flavor enhancer according to any one of [7] to

[11] above, which has a sweet scent and / or a milky scent.

[13] A method for imparting flavor to glycerides, comprising: The method includes a step of subjecting a glyceride to oxidative heat treatment at 140°C or higher to produce 5 ppm by mass or more of lactones having 6 to 14 carbon atoms, 10% by mass or more of the constituent fatty acids of the glyceride are straight-chain saturated fatty acids having 6 to 14 carbon atoms, The lactone is a gamma lactone and / or a delta lactone. method. [Effects of the Invention]

[0010] According to the present invention, it is possible to provide a flavor enhancer based on oils and fats, which has an improved flavor, and in particular has a sweet scent and / or a milky scent exhibited by lactones having 6 to 14 carbon atoms. [Brief explanation of the drawings]

[0011]

Figure 1

[0012] The present invention relates to a method for producing a flavor-imparting agent, which includes a step of subjecting a glyceride to oxidative heat treatment at 140°C or higher to generate a lactone having 6 to 14 carbon atoms, and preparing a flavor-imparting agent containing 5 ppm by mass or more of the lactone having 6 to 14 carbon atoms, wherein 10% by mass or more of the constituent fatty acids of the glyceride are linear saturated fatty acids having 6 to 14 carbon atoms, and the lactone is γ-lactone and / or δ-lactone.

[0013] In the glyceride used as the raw material, 10% by mass or more, for example, 30% by mass or more, 60% by mass or more, 75% by mass or more, 90% by mass or more, or all (100% by mass) of the constituent fatty acids are 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 caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, etc., and preferably caprylic acid and / or capric acid, or lauric acid and / or myristic acid. Caprylic acid and / or capric acid are more preferred, and caprylic acid is most preferred. When 10% by mass or more of the constituent fatty acids are straight-chain saturated fatty acids having 6 to 14 carbon atoms, a desired amount of lactone having 6 to 14 carbon atoms can be produced. Since the amount of lactone produced is very small compared to the amount of fatty acids constituting the glyceride, the amount of glyceride and the proportion (mass ratio) of the constituent fatty acids are hardly affected by the formation of lactones from fatty acids, and therefore the amount of glyceride and the mass ratio of the constituent fatty acids are substantially the same before and after the oxidative heat treatment.

[0014] When the glyceride contains unsaturated fatty acids as constituent fatty acids other than linear saturated fatty acids having 6 to 14 carbon atoms, the amount of unsaturated fatty acids is preferably small, since the unsaturated fatty acids may be oxidized and produce rancid odors that may be imparted to the flavor enhancer. For example, unsaturated fatty acids preferably account for 0 to 5 mass% of the constituent fatty acids of the glyceride, and more preferably 0 to 3 mass%. When unsaturated fatty acids are contained, they are preferably linear unsaturated fatty acids having 16 to 22 carbon atoms that constitute vegetable oils, and more preferably one or more selected from oleic acid, linoleic acid, linolenic acid, and erucic acid.

[0015] The starting glycerides may contain one or more of monoglycerides, diglycerides, and 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 the starting glycerides are triglycerides. These starting glycerides can be obtained by the esterification reaction of fatty acids and glycerin, the transesterification reaction of fatty acid esters and glycerin, or fatty acids and fats and oils, or the transesterification reaction of fatty acid methyl or ethyl esters and glycerin or fats and oils. Furthermore, when unsaturated fatty acids are contained, the fatty acids, fatty acid methyl or ethyl esters, or glycerides may be hydrogenated to reduce the number of unsaturated bonds. Hydrogenated coconut oil or palm kernel oil can also be used. Furthermore, other oils and fats, such as coconut oil, palm kernel oil, palm oil, palm fractionated oils (palm olein, palm superolein, palm midfraction, palm stearin, etc.), shea butter, shea fractionated oil, sal fat, sal fractionated oil, illipe fat, soybean oil, rapeseed oil, cottonseed oil, safflower oil, sunflower oil, rice oil, corn oil, sesame oil, olive oil, perilla oil, linseed oil, peanut oil, milk fat, cocoa butter, and the like, as well as mixtures and processed oils and fats thereof, can be mixed, so long as 10% by mass or more of the constituent fatty acids of the raw material glyceride are straight-chain saturated fatty acids having 6 to 14 carbon atoms.

[0016] The raw glyceride used is preferably one refined for edible use, or a mixture of refined and unrefined glycerides may be used. From the viewpoint of the flavor of the resulting flavor enhancer, the content of unrefined glycerides is preferably 0 to 20% by mass, more preferably 0 to 10% by mass, and even more preferably 0 to 5% by mass, relative to the total mass of the raw glycerides. Examples of purification treatments for edible use include degumming, deacidification, bleaching, and deodorization.

[0017] The temperature in the oxidative heat treatment of the starting glyceride may be any temperature at which a lactone having 6 to 14 carbon atoms is produced, and is 140°C or higher, 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 may be any time sufficient to oxidize the starting glyceride and produce a lactone. For example, when the heating temperature is 180°C or higher, the starting glyceride may be heated for 5 minutes or more, preferably 10 to 120 minutes, 20 to 90 minutes, or 45 to 75 minutes, after the starting glyceride reaches 180°C. Furthermore, when the heating temperature is 160 to 180°C, the starting glyceride may be heated for 10 minutes or more, preferably 15 to 160 minutes, or 30 to 120 minutes, after the starting glyceride reaches 160°C. Furthermore, for example, when the heating temperature is 140 to 160° C., the raw material glyceride may be heated for 15 minutes or more, preferably 90 to 180 minutes, or 90 to 160 minutes, after the raw material glyceride reaches 140° C. The heat treatment conditions are not particularly limited as long as they are conditions that allow the raw material glyceride to be oxidized to produce lactone, and preferably, the raw material glyceride may be heated in the presence of oxygen, for example, in the atmosphere.

[0018] The oxidative heat treatment produces lactones with a carbon number corresponding to the constituent fatty acids in the raw glyceride. In the method of the present invention, lactones with a carbon number of 6 to 14, preferably 8 to 14, more preferably 8 to 10, and even more preferably 8 are produced.

[0019] In the method of the present invention, lactones having 6 to 14 carbon atoms are produced in an amount such that the lactone content 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 300 ppm or more. The lactone content in the flavor-imparting agent may be, for example, 600 ppm or less, 500 ppm or less, 400 ppm or less, or 350 ppm or less. When the lactone content in the flavor-imparting agent is 5 ppm or more, the flavor-imparting agent exhibits a sweet aroma and / or a milky aroma. As long as the amount of lactones having 6 to 14 carbon atoms produced is within this range, lactones having 5 or less or 15 or more carbon atoms may also be produced.

[0020] As the lactone having 6 to 14 carbon atoms, γ-lactone and / or δ-lactone having a stable structure is produced. The mass ratio (γ:δ) of γ-lactone to δ-lactone having 6 to 14 carbon atoms is not particularly limited and may be, for example, 100:0 to 0:100. Furthermore, the mass ratio (γ:δ) of γ-lactone to δ-lactone having 6 to 10 carbon atoms may be, for example, 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, the mass ratio (γ:δ) of γ-lactone and δ-lactone having 11 to 14 carbon atoms may 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.

[0021] The method of the present invention may include a step of preparing a flavor enhancer containing 5 ppm or more of a lactone having 6 to 14 carbon atoms by further mixing an additional glyceride after the oxidative heat treatment of the raw material glyceride. The mixing of the additional glyceride can be performed using any conventionally known mixing means without particular limitation. The additional glyceride may be the same as or different from the raw material glyceride, and may be any glyceride that can be commonly added to foods. The amount of the additional glyceride to be mixed is not particularly limited, as long as the final flavor enhancer contains 5 ppm or more of a lactone having 6 to 14 carbon atoms produced by the oxidative heat treatment.

[0022] The present invention also relates to a method for imparting a flavor to a glyceride, comprising a step of subjecting the glyceride to oxidative heat treatment at 140°C or higher to produce 5 ppm by mass or more of a lactone having 6 to 14 carbon atoms, wherein 10% by mass or more of the constituent fatty acids of the glyceride are linear saturated fatty acids having 6 to 14 carbon atoms, and the lactone is γ-lactone and / or δ-lactone. The starting glyceride, the produced lactone having 6 to 14 carbon atoms, and the conditions for the oxidative heat treatment are the same as those for the above-mentioned method for producing a flavor imparting agent.

[0023] The present invention also relates to a flavor-imparting agent comprising 80% by mass or more of a glyceride and 5 ppm or more of a lactone having 6 to 14 carbon atoms, based on the total mass of the flavor-imparting agent, wherein 0 to 5% by mass of the constituent fatty acids of the glyceride are unsaturated fatty acids, and 10% by 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.

[0024] The glyceride contained in the flavor-imparting agent may be one contained in a product obtained by oxidative heating of the raw glyceride, and may optionally contain the additional glyceride. The glyceride contained in the flavor-imparting agent has 10% by mass or more, for example, 30% by mass or more, 60% by mass or more, 80% by mass or more, 90% by mass or more, or all (100% by mass) of its constituent fatty acids being 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 caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, etc., and preferably caprylic acid and / or capric acid, or lauric acid and / or myristic acid. Caprylic acid and / or capric acid are more preferred, and caprylic acid is most preferred.

[0025] When the glyceride contains unsaturated fatty acids as constituent fatty acids other than linear saturated fatty acids having 6 to 14 carbon atoms, the amount of unsaturated fatty acids is preferably small, since the unsaturated fatty acids may be oxidized and produce rancid odor, which may be added to the flavor enhancer. In the flavor enhancer of the present invention, unsaturated fatty acids preferably account for 0 to 5 mass% of the constituent fatty acids of the glyceride, and more preferably 0 to 3 mass%. When unsaturated fatty acids are contained, they are preferably linear unsaturated fatty acids having 16 to 22 carbon atoms that constitute vegetable oils, and more preferably one or more selected from oleic acid, linoleic acid, linolenic acid, and erucic acid.

[0026] The glyceride contained in the flavoring agent may include glycerides obtainable by esterification of fatty acids and glycerin, transesterification of fatty acid esters and glycerin, or transesterification of fatty acids and fats and oils, or transesterification of methyl or ethyl esters of fatty acids and glycerin or fats and oils. When unsaturated fatty acids are contained, the fatty acids, methyl or ethyl esters of fatty acids, or glycerides may be hydrogenated to reduce the number of unsaturated bonds. Hydrogenated coconut oil or palm kernel oil may also be used. In addition, other oils and fats, such as coconut oil, palm kernel oil, palm oil, palm fractionated oil (palm olein, palm superolein, palm midfraction, palm stearin, etc.), shea butter, shea fractionated oil, sal fat, sal fractionated oil, illipe fat, soybean oil, rapeseed oil, cottonseed oil, safflower oil, sunflower oil, rice oil, corn oil, sesame oil, olive oil, perilla oil, linseed oil, peanut oil, milk fat, cocoa butter, and the like, as well as mixtures and processed oils and fats thereof, can be mixed in the flavor-imparting agent, as long as 10% by mass or more of the constituent fatty acids of the glycerides contained in the flavor-imparting agent are straight-chain saturated fatty acids having 6 to 14 carbon atoms.

[0027] The glycerides contained in the flavoring agent may include one or more of monoglycerides, diglycerides, or triglycerides, and 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 the glycerides contained in the flavoring agent are triglycerides.

[0028] The flavor enhancer of the present invention preferably contains a glyceride that has been subjected to the oxidative heat treatment described in the above-mentioned method for producing a flavor enhancer. The degree of oxidation of the glyceride is indicated by the peroxide value and the anisidine value, and these indicators increase upon oxidation.

[0029] The glyceride contained in the flavoring agent preferably has a peroxide value of 7.5 or more. The glyceride contained in the flavoring agent more preferably has a peroxide value of 10 to 100, 15 to 90, 20 to 80, 25 to 70, or 30 to 60. A peroxide value of 7.5 or more of the glyceride indicates that the glyceride has been oxidized to a certain level or more. The peroxide value can be measured according to "Peroxide Value (Acetic Acid-Isooctane Method)" in Standard Methods for the Analysis of Fats, Oils, and Related Materials (edited by the Japan Oil Chemists' Society), 2.5.2.1-2013.

[0030] Furthermore, the oxidative heat treatment also increases the anisidine value, another indicator of oxidation. The glyceride contained in the flavoring agent may have, for example, an anisidine value of 0.8 or more, preferably an anisidine value of 1.0 or more. More preferably, the glyceride contained in the flavoring agent may have an anisidine value of 0.9 to 10.0, 1.0 to 8.0, 1.5 to 6.0, 2.0 to 5.5, 2.5 to 5.0, or 3.0 to 4.5. An anisidine value of 0.8 or more of the glyceride indicates that oxidation has occurred to a certain level or more. The anisidine value can be measured according to "Anisidine Value" in Standard Methods for the Analysis of Fats, Oils, and Related Materials (edited by the Japan Oil Chemists' Society), 2.5.3-2013.

[0031] In the same oxidative heat treatment, the peroxide value tends to increase in the case of straight-chain saturated fatty acids having 6 to 10 carbon atoms, while the anisidine value tends to increase in the case of straight-chain saturated fatty acids having 11 to 14 carbon atoms. The glyceride contained in the flavor imparting agent preferably has a peroxide value of 7.5 or more and / or an anisidine value of 1.0 or more. In the case of a glyceride having straight-chain saturated fatty acids having 6 to 10 carbon atoms as its constituent fatty acids, it is more preferable that the glyceride has a peroxide value selected from the ranges of 10 to 100, 15 to 90, 20 to 80, 25 to 70, or 30 to 60, and even more preferably has an anisidine value selected from the ranges of 1.0 to 8.0, 1.5 to 6.0, 2.0 to 5.5, 2.5 to 5.0, or 3.0 to 4.5. Furthermore, in the case of a glyceride having a straight-chain saturated fatty acid having 11 to 14 carbon atoms as a constituent fatty acid, it is more preferable that the glyceride has an anisidine value selected from the ranges 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, and 1.0 to 2.0.

[0032] The glyceride content in the flavoring agent is 80% by mass or more, preferably 85% by mass or more, 90% by mass or more, 95% by mass or more, or 99% by mass or more, based on the total mass of the flavoring agent. If the glyceride content is within the above range, the flavoring agent will be sufficiently effective as a base material.

[0033] The lactone having 6 to 14 carbon atoms contained in the flavoring agent is γ-lactone and / or δ-lactone, and may be one contained in a product obtained by oxidative heating of the raw glyceride. The content of the lactone having 6 to 14 carbon atoms in the flavoring 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, based on the total mass of the flavoring agent. The content of the lactone having 6 to 14 carbon atoms in the flavoring agent may be, for example, 600 ppm or less, 500 ppm or less, 400 ppm or less, or 350 ppm or less. When the content of the lactone having 6 to 14 carbon atoms is 5 ppm or more, the flavoring agent exhibits a sweet aroma and / or a milky aroma.

[0034] The mass ratio (γ:δ) of γ-lactone to δ-lactone having 6 to 14 carbon atoms contained in the flavor imparting agent is not particularly limited and may be, for example, 100:0 to 0:100. Furthermore, the mass ratio (γ:δ) of γ-lactone to δ-lactone having 6 to 10 carbon atoms may be, for example, 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, the mass ratio (γ:δ) of γ-lactone to δ-lactone having 11 to 14 carbon atoms may 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.

[0035] The present invention provides a flavor enhancer having a sweet aroma and / or a milky aroma. The term "sweet aroma" refers to an aroma derived from γ-lactone and / or δ-lactone having 6 to 10 carbon atoms. The term "milk aroma" refers to an aroma derived from γ-lactone and / or δ-lactone having 11 to 14 carbon atoms.

[0036] The flavor enhancer may contain any other ingredients that are typically added to foods, provided that the sweet aroma and / or milk aroma is not impaired. Examples of other ingredients include emulsifiers, antioxidants, alcohol, water, pH adjusters, seasonings, colorants, fragrances, antifoaming agents, sugars, sugar alcohols, stabilizers, etc. Examples of emulsifiers include polyglycerol fatty acid esters, polyglycerol condensed ricinoleates, sorbitan fatty acid esters, sorbitol fatty acid esters, sucrose fatty acid esters, propylene glycol fatty acid esters, organic acid monoglycerides, polysorbates, lecithin, etc. Examples of antioxidants include tocopherols, tocotrienols, carotenes, polyphenols, ascorbic acid, ascorbic acid derivatives, etc. [Example]

[0037] (raw glyceride) The following glycerides were used as raw materials: ODO ("Medium-chain triglyceride" manufactured by Nisshin Oillio Group Co., Ltd., constituent fatty acids: caprylic acid 75%, capric acid 25%) ODO+Toc (ODO with 500 ppm of soybean-derived tocopherol added) C10R ("Medium-chain triglyceride" manufactured by Nisshin Oillio Group Co., Ltd., constituent fatty acids: caprylic acid 30%, capric acid 70%) Tricaprylin ("Medium-chain triglyceride" manufactured by Nisshin Oillio Group, Inc., constituent fatty acids: caprylic acid approximately 100%) Tricaprin ("medium-chain triglyceride" manufactured by Nisshin Oillio Group, Inc., constituent fatty acids: capric acid approximately 100%) Trilaurin ("Trilaurin" manufactured by Tokyo Chemical Industry Co., Ltd., constituent fatty acid: lauric acid approximately 98%) Trimyristin ("Trimyristin" manufactured by Tokyo Chemical Industry Co., Ltd., constituent fatty acid: myristic acid approx. 95%)

[0038] (oxidative heat treatment) A 50.00 g sample of ODO was placed in a 200 mL beaker and heated to 180°C in the atmosphere using a PID temperature-controlled mantle heater. A sweet aroma began to emanate when the sample temperature exceeded 140°C. 0, 5, 15, 30, and 60 minutes after the sample temperature reached 180°C, the sample was immediately transferred to a nitrogen-purged brown bottle, capped, and left to stand until the temperature reached 20°C.

[0039] ODO+Toc, C10R, tricaprylin, tricaprin, trilaurin, and trimyristin were treated in the same manner as ODO, except that they were transferred to brown bottles 60 minutes after the sample temperature reached 180°C.

[0040] (analysis) The peroxide value (POV) of each sample of untreated ODO, trilaurin, and trimyristin, and each of the treated samples, was measured according to Standard Methods for the Analysis of Fats, Oils, and Related Materials (edited by the Japan Oil Chemists' Society) 2.5.2.1-2013 "Peroxide Value (Acetic Acid-Isooctane Method)".

[0041] The anisidine value (AnV) of each of the untreated ODO, trilaurin, and trimyristin samples, and the treated samples, was measured in accordance with the "Anisidine Value" in the Standard Methods for the Analysis of Fats, Oils, and Related Materials (edited by the Japan Oil Chemists' Society) 2.5.3-2013.

[0042] The lactone contents of untreated ODO, trilaurin and trimyristin, and each treated sample were measured by GC / MS under the following conditions. GC / MS Conditions Column: DB-1HT (15m x φ0.25mm x 0.1μm) Heating conditions: 40°C [3 min] - 4°C / min - 170°C - 25°C / min - 370°C [7 min] Carrier gas: Helium Inlet: 370°C, split ratio = 20:1 Ion source: EI Detector: MSD ·Solution concentration: 0.1mg / mL ·Injection volume: 1μL Analysis method: Quantitative analysis (ppm) using C8-C14 lactone STD solution as an external standard

[0043] The analytical results of the peroxide value (POV) and anisidine value (AnV) are shown in Table 1, and the analytical results of the lactone content are shown in Table 1 and Figure 1. [Table 1]

[0044] No lactones were detected in untreated ODO, trilaurin and trimyristin, or ODO+Toc to which tocopherol was added as an antioxidant. After oxidative heat treatment, lactones present in each sample were limited to lactones with 8, 10, 12, and / or 14 carbon atoms, which correspond to the carbon numbers of the constituent fatty acids in the raw glycerides. Furthermore, the amount of glyceride and the mass ratio of the constituent fatty acids did not change substantially before and after oxidative heat treatment.

[0045] (Scent rating: 1) The aroma of each sample (20°C) of untreated ODO, oxidatively heat-treated ODO, ODO + Toc, C10R, tricaprylin, and tricaprin was evaluated by 10 panelists according to the following criteria. The aroma of sample 2 was given a score of 2, and a relative evaluation was performed. The results (average scores) are shown in Table 2. 0 points: No sweet scent. 1 point: A faint sweet scent is detected (weaker than sample 2). 2 points: Sweet scent (same as sample 2). 3 points: A slightly strong sweet scent (stronger than sample 2 but less than twice as strong) 4 points: Strong sweet scent (approximately twice as strong as sample 2) 5 points: The sweet scent is quite strong (more than twice that of sample 2)

[0046] [Table 2]

[0047] Lactones with 8 carbon atoms are produced from fatty acids with 8 carbon atoms (caprylic acid), and lactones with 10 carbon atoms are produced from fatty acids with 10 carbon atoms (capric acid). A correlation was observed between the strength of the sweet aroma and the amount of lactones produced.

[0048] (Aroma rating: 2) For each sample (20°C) of untreated trilaurin and trimyristin and oxidatively heat-treated trilaurin and trimyristin, 10 panelists evaluated the presence or absence of a milky aroma according to the following criteria. The results (average scores) are shown in Table 3. 0 points: No milky scent. 1 point: Smells like milk.

[0049] [Table 3]

[0050] The 12-carbon lactone is produced from a 12-carbon fatty acid (lauric acid), and the 14-carbon lactone is produced from a 14-carbon fatty acid (myristic acid). Samples containing 12- or 14-carbon lactones had a milky aroma. [Industrial Applicability]

[0051] The flavor enhancer provided by the present invention can be used to impart flavor to foods.

Claims

1. A method for producing a flavoring agent, comprising: the method includes a step of subjecting a glyceride to oxidative heat treatment at 140°C or higher to generate a lactone having 6 to 14 carbon atoms, and preparing a flavor-imparting agent containing the lactone having 6 to 14 carbon atoms in an amount of 5 ppm by mass or more; (A) 10% by mass or more of the constituent fatty acids of the glyceride to be subjected to the oxidative heat treatment are straight-chain saturated fatty acids having 6 to 14 carbon atoms and 0 to 5% by mass of unsaturated fatty acids, or (B) 30% by mass or more of the constituent fatty acids are straight-chain saturated fatty acids having 6 to 14 carbon atoms, The lactone is a gamma lactone and / or a delta lactone. method.

2. The method described in claim 1, further comprising a step of mixing additional glycerides after the oxidative heat treatment to prepare a flavoring agent containing 5 ppm by mass or more of lactones having 6 to 14 carbon atoms.

3. A method for producing a flavoring agent, comprising: the method includes a step of subjecting a glyceride to oxidative heat treatment at 140°C or higher to generate a lactone having 6 to 14 carbon atoms, and further mixing additional glyceride after the oxidative heat treatment to prepare a flavor imparting agent containing 5 ppm by mass or more of the lactone having 6 to 14 carbon atoms, 10% by mass or more of the constituent fatty acids of the glyceride to be subjected to the oxidative heat treatment are straight-chain saturated fatty acids having 6 to 14 carbon atoms, The lactone is a gamma lactone and / or a delta lactone. method.

4. The method according to any one of claims 1 to 3, wherein 0 to 5 mass% of constituent fatty acids of the glyceride subjected to the oxidative heat treatment are unsaturated fatty acids.

5. The method according to any one of claims 1 to 4, wherein 60% by mass or more of the constituent fatty acids of the glyceride subjected to the oxidative heat treatment are straight-chain saturated fatty acids having 6 to 14 carbon atoms.

6. The method according to any one of claims 1 to 5, wherein the constituent fatty acids of the glyceride subjected to the oxidative heat treatment consist solely of linear saturated fatty acids having 6 to 14 carbon atoms.

7. The method according to any one of claims 1 to 6, wherein the glyceride to be subjected to the oxidative heat treatment is a triglyceride.

8. A flavor-imparting agent comprising 80% by mass or more of a glyceride and 5 ppm or more of a lactone having 6 to 14 carbon atoms, based on the total mass of the flavor-imparting agent, 0 to 5% by mass of the constituent fatty acids of the glyceride are unsaturated fatty acids, 10% by mass or more of the constituent fatty acids of the glyceride are straight-chain saturated fatty acids having 6 to 14 carbon atoms, The lactone is a gamma lactone and / or a delta lactone. Flavoring agent.

9. The flavoring agent according to claim 8, wherein the glyceride has a peroxide value of 7.5 or more and / or an anisidine value of 1.0 or more.

10. The flavor imparting agent according to claim 8 or 9, wherein 60% by mass or more of the constituent fatty acids of the glyceride are straight-chain saturated fatty acids having 6 to 14 carbon atoms.

11. The flavor imparting agent according to any one of claims 8 to 10, wherein the constituent fatty acids of the glyceride consist solely of linear saturated fatty acids having 6 to 14 carbon atoms.

12. The flavor imparting agent according to any one of claims 8 to 11, wherein the glyceride is a triglyceride.

13. The flavor enhancer according to any one of claims 8 to 12, which has a sweet scent and / or a milky scent.

14. 1. A method for imparting flavor to glycerides, comprising: The method includes a step of subjecting a glyceride to oxidative heat treatment at 140°C or higher to produce 5 ppm by mass or more of lactones having 6 to 14 carbon atoms, (A) 10% by mass or more of the constituent fatty acids of the glyceride are straight-chain saturated fatty acids having 6 to 14 carbon atoms and 0 to 5% by mass are unsaturated fatty acids, or (B) 30% by mass or more of the constituent fatty acids are straight-chain saturated fatty acids having 6 to 14 carbon atoms, The lactone is a gamma lactone and / or a delta lactone. method.

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