Flavored fat and oil composition, method for producing the same, agent for imparting refreshing sensation, and method for imparting refreshing sensation

Abstract

To provide a flavored fat and oil composition and the like, capable of imparting a refreshing sensation to food materials.SOLUTION: A flavored fat and oil composition comprises at least one of a conjugated diene compound represented by the following formula and its peroxide.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a flavor oil or fat composition and a method for producing the same, as well as an agent for imparting a refreshing feeling and a method for imparting a refreshing feeling. [Background technology]

[0002] Conventionally, aromatic components have been added to food materials for the purpose of improving the flavor, etc. As aromatic components, alcohols (e.g., menthol), aldehydes (e.g., cinnamaldehyde, citral), lactones (e.g., γ-undecalactone), ketones (e.g., maltol), etc. are preferably used.

[0003] Among such aromatic components, 2,6-nonadienal, an aldehyde, is known to be capable of imparting a refreshing feeling. For example, Patent Document 1 describes an invention relating to a beverage that contains 50 ppb or more of 2,6-nonadienal. Patent Document 1 describes that it is possible to provide a beverage with a fresh and refreshing aroma.

[0004] Here, Patent Document 1 describes that no method for industrially producing 2,6-nonadienal has been developed, and that chemical synthesis methods for other nonadienals (4,7-nonadienal, 4,8-nonadienal, 2,7-octadienal, 2,11-dodecadienal, etc.) require expensive reagents, complicated production processes, and large amounts of organic solvents, making them difficult to apply to food ingredients, etc.

[0005] In response to this, Patent Document 1 describes a method for producing 2,6-nonadienal by using linolenic acid obtained from yeast as a substrate and reacting it with lipoxygenase obtained from a plant (preferably green malt). Patent Document 1 describes that 2,6-nonadienal can be safely and mass-produced by using linolenic acid and lipoxygenase obtained from yeast or a plant, the safety of which has been established. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] JP 2003-93084 A Summary of the Invention [Problem to be solved by the invention]

[0007] However, the method described in Patent Document 1 requires the use of yeast-derived linolenic acid and plant-derived lipoxygenase, and therefore the production costs remain high, making it difficult to apply industrially. For this reason, it has been difficult to impart a refreshing taste to food materials using 2,6-nonadienal.

[0008] Under such circumstances, the present invention provides a flavor oil and fat composition capable of imparting a refreshing feeling to food materials. [Means for solving the problem]

[0009] The present inventors have found that a specific conjugated diene compound obtained by isomerizing α-linolenic acid can impart a refreshing feeling to food materials. That is, the present invention has, for example, the following aspects.

[0010] [1] The formula: [ka] The flavor oil composition comprises at least one of a conjugated diene compound represented by the formula (I) and a peroxide thereof. [2] The flavor oil composition according to [1] above, wherein the total content of the conjugated diene compound and its peroxide is 5% by mass or more and 80% by mass or less, based on the total mass of the flavor oil composition. [3] The flavor oil composition according to [1] or [2] above, having a peroxide value (POV) of less than 10 meq / kg. [4] The flavor oil composition according to [1] or [2] above, having a peroxide value (POV) of 10 meq / kg or more and 130 meq / kg or less. [5] The flavor oil and fat composition according to any one of [1] to [4] above, which is for use in cooking. [6] The flavor oil and fat composition according to any one of [1] to [4] above, which is for use in non-heat cooking. [7] A reaction solution containing an edible oil having an α-linolenic acid content of 0.1 to 80 mass% of the total amount of constituent fatty acids and an alkaline compound is subjected to the process represented by the following formula: [ka] The present invention relates to a method for producing a flavor oil composition, the method comprising the steps of: [8] The method according to [7] above, wherein the alkali isomerization step is carried out at a temperature of 110°C or higher and 230°C or lower. [9] The method according to [7] or [8] above, wherein the alkaline compound is selected from at least one of sodium hydroxide and potassium hydroxide.

[10] The method according to any one of the above [7] to [9], wherein the molar concentration of the alkaline compound in the reaction solution is 0.5 M or more and 5 M or less.

[11] The method according to any one of the above [7] to

[10] , further comprising an oxidation step of oxidizing a composition to be oxidized containing the conjugated diene compound at 80°C or higher and 180°C or lower to obtain a peroxide of the conjugated diene compound.

[12] The method according to

[11] above, wherein the oxidation time in the oxidation step is from 0.5 hours to 10 hours.

[13] The method according to

[11] or

[12] above, wherein the oxidation step is carried out until the peroxide value (POV) of the flavor oil or fat composition is 10 meq / kg or more and 130 meq / kg or less.

[14] The method according to any one of the above

[11] to

[13] , wherein the content of the conjugated diene compound in the composition to be oxidized is 20 mass% or more based on the total mass of the composition to be oxidized.

[15] The method for producing an edible oil or fat according to any one of [7] to

[14] above, wherein the edible oil or fat comprises at least one selected from the group consisting of perilla oil, linseed oil, and shiso oil.

[16] A refreshing feeling imparting agent comprising the flavor oil and fat composition according to any one of [1] to [6] above.

[17] A method for imparting a refreshing feeling, comprising applying to a food material a flavor oil or fat composition described in any one of [1] to [6] above, or a flavor oil or fat composition produced by a method described in any one of [7] to

[15] above.

[18] The method for imparting a refreshing feeling described in

[17] above, wherein the food material is for cooking by heating.

[19] The method for imparting a refreshing feeling described in

[17] above, wherein the food material is for non-heat cooking. Effect of the Invention

[0011] According to the present invention, there is provided a flavor oil and fat composition capable of imparting a refreshing feeling to food materials. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] Hereinafter, an embodiment of the present invention will be described in detail.

[0013] 1. Flavored oil and fat composition The flavor oil composition according to the present invention contains at least one of a conjugated diene compound represented by the following formula and a peroxide thereof. [ka]

[0014] The flavor oil and fat composition according to the present invention can impart a refreshing feeling to food materials.

[0015] The flavor oil composition according to the present invention will be described in detail below.

[0016] <Conjugated diene compound represented by the above formula> The conjugated diene compound represented by the above formula (hereinafter also referred to as "compound A") is obtained by isomerization of the double bond (cis) at C12 position of α-linolenic acid as shown below, and is a compound (c9t11c15) having a double bond (trans) at C11 position together with a double bond (cis) at C9 position and a double bond (cis) at C15 position. Compound A may have a refreshing feeling.

[0017] [ka]

[0018] By cleaving the double bond at C9 position of compound A, (2E,6Z)-2,6-nonadienal can be derived as shown below.

[0019] [ka]

[0020] That is, compound A itself and / or its decomposition products can impart a refreshing feeling to food materials. In this specification, the term "refreshing feeling" means a refreshing feeling, a fresh green feeling, or the like. In a preferred embodiment, compound A itself and / or its decomposition products retain a fresh aroma, which can enhance the sharpness of the aftertaste. In this specification, "sharp aftertaste" means the duration of the aftertaste. Also, "strong sharp aftertaste" means that the duration of the aftertaste is short. The sharpness of the aftertaste can be determined by comparing the degree to which the aftertaste lingers 30 seconds after eating the target product with the initial taste felt immediately after eating the target product, with a reference product. In addition, when fats and oils are used in the presence of oxygen at high temperatures, volatile decomposition products are generated, which can cause off-flavors (perception based on odor components different from those of fats and oils). However, compound A obtained by isomerization of α-linolenic acid has a refreshing taste both in itself and / or as its decomposition product, (2E,6Z)-2,6-nonadienal, and therefore the off-flavors caused by the generation of compound A (isomerization of α-linolenic acid) and its decomposition are unlikely to occur.

[0021] In one embodiment, the content of compound A is, relative to the total mass of the flavor oil and fat composition, more preferably 0.5% by mass or more and 80% by mass or less, 0.5% by mass or more and 50% by mass or less, 1% by mass or more and 50% by mass or less, 2% by mass or more and 40% by mass or less, 2% by mass or more and 30% by mass or less, 5% by mass or more and 50% by mass or less, 5% by mass or more and 40% by mass or less, 5% by mass or more and 30% by mass or less, 10% by mass or more and 50% by mass or less, 10% by mass or more and 40% by mass or less, 10% by mass or more and 30% by mass or less is even more preferable, 20% by mass or more and 50% by mass or less, 20% by mass or more and 40% by mass or less, 20% by mass or more and 30% by mass or less is particularly preferable, and 25% by mass or more and 50% by mass or less, 25% by mass or more and 40% by mass or less, 25% by mass or more and 30% by mass or less is most preferable. In another embodiment, a part of the compound A contained in the flavor oil composition may be changed to a peroxide or a decomposition product by oxidation (or aging), and the content of the compound A in the flavor oil composition is preferably 0.5% by mass or more and 40% by mass or less, more preferably 1% by mass or more and 40% by mass or less, 1% by mass or more and 40% by mass or less, 3% by mass or more and 40% by mass or less, 5% by mass or more and 40% by mass or less, 10% by mass or more and 40% by mass or less, 17.5% by mass or more and 40% by mass or less, 20% by mass or more and 40% by mass or less, 1% by mass or more and 30% by mass or less, 3% by mass or more and 30% by mass or less, 5% by mass or more and 30% by mass or less, 10% by mass or more and 30% by mass or less, 17.5% by mass or more and 30% by mass or less, 20% by mass or more and 40% by mass or less. More than 30% by mass, 1% by mass and more than 20% by mass, 3% by mass and less than 20% by mass, 10% by mass and more than 20% by mass, 17.5% by mass and more than 20% by mass, 1% by mass and more than 20% by mass, 3% by mass and less than 20% by mass, 5% by mass and less than 20% by mass, 10% by mass and more than 20% by mass, 17.5% by mass and less by 20% by mass, It is more preferable that the content is 1 mass% or more and 17.5 mass% or less, 3 mass% or more and 17.5 mass% or less, 5 mass% or more and 17.5 mass% or less, 10 mass% or more and 17.5 mass% or less, 1 mass% or more and 10 mass% or less, 3 mass% or more and 10 mass% or less, 5 mass% or more and 10 mass% or less, 1 mass% or more and 5 mass% or less, 3 mass% or more and 5 mass% or less, and 1 mass% or more and 3 mass% or less.

[0022] <Peroxides of conjugated diene compounds> The peroxide of a conjugated diene compound (hereinafter also referred to as "peroxide of compound A") is a compound A having a hydroperoxide group (-OOH) introduced into at least one of the double bonds. The introduction of the hydroperoxide group makes it easier to decompose, and (2E,6Z)-2,6-nonadienal is more easily derived. The peroxide of compound A can have a refreshing feeling, just like compound A. Compared with compound A and the peroxide of compound A, (2E,6Z)-2,6-nonadienal has a stronger effect of imparting a refreshing feeling. For this reason, it is preferable to include the peroxide of compound A, which is more likely to induce (2E,6Z)-2,6-nonadienal. The peroxide of compound A may be derived from a conjugated diene compound, and may not have a conjugated diene structure in its structure. In a preferred embodiment, the peroxide of compound A itself and / or its decomposition products can impart a fresh scent, thereby enhancing a sharper aftertaste. In a preferred embodiment, the peroxide of compound A produces (2E,6Z)-2,6-nonadienal, which has a refreshing taste, when decomposed, and therefore does not produce an unpleasant flavor upon decomposition.

[0023] The peroxide of compound A is not particularly limited, but examples thereof include compounds represented by the following formulas (1) to (7).

[0024] [ka]

[0025] Among the above, the peroxide of compound A preferably contains a compound represented by formula (1) and / or formula (2), more preferably a compound represented by formula (2), from the viewpoint of favorably generating (2E,6Z)-2,6-nonadienal. The peroxide of compound A may be contained alone or in a mixture of two or more kinds.

[0026] The total content of the above-mentioned conjugated diene compound (compound A) and its peroxide (peroxide of compound A) is preferably 5% by mass or more and 80% by mass or less, more preferably 5% by mass or more and 70% by mass or less, 5% by mass or more and 60% by mass or less, 5% by mass or more and 50% by mass or less, 5% by mass or more and 40% by mass or less, 5% by mass or more and 30% by mass or less, 10% by mass or more and 70% by mass or less, 10% by mass or more and 60% by mass or less, 10% by mass or more and 50% by mass or less. % or less, 10 mass% or more and 40 mass% or less, 10 mass% or more and 30 mass% or less, 15 mass% or more and 70 mass% or less, 15 mass% or more and 60 mass% or less, 15 mass% or more and 50 mass% or less, 15 mass% or more and 40 mass% or less, 15 mass% % or more and 30 mass% or less, 20 mass% or more and 70 mass% or less, 20 mass% or more and 60 mass% or less, 20 mass% or more and 50 mass% or less, 20 mass% or more and 40 mass% or less, and 20 mass% or more and 30 mass% or less.

[0027] <Conjugated triene compounds> The flavor oil composition may further contain a conjugated triene compound. In this specification, the term "conjugated triene compound" refers to a compound having one or more conjugated triene structures in the molecule. In this case, the "conjugated triene compound" may have one or more double bonds in addition to the conjugated triene structure (i.e., it may be a tetraene compound, etc.). However, for example, a compound having a conjugated diene structure is not included in the "conjugated triene compound".

[0028] Specific examples of conjugated triene compounds include those obtained by isomerization of the double bond (cis) at C12 and the double bond (cis) at C15 of α-linolenic acid, and include a compound having a double bond (trans) at C11 and a double bond (cis) at C13 (hereinafter also referred to as "punicic acid" or "compound B").

[0029] [ka]

[0030] The conjugated triene compound may be contained alone or in combination of two or more kinds.

[0031] In one embodiment, the content of the conjugated triene compound is preferably 30% by mass or less, more preferably 20% by mass or less, and even more preferably 0.1% by mass or more and 10% by mass or less, and even more preferably 0.1% by mass or more and 6% by mass or less, relative to the total mass of the flavor oil or fat composition.

[0032] <Peroxides of conjugated triene compounds> The peroxide of the conjugated triene compound is one in which a hydroperoxide group (-OOH) is introduced into at least one of the double bonds of the above-mentioned conjugated triene compound. Note that the peroxide of the conjugated triene compound may be any peroxide derived from a conjugated triene compound, and may not have a conjugated triene structure in its structure.

[0033] For example, examples of peroxides of punicic acid (compound B), which is a conjugated triene compound, include the following compounds (hereinafter also referred to as "peroxides of punicic acid" or "peroxides of compound B").

[0034] [ka]

[0035] The oxide of the conjugated triene compound may be contained alone or in a mixture of two or more kinds.

[0036] <Other conjugated diene compounds> The flavor oil composition may further contain other conjugated diene compounds. In this specification, the term "conjugated diene compound" refers to a compound having one or more conjugated diene structures in the molecule. In this case, the "conjugated diene compound" may have one or more double bonds in addition to the conjugated diene structure (i.e., it may be a triene compound, a tetraene compound, etc.). However, for example, a compound having a conjugated triene structure but not a conjugated diene structure is not included in the "conjugated diene compound". In addition, the term "other conjugated diene compound" refers to a conjugated diene compound other than compound A and the peroxide of compound A.

[0037] Other conjugated diene compounds include, for example, a compound having a double bond (cis) at the C9 position and a double bond (trans) at the C11 position (hereinafter also referred to as "compound C"), a compound having a double bond (trans) at the C10 position and a double bond (cis) at the C12 position (hereinafter also referred to as "compound D"), a compound having a double bond (trans) at the C9 position and a double bond (trans) at the C11 position (hereinafter also referred to as "compound E"), and the like. [ka]

[0038] The above-mentioned other conjugated diene compounds may be contained alone or in a mixture of two or more kinds.

[0039] In one embodiment, the content of the other conjugated diene compounds is preferably 40% by mass or less, more preferably 30% by mass or less, and even more preferably 0.1% by mass or more and 30% by mass or less, based on the total mass of the flavor oil or fat composition.

[0040] <Peroxides of other conjugated diene compounds> The peroxide of the other conjugated diene compound is one in which a hydroperoxide group (-OOH) is introduced into at least one of the double bonds of the above-mentioned other conjugated diene compound. Note that the peroxide of the other conjugated diene compound may be one derived from another conjugated diene compound, and may not have a conjugated diene structure in its structure.

[0041] Examples of the peroxides of other conjugated diene compounds include the peroxide of compound C, the peroxide of compound D, the peroxide of compound E, and the like.

[0042] The peroxides of other conjugated diene compounds may be contained alone or in a mixture of two or more kinds.

[0043] In one embodiment, the total content of compound A and its peroxides, conjugated triene compounds and their peroxides, and other conjugated diene compounds and their peroxides is preferably 10% by mass or more and 80% by mass or less, 10% by mass or more and 70% by mass or less, or 10% by mass or more and 60% by mass or less, more preferably 20% by mass or more and 80% by mass or less, 20% by mass or more and 70% by mass or less, or 20% by mass or more and 60% by mass or less, even more preferably 35% by mass or more and 80% by mass or less, 35% by mass or more and 70% by mass or less, or 35% by mass or more and 60% by mass or less, particularly preferably 43% by mass or more and 80% by mass or less, 43% by mass or more and 70% by mass or less, or 43% by mass or more and 60% by mass or less, and most preferably 50% by mass or more and 80% by mass or less, 50% by mass or more and 70% by mass or less, or 50% by mass or more and 60% by mass or less.

[0044] <Other fatty acids> The flavor oil composition may further comprise other fatty acids.

[0045] The other fatty acids are fatty acids other than the conjugated diene compounds and the conjugated triene compounds, and examples thereof include unsaturated fatty acids and derivatives thereof, and saturated fatty acids and derivatives thereof.

[0046] The unsaturated fatty acid is not particularly limited as long as it is a compound other than a conjugated diene compound and a conjugated triene compound, and examples thereof include α-linolenic acid, linoleic acid, oleic acid, eicosenoic acid, mead acid, erucic acid, and nervonic acid.

[0047] The derivative of the unsaturated fatty acid is not particularly limited as long as it is a fatty acid other than a conjugated diene compound and a conjugated triene compound, and examples of the derivative include a compound in which the double bond of the unsaturated fatty acid is isomerized, a compound in which a hydroperoxide group is introduced into the unsaturated fatty acid, and the like.

[0048] The saturated fatty acid is not particularly limited, but examples thereof include capric acid, myristic acid, palmitic acid, stearic acid, and behenic acid.

[0049] The derivative of the saturated fatty acid is not particularly limited, but examples thereof include a compound in which the double bond of the saturated fatty acid is isomerized, and a compound in which a hydroperoxide group is introduced into the saturated fatty acid.

[0050] The above-mentioned other fatty acids may be contained alone or in a mixture of two or more kinds.

[0051] The content of other fatty acids is preferably 70% by mass or less, more preferably 60% by mass or less, and even more preferably 40% by mass or more and 50% by mass or less, based on the total mass of the flavor oil and fat composition.

[0052] In one embodiment, the content of the unsaturated fatty acid is preferably 30% by mass or more, 40% by mass or more, 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, or 90% by mass or more, relative to the total mass of the other fatty acids.

[0053] In one embodiment, the content of saturated fatty acids is preferably 90% by mass or less, 80% by mass or less, 70% by mass or less, 60% by mass or less, 50% by mass or less, 40% by mass or less, or 30% by mass or less, relative to the total mass of other fatty acids.

[0054] In one embodiment, the total content of compound A and its peroxides, conjugated triene compounds and their peroxides, other conjugated diene compounds and their peroxides, and other fatty acids is, relative to the total mass of the flavor oil and fat composition, preferably 10% by mass or more and 80% by mass or less, 10% by mass or more and 70% by mass or less, or 10% by mass or more and 60% by mass or less, more preferably 20% by mass or more and 80% by mass or less, 20% by mass or more and 70% by mass or less, or 20% by mass or more and 60% by mass or less, even more preferably 35% by mass or more and 80% by mass or less, 35% by mass or more and 70% by mass or less, or 35% by mass or more and 60% by mass or less, particularly preferably 45% by mass or more and 80% by mass or less, 45% by mass or more and 70% by mass or less, or 45% by mass or more and 60% by mass or less, and most preferably 50% by mass or more and 80% by mass or less, 50% by mass or more and 70% by mass or less, or 50% by mass or more and 60% by mass or less.

[0055] <Additives> The flavor oil composition may further comprise an additive.

[0056] The additives are not particularly limited, but include edible oils and fats, antioxidants, colorants, preservatives, and the like.

[0057] For example, when the flavored oil and fat composition is used for deep-fried foods, edible oils and fats generally used for frying can be added as additives.

[0058] <Properties of flavor oil composition> In one embodiment, the peroxide value (POV) of the flavor oil or fat composition is preferably less than 20 meq / kg, more preferably less than 15 meq / kg, even more preferably less than 10 meq / kg, and particularly preferably less than 8 meq / kg, less than 6 meq / kg, 1 meq / kg or more but less than 8 meq / kg, or 1 meq / kg or more but less than 6 meq / kg. In another embodiment, a part of components such as a conjugated diene compound or other conjugated diene compounds contained in the flavor oil and fat composition may be converted to a peroxide by oxidation (or aging), and the peroxide value (POV) of the flavor oil and fat composition is preferably 1 meq / kg or more and 200 meq / kg or less, 1 meq / kg or more and 150 meq / kg or less, or 1 meq / kg or more and 130 meq / kg or less, more preferably 3 meq / kg or more and 150 meq / kg or less, 3 meq / kg or more and 100 meq / kg or less, 5 meq / kg or more and 150 meq / kg or less, 5 meq / kg or more and 130 meq / kg or less, or more preferably 5 meq / kg or more and 100 meq / kg or less. It is even more preferable that the amount is 10 meq / kg or more and 100 meq / kg or less, 10 meq / kg or more and 75 meq / kg or more and 10 meq / kg or more and 60 meq / kg or less, 10 meq / kg or more and 50 meq / kg or more, 15 meq / kg or more and 100 meq / kg or more, 15 meq / kg or more and 75 meq / kg or more and 15 meq / kg or more and 60 meq / kg or less, 15 meq / kg or more and 50 meq / kg or more, 20 meq / kg or more and 130 meq / kg or more and 20 meq / kg or more and 100 meq / kg or more, 20 meq / kg or more and 75 meq / kg or more and 20 meq / kg or more and 60 meq / kg or less, or 20 meq / kg or more and 50 meq / kg or more. A peroxide value (POV) of 1 meq / kg or more is preferable because (2E,6Z)-2,6-nonadienal is easily produced from the flavor oil composition, which can enhance the refreshing feeling, whereas a peroxide value (POV) of 200 meq / kg or less is preferable because the storage stability of the flavor oil composition is increased. The peroxide value (POV) can be adjusted by appropriately changing the conditions of the alkali isomerization step and the conditions of the oxidation step, which will be described later. In this specification, the "peroxide value (POV)" is measured by the method described in the Examples.

[0059] In one embodiment, the flavor oil and fat composition is preferably for cooking. By using the flavor oil and fat composition for cooking, compound A and / or its peroxide are easily decomposed, and (2E,6Z)-2,6-nonadienal is easily derived, which is preferable. In particular, when the cooking method is frying, stir-frying, etc., a refreshing flavor can be achieved while suppressing stickiness, oiliness, etc.

[0060] In one embodiment, the flavor oil composition is preferably for use in non-heat cooking. By applying the flavor oil composition to food materials for non-heat cooking, the flavor of the food materials can be appropriately adjusted to suit preferences.

[0061] 2. Method for producing flavor oil composition According to one embodiment of the present invention, there is provided a method for producing a flavor oil and fat composition, which includes an alkali isomerization step of obtaining a conjugated diene compound (compound A) represented by the following formula from a reaction solution containing an edible oil and fat having an α-linolenic acid content of 0.1 to 80 mass% of the total amount of constituent fatty acids and an alkali compound. [ka]

[0062] Compound A can be produced from α-linolenic acid by an alkali isomerization process.

[0063] The method for producing a flavor oil composition may further include a lipase treatment step, an oxidation step, etc. In one embodiment, the method for producing a flavor oil composition includes a lipase treatment step, an alkali isomerization step, and an oxidation step in this order. In another embodiment, the method for producing a flavor oil composition includes an alkali isomerization step, and an oxidation step in this order.

[0064] <Lipase treatment step> The lipase treatment step is a step in which edible fats and oils having an α-linolenic acid content of 0.1 to 80% by mass of the total amount of constituent fatty acids are reacted with lipase. The α-linolenic acid in the edible fats and oils can be contained in a free form and in the form of constituent fatty acids of triacylglycerol. Therefore, by treating the edible fats and oils with lipase, the proportion of α-linolenic acid liberated by decomposition of triacylglycerol can be increased.

[0065] [Edible fats and oils with an α-linolenic acid content of 0.1 to 80% by mass of the total fatty acids] Examples of edible oils and fats having an α-linolenic acid content of 0.1 to 80% by mass of the total amount of constituent fatty acids include, but are not limited to, perilla oil, linseed oil, shiso oil, chia seed oil, rapeseed oil, corn oil, soybean oil, palm olein, sesame oil, peanut oil, safflower oil, sunflower oil, cottonseed oil, sesame oil, grape seed oil, macadamia nut oil, hazelnut oil, walnut oil, pumpkin seed oil, camellia oil, tea seed oil, olive oil, rice bran oil, wheat germ oil, palm oil, palm kernel oil, coconut oil, cacao butter, beef tallow, lard, chicken oil, and milk fat, as well as interesterified oils, hydrogenated oils, and fractionated oils of these edible oils and fats.

[0066] Among these, from the viewpoint that the content of α-linolenic acid in the total amount of constituent fatty acids is 50 to 80 mass %, the edible oils and fats preferably contain at least one selected from the group consisting of perilla oil, linseed oil, perilla oil, and chia seed oil, more preferably at least one selected from the group consisting of perilla oil, linseed oil, and perilla oil, further preferably at least one of perilla oil and linseed oil, and particularly preferably linseed oil. The above-mentioned edible oils and fats may be used alone or in combination of two or more.

[0067] [Lipase] The lipase is not particularly limited as long as it can cleave the ester bond of triacylglycerol.

[0068] As the lipase, commercially available products may be used, such as Lipase AY "Amano" 30SD, Lipase GS "Amano" 250G, Lipase DF "Amano" 15, Lipase MER "Amano", Lipase MHA "Amano" 10SD, Lipase A "Amano" 6, Lipase R "Amano", Neurase F3G (manufactured by Amano Enzyme Inc.), Lipase OF (manufactured by Meito Sangyo Co., Ltd.), and the like.

[0069] The lipases may be used alone or in combination of two or more kinds.

[0070] [reaction] The reaction between the edible fat or oil and the lipase is not particularly limited, but is preferably carried out by mixing the edible fat or oil, the lipase, and a solvent.

[0071] In this case, the solvent may be water or an organic solvent.

[0072] Examples of the organic solvent include alcohol solvents such as methanol, ethanol, propanol, isopropyl alcohol, butanol, ethylene glycol, propylene glycol, and diethylene glycol; hydrocarbon solvents such as hexane and cyclohexane; ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, diethylene glycol dimethyl ether, and triethylene glycol dimethyl ether; and ketone solvents such as acetone, methyl ethyl ketone, and cyclohexanone.

[0073] Of these, the solvent preferably contains water. The above solvents may be used alone or in combination of two or more kinds.

[0074] The reaction temperature is not particularly limited, but is preferably the optimum temperature for the lipase, preferably 25°C or higher and 45°C or lower, and more preferably 30°C or higher and 40°C or lower.

[0075] <Alkaline isomerization process> The alkali isomerization step is a step for obtaining a conjugated diene compound (compound A) represented by the following formula from a reaction solution containing an edible fat or oil having an α-linolenic acid content of 0.1 to 80 mass% of the total amount of constituent fatty acids and an alkali compound, thereby obtaining a flavor fat or oil composition (composition to be oxidized).

[0076] [ka]

[0077] In the alkali isomerization step, reactions (side reactions) other than the reaction of producing compound A from α-linolenic acid may occur. For example, compound A may be further converted to produce a peroxide of compound A. In addition, conjugated triene compounds (compound B, etc.) and peroxides thereof may be produced from α-linolenic acid. Furthermore, other conjugated diene compounds (compounds C to E, etc.) and peroxides thereof may be produced from fatty acids and the like contained in edible oils and fats (for example, linolenic acid). For this reason, the flavor oil and fat composition (composition to be oxidized) obtained in the alkali isomerization step may contain, in addition to compound A, unreacted components of the edible oil and fat raw material (α-linolenic acid, linoleic acid, etc.), products produced by side reactions (peroxides of compound A, conjugated triene compounds and peroxides thereof, other conjugated diene compounds and peroxides thereof, etc.).

[0078] [Reaction solution] The reaction liquid contains an edible fat or oil in which the content of α-linolenic acid in the total amount of constituent fatty acids is 0.1 to 80 mass % and an alkaline compound. The reaction liquid may further contain a solvent and the like.

[0079] (Edible fats and oils with an α-linolenic acid content of 0.1 to 80% by mass of the total amount of constituent fatty acids) The edible fats and oils having an α-linolenic acid content of 0.1 to 80% by mass of the total amount of constituent fatty acids are as described above. The edible fats and oils also include edible fats and oils (lipase-treated products) obtained by a lipase treatment step.

[0080] In one embodiment, the edible oil preferably includes at least one selected from the group consisting of perilla oil, linseed oil, shiso oil, and chia seed oil, more preferably includes at least one selected from the group consisting of perilla oil, linseed oil, and shiso oil, even more preferably includes at least one of perilla oil and linseed oil, and particularly preferably includes linseed oil. In another embodiment, the edible oils and fats preferably include at least one selected from the group consisting of perilla oil, linseed oil, shiso oil, and chia seed oil, and lipase-treated products thereof, more preferably at least one selected from the group consisting of perilla oil, linseed oil, and shiso oil, and lipase-treated products thereof, even more preferably at least one of perilla oil and linseed oil, and lipase-treated products thereof, and particularly preferably linseed oil and its lipase-treated products. The above-mentioned edible oils and fats may be used alone or in combination of two or more. The above-mentioned edible oils and fats may be used alone or in combination of two or more kinds.

[0081] The content of the edible oil or fat is preferably 5 to 50 mass %, more preferably 10 to 40 mass %, and further preferably 20 to 40 mass %, based on the total mass of the reaction liquid.

[0082] (Alkaline compounds) The alkali compound functions as a catalyst for the alkali isomerization reaction.

[0083] The alkaline compound is not particularly limited, but examples thereof include strong alkaline compounds such as lithium hydroxide, sodium hydroxide, potassium hydroxide, cesium hydroxide, and calcium hydroxide; and weak alkaline compounds such as ammonia, copper hydroxide (II), magnesium hydroxide, zinc hydroxide, iron hydroxide (II), and aluminum hydroxide.

[0084] Among these, the alkaline compound preferably contains a strong alkaline compound, more preferably selected from at least one of sodium hydroxide and potassium hydroxide, and further preferably contains potassium hydroxide. The above-mentioned alkaline compounds may be used alone or in combination of two or more kinds.

[0085] The content of the alkaline compound is preferably from 1% by mass to 40% by mass, more preferably from 5% by mass to 30% by mass, and even more preferably from 10% by mass to 20% by mass, relative to the total mass of the reaction liquid.

[0086] The molar concentration of the alkaline compound in the reaction solution is preferably 0.5 M or more and 5 M or less, more preferably 1 M or more and 5 M or less, and from the viewpoint of obtaining compound A in a higher yield, is further preferably 2 M or more and 5 M or less, particularly preferably 3 M or more and 5 M or less, and most preferably 3 M or more and 4 M or less.

[0087] (solvent) The reaction solution may contain a solvent, and the solvents exemplified in the lipase treatment step can be used as the solvent.

[0088] The solvent used in the reaction solution preferably contains at least one selected from the group consisting of water, an alcohol solvent, an ether solvent, and a ketone solvent, more preferably contains at least one of water and an alcohol solvent, and further preferably contains an alcohol solvent. The above-mentioned solvents may be used alone or in combination of two or more.

[0089] The content of the solvent is preferably from 20% by mass to 80% by mass, more preferably from 20% by mass to 70% by mass, even more preferably from 30% by mass to 60% by mass, and particularly preferably from 40% by mass to 60% by mass, relative to the total mass of the reaction liquid.

[0090] [reaction] By the alkali isomerization reaction, at least a portion of the α-linolenic acid contained in the edible oil or fat is isomerized, and compound A can be obtained.

[0091] The reaction temperature of the alkali isomerization is preferably 90°C or higher and 230°C or lower, more preferably 110°C or higher and 200°C or lower, even more preferably 130°C or higher and 200°C or lower, even more preferably 130°C or higher and 180°C or lower, particularly preferably 130°C or higher and 160°C or lower, and most preferably 145°C or higher and 160°C or lower. In the alkali isomerization reaction step, the heating method is not particularly limited, and examples thereof include heating using a burner and heating by microwaves.

[0092] The reaction time for the alkali isomerization is not particularly limited, but is preferably from 10 to 120 minutes, more preferably from 10 to 90 minutes, from 10 to 80 minutes, from 10 to 70 minutes, from 20 to 90 minutes, from 20 to 80 minutes, or from 20 to 70 minutes, and even more preferably from 40 to 90 minutes, from 40 to 80 minutes, or from 40 to 70 minutes.

[0093] The alkali isomerization reaction can be controlled by appropriately changing the type and amount of the alkaline compound used, the reaction temperature, the reaction time, and the like.

[0094] [Flavored oil composition (oxidized composition)] The alkali isomerization step can produce a flavor oil and fat composition (composition to be oxidized) containing compound A represented by the following formula. When the product obtained in the alkali isomerization step is used as it is for foodstuffs, etc., the product is called a "flavor oil and fat composition," and when the oxidation step is carried out using the product, the product is the raw material for the oxidation step and may be called a "composition to be oxidized."

[0095] [ka]

[0096] In this case, the flavor oil composition (the composition to be oxidized) may contain, due to side reactions or the like, a peroxide of compound A, a conjugated triene compound (compound B) and its peroxide, other conjugated diene compounds (compounds C to E) and their peroxides, etc. Furthermore, the flavor oil and fat composition (the composition to be oxidized) may contain unreacted α-linolenic acid, other fatty acids including linoleic acid, and the like.

[0097] The composition of the flavor oil and fat composition (composition to be oxidized) obtained in the alkali isomerization step is as described above.

[0098] In one embodiment, the content of compound A in the flavor oil and fat composition (composition to be oxidized) obtained in the alkali isomerization step is, relative to the total mass of the flavor oil and fat composition (composition to be oxidized), more preferably 0.5% by mass or more and 80% by mass or less, 0.5% by mass or more and 50% by mass or less, 1% by mass or more and 50% by mass or less, 2% by mass or more and 40% by mass or less, 2% by mass or more and 30% by mass or less, 5% by mass or more and 50% by mass or less, 5% by mass or more and 40% by mass or less, 5% by mass or more and 30% by mass or less, 10% by mass or more and 50% by mass or less, 10% by mass or more and 40% by mass or less, 10% by mass or more and 30% by mass or less is even more preferable, 20% by mass or more and 50% by mass or less, 20% by mass or more and 40% by mass or less, 20% by mass or more and 30% by mass or less is particularly preferable, and 25% by mass or more and 50% by mass or less, 25% by mass or more and 40% by mass or less, 25% by mass or more and 30% by mass or less is most preferable. In another embodiment, the content of compound A in the flavor oil or fat composition (composition to be oxidized) obtained in the alkali isomerization step is, relative to the total mass of the flavor oil or fat composition (composition to be oxidized), preferably 1 mass% or more, more preferably 2 mass% or more, 5 mass% or more, even more preferably 10 mass% or more, 15 mass% or more, particularly preferably 20 mass% or more, and most preferably 20 mass% or more and 50 mass% or less, 20 mass% or more and 40 mass% or less, or 20 mass% or more and 30 mass% or less.

[0099] In one embodiment, the content of conjugated triene compounds in the flavor oil and fat composition (composition to be oxidized) obtained in the alkali isomerization step is preferably 30 mass% or less, more preferably 20 mass% or less, and even more preferably 0.1 mass% or more and 10 mass% or less, and even more preferably 0.1 mass% or more and 6 mass% or less, relative to the total mass of the flavor oil and fat composition (composition to be oxidized).

[0100] In one embodiment, the content of other conjugated diene compounds in the flavor oil and fat composition (composition to be oxidized) obtained in the alkali isomerization step is preferably 40 mass% or less, more preferably 30 mass% or less, and even more preferably 0.1 mass% or more and 30 mass% or less, based on the total mass of the flavor oil and fat composition (composition to be oxidized).

[0101] In one embodiment, the peroxide value (POV) of the flavor oil and fat composition (composition to be oxidized) obtained in the alkali isomerization step is preferably less than 20 meq / kg, more preferably less than 15 meq / kg, even more preferably less than 10 meq / kg, and particularly preferably less than 8 meq / kg, less than 6 meq / kg, 1 meq / kg or more and less than 8 meq / kg, or 1 meq / kg or more and less than 6 meq / kg. The peroxide contained in the flavor oil and fat composition (composition to be oxidized) obtained in the alkali isomerization step can be generated by natural oxidation, a side reaction of the alkali isomerization reaction, or the like.

[0102] <Oxidation process> The oxidation step is a step in which the composition to be oxidized obtained in the alkali isomerization step is oxidized at 80° C. or higher and 180° C. or lower to obtain a peroxide of the conjugated diene compound (peroxide of compound A). This makes it possible to increase the content of the peroxide of compound A, which is likely to induce (2E,6Z)-2,6-nonadienal.

[0103] [Oxidizable composition] The composition to be oxidized is the composition to be oxidized obtained in the alkaline isomerization step.

[0104] In addition, additives and the like can be added to the composition to be oxidized. For example, the degree of oxidation of compound A can be adjusted by adding edible oils and fats to the composition to be oxidized. In this case, the edible oils and fats used are as described above, but it is preferable to use edible oils and fats that are generally used in cooking, and it is more preferable to use corn oil, soybean oil, sesame oil, safflower oil, sunflower oil, cottonseed oil, and even more preferable to use sunflower oil.

[0105] [Oxidation] The oxidation is carried out by heating the composition to be oxidized at a temperature of 80°C or more and 180°C or less.

[0106] The heating temperature for the oxidation is preferably 80°C or higher and 150°C or lower, 80°C or higher and 130°C or lower, or 80°C or higher and 120°C or lower, and more preferably 90°C or higher and 150°C or lower, 90°C or higher and 130°C or lower, or 90°C or higher and 120°C or lower.

[0107] The oxidation time is preferably from 0.1 to 10 hours, more preferably from 0.3 to 10 hours, from 0.5 to 10 hours, from 0.3 to 6 hours, from 0.5 to 6 hours, from 0.3 to 3 hours, and more preferably from 0.5 to 3 hours.

[0108] The oxidation step is preferably performed under suitable conditions depending on the desired effect of the flavor oil composition. In one embodiment, the oxidation step is preferably performed until the peroxide value (POV) of the flavor oil composition is 10 meq / kg or more and 130 meq / kg or less, more preferably until the peroxide value (POV) is 10 meq / kg or more and 100 meq / kg or less, 10 meq / kg or more and 75 meq / kg or less, 10 meq / kg or more and 60 meq / kg or less, 10 meq / kg or more and 50 meq / kg or less, 20 meq / kg or more and 130 meq / kg or less, 20 meq / kg or more and 100 meq / kg or less, 20 meq / kg or more and 75 meq / kg or less, 20 meq / kg or more and 60 meq / kg or less, or 20 meq / kg or more and 50 meq / kg or less.

[0109] [Flavored oil and fat composition] The oxidation step can produce a flavor oil composition containing a peroxide of compound A. In this case, when the raw material composition to be oxidized contains a conjugated triene compound, other conjugated diene compounds, etc., the oxidation step can also produce peroxides of the conjugated triene compound and other conjugated diene compounds.

[0110] In one embodiment, the flavor oil or fat composition obtained in the oxidation step may contain, in addition to the peroxide of compound A, unreacted compound A, a conjugated triene compound, a peroxide of a conjugated triene compound, other conjugated diene compounds, peroxides of other conjugated diene compounds, unreacted α-linolenic acid, other fatty acids including linoleic acid, and the like. The composition of the flavor oil and fat composition (the composition to be oxidized) obtained in the oxidation step is as described above.

[0111] In one embodiment, the content of compound A in the flavor oil and fat composition obtained in the oxidation step is preferably 0.5% by mass or more and 40% by mass or less, more preferably 1% by mass or more and 40% by mass or less, 1% by mass or more and 40% by mass or less, 3% by mass or more and 40% by mass or less, 5% by mass or more and 40% by mass or less, 10% by mass or more and 40% by mass or less, 17.5% by mass or more and 40% by mass or less, 20% by mass or more and 40% by mass or less, 1% by mass or more and 30% by mass or less, 3% by mass or more and 30% by mass or less, 5% by mass or more and 30% by mass or less, 10% by mass or more and 30% by mass or less, 17.5% by mass or more and 30% by mass or less, 20% by mass or more and 30% by mass or less, 1% by mass or more and 20% by mass or less, 3% by mass or more and 30% by mass or less, % to 20 mass%, 5 mass% to 20 mass%, 10 mass% to 20 mass%, 17.5 mass% to 20 mass%, 1 mass% to 20 mass%, 3 mass% to 20 mass%, 5 mass% to 20 mass%, 10 mass% to 20 mass%, 17.5 mass% to 20 mass%, 1 mass% to 17.5 mass% The following are more preferable: 3 mass% to 17.5 mass%, 5 mass% to 17.5 mass%, 1 mass% to 17.5 mass%, 1 mass% to 10 mass%, 3 mass% to 10 mass%, 5 mass% to 10 mass%, 1 mass% to 5 mass%, 3 mass% to 5 mass%, 1 mass% to 3 mass%.

[0112] In one embodiment, the peroxide value (POV) of the flavor oil or fat composition obtained in the oxidation step is preferably 10 meq / kg or more and 130 meq / kg or less, more preferably 10 meq / kg or more and 100 meq / kg or less, 10 meq / kg or more and 75 meq / kg or less, 10 meq / kg or more and 60 meq / kg or less, 10 meq / kg or more and 50 meq / kg or less, 20 meq / kg or more and 130 meq / kg or less, 20 meq / kg or more and 100 meq / kg or less, 20 meq / kg or more and 75 meq / kg or less, 20 meq / kg or more and 60 meq / kg or less, or 20 meq / kg or more and 50 meq / kg or less.

[0113] 3. Refreshing agent According to one aspect of the present invention, there is provided a refreshing sensation imparting agent. The refreshing sensation imparting agent includes the flavor oil and fat composition described above.

[0114] By adding the refreshing sensation imparting agent according to the present invention to foodstuffs, a refreshing sensation can be imparted to the foodstuffs.

[0115] [ingredients] The food material is not particularly limited, and may be either a food material for cooking with heat or a food material for cooking without heat.

[0116] Examples of ingredients for cooking include fried foods, stir-fried foods, and baked foods.

[0117] Examples of fried foods include french fries, fried chicken, croquettes, minced meat cutlets, pork cutlets, fried shrimp, fried oysters, fried horse mackerel, donuts, fried bread, deep-fried chicken, tatsuta-age, tempura, kakiage, fried tofu, thick tofu, fritters, and fried sweets. Examples of stir-fried dishes include stir-fried meat and vegetables, stir-fried vegetables, yakisoba noodles, fried rice, mapo tofu, mapo eggplant, twice-cooked pork, chive and egg, liver and chive, sweet and sour pork, shrimp in chili, sauteed, and meunière. Examples of bakery foods include pound cake, butter cake, bread, sweet bread, pastries, pizza, pies, waffles, choux pastries, biscuits, cookies, taiyaki, dorayaki, and imagawayaki.

[0118] Examples of non-heated cooking ingredients include soy milk, milk, soft drinks, beer, wine, sake, shochu, whiskey, yogurt, ice cream, salads, cheese, pickles, pickles, sashimi, and fruit.

[0119] In one embodiment, the food material is preferably a food material for cooking by heating, more preferably a food material for deep-frying, more preferably a food material for stir-frying, and even more preferably a food material for deep-frying. The refreshing taste imparting agent according to the present invention can achieve a refreshing flavor while suppressing stickiness, oiliness, and the like.

[0120] In one embodiment, the food material is preferably a food material to be cooked without heating. According to the refreshing sensation imparting agent of the present invention, the flavor of the food material can be appropriately adjusted according to preference.

[0121] [Method of adding refreshing agent to ingredients] The method of applying the refreshing feeling imparting agent according to the present invention to food materials is not particularly limited, and can be appropriately selected depending on the cooking method, the properties of the food materials, etc.

[0122] For example, in the case of deep-fried foods, examples of the method include a method of using a refreshing sensation imparting agent as frying oil, a method of adding a refreshing sensation imparting agent to frying oil, a method of kneading a refreshing sensation imparting agent into ingredients before frying, a method of adding a refreshing sensation imparting agent to ingredients after frying, etc. Among these, when ingredients are deep-fried foods, the method of using a refreshing sensation imparting agent as frying oil and the method of adding a refreshing sensation imparting agent to frying oil are preferable.

[0123] In addition, when the food material is to be stir-fried, examples of the method include a method of using a refreshing sensation imparting agent as stir-frying oil, a method of adding a refreshing sensation imparting agent to stir-frying oil, a method of kneading a refreshing sensation imparting agent into the food material before stir-frying, a method of adding a refreshing sensation imparting agent to the food material after stir-frying, etc. Among these, when the food material is to be stir-fried, the method of using a refreshing sensation imparting agent as stir-frying oil and the method of adding a refreshing sensation imparting agent to stir-frying oil are preferable.

[0124] When the food material is a food material for non-heat cooking, the method preferably involves adding a refreshing sensation imparting agent to the food material for non-heat cooking.

[0125] 4. How to give a refreshing feeling According to one embodiment of the present invention, there is provided a method for imparting a refreshing feeling. The method for imparting a refreshing feeling includes imparting the above-mentioned flavor oil and fat composition to a food material. The food material and the flavor oil and fat composition are as described above. EXAMPLES

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

[0127] [Example 1] A flavored oil and fat composition was produced by carrying out a lipase treatment step and an alkali isomerization step.

[0128] (Lipase treatment step) 240 g of linseed oil (α-linolenic acid content in the total amount of constituent fatty acids: 52.1% by mass, linoleic acid content: 16.8% by mass) and 1.2 g of lipase A (Lipase AY "Amano" 30SD, manufactured by Amano Enzyme Inc.) were dissolved in 60 g of water. The resulting solution was stirred at 30°C and 150 rpm. After 6 hours, 1.2 g of the lipase and 60 g of water were further added to the reaction solution. After 24 to 30 hours, the resulting reaction solution was heated at 80°C for 30 minutes to inactivate the lipase. Water was removed by standing separation, and the oil (lipase-treated product) was collected.

[0129] (Alkaline isomerization process) 75 g of propylene glycol as a solvent and 40 g of 62.5% potassium hydroxide (KOH) solution as an alkaline compound were mixed, and nitrogen bubbling was carried out for 20 minutes while stirring at 300 rpm (molar concentration of potassium hydroxide in the reaction solution: 3.5 M). 50 g of the lipase-treated product obtained in the lipase treatment step was added to the resulting mixture, and the reaction was carried out at 100° C. for 60 minutes.

[0130] After the reaction, 20 parts by mass of distilled water was added to 1 part by mass of the reaction solution (pH: 14.0) to dissolve the reactants, and then sulfuric acid was added to adjust the pH to 3.0 (molar concentration: 5 M). Ethanol (1 part by mass) was added to the reaction liquid (1 part by mass), and the mixture was stirred at room temperature (23° C.) at 400 rpm for 1 hour to dissolve the aggregates and recover the oil. The collected oil was washed three times. Specifically, 15 parts by mass of distilled water and 100 mL of ethanol were added to 1 part by mass of oil, and the mixture was stirred at 400 rpm at room temperature (23°C) for 1 hour to collect the oil. This was repeated three times. As a result, a flavored oil and fat composition, which is an alkali isomerized product, was produced.

[0131] [Examples 2 to 10] The lipase treatment step was carried out in the same manner as in Example 1, except that the types of edible fats and oils and lipase were changed as shown in Table 1 below. In addition, an alkali isomerization process was carried out in the same manner as in Example 1, except that the type of alkali compound, the molar concentration in the reaction solution, the reaction temperature, and the reaction time were changed as shown in Table 1 below, to produce a flavored oil or fat composition.

[0132] [Example 11] A flavored oil and fat composition was produced by carrying out the alkali isomerization step without carrying out the lipase treatment step. The alkali isomerization step was carried out in the same manner as in Example 1, except that the reaction temperature and reaction time were changed as shown in Table 1 below.

[0133] [Table 1]

[0134] The raw materials used in Examples 1 to 11 are as follows. (1) Edible fats and oils Linseed oil (α-linolenic acid content in the total amount of constituent fatty acids: 52.1% by mass, linoleic acid content: 16.8% by mass) Perilla oil (α-linolenic acid content of the total fatty acids: 58.9% by mass, linoleic acid content: 15.9% by mass) (2) Lipase Lipase A: Lipase AY "Amano" 30SD (manufactured by Amano Enzyme Co., Ltd.) Lipase B: Lipase OF (manufactured by Meito Sangyo Co., Ltd.)

[0135] The flavor oil compositions produced in Examples 1 to 11 were analyzed for their constituents and peroxide value (the number of milliequivalents of iodine liberated from potassium iodide by 1 kg of the flavor oil composition) by the standard method for analyzing fats and oils. The results are shown in Table 2 below.

[0136] [Table 2]

[0137] The compounds listed in Table 2 are as follows: Here, for example, "c9" means that the 9th position of the fatty acid is cis (E form), and "t11" means that the 11th position of the fatty acid is trans (Z form). In addition, the term "peroxide" refers to a fatty acid in which at least one double bond of an unsaturated fatty acid is oxidized to have at least one hydroxyperoxide group (-OOH).

[0138] [ka]

[0139] The results in Table 2 show that compound A, which provides a refreshing sensation, can be obtained by isomerizing the α-linolenic acid and linoleic acid contained in flaxseed oil or perilla oil through the alkaline isomerization process.

[0140] [Example 12] A flavored oil and fat composition was produced by carrying out a lipase treatment step, an alkali isomerization step, and then an oxidation step.

[0141] (oxidation process) 100 g of the flavor oil composition (composition to be oxidized) produced in Example 4 was placed in a beaker, heated to 103°C in an oil bath, and stirred at 200 rpm for 0.5 hours while bubbling dry air at 3 mL / min, thereby producing a flavor oil composition.

[0142] [Examples 13 to 20, Reference Examples 1 to 4] As shown in Table 3 below, flavor oil compositions were produced in the same manner as in Example 12, except that the type of flavor oil composition (composition to be oxidized) used as the raw material was changed, HO sunflower oil (manufactured by J Oil Mills Co., Ltd.) was further added as an additive to the flavor oil composition (composition to be oxidized), and the oxidation temperature and oxidation time were changed.

[0143] [Table 3]

[0144] The content of compound A (C9t11C15) and the peroxide value (POV) of the flavor oil and fat compositions produced in Examples 12 to 20 and Reference Examples 1 to 4 were measured in the same manner as in Examples 1 to 11. The results obtained are shown in Table 4 below.

[0145] [Table 4]

[0146] The flavor oil and fat composition (Example 4) which was the raw material for Examples 12 to 19 had a compound A (C9t11C15) content of 28.1 mass %, a peroxide content of 4.0 mass %, and a POV of 3.3 meq / kg. In addition, the flavor oil and fat composition (Example 8) that was the raw material of Example 20 had a compound A (C9t11C15) content of 17.2 mass %, a peroxide content of 7.9 mass %, and a POV of 18.2 meq / kg. Therefore, it can be seen from the results in Table 4 that the oxidation of compound A (C9t11C15) etc. progressed through the oxidation step, and a hydroperoxide group (-OOH) was introduced.

[0147] [evaluation] The flavor oil and fat compositions were evaluated for use on food materials for frying (cooking with heat) and food materials for non-cooking with heat.

[0148] (Effect on fried foods) As shown in Table 5 below, the flavor oil and fat composition was added to palm oil (Frying Oil J, manufactured by J Oil Mills, Inc.), and the effect on food materials for frying was evaluated. The ingredients used for frying included french fries (shoestrings, manufactured by McCain Foods Japan, Inc.), fried chicken (boneless fried chicken, manufactured by Ajinomoto Frozen Foods Co., Ltd.), and croquettes (NEW Delica Croquettes, manufactured by Ajinomoto Frozen Foods Co., Ltd.). The frying was performed by frying each food material in palm oil containing the flavored oil and fat composition. Specifically, the french fries were fried for 20 minutes, the fried chicken for 5 minutes, and the croquettes for 5 minutes.

[0149] In addition, as Comparative Example 1, palm oil was used as it was and fried in the same manner as above.

[0150] The fried food ingredients (french fries, fried chicken, and croquettes) obtained by frying were evaluated for refreshing feeling, sharp aftertaste, and off-flavor according to the following criteria. The evaluation was performed by three evaluators, and the average value was used as the evaluation result. The results are shown in Table 5 below.

[0151] (1) Cool feeling 0 points: No cooling sensation 1 point: A slight cooling sensation 2 points: Feels slightly cool 3 points: Strong cooling sensation 4 points: A strong cooling sensation 5 points: Feels quite cool

[0152] (2) Sharp aftertaste 0 points: No sharp aftertaste compared to Comparative Example 1 1 point: Slightly sharper aftertaste than Comparative Example 1 2 points: The aftertaste is slightly stronger than that of Comparative Example 1. 3 points: Slightly sharper aftertaste than Comparative Example 1 4 points: The aftertaste is sharper than that of Comparative Example 1 5 points: The aftertaste is much sharper than that of Comparative Example 1.

[0153] (3) Unusual flavor 0 points: No off-flavors 1 point: Slightly strange flavor 2 points: Slightly flavorful 3 points: Strong strange flavor 4 points: A slightly strong strange flavor is felt 5 points: A very strong strange flavor

[0154] [Table 5]

[0155] From the results in Table 5, it can be seen that a refreshing sensation (refreshing sensation) can be imparted by frying food materials using palm oil containing the flavor oil and fat composition of the Examples. In addition, for example, when comparing Example 4, which did not undergo an oxidation process, with Examples 13, 16, and 18 to 19, which did undergo an oxidation process, it was found that the oxidation process provided a higher refreshing sensation (refreshing sensation).

[0156] (Effect on non-heated cooking ingredients) As shown in Table 6 below, the flavor oil and fat composition was added to food materials for non-heat cooking, and the effect on the food materials for non-heat cooking was evaluated. The ingredients used for non-heated cooking were unsweetened soy milk (Oishii Unsweetened Soy Milk, Kikkoman Corporation), banana soy milk (Soy Milk Drink Banana, Kikkoman Corporation), yogurt (Bulgaria Yogurt, Meiji Corporation), and ice cream (Super Cup, Meiji Corporation).

[0157] Also, soybean oil was used as Comparative Example 2.

[0158] The obtained non-heated cooking food materials (unsweetened soy milk, banana soy milk, yogurt, and ice cream) were evaluated for refreshing feeling and sharpness of aftertaste according to the following criteria. The evaluation was performed by three evaluators, and the average value was used as the evaluation result. The obtained results are shown in Table 6 below.

[0159] (1) Cool feeling 0 points: No cooling sensation 1 point: A slight cooling sensation 2 points: Feels slightly cool 3 points: Strong cooling sensation 4 points: A strong cooling sensation 5 points: Feels quite cool

[0160] (2) Sharp aftertaste 0 points: No sharp aftertaste compared to Comparative Example 2 1 point: Slightly sharper aftertaste than Comparative Example 2 2 points: The aftertaste is slightly stronger than that of Comparative Example 2. 3 points: Slightly sharper aftertaste than Comparative Example 2 4 points: The aftertaste is sharper than that of Comparative Example 2 5 points: The aftertaste is much sharper than that of Comparative Example 2

[0161] [Table 6]

[0162] The results in Table 6 show that the addition of the flavor oil and fat compositions of the examples could impart a refreshing feeling (refreshing feeling) to the foodstuffs for non-heated cooking.

Claims

1. The following formula: 【Chemistry 1】 The flavor oil composition comprises at least one of a conjugated diene compound represented by the formula (I) and a peroxide thereof.

2. The flavor oil composition according to claim 1, wherein the total content of the conjugated diene compound and its peroxide is 5% by mass or more and 80% by mass or less, based on the total mass of the flavor oil composition.

3. 2. The flavor oil composition of claim 1, having a peroxide value (POV) of less than 10 meq / kg.

4. The flavor oil composition according to claim 1, having a peroxide value (POV) of 10 meq / kg or more and 130 meq / kg or less.

5. The flavor oil composition according to claim 1, which is for use in cooking.

6. The flavor oil composition according to claim 1, which is for use in non-heat cooking.

7. A reaction solution containing an edible oil and fat having an α-linolenic acid content of 0.1 to 80% by mass of the total amount of constituent fatty acids and an alkaline compound is prepared by subjecting a fatty acid to a process represented by the following formula: 【Chemistry 2】 The present invention relates to a method for producing a flavor oil composition, the method comprising the steps of:

8. The method according to claim 7 , wherein the alkali isomerization step is carried out at a temperature of 110° C. or higher and 230° C. or lower.

9. The method according to claim 7, wherein the alkaline compound is selected from at least one of sodium hydroxide and potassium hydroxide.

10. The method according to claim 7, wherein the molar concentration of the alkaline compound in the reaction solution is 0.5 M or more and 5 M or less.

11. The method according to claim 7, further comprising an oxidation step of oxidizing the composition to be oxidized containing the conjugated diene compound at 80°C or higher and 180°C or lower to obtain a peroxide of the conjugated diene compound.

12. The method according to claim 11, wherein the oxidation time in the oxidation step is from 0.5 hours to 10 hours.

13. The method according to claim 11, wherein the oxidation step is carried out until the peroxide value (POV) of the flavor oil or fat composition is 10 meq / kg or more and 130 meq / kg or less.

14. The method according to claim 11, wherein the content of the conjugated diene compound in the composition to be oxidized is 20 mass% or more based on the total mass of the composition to be oxidized.

15. The method according to claim 7, wherein the edible oil comprises at least one selected from the group consisting of perilla oil, linseed oil, and shiso oil.

16. A refreshing feeling imparting agent comprising the flavor oil or fat composition according to any one of claims 1 to 6.

17. A method for imparting a refreshing feeling, comprising imparting to a food material the flavor oil or fat composition according to any one of claims 1 to 6, or the flavor oil or fat composition produced by the method according to any one of claims 7 to 15.

18. The method for imparting a refreshing feeling according to claim 17, wherein the food material is for cooking by heating.

19. The method for imparting a refreshing feeling according to claim 17, wherein the food material is for cooking without heating.

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