Flavoring composition

Abstract

To provide a novel flavoring composition, a consumer product containing the flavoring composition, a method for improving the flavor of the flavoring composition, and a method for improving the flavor of the consumer product.SOLUTION: A flavoring composition contains a compound represented by formula (1), where a ratio of (4E) isomers of the compound to (4Z) isomers of the compound is (4E) isomers / (4Z) isomers=90 / 10 or more, where, among the (4E) isomers of the compound, a ratio of (4E,7E) isomers of the compound to (4E,7Z) isomers of the compound is (4E,7E) isomers / (4E,7Z) isomers=80 / 20 or more.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a flavoring composition, a consumer product containing the flavoring composition, and a method for improving the flavor of a flavoring composition and a method for improving the flavor of a consumer product. [Background technology]

[0002] Recently, consumer demands for foods, beverages, and cosmetics have become more sophisticated and diverse, with particular attention being focused on fragrance, with fragrance characteristics becoming an important factor in the appeal of a product. For example, there is an increasing demand for fragrance compounds that can be added to improve flavor, for example, to impart or enhance long-lasting, natural, voluminous, etc., to fragrances and tastes, and there is a continuing desire for the development of new fragrance compounds that can impart improved flavor to consumer products and differentiate them from the flavors of existing products.

[0003] Several proposals have been made to improve fragrance. For example, Patent Document 1 discloses 4-methyl-8-vinyl-4,7-nonadienal and 4-methyl-8-vinyl-4,8-nonadienal as intermediates in the synthesis of α-sinensal and β-sinensal, and describes that these compounds have a floral, incense-like fragrance with a pine-like aroma, and that adding these compounds to a fragrance composition enhances the top note (fragrance release). [Prior art documents] [Patent documents]

[0004] [Patent Document 1] U.S. Patent No. 3,963,783 Summary of the Invention [Problem to be solved by the invention]

[0005] However, the compound described in Patent Document 1 is intended primarily for use as a synthetic intermediate, and the details thereof have not been made clear.

[0006] An object of the present invention is to provide a new flavoring composition, a consumer product containing the flavoring composition, a method for improving the flavor of a flavoring composition, and a method for improving the flavor of a consumer product. [Means for solving the problem]

[0007] The present inventors have found that a composition containing the cis-trans isomers of the above compound in a specific ratio is useful as a new flavor-imparting composition, and have completed the present invention. Representative inventions disclosed in this application can be briefly summarized as follows.

[0008] [1] A flavor-imparting composition comprising a compound represented by formula (1), wherein the ratio of the (4E) form of the compound to the (4Z) form of the compound is (4E) form / (4Z) form=90 / 10 or more, and within the (4E) form of the compound, the ratio of the (4E,7E) form of the compound to the (4E,7Z) form of the compound is (4E,7E) form / (4E,7Z) form=80 / 20 or more.

[0009] [ka]

[0010] [2] A flavor-imparting composition containing a compound represented by formula (1), wherein the ratio of the (4E) form of the compound to the (4Z) form of the compound is (4E) form / (4Z) form=90 / 10 or more, and within the (4E) form of the compound, the ratio of the (4E,7E) form of the compound to the (4E,7Z) form of the compound is (4E,7E) form / (4E,7Z) form=more than 60 / 40 but not more than 70 / 30.

[0011] [ka]

[0012] [3] A flavor-imparting composition containing a compound represented by formula (1), wherein the ratio of the (4E) form of the compound to the (4Z) form of the compound is (4E) form / (4Z) form=90 / 10 or more, and within the (4E) form of the compound, the ratio of the (4E,7E) form of the compound to the (4E,7Z) form of the compound is (4E,7E) form / (4E,7Z) form=60 / 40 or less.

[0013] [ka]

[0014] [4] A flavor-imparting composition containing a compound represented by formula (1), wherein the ratio of the (4E) form of the compound to the (4Z) form of the compound is (4E) form / (4Z) form = 10 / 90 or less.

[0015] [ka]

[0016] [5] The flavor-imparting composition according to [4], wherein, in the (4Z) form of the compound, the ratio of the (4Z,7E) form of the compound to the (4Z,7Z) form of the compound is (4Z,7E) form / (4Z,7Z) form = 60 / 40 or more. [6] A flavor-imparting composition according to [1] or [2], wherein the concentration of the compound is in the range of 0.05% or more and 5% or less, based on the total mass of the flavor-imparting composition. [7] The flavor-imparting composition according to [3], wherein the concentration of the compound is in the range of 0.005% or more and 0.5% or less, based on the total mass of the flavor-imparting composition. [8] A flavor-imparting composition according to [4] or [5], wherein the concentration of the compound is in the range of 0.05% or more and 1% or less, based on the total mass of the flavor-imparting composition. [9] The flavor-imparting composition according to any one of [1] to [5], which is a fragrance composition for cosmetics.

[10] The flavor-imparting composition according to any one of [1] to [5], which is a flavor composition for food or drink.

[11] A method for improving the flavor of a flavor-imparting composition, comprising the step of adding the flavor-imparting composition according to any one of [1] to [5] to another flavor-imparting composition.

[12] A consumer product containing the flavor-imparting composition according to any one of [1] to [5].

[13] A method for improving the flavor of consumer goods, comprising the step of adding the flavor-imparting composition according to any one of [1] to [5] to the consumer goods. [Effects of the Invention]

[0017] According to the present invention, it is possible to provide a novel flavor-imparting composition, a consumer product containing the flavor-imparting composition, a method for improving the flavor of a flavor-imparting composition, and a method for improving the flavor of a consumer product. DETAILED DESCRIPTION OF THE INVENTION

[0018] An embodiment of the present invention will be described in detail below. In this specification, the symbols "to" indicate a range including a lower limit and an upper limit, and "concentration" and "%" represent "mass concentration" and "mass percent concentration," respectively, unless otherwise specified. Furthermore, in this specification, flavor refers to one or more senses that can be changed by aroma (fragrance), typically including smell and taste. In this specification, "imparting or enhancing an aroma" includes adding a new aroma or enhancing an aroma, and includes, for example, improving flavor as a result of adding an aroma. Furthermore, the addition or enhancement of an aroma may enhance, suppress, or improve sensations other than smell and taste, such as coolness, warmth, texture (e.g., smoothness in the throat, hardness, viscosity, etc., also known as texture), and stimulating sensations such as carbonation and spiciness.

[0019] <Flavor-imparting composition (1)> The flavor-imparting composition according to a first embodiment of the present invention (hereinafter sometimes referred to as "the flavor-imparting composition (1)") is a flavor-imparting composition containing a compound represented by the following formula (1) (4,8-dimethyl-4,7,9-decatrienal, hereinafter sometimes referred to as "the compound"), in which the ratio of the (4E) isomer of the compound represented by the following formula (2) to the (4Z) isomer of the compound represented by the following formula (3) is (4E) isomer / (4Z) isomer = 90 / 10 or more, and among the (4E) isomers of the compound, the ratio of the (4E,7E) isomer of the compound represented by the following formula (4) to the (4E,7Z) isomer of the compound represented by the following formula (5) is (4E,7E) isomer / (4E,7Z) isomer = 80 / 20 or more.

[0020] [ka]

[0021] [ka]

[0022] [ka]

[0023] [ka]

[0024] [ka]

[0025] In the present flavor-imparting composition (1), the phrase "the ratio of the (4E) form of the present compound to the (4Z) form of the present compound is (4E) form / (4Z) form = 90 / 10 or more" means that the ratio of the (4E) form of the present compound to the (4Z) form of the present compound is 90:10 to 100:0. However, the expression "100:0" (4E) form:(4Z) form means that the present flavor-imparting composition (1) is substantially free of the (4Z) form and contains only the (4E) form, i.e., the ratio of the (4E) form:(4Z) form = 99.99:0.00 (the same applies to other embodiments below). Similarly, in the present flavor-imparting composition (1), "the ratio of the (4E,7E) isomer of the present compound to the (4E,7Z) isomer of the present compound is (4E,7E) isomer / (4E,7Z) isomer = 80 / 20 or more" means that the ratio of the (4E,7E) isomer of the present compound to the (4E,7Z) isomer of the present compound is 80:20 to 100:0. However, "100:0" (4E,7E) isomer:(4E,7Z) isomer means that the present flavor-imparting composition (1) contains substantially no (4E,7Z) isomer and contains only the (4E,7E) isomer, i.e., a ratio of (4E,7E) isomer:(4E,7Z) isomer = 99.99:0.00 (the same applies to other embodiments below).

[0026] The present inventors have discovered the surprising usefulness of a composition containing the present compound in a specific cis-trans isomer ratio according to one embodiment of the present invention, exhibiting an exceptionally excellent flavor-improving effect, as shown in the examples below, and have thus arrived at the present invention. In particular, the present flavor-imparting composition (1) contains the present compound's cis-trans isomers in the above ratio, thereby exhibiting a sharp, green floral, calamus-like odor and exhibiting excellent naturalness, diffusibility, and lingering aroma. Therefore, by adding the present flavor-imparting composition (1) to various products, it can impart a flavor to the products or improve the flavor of the products. More specifically, adding the present flavor-imparting composition (1) to various products can impart a sharp, green floral, calamus-like odor and produce products with excellent naturalness, diffusibility, and lingering aroma. Here, "calamus" refers to a plant whose Japanese name is Shobu (iris) and whose scientific name is Acorus calamus L. When describing a scent as "calamus-like," it refers to a scent similar to calamus essential oil (obtained by steam distillation of calamus root).

[0027] The products to which the present flavor-imparting composition (1) can be added are not particularly limited, but examples include consumer goods such as cosmetics, foods, and beverages (the same applies to "the present flavor-imparting composition (2)" to "the present flavor-imparting composition (5)" described below). Furthermore, the present flavor-imparting composition (1) can be added to various flavor compositions to impart a fragrance to the flavor composition or to improve the fragrance of the flavor composition (the same applies to "the present flavor-imparting composition (2)" to "the present flavor-imparting composition (5)" described below).

[0028] Each isomer of the compound of the present invention may be obtained by any method available to those skilled in the art, but can be synthesized, for example, by the methods described in the Examples. The cis-trans isomer ratio of the present compound constituting the present flavor-imparting composition (1) can be controlled as desired by synthesizing and / or purifying each of the isomers: the (4E,7E) isomer represented by the above formula (4), the (4E,7Z) isomer represented by the above formula (5), the (4Z,7E) isomer represented by the following formula (6), and the (4Z,7Z) isomer represented by the following formula (7), and then appropriately mixing these isomers (see the Examples below). The cis-trans isomer ratio of the present compound in the prepared flavor-imparting composition (1) can be confirmed by gas chromatography (GC), for example, using the apparatus and conditions described in the Examples (the same applies hereinafter to the flavor-imparting composition according to this embodiment).

[0029] [ka]

[0030] [ka]

[0031] The concentration of the present compound in the present flavor-imparting composition (1) can be determined arbitrarily depending on the intended use (purpose of use) of the present flavor-imparting composition and the target to which it is added. However, when the present flavor-imparting composition (1) is used as a fragrance composition for cosmetics, the concentration can be, for example, within a range of 0.001% to 50%, preferably 0.05% to 5%, based on the total mass of the present flavor-imparting composition (1). More specifically, the lower limit can be any of 0.001%, 0.01%, 0.1%, 1%, 5%, 10%, 20%, 30%, or 40%, and the upper limit can be any of 50%, 40%, 30%, 20%, 10%, 1%, 0.1%, or 0.01%, and the range can be any combination of these lower and upper limits, but is not limited to these. Although the concentration of the present compound in the present flavoring composition (1) depends on the formulation and fragrance tone of the cosmetic fragrance composition for which the present flavoring composition (1) is used, a high fragrance-imparting effect is perceived when the concentration is 0.001% or higher, and a concentration of 50% or lower results in a high fragrance-imparting effect while preventing the scent of the present compound from becoming too strong and preventing undesirable changes in the fragrance characteristics of the cosmetic fragrance composition. In particular, when the concentration of the present compound in the present flavoring composition (1) is within the range of 0.05% to 5%, a sharp green note is added, resulting in a refreshing, clearly defined, lily of the valley-like fragrance characteristic with an excellent natural feel. However, depending on the fragrance tone of the cosmetic fragrance composition, the present compound may be used at a concentration below the lower limit or above the upper limit.

[0032] Furthermore, when the present flavor-imparting composition (1) is used as a flavor composition for foods and beverages, the range is, for example, 10 ppb to 10%, preferably 1000 ppb to 1%, based on the total mass of the present flavor-imparting composition (1). More specifically, the lower limit may be any of 10 ppb, 100 ppb, 1 ppm, 10 ppm, 100 ppm, 0.1%, or 1%, and the upper limit may be any of 10%, 1%, 0.1%, 100 ppm, 10 ppm, 1 ppm, or 100 ppb, and the range may be any combination of these lower and upper limits, but is not limited to these. Although it depends on the formulation and fragrance tone of the flavor composition for food and beverages, which is the intended use of the flavor-imparting composition (1), a high flavor-imparting effect is felt when the concentration of the present compound in the flavor-imparting composition (1) is 10 ppb or more, and when it is 10% or less, the scent derived from the present compound does not become too strong, and undesirable alteration of the flavor characteristics of the flavor composition for food and beverages can be suppressed. However, depending on the fragrance tone of the flavor composition for food and beverages, the present compound may be used at a concentration below the lower limit or above the upper limit.

[0033] <Flavor-imparting composition (2)> A flavor-imparting composition according to a second embodiment of the present invention (hereinafter sometimes referred to as "the present flavor-imparting composition (2)") is a flavor-imparting composition containing the present compound, in which the ratio of the (4E) form of the present compound to the (4Z) form of the present compound is (4E) form / (4Z) form=90 / 10 or more, and within the (4E) form of the present compound, the ratio of the (4E,7E) form of the present compound to the (4E,7Z) form of the present compound is (4E,7E) form / (4E,7Z) form=more than 60 / 40 but not more than 70 / 30.

[0034] In the present flavor-imparting composition (2), the phrase "the ratio of the (4E,7E) form of the present compound to the (4E,7Z) form of the present compound is (4E,7E) form / (4E,7Z) form = more than 60 / 40 but not more than 70 / 30" means that the ratio is more than "60:40" but not more than "70:30" for the (4E,7E) form of the present compound:(4E,7Z) form of the present compound.

[0035] The present flavor-imparting composition (2) contains the cis-trans isomers of the present compound in the above ratio, and thus has a fresh, floral, green-like odor and is excellent in naturalness, diffusibility, and lingering aroma. Therefore, by adding the present flavor-imparting composition (2) to various articles, it is possible to impart a flavor to the article or improve the flavor of the article. More specifically, by adding the present flavor-imparting composition (2) to various articles, it is possible to impart a fresh, floral, green-like odor and produce articles that are excellent in naturalness, diffusibility, and lingering aroma.

[0036] The concentration of the present compound in the present flavor-imparting composition (2) can be determined arbitrarily depending on the intended use (purpose of use) of the present flavor-imparting composition and the target to which it is added. However, when the present flavor-imparting composition (2) is used as a fragrance composition for cosmetics, the concentration can be, for example, within a range of 0.001% to 50%, preferably 0.05% to 5%, based on the total mass of the present flavor-imparting composition (2). More specifically, the lower limit can be any of 0.001%, 0.01%, 0.1%, 1%, 5%, 10%, 20%, 30%, or 40%, and the upper limit can be any of 50%, 40%, 30%, 20%, 10%, 1%, 0.1%, or 0.01%, and the range can be any combination of these lower and upper limits, but is not limited to these. Although the concentration of the present compound in the present flavoring composition (2) depends on the formulation and fragrance tone of the cosmetic fragrance composition for which the present flavoring composition (2) is intended to be used, a high fragrance-imparting effect is perceived when the concentration of the present compound in the present flavoring composition (2) is 0.001% or higher, and a concentration of 50% or lower results in a high fragrance-imparting effect while preventing the scent derived from the present compound from becoming too strong and preventing undesirable changes in the fragrance characteristics of the cosmetic fragrance composition. In particular, when the concentration of the present compound in the present flavoring composition (2) is within the range of 0.05% to 5%, a refreshing, clean, lily of the valley-like, green fragrance is produced for a long-lasting effect, resulting in an excellent natural feel. However, depending on the fragrance tone of the cosmetic fragrance composition, the present compound may be used at a concentration below the lower limit or above the upper limit.

[0037] Furthermore, when the present flavor-imparting composition (2) is used as a flavor composition for foods and beverages, the range is, for example, 10 ppb to 10%, preferably 1000 ppb to 1%, based on the total mass of the present flavor-imparting composition (2). More specifically, the lower limit may be any of 10 ppb, 100 ppb, 1 ppm, 10 ppm, 100 ppm, 0.1%, or 1%, and the upper limit may be any of 10%, 1%, 0.1%, 100 ppm, 10 ppm, 1 ppm, or 100 ppb, and the range may be any combination of these lower and upper limits, but is not limited to these. Although it depends on the formulation and fragrance tone of the flavor composition for food and beverages, which is the intended use of the flavor-imparting composition (2), a high flavor-imparting effect is felt when the concentration of the present compound in the flavor-imparting composition (2) is 10 ppb or more, and when it is 10% or less, the scent derived from the present compound does not become too strong, and undesirable alteration of the flavor characteristics of the flavor composition for food and beverages can be suppressed. However, depending on the fragrance tone of the flavor composition for food and beverages, the present compound may be used at a concentration below the lower limit or above the upper limit.

[0038] <Flavor-imparting composition (3)> A flavor-imparting composition according to a third embodiment of the present invention (hereinafter sometimes referred to as "the present flavor-imparting composition (3)") is a flavor-imparting composition containing the present compound, wherein the ratio of the (4E) isomer of the present compound to the (4Z) isomer of the present compound is (4E) isomer / (4Z) isomer = 90 / 10 or more, and within the (4E) isomer of the present compound, the ratio of the (4E,7E) isomer of the present compound to the (4E,7Z) isomer of the present compound is (4E,7E) isomer / (4E,7Z) isomer = 60 / 40 or less.

[0039] In the present flavor-imparting composition (3), the phrase "the ratio of the (4E,7E) isomer of the present compound to the (4E,7Z) isomer of the present compound is (4E,7E) isomer / (4E,7Z) isomer = 60 / 40 or less" means that the ratio of the (4E,7E) isomer of the present compound to the (4E,7Z) isomer of the present compound is 0:100 to 60:40. However, the expression "0:100" means that the present flavor-imparting composition (3) contains substantially no (4E,7E) isomer and contains only the (4E,7Z) isomer, i.e., a ratio of 0.00:99.99 (the same applies to other embodiments below).

[0040] The present flavor-imparting composition (3) contains the cis-trans isomers of the present compound in the above ratio, and thus has a realistic lily of the valley-like aroma and is excellent in naturalness, diffusibility, and lingering aroma. Therefore, by adding the present flavor-imparting composition (3) to various articles, it is possible to impart a flavor to the article or improve the flavor of the article. More specifically, by adding the present flavor-imparting composition (3) to various articles, it is possible to impart a realistic lily of the valley-like aroma and to produce articles that are excellent in naturalness, diffusibility, and lingering aroma.

[0041] The concentration of the present compound in the present flavor-imparting composition (3) can be determined arbitrarily depending on the intended use (purpose of use) of the present flavor-imparting composition and the target to which it is added. However, when the present flavor-imparting composition (3) is used as a fragrance composition for cosmetics, the concentration can be, for example, within a range of 0.0001% to 5%, preferably 0.005% to 0.5%, based on the total mass of the present flavor-imparting composition (3). More specifically, the lower limit can be any of 0.0001%, 0.001%, 0.01%, 0.1%, 1%, 2%, 3%, or 4%, and the upper limit can be any of 5%, 4%, 3%, 2%, 1%, 0.1%, 0.01%, or 0.001%, and the range can be any combination of these lower and upper limits, but is not limited to these. Although the concentration of the present compound in the present flavor-imparting composition (3) depends on the formulation and fragrance tone of the cosmetic fragrance composition for which the present flavor-imparting composition (3) is intended, a high fragrance-imparting effect is perceived when the concentration is 0.0001% or higher, and a concentration of 5% or lower results in a high fragrance-imparting effect while preventing the fragrance derived from the present compound from becoming too strong and preventing undesirable changes in the fragrance characteristics of the cosmetic fragrance composition. In particular, when the concentration of the present compound in the present flavor-imparting composition (3) is within the range of 0.005% to 0.5%, a green, richly sweet, lily of the valley fragrance with a well-balanced overall fragrance or a rich, fresh, realistic lily of the valley fragrance with an excellent natural feel is achieved. However, depending on the fragrance tone of the cosmetic fragrance composition, concentrations below the above lower limit or above the above upper limit may be used.

[0042] Furthermore, when the present flavor-imparting composition (3) is used as a flavor composition for foods and beverages, the range is, for example, 10 ppb to 10%, preferably 1000 ppb to 1%, based on the total mass of the present flavor-imparting composition (3). More specifically, the lower limit may be any of 10 ppb, 100 ppb, 1 ppm, 10 ppm, 100 ppm, 0.1%, or 1%, and the upper limit may be any of 10%, 1%, 0.1%, 100 ppm, 10 ppm, 1 ppm, or 100 ppb, and the range may be any combination of these lower and upper limits, but is not limited to these. Although it depends on the formulation and fragrance tone of the flavor composition for food and beverages, which is the intended use of the flavor-imparting composition (3), a high flavor-imparting effect is felt when the concentration of the present compound in the flavor-imparting composition (3) is 10 ppb or more, and when it is 10% or less, the scent derived from the present compound does not become too strong, and undesirable changes in the flavor characteristics of the flavor composition for food and beverages can be suppressed. However, depending on the fragrance tone of the flavor composition for food and beverages, the present compound may be used at a concentration below the lower limit or above the upper limit.

[0043] <Flavor-imparting composition (4)> A flavor-imparting composition according to a fourth embodiment of the present invention (hereinafter sometimes referred to as "the flavor-imparting composition (4) of the present invention") is a flavor-imparting composition containing the present compound, in which the ratio of the (4E) form of the present compound to the (4Z) form of the present compound is (4E) form / (4Z) form = 10 / 90 or less.

[0044] In the present flavor-imparting composition (4), the phrase "the ratio of the (4E) form of the present compound to the (4Z) form of the present compound is (4E) form / (4Z) form = 10 / 90 or less" means that the ratio of the (4E) form of the present compound to the (4Z) form of the present compound is 0:100 to 10:90. However, the expression "0:100" means that the present flavor-imparting composition (4) is substantially free of the (4E) form and contains only the (4Z) form, i.e., the ratio of the (4E) form:(4Z) form is 0.00:99.99 (the same applies to other embodiments below).

[0045] The present flavor-imparting composition (4) contains the cis-trans isomers of the present compound in the above ratio, and thus has a mint-like aroma and is excellent in naturalness, diffusibility, and lingering aroma. Therefore, by adding the present flavor-imparting composition (4) to various articles, it is possible to impart a flavor to the article or improve the flavor of the article. More specifically, by adding the present flavor-imparting composition (4) to various articles, it is possible to impart a mint-like aroma and produce articles with naturalness, diffusibility, and lingering aroma.

[0046] The concentration of the present compound in the present flavor-imparting composition (4) can be determined arbitrarily depending on the intended use (purpose of use) of the present flavor-imparting composition and the target to which it is added. However, when the present flavor-imparting composition (4) is used as a fragrance composition for cosmetics, the concentration can be, for example, within a range of 0.001% to 50%, preferably 0.05% to 1%, based on the total mass of the present flavor-imparting composition (4). More specifically, the lower limit can be any of 0.001%, 0.01%, 0.1%, 1%, 5%, 10%, 20%, 30%, or 40%, and the upper limit can be any of 50%, 40%, 30%, 20%, 10%, 1%, 0.1%, or 0.01%, and the range can be any combination of these lower and upper limits, but is not limited to these. Although the concentration of the present compound in the present flavoring composition (4) depends on the formulation and fragrance tone of the cosmetic fragrance composition for which the present flavoring composition (4) is intended to be used, a high fragrance-imparting effect is perceived when the concentration is 0.001% or higher, and a concentration of 50% or lower results in a high fragrance-imparting effect while preventing the scent of the present compound from becoming too strong and preventing undesirable changes in the fragrance characteristics of the cosmetic fragrance composition. In particular, when the concentration of the present compound in the present flavoring composition (4) is within the range of 0.05% to 1%, a refreshing lily of the valley scent with added green and mint notes or a fresh and refreshing lily of the valley scent with added violet and mint notes is achieved, resulting in an excellent natural feel. However, depending on the fragrance tone of the cosmetic fragrance composition, the present compound may be used at a concentration below the lower limit or above the upper limit.

[0047] Furthermore, when the present flavor-imparting composition (4) is used as a flavor composition for foods and beverages, the range is, for example, 10 ppb to 10%, preferably 100 ppb to 1%, based on the total mass of the present flavor-imparting composition (4). More specifically, the lower limit may be any of 10 ppb, 100 ppb, 1 ppm, 10 ppm, 100 ppm, 0.1%, or 1%, and the upper limit may be any of 10%, 1%, 0.1%, 100 ppm, 10 ppm, 1 ppm, or 100 ppb, and the range may be any combination of these lower and upper limits, but is not limited to these. Although it depends on the formulation and fragrance tone of the flavor composition for food and beverages, which is the intended use of the flavor-imparting composition (4), when the concentration of the present compound in the flavor-imparting composition (4) is 10 ppb or more, a high flavor-imparting effect is felt, and when it is 10% or less, the scent derived from the present compound does not become too strong, and undesirable alteration of the flavor characteristics of the flavor composition for food and beverages can be suppressed. However, depending on the fragrance tone of the flavor composition for food and beverages, the present compound may be used at a concentration below the lower limit or above the upper limit.

[0048] <Flavor-imparting composition (5)> A flavor-imparting composition according to a fifth embodiment of the present invention (hereinafter sometimes referred to as "the present flavor-imparting composition (5)") is a flavor-imparting composition containing the present compound, in which the ratio of the (4E) form of the present compound to the (4Z) form of the present compound is (4E) form / (4Z) form = 10 / 90 or less, and within the (4Z) form of the present compound, the ratio of the (4Z,7E) form of the present compound to the (4Z,7Z) form of the present compound is (4Z,7E) form / (4Z,7Z) form = 60 / 40 or more.

[0049] In the present flavor-imparting composition (5), the phrase "the ratio of the (4Z,7E) form of the present compound to the (4Z,7Z) form of the present compound is (4Z,7E) form / (4Z,7Z) form = 60 / 40 or more" means that the ratio of the (4Z,7E) form of the present compound to the (4Z,7Z) form of the present compound is 60:40 to 100:0. However, the ratio of (4Z,7E) form:(4Z,7Z) form = 100:0 means that the present flavor-imparting composition (5) is substantially free of the (4Z,7Z) form and contains only the (4Z,7E) form, i.e., a ratio of (4Z,7E) form:(4Z,7Z) form = 99.99:0.00 (the same applies to other embodiments below).

[0050] The present flavor-imparting composition (5) is the present flavor-imparting composition (4) described above, but is configured so that the (4Z,7E) isomer is contained in greater amounts than the (4Z,7Z) isomer. The present flavor-imparting composition (5) contains the cis-trans isomers of the present compound in the above ratio, and thus has a sharp mint-like and violet-like aroma and is excellent in natural aroma, diffusibility, and lingering aroma. Therefore, by adding the present flavor-imparting composition (5) to various articles, it is possible to impart a flavor to the article or improve the flavor of the article. More specifically, by adding the present flavor-imparting composition (5) to various articles, it is possible to impart a sharp mint-like and violet-like aroma to the article and to produce an article having a natural aroma, diffusibility, and lingering aroma.

[0051] The concentration of the present compound in the present flavor-imparting composition (5) can be determined arbitrarily depending on the intended use (purpose of use) of the present flavor-imparting composition and the target to which it is added. However, when the present flavor-imparting composition (5) is used as a fragrance composition for cosmetics, the concentration can be, for example, within a range of 0.001% to 50%, preferably 0.05% to 1%, based on the total mass of the present flavor-imparting composition (5). More specifically, the lower limit can be any of 0.001%, 0.01%, 0.1%, 1%, 5%, 10%, 20%, 30%, or 40%, and the upper limit can be any of 50%, 40%, 30%, 20%, 10%, 1%, 0.1%, or 0.01%, and the range can be any combination of these lower and upper limits, but is not limited to these. Although the concentration of the present compound in the present flavoring composition (5) depends on the formulation and fragrance tone of the cosmetic fragrance composition for which the present flavoring composition (5) is used, a high fragrance-imparting effect is perceived when the concentration is 0.001% or higher, and a concentration of 50% or lower results in a high fragrance-imparting effect while preventing the scent of the present compound from becoming too strong and preventing undesirable changes in the fragrance characteristics of the cosmetic fragrance composition. In particular, when the concentration of the present compound in the present flavoring composition (5) is within the range of 0.05% to 1%, a violet and mint note is added, resulting in a fresh, refreshing, lily of the valley-like fragrance with an excellent natural feel. However, depending on the fragrance tone of the cosmetic fragrance composition, the present compound may be used at a concentration below the lower limit or above the upper limit.

[0052] Furthermore, when the present flavor-imparting composition (5) is used as a flavor composition for foods and beverages, the range is, for example, 10 ppb to 10%, preferably 100 ppb to 1%, and more preferably 1 ppm to 0.1%, based on the total mass of the present flavor-imparting composition (5). More specifically, the lower limit may be any of 10 ppb, 100 ppb, 1 ppm, 10 ppm, 100 ppm, 0.1%, or 1%, and the upper limit may be any of 10%, 1%, 0.1%, 100 ppm, 10 ppm, 1 ppm, or 100 ppb, and the range may be any combination of these lower and upper limits, but is not limited to these. Although it depends on the formulation and fragrance tone of the flavor composition for food and beverages for which the flavor-imparting composition (5) is intended to be used, a high flavor-imparting effect is felt when the concentration of the present compound in the flavor-imparting composition (5) is 10 ppb or more, and when it is 10% or less, the scent derived from the present compound does not become too strong, and undesirable alteration of the flavor characteristics of the flavor composition for food and beverages can be suppressed. However, depending on the fragrance tone of the flavor composition for food and beverages, the present compound may be used at a concentration below the lower limit or above the upper limit.

[0053] <Method for producing the present compound (synthesis example)> The cis-trans isomers of the compound of the present invention, i.e., the (4E,7E) isomer, the (4E,7Z) isomer, the (4Z,7E) isomer, and the (4Z,7Z) isomer of the compound of formula (1), can be separately produced by, for example, the following steps, although the synthesis method is not limited to these.

[0054] The (4E,7Z) and (4Z,7Z) isomers are synthesized by constructing the moiety that ultimately becomes (7Z) by a Wittig reaction with a ketone to obtain a common intermediate that can produce both isomers. The moiety that ultimately becomes (4E) is then constructed by a Claisen rearrangement of vinyl alcohol, and the moiety that ultimately becomes (4Z) is then constructed by a Wittig reaction with a ketone. Purification may be performed by vacuum distillation or column chromatography, if necessary.

[0055] The (4E,7E) and (4Z,7E) isomers are synthesized by constructing the part that will ultimately become (7E) by deconjugation reaction of unsaturated ester with lithium diisopropylamide to obtain a common intermediate that can produce both isomers. After that, the part that will ultimately become (4E) is constructed by Claisen rearrangement of vinyl alcohol, and the part that will ultimately become (4Z) is constructed by Wittig reaction of ketone. If necessary, purification can be performed by vacuum distillation or column chromatography.

[0056] As described above, after each cis-trans isomer is separately produced, the isomers are mixed appropriately in a desired ratio to prepare the flavor-imparting compositions (1) to (5) of the present invention.

[0057] <Fragrance composition> As described above, still another embodiment of the present invention provides an application of the present flavor-imparting compositions (1) to (5) (hereinafter, these may be collectively referred to simply as "the present flavor-imparting compositions") as flavor compositions (hereinafter, they may be referred to as "the present flavor compositions"). The present flavor compositions can be added to various articles for the purpose of imparting flavor. Specific examples thereof include, as described above, flavor compositions for cosmetics (also referred to as fragrance compositions) and flavor compositions for food and beverages (also referred to as flavor compositions). Examples of articles to which the present flavor compositions can be added include, as described above, various consumer goods such as cosmetics, food and beverages, and other miscellaneous goods. The form of the present flavor compositions is not particularly limited, and examples thereof include water-soluble flavor compositions, oil-soluble flavor compositions, emulsion flavor compositions, and powder flavor compositions.

[0058] The present fragrance composition contains the present compound, and "containing" encompasses embodiments in which the present composition contains an amount sufficient to exhibit the desired fragrance. Therefore, the present fragrance composition may contain only a mixture of the isomers of the present compound, but may also contain other fragrance ingredients and other additives such as solvents, as long as the desired fragrance is not impaired. Such other fragrance ingredients and other additives may be added for the purpose of ensuring that the fragrance composition (and the present compound contained in the composition) are dispersed uniformly at an appropriate concentration in the target substance.

[0059] Examples of such compounds or ingredients include various types of flavor compounds or flavor compositions, oil-soluble colorants, vitamins, functional substances, fish extracts, meat extracts, plant extracts, yeast extracts, animal and plant proteins, animal and plant protein hydrolysates, starch, dextrin, sugars, amino acids, nucleic acids, organic acids, solvents, etc. Examples include natural essential oils, natural flavors, and synthetic flavors described in "Patent Office Gazette, Collection of Well-Known and Commonly Used Techniques (Flavors) Part II Food Flavors, published January 14, 2000," "Survey on the Actual Use of Food Flavoring Compounds in Japan" (2000 Ministry of Health, Labor and Welfare Science Research Report, Japan Flavor and Flavor Manufacturers Association, published March 2001), and "Synthetic Flavors: Chemistry and Product Knowledge" (revised and expanded edition published December 20, 2016, edited by the Synthetic Flavor Editorial Committee, Chemical Daily Co., Ltd.).

[0060] Specific examples of synthetic fragrance compounds include hydrocarbon compounds such as monoterpenes such as α-pinene, β-pinene, γ-terpinene, myrcene, camphene, and limonene, sesquiterpenes such as valencene, cedrene, caryophyllene, and longifolene, and 1,3,5-undecatriene.

[0061] Examples of alcohol compounds include saturated alkanols such as butanol, pentanol, 3-octanol, and hexanol; unsaturated alcohols such as (Z)-3-hexen-1-ol, prenol, and 2,6-nonadienol; terpene alcohols such as linalool, geraniol, citronellol, tetrahydromyrcenol, farnesol, nerolidol, cedrol, α-terpineol, terpinen-4-ol, and borneol; and aromatic alcohols such as benzyl alcohol, phenylethyl alcohol, and cinnamyl alcohol.

[0062] Examples of aldehyde compounds include saturated aldehydes such as acetaldehyde, hexanal, octanal, decanal, and hydroxycitronellal; unsaturated aldehydes such as (E)-2-hexenal and 2,4-octadienal; terpene aldehydes such as citronellal, citral, myrtenal, and perillaldehyde; and aromatic aldehydes such as benzaldehyde, cinnamyl aldehyde, vanillin, ethyl vanillin, heliotropin, and p-tolyl aldehyde.

[0063] Examples of ketone compounds include saturated and unsaturated ketones such as 2-heptanone, 2-undecanone, 1-octen-3-one, acetoin, and 6-methyl-5-hepten-2-one (methylheptenone); diketones and hydroxyketones such as diacetyl, 2,3-pentanedione, maltol, ethyl maltol, cyclotene, and 2,5-dimethyl-4-hydroxy-3(2H)-furanone; terpene ketones such as carvone, menthone, and nootkatone; ketones derived from terpene degradation products such as α-ionone, β-ionone, and β-damascenone; and aromatic ketones such as raspberry ketone.

[0064] Examples of furan or ether compounds include furfuryl alcohol, furfural, rose oxide, linalool oxide, menthofuran, theaspirane, estragole, eugenol, and 1,8-cineole.

[0065] Examples of the ester compound include aliphatic esters such as ethyl acetate, isoamyl acetate, octyl acetate, ethyl butyrate, ethyl isobutyrate, isoamyl butyrate, ethyl 2-methylbutyrate, ethyl isovalerate, 2-methylbutyl isobutyrate, ethyl hexanoate, allyl hexanoate, ethyl heptanoate, ethyl caprylate, isoamyl isovalerate, and ethyl nonanoate; terpene alcohol esters such as linalyl acetate, geranyl acetate, lavandulyl acetate, terpinyl acetate, and neryl acetate; and aromatic esters such as benzyl acetate, methyl salicylate, methyl cinnamate, cinnamyl propionate, ethyl benzoate, cinnamyl isovalerate, and ethyl 3-methyl-2-phenylglycidate.

[0066] Examples of the lactone compound include saturated lactones such as γ-decalactone, γ-dodecalactone, δ-decalactone, and δ-dodecalactone, and unsaturated lactones such as 7-decen-4-olide and 2-decen-5-olide.

[0067] Acid compounds include saturated and unsaturated fatty acids such as acetic acid, butyric acid, isovaleric acid, caproic acid, octanoic acid, stearic acid, oleic acid, linoleic acid, and linolenic acid.

[0068] Examples of the nitrogen-containing compound include indole, skatole, pyridine, alkyl-substituted pyrazine, methyl anthranilate, and trimethylpyrazine.

[0069] Examples of sulfur-containing compounds include methanethiol, dimethyl sulfide, dimethyl disulfide, allyl isothiocyanate, 3-methyl-2-butene-1-thiol, 3-methyl-2-butanethiol, 3-methyl-1-butanethiol, 2-methyl-1-butanethiol, 3-mercaptohexanol, 4-mercapto-4-methyl-2-pentanone, 3-mercaptohexyl acetate, p-mentha-8-thiol-3-one, and furfuryl mercaptan.

[0070] Natural essential oils include sweet orange, bitter orange, petitgrain, lemon, bergamot, mandarin, neroli, peppermint, spearmint, lavender, chamomile, rosemary, eucalyptus, sage, basil, rose, hyacinth, lilac, geranium, jasmine, ylang-ylang, anise, clove, ginger, nutmeg, cardamom, cedar, cypress, vetiver, patchouli, and labdanum.

[0071] Natural fragrances include jasmine absolute, hyacinth absolute, rose absolute, tuberose absolute, vanilla absolute, galbanum resinoid, and the like.

[0072] Examples of various animal and plant extracts include herb or spice extracts, coffee, green tea, black tea, or oolong tea extracts, milk or dairy products, and various enzymatic decomposition products thereof using lipase and / or protease.

[0073] Furthermore, in addition to the above, other additives described in the section (Examples of Use) below can also be used as appropriate. The above other flavoring ingredients and other additives may be used alone or in combination of two or more.

[0074] The fragrance composition according to the present embodiment can be prepared by adding the compound of the present invention to an appropriate solvent or dispersion medium by a known method.

[0075] The fragrance composition according to this embodiment is preferably in the form of a solution in which the compound of the present invention and other components are dissolved in a water-soluble or oil-soluble solvent, an emulsion preparation, a powder preparation, or other solid preparation (such as solid fat).

[0076] Examples of water-soluble solvents include ethanol, methanol, acetone, tetrahydrofuran, acetonitrile, 2-propanol, methyl ethyl ketone, glycerin, propylene glycol, and dipropylene glycol. Among these, ethanol and glycerin are particularly preferred from the viewpoint of use in foods and beverages. Examples of oil-soluble solvents include vegetable oils and fats, animal oils and fats, refined oils and fats (e.g., processed oils and fats such as medium-chain fatty acid triglycerides, and short-chain fatty acid triglycerides such as triacetin and tripropionin), various essential oils, and triethyl citrate.

[0077] In addition, to prepare an emulsion preparation, the present compound can be emulsified with a water-soluble solvent and an emulsifier.The emulsification method of the present compound is not particularly limited, and can be carried out by using various emulsifiers that have been conventionally used in foods and beverages, such as fatty acid monoglycerides, fatty acid diglycerides, fatty acid triglycerides, propylene glycol fatty acid esters, sucrose fatty acid esters, polyglycerin fatty acid esters, lecithin, modified starch, sorbitan fatty acid esters, Quillaja extract, gum arabic, tragacanth gum, guar gum, karaya gum, xanthan gum, pectin, alginic acid and its salts, carrageenan, gelatin, casein Quillaja saponin, sodium caseinate, etc., and emulsifying the same using a homomixer, colloid mill, rotating disk homogenizer, high-pressure homogenizer, etc., to obtain an emulsion with excellent stability. The amount of these emulsifiers used is not strictly limited and can vary over a wide range depending on the type of emulsifier used, but is usually within the range of about 0.01 to about 100 parts by mass, preferably about 0.1 to about 50 parts by mass, per part by mass of the compound of the present invention. Furthermore, to stabilize the emulsion, the aqueous solvent solution may contain, in addition to water, one or a mixture of two or more polyhydric alcohols such as glycerin, propylene glycol, sorbitol, maltitol, sucrose, glucose, trehalose, sugar solution, and reduced starch syrup.

[0078] The emulsion thus obtained can be dried, if desired, to form a powder formulation. During powdering, sugars such as gum arabic, trehalose, dextrin, sugar, lactose, glucose, starch syrup, and reduced starch syrup can be added as needed. The amounts of these can be selected appropriately depending on the desired properties of the powder formulation.

[0079] The fragrance composition according to the present embodiment may further contain, if necessary, components commonly used in fragrance compositions, such as solvents such as water and ethanol, and fragrance retention agents such as ethylene glycol, propylene glycol, dipropylene glycol, glycerin, hexyl glycol, benzyl benzoate, triethyl citrate, diethyl phthalate, Hercolin, medium-chain fatty acid triglycerides, and medium-chain fatty acid diglycerides.

[0080] <Consumer goods and methods for improving the flavor of consumer goods> The present flavoring composition, i.e., a flavoring composition containing the present compound in a specific cis-trans isomer ratio (including cases where it is configured as a fragrance composition for cosmetics or a fragrance composition for food or beverage; the same applies hereinafter), may be added to any article such as various consumer goods. That is, as another embodiment of the present invention, there is provided a consumer good to which the above-mentioned flavoring composition has been added. The above-mentioned flavoring composition is preferably used in consumer goods such as cosmetics, foods and beverages, and is particularly preferably used in cosmetics.

[0081] In yet another embodiment of the present invention, there is provided a method for improving the flavor of consumer goods, which comprises adding the above-mentioned flavor-imparting composition to the consumer goods. The method for adding the above-mentioned flavor-imparting composition is not particularly limited, and the flavor-imparting composition can be added using techniques known to those skilled in the art.

[0082] Examples of cosmetics as consumer goods include, but are not limited to, perfumes such as eau de cologne, eau de toilette, eau de parfum, and parfum; hair care products such as shampoo, conditioner, and hair styling products (hair cream, pomade, etc.); cosmetics such as foundation, lipstick, lip balm, lip gloss, lotion, cosmetic emulsion, cosmetic cream, cosmetic gel, serum, and pack; deodorant products such as antiperspirant spray, deodorant sheet, deodorant cream, and deodorant stick; inorganic salt-based, refreshing, and carbon dioxide-based products; Examples include skin care, enzyme, and herbal bath additives; tanning cosmetics such as suntan products and sunscreen products; cleaning agents such as face soap and facial cleansing cream, body soap, laundry soap, laundry detergent, disinfectant detergent, deodorizing detergent, fabric softener, kitchen detergent, cleaning detergent, disinfectant, bleach, toothpaste, and mouthwash; health and hygiene products or quasi-drugs such as dry or wet tissues, toilet paper, masks, bandages, adhesive plasters, and compresses; and air fresheners and deodorizers for use in rooms and cars.

[0083] The cosmetic product according to the present embodiment can be manufactured using methods known to those skilled in the art. The form (form) of the cosmetic product is not particularly limited. For example, it can be in various forms such as liquid, emulsion, cream, paste, solid, and multi-layered. It can also be in the form of a sheet, spray, or mousse.

[0084] The cosmetic product according to the present embodiment may contain other additives so that the flavoring composition of the present invention is dispersed uniformly at an appropriate concentration, as long as the additives do not impair the desired fragrance.

[0085] The other additives are not particularly limited and known additives can be used, for example, hydrocarbons such as squalane, petrolatum, and microcrystalline wax; esters such as jojoba oil, carnauba wax, octyldodecyl oleate, phenylethyl acetate, phenylethyl butyrate, phenylethyl formate, phenylethyl phenylacetate, phenylethyl isobutyrate, benzyl benzoate, phenylethyl propionate, and phenylpropyl acetate; phenylacetaldehyde, benzaldehyde, cinnamic aldehyde, Aldehydes such as hexyl cinnamic aldehyde; triglycerides such as olive oil, beef tallow, and coconut oil; fatty acids such as stearic acid, oleic acid, and ricinoleic acid; alcohols such as linalool, citronellol, bacdanol, dihydromyrcenol, dihydrolinalool, geraniol, nerol, sandalole, Santalex, terpineol, tetrahydrolinalool, benzyl alcohol, phenylethyl alcohol, phenylethyldimethylcarbinol, and hydroxycitronellal; Examples of the surfactants include higher alcohols such as oleyl alcohol, stearyl alcohol, and octyldodecanol; polyhydric alcohols such as ethylene glycol, propylene glycol, glycerin, and 1,3-butanediol; nitrogen- and / or sulfur-containing compounds such as indole, 5-methyl-3-heptanone oxime, limonenethiol, 1-p-menthene-8-thiol, butyl anthranilate, cis-3-hexenyl anthranilate, phenylethyl anthranilate, cinnamyl anthranilate, dimethyl sulfide, and 8-mercaptomenthone; anionic surfactants such as sulfosuccinate esters and polyoxyethylene alkyl sulfate sodium; amphoteric surfactants such as alkyl betaine salts; cationic surfactants such as dialkylammonium salts; nonionic surfactants such as sorbitan fatty acid esters, fatty acid monoglycerides, their polyoxyethylene adducts, polyoxyethylene alkyl ethers, and polyoxyethylene fatty acid esters; thickeners and gelling agents; antioxidants; UV absorbers; colorants; preservatives; and powders.

[0086] In addition to these, other fragrance components listed in the above section (Fragrance composition) can also be used as other additives in cosmetics. The other additives may be used alone or in combination of two or more.

[0087] The fragrance tone of the cosmetic product according to the present embodiment is not particularly limited and may be any fragrance tone that can be imparted by the flavor-imparting composition of the present invention, including, for example, citrus, floral, fougere, fruity, green, woody, moss, tropical flower, lily of the valley (also known as lily of the valley), oriental, and chypre. The fragrance tone of the cosmetic product according to the present embodiment is more preferably used in cosmetics that exhibit a lily of the valley or citrus scent. Specific examples of plants that belong to the lily of the valley or citrus tone include, but are not limited to, lemon, orange, grapefruit, lime, yuzu, kabosu, rose, geranium, jasmine, lily of the valley, hyacinth, lilac, plumeria, pineapple, mango, and peach.

[0088] The amount of the present flavoring composition added to the cosmetic product according to this embodiment can be determined arbitrarily depending on the fragrance of the cosmetic product, the degree of the desired effect, etc. However, as an example, the present flavoring composition can be added so that the concentration of the present compound is in the range of, for example, 0.001% to 10%, preferably 0.01% to 0.1%, based on the total mass of the cosmetic product.

[0089] By adding the flavor-imparting composition of the present invention to the cosmetic product according to this embodiment, it is possible to obtain a fragrance effect that includes at least one of the following effects: improving the lingering, persistence, and / or diffusibility of the fragrance of the cosmetic product; imparting a floral and / or green tone; imparting a fresh, moist feeling; imparting transparency; imparting volume; and masking the unpleasant odor of the cosmetic material itself.

[0090] Examples of food and beverages as consumer goods include, but are not limited to, various citrus flavors such as lemon, orange, grapefruit, lime, mandarin, mandarin orange, kabosu, sudachi, hassaku, iyokan, yuzu, shikuwasa, and kumquat; various fruit flavors such as strawberry, blueberry, raspberry, apple, cherry, plum, apricot, peach, pineapple, banana, melon, mango, papaya, kiwi, pear, grape, muscat, and Kyoho grape; dairy flavors such as milk, yogurt, and butter; vanilla flavor; various tea flavors such as green tea, black tea, oolong tea, and herbal tea; coffee flavor; cola flavor; cacao flavor; cocoa flavor; various mint flavors such as spearmint and peppermint; cinnamon, chamomile, cardamom, caraway, cumin, cloves, pepper, coriander, Japanese pepper, shiso, ginger, star anise, and Thai Various spice or herb flavors such as ginger, chili pepper, nutmeg, basil, marjoram, rosemary, laurel, garlic, and wasabi; various nut flavors such as almond, cashew nut, and walnut; various alcohol flavors such as wine, brandy, whiskey, rum, gin, liqueur, sake, shochu, and beer; vegetable flavors such as onion, celery, carrot, tomato, and cucumber; various meat flavors such as chicken, duck, pork, beef, lamb, and horse meat. Flavors include foods and beverages having one or more of the following flavors: various seafood and seaweed flavors, such as red fish such as tuna, white fish such as mackerel, sea bream, salmon, and horse mackerel, freshwater fish such as sweetfish, trout, and carp, shellfish such as turban shells, clams, short-necked clams, and shijimi clams, various crustaceans such as shrimp and crab, and various seaweeds such as wakame seaweed and kelp; various grain flavors, such as rice, barley, wheat, and malt; and various oil and fat flavors, such as beef tallow, chicken oil, and lard, and various fish oils. The flavors are particularly suitable for citrus, black tea, and muscat flavored foods and beverages.The flavor of the food or beverage may be one of the above flavors, or two or more flavors, and the multiple flavors may be similar or different. For example, an example of the former is a fruit flavor that gives the impression of multiple fruit flavors such as banana, peach, and apple (so-called mixed fruit flavor), and an example of the latter is a citrus flavor such as lemon and a milk flavor (such as a citrus-flavored lactic acid bacteria drink), or a mint flavor, citrus flavor, and cola flavor (such as a mint or lemon-flavored cola drink).

[0091] More specific examples of food and drink include rice crackers, arare (rice crackers), okoshi (rice crackers), mochi (rice cakes), manju (buns), uriwara (sweet rice cakes), bean paste, yokan (sweet bean jelly), mizuyokan (sweet bean jelly), kingyoku (golden balls), jelly, castella (sponge cakes), candy, biscuits, crackers, potato chips, cookies, pies, puddings, butter cream, custard cream, cream puffs, waffles, sponge cakes, donuts, chocolate, chewing gum, caramel, candy, pastes such as peanut paste, and other confectioneries; bread, udon, ramen, Chinese noodles, sushi, gomoku-meshi (rice with mixed ingredients), fried rice, pilaf, gyoza wrappers, shumai wrappers, and other confectioneries. Breads such as miyaki (grilled stew), takoyaki (octopus balls), noodles, rice dishes; pickles such as pickled plums, pickled plums, fukujinzuke (pickled vegetables), bettarazuke (pickled vegetables), senmaizuke (pickled vegetables), pickled radishes, misozuke (pickled vegetables), takuanzuke (pickled radishes), and the bases for these pickles; fish such as mackerel, sardines, saury, salmon, tuna, bonito, whale, flounder, sand lance, and sweetfish; squid such as pacific flying squid, spear squid, crested squid, and firefly squid; octopus such as common octopus and Japanese octopus; shrimp such as kuruma prawns, botan shrimp, spiny lobster, and black tiger prawns; crabs such as king crab, snow crab, blue crab, and hairy crab; clams, hard clams, scallops, crabs, and crabs. Seafood such as yellowtail, mussels, and other shellfish; canned food, boiled fish, tsukudani (simmered fish), surimi (surimi), fish paste products (chikuwa, kamaboko, fried kamaboko, crab leg kamaboko, etc.), fried foods, tempura, and other processed seafood foods; livestock meat such as chicken, pork, beef, lamb, and horse meat; curry, stew, beef stew, hayashi rice sauce, meat sauce, mapo tofu, hamburger steak, gyoza, kamameshi ingredients, soups (corn soup, tomato soup, consommé soup, etc.), meatballs, braised pork, canned meat, and other processed foods and drinks; table salt, seasoning salt, soy sauce, powdered soy sauce, miso, powdered miso, moromi, and hisio. Seasonings such as furikake, ochazuke seasonings, margarine, mayonnaise, dressings, vinegar, sanbaizu vinegar, powdered sushi vinegar, Chinese seasonings, tempura sauce, noodle soup (kelp stock or bonito stock, etc.), sauces (medium-thick sauce, tomato sauce, etc.), ketchup, yakiniku sauce, curry roux, stew seasonings, soup seasonings, dashi seasonings (kelp stock or bonito stock, etc.), compound seasonings, hon mirin, new mirin (nikiri mirin), mixed powders such as fried chicken powder and takoyaki powder, and animal or plant-based dashi-flavored foods and beverages to which these seasonings have been added; dairy products such as cheese, yogurt, and butter;Various yeasts such as beer yeast and baker's yeast, and lactic acid bacteria and other microbial fermented products; simmered vegetables, Chikuzenni, oden, hotpots, and other simmered dishes; take-out bento ingredients and side dishes; fruit juice drinks and soft drinks containing fruit juice, such as apples, grapes, and citrus fruits (grapefruit, oranges, lemons, etc.), and fruit pulp drinks and fruit drinks containing whole fruit; vegetable-containing foods and beverages such as tomatoes, bell peppers, celery, gourds, bitter melon, carrots, potatoes, asparagus, bracken, and fern, as well as vegetable drinks and vegetable soups containing these vegetables; coffee, cocoa, green tea, black tea, oolong tea, soft drinks, cola drinks, carbonated drinks (ciders with various flavors, including citrus flavors), and lactic acid bacteria drinks; herbal medicines and herbs Examples of such beverages include beverages containing alcohol; functional beverages such as cola drinks, fruit juice drinks, dairy drinks, beer-flavored beverages including non-alcoholic beer and so-called "third beer," sports drinks, honey drinks, vitamin supplement drinks, mineral supplement drinks, energy drinks, nutritious drinks, and lactic acid bacteria drinks; non-alcoholic beverages such as alcohol-flavored beverages with various alcoholic flavors (beer, plum wine, chuhai, etc.); wine, shochu, awamori, sake, beer, chuhai, cocktail drinks, happoshu, fruit wine, condiment wine, so-called "third beer," and other brewed alcoholic beverages (sparkling) or liqueurs (sparkling), or alcoholic beverages containing these;

[0092] The amount of the present flavor-imparting composition added to the food or drink according to this embodiment can be determined arbitrarily depending on the flavor of the food or drink, the degree of the desired effect, etc. However, as an example, the present flavor-imparting composition can be added so that the concentration of the present compound is in the range of, for example, 10 ppt to 10 ppm, preferably 0.1 ppb to 10 ppb, based on the total mass of the food or drink.

[0093] By adding the flavor-imparting composition of the present invention to the food and beverage products of this embodiment, it is possible to obtain a flavoring effect that includes at least one of the following: enhancing flavor, imparting bitterness such as a peel-like flavor, imparting an oily flavor like peel wax, imparting volume, and imparting a citrus flavor.

[0094] <Method for improving the flavor of a flavor-imparting composition> In yet another embodiment of the present invention, there is provided a method for improving the flavor of a flavor-imparting composition, comprising adding the present flavor-imparting composition to another flavor-imparting composition. The method for adding the present flavor-imparting composition is not particularly limited, and the composition can be added using techniques known to those skilled in the art.

[0095] As will be shown in the Examples below, by adding the present flavor-imparting composition to another flavor-imparting composition, the flavor of the other flavor-imparting composition can be improved. More specifically, by adding the present flavor-imparting composition to another flavor-imparting composition, it is possible to impart a fragrance mainly consisting of floral and green notes, and to obtain a flavor-imparting composition that has a natural scent, excellent diffusibility, and lingering aroma.

[0096] In the method for improving the flavor of a flavor-imparting composition according to this embodiment, when the flavor-imparting composition of the present invention is added to another flavor-imparting composition, the concentration of the compound of the present invention in the other flavor-imparting composition can be determined arbitrarily depending on the aroma characteristics of the other flavor-imparting composition and / or the target to which the other flavor-imparting composition is to be added. The specific concentration is as described above in the section "Flavor-imparting composition."

[0097] In the method for improving the flavor of a flavor-imparting composition according to the present embodiment, the method for adding the present flavor-imparting composition to another flavor-imparting composition is not particularly limited, and any method known to those skilled in the art may be used. Furthermore, the timing for adding the present flavor-imparting composition to another flavor-imparting composition is not particularly limited. [Example]

[0098] The present invention will be explained in more detail below with reference to examples, although the present invention is not limited to these examples.

[0099] [Example 1] Preparation of the Compound The compound of the present invention was obtained according to the method described below. The isomer ratio of the compound of the present invention was determined by measuring the retention time of gas chromatography (GC) and calculating the ratio of the peak areas. The GC conditions were as follows:

[0100] GC device: GC-2025 (manufactured by Shimadzu Corporation) Column: TC-1, 0.53 mm (ID) × 30 m (L), df = 1.50 μm (GL Sciences Inc.) Detector: Flame ionization detector (FID) Injection temperature: 300℃ Detector temperature: 300℃ Temperature increase conditions: 100°C → 300°C (20°C increase per minute) Linear speed: 60.0cm / S

[0101] [Example 1-1] Synthesis of the (4E,7E) form of the present compound

[0102] [ka]

[0103] (1) Synthesis of Compound 3

[0104] [ka]

[0105] A 1 L three-neck flask was charged with NaH (55% in mineral oil, 9.29 g, 1.5 eq.) and THF (300 mL), followed by the addition of triethyl phosphonoacetate (69.5 g, 310 mmol, 1.2 eq.) over 30 minutes under ice-water cooling. The mixture was then stirred at room temperature for 1 hour. The mixture was again cooled with ice-water, and tiglic aldehyde (2, 21.74 g, 258 mmol) was added, followed by stirring at room temperature for 1 hour. Tap water (300 mL) was added to the reaction mixture, which was then extracted with hexane (300 mL). The organic phase was washed sequentially with tap water / methanol (300 mL / 300 mL) and saturated brine (300 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue (41.36 g) was purified by silica gel column chromatography (hexane / ethyl acetate=40:1→20:1) to give the desired ester 3 as a slightly yellow oily substance (22.72 g, 147 mmol, 57%).

[0106] (2) Synthesis of Compound 4

[0107] [ka]

[0108] A 1-L three-neck flask was charged with diisopropylamine (18.62 g, 184 mmol, 1.25 eq.) and THF (300 mL), followed by ice-methanol cooling. n-BuLi (1.57 M in hexane, 117 mL, 184 mmol, 1.25 eq.) was added over 30 min. The mixture was stirred at 0 °C for 10 min, then cooled with dry ice and acetone. A solution of ester 3 (22.7 g, 147 mmol) in THF (20 mL) was added dropwise over 30 min and stirred at the same temperature for 1 h. 50% acetic acid (100 mL) was added to the reaction mixture, which was then warmed to room temperature. Tap water (200 mL) was added, and the mixture was extracted with hexane (300 mL). The organic phase was washed sequentially with saturated sodium bicarbonate water (300 mL), tap water (300 mL), and saturated brine (300 mL). The mixture was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue (22.55 g) was purified by silica gel column chromatography (hexane / ethyl acetate=50:1) to give the desired ester 4 as a slightly yellow oily substance (13.75 g, 86.1 mmol, 59%).

[0109] (3) Synthesis of Compound 5

[0110] [ka]

[0111] A 1 L four-neck flask was charged with LiAlH4 (6.41 g, 169 mmol, 2 eq.) and diethyl ether (200 mL), followed by the dropwise addition of a diethyl ether (20 mL) solution of ester 4 (13.75 g, 86.1 mmol) over 1 h under ice-methanol cooling. The mixture was then stirred at room temperature for 30 min. The mixture was again cooled under ice-methanol cooling, and saturated Rochelle salt solution (500 mL) was added dropwise. The mixture was then stirred overnight. The organic phase was separated, washed with tap water (200 mL) and saturated brine (200 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue (8.81 g) was purified by silica gel column chromatography (hexane / ethyl acetate = 5:1) to give the desired alcohol 5 as a pale yellow oil (6.90 g, 61.5 mmol, 71%).

[0112] (4) Synthesis of Compound 6

[0113] [ka]

[0114] A solution of alcohol 5 (4.49 g, 40 mmol) in CHCl (80 mL) was added to a 200 mL two-neck flask and cooled with ice water. 2,2,6,6-Tetramethylpiperidine 1-oxyl (TEMPO, 187.5 mg, 1.2 mmol, 3 mol%) and PhI(OAc) (19.33 g, 60 mmol, 1.5 eq.) were added sequentially and stirred at the same temperature for 2 hours and then at 15 °C for 3 hours. Additional TEMPO (187.5 mg, 1.2 mmol, 3 mol%) was added and stirred at 15 °C for 2 hours. Saturated aqueous sodium thiosulfate (100 mL) was added to the reaction mixture, which was then warmed to room temperature and extracted with ether (300 mL). The organic phase was washed sequentially with tap water (300 mL), saturated aqueous sodium bicarbonate (300 mL), and saturated brine (300 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue (17.92 g) was used in the subsequent reaction without purification.

[0115] (5) Synthesis of Compound 7

[0116] [ka]

[0117] A 200 mL two-neck flask was charged with isopropenylmagnesium bromide (0.5 M in THF, 92 mL, 46 mmol, 1.15 eq.) and cooled with ice water. A solution of the crude product from the previous step (17.92 g) in THF (20 mL) was added dropwise over 5 minutes, followed by stirring at the same temperature for 30 minutes and then at room temperature for 2 days. A saturated aqueous solution of ammonium chloride (100 mL) was added dropwise, followed by tap water (50 mL) and extraction with ether (100 mL). The organic phase was separated, washed with tap water (100 mL), saturated aqueous sodium bicarbonate (100 mL), and saturated brine (100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane / ethyl acetate=50:1 to 10:1) to give the target alcohol 7 as a slightly yellow oily substance (4.10 g, 26.9 mmol, 67%).

[0118] (6) Synthesis of Compound 8

[0119] [ka]

[0120] Alcohol 7 (4.10 g, 26.9 mmol), ethyl vinyl ether (EVE, 38.8 g, 538 mmol, 20 eq.), and mercury acetate (1.71 g, 5.38 mmol, 0.2 eq.) were sequentially added to a 200 mL two-neck flask and stirred at room temperature for 2 days. Tap water (50 mL) was added to the reaction mixture, and after extraction with ether (100 mL), the organic phase was washed with saturated sodium bicarbonate water (50 mL) and saturated brine (50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure.

[0121] The residue (3.40 g) was added to a 100 mL recovery flask, and toluene (PhMe, 30 mL) was added. The mixture was heated under reflux for 6 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The residue (3.50 g) was purified by silica gel column chromatography (hexane / ethyl acetate = 50:1 to 10:1) and subjected to Kugelrohr distillation (135 °C / 0.1 kPa) to obtain the desired aldehyde 1 as a colorless oil (1.15 g, 6.45 mmol, 24%).

[0122] [Example 1-2] Synthesis of the (4E,7Z) form of the present compound

[0123] [ka]

[0124] (1) Synthesis of Compound 22

[0125] [ka]

[0126] A 300 mL three-neck flask was charged with phosphonium salt 14 (22.7 g, 46.8 mmol) and THF (dried over molecular sieves, 500 mL). The mixture was placed in a dry ice acetone bath under a nitrogen atmosphere, and n-BuLi (1.57 M in hexane, 30.6 mL, 48 mmol) was added dropwise. After stirring at the same temperature for 30 min, ketone 16 (7.52 g, 40.0 mmol) was added dropwise. After stirring at the same temperature for 30 min, the mixture was gradually warmed to room temperature and stirred overnight. Tap water (1 L) was added to the reaction mixture, and the mixture was extracted with ether (300 mL). The organic phase was washed with saturated brine (500 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane / EtOAc=20:1) to obtain the desired alkene 22 as a colorless oil (10.2 g, 32.6 mmol, 81%).

[0127] (2) Synthesis of Compound 23

[0128] [ka]

[0129] A 200 mL two-neck flask was charged with tetra-n-butylammonium fluoride (TBAF, 1 M in THF, 58 mL, 58 mmol). Under a nitrogen atmosphere and ice-water cooling, a solution of silyl ether 22 (12.2 g, 38.7 mmol) in THF (5 mL) was added dropwise and stirred at room temperature for 2 h. The reaction mixture was poured into saturated aqueous ammonium chloride (200 mL) and extracted with ether (200 mL). The organic phase was washed with tap water (100 mL) and saturated brine (100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane / EtOAc = 2:1) to give the desired alcohol 23 as a colorless oil (5.6 g, 28 mmol, 72%).

[0130] (3) Synthesis of Compound 24 and Compound 25

[0131] [ka]

[0132] Manganese dioxide (36.5 g, 420 mmol), methylene chloride (250 mL), and alcohol 23 (5.6 g, 28 mmol) were added sequentially to a 500 mL recovery flask and stirred at room temperature for 3 hours. Manganese dioxide (12.2 g, 140 mmol) was then added and the mixture was stirred for 3 hours. The reaction mixture was then filtered through Celite. The filtrate was concentrated under reduced pressure, and THF was added to the residue, which was then concentrated under reduced pressure again to give a residue containing aldehyde 24 (5.39 g).

[0133] Methyltriphenylphosphonium bromide (12.0 g, 33.6 mmol) and THF (dried over molecular sieves, 120 mL) were added to a 300 mL two-neck flask. Under a nitrogen atmosphere, n-BuLi (21.3 mL, 33.6 mmol) was added dropwise in a dry ice acetone bath. After stirring at the same temperature for 30 min, a solution of the above residue (5.39 g) in THF (10 mL) was added dropwise over 30 min. The reaction mixture was gradually warmed to room temperature and stirred overnight. Tap water (200 mL) was added to the reaction mixture, followed by ether extraction (200 mL). The organic phase was washed with saturated brine (100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane / EtOAc = 20:1) to obtain the desired alkene 25 as a colorless oil (3.80 g, 19.4 mmol, 69%).

[0134] (4) Synthesis of Compound 26

[0135] [ka]

[0136] Ether 25 (3.70 g, 18.8 mmol), methanol (20 mL), and p-toluenesulfonic acid monohydrate (3.6 mg, 0.19 mmol) were added to a 100 mL recovery flask and stirred at room temperature for 2 h. Additional p-toluenesulfonic acid monohydrate (3.6 mg, 0.19 mmol) and methanol (20 mL) were added and stirred at room temperature for 4 h. Saturated aqueous sodium bicarbonate (100 mL) and tap water (200 mL) were added sequentially to the reaction mixture, followed by ether extraction (100 mL). The organic phase was washed with saturated brine (50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane / EtOAc = 3:1) to give the desired alcohol 26 as a colorless oil (1.86 g, 16.5 mmol, 88%).

[0137] (5) Synthesis of Compound 11 and Compound 21

[0138] [ka]

[0139] Alcohol 26 (1.86 g, 16.5 mmol), methylene chloride (100 mL), TEMPO (0.07 g, 0.5 mmol), and iodobenzene diacetate (7.97 g, 24.8 mmol) were sequentially added to a 200 mL two-neck flask under ice-water cooling and stirred for 3 h while maintaining the temperature below 15 °C. TEMPO (0.07 g, 0.5 mmol) was added to the reaction mixture and stirred for an additional 1 h. Saturated aqueous sodium bicarbonate (300 mL) was added to the reaction mixture, followed by extraction with ether (200 mL). The organic phase was washed sequentially with tap water (100 mL) and saturated brine (100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give a residue (6.41 g) containing aldehyde 11 as a pale yellow oil.

[0140] A 200 mL two-neck flask was charged with nitrogen and charged with isopropenylmagnesium bromide (0.5 M in THF, 87 mL, 43 mmol). A solution of the residue (6.41 g) in THF (20 mL) was added dropwise under ice-water cooling and stirred overnight at room temperature. After cooling with ice-water, saturated aqueous ammonium chloride (100 mL) was added dropwise, followed by tap water (300 mL) and extraction with ether (200 mL). The organic phase was washed with tap water (100 mL), saturated aqueous sodium bicarbonate (100 mL), and saturated brine (100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane / EtOAc = 20:1) to give the desired alcohol 21 as a colorless oil (0.93 g, 6.1 mmol, 37%).

[0141] (6) Synthesis of Compound 1

[0142] [ka]

[0143] Alcohol 21 (0.93 g, 6.1 mmol), ethyl vinyl ether (8.80 g, 122 mmol), and mercury acetate (0.39 g, 1.2 mmol) were added sequentially to a 30 mL recovery flask and stirred overnight at room temperature. The reaction mixture was heated to 40 °C and stirred for an additional 7 h. Mercury acetate (0.39 g, 1.2 mmol) was then added and stirred overnight at room temperature. Tap water (30 mL) was added to the reaction mixture, and the mixture was extracted with ether (20 mL). The organic phase was washed with saturated aqueous sodium bicarbonate (20 mL) and saturated brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane / EtOAc = 20:1) to obtain the residue as a colorless oil (0.69 g).

[0144] The resulting residue was added to a 30 mL recovery flask, and toluene (10 mL) was added. The mixture was heated under reflux and stirred intermittently for 10 h (2 days). The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane / EtOAc = 25:1) and vacuum distillation to give the desired aldehyde (4E,7Z)-1 as a colorless oil (0.36 g, 2.02 mmol, 33%).

[0145] [Examples 1-3] Synthesis of the (4Z,7E) form of the present compound

[0146] [ka]

[0147] (1) Synthesis of Compound 8

[0148] [ka]

[0149] To a 300 mL two-neck flask, alcohol 5 (8.97 g, 80 mmol), triethylamine (16.6 mL, 120 mmol, 1.5 eq.), and methylene chloride (150 mL) were sequentially added. Methanesulfonyl chloride (MSCl, 8.05 mL, 104 mmol, 1.3 eq.) was added under ice-water cooling and stirred at the same temperature for 1 h. Tap water (50 mL) was added to the reaction mixture to quench the reaction. After removing the aqueous phase, the organic phase was washed with saturated brine (50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure.

[0150] The residue was added to a 500 mL recovery flask, and acetone (300 mL) and sodium iodide (NaI, 24.0 g, 160 mmol) were added sequentially. The mixture was heated and reacted under reflux for 3 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Tap water (200 mL) was added to the residue, and the mixture was extracted with hexane (100 mL). The organic phase was washed sequentially with saturated sodium bicarbonate water (100 mL), tap water (100 mL), and saturated brine (100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure.

[0151] The residue (18.4 g) was added to a 300 mL recovery flask, and methyl cyanide (MeCN, 300 mL) and triphenylphosphine (PPh3, 29.4 g, 112 mmol) were added sequentially. The mixture was heated and allowed to react under reflux for 5 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Hexane was added to the residue and stirred. The organic phase was decanted and washed, leaving a viscous solid. This washing procedure was repeated three times, followed by concentration under reduced pressure and solidification. The resulting solid was washed twice with hexane in the same manner. The resulting solid was dried in vacuo to obtain the desired phosphonium salt 8 as a pale yellow solid (35.5 g, 73.4 mmol, 92%).

[0152] (2) Synthesis of Compound 9

[0153] [ka]

[0154] A 500 mL two-neck flask was charged with phosphonium salt 8 (29.1 g, 60 mmol) and THF (200 mL), cooled with dry ice and methanol, and n-BuLi (1.58 M in hexane, 36.7 mL, 58 mmol) was added dropwise. The mixture was then stirred at the same temperature for 1 h. Ethyl levulinate (8.65 g, 36.7 mmol, 58 mmol) was added to the reaction mixture and stirred overnight at room temperature. Tap water (300 mL) was added to the reaction mixture, which was then extracted with ether (200 mL). The organic phase was washed with tap water (300 mL) and saturated brine (300 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane / ethyl acetate = 50:1) to obtain the desired ester 9 as a pale yellow oil (10.55 g).

[0155] (3) Synthesis of Compound 10

[0156] [ka]

[0157] A 300 mL two-neck flask was charged with LiAlH (2.20 g, 58 mmol, 1 eq.) and EtO (100 mL), followed by an EtO (10 mL) solution of ester 9 (crude 10.55 g) under ice-water cooling. The mixture was stirred at the same temperature for 30 min. Deionized water (2.2 mL), 15% NaOH (2.2 mL), and deionized water (6.6 mL) were added dropwise to the reaction mixture, and the mixture was stirred for 30 min. The reaction mixture was filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane / ethyl acetate = 5:1) to give the desired alcohol 10 as a colorless oil (3.79 g, 21.0 mmol, 2 steps, 36%). The 4-position isomer mixture was also obtained as a colorless oil (4.21 g, 23.4 mmol).

[0158] (4) Synthesis of Compound 1

[0159] [ka]

[0160] Alcohol 10 (0.90 g, 5.0 mmol), CHCl (10 mL), and TEMPO (0.04 g, 0.25 mmol, 5 mol%) were sequentially added to a 50 mL two-neck flask. After cooling with ice water, PhI(OAc) (2.42 g, 7.5 mmol, 1.5 eq.) was added and stirred at the same temperature for 4 hours. Aqueous sodium thiosulfate (30 mL) was added to the reaction mixture, which was then extracted with ether (30 mL). The organic phase was washed with saturated aqueous sodium bicarbonate (30 mL) and saturated brine (30 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane / ethyl acetate = 20:1), and the residue (0.94 g) was subjected to Kugelrohr distillation (160 °C / 0.3 kPa) to obtain the desired aldehyde (4Z,7E)-1 as a colorless oil (0.48 g, 2.7 mmol, 54%).

[0161] [Examples 1-4] Synthesis of the (4Z,7Z) form of the present compound

[0162] [ka]

[0163] (1) Synthesis of Compound 27

[0164] [ka]

[0165] To a 500 mL two-neck flask, alcohol 26 (11.2 g, 100 mmol), triethylamine (20.8 mL, 150 mmol, 1.5 eq.), and CHCl (150 mL) were added sequentially. MsCl (10.1 mL, 130 mmol, 1.3 eq.) was added under ice-water cooling and the mixture was stirred at the same temperature for 1 h. The reaction mixture was quenched by adding tap water (50 mL). After removing the aqueous phase, the organic phase was washed with saturated brine (50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure.

[0166] The residue was added to a 500 mL recovery flask, and acetone (300 mL) and NaI (30.0 g, 200 mmol) were added sequentially. The mixture was heated and reacted under reflux for 5 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Tap water (200 mL) was added to the residue, and the mixture was extracted with hexane (100 mL). The organic phase was washed sequentially with saturated sodium bicarbonate water (100 mL), tap water (100 mL), and saturated brine (100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure.

[0167] The residue (23.1 g) was added to a 500 mL recovery flask, and MeCN (300 mL) and PPh3 (36.8 g, 140 mmol) were added sequentially. The mixture was heated and allowed to react under reflux for 6 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Hexane was added to the residue and stirred. The viscous solid was left behind, and the organic phase was decanted and washed. This washing procedure was repeated three times, followed by concentration under reduced pressure and solidification. The resulting solid was washed three times with hexane in the same manner. The resulting solid was dried in vacuo to give the desired phosphonium salt 27 as a pale yellow solid (41.8 g, 86.3 mmol, 86%).

[0168] (2) Synthesis of Compound 28

[0169] [ka]

[0170] A 500 mL two-neck flask was charged with the phosphonium salt 27 (41.8 g, 86.3 mmol) and THF (300 mL), cooled with dry ice and methanol, and n-BuLi (1.58 M in hexane, 54 mL, 85 mmol) was added dropwise. The mixture was then stirred at the same temperature for 0.5 h. Ethyl levulinate (12.2 g, 84.6 mmol) was added to the reaction mixture and stirred overnight at room temperature. Tap water (500 mL) was added to the reaction mixture, which was then extracted with ether (300 mL). The organic phase was washed with tap water (300 mL) and saturated brine (300 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane / ethyl acetate = 50:1) to give the desired ester 28 (13.8 g) as a pale yellow oil.

[0171] (3) Synthesis of Compound 29

[0172] [ka]

[0173] A 300 mL two-neck flask was charged with LiAlH4 (3.22 g, 85 mmol, 1 eq.) and diethyl ether (100 mL), followed by an ice-water-cooled solution of ester 28 (crude 13.8 g) in diethyl ether (30 mL) and stirring at the same temperature for 1 h. Deionized water (3.2 mL), 15% NaOH (3.2 mL), and deionized water (9.6 mL) were added dropwise to the reaction mixture, and the mixture was stirred for 2 h. The reaction mixture was filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane / ethyl acetate = 5:1) to give the desired alcohol 29 as a colorless oil (4.70 g, 26.1 mmol, 2 steps, 31%).

[0174] (4) Synthesis of Compound 1

[0175] [ka]

[0176] To a 200 mL two-neck flask, alcohol 29 (4.70 g, 26.1 mmol), CHCl (50 mL), and TEMPO (0.28 g, 1.79 mmol, 6.9 mol%) were sequentially added. After cooling with ice water, PhI(OAc) (12.6 g, 39.1 mmol, 1.5 eq.) was added and the mixture was stirred overnight at the same temperature. Aqueous sodium thiosulfate (100 mL) was added to the reaction mixture, which was then extracted with ether (100 mL). The organic phase was washed with saturated aqueous sodium bicarbonate (50 mL) and saturated brine (50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane / ethyl acetate = 20:1), and the residue (3.77 g) was subjected to Kugelrohr distillation (160 °C / 0.2 kPa) to obtain the desired aldehyde (4Z,7Z)-1 as a colorless oil (2.92 g, 16.4 mmol, 63%).

[0177] [Example 2] Preparation of the present flavoring composition The isomers of the present compound synthesized in Example 1 were mixed in the ratios shown in Tables 1 and 2 below to prepare present invention products 2-1 to 2-23 (corresponding to the present flavor-imparting compositions). In addition, a comparative product 2-1 was prepared by mixing the isomers in the ratios described in Patent Document 1.

[0178] [Table 1]

[0179] [Table 2]

[0180] [Example 3] Aroma evaluation of the present flavoring composition To evaluate the odor of Invention Products 2-1 to 2-23 and Comparative Product 2-1 prepared in Example 2, Invention Products 2-1 to 2-23 and Comparative Product 2-1 were each diluted with ethanol to prepare 0.1% ethanol solutions of Invention Products 3-1 to 3-23 and Comparative Product 3-1. The odor evaluation of Invention Products 3-1 to 3-23 and Comparative Product 3-1 was carried out by impregnating scent strips with Invention Products 3-1 to 3-23 and Comparative Product 3-1, respectively, and having 15 well-trained perfumers with over 10 years of experience comment on them. Representative comments from the 15 perfumers are shown in Tables 3 and 4.

[0181] [Table 3]

[0182] [Table 4]

[0183] As shown in Tables 3 and 4, it was found that the aroma characteristics of the flavoring composition of the present invention differed greatly depending on the composition ratio of each isomer of the present compound contained as an active ingredient.

[0184] [Example 4] Addition to a fragrance composition A lily of the valley-like basic blend fragrance composition (Control Product 4) was prepared as shown in Table 5 below.

[0185] [Table 5]

[0186] Then, to the lily of the valley-like basic blend fragrance composition, the present invention products 2-1 to 2-23 obtained in Example 2 were added at the concentrations shown in Tables 6 to 9 below, respectively, to prepare fragrance compositions of the present invention products 4-1 to 4-174 (corresponding to the present flavor-imparting compositions as fragrance compositions for cosmetics).

[0187] The resulting fragrance compositions of Invention Products 4-1 to 4-174 were then subjected to a sensory evaluation by 15 well-trained perfumers (with 10 years or more of experience). The sensory evaluation was carried out by impregnating scent strips with Invention Products 4-1 to 4-174, asking the perfumers to comment on the difference in scent compared to Control Product 4, and averaging the scores given by the perfumers for the natural feeling (defined below) compared to Control Product 4 according to the following evaluation criteria.

[0188] (Evaluation criteria for naturalness) 5 points: The realistic lily of the valley scent was significantly enhanced compared to control product 4. 4 points: The realistic lily of the valley scent was somewhat enhanced compared to control product 4. 3 points: The realistic lily of the valley scent was slightly enhanced compared to control product 4. 2 points: The realistic lily of the valley scent was slightly enhanced compared to control product 4. 1 point: Equivalent to control product 4

[0189] The results of the sensory evaluation of the fragrance compositions of the present inventions 4-1 to 4-174 are shown in Tables 6 to 9 below.

[0190] [Table 6]

[0191] [Table 7]

[0192] [Table 8]

[0193] [Table 9]

[0194] Thus, it was confirmed that the fragrance compositions of the present invention, Products 4-1 to 4-174, all impart a distinctive fragrance with a realistic lily of the valley-like aroma. Furthermore, it was confirmed that, among the flavor-imparting compositions of the present invention, those with a high ratio of the (4E,7Z) isomer among the various isomers ((4E,7E) isomer / (4E,7Z) isomer = 60 / 40 or less) exhibit a high aroma-improving effect at low concentrations (0.005 to 0.5%) (specifically, Products 4-47 to 4-51, 4-56 to 4-60, 4-65 to 4-69, 4-74 to 4-78, 4-83 to 4-87, 4-92 to 4-96, and 4-101 to 4-105).

[0195] [Example 5] Addition to cosmetics Present invention products 2-1 to 2-23 obtained in Example 2 were added to commercially available citrus perfumes and ozone perfumes at a concentration of 0.05% based on the total mass of each perfume, to prepare present invention products 5-1 to 5-46. Eight well-trained perfumers with over 10 years of experience then conducted a sensory evaluation of present invention products 5-1 to 5-46. The sensory evaluation was conducted by asking the participants to comment on the differences in scent between present invention products 5-1 to 5-46 and each commercially available perfume without the addition of present invention products 2-1 to 2-23, which served as a control. The results of the sensory evaluation of present invention products 5-1 to 5-46 are shown in Tables 10 and 11 below.

[0196] [Table 10]

[0197] [Table 11]

[0198] As described above, it was confirmed that the addition of the flavor-imparting composition of the present invention to the cosmetics of the present invention, Products 5-1 to 5-46, enhanced various fragrances, imparted new fragrance characteristics, and imparted lingering fragrance properties.

[0199] [Example 6] Addition to food and drink Present Invention Products 2-1 to 2-23 obtained in Example 2 were added to commercially available apple juice beverages (30% juice) at concentrations of 10 ppt, 1 ppb, and 10 ppm, respectively, based on the total mass of the apple juice beverage, to prepare Present Invention Products 6-1 to 6-69. Then, eight well-trained panelists with over 10 years of experience conducted a sensory evaluation of Present Invention Products 6-1 to 6-69. The sensory evaluation was conducted by asking panelists to comment on the differences in flavor and aroma between Present Invention Products 6-1 to 6-69 and a commercially available apple juice beverage without Present Invention Products 2-1 to 2-23, which served as a control. The results of the sensory evaluation of Present Invention Products 6-1 to 6-69 are shown in Tables 12 and 13 below.

[0200] [Table 12]

[0201] [Table 13]

[0202] As described above, it was confirmed that the addition of the flavor-imparting composition of the present invention to the foods and beverages of the present invention 6-1 to 6-69 enhanced various flavors and imparted new flavor characteristics.

Claims

1. A flavoring composition comprising a compound represented by formula (1), the ratio of the (4E) isomer of the compound to the (4Z) isomer of the compound is (4E) isomer / (4Z) isomer=90 / 10 or more, The flavor-imparting composition, wherein, among the (4E) isomers of the compound, the ratio of the (4E,7E) isomers of the compound to the (4E,7Z) isomers of the compound is (4E,7E) isomers / (4E,7Z) isomers of the compound is 80 / 20 or more. 【Chemistry 1】

2. A flavoring composition comprising a compound represented by formula (1), the ratio of the (4E) isomer of the compound to the (4Z) isomer of the compound is (4E) isomer / (4Z) isomer=90 / 10 or more, The flavor-imparting composition, wherein, among the (4E) isomers of the compound, the ratio of the (4E,7E) isomers of the compound to the (4E,7Z) isomers of the compound is (4E,7E) isomers / (4E,7Z) isomers of the compound is greater than 60 / 40 but not greater than 70 / 30. 【Chemistry 2】

3. A flavoring composition comprising a compound represented by formula (1), the ratio of the (4E) isomer of the compound to the (4Z) isomer of the compound is (4E) isomer / (4Z) isomer=90 / 10 or more, The flavor-imparting composition, wherein, in the (4E) isomer of the compound, the ratio of the (4E,7E) isomer of the compound to the (4E,7Z) isomer of the compound is (4E,7E) isomer / (4E,7Z) isomer of the compound is 60 / 40 or less. 【Transformation 3】

4. A flavoring composition comprising a compound represented by formula (1), The flavor-imparting composition, wherein the ratio of the (4E) form of the compound to the (4Z) form of the compound is (4E) form / (4Z) form=10 / 90 or less. 【Chemistry 4】

5. The flavoring composition according to claim 4, The flavor-imparting composition, wherein, in the (4Z) form of the compound, the ratio of the (4Z,7E) form of the compound to the (4Z,7Z) form of the compound is (4Z,7E) form / (4Z,7Z) form=60 / 40 or more.

6. The flavoring composition according to claim 1 or 2, A flavor-imparting composition, wherein the concentration of the compound is in the range of 0.05% or more and 5% or less, based on the total mass of the flavor-imparting composition.

7. The flavoring composition according to claim 3, A flavor-imparting composition, wherein the concentration of the compound is in the range of 0.005% or more and 0.5% or less, based on the total mass of the flavor-imparting composition.

8. The flavoring composition according to claim 4 or 5, A flavor-imparting composition, wherein the concentration of the compound is in the range of 0.05% or more and 1% or less, based on the total mass of the flavor-imparting composition.

9. The flavor-imparting composition according to any one of claims 1 to 5, which is a fragrance composition for cosmetics.

10. The flavor-imparting composition according to any one of claims 1 to 5, which is a flavor composition for food or drink.

11. A method for improving the flavor of a flavor-imparting composition, comprising the step of adding the flavor-imparting composition according to any one of claims 1 to 5 to another flavor-imparting composition.

12. A consumer product comprising the flavoring composition according to any one of claims 1 to 5.

13. A method for improving the flavor of consumer goods, comprising the step of adding the flavor-imparting composition according to any one of claims 1 to 5 to the consumer goods.

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