Flavor composition

Abstract

An object of the present application is to provide a flavor composition and the like which effectively enhances a mouth-coating sensation. The present application relates to a flavor composition comprising at least two compounds selected from the group consisting of (A) a compound represented by general formula (I), (B) β-oxobicyclogermacrene, and (C) a compound represented by general formula (II): [in the formula, each symbol is as defined in the specification] [in the formula, each symbol is as defined in the specification].

Description

Technical Field

[0001] This invention relates to a flavoring composition, and more specifically, to a flavoring composition suitable for enhancing oral envelopment. Additionally, this invention relates to food products and methods of manufacturing them, and more specifically, to food products with enhanced oral envelopment and methods of manufacturing them. Furthermore, this invention relates to a method for enhancing oral envelopment. Background Technology

[0002] "Oral envelopment sensation" refers to the sensation of the mouth being covered by a thin film, oil, or oily solution or food when the mouth contains oil, a silky sensation, or a thick, oily sensation that extends throughout the mouth. It is believed that if there were a simple way to enhance oral envelopment sensation, such as using only a small amount of oil to provide the pleasant sensation felt when the mouth contains oil, it could help suppress excessive calorie intake and potentially prevent metabolic diseases such as obesity.

[0003] As a method to enhance the feeling of oral coverage, previous reports have included methods using hydrocolloids, low molecular weight compounds, polyphenols, or glycosides (Non-Patent Literature 1-5). However, there are problems such as the fact that the feeling enhanced by any of these methods is essentially different from the feeling of oral coverage when the mouth contains oils or other substances.

[0004] On the other hand, there are reports that adding methylcyclopentenolone, isovaleric acid, and caprylic acid to food can impart a stew-like flavor (Patent Document 1).

[0005] Existing technical documents

[0006] Patent documents

[0007] [Patent Document 1] International Publication No. 2014 / 142267

[0008] [Non-patent literature]

[0009] [Non-Patent Literature 1] Arocas et al., "Sensory properties determined by starch type in white sauces: effects of freeze / thaw and hydrocolloid addition." J Food Sci 2010, 75: S132-S140.

[0010] [Non-Patent Literature 2] Flett et al., “Perceived creaminess and viscosity of aggregated particles of casein micelles and κ-carrageenan” J Food Sci 2010, 75: S255-S261.

[0011] [Non-Patent Literature 3] Dawid et al., “Identification of sensory-active phytochemicals in asparagus (Asparagus officinalis L.)” J Agric Food Chem 2012, 60: 11877-11888.

[0012] [Non-Patent Literature 4] Schwarz et al., “Identification of novel orosensoryactive molecules in cured vanilla beans (Vanilla planifolia)” J Agric and Food Chem 2009, 57: 3729-3737.

[0013] [Non-Patent Literature 5] Scharbert et al., “Identification of the astringent taste compounds in black tea infusions by combining instrumental analysis and human bioresponse” J Agricand Food Chem 2004, 52: 3498-3508. Summary of the Invention

[0014] The problem that the invention aims to solve

[0015] The present invention was made in view of the above circumstances, and the problem to be solved is to provide a flavoring composition that can effectively enhance the oral enveloping sensation, a food that can effectively enhance the oral enveloping sensation and a method for manufacturing the same, and a method for effectively enhancing the oral enveloping sensation, etc.

[0016] Technical solutions to the problem

[0017] The inventors conducted in-depth research on the subject and found that by adding at least two compounds selected from the group consisting of (A) a compound represented by general formula (I) (e.g., methylcyclopentenolone), (B) β-caryophyllene oxide, and (C) a compound represented by general formula (II) (e.g., furfural), the oral coverage sensation can be enhanced. Through further research, the present invention was completed.

[0018] That is, the present invention is as follows.

[0019] [1] A fragrance composition comprising at least two compounds selected from the group consisting of (A) a compound represented by general formula (I), (B) β-caryophyllene oxide and (C) a compound represented by general formula (II):

[0020]

Chemistry 1

[0021]

[0022] [In the formula, ring A is a 5- or 6-membered saturated or unsaturated carbon ring, or a 5- or 6-membered saturated or unsaturated oxygen- or nitrogen-containing heterocycle.]

[0023] R 1 The radical can be an oxo group, a hydroxyl group, an alkoxy group with 1 to 4 carbon atoms, an acyloxy group with 1 to 4 carbon atoms, or a hydrocarbon group or hydrogen atom with 1 to 8 carbon atoms that may have substituents. 1 When the hydrocarbon group having 1 to 8 carbon atoms that can have substituents is a hydrocarbon group, the carbon atoms in the hydrocarbon group can bond with the carbon atoms of ring A to form a cross-linked structure or a saturated or unsaturated ring structure.

[0024] R 2 It consists of a hydrocarbon group, a hydroxyl group, or a hydrogen atom with 1 to 8 carbon atoms;

[0025] [n represents an integer from 1 to 3]

[0026]

Chemistry 2

[0027]

[0028] [In the formula, R] 3 It is an acyl group, hydroxyl group, pyrrole group, or acyloxy group with 1 to 6 carbon atoms;

[0029] Z is a single bond or an alkylene group having 1 to 6 carbon atoms;

[0030] R 4 For substituents;

[0031] m represents an integer from 0 to 3.

[0032] [2] According to the composition described in [1], the (A) is at least one compound selected from the group consisting of methylcyclopentenolone, γ-butyrolactone, 2-methyltetrahydrofuran-3-one, α-angelicolone, maltol, 3-methyl-1,2-cyclohexanedione, γ-dodecanolide, 5-dodecanolide, 4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one and D-camphor.

[0033] [3] According to the composition described in [1] or [2], the (C) is at least one compound selected from the group consisting of furfural, 2-acetylfuran, 2-acetyl-5-methylfuran, 3-acetyl-2,5-dimethylfuran, furfuryl alcohol, 1-furfurylpyrrole, furfuryl propionate, 5-methylfurfural and 5-(hydroxymethyl)furfural.

[0034] [4] In any one of the compositions according to [1] to [3], the at least two compounds selected from the group consisting of (A), (B) and (C) are any one of (i) to (xviii) below.

[0035] (i) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfural.

[0036] (ii) Select at least two compounds from the group consisting of (A) γ-butyrolactone, (B) β-caryophyllene oxide and (C) furfural.

[0037] (iii) At least two compounds selected from the group consisting of (A) 2-methyltetrahydrofuran-3-one, (B) β-caryophyllene oxide and (C) furfural.

[0038] (iv) Select at least two compounds from the group consisting of (A) α-angelicin, (B) β-caryophyllene oxide and (C) furfural.

[0039] (v) Select at least two compounds from the group consisting of (A) maltol, (B) β-caryophyllene oxide, and (C) furfural.

[0040] (vi) Select at least two compounds from the group consisting of (A) 3-methyl-1,2-cyclohexanedione, (B) β-caryophyllene oxide and (C) furfural.

[0041] (vii) Select at least two compounds from the group consisting of (A) γ-dodecanolide, (B) β-caryophyllene oxide and (C) furfural.

[0042] (viii) Select at least two compounds from the group consisting of (A) 5-dodecanolide, (B) β-caryophyllene oxide and (C) furfural.

[0043] (ix) At least two compounds selected from the group consisting of (A) 4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one, (B) β-caryophyllene oxide and (C) furfural.

[0044] (x) Select at least two compounds from the group consisting of (A) D-camphor, (B) β-caryophyllene oxide and (C) furfural.

[0045] (xi) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 2-acetylfuran.

[0046] (xii) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 2-acetyl-5-methylfuran.

[0047] (xiii) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 3-acetyl-2,5-dimethylfuran.

[0048] (xiv) Select at least two compounds from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfuryl alcohol.

[0049] (xv) Select at least two compounds from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 1-furfurylpyrrole.

[0050] (xvi) Select at least two compounds from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfuryl propionate.

[0051] (xvii) Select at least two compounds from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 5-methylfurfural.

[0052] (xviii) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 5-(hydroxymethyl)furfural.

[0053] [5] In any one of [1] to [4], the composition comprising at least two compounds selected from the group consisting of (A), (B) and (C) is at least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfural.

[0054] [6] The composition according to any one of [1] to [5] is used to enhance oral coverage.

[0055] [7] The composition according to any one of [1] to [6] contains (A), (B) and (C).

[0056] [8] In any one of the compositions according to [1] to [7], when the composition contains at least (A) and (B), the weight ratio (A:B) of the content of (A) to the content of (B) in the composition is A:B = 1:0.001 to 1000;

[0057] When the composition contains at least (A) and (C), the weight ratio (A:C) of the content of (A) to the content of (C) in the composition is A:C = 1:0.001 to 1000;

[0058] When the composition contains at least (B) and (C), the weight ratio (B:C) of the content of (B) to the content of (C) in the composition is B:C = 1:0.001 to 1000.

[0059] [9] The composition according to any one of [1] to [8], wherein the composition contains at least (A) and (B), and the weight ratio (A:B) of the content of (A) to the content of (B) in the composition is A:B = 1:0.001 to 1000.

[0060]

[10] The composition according to any one of [1] to [9] contains at least (A) and (C), and the weight ratio (A:C) of the content of (A) to the content of (C) in the composition is A:C = 1:0.001 to 1000.

[0061]

[11] The composition according to any one of [1] to

[10] , wherein the composition contains at least (B) and (C), and the weight ratio (B:C) of the content of (B) to the content of (C) in the composition is B:C = 1:0.001 to 1000.

[0062]

[12] When the composition according to any one of [1] to

[11] contains at least (A), the composition is added to the food in such a manner that the concentration a of (A) in the food is 0.05 to 5000 ppb by weight relative to the total weight of the food when it is consumed;

[0063] When the composition contains at least (B), the composition is added to the food in such a way that the concentration b of (B) in the food is 0.1 to 50,000 ppb by weight relative to the total weight of the food when it is consumed;

[0064] When the composition contains at least (C), the composition is added to the food in such a way that the concentration of (C) in the food, c, is 0.1 to 50,000 ppb by weight relative to the total weight of the food when consumed.

[0065]

[13] The composition according to any one of [1] to

[12] , wherein the composition contains at least (A) and is added to the food such that the concentration a of (A) in the food is 0.05 to 5000 ppb by weight relative to the total weight of the food when it is consumed.

[0066]

[14] The composition according to any one of [1] to

[13] , wherein the composition contains at least (B), and the composition is added to the food such that the concentration b of (B) in the food is 0.1 to 50,000 ppb by weight relative to the total weight of the food when consumed.

[0067]

[15] The composition according to any one of [1] to

[14] , wherein the composition contains at least (C), and the composition is added to the food such that the concentration of (C) in the food is 0.1 to 50,000 ppb by weight relative to the total weight of the food when consumed.

[0068]

[16] When the composition according to any one of [1] to

[15] contains at least (A) and (B), the composition is added to the food in such a way that the weight ratio (a:b) of the concentration a of (A) to the concentration b of (B) in the food is a:b = 1:0.001 to 1000;

[0069] When the composition contains at least (A) and (C), the composition is added to the food in such a way that the weight ratio (a:c) of the concentration a of (A) to the concentration c of (C) in the food is a:c = 1:0.001 to 1000;

[0070] When the composition contains at least (B) and (C), the composition is added to the food in such a way that the weight ratio (b:c) of the concentration b of (B) to the concentration c of (C) in the food is b:c = 1:0.001 to 1000.

[0071]

[17] The composition according to any one of [1] to

[16] , wherein the composition contains at least (A) and (B) and is added to the food in such a way that the weight ratio (a:b) of the concentration a of (A) to the concentration b of (B) in the food is a:b = 1:0.001 to 1000.

[0072]

[18] The composition according to any one of [1] to

[17] , wherein the composition contains at least (A) and (C) and is added to the food in such a way that the weight ratio (a:c) of the concentration a of (A) to the concentration c of (C) in the food is a:c = 1:0.001 to 1000.

[0073]

[19] The composition according to any one of [1] to

[18] , wherein the composition contains at least (B) and (C) and is added to the food in such a way that the weight ratio (b:c) of the concentration b of (B) to the concentration c of (C) in the food is b:c = 1:0.001 to 1000.

[0074]

[20] A method for manufacturing a food, comprising adding at least two compounds selected from the group consisting of (A) a compound represented by general formula (I), (B) β-caryophyllene oxide and (C) a compound represented by general formula (II):

[0075]

Transformation 3

[0076]

[0077] [In the formula, ring A is a 5- or 6-membered saturated or unsaturated carbon ring, or a 5- or 6-membered saturated or unsaturated oxygen- or nitrogen-containing heterocycle.]

[0078] R 1 The radical can be an oxo group, a hydroxyl group, an alkoxy group with 1 to 4 carbon atoms, an acyloxy group with 1 to 4 carbon atoms, or a hydrocarbon group or hydrogen atom with 1 to 8 carbon atoms that may have substituents. 1 When the hydrocarbon group having 1 to 8 carbon atoms that can have substituents is a hydrocarbon group, the carbon atoms in the hydrocarbon group can bond with the carbon atoms of ring A to form a cross-linked structure or a saturated or unsaturated ring structure.

[0079] R 2 It consists of a hydrocarbon group, a hydroxyl group, or a hydrogen atom with 1 to 8 carbon atoms;

[0080] [n represents an integer from 1 to 3]

[0081]

Chemistry 4

[0082]

[0083] [In the formula, R] 3 It is an acyl group, hydroxyl group, pyrrole group, or acyloxy group with 1 to 6 carbon atoms;

[0084] Z is a single bond or an alkylene group having 1 to 6 carbon atoms;

[0085] R4 For substituents;

[0086] m represents an integer from 0 to 3.

[0087]

[21] According to the manufacturing method described in

[20] , (A) is at least one compound selected from the group consisting of methylcyclopentenolone, γ-butyrolactone, 2-methyltetrahydrofuran-3-one, α-angelicolone, maltol, 3-methyl-1,2-cyclohexanedione, γ-dodecanolide, 5-dodecanolide, 4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one and D-camphor.

[0088]

[22] According to the manufacturing method described in

[20] or

[21] , the (C) is at least one compound selected from the group consisting of furfural, 2-acetylfuran, 2-acetyl-5-methylfuran, 3-acetyl-2,5-dimethylfuran, furfuryl alcohol, 1-furfurylpyrrole, furfuryl propionate, 5-methylfurfural and 5-(hydroxymethyl)furfural.

[0089]

[23] In the manufacturing method according to any one of

[20] to

[22] , the at least two compounds selected from the group consisting of (A), (B) and (C) are any one of (i) to (xviii) below.

[0090] (i) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfural.

[0091] (ii) Select at least two compounds from the group consisting of (A) γ-butyrolactone, (B) β-caryophyllene oxide and (C) furfural.

[0092] (iii) At least two compounds selected from the group consisting of (A) 2-methyltetrahydrofuran-3-one, (B) β-caryophyllene oxide and (C) furfural.

[0093] (iv) Select at least two compounds from the group consisting of (A) α-angelicin, (B) β-caryophyllene oxide and (C) furfural.

[0094] (v) Select at least two compounds from the group consisting of (A) maltol, (B) β-caryophyllene oxide, and (C) furfural.

[0095] (vi) Select at least two compounds from the group consisting of (A) 3-methyl-1,2-cyclohexanedione, (B) β-caryophyllene oxide and (C) furfural.

[0096] (vii) Select at least two compounds from the group consisting of (A) γ-dodecanolide, (B) β-caryophyllene oxide and (C) furfural.

[0097] (viii) Select at least two compounds from the group consisting of (A) 5-dodecanolide, (B) β-caryophyllene oxide and (C) furfural.

[0098] (ix) At least two compounds selected from the group consisting of (A) 4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one, (B) β-caryophyllene oxide and (C) furfural.

[0099] (x) Select at least two compounds from the group consisting of (A) D-camphor, (B) β-caryophyllene oxide and (C) furfural.

[0100] (xi) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 2-acetylfuran.

[0101] (xii) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 2-acetyl-5-methylfuran.

[0102] (xiii) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 3-acetyl-2,5-dimethylfuran.

[0103] (xiv) Select at least two compounds from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfuryl alcohol.

[0104] (xv) Select at least two compounds from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 1-furfurylpyrrole.

[0105] (xvi) Select at least two compounds from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfuryl propionate.

[0106] (xvii) Select at least two compounds from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 5-methylfurfural.

[0107] (xviii) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 5-(hydroxymethyl)furfural.

[0108]

[24] In the manufacturing method according to any one of

[20] to

[23] , the at least two compounds selected from the group consisting of (A), (B) and (C) are at least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfural.

[0109]

[25] The food produced by any one of

[20] to

[24] is a food that enhances the oral cavity coverage sensation.

[0110]

[26] The manufacturing method according to any one of

[20] to

[25] includes adding (A), (B) and (C).

[0111]

[27] The manufacturing method according to any one of

[20] to

[26] , wherein the manufacturing method includes adding (A) in such a way that the concentration a of (A) in the food is 0.05 to 5000 ppb by weight relative to the total weight of the food when it is consumed;

[0112] The manufacturing method includes adding (B) in such a way that the concentration b of (B) in the food is 0.1 to 50,000 ppb by weight relative to the total weight of the food when it is consumed.

[0113] The manufacturing method includes adding (C) in such a manner that the concentration of (C) in the food is 0.1 to 50,000 ppb relative to the total weight of the food when it is consumed.

[0114]

[28] The manufacturing method according to any one of

[20] to

[27] , the manufacturing method comprising adding at least (A), the addition of (A) being carried out in such a manner that the concentration a of (A) in the food is 0.05 to 5000 ppb by weight relative to the total weight of the food when consumed.

[0115]

[29] The manufacturing method according to any one of

[20] to

[28] , the manufacturing method comprising adding at least (B) in such a way that the concentration b of (B) in the food is 0.1 to 50,000 ppb by weight relative to the total weight of the food when consumed.

[0116]

[30] The manufacturing method according to any one of

[20] to

[29] , the manufacturing method comprising adding at least (C), the addition of (C) being carried out in such a way that the concentration c of (C) in the food is 0.1 to 50,000 ppb by weight relative to the total weight of the food when consumed.

[0117]

[31] The manufacturing method according to any one of

[20] to

[30] , wherein when at least (A) and (B) are added, the addition of (A) and (B) is carried out in such a way that the weight ratio (a:b) of the concentration a of (A) to the concentration b of (B) in the food is a:b = 1:0.001 to 1000;

[0118] The preparation method includes adding at least (A) and (C) in such a way that the weight ratio (a:c) of the concentration a of (A) to the concentration c of (C) in the food is a:c = 1:0.001 to 1000;

[0119] The preparation method includes adding at least (B) and (C) in such a way that the weight ratio (b:c) of the concentration b of (B) to the concentration c of (C) in the food is b:c = 1:0.001 to 1000.

[0120]

[32] The manufacturing method according to any one of

[20] to

[31] , the manufacturing method comprising adding at least (A) and (B) in such a manner that the weight ratio (a:b) of the concentration a of (A) in the food to the concentration b of (B) in the food is a:b = 1:0.001 to 1000.

[0121]

[33] The manufacturing method according to any one of

[20] to

[32] , the manufacturing method comprising adding at least (A) and (C), the addition of (A) and (C) such that the weight ratio (a:c) of the concentration a of (A) to the concentration c of (C) in the food is a:c = 1:0.001 to 1000.

[0122]

[34] The manufacturing method according to any one of

[20] to

[33] , the manufacturing method comprising adding at least (B) and (C) in such a manner that the weight ratio (b:c) of the concentration b of (B) to the concentration c of (C) in the food is b:c = 1:0.001 to 1000.

[0123]

[35] A food product comprising at least two compounds selected from the group consisting of (A) a compound represented by general formula (I), (B) β-caryophyllene oxide and (C) a compound represented by general formula (II):

[0124]

Transformation 5

[0125]

[0126] [In the formula, ring A is a 5- or 6-membered saturated or unsaturated carbon ring, or a 5- or 6-membered saturated or unsaturated oxygen- or nitrogen-containing heterocycle.]

[0127] R 1 The radical can be an oxo group, a hydroxyl group, an alkoxy group with 1 to 4 carbon atoms, an acyloxy group with 1 to 4 carbon atoms, or a hydrocarbon group or hydrogen atom with 1 to 8 carbon atoms that may have substituents. 1When the hydrocarbon group having 1 to 8 carbon atoms that can have substituents is a hydrocarbon group, the carbon atoms in the hydrocarbon group can bond with the carbon atoms of ring A to form a cross-linked structure or a saturated or unsaturated ring structure;

[0128] R 2 It consists of a hydrocarbon group, a hydroxyl group, or a hydrogen atom with 1 to 8 carbon atoms;

[0129] [n represents an integer from 1 to 3]

[0130]

Transformation 6

[0131]

[0132] [In the formula, R] 3 It is an acyl group, hydroxyl group, pyrrole group, or acyloxy group with 1 to 6 carbon atoms;

[0133] Z is a single bond or an alkylene group having 1 to 6 carbon atoms;

[0134] R 4 For substituents;

[0135] m represents an integer from 0 to 3.

[0136]

[36] According to the food described in

[35] , (A) is at least one compound selected from the group consisting of methylcyclopentenolone, γ-butyrolactone, 2-methyltetrahydrofuran-3-one, α-angelicolone, maltol, 3-methyl-1,2-cyclohexanedione, γ-dodecanolide, 5-dodecanolide, 4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one and D-camphor.

[0137]

[37] In the food according to

[35] or

[36] , (C) is at least one compound selected from the group consisting of furfural, 2-acetylfuran, 2-acetyl-5-methylfuran, 3-acetyl-2,5-dimethylfuran, furfuryl alcohol, 1-furfurylpyrrole, furfuryl propionate, 5-methylfurfural and 5-(hydroxymethyl)furfural.

[0138]

[38] The food according to any one of

[35] to

[37] contains any one of the following (i) to (xviii) as (A), (B) and (C).

[0139] (i) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfural.

[0140] (ii) Select at least two compounds from the group consisting of (A) γ-butyrolactone, (B) β-caryophyllene oxide and (C) furfural.

[0141] (iii) At least two compounds selected from the group consisting of (A) 2-methyltetrahydrofuran-3-one, (B) β-caryophyllene oxide and (C) furfural.

[0142] (iv) Select at least two compounds from the group consisting of (A) α-angelicin, (B) β-caryophyllene oxide and (C) furfural.

[0143] (v) Select at least two compounds from the group consisting of (A) maltol, (B) β-caryophyllene oxide, and (C) furfural.

[0144] (vi) Select at least two compounds from the group consisting of (A) 3-methyl-1,2-cyclohexanedione, (B) β-caryophyllene oxide and (C) furfural.

[0145] (vii) Select at least two compounds from the group consisting of (A) γ-dodecanolide, (B) β-caryophyllene oxide and (C) furfural.

[0146] (viii) Select at least two compounds from the group consisting of (A) 5-dodecanolide, (B) β-caryophyllene oxide and (C) furfural.

[0147] (ix) At least two compounds selected from the group consisting of (A) 4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one, (B) β-caryophyllene oxide and (C) furfural.

[0148] (x) Select at least two compounds from the group consisting of (A) D-camphor, (B) β-caryophyllene oxide and (C) furfural.

[0149] (xi) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 2-acetylfuran.

[0150] (xii) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 2-acetyl-5-methylfuran.

[0151] (xiii) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 3-acetyl-2,5-dimethylfuran.

[0152] (xiv) Select at least two compounds from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfuryl alcohol.

[0153] (xv) Select at least two compounds from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 1-furfurylpyrrole.

[0154] (xvi) Select at least two compounds from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfuryl propionate.

[0155] (xvii) Select at least two compounds from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 5-methylfurfural.

[0156] (xviii) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 5-(hydroxymethyl)furfural.

[0157]

[39] The food according to any one of

[35] to

[38] contains at least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfural.

[0158]

[40] The food according to any one of

[35] to

[39] is a food that enhances the oral cavity coverage.

[0159]

[41] The food according to any one of

[35] to

[40] contains (A), (B) and (C).

[0160]

[42] When the food according to any one of

[35] to

[41] contains at least (A), the concentration a of (A) in the food is 0.05 to 5000 ppb by weight relative to the total weight of the food when consumed;

[0161] When the food contains at least (B), the concentration b of (B) in the food is 0.1 to 50,000 ppb by weight relative to the total weight of the food when consumed;

[0162] When the food contains at least (C), the concentration c of (C) in the food is 0.1 to 50,000 ppb by weight relative to the total weight of the food when consumed.

[0163]

[43] The food according to any one of

[35] to

[42] , wherein the food contains at least (A), and the concentration a of (A) in the food is 0.05 to 5000 ppb by weight relative to the total weight of the food when consumed.

[0164]

[44] The food according to any one of

[35] to

[43] , wherein the food contains at least (B), and the concentration b of (B) in the food is 0.1 to 50,000 ppb by weight relative to the total weight of the food when consumed.

[0165]

[45] The food according to any one of

[35] to

[44] , wherein the food contains at least (C), and the concentration of (C) in the food is 0.1 to 50,000 ppb by weight relative to the total weight of the food when consumed.

[0166]

[46] In any one of

[35] to

[45] , when the food contains at least (A) and (B), the weight ratio (a:b) of the concentration a of (A) to the concentration b of (B) in the food is a:b = 1:0.001 to 1000;

[0167] When the food contains at least (A) and (C), the weight ratio (a:c) of the concentration a of (A) to the concentration c of (C) in the food is a:c = 1:0.001 to 1000;

[0168] When the food contains at least (B) and (C), the weight ratio (b:c) of the concentration b of (B) to the concentration c of (C) in the food is b:c = 1:0.001 to 1000.

[0169]

[47] The food according to any one of

[35] to

[46] , wherein the food contains at least (A) and (B), and the weight ratio (a:b) of the concentration a of (A) to the concentration b of (B) in the food is a:b = 1:0.001 to 1000.

[0170]

[48] ​​The food according to any one of

[35] to

[47] , wherein the food contains at least (A) and (C), and the weight ratio (a:c) of the concentration a of (A) to the concentration c of (C) in the food is a:c = 1:0.001 to 1000.

[0171]

[49] The food according to any one of

[35] to

[48] , wherein the food contains at least (B) and (C), and the weight ratio (b:c) of the concentration b of (B) to the concentration c of (C) in the food is b:c = 1:0.001 to 1000.

[0172]

[50] A method for enhancing oral coverage, comprising adding at least two compounds selected from the group consisting of (A) a compound represented by general formula (I), (B) β-caryophyllene oxide and (C) a compound represented by general formula (II):

[0173]

Transformation 7

[0174]

[0175] [In the formula, ring A is a 5- or 6-membered saturated or unsaturated carbon ring, or a 5- or 6-membered saturated or unsaturated oxygen- or nitrogen-containing heterocycle.]

[0176] R 1The radical can be an oxo group, a hydroxyl group, an alkoxy group with 1 to 4 carbon atoms, an acyloxy group with 1 to 4 carbon atoms, or a hydrocarbon group or hydrogen atom with 1 to 8 carbon atoms that may have substituents. 1 When the hydrocarbon group having 1 to 8 carbon atoms that can have substituents is a hydrocarbon group, the carbon atoms in the hydrocarbon group can bond with the carbon atoms of ring A to form a cross-linked structure or a saturated or unsaturated ring structure;

[0177] R 2 It consists of a hydrocarbon group, a hydroxyl group, or a hydrogen atom with 1 to 8 carbon atoms;

[0178] [n represents an integer from 1 to 3]

[0179]

Transformation 8

[0180]

[0181] [In the formula, R] 3 It is an acyl group, hydroxyl group, pyrrole group, or acyloxy group with 1 to 6 carbon atoms;

[0182] Z is a single bond or an alkylene group having 1 to 6 carbon atoms;

[0183] R 4 For substituents;

[0184] m represents an integer from 0 to 3.

[0185]

[51] According to the enhancement method of

[50] , (A) is at least one compound selected from the group consisting of methylcyclopentenolone, γ-butyrolactone, 2-methyltetrahydrofuran-3-one, α-angelicolone, maltol, 3-methyl-1,2-cyclohexanedione, γ-dodecanolide, 5-dodecanolide, 4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one and D-camphor.

[0186]

[52] According to the enhancement method of

[50] or

[51] , the (C) is at least one compound selected from the group consisting of furfural, 2-acetylfuran, 2-acetyl-5-methylfuran, 3-acetyl-2,5-dimethylfuran, furfuryl alcohol, 1-furfurylpyrrole, furfuryl propionate, 5-methylfurfural and 5-(hydroxymethyl)furfural.

[0187]

[53] In any one of the enhancement methods according to

[50] to

[52] , the at least two compounds selected from the group consisting of (A), (B) and (C) are any one of (i) to (xviii) below.

[0188] (i) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfural.

[0189] (ii) Select at least two compounds from the group consisting of (A) γ-butyrolactone, (B) β-caryophyllene oxide and (C) furfural.

[0190] (iii) At least two compounds selected from the group consisting of (A) 2-methyltetrahydrofuran-3-one, (B) β-caryophyllene oxide and (C) furfural.

[0191] (iv) Select at least two compounds from the group consisting of (A) α-angelicin, (B) β-caryophyllene oxide and (C) furfural.

[0192] (v) Select at least two compounds from the group consisting of (A) maltol, (B) β-caryophyllene oxide, and (C) furfural.

[0193] (vi) Select at least two compounds from the group consisting of (A) 3-methyl-1,2-cyclohexanedione, (B) β-caryophyllene oxide and (C) furfural.

[0194] (vii) Select at least two compounds from the group consisting of (A) γ-dodecanolide, (B) β-caryophyllene oxide and (C) furfural.

[0195] (viii) Select at least two compounds from the group consisting of (A) 5-dodecanolide, (B) β-caryophyllene oxide and (C) furfural.

[0196] (ix) At least two compounds selected from the group consisting of (A) 4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one, (B) β-caryophyllene oxide and (C) furfural.

[0197] (x) Select at least two compounds from the group consisting of (A) D-camphor, (B) β-caryophyllene oxide and (C) furfural.

[0198] (xi) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 2-acetylfuran.

[0199] (xii) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 2-acetyl-5-methylfuran.

[0200] (xiii) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 3-acetyl-2,5-dimethylfuran.

[0201] (xiv) Select at least two compounds from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfuryl alcohol.

[0202] (xv) Select at least two compounds from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 1-furfurylpyrrole.

[0203] (xvi) Select at least two compounds from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfuryl propionate.

[0204] (xvii) Select at least two compounds from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 5-methylfurfural.

[0205] (xviii) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 5-(hydroxymethyl)furfural.

[0206]

[54] In any one of the enhancement methods according to

[50] to

[53] , the at least two compounds selected from the group consisting of (A), (B) and (C) are at least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfural.

[0207]

[55] The enhancement method according to any one of

[50] to

[54] includes adding (A), (B) and (C).

[0208]

[56] The enhancement method according to any one of

[50] to

[55] , the enhancement method comprising adding (A) in such a manner that the addition of (A) results in a concentration a of (A) in the food relative to the total weight of the food when consumed being 0.05 to 5000 ppb by weight;

[0209] The enhancement method includes adding (B) in such a way that the concentration b of (B) in the food is 0.1 to 50,000 ppb by weight relative to the total weight of the food when it is consumed;

[0210] The enhancement method includes adding (C) in such a manner that the concentration c of (C) in the food is 0.1 to 50,000 ppb relative to the total weight of the food when consumed.

[0211]

[57] The enhancement method according to any one of

[50] to

[56] , the enhancement method comprising adding at least (A), the addition of (A) being carried out in such a manner that the concentration a of (A) in the food is 0.05 to 5000 ppb by weight relative to the total weight of the food when consumed.

[0212]

[58] The enhancement method according to any one of

[50] to

[57] , the enhancement method comprising adding at least (B), the addition of (B) being carried out in such a manner that the concentration b of (B) in the food is 0.1 to 50,000 ppb by weight relative to the total weight of the food when consumed.

[0213]

[59] The enhancement method according to any one of

[50] to

[58] , the enhancement method comprising adding at least (C), the addition of (C) being carried out in such a manner that the concentration c of (C) in the food is 0.1 to 50,000 ppb by weight relative to the total weight of the food when consumed.

[0214]

[60] The enhancement method according to any one of

[50] to

[59] , wherein the enhancement method comprises adding at least (A) and (B) such that the addition of (A) and (B) is carried out in such a manner that the weight ratio (a:b) of the concentration a of (A) to the concentration b of (B) in the food is a:b = 1:0.001 to 1000;

[0215] The enhancement method includes adding at least (A) and (C) in such a way that the weight ratio (a:c) of the concentration a of (A) to the concentration c of (C) in the food is a:c = 1:0.001 to 1000;

[0216] The enhancement method includes adding at least (B) and (C) in such a manner that the weight ratio (b:c) of the concentration b of (B) to the concentration c of (C) in the food is b:c = 1:0.001 to 1000.

[0217]

[61] The enhancement method according to any one of

[50] to

[60] , the enhancement method comprising adding at least (A) and (B), the addition of (A) and (B) being carried out in such a manner that the weight ratio (a:b) of the concentration a of (A) in the food to the concentration b of (B) is a:b = 1:0.001 to 1000.

[0218]

[62] The enhancement method according to any one of

[50] to

[61] , the enhancement method comprising adding at least (A) and (C) in such a manner that the weight ratio (a:c) of the concentration a of (A) to the concentration c of (C) in the food is a:c = 1:0.001 to 1000.

[0219]

[63] The enhancement method according to any one of

[50] to

[62] , the enhancement method comprising adding at least (B) and (C), the addition of (B) and (C) being carried out in such a way that the weight ratio (b:c) of the concentration b of (B) to the concentration c of (C) in the food is b:c = 1:0.001 to 1000.

[0220] Invention Effects

[0221] According to the present invention, a flavoring composition that effectively enhances the oral envelopment sensation can be provided. Furthermore, according to the present invention, a flavoring composition that does not impart any off-flavor to food and effectively enhances the oral envelopment sensation can be provided.

[0222] According to the present invention, a food product that effectively enhances the oral sensation of fullness and a method thereof can be provided. Furthermore, according to the present invention, a food product without odor that effectively enhances the oral sensation of fullness and a method thereof can be provided.

[0223] According to the present invention, a method that can effectively enhance the oral cavity's sense of coverage can be provided. Furthermore, according to the present invention, a method that can effectively enhance the oral cavity's sense of coverage without imparting any unpleasant odor to food can be provided. Detailed Implementation

[0224] The main feature of the fragrance composition of the present invention (hereinafter also referred to as "the composition of the present invention") is that it contains, as an active ingredient, at least two compounds selected from the group consisting of (A) a compound represented by general formula (I) (also referred to as "(A)" in this specification), (B) β-caryophyllene oxide (also referred to as "(B)" in this specification), and (C) a compound represented by general formula (II) (also referred to as "(C)" in this specification):

[0225]

Chemistry 9

[0226]

[0227] [In the formula, ring A is a 5- or 6-membered saturated or unsaturated carbon ring, or a 5- or 6-membered saturated or unsaturated oxygen- or nitrogen-containing heterocycle.]

[0228] R 1 The radical can be an oxo group, a hydroxyl group, an alkoxy group with 1 to 4 carbon atoms, an acyloxy group with 1 to 4 carbon atoms, or a hydrocarbon group or hydrogen atom with 1 to 8 carbon atoms that may have substituents. 1 When the hydrocarbon group having 1 to 8 carbon atoms that can have substituents is a hydrocarbon group, the carbon atoms in the hydrocarbon group can bond with the carbon atoms of ring A to form a cross-linked structure or a saturated or unsaturated ring structure.

[0229] R 2 It consists of a hydrocarbon group, a hydroxyl group, or a hydrogen atom with 1 to 8 carbon atoms;

[0230] [n represents an integer from 1 to 3]

[0231]

Chemistry 10

[0232]

[0233] [In the formula, R] 3 It is an acyl group, hydroxyl group, pyrrole group, or acyloxy group with 1 to 6 carbon atoms;

[0234] Z is a single bond or an alkylene group having 1 to 6 carbon atoms;

[0235] R 4 For substituents;

[0236] m represents an integer from 0 to 3.

[0237] In this invention, "spice" refers to food additives used to impart aroma, flavor, taste, etc. to food.

[0238] [Ingredients (A)]

[0239] In this specification, the compound represented by the general formula (I) used as (A) in this invention is sometimes referred to as "compound (I)".

[0240] The following describes the groups of general formula (I).

[0241] In this specification, "hydrocarbon group" can be saturated or unsaturated, for example, alkyl, alkenyl, alkynyl, alkaneyl, etc.

[0242] In this specification, "alkyl group having 1 to 8 carbon atoms" can be linear or branched. Specific examples of alkyl groups having 1 to 8 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, neopentyl, isopentyl, 1-ethylpropyl, hexyl, isohexyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, octyl, etc.

[0243] In this specification, "alkenyl group having 2 to 8 carbon atoms" can be linear or branched. Specific examples of alkenyl groups having 2 to 8 carbon atoms include vinyl, 1-propenyl, 2-propenyl, 1-methylethylene, 1-butenyl, 2-butenyl, 3-butenyl, 2-methyl-1-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 3-methyl-2-butenyl, 1-hexenyl, 3-hexenyl, 5-hexenyl, 4-methyl-3-pentenyl, 1-heptenyl, 1-octenyl, etc.

[0244] In this specification, "alkynyl group with 2 to 8 carbon atoms" can be linear or branched. Specific examples of alkynyl groups with 2 to 8 carbon atoms include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-heptynyl, and 1-octyynyl.

[0245] In this specification, "alkylene group having 1 to 8 carbon atoms" can be linear or branched. Specific examples of alkylene groups having 1 to 8 carbon atoms include methyl alkylene group, ethyl alkylene group, propyl alkylene group, isopropyl alkylene group, butyl alkylene group, pentyl alkylene group, hexyl alkylene group, heptyl alkylene group, octyl alkylene group, etc.

[0246] In this specification, "may have substituents" means that there is no substitution or that there is one or more substituents at a position where substitution is possible. When there are two or more substituents, the substituents may be the same or different.

[0247] In this specification, the term "substituent" as "may have substituents" includes, for example, halogen atoms, hydroxyl groups, nitro groups, cyano groups, alkyl groups, alkoxy groups, alkoxycarbonyl groups, acyl groups, acyloxy groups, amino groups, oxo groups, etc., and the substituent can also be replaced by the aforementioned substituents.

[0248] In this specification, "alkoxy group having 1 to 4 carbon atoms" can be linear or branched. Specific examples of alkoxy groups having 1 to 4 carbon atoms include methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, tert-butoxy, and isobutoxy.

[0249] In this specification, specific examples of "acyloxy groups having 1 to 4 carbon atoms" may include formyloxy, acetoxy, propionyloxy, etc.

[0250] In general formula (I), ring A represents a saturated or unsaturated carbon ring, or a saturated or unsaturated oxygen- or nitrogen-containing heterocycle, preferably a saturated or unsaturated carbon ring or oxygen-containing heterocycle. The number of atoms in ring A is 5 or 6, preferably 5. When ring A is an oxygen- or nitrogen-containing heterocycle, the number of heteroatoms in the heterocycle is 1 or 2, preferably 1.

[0251] In one implementation, ring A can be a 5-membered saturated or unsaturated carbon ring or an oxygen- or nitrogen-containing heterocycle.

[0252] In another embodiment, ring A is a 5- or 6-membered saturated or unsaturated carbon ring or a 5- or 6-membered saturated or unsaturated oxygen-containing heterocycle (preferably a carbon ring or an oxygen-containing heterocycle with 1 heteroatom).

[0253] In another embodiment, ring A can be a 5-membered saturated or unsaturated carbon ring or a 5-membered saturated or unsaturated oxygen-containing heterocycle (preferably a carbon ring or an oxygen-containing heterocycle with 1 heteroatom).

[0254] Specific examples of ring A include carbocyclic rings such as cyclopentane ring, cyclopentene ring, cyclopentadiene ring, cyclohexane ring, cyclohexene ring, 1,3-cyclohexadiene ring, 1,4-cyclohexadiene ring, and benzene ring; oxygen-containing heterocycles such as tetrahydrofuran ring, 2,3-dihydrofuran ring, 2,5-dihydrofuran ring, furan ring, tetrahydropyran ring, 2H-pyran ring, and 4H-pyran ring; and nitrogen-containing heterocycles such as pyrrolidine ring and piperidine ring.

[0255] As shown in general formula (I), ring A is substituted with at least one oxy group.

[0256] R in general formula (I) 1 and R 2 All are substituents bonded to substituted positions on ring A. R 1 and R 2 It can bond with different atoms (carbon atoms, heteroatoms) or, as long as it can be substituted, it can bond with the same carbon atom.

[0257] R in general formula (I) 1 It can represent an oxygen group, a hydroxyl group, an alkoxy group with 1 to 4 carbon atoms, an acyloxy group with 1 to 4 carbon atoms, a hydrocarbon group with 1 to 8 carbon atoms that may have substituents, or a hydrogen atom.

[0258] As R 1 Specific examples of "alkoxy group having 1 to 4 carbon atoms" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, tert-butoxy, and isobutoxy, with methoxy being preferred. The number of carbon atoms in this alkoxy group is preferably 1 to 3, and more preferably 1 or 2.

[0259] As R 1 Specific examples of "acyloxy group having 1 to 4 carbon atoms" include formyloxy, acetoxy, propionyloxy, etc., with formyloxy and acetoxy being preferred. The number of carbon atoms in this acyloxy group is preferably 1 to 3, and more preferably 1 or 2.

[0260] As R 1 The phrase "a hydrocarbon group having 1 to 8 carbon atoms that may have a substituent" includes, for example, alkyl groups having 1 to 8 carbon atoms, alkenyl groups having 2 to 8 carbon atoms, alkynyl groups having 2 to 8 carbon atoms, and alkane groups having 1 to 8 carbon atoms. Alkyl groups having 1 to 8 carbon atoms and alkenyl groups having 2 to 8 carbon atoms are preferred.

[0261] As R 1Specific examples of "alkyl groups having 1 to 8 carbon atoms" include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, neopentyl, isopentyl, 1-ethylpropyl, hexyl, isohexyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, octyl, etc., with methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, and tert-butyl being preferred, methyl, ethyl, propyl, and isopropyl being more preferred, and methyl and ethyl being particularly preferred. The alkyl group preferably has 1 to 6 carbon atoms, more preferably 1 to 5, further preferably 1 to 4, and particularly preferably 1 to 3.

[0262] As R 1 Specific examples of "alkenyl groups with 2 to 8 carbon atoms" include ethylene, 1-propenyl, 2-propenyl, 1-methylethylene, 1-butenyl, 2-butenyl, 3-butenyl, 2-methyl-1-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 3-methyl-2-butenyl, 1-hexenyl, 3-hexenyl, 5-hexenyl, 4-methyl-3-pentenyl, 1-heptenyl, 1-octenyl, etc., with vinyl and 1-methylvinyl being preferred. The alkyl group preferably has 2 to 6 carbon atoms, more preferably 2 to 5, more preferably 2 to 4, and particularly preferably 2 or 3.

[0263] As R 1 Specific examples of "alkynyl group with 2 to 8 carbon atoms" include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-heptyynyl, 1-octyynyl, etc., with ethynyl, 1-propynyl, and 2-propynyl being preferred. The number of carbon atoms in this alkynyl group is preferably 2 to 6, more preferably 2 to 5, even more preferably 2 to 4, and particularly preferably 2 or 3.

[0264] As R 1 Specific examples of "alkylene groups having 1 to 8 carbon atoms" include methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, heptyl, and octyl groups, with methyl, ethyl, propyl, and isopropyl groups being preferred. The number of carbon atoms in this alkylene group is preferably 1 to 6, more preferably 1 to 5, further preferably 1 to 4, and particularly preferably 1 to 3.

[0265] As R 1The term "substituent" in "a hydrocarbon group having 1 to 8 carbon atoms that may have a substituent" can include, for example, halogen atoms, hydroxyl groups, nitro groups, cyano groups, alkyl groups, alkoxy groups, alkoxycarbonyl groups, acyl groups, acyloxy groups, amino groups, oxo groups, etc., with substituents containing oxygen atoms (e.g., hydroxyl, alkoxycarbonyl, oxo groups, etc.) being preferred. In R 1 When the "hydrocarbon group with 1 to 8 carbon atoms" has substituents, the number of substituents is not particularly limited as long as they are substituted, but is preferably 1 to 3, more preferably 1 or 2. 1 When a "hydrocarbon group with 1 to 8 carbon atoms" has two or more substituents, the substituents can be the same or different.

[0266] R in general formula (I) 1 When the hydrocarbon group having 1 to 8 carbon atoms that can have substituents is a hydrocarbon group, the carbon atoms in the hydrocarbon group can bond with the carbon atoms of ring A to form a cross-linked structure or a saturated or unsaturated ring structure.

[0267] R 1 Preferably, the radical is an oxo group, a hydroxyl group, an alkoxy group (e.g., methoxy) having 1 to 4 carbon atoms, an acyloxy group (e.g., acetoxy) having 1 to 4 carbon atoms, a hydrocarbon group (e.g., alkyl, alkenyl) having 1 to 8 carbon atoms that may have a substituent, or a hydrogen atom. More preferably, the radical is an oxo group, a hydroxyl group, a methoxy group, an acetoxy group, an alkyl group (e.g., methyl, ethyl, heptyl, octyl) having 1 to 8 carbon atoms that may have a substituent, an alkenyl group (e.g., 1-methylvinyl) having 2 to 8 carbon atoms that may have a substituent, or a hydrogen atom. Particularly preferred are oxo groups, hydroxyl groups, methoxy groups, acetoxy groups, methyl groups (e.g., hydroxyl, alkoxycarbonyl) having a substituent, ethyl groups (e.g., hydroxyl, alkoxycarbonyl) having a substituent, isopropenyl, heptyl, octyl, or a hydrogen atom.

[0268] R in general formula (I) 2 It represents a hydrocarbon group, hydroxyl group, or hydrogen atom with 1 to 8 carbon atoms.

[0269] R 2 Preferably, the alkyl group has 1 to 8 carbon atoms, the alkyl subunit has 1 to 8 carbon atoms, the hydroxyl group or the hydrogen atom is preferred, more preferably the alkyl group has 1 to 8 carbon atoms (e.g., methyl, ethyl, pentyl, etc.), the alkyl subunit has 1 to 8 carbon atoms (e.g., propane subunit, etc.), the hydroxyl group or the hydrogen atom is preferred, and methyl, pentyl, propane subunit, hydroxyl or the hydrogen atom is particularly preferred.

[0270] In general formula (I), n represents an integer from 1 to 3. n preferably represents 1 or 2, and more preferably 1.

[0271] As a way, when n in general formula (I) is 2 or 3, multiple R 2 They can be the same or different.

[0272] The following shows a preferred compound (I).

[0273] [Compound (IA)]

[0274] Compound (I): Ring A is a 5- or 6-membered saturated or unsaturated carbon ring;

[0275] R 1 R is an oxo group, a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, an acyloxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 8 carbon atoms (preferably 1 to 6) that may have substituents, an alkenyl group having 2 to 8 carbon atoms (preferably 2 to 6) that may have substituents, or a hydrogen atom. 1 When the alkyl group has 1 to 8 (preferably 1 to 6) carbon atoms and the alkenyl group has 2 to 8 (preferably 2 to 6) carbon atoms and the alkenyl group has 2 to 8 carbon atoms and the alkenyl group can bond with the carbon atoms of ring A to form a cross-linked structure or a saturated or unsaturated ring structure.

[0276] R 2 It is an alkyl group having 1 to 8 carbon atoms (preferably 1 to 6), an alkyl subgroup having 1 to 8 carbon atoms (preferably 1 to 6), a hydroxyl group, or a hydrogen atom;

[0277] n represents an integer from 1 to 3 (preferably 1 or 2).

[0278] [Compound(IB)]

[0279] Compound (I): Ring A is a 5- or 6-membered saturated or unsaturated oxygen-containing heterocycle;

[0280] R 1 R is an oxo group, a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, an acyloxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 8 carbon atoms (preferably 1 to 6) that may have substituents, an alkenyl group having 2 to 8 carbon atoms (preferably 2 to 6) that may have substituents, or a hydrogen atom. 1 When the number of carbon atoms in the alkyl or alkenyl group that can have substituents is 2 to 8 (preferably 2 to 6), the carbon atoms in the alkyl or alkenyl group can bond with the carbon atoms of ring A to form a cross-linked structure or a saturated or unsaturated ring structure.

[0281] R 2 It is an alkyl group having 1 to 8 carbon atoms (preferably 1 to 6), an alkyl subgroup having 1 to 8 carbon atoms (preferably 1 to 6), a hydroxyl group, or a hydrogen atom;

[0282] n represents an integer from 1 to 3 (preferably 1 or 2).

[0283] [Compound (IC)]

[0284] Compound (I): Ring A is a 5- or 6-membered saturated or unsaturated nitrogen-containing heterocycle;

[0285] R 1 is an oxo group, a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, an acyloxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 8 (preferably 1 to 6) carbon atoms which may have substituents, an alkenyl group having 2 to 8 (preferably 2 to 6) carbon atoms which may have substituents, or a hydrogen atom, and when R 1 is an alkyl group having 1 to 8 (preferably 1 to 6) carbon atoms which may have substituents or an alkenyl group having 2 to 8 (preferably 2 to 6) carbon atoms which may have substituents, the carbon atom in the alkyl or alkenyl group may be bonded to the carbon atom of Ring A to form a crosslinked structure or a saturated or unsaturated ring structure;

[0286] R 2 is an alkyl group having 1 to 8 (preferably 1 to 6) carbon atoms, an alkylene group having 1 to 8 (preferably 1 to 6) carbon atoms, a hydroxyl group, or a hydrogen atom;

[0287] n represents an integer of 1 to 3 (preferably 1, 2).

[0288] As one embodiment, Compound (I) may be a compound represented by the following general formula (Ia):

[0289]

Chemical formula 11

[0290]

[0291] 〔In the formula, Ring Aa is a 5- or 6-membered saturated or unsaturated carbocyclic ring, or a 5- or 6-membered saturated or unsaturated oxygen- or nitrogen-containing heterocyclic ring;

[0292] R 1a represents an oxo group, a hydroxyl group, or a hydrogen atom;

[0293] R 2a represents an alkyl group having 1 to 8 carbon atoms or a hydrogen atom;〕.

[0294] In this specification, the compound represented by the general formula (Ia) is sometimes referred to as "Compound (Ia)".

[0295] Hereinafter, each group of the general formula (Ia) will be described.

[0296] Ring Aa in the general formula (Ia) is the same as Ring A in the general formula (I), and the preferred modes and specific examples are also the same.

[0297] As shown in the general formula (Ia), Ring Aa is substituted with at least one oxo group.

[0298] In the general formula (Ia), the part represented by

Chemical formula 12

[0299]

Chemistry 12

[0300]

[0301] The preferred option is to choose from the following.

[0302]

Chemistry 13

[0303]

[0304] The above-mentioned part in general formula (Ia) is preferably selected from the following.

[0305]

Chemistry 14

[0306]

[0307] The above-mentioned portion in general formula (Ia) is particularly preferably selected from the following.

[0308]

Chemistry 15

[0309]

[0310] R in general formula (Ia) 1a and R 2a All are substituents bonded to substituted positions on ring Aa. R 1a and R 2a It can bond with different atoms (carbon atoms, heteroatoms) or, if it can be substituted, it can bond with the same carbon atom.

[0311] R in general formula (Ia) 1a Represents an oxo group, hydroxyl group, or hydrogen atom. R 1a Preferably, it contains hydroxyl groups or hydrogen atoms.

[0312] R in general formula (Ia) 2a It represents an alkyl group or hydrogen atom with 1 to 8 carbon atoms.

[0313] As R 2a Specific examples of "alkyl group having 1 to 8 carbon atoms" include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, neopentyl, isopentyl, 1-ethylpropyl, hexyl, isohexyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, octyl, etc., with methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, and tert-butyl being preferred, methyl, ethyl, propyl, and isopropyl being more preferred, and methyl and ethyl being particularly preferred. The alkyl group preferably has 1 to 6 carbon atoms, more preferably 1 to 5, further preferably 1 to 4, and particularly preferably 1 to 3.

[0314] R 2aPreferably an alkyl group having 1 to 6 carbon atoms or a hydrogen atom, more preferably an alkyl group having 1 to 4 carbon atoms or a hydrogen atom, still more preferably a methyl group, an ethylmethyl group, a propyl group, an isopropyl group or a hydrogen atom, and particularly preferably a methyl group, an ethyl group or a hydrogen atom.

[0315] The following shows the preferred compound (Ia).

[0316] [Compound (Ia-A)]

[0317] Compound (Ia): Ring A is a 5- or 6-membered saturated or unsaturated carbocyclic ring;

[0318] R 1a is an oxo group, a hydroxyl group or a hydrogen atom;

[0319] R 2a represents an alkyl group having 1 to 6 (preferably 1 to 4) carbon atoms or a hydrogen atom.

[0320] [Compound (Ia-B)]

[0321] Compound (Ia): Ring A is a 5- or 6-membered saturated or unsaturated oxygen-containing heterocyclic ring;

[0322] R 1a is an oxo group, a hydroxyl group or a hydrogen atom;

[0323] R 2a represents an alkyl group having 1 to 6 (preferably 1 to 4) carbon atoms or a hydrogen atom.

[0324] [Compound (Ia-C)]

[0325] Compound (Ia): Ring A is a 5- or 6-membered saturated or unsaturated nitrogen-containing heterocyclic ring;

[0326] R 1a is a hydrogen atom;

[0327] R 2a represents an alkyl group having 1 to 6 (preferably 1 to 4) carbon atoms or a hydrogen atom.

[0328] [Compound (Ia-D)]

[0329] In the general formula (Ia), the part represented by [Chemical Formula 16]

[0330] [Chemical Formula 16]

[0331]

[0332] is selected from the following;

[0333] [Chemical Formula 17]

[0334]

[0335] Compound (Ia): R 1a is an oxo group, a hydroxyl group or a hydrogen atom; R 2a represents an alkyl group having 1 to 6 (preferably 1 to 4) carbon atoms or a hydrogen atom.

[0336] [Compound (Ia-E)]

[0337] In the general formula (Ia), the part represented by

Chemical Formula 18

[0338]

Chemical Formula 18

[0339]

[0340] is selected from the following;

[0341]

Chemical Formula 19

[0342]

[0343] Compound (Ia): R 1a is an oxo group, a hydroxyl group or a hydrogen atom;

[0344] R 2a represents an alkyl group having 1 to 6 (preferably 1 to 4) carbon atoms or a hydrogen atom.

[0345] [Compound (Ia-F)]

[0346] Compound (Ia) represented by a general formula selected from the following;

[0347]

Chemical Formula 20

[0348]

[0349] 〔In each formula,

[0350] R 1a is an oxo group, a hydroxyl group or a hydrogen atom (preferably a hydroxyl group or a hydrogen atom); R 2a represents an alkyl group having 1 to 6 (preferably 1 to 4) carbon atoms or a hydrogen atom〕.

[0351] [Compound (Ia-G)]

[0352] Compound (Ia) represented by a general formula selected from the following;

[0353]

Chemical Formula 21

[0354]

[0355] 〔In each formula,

[0356] R 1a is an oxo group, a hydroxyl group or a hydrogen atom;

[0357] R 2a [Indicates alkyl or hydrogen atoms with 1 to 6 carbon atoms (preferably 1 to 4).]

[0358] [Compound (Ia-H)]

[0359] Compounds represented by the general formula selected from the following (Ia);

[0360]

Chemistry 22

[0361]

[0362] [In each form,]

[0363] R 1a It is an oxo group, a hydroxyl group, or a hydrogen atom;

[0364] R 2a [Indicates alkyl or hydrogen atoms with 1 to 6 carbon atoms (preferably 1 to 4).]

[0365] [Compound (Ia-I)]

[0366] Compounds represented by the general formula selected from the following (Ia);

[0367]

Chemistry 23

[0368]

[0369] [In each form,]

[0370] R 2a [Indicates alkyl or hydrogen atoms with 1 to 6 carbon atoms (preferably 1 to 4).]

[0371] [Compound (Ia-J)]

[0372] Compounds represented by the general formula selected from the following (Ia);

[0373]

Chemistry 24

[0374]

[0375] [In each form,]

[0376] R 1a It is an oxo group, a hydroxyl group, or a hydrogen atom (preferably a hydroxyl or hydrogen atom); R 2a [Indicates alkyl or hydrogen atoms with 1 to 6 carbon atoms (preferably 1 to 4).]

[0377] Specific examples of preferred compound (I) include the following.

[0378] • Methylcyclopentenolone (CAS registration number 80-71-7):

[0379]

Chemistry 25

[0380]

[0381] ·3-Methyl-2-cyclopenten-1-one (CAS Registration No.: 2758-18-1):

[0382]

Chemistry 26

[0383]

[0384] ·γ-Butyrolactone (CAS Registration No.: 96-48-0):

[0385]

Chemistry 27

[0386]

[0387] ·2-Methyltetrahydrofuran-3-one (CAS Registration No.: 3188-00-9):

[0388]

Chemistry 28

[0389]

[0390] • α-Angelactone (CAS Registration No.: 591-12-8):

[0391]

Chemistry 29

[0392]

[0393] • Ethylcyclopentenolone (CAS Registration No.: 21835-01-8):

[0394]

Transformation 30

[0395]

[0396] ·3-Methyl-1,2-cyclohexanedione (CAS Registration No.: 3008-43-3):

[0397]

Chemistry 31

[0398]

[0399] • Maltol (CAS Registration No.: 118-71-8):

[0400]

Chemistry 32

[0401]

[0402] Tetrahydro-2H-pyran-3-one (CAS Registration No.: 23462-75-1):

[0403]

Transformation 33

[0404]

[0405] ·2,5-Cyclohexadien-1-one (CAS Registration No.: 5664-33-5):

[0406]

Transformation 34

[0407]

[0408] ·4-Methyl-2-pyrrolidone (CAS registration number: 2996-58-9, case where the tertiary carbon is in the S configuration; 31551-66-3, case where the tertiary carbon is in the R configuration; 260061-31-2):

[0409]

Chemistry 35

[0410]

[0411] ·2-Methyl-2,4-cyclopentadien-1-one (CAS Registration No.: 94618-71-0):

[0412]

Transformation 36

[0413]

[0414] ·4-Ethylpiperidin-2-one (CAS Registration No.: 50549-26-3):

[0415]

Chemistry 37

[0416]

[0417] ·1-Methylpiperidin-3-one (CAS Registration No.: 5519-50-6):

[0418]

Transformation 38

[0419]

[0420] Tetrahydro-3-methylpyran-2-one (CAS Registration No.: 10603-03-9):

[0421]

Chemistry 39

[0422]

[0423] ·γ-Dodecyl lactone (CAS registration number: 2305-05-7):

[0424]

Chemistry 40

[0425]

[0426] ·5-Dodecyl lactone (CAS Registry No.: 713-95-1):

[0427]

Chemistry 41

[0428]

[0429] ·2,5-Dimethyl-4-methoxy-3(2H)-furanone (CAS Registration No.: 4077-47-8):

[0430]

Chemistry 42

[0431]

[0432] • D-erythro-hex-2-enoic acid γ-lactone (D-isoascorbic acid) (CAS Registration No.: 89-65-6):

[0433]

Chemistry 43

[0434]

[0435] ·4-Acetoxy-2,5-dimethyl-3(2H)-furanone (CAS Registration No.: 4166-20-5):

[0436]

Chemistry 44

[0437]

[0438] ·Methyl 3-oxo-2-pentyl-1-cyclopentaacetate (CAS Registration No.: 24851-98-7):

[0439]

Chemistry 45

[0440]

[0441] ·4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-one (CAS Registration No.: 28664-35-9):

[0442]

Chemistry 46

[0443]

[0444] ·3,4-Dimethyl-1,2-cyclopentanedione (CAS Registration No.: 13494-06-9):

[0445]

Chemistry 47

[0446]

[0447] • D-Camphor (CAS Registration No.: 464-49-3):

[0448]

Chemistry 48

[0449]

[0450] ·3,4-Dihydro-2H-1-benzopyran-2-one (CAS Registration No.: 119-84-6):

[0451]

Chemistry 49

[0452]

[0453] ·(5R)-2-methyl-5-(1-methylvinyl)-2-cyclohexen-1-one (CAS Registration No.: 6485-40-1):

[0454] [Transformation 50]

[0455]

[0456] ·3-Propanedyl-1(3H)-isobenzofuranone (CAS Registration No.: 17369-59-4):

[0457]

Chemistry 51

[0458]

[0459] ·3,5,5-Trimethyl-2-cyclohexen-1-one (CAS Registration No.: 78-59-1):

[0460]

Chemistry 52

[0461]

[0462] Among them, based on the premise of effectively enhancing the oral coverage sensation, methylcyclopentenolone, γ-butyrolactone, 2-methyltetrahydrofuran-3-one, α-angelicolactone, maltol, 3-methyl-1,2-cyclohexanedione, γ-dodecanolide, 5-dodecanolide, 4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one, and D-camphor are preferred, with methylcyclopentenolone being particularly preferred.

[0463] There are no particular restrictions on the manufacturing method of (A), and substances manufactured by methods known to them (such as chemical synthesis, enzymatic methods, fermentation methods, extraction methods, etc.) or based on these methods can be used. For example, methylcyclopentenolone analogues can be obtained from plants such as coffee beans (MA. Gianturco, AS. Giammarino, R. G. Pitcher, Tetrahedron 19 2051 (1963)), high-temperature treatment of wood (J. Meyerfeld, Chem. Ztg. 36549 (1912)) or hot alkali treatment (T. Enkvist, B. Alfredsson, M. Merikallio, P. Paakonen, O. Jarrela, Acta. Chem. Scand. 8 51 (1954)), and heat treatment of sugars (International Publication No. 2014 / 157381; K. Heyns, R. Stute & H. Paulsen, Carbohydrate Res., 2, 132 (1966); R. R. Johnson, E. D. Alford & G. W. Kinzer, J. Agr. Food Chem., 17, 22 (1969); Shimizu Yasuo, Matsuto Shigeki, Mizunuma Yasuyuki, Okada Ikunosuke, Food Science (Food Science), 17, 385, 391, 397 (1970) etc., can be obtained or can be obtained by methods based on this, (A) commercially available products can be used.

[0464] [Ingredient (B)]

[0465] In this invention, β-caryophyllene oxide used as (B) is represented by the following formula, whose CAS registration number is 1139-30-6.

[0466]

Chemistry 53

[0467]

[0468] There are no particular restrictions on the manufacturing method of (B), and substances manufactured by methods known to them (such as chemical synthesis, enzymatic methods, fermentation methods, extraction methods, etc.) or methods based on those methods can be used. (B) Commercially available products can also be used.

[0469] [Ingredient (C)]

[0470] In this invention, the compound represented by general formula (II) used as (C) is sometimes referred to as "compound (II)" in this specification. Hereinafter, the groups of general formula (II) will be described.

[0471] In this specification, "acyl group having 1 to 6 carbon atoms" can be linear or branched, but linear is preferred. The acyl group can be saturated or contain unsaturated bonds. Specific examples of acyl groups having 1 to 6 carbon atoms include formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, neovaleryl, and hexanoyl.

[0472] In this specification, "acyloxy group having 1 to 6 carbon atoms" can be linear or branched, but linear is preferred. The acyloxy group can be saturated or contain unsaturated bonds. Specific examples of acyloxy groups having 1 to 6 carbon atoms include formyloxy, acetyloxy, propionyloxy, butyryloxy, isobutyryloxy, valeryloxy, isovaleryloxy, neovaleryloxy, and hexanoyloxy.

[0473] In this specification, "alkylene with 1 to 6 carbon atoms" can be linear or branched, but linear is preferred. Specific examples of alkylene with 1 to 6 carbon atoms include methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, etc.

[0474] R in general formula (II) 3 It represents an acyl, hydroxyl, pyrrole, or acyloxy group with 1 to 6 carbon atoms.

[0475] As R 3 Specific examples of "acyl groups having 1 to 6 carbon atoms" include formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, neovaleryl, and hexanoyl, with formyl, acetyl, propionyl, propionyl, butyryl, and isobutyryl being preferred, more preferably formyl, acetyl, and propionyl, and particularly preferably formyl and acetyl. The number of carbon atoms in this acyl group is preferably 1 to 4.

[0476] As R 3 Specific examples of "acyloxy group having 1 to 6 carbon atoms" include formyloxy, acetoxy, propionyloxy, butyryloxy, isobutyryloxy, valeryloxy, isovaleryloxy, neovaleryloxy, and hexanoyloxy, with formyloxy, acetoxy, propionyloxy, butyryloxy, and isobutyryloxy being preferred, more preferably formyloxy, acetoxy, and propionyloxy, and particularly preferably propionyloxy. The number of carbon atoms in this acyloxy group is preferably 1 to 4.

[0477] In general formula (II) R 3 Preferably, it is an acyl, hydroxyl, pyrrole or acyloxy group having 1 to 4 carbon atoms, more preferably formyl, acetyl, hydroxyl, pyrrole or propionyloxy group, and particularly preferably formyl or acetyl.

[0478] In general formula (II), Z represents a single bond or an alkylene group having 1 to 6 carbon atoms.

[0479] Specific examples of "alkylene groups having 1 to 6 carbon atoms" in Z include methylene, ethylene, trimethylene, tetramethylene, pentamethylene, and hexamethylene, with methylene, ethylene, trimethylene, and tetramethylene being preferred, methylene and ethylene being more preferred, and methylene being particularly preferred. The number of carbon atoms in this alkylene group is preferably 1 to 4.

[0480] In general formula (II), Z is preferably a single bond or an alkylene group having 1 to 4 carbon atoms, more preferably a single bond or a methylene group.

[0481] As one embodiment, in compound (II), R is preferred. 3 It is an acyl group with 1 to 6 carbon atoms, and Z is a single bond; more preferably R 3 It is an acyl group with 1 to 4 carbon atoms, and Z is a single bond; R is particularly preferred. 3 It is a formyl or acetyl group, and Z is a single bond.

[0482] As another embodiment, in compound (II), R is preferred. 3 Z is a hydroxyl, pyrrole, or acyloxy group having 1 to 6 carbon atoms, and Z is an alkylene group having 1 to 6 carbon atoms; more preferably, R 3 Z is a hydroxyl, pyrrole, or acyloxy group having 1 to 4 carbon atoms, and Z is an alkylene group having 1 to 4 carbon atoms; R is particularly preferred. 3 Z represents hydroxyl, pyrrole, or propionyloxy, and Z represents methylene.

[0483] R in general formula (II) 4 Indicates a substituent. R 4The substituents are not particularly limited, but examples include alkyl groups with 1 to 6 carbon atoms (e.g., methyl, ethyl, propyl, isopropyl, butyl, isobutyl, etc.), cycloalkyl groups with 3 to 8 carbon atoms (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, etc.), alkenyl groups with 2 to 6 carbon atoms (e.g., vinyl, 1-propynyl, 2-propynyl, 1-butenyl, 2-butenyl, 3-butenyl, etc.), and alkynyl groups with 2 to 6 carbon atoms (e.g., ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, etc.), and carbon atoms... Acyl groups having 1 to 6 carbon atoms (e.g., formyl, acetyl, propionyl, butyryl, isobutyryl, etc.), alkoxy groups having 1 to 6 carbon atoms (e.g., methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, etc.), and hydroxyalkyl groups having 1 to 6 carbon atoms (e.g., hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, etc.), preferably alkyl groups having 1 to 6 carbon atoms or hydroxyalkyl groups having 1 to 6 carbon atoms, more preferably alkyl groups having 1 to 4 carbon atoms or hydroxyalkyl groups having 1 to 4 carbon atoms, and particularly preferably methyl or hydroxymethyl.

[0484] In general formula (II), m represents an integer from 0 to 3. m preferably represents an integer from 0 to 2, and more preferably represents 0 or 1.

[0485] As one implementation, if m in general formula (II) is 2 or 3, then multiple R 4 They can be the same or different.

[0486] The preferred formula (II) consists of "R" 3 -Z- group and R 4 The -” indicates that the groups are different.

[0487] The following are suitable compounds (II).

[0488] [Compound (II-A)]

[0489] Compound (II): R 3 It is a formyl group, acetyl group, hydroxyl group, pyrrole group, or propionyloxy group;

[0490] Z represents a single bond or a methylene group;

[0491] R 4 Substituents (preferably alkyl groups having 1 to 6 carbon atoms or hydroxyalkyl groups having 1 to 6 carbon atoms);

[0492] m represents an integer from 0 to 3.

[0493] [Compound (II-B)]

[0494] Compound (II): R 3It is a formyl group, acetyl group, hydroxyl group, pyrrole group, or propionyloxy group;

[0495] Z represents a single bond or a methylene group;

[0496] R 4 Substituents (preferably alkyl groups having 1 to 6 carbon atoms or hydroxyalkyl groups having 1 to 6 carbon atoms);

[0497] m represents 0 or 1.

[0498] [Compound (II-C)]

[0499] Compound (II): R 3 It is an acyl or hydroxyl group with 1 to 6 carbon atoms;

[0500] Z is a single bond or an alkylene group having 1 to 6 carbon atoms;

[0501] R 4 Substituents (preferably alkyl groups with 1 to 6 carbon atoms or hydroxyalkyl groups with 1 to 6 carbon atoms);

[0502] m represents an integer from 0 to 3.

[0503] [Compound (II-D)]

[0504] Compound (II): R 3 It is a formyl group, an acetyl group, or a hydroxyl group;

[0505] Z represents a single bond or a methylene group;

[0506] R 4 Substituents (preferably alkyl groups having 1 to 6 carbon atoms or hydroxyalkyl groups having 1 to 6 carbon atoms);

[0507] m represents an integer from 0 to 3.

[0508] [Compound (II-E)]

[0509] Compound (II): R 3 It is a formyl group, an acetyl group, or a hydroxyl group;

[0510] Z represents a single bond or a methylene group;

[0511] R 4 Substituents (preferably alkyl groups having 1 to 6 carbon atoms or hydroxyalkyl groups having 1 to 6 carbon atoms);

[0512] m is 0 or 1.

[0513] [Compound (II-F)]

[0514] Compound (II): R 3 It is an acyl or pyrrole group with 1 to 6 carbon atoms;

[0515] Z is a single bond or an alkylene group having 1 to 6 carbon atoms;

[0516] R 4 Substituents (preferably alkyl groups having 1 to 6 carbon atoms or hydroxyalkyl groups having 1 to 6 carbon atoms);

[0517] m represents an integer from 0 to 3.

[0518] [Compound (II-G)]

[0519] Compound (II): R 3 It is a formyl group, an acetyl group, or a pyrrole group;

[0520] Z represents a single bond or a methylene group;

[0521] R 4 Substituents (preferably alkyl groups having 1 to 6 carbon atoms or hydroxyalkyl groups having 1 to 6 carbon atoms);

[0522] m is an integer from 0 to 3 (preferably 0 or 1).

[0523] [Compound (II-H)]

[0524] Compound (II): R 3 It is a formyl group, an acetyl group, or a pyrrole group;

[0525] Z represents a single bond or a methylene group;

[0526] R 4 Substituents (preferably alkyl groups having 1 to 6 carbon atoms or hydroxyalkyl groups having 1 to 6 carbon atoms);

[0527] m represents 0 or 1.

[0528] [Compound (II-I)]

[0529] Compound (II): R 3 It is an acyl group or an acyloxy group with 1 to 6 carbon atoms; Z is a single bond or an alkylene group with 1 to 6 carbon atoms;

[0530] R 4 Substituents (preferably alkyl groups having 1 to 6 carbon atoms or hydroxyalkyl groups having 1 to 6 carbon atoms);

[0531] m represents an integer from 0 to 3.

[0532] [Compound (II-J)]

[0533] Compound (II): R 3 It can be formyl, acetyl, or propionyloxy;

[0534] Z represents a single bond or a methylene group;

[0535] R 4 Substituents (preferably alkyl groups having 1 to 6 carbon atoms or hydroxyalkyl groups having 1 to 6 carbon atoms);

[0536] m represents an integer from 0 to 3 (preferably 0 or 1).

[0537] [Compound (II-K)]

[0538] Compound (II): R 3 It can be formyl, acetyl, or propionyloxy;

[0539] Z represents a single bond or a methylene group;

[0540] R 4 Substituents (preferably alkyl groups with 1 to 6 carbon atoms or hydroxyalkyl groups with 1 to 6 carbon atoms);

[0541] m represents 0 or 1.

[0542] Specific examples of preferred compound (II) include the following substances.

[0543] • Furfural (CAS Registration No.: 98-01-1):

[0544]

Chemistry 54

[0545]

[0546] ·2-Acetylfuran (CAS Registration No.: 1192-62-7):

[0547]

Transformation 55

[0548]

[0549] ·2-Acetyl-5-methylfuran (CAS Registration No.: 1193-79-9):

[0550]

Transformation 56

[0551]

[0552] ·3-Acetyl-2,5-dimethylfuran (CAS Registration No.: 10599-70-9):

[0553]

Chemistry 57

[0554]

[0555] • Furfuryl alcohol (CAS registration number: 98-00-0):

[0556]

Chemistry 58

[0557]

[0558] ·1-Furfurylpyrrole (CAS Registration No.: 1438-94-4):

[0559]

Chemistry 59

[0560]

[0561] • Furfural propionate (CAS registration number: 623-19-8):

[0562]

Transformation 60

[0563]

[0564] ·5-Methylfurfural (CAS Registration No.: 620-02-0):

[0565]

Chemistry 61

[0566]

[0567] ·5-(hydroxymethyl)furfural (CAS registration number: 67-47-0):

[0568]

Transformation 62

[0569]

[0570] Among them, furfural is preferred because it can effectively enhance the oral cavity's sense of coverage.

[0571] There are no particular restrictions on the manufacturing method of (C), and substances manufactured by methods known to them (such as chemical synthesis, enzymatic methods, fermentation methods, extraction methods, etc.) or methods based on these can be used. (C) can also use commercially available products.

[0572] As one implementation, (A), (B), and (C) can be chemically synthesized products prepared by chemical synthesis, or isolated products extracted and purified from materials containing at least one compound selected from (A), (B), and (C). Examples of materials containing at least one of (A), (B), and (C) include natural products such as agricultural, livestock, and aquatic products (e.g., maple, walnut, black pepper, white pepper, Sichuan pepper, cumin, pine, lemon balm, patchouli, artemisia, lemongrass, sage, corn cob, wild oats, wheat bran, etc.); fermentation products such as culture media and cell bodies obtained from culturing microorganisms; and their processed products (e.g., fumigants, caramel sauce, wine, sugarcane products, brown sugar, sambal sugar, molasses, coffee beans, coffee, spice extracts, etc.).

[0573] In this invention, in addition to chemically synthesized or isolated products of (A), (B), and (C), materials containing at least one compound selected from (A), (B), and (C) can be used directly, or used after purification to the desired extent. In this invention, the components of (A), (B), and (C) in materials containing at least one compound selected from (A), (B), and (C) are measured by a gas chromatography-mass spectrometry (GC-MS) or similar method.

[0574] The composition of the present invention contains at least two compounds selected from the group consisting of (A), (B) and (C), which are any one of (i) to (xviii) below.

[0575] (i) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfural (preferably all three compounds).

[0576] (ii) At least two compounds selected from the group consisting of (A) γ-butyrolactone, (B) β-caryophyllene oxide and (C) furfural (preferably all three compounds).

[0577] (iii) At least two compounds selected from the group consisting of (A) 2-methyltetrahydrofuran-3-one, (B) β-caryophyllene oxide and (C) furfural (preferably all three compounds).

[0578] (iv) At least two compounds selected from the group consisting of (A) α-angelicin, (B) β-caryophyllene oxide and (C) furfural (preferably all three compounds).

[0579] (v) Select at least two compounds from the group consisting of (A) maltol, (B) β-caryophyllene oxide and (C) furfural (preferably all three compounds).

[0580] (vi) Select at least two compounds from the group consisting of (A) 3-methyl-1,2-cyclohexanedione, (B) β-caryophyllene oxide and (C) furfural (preferably all three compounds).

[0581] (vii) Select at least two compounds from the group consisting of (A) γ-dodecyl lactone, (B) β-caryophyllene oxide and (C) furfural (preferably all three compounds).

[0582] (viii) Select at least two compounds from the group consisting of (A) 5-dodecanolide, (B) β-caryophyllene oxide and (C) furfural (preferably all three compounds).

[0583] (ix) At least two compounds selected from the group consisting of (A) 4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one, (B) β-caryophyllene oxide and (C) furfural (preferably all three compounds).

[0584] (x) Select at least two compounds from the group consisting of (A) D-camphor, (B) β-caryophyllene oxide and (C) furfural (preferably all three compounds).

[0585] (xi) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 2-acetylfuran (preferably all three compounds).

[0586] (xii) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 2-acetyl-5-methylfuran (preferably all three compounds).

[0587] (xiii) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 3-acetyl-2,5-dimethylfuran (preferably all three compounds).

[0588] (xiv) Select at least two compounds (preferably all three) from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfuryl alcohol.

[0589] (xv) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 1-furfurylpyrrole (preferably all three compounds).

[0590] (xvi) Select at least two compounds from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfuryl propionate (preferably all three compounds).

[0591] (xvii) Select at least two compounds from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 5-methylfurfural (preferably all three compounds).

[0592] (xviii) At least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) 5-(hydroxymethyl)furfural (preferably all three compounds).

[0593] The compositions of the present invention may contain at least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfural. Alternatively, the compositions of the present invention may be compositions containing (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfural.

[0594] When the composition of the present invention contains at least (A), the content of (A) in the composition of the present invention is generally 0.001% by weight or more, preferably 0.01% by weight or more, more preferably 0.1% by weight or more, more preferably 1% by weight or more, and particularly preferably 10% by weight or more. Furthermore, when the composition of the present invention contains at least (A), the content of (A) in the composition of the present invention is generally 99% by weight or less, preferably 95% by weight or less, and more preferably 90% by weight or less. As an embodiment, when the composition of the present invention contains at least (A), the content of (A) in the composition of the present invention is generally 0.001 to 99% by weight, preferably 0.01 to 95% by weight, and more preferably 0.1 to 90% by weight.

[0595] When the composition of the present invention contains at least (B), the content of (B) in the composition of the present invention is generally 0.001% by weight or more, preferably 0.01% by weight or more, more preferably 0.1% by weight or more, further preferably 1% by weight or more, and particularly preferably 10% by weight or more. Furthermore, when the composition of the present invention contains at least (B), the content of (B) in the composition of the present invention is generally 99% by weight or less, preferably 95% by weight or less, and more preferably 90% by weight or less. As an embodiment, when the composition of the present invention contains at least (B), the content of (B) in the composition of the present invention is generally 0.001 to 99% by weight, preferably 0.01 to 95% by weight, and more preferably 0.1 to 90% by weight.

[0596] When the composition of the present invention contains at least (C), the content of (C) in the composition of the present invention is generally 0.001% by weight or more, preferably 0.01% by weight or more, more preferably 0.1% by weight or more, more preferably 1% by weight or more, and particularly preferably 10% by weight or more. Furthermore, when the composition of the present invention contains at least (C), the content of (C) in the composition of the present invention is generally 99% by weight or less, preferably 95% by weight or less, and more preferably 90% by weight or less. In the case where the composition of the present invention contains at least (C), as an embodiment, the content of (C) in the composition of the present invention is generally 0.001 to 99% by weight, preferably 0.01 to 95% by weight, and more preferably 0.1 to 90% by weight.

[0597] When the composition of the present invention contains at least (A) and (B), the weight ratio (A:B) of the content of (A) to the content of (B) in the composition of the present invention is preferably 1:0.001 to 1000, more preferably 1:0.5 to 1000, even more preferably 1:1 to 500, even more preferably 1:10 to 250, particularly preferably 1:25 to 100, and most preferably 1:30 to 75, based on the ability to particularly effectively enhance the oral coverage sensation.

[0598] When the composition of the present invention contains at least (A) and (C), the weight ratio (A:C) of the content of (A) to the content of (C) in the composition of the present invention is preferably 1:0.001 to 1000, more preferably 1:0.5 to 1000, even more preferably 1:1 to 500, even more preferably 1:10 to 250, particularly preferably 1:25 to 100, and most preferably 1:30 to 75, based on the ability to particularly effectively enhance the oral coverage sensation.

[0599] When the composition of the present invention contains at least (B) and (C), the weight ratio (B:C) of the content of (B) to the content of (C) in the composition of the present invention is preferably 1:0.001 to 1000, more preferably 1:0.01 to 100, further preferably 1:0.02 to 50, particularly preferably 1:0.3 to 3, and most preferably 1:0.5 to 2, based on the ability to particularly enhance the oral coverage sensation.

[0600] As one embodiment, the composition of the present invention may contain all of (A), (B) and (C).

[0601] There are no particular limitations on the form of the compositions of the present invention. Examples include solid (including powder, granules, etc.), liquid (including slurry, etc.), gel, paste, etc.

[0602] The compositions of the present invention may contain only two compounds selected from (A), (B) and (C), but may also contain, in addition to these, conventional base agents corresponding to the morphology of the compositions of the present invention.

[0603] Examples of base agents used in the liquid form of the compositions of the present invention include water, ethanol, glycerin, propylene glycol, and various animal and vegetable oils.

[0604] Examples of base agents used in the form of the compositions of the present invention when they are in solid form include various sugars such as starch, dextrin, cyclodextrin, sucrose and glucose, proteins, peptides, salts, solid fats, silicon dioxide and mixtures thereof, yeast cells, and various powder extracts.

[0605] The compositions of the present invention may contain, in addition to at least two compounds selected from (A), (B) and (C), such as excipients, pH adjusters, antioxidants, thickeners and stabilizers, sweeteners (e.g., sugars), acidulants, spices, colorants, etc., provided that they do not impair the purpose of the present invention.

[0606] The compositions of the present invention can be manufactured using methods conventional in the field of food flavorings. For example, the compositions of the present invention can be subjected to concentration, drying, decolorization, etc., alone or in combination.

[0607] The compositions of the present invention can be added to food products. Adding the compositions of the present invention to food products enhances the oral coating sensation. Furthermore, adding the compositions of the present invention to food products enhances the oral coating sensation without imparting any off-flavors. Therefore, the compositions of the present invention are preferably used as flavoring compositions for enhancing the oral coating sensation of food products.

[0608] In this invention, the term "oral covering sensation" refers to the distinct sensation felt when the oral cavity contains oils, oily solutions, or food, including the sensation of the oral cavity being covered by a thin film, the sensation of the oral cavity being covered by oil or an oily film, the silky sensation felt in the oral cavity, and the thick, oily sensation spreading throughout the oral cavity. "Enhancement" of the oral covering sensation refers to an enhancement of at least one of the above sensations. The presence and degree of the oral covering sensation can be evaluated based on the sensory evaluation of an expert evaluator.

[0609] In this invention, "off-flavor" refers to an unpleasant flavor (taste, aroma) that is not normally perceptible in food. Examples of ways to impart off-flavors to food include adding ingredients not normally present in the food, resulting in a specific undesirable taste or aroma (e.g., a chemical taste), or changing the original taste or aroma of the food into an undesirable one. The presence and degree of off-flavors can be evaluated through sensory assessment by expert evaluators.

[0610] In addition, in this invention, "food" is a broad concept that includes substances that can be ingested orally, such as beverages, seasonings, food additives, etc.

[0611] Food products containing the compositions of the present invention can be provided (sold, distributed) in a state that is already suitable for consumption, or they can be provided in a state that requires prescribed processing or cooking to make them suitable for consumption. For example, food products containing the compositions of the present invention can be provided as concentrates that require dilution with water or the like to make them suitable for consumption.

[0612] Foods to which the composition of this invention can be added are any foods for which a mouth-covering sensation is desired, with no particular limitations. For example, oils (such as vegetable oils, animal oils, etc.), mayonnaise, soups (such as ramen soup, clear soup, chicken bone soup, etc.), sauces, curry, wrapped foods (such as dumplings, shumai, wontons, steamed buns, xiaolongbao, ravioli, spring rolls, etc.), rice (such as fried rice, paella, pilaf, etc.), and fried foods (such as croquettes, minced meat patties, etc.). Foods containing oil include: cutlets, hamburgers, meatballs, sausages, pastries, chocolate, cookies, bread, dairy products containing fat (e.g., raw milk, cow's milk, low-fat milk, cream, butter, margarine, spreadable butter, cheese, yogurt, etc.), gratin, beverages containing oil, and noodles containing oil (e.g., fried noodles, dried noodles, etc.); oil-free sauces, non-fat dairy products (e.g., non-fat milk, skim milk powder, non-fatty acid milk, etc.), non-fat beverages (e.g., coffee drinks, etc.), and non-fat noodles (e.g., udon noodles, soba noodles, non-fat dried noodles, non-fried noodles, raw noodles, pasta, sheet noodles, frozen noodles, etc.). Here, "foods containing oil" can also refer to foods containing only oil; that is, foods containing oil can be oil itself.

[0613] The compositions of the present invention can significantly enhance the oral enveloping sensation when oils are present in the mouth, and are therefore preferably added to oily foods for use; that is, the compositions of the present invention are preferably used in oily foods.

[0614] The oils contained in the oil-containing foods containing the compositions of the present invention are not particularly limited as long as they are edible. For example, vegetable oils such as rapeseed oil, corn oil, soybean oil, sesame oil, rice bran oil, rice bran oil, safflower oil, coconut oil, palm oil, palm kernel oil, sunflower oil, perilla oil, flaxseed oil, olive oil, grapeseed oil, and medium-chain triglyceride oils can be used; animal oils such as lard, tallow, chicken fat, mutton fat, horse fat, fish oil, whale oil, and milk fat can also be used. Additionally, transesterified oils obtained by transesterification of the above-mentioned oils, and solidified oils obtained by hydrogenation of the above-mentioned oils can also be used. The above-mentioned oils can be purified oils (e.g., salad oil). These oils can be used alone or in combination of two or more.

[0615] There is no particular limitation on the oil content in the oil-containing food in which the composition of the present invention can be used, but it is preferred to be 0.1 to 100% by weight, more preferably 0.5 to 100% by weight, so as to achieve a more significant effect.

[0616] The method and conditions for adding the composition of the present invention to food are not particularly limited, and can be appropriately set according to the form of the composition and the type of food. The timing of adding the composition of the present invention to food is not particularly limited, and it can be added at any time, for example, during the food manufacturing process, after the food is finished (just before consumption, during consumption, etc.). The composition of the present invention can also be added to the raw materials before food manufacturing.

[0617] When the composition of the present invention contains at least (A), it is preferable to add the food in a manner that, based on the premise that the composition of the present invention can effectively enhance the oral coverage without imparting an off-flavor to the food, the concentration of (A) in the food (sometimes referred to as "a" or "concentration a of (A)" in this specification) relative to the total weight of the food when consumed is within a specific range. Specifically, the concentration a of (A) in the food relative to the total weight of the food when consumed is preferably 0.05 ppb by weight or more, more preferably 0.1 ppb by weight or more, and particularly preferably 0.3 ppb by weight or more. In addition, the concentration a of (A) in the food relative to the total weight of the food when consumed is preferably 5000 ppb by weight or less, more preferably 3000 ppb by weight or less, and particularly preferably 1500 ppb by weight or less. As an embodiment, the concentration a of (A) in the food relative to the total weight of the food when consumed is preferably 0.05 to 5000 ppb by weight, more preferably 0.1 to 3000 ppb by weight, and particularly preferably 0.3 to 1500 ppb by weight.

[0618] When the composition of the present invention contains at least (B), it is preferable to add (B) to the food in a manner that effectively enhances the oral coverage without imparting an off-flavor to the food, based on the premise that the composition of the present invention can effectively enhance the oral coverage without imparting an off-flavor to the food. Specifically, the concentration of (B) in the food, b, relative to the total weight of the food when consumed, is preferably 0.1 ppb or more by weight, more preferably 0.5 ppb or more by weight, and particularly preferably 1 ppb or more by weight. In addition, the concentration of (B) in the food, b, relative to the total weight of the food when consumed, is preferably 50,000 ppb or less by weight, more preferably 10,000 ppb or less by weight, further preferably 7,000 ppb or less by weight, and particularly preferably 6,000 ppb or less by weight. As an embodiment, the concentration of (B) in the food, b, relative to the total weight of the food when consumed, is preferably 0.1 to 50,000 ppb by weight, more preferably 0.5 to 10,000 ppb by weight, and particularly preferably 1 to 6,000 ppb by weight.

[0619] When the composition of the present invention contains at least (C), it is preferable to add the (C) concentration (sometimes referred to as "c" or "concentration c of (C)" in this specification) to the food in a specific range relative to the total weight of the food when it is consumed, based on the premise that the composition of the present invention can effectively enhance the oral coverage without imparting an off-flavor to the food. Specifically, the (C) concentration c in the food is preferably 0.1 ppb or more by weight relative to the total weight of the food when it is consumed, more preferably 0.5 ppb or more by weight, and particularly preferably 1 ppb or more by weight. In addition, the (C) concentration c in the food is preferably 50,000 ppb or less by weight relative to the total weight of the food when it is consumed, more preferably 10,000 ppb or less by weight, further preferably 7,000 ppb or less by weight, and particularly preferably 6,000 ppb or less by weight. As an alternative, the (C) concentration c in the food, relative to the total weight of the food when it is consumed, is preferably 0.1 to 50,000 ppb by weight, more preferably 0.5 to 10,000 ppb by weight, and particularly preferably 1 to 6,000 ppb by weight.

[0620] When the composition of the present invention contains at least (A) and (B), the composition based on the present invention can particularly effectively enhance the oral coverage sensation, preferably by adding it to the food in such a way that the weight ratio (a:b) of the concentration a of (A) to the concentration b of (B) in the food is within a specific range. Specifically, the weight ratio (a:b) of the concentration a of (A) to the concentration b of (B) in the food is preferably 1:0.001 to 1000, more preferably 1:0.5 to 1000, further preferably 1:1 to 500, even more preferably 1:10 to 250, particularly preferably 1:25 to 100, and most preferably 1:30 to 75.

[0621] When the composition of the present invention contains at least (A) and (C), the composition of the present invention can particularly effectively enhance the oral coverage sensation, preferably by adding it to the food in a manner that makes the weight ratio (a:c) of the concentration a of (A) to the concentration c of (C) in the food within a specific range. Specifically, the weight ratio (a:c) of the concentration a of (A) to the concentration c of (C) in the food is preferably 1:0.001 to 1000, more preferably 1:0.5 to 1000, further preferably 1:1 to 500, even more preferably 1:10 to 250, particularly preferably 1:25 to 100, and most preferably 1:30 to 75.

[0622] When the composition of the present invention contains at least (B) and (C), the composition of the present invention can particularly effectively enhance the oral coverage sensation, preferably by adding it to the food in such a way that the weight ratio (b:c) of the concentration b of (B) to the concentration c of (C) in the food is within a specific range. Specifically, the weight ratio (b:c) of the concentration b of (B) to the concentration c of (C) in the food is preferably 1:0.001 to 1000, more preferably 1:0.01 to 100, further preferably 1:0.02 to 50, particularly preferably 1:0.3 to 3, and most preferably 1:0.5 to 2.

[0623] This invention provides a food product (sometimes referred to simply as "the food product of this invention") containing at least two compounds selected from the group consisting of (A) a compound represented by general formula (I), (B) β-caryophyllene oxide, and (C) a compound represented by general formula (II):

[0624]

Transformation 63

[0625]

[0626] [In the formula, ring A is a 5- or 6-membered saturated or unsaturated carbon ring, or a 5- or 6-membered saturated or unsaturated oxygen- or nitrogen-containing heterocycle.]

[0627] R 1 The radical can be an oxo group, a hydroxyl group, an alkoxy group with 1 to 4 carbon atoms, an acyloxy group with 1 to 4 carbon atoms, or a hydrocarbon group or hydrogen atom with 1 to 8 carbon atoms that may have substituents. 1 When the hydrocarbon group having 1 to 8 carbon atoms that can have substituents is a hydrocarbon group, the carbon atoms in the hydrocarbon group can bond with the carbon atoms of ring A to form a cross-linked structure or a saturated or unsaturated ring structure;

[0628] R 2 It consists of a hydrocarbon group, a hydroxyl group, or a hydrogen atom with 1 to 8 carbon atoms;

[0629] [n represents an integer from 1 to 3]

[0630]

Chemistry 64

[0631]

[0632] [In the formula, R] 3 It is an acyl group, hydroxyl group, pyrrole group, or acyloxy group with 1 to 6 carbon atoms;

[0633] Z is a single bond or an alkylene group having 1 to 6 carbon atoms;

[0634] R 4 For substituents;

[0635] m represents an integer from 0 to 3.

[0636] The (A), (B) and (C) that may be contained in the food of the present invention are the same as those that may be contained in the composition of the present invention, and the preferred embodiments are also the same.

[0637] The food products of the present invention contain at least two compounds selected from the group consisting of (A), (B) and (C), which can be any one of (i) to (xviii) above.

[0638] The food products of the present invention may be foods containing at least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfural. Alternatively, the food products of the present invention may be foods containing (A) methylcyclopentenolone, (B) β-caryophyllene oxide and (C) furfural.

[0639] When the food of the present invention contains at least (A), the concentration of (A) in the food of the present invention is preferably within a specific range relative to the total weight of the food when consumed, based on the fact that the composition of the present invention can effectively enhance the oral coverage without imparting an off-flavor to the food. Specifically, the concentration of (A) in the food of the present invention can be set in the same way as the concentration a of (A) described above, and the preferred range is also the same.

[0640] When the food of the present invention contains at least (B), the concentration of (B) in the food of the present invention is preferably within a specific range relative to the total weight of the food when consumed, based on the fact that the composition of the present invention can effectively enhance the oral coverage without imparting an off-flavor to the food. Specifically, the concentration of (B) in the food of the present invention can be set in the same way as the concentration b of (B) described above, and the preferred range is also the same.

[0641] When the food of the present invention contains at least (C), the concentration of (C) in the food of the present invention is preferably within a specific range relative to the total weight of the food when consumed, based on the fact that the composition of the present invention can effectively enhance the oral coverage without imparting an off-flavor to the food. Specifically, the concentration of (C) in the food of the present invention can be set in the same way as the concentration c of (C) described above, and the preferred range is also the same.

[0642] When the food of the present invention contains at least (A) and (B), it is preferable that the weight ratio of the concentration of (A) to the concentration of (B) in the food of the present invention is within a specific range, based on the fact that it can particularly effectively enhance the oral coverage sensation. Specifically, the weight ratio of the concentration of (A) to the concentration of (B) in the food of the present invention can be set in the same way as the weight ratio (a:b) of the concentration a of (A) to the concentration b of (B) described above, and the preferred range is also the same.

[0643] When the food of the present invention contains at least (A) and (C), it is preferable that the weight ratio of the concentration of (A) to the concentration of (C) in the food of the present invention is within a specific range, based on the fact that it can particularly effectively enhance the oral coverage sensation. Specifically, the weight ratio of the concentration of (A) to the concentration of (C) in the food of the present invention can be set in the same way as the weight ratio (a:c) of the concentration of (A) a to the concentration of (C) c described above, and the preferred range is also the same.

[0644] When the food of the present invention contains at least (B) and (C), the weight ratio of the concentration of (B) to the concentration of (C) in the food of the present invention is preferably within a specific range, based on the fact that it can particularly effectively enhance the oral coverage sensation. Specifically, the weight ratio of the concentration of (B) to the concentration of (C) in the food of the present invention can be set in the same way as the weight ratio (b:c) of the concentration of (B) b to the concentration of (C) c described above, and the preferred range is also the same.

[0645] As one embodiment, the food of the present invention may be a food comprising all of (A), (B) and (C).

[0646] There are no particular limitations on the types of food products of the present invention, as long as they are foods that are desired to have a mouth-covering sensation. For example, the same foods as those exemplified as foods to which the composition of the present invention can be added can be given, and the same applies to preferred foods.

[0647] The food of the present invention is preferably a food that enhances the oral cavity coverage, more preferably a food that enhances the oral cavity coverage and has no odor.

[0648] As one embodiment, the food of the present invention may contain oil, that is, the food of the present invention may be a food containing oil. The food of the present invention may be an oil-containing food that enhances the oral coverage sensation, or it may be an oil-containing food that enhances the oral coverage sensation and has no odor.

[0649] When the food of the present invention contains oil (i.e., when the food of the present invention is a food containing oil), there are no particular restrictions on the type of oil contained in the food of the present invention as long as it is edible. For example, the same type of oil as that contained in a food containing oil in which the composition of the present invention can be used can be cited, and the preferred type of oil is also the same.

[0650] When the food of the present invention contains oil (i.e., when the food of the present invention is a food containing oil), the oil content in the food of the present invention is not particularly limited, but since it can exert a more definite effect, it is preferably 0.1 to 99.9% by weight, more preferably 0.5 to 99.5% by weight.

[0651] The method for manufacturing the food of the present invention (also referred to herein as "the preparation method of the present invention") includes adding at least two compounds selected from (A), (B) and (C).

[0652] The at least two compounds selected from the group consisting of (A), (B) and (C) added in the manufacturing method of the present invention can be any one of (i) to (xviii) above.

[0653] The manufacturing method of the present invention may include adding at least two compounds selected from the group consisting of (A) methylcyclopentenolone, (B) β-caryophyllene oxide, and (C) furfural. Alternatively, the manufacturing method of the present invention may include adding (A) methylcyclopentenolone, (B) β-caryophyllene oxide, and (C) furfural.

[0654] When the preparation method of the present invention includes adding at least (A), from the perspective of producing a food that can effectively enhance the oral coverage without imparting an off-flavor to the food, it is preferable that the addition of (A) is carried out in such a way that the concentration of (A) in the food is preferably within a specific range relative to the total weight of the food when consumed. Specifically, in the manufacturing method of the present invention, the concentration of (A) in the food can be set in the same way as the concentration a of (A) described above, and the preferred range is also the same.

[0655] When the preparation method of the present invention includes the addition of at least (B), from the perspective of producing a food that can effectively enhance the oral coverage without imparting an off-flavor to the food, it is preferable that the addition of (B) is carried out in such a way that the concentration of (B) in the food is preferably within a specific range relative to the total weight of the food when consumed. Specifically, in the manufacturing method of the present invention, the concentration of (B) in the food can be set in the same way as the concentration b of (B) described above, and the preferred range is also the same.

[0656] When the preparation method of the present invention includes the addition of at least (C), from the perspective of producing a food that can effectively enhance the oral coverage without imparting an off-flavor to the food, it is preferable that the addition of (C) is carried out in such a way that the concentration of (C) in the food is preferably within a specific range relative to the total weight of the food when consumed. Specifically, in the manufacturing method of the present invention, the concentration of (C) in the food can be set in the same way as the concentration c of (C) described above, and the preferred range is also the same.

[0657] When the preparation method of the present invention includes adding at least (A) and (B), from the perspective of producing a food that can effectively enhance the oral coverage without imparting an off-flavor to the food, the addition of (A) and (B) is preferably carried out in a manner where the weight ratio of the concentration of (A) to the concentration of (B) in the food is within a specific range. Specifically, in the manufacturing method of the present invention, the weight ratio of the concentration of (A) to the concentration of (B) in the food can be set in the same way as the weight ratio (a:b) of the concentration of (A) a to the concentration of (B) b described above, and the preferred range is also the same.

[0658] When the preparation method of the present invention includes adding at least (A) and (C), from the perspective of producing a food that can effectively enhance the oral coverage without imparting an off-flavor to the food, the addition of (A) and (C) is preferably carried out in a manner where the weight ratio of the concentration of (A) to the concentration of (C) in the food is within a specific range. Specifically, in the manufacturing method of the present invention, the weight ratio of the concentration of (A) to the concentration of (C) in the food can be set in the same way as the weight ratio (a:c) of the concentration of (A) a to the concentration of (C) c described above, and the preferred range is also the same.

[0659] When the preparation method of the present invention includes the addition of at least (B) and (C), from the perspective of producing a food that can effectively enhance the oral coverage without imparting an off-flavor to the food, the addition of (B) and (C) is preferably carried out in a manner where the weight ratio of the concentration of (B) to the concentration of (C) in the food is within a specific range. Specifically, in the manufacturing method of the present invention, the weight ratio of the concentration of (B) to the concentration of (C) in the food can be set in the same way as the weight ratio (b:c) of the concentration of (B) b to the concentration of (C) c described above, and the preferred range is also the same.

[0660] The manufacturing method of the present invention can add at least two compounds selected from (A), (B), and (C) individually, or these compounds can be premixed before addition to obtain a mixture. Alternatively, the addition of these compounds can also be carried out using the composition of the present invention described above. When at least two compounds selected from (A), (B), and (C) are added individually, there are no particular restrictions on the order and interval of addition. For example, when adding (A) and (B), (A) and (B) can be added in the order of (A) and (B) or in the reverse order, or (A) and (B) can be added simultaneously.

[0661] As one embodiment, the preparation method of the present invention can be any method that includes adding (A), (B) and (C).

[0662] In addition to adding at least two compounds selected from (A), (B), and (C), the production method of the present invention may appropriately include conventional processing steps and cooking steps in the production of food according to the type of food produced, etc.

[0663] The production method of the present invention is preferably a production method of food with enhanced oral coating feeling, and more preferably a production method of food with enhanced oral coating feeling and no off-flavor.

[0664] As an embodiment, the production method of the present invention is a production method of food containing oil and fat. The production method of the present invention may be a production method of oil-and-fat-containing food with enhanced oral coating feeling, and may also be a production method of oil-and-fat-containing food with enhanced oral coating feeling and no off-flavor.

[0665] The present invention provides a method for enhancing oral coating feeling (also simply referred to as "the enhancing method of the present invention" in this specification), which includes adding at least two compounds selected from the group consisting of (A) a compound represented by the general formula (I), (B) β-caryophyllene, and (C) a compound represented by the general formula (II) to food:

[0666]

Chemical formula 65

[0667]

[0668] 〔In the formula, ring A is a 5- or 6-membered saturated or unsaturated carbocyclic ring, or a 5- or 6-membered saturated or unsaturated heterocyclic ring containing oxygen or nitrogen;

[0669] R 1 is an oxo group, a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, an acyloxy group having 1 to 4 carbon atoms, a hydrocarbon group having 1 to 8 carbon atoms which may have substituents, or a hydrogen atom, and when R 1 is a hydrocarbon group having 1 to 8 carbon atoms which may have substituents, the carbon atoms in the hydrocarbon group may be bonded to the carbon atoms of ring A to form a crosslinked structure or a saturated or unsaturated ring structure;

[0670] R 2 is a hydrocarbon group having 1 to 8 carbon atoms, a hydroxyl group, or a hydrogen atom;

[0671] n represents an integer of 1 to 3〕,

[0672]

Chemical formula 66

[0673]

[0674] 〔In the formula, R 3 is an acyl group having 1 to 6 carbon atoms, a hydroxyl group, a pyrrolyl group, or an acyloxy group having 1 to 6 carbon atoms;

[0675] Z is a single bond or an alkylene group having 1 to 6 carbon atoms;

[0676] R 4 For substituents;

[0677] m represents an integer from 0 to 3.

[0678] The enhancement methods (A), (B), and (C) used in this invention are the same as those (A), (B), and (C) that can be included in the composition of this invention, and the preferred embodiments are also the same.

[0679] Unless otherwise specified, the enhancement method of the present invention can be implemented in the same way as the manufacturing method of the present invention described above, and the preferred method is also the same.

[0680] In the enhancement method of the present invention, the method and conditions for adding at least two compounds selected from (A), (B) and (C) are not particularly limited, and can be appropriately set according to the type of food to which they are added.

[0681] There is no particular limitation on the timing of adding at least two compounds selected from (A), (B), and (C) to the food; they can be added at any time, such as during the food manufacturing process and after the food is finished (e.g., just before the food is consumed, during the consumption process, etc.). At least two compounds selected from (A), (B), and (C) can be added to the food ingredients before the food is manufactured.

[0682] According to the enhancement method of the present invention, the oral envelopment sensation of food can be effectively enhanced. Furthermore, the enhancement method of the present invention can effectively improve the oral envelopment sensation without imparting any unpleasant odor to the food. The enhancement method of the present invention can be used to enhance the oral envelopment sensation of any food for which an oral envelopment sensation is desired; there are no particular limitations. For example, the same foods as those exemplified as foods to which the composition of the present invention can be added can be cited, and the same applies to preferred foods.

[0683] The enhancement method of the present invention can significantly enhance the oral enveloping sensation felt when the oral cavity contains oil, and is therefore preferably a method for enhancing the oral enveloping sensation of oily foods.

[0684] The invention is illustrated in more detail in the following embodiments, but the invention is not limited to these examples. Furthermore, when “%” or “ppb” is used in this specification, unless otherwise stated, it means “% by weight” or “ppb by weight”.

[0685]

Example

[0686] [Example 1]

[0687] <Positive and Negative Controls>

[0688] In the positive control (PC), commercially available mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "Pure Select (registered trademark) mayonnaise", fat content: 73%) was used, while the negative control (NC) used commercially available mayonnaise with less fat content compared to the positive control mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "Pure Select (registered trademark) KOKUUMA (registered trademark) reduced by 65% ​​calories", fat content: 23%).

[0689] <Preparation of Test Samples>

[0690] (Experimental Zones 1-1 to 1-39)

[0691] The test samples were prepared as follows: commercially available mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "Pure Select (registered trademark) KOKUUMA (registered trademark) 65% Calorie Reduction", fat content: 23%) used as the negative control above, with at least one compound selected from methylcyclopentenolone, β-caryophyllene oxide and furfural added to achieve the concentration of each compound in the food (mayonnaise) as shown in Tables 1 to 3 below (hereinafter, each test sample is also referred to as "sample of test area 1-1" to "sample of test area 1-39").

[0692] (Control Area 1)

[0693] In a commercially available mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "PureSelect KOKUUMA (registered trademark) Reduced 65% Calories", fat content: 23%) used as the negative control above, methylcyclopentenolone, caprylic acid and isovaleric acid were added to prepare a sample for control area 1, with the concentration of methylcyclopentenolone in the food (mayonnaise) being 100 ppb by weight, the concentration of caprylic acid being 200 ppb by weight, and the concentration of isovaleric acid being 100 ppb by weight.

[0694] <Sensory Evaluation>

[0695] The intensity of the oral envelopment sensation and the presence or absence of odor in the test samples were evaluated using sensory evaluation.

[0696] The evaluation of oral coverage was conducted as follows: Four professional evaluators consumed mayonnaise from the positive control, negative control, and test samples (samples from test areas 1-1 to 1-39 and control area 1). The positive control was set to "5.0 points," and the negative control to "0.0 points." Each test sample was scored on a scale of 0.1 points within the range of 0.0 to 5.0 (non-blinded). The scores from the four professional evaluators were averaged. A score of 1.0 or higher was considered to indicate an enhanced oral coverage effect. Furthermore, the four professional evaluators were trained beforehand to ensure consensus was reached on the degree of variation in oral coverage within 0.1-point increments.

[0697] In the evaluation of off-odors, four professional evaluators tasted each sample of mayonnaise and, based on the following criteria, determined through consultation whether or not off-odors (such as chemical smells or other tastes or odors not normally present in mayonnaise) were present. (Off-odor evaluation criteria)

[0698] ++: An odor is present.

[0699] +: Slight odor

[0700] - Odorless

[0701] The results are shown in Tables 1-3 below.

[0702] Table 1

[0703] Single component

[0704]

[0705] Table 2

[0706] <2 ingredients>

[0707]

[0708] Table 3

[0709] <3 ingredients>

[0710]

[0711] The results in Tables 1-3 show that the samples in test areas 1-20 to 1-39 of the present invention, which contained at least two compounds selected from methylcyclopentenolone, β-caryophyllene oxide, and furfural, all effectively enhanced the oral coverage sensation. Furthermore, these test samples had no odor.

[0712] Based on these results, it can be confirmed that adding at least two compounds selected from methylcyclopentenolone, β-caryophyllene oxide, and furfural to food can effectively enhance the oral envelopment without imparting any off-flavors to the food.

[0713] [Example 2]

[0714] The addition of at least one compound selected from methylcyclopentenolone, β-caryophyllene oxide, and furfural to coffee beverages prepared using instant coffee powder, and the evaluation of its effect on oral encapsulation sensory function.

[0715] Specifically, firstly, a coffee beverage was prepared using a hot water extract of roasted coffee beans, along with fast-drying instant coffee powder, non-dairy creamer, skim milk powder, sugar, and hot water, according to the formula described in Table 4 below. Commercially available non-dairy creamer, skim milk powder, and sugar were used. Next, at least one compound selected from methylcyclopentenolone, β-caryophyllene oxide, and furfural was added to the coffee beverage, and the concentration of each compound in the food (coffee beverage) was adjusted to the concentrations shown in Table 5 below. Test samples were prepared (hereinafter referred to as "samples in test areas 2-1" to "samples in test areas 2-8," respectively). The coffee beverage without any added compounds (negative control) was set to "0.0 points." Within the range of 0.0 to 5.0 points, three professional evaluators, through consultation, scored each test sample on a 0.5-point scale according to the following criteria, conducting a sensory evaluation. A score of 1.0 or higher was considered to indicate an enhanced oral coverage effect. In addition, for the three professional evaluators, they were trained in advance to reach a consensus on the degree to which the oral cavity coverage should change in order to make the score change by 0.5 points.

[0716] (Evaluation criteria for oral cavity coverage)

[0717] 5.0 points: Provides a good sense of coverage in the mouth.

[0718] 2.5 points: It provides a certain degree of oral coverage.

[0719] 1.0 point: Slight feeling of being covered in the mouth

[0720] Table 4

[0721] raw material Amount of compound (g) Instant coffee powder 0.7 non-dairy creamer 3.2 skim milk powder 0.3 granulated sugar 3.0 hot water 92.8 Total 100.0

[0722] Table 5

[0723]

[0724] As shown in Table 5, the samples in test areas 2-4 to 2-8 of the present invention, which contained at least two compounds selected from methylcyclopentenolone, β-caryophyllene oxide, and furfural, all effectively enhanced the oral coverage sensation. Furthermore, no off-odor was detected in any of the samples in test areas 2-1 to 2-8.

[0725] Based on the results, it was confirmed that by adding at least two compounds selected from methyl cyclopentenolone, β-caryophyllene oxide, and furfural to food, the oral coating sensation can be effectively enhanced.

[0726] [Example 3]

[0727] Add at least one compound selected from methyl cyclopentenolone, β-caryophyllene oxide, and furfural to instant noodles for sensory evaluation of the oral coating sensation.

[0728] Specifically, first, prepare instant noodles (manufactured by Toyo Suisan Kaisha, Ltd., product name "Noodle Making Combination Miso (麺づくり合わせ味噌)": containing vegetable oil and animal oil (lard)) according to the instructions described in the product packaging. In the soup component of the instant noodles, add at least one compound selected from methyl cyclopentenolone, β-caryophyllene oxide, and furfural to make the concentration of each compound in the food (soup component) reach the concentration shown in Table 6 below, and prepare test samples (hereinafter referred to as "Sample of Test Area 3-1" to "Sample of Test Area 3-10"). Set the soup of instant noodles without adding any compound (negative control) as "0.0 points". In the range of 0.0 - 5.0 points, according to the following criteria, two professional evaluators negotiated and scored each test sample in increments of 0.5 points to conduct sensory evaluation. A score of 1.0 points or more was judged to have an enhanced oral coating sensation effect. In addition, for the two professional evaluators, in order to make the score change by 0.5 points, they were trained in advance to reach a consensus among the evaluators on how much the oral coating sensation changes, etc.

[0729] (Evaluation criteria for oral coating sensation)

[0730] 5.0 points: There is a sufficient oral coating sensation

[0731] 3.0 points: There is a certain oral coating sensation

[0732] 1.0 points: There is a slight oral coating sensation

[0733] [Table 6]

[0734]

[0735] [Example 4]

[0736] Add at least one compound selected from methyl cyclopentenolone, β-caryophyllene oxide, and furfural to instant noodles for sensory evaluation of the oral coating sensation.

[0737] Specifically, instant noodles (manufactured by Sanyo Foods Co., Ltd., product name "Sapporo Ichiban Miso Ramen Bowl" (containing vegetable oil)) were prepared according to the instructions on the product packaging. At least one compound selected from methylcyclopentenolone, β-caryophyllene oxide, and furfural was added to the soup component of these instant noodles to achieve the concentrations shown in Table 7 below, thus creating test samples (hereinafter referred to as "samples in test area 4-1" to "samples in test area 4-10"). The soup of the instant noodles without any added compounds (negative control) was set to "0.0 points." Within the range of 0.0 to 5.0 points, two professional evaluators, through consultation, scored each test sample on a 0.5-point scale according to the following criteria, conducting a sensory evaluation. A score of 1.0 or higher was considered to have an enhanced oral coverage effect. In addition, for the two professional evaluators, they were trained in advance to reach a consensus on the degree to which the oral cavity coverage should change in order to make a 0.5-point change in the score.

[0738] (Evaluation criteria for oral cavity coverage)

[0739] 5.0 points: Provides a good sense of coverage in the mouth.

[0740] 3.0 points: Provides a certain degree of oral coverage.

[0741] 1.0 point: Slight feeling of being covered in the mouth

[0742] Table 7

[0743]

[0744] As shown in Tables 6 and 7, the samples in test areas 3-4 to 3-10 and 4-4 to 4-10 of this invention, which contained at least two compounds selected from methylcyclopentenolone, β-caryophyllene oxide, and furfural, all effectively enhanced the oral coverage sensation. Furthermore, no off-odors were detected in the samples in test areas 3-1 to 3-10 and 4-1 to 4-10.

[0745] Based on these results, it can be confirmed that adding at least two compounds selected from methylcyclopentenolone, β-caryophyllene oxide, and furfural to food can effectively enhance the oral coverage sensation.

[0746] [Example 5]

[0747] <Positive and Negative Controls>

[0748] The positive and negative controls used the same commercially available mayonnaise as in Example 1.

[0749] <Preparation of Test Samples>

[0750] The test sample was prepared as follows: a commercially available mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "Pure Select (registered trademark) KOKUUMA (registered trademark) Reduced 65% Calories", fat content: 23%) used as the negative control above, was supplemented with at least one compound selected from the compounds (I) shown in Table 8 below (any one of methylcyclopentenolone, γ-butyrolactone, 2-methyltetrahydrofuran-3-one, α-angelicolone, maltol, 3-methyl-1,2-cyclohexanedione, γ-dodecanolide, 5-dodecanolide, 4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one and D-camphor), β-caryophyllene oxide and furfural. Compound (I) was added at a concentration of 10 ppb by weight in the food (mayonnaise), β-caryophyllene oxide was added at a concentration of 500 ppb by weight in the food (mayonnaise), and furfural was added at a concentration of 500 ppb by weight in the food (mayonnaise).

[0751] <Sensory Evaluation>

[0752] The intensity of the oral cavity coverage sensation of the test samples was evaluated using the same sensory evaluation method as in Example 1. The results are shown in Table 8 below.

[0753]

[0754] As shown in Table 8, the test samples of the present invention containing at least two compounds selected from the group consisting of compound (I) (any one of methylcyclopentenolone, γ-butyrolactone, 2-methyltetrahydrofuran-3-one, α-angelicolone, maltol, 3-methyl-1,2-cyclohexanedione, γ-dodecanolide, 5-dodecanolide, 4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one and D-camphor), β-caryophyllene oxide, and furfural effectively enhanced the oral coverage sensation. Furthermore, these test samples were odorless.

[0755] The results confirm that adding at least two compounds selected from the group consisting of compound (I), β-caryophyllene oxide, and furfural to food can effectively enhance the oral coating sensation without imparting any off-flavors to the food.

[0756] [Example 6]

[0757] <Positive and Negative Controls>

[0758] The positive and negative controls used the same commercially available mayonnaise as in Example 1.

[0759] <Preparation of Test Samples>

[0760] The test sample was prepared as follows: a commercially available mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "Pure Select (registered trademark) KOKUUMA (registered trademark) Reduced 65% Calories", fat content: 23%) used as the negative control above was supplemented with at least one compound selected from the compounds (II) shown in Table 9 below (any one of furfural, 2-acetylfuran, 2-acetyl-5-methylfuran, 3-acetyl-2,5-dimethylfuran, furfuryl alcohol, 1-furfurylpyrrole, furfuryl propionate, 5-methylfurfural and 5-(hydroxymethyl)furfural), β-caryophyllene oxide and methylcyclopentenolone. Compound (II) was added at a concentration of 10 ppb by weight in the food (mayonnaise), β-caryophyllene oxide was added at a concentration of 500 ppb by weight in the food (mayonnaise), and methylcyclopentenolone was added at a concentration of 500 ppb by weight in the food (mayonnaise).

[0761] <Sensory Evaluation>

[0762] The intensity of the oral cavity coverage sensation of the test samples was evaluated using the same sensory evaluation method as in Example 1. The results are shown in Table 9 below.

[0763]

[0764] As shown in Table 9, the test samples of the present invention containing at least two compounds selected from the group consisting of compound (II) (furfural, 2-acetylfuran, 2-acetyl-5-methylfuran, 3-acetyl-2,5-dimethylfuran, furfuryl alcohol, 1-furfurylpyrrole, furfuryl propionate, 5-methylfurfural, and any one of 5-methylfurfural and 5-(hydroxymethyl)furfural), β-caryophyllene oxide, and methylcyclopentenolone all effectively enhanced the oral coverage sensation. Furthermore, these test samples were odorless.

[0765] The results confirm that adding at least two compounds selected from the group consisting of compound (II), β-caryophyllene oxide and methylcyclopentenolone to food can effectively enhance the oral coating sensation without imparting any off-flavors to the food.

[0766] [Example 7]

[0767] <Preparation of instant noodles in control area 1>

[0768] Dissolve 1.6 parts by weight of salt, 0.1 parts by weight of potassium carbonate (food additive grade), and 0.1 parts by weight of sodium carbonate (food additive grade) in 35 parts by weight of water. Mix 36.8 parts by weight of the resulting aqueous solution (hereinafter referred to as "kneading water") with 100 parts by weight of flour (quasi-strong flour) for 5 minutes. Use an electric pasta machine (Imperia, RM-220) to form sheets (thickness: 1.3 ± 0.1 mm). Trim the ends and cut into 1 mm wide and 30 cm long pieces, then freeze at -20°C. Steam the frozen noodles at 98°C for 10 minutes. Add 30 g of 4% salt water heated to approximately 50°C to 100 g of steamed noodles for seasoning. Fry the seasoned noodles in oil at 150°C for 3.5 minutes, then cool to room temperature to obtain instant noodles (hereinafter referred to as "instant noodles of control area 1"). Here, a mixture of lard and palm oil is used for frying (lard: 50% by weight, palm oil: 50% by weight). Instant noodles should be refrigerated at 5°C before use.

[0769] <Making Instant Noodles in Comparison Area 2>

[0770] As for the frying oil, except that lard (lard: 100% by weight) is used instead of the mixture of lard and palm oil (lard: 50% by weight, palm oil: 50% by weight), the instant noodles are made in the same order as in control zone 1 (hereinafter, the instant noodles are referred to as "instant noodles of control zone 2").

[0771] <Production of Instant Noodles in Experimental Zone 1>

[0772] In the preparation of the kneading water, in addition to salt, potassium carbonate, and sodium carbonate, methylcyclopentenolone and β-caryophyllene oxide were further dissolved in water. Otherwise, instant noodles were prepared in the same order as in control area 1 (hereinafter, these instant noodles are referred to as "instant noodles of test area 1"). Here, methylcyclopentenolone was used at a concentration of 376 ppb by weight in the prepared instant noodles, and β-caryophyllene oxide was used at a concentration of 18751 ppb by weight in the prepared instant noodles.

[0773] <Production of Instant Noodles in Experimental Zone 2>

[0774] In the preparation of the kneading water, in addition to salt, potassium carbonate, and sodium carbonate, β-caryophyllene oxide and furfural were further dissolved in water. Otherwise, instant noodles were prepared in the same order as in control area 1 (hereinafter, these instant noodles are referred to as "instant noodles of test area 2"). Here, β-caryophyllene oxide was used at a concentration of 18751 ppb by weight in the prepared instant noodles, and furfural was used at a concentration of 18751 ppb by weight in the prepared instant noodles.

[0775] <Production of Instant Noodles in Experimental Zone 3>

[0776] In the preparation of the kneading water, in addition to salt, potassium carbonate, and sodium carbonate, methylcyclopentenolone and furfural were further dissolved in the water. Otherwise, instant noodles were made in the same order as in control area 1 (hereinafter, these instant noodles are referred to as "instant noodles of test area 3"). Here, methylcyclopentenolone was used at a concentration of 376 ppb by weight in the prepared instant noodles, and furfural was used at a concentration of 18751 ppb by weight in the prepared instant noodles.

[0777] <Production of Instant Noodles in Experimental Zone 4>

[0778] In the preparation of the kneading water, in addition to salt, potassium carbonate, and sodium carbonate, methylcyclopentenolone, β-caryophyllene oxide, and furfural were further dissolved in water. Otherwise, instant noodles were prepared in the same order as in control area 1 (hereinafter, these instant noodles are referred to as "instant noodles of test area 4"). Here, methylcyclopentenolone was used at a concentration of 376 ppb by weight in the prepared instant noodles, β-caryophyllene oxide was used at a concentration of 18751 ppb by weight in the prepared instant noodles, and furfural was used at a concentration of 18751 ppb by weight in the prepared instant noodles.

[0779] <Production of Instant Noodles in Experimental Zone 5>

[0780] In the preparation of the kneading water, in addition to salt, potassium carbonate, and sodium carbonate, methylcyclopentenolone, β-caryophyllene oxide, and furfural were further dissolved in water. Otherwise, instant noodles were prepared in the same order as in control area 1 (hereinafter, these instant noodles are referred to as "instant noodles of test area 5"). Here, methylcyclopentenolone was used at a concentration of 470 ppb by weight in the prepared instant noodles, β-caryophyllene oxide was used at a concentration of 23438 ppb by weight in the prepared instant noodles, and furfural was used at a concentration of 23438 ppb by weight in the prepared instant noodles.

[0781] <Production of Instant Noodles in Experimental Zone 6>

[0782] In the preparation of the kneading water, in addition to salt, potassium carbonate, and sodium carbonate, methylcyclopentenolone, β-caryophyllene oxide, and furfural were further dissolved in water. Otherwise, instant noodles were prepared in the same order as in control area 1 (hereinafter, these instant noodles are referred to as "instant noodles of test area 6"). Here, methylcyclopentenolone was used at a concentration of 564 ppb by weight in the prepared instant noodles, β-caryophyllene oxide was used at a concentration of 28,126 ppb by weight in the prepared instant noodles, and furfural was used at a concentration of 28,126 ppb by weight in the prepared instant noodles.

[0783] <Comparison of Instant Noodles Production in Section 1>

[0784] In the preparation of the kneading water, methylcyclopentenolone was further dissolved in water in addition to salt, potassium carbonate, and sodium carbonate. Otherwise, instant noodles were made in the same order as in control area 1 (hereinafter, these instant noodles are referred to as "instant noodles of comparison area 1"). Here, methylcyclopentenolone was used in such a way that the concentration of methylcyclopentenolone in the prepared instant noodles was 376 ppb by weight.

[0785] <Comparison Section 2: Instant Noodle Making>

[0786] In the preparation of the kneading water, β-caryophyllene oxide was further dissolved in water in addition to salt, potassium carbonate, and sodium carbonate. Otherwise, instant noodles were prepared in the same order as in control area 1 (hereinafter, these instant noodles are referred to as "instant noodles in comparison area 2"). Here, β-caryophyllene oxide was used in such a way that the concentration of β-caryophyllene oxide in the prepared instant noodles was 18751 ppb by weight.

[0787] <Comparison Section 3: Instant Noodle Making>

[0788] In the preparation of the kneading water, furfural was further dissolved in water in addition to salt, potassium carbonate, and sodium carbonate. Otherwise, instant noodles were made in the same order as in control area 1 (hereinafter, these instant noodles are referred to as "instant noodles in comparison area 3"). Here, furfural was used in such a way that the concentration of furfural in the prepared instant noodles was 18751 ppb by weight.

[0789] <Sensory Evaluation>

[0790] The intensity of oral coverage of each instant noodle in control areas 1 and 2, test areas 1 to 6, and comparison areas 1 to 3 was evaluated using sensory evaluation.

[0791] Specifically, each instant noodle was boiled in 250g of hot water for 3.5 minutes, and then 4.2g of powdered broth from a commercially available instant noodle product (manufactured by Toyo Suisan Co., Ltd., product name "Gekimen Wonton Noodles") was added to prepare the ramen. Four professional evaluators tasted each ramen, assigning a score of "0.0" to the instant noodle-based ramen from control area 1 and "5.0" to the instant noodle-based ramen from control area 2. Within the range of 0.0 to 5.0, each ramen was scored on a 0.5-point scale according to the following criteria (non-blind). The scores from the four professional evaluators were then averaged. A score of 1 or higher was considered to have an enhanced oral cavity coverage effect. Furthermore, the four professional evaluators were trained beforehand to ensure a consensus among them on the degree of change in oral cavity coverage, allowing for variations in scores within 0.5-point increments.

[0792] (Evaluation criteria for oral cavity coverage)

[0793] 5.0 points: Provides a good sense of coverage in the mouth.

[0794] 3.0 points: Provides a certain degree of oral coverage.

[0795] 1.0 point: Slight feeling of being covered in the mouth

[0796] The results are shown in Table 10 below.

[0797] Table 10

[0798] Control area 1 Control area 2 Comparison Area 1 Comparison Zone 2 Comparison Zone 3 0.0 5.0 0.0 1.0 0.0

[0799] Experimental Zone 1 Experimental Zone 2 Experimental Zone 3 Experimental Zone 4 Experimental Zone 5 Experimental Zone 6 2.0 2.0 1.5 3.5 4.0 4.5

[0800] As shown in Table 10, the instant noodles in test areas 1-6 of the present invention, which contain at least two compounds selected from methylcyclopentenolone, β-caryophyllene oxide, and furfural, all effectively enhanced the oral coating sensation. Furthermore, these instant noodles had no off-flavor.

[0801] Based on these results, it can be confirmed that adding at least two compounds selected from methylcyclopentenolone, β-caryophyllene oxide, and furfural to food can effectively enhance the oral envelopment without imparting any off-flavors to the food.

[0802] Industrial availability

[0803] According to the present invention, a flavoring composition that can effectively enhance the oral envelopment sensation can be provided. Furthermore, according to the present invention, a flavoring composition that can effectively enhance the oral envelopment sensation without imparting an unpleasant odor to food can be provided.

[0804] According to the present invention, a food product that effectively enhances the oral sensation and a method for manufacturing the same can be provided. Furthermore, according to the present invention, a food product that effectively enhances the oral sensation and is odorless, and a method for manufacturing the same can be provided.

[0805] According to the present invention, a method that can effectively enhance the oral cavity's sense of coverage can be provided. Furthermore, according to the present invention, a method that can effectively enhance the oral cavity's sense of coverage without imparting any unpleasant odor to food can be provided.

[0806] This application is based on Japanese Special Application 2020-152965 (application date: September 11, 2020), the contents of which are fully contained in this specification.

Claims

1. A flavour composition, wherein, The flavor composition contains (A), and contains (B) or (C), or, The flavor composition contains (A), (B), and (C), (B) is β-oxobergamotene, and (C) is a compound represented by general formula (II): wherein R is an acyl group having 1 to 6 carbon atoms, a hydroxy group, a pyrrolyl group, or an acyloxy group having 1 to 6 carbon atoms; 3 wherein R is an acyl group having 1 to 6 carbon atoms, a hydroxy group, a pyrrolyl group, or an acyloxy group having 1 to 6 carbon atoms; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 4 R is a substituent; m represents an integer of 0 to 3, (A) is at least one compound selected from the group consisting of methyl cyclopentenolone, 3-methyl-1,2-cyclohexanedione, and D-camphor, When the composition contains at least (A), the composition is added to a food in such a manner that the concentration a of (A) in the food is 0.05 to 5000 parts by weight per billion parts by weight of the total weight of the food at the time of eating the food; When the composition contains at least (B), the composition is added to a food in such a manner that the concentration b of (B) in the food is 0.1 to 50000 parts by weight per billion parts by weight of the total weight of the food at the time of eating the food; When the composition contains at least (C), the composition is added to a food in such a manner that the concentration c of (C) in the food is 0.1 to 50000 parts by weight per billion parts by weight of the total weight of the food at the time of eating the food.

2. The composition according to claim 1, wherein (C) is at least one compound selected from the group consisting of furfural, 2-acetylfuran, 2-acetyl-5-methylfuran, 3-acetyl-2,5-dimethylfuran, furfuryl alcohol, 1-furfurylpyrrole, furfuryl propionate, 5-methylfurfural, and 5-(hydroxymethyl)furfural.

3. The composition according to claim 1 or 2, wherein, At least two compounds containing (A), and containing (B) and / or (C) are any one of the following (i) to (xviii): (i) at least two compounds containing (A) methyl cyclopentenolone, and containing (B) β-oxobergamotene and / or (C) furfural; (vi) at least two compounds containing (A) 3-methyl-1,2-cyclohexanedione, and containing (B) β-oxobergamotene and / or (C) furfural; (x) at least two compounds containing (A) D-camphor, and containing (B) β-oxobergamotene and / or (C) furfural; (xi) at least two compounds containing (A) methyl cyclopentenolone, and containing (B) β-oxobergamotene and / or (C) 2-acetylfuran; (xii) at least two compounds containing (A) methyl cyclopentenolone, and containing (B) β-oxobergamotene and / or (C) 2-acetyl-5-methylfuran; (xiii) at least two compounds containing (A) methyl cyclopentenolone, and containing (B) β-oxobergamotene and / or (C) 3-acetyl-2,5-dimethylfuran; (xiv) at least two compounds containing (A) methyl cyclopentenolone, and containing (B) β-oxobergamotene and / or (C) furfuryl alcohol; (xv) at least two compounds containing (A) methyl cyclopentenolone, and containing (B) β-oxobergamotene and / or (C) 1-furfurylpyrrole; (xvi) at least two compounds containing (A) methyl cyclopentenolone, and containing (B) β-oxobergamotene and / or (C) furfuryl propionate; (xvii) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxocamphene and / or (C) 5-methylfurfural; (xviii) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxocamphene and / or (C) 5-(hydroxymethyl)furfural.

4. The composition according to claim 1 or 2, wherein, At least two compounds containing (A), and containing (B) and / or (C) are at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxocamphene and / or (C) furfural.

5. The composition according to claim 1 or 2, for use in enhancing the mouth coating sensation.

6. The composition according to claim 1 or 2, containing (A), (B) and (C).

7. The composition according to claim 1 or 2, when the composition contains at least (A), the composition is added to the food in such a manner that the concentration a of (A) in the food is 0.5 to 1000 parts by weight per billion parts by weight of the total weight of the food at the time of eating; when the composition contains at least (B), the composition is added to the food in such a manner that the concentration b of (B) in the food is 10 to 5000 parts by weight per billion parts by weight of the total weight of the food at the time of eating; when the composition contains at least (C), the composition is added to the food in such a manner that the concentration c of (C) in the food is 10 to 5000 parts by weight per billion parts by weight of the total weight of the food at the time of eating.

8. The composition according to claim 1 or 2, when the composition contains at least (A), the composition is added to the food in such a manner that the concentration a of (A) in the food is 10 to 1000 parts by weight per billion parts by weight of the total weight of the food at the time of eating; when the composition contains at least (B), the composition is added to the food in such a manner that the concentration b of (B) in the food is 500 to 5000 parts by weight per billion parts by weight of the total weight of the food at the time of eating; when the composition contains at least (C), the composition is added to the food in such a manner that the concentration c of (C) in the food is 500 to 5000 parts by weight per billion parts by weight of the total weight of the food at the time of eating.

9. The composition according to claim 1 or 2, when the composition contains at least (A) and (B), the weight ratio of the content of (A) to the content of (B) in the composition is A:B = 1 : 0.001 to 1000; when the composition contains at least (A) and (C), the weight ratio of the content of (A) to the content of (C) in the composition is A:C = 1 : 0.001 to 1000; when the composition contains at least (B) and (C), the weight ratio of the content of (B) to the content of (C) in the composition is B:C = 1 : 0.001 to 1000.

10. The composition according to claim 1 or 2, when the composition contains at least (A) and (B), the composition is added to the food in such a manner that the weight ratio of the concentration a of (A) to the concentration b of (B) in the food is a:b = 1 : 0.001 to 1000; When the composition contains at least (A) and (C), the composition is added to the food in such a manner that the weight ratio of the concentration a of (A) to the concentration c of (C) in the food is a : c = 1 : 0.001 to 1000; When the composition contains at least (B) and (C), the composition is added to the food in such a manner that the weight ratio of the concentration b of (B) to the concentration c of (C) in the food is b : c = 1 : 0.001 to 1000.

11. A method of manufacturing a food product, wherein, The method includes adding (A), and adding (B) or (C), or The method includes adding (A), (B) and (C), (B) is β-oxocymene, and (C) is a compound represented by general formula (II): wherein R is an acyl group having 1 to 6 carbon atoms, a hydroxy group, a pyrrolyl group, or an acyloxy group having 1 to 6 carbon atoms; 3 wherein R is an acyl group having 1 to 6 carbon atoms, a hydroxy group, a pyrrolyl group, or an acyloxy group having 1 to 6 carbon atoms; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 4 R is a substituent; m represents an integer of 0 to 3, (A) is at least one compound selected from the group consisting of methylcyclopentenolone, 3-methyl-l,2-cyclohexanedione and D-camphor, When the manufacturing method includes adding at least (A), the addition of (A) is performed in such a manner that the concentration a of (A) in the food is 0.05 to 5000 weight ppb with respect to the total weight of the food at the time of eating; When the manufacturing method includes adding at least (B), the addition of (B) is performed in such a manner that the concentration b of (B) in the food is 0.1 to 50000 weight ppb with respect to the total weight of the food at the time of eating; When the manufacturing method includes adding at least (C), the addition of (C) is performed in such a manner that the concentration c of (C) in the food is 0.1 to 50000 weight ppb with respect to the total weight of the food at the time of eating.

12. The manufacturing method according to claim 11, wherein (C) is at least one compound selected from the group consisting of furfural, 2-acetylfuran, 2-acetyl-5-methylfuran, 3-acetyl-2,5-dimethylfuran, furfuryl alcohol, 1-furfurylpyrrole, furfuryl propionate, 5-methylfurfural and 5-(hydroxymethyl)furfural.

13. The manufacturing method according to claim 11 or 12, wherein, At least two compounds containing (A), and containing (B) and / or (C) are any one of the following (i) to (xviii): (i) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxocymene and / or (C) furfural; (vi) at least two compounds containing (A) 3-methyl-l,2-cyclohexanedione, and containing (B) β-oxocymene and / or (C) furfural; (x) at least two compounds containing (A) D-camphor, and containing (B) β-oxocymene and / or (C) furfural; (xi) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxocymene and / or (C) 2-acetylfuran; (xii) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxocymene and / or (C) 2-acetyl-5-methylfuran; (xiii) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxocymene and / or (C) 3-acetyl-2,5-dimethylfuran; (xiv) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxobicycloheptene and / or (C) furfuryl alcohol; (xv) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxobicycloheptene and / or (C) 1-furfurylpyrrole; (xvi) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxobicycloheptene and / or (C) furfuryl propionate; (xvii) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxobicycloheptene and / or (C) 5-methylfurfural; (xviii) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxobicycloheptene and / or (C) 5-(hydroxymethyl)furfural.

14. The production method according to claim 11 or 12, the at least two compounds containing (A), and containing (B) and / or (C) being at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxobicycloheptene and / or (C) furfural.

15. The production method according to claim 11 or 12, the food being a food with enhanced mouth-coating sensation.

16. The production method according to claim 11 or 12, comprising adding (A), (B), and (C).

17. The production method according to claim 11 or 12, when the production method comprises at least adding (A), the addition of (A) is performed in such a manner that the concentration a of (A) in the food is 0.5 to 1000 weight ppb with respect to the total weight at the time of eating the food; when the production method comprises at least adding (B), the addition of (B) is performed in such a manner that the concentration b of (B) in the food is 10 to 5000 weight ppb with respect to the total weight at the time of eating the food; when the production method comprises at least adding (C), the addition of (C) is performed in such a manner that the concentration c of (C) in the food is 10 to 5000 weight ppb with respect to the total weight at the time of eating the food.

18. The production method according to claim 11 or 12, when the production method comprises at least adding (A), the addition of (A) is performed in such a manner that the concentration a of (A) in the food is 10 to 1000 weight ppb with respect to the total weight at the time of eating the food; when the production method comprises at least adding (B), the addition of (B) is performed in such a manner that the concentration b of (B) in the food is 500 to 5000 weight ppb with respect to the total weight at the time of eating the food; when the production method comprises at least adding (C), the addition of (C) is performed in such a manner that the concentration c of (C) in the food is 500 to 5000 weight ppb with respect to the total weight at the time of eating the food.

19. The production method according to claim 11 or 12, when the production method comprises at least adding (A) and (B), the addition of (A) and (B) is performed in such a manner that the weight ratio of the concentration a of (A) to the concentration b of (B) in the food is a : b = 1 : 0.001 to 1000. The preparation method includes at least adding (A) and (C), and the addition of (A) and (C) is performed in such a manner that the weight ratio of the concentration a of (A) to the concentration c of (C) in the food is a : c = 1 : 0.001 to 1000; The preparation method includes at least adding (B) and (C), and the addition of (B) and (C) is performed in such a manner that the weight ratio of the concentration b of (B) to the concentration c of (C) in the food is b : c = 1 : 0.001 to 1000.

20. A food product, wherein, The food contains (A), and contains (B) or (C), Alternatively, The food contains (A), (B), and (C), (B) is β-cedrene, and (C) is a compound represented by general formula (II): wherein R is an acyl group having 1 to 6 carbon atoms, a hydroxy group, a pyrrolyl group, or an acyloxy group having 1 to 6 carbon atoms; 3 wherein R is an acyl group having 1 to 6 carbon atoms, a hydroxy group, a pyrrolyl group, or an acyloxy group having 1 to 6 carbon atoms; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 4 is a substituent; m represents an integer of 0 to 3, (A) is at least one compound selected from the group consisting of methylcyclopentenolone, 3-methyl-1,2-cyclohexanedione, and D-camphor, When the food contains at least (A), the concentration a of (A) in the food is 0.05 to 5000 parts by weight per billion parts by weight relative to the total weight of the food at the time of eating; When the food contains at least (B), the concentration b of (B) in the food is 0.1 to 50000 parts by weight per billion parts by weight relative to the total weight of the food at the time of eating; When the food contains at least (C), the concentration c of (C) in the food is 0.1 to 50000 parts by weight per billion parts by weight relative to the total weight of the food at the time of eating.

21. The food according to claim 20, wherein (C) is at least one compound selected from the group consisting of furfural, 2-acetylfuran, 2-acetyl-5-methylfuran, 3-acetyl-2,5-dimethylfuran, furfuryl alcohol, 1-furfurylpyrrole, furfuryl propionate, 5-methylfurfural, and 5-(hydroxymethyl)furfural.

22. The food product of claim 20 or 21, wherein, At least two compounds containing (A), and containing (B) and / or (C) are any one of the following (i) to (xviii): (i) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-cedrene and / or (C) furfural; (vi) at least two compounds containing (A) 3-methyl-1,2-cyclohexanedione, and containing (B) β-cedrene and / or (C) furfural; (x) at least two compounds containing (A) D-camphor, and containing (B) β-cedrene and / or (C) furfural; (xi) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-cedrene and / or (C) 2-acetylfuran; (xii) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-cedrene and / or (C) 2-acetyl-5-methylfuran; (xiii) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-cedrene and / or (C) 3-acetyl-2,5-dimethylfuran; (xiv) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-cedrene and / or (C) furfuryl alcohol; (xv) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxobicyclo[2.2.1]hept-5-ene and / or (C) 1-furfurylpyrrole; (xvi) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxobicyclo[2.2.1]hept-5-ene and / or (C) furfuryl propionate; (xvii) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxobicyclo[2.2.1]hept-5-ene and / or (C) 5-methylfurfural; (xviii) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxobicyclo[2.2.1]hept-5-ene and / or (C) 5-(hydroxymethyl)furfural.

23. The food according to claim 20 or 21, the at least two compounds containing (A), and containing (B) and / or (C) are at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxobicyclo[2.2.1]hept-5-ene and / or (C) furfural.

24. The food according to claim 20 or 21, which is a food having enhanced mouth-coating sensation.

25. The food according to claim 20 or 21, which contains (A), (B) and (C).

26. The food according to claim 20 or 21, when the food contains at least (A), the concentration a of (A) in the food is 0.5 to 1000 parts by weight per billion parts by weight of the total weight of the food at the time of eating; when the food contains at least (B), the concentration b of (B) in the food is 10 to 5000 parts by weight per billion parts by weight of the total weight of the food at the time of eating; when the food contains at least (C), the concentration c of (C) in the food is 10 to 5000 parts by weight per billion parts by weight of the total weight of the food at the time of eating.

27. The food according to claim 20 or 21, when the food contains at least (A), the concentration a of (A) in the food is 10 to 1000 parts by weight per billion parts by weight of the total weight of the food at the time of eating; when the food contains at least (B), the concentration b of (B) in the food is 500 to 5000 parts by weight per billion parts by weight of the total weight of the food at the time of eating; when the food contains at least (C), the concentration c of (C) in the food is 500 to 5000 parts by weight per billion parts by weight of the total weight of the food at the time of eating.

28. The food according to claim 20 or 21, when the food contains at least (A) and (B), the weight ratio of the concentration a of (A) to the concentration b of (B) in the food is a : b = 0.001 to 1000; when the food contains at least (A) and (C), the weight ratio of the concentration a of (A) to the concentration c of (C) in the food is a : c = 1 : 0.001 to 1000; when the food contains at least (B) and (C), the weight ratio of the concentration b of (B) to the concentration c of (C) in the food is b : c = 1 : 0.001 to 1000.

29. A method of enhancing mouth coating, wherein, the method comprises adding (A) to the food, and adding (B) or (C), or, the method comprises adding (A), (B) and (C) to the food, (B) is β-oxobicyclo[2.2.1]hept-5-ene, and (C) is a compound represented by the general formula (II): wherein R is an acyl group having 1 to 6 carbon atoms, a hydroxy group, a pyrrolyl group, or an acyloxy group having 1 to 6 carbon atoms; 3 wherein R is an acyl group having 1 to 6 carbon atoms, a hydroxy group, a pyrrolyl group, or an acyloxy group having 1 to 6 carbon atoms; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 4 R is a substituent; m represents an integer of 0 to 3, (A) is at least one compound selected from the group consisting of methylcyclopentenolone, 3-methyl-1,2-cyclohexanedione, and D-camphor, when the enhancement method includes at least the addition of (A), the addition of (A) is performed in such a manner that the concentration a of (A) in the food is 0.05 to 5000 parts by weight per billion parts by weight relative to the total weight at the time of eating the food; when the enhancement method includes at least the addition of (B), the addition of (B) is performed in such a manner that the concentration b of (B) in the food is 0.1 to 50000 parts by weight per billion parts by weight relative to the total weight at the time of eating the food; when the enhancement method includes at least the addition of (C), the addition of (C) is performed in such a manner that the concentration c of (C) in the food is 0.1 to 50000 parts by weight per billion parts by weight relative to the total weight at the time of eating the food.

30. The enhancement method according to claim 29, wherein (C) is at least one compound selected from the group consisting of furfural, 2-acetylfuran, 2-acetyl-5-methylfuran, 3-acetyl-2,5-dimethylfuran, furfuryl alcohol, 1-furfurylpyrrole, furfuryl propionate, 5-methylfurfural, and 5-(hydroxymethyl)furfural.

31. The method of enhancing according to claim 29 or 30, wherein, At least two compounds containing (A), and containing (B) and / or (C) are any one of the following (i) to (xviii): (i) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxocymene and / or (C) furfural; (vi) at least two compounds containing (A) 3-methyl-1,2-cyclohexanedione, and containing (B) β-oxocymene and / or (C) furfural; (x) at least two compounds containing (A) D-camphor, and containing (B) β-oxocymene and / or (C) furfural; (xi) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxocymene and / or (C) 2-acetylfuran; (xii) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxocymene and / or (C) 2-acetyl-5-methylfuran; (xiii) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxocymene and / or (C) 3-acetyl-2,5-dimethylfuran; (xiv) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxocymene and / or (C) furfuryl alcohol; (xv) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxocymene and / or (C) 1-furfurylpyrrole; (xvi) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxocymene and / or (C) furfuryl propionate; (xvii) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxocymene and / or (C) 5-methylfurfural; (xviii) at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxocymene and / or (C) 5-(hydroxymethyl)furfural.

32. The enhancing method according to claim 29 or 30, the at least two compounds containing (A), and containing (B) and / or (C) are at least two compounds containing (A) methylcyclopentenolone, and containing (B) β-oxocymene and / or (C) furfural.

33. The enhancing method according to claim 29 or 30, comprising adding (A), (B) and (C).

34. The enhancing method according to claim 29 or 30, when the enhancing method comprises at least adding (A), the addition of (A) is performed in such a manner that the concentration a of (A) in the food is 0.5 to 1000 parts by weight ppb with respect to the total weight at the time of eating the food; when the enhancing method comprises at least adding (B), the addition of (B) is performed in such a manner that the concentration b of (B) in the food is 10 to 5000 parts by weight ppb with respect to the total weight at the time of eating the food; when the enhancing method comprises at least adding (C), the addition of (C) is performed in such a manner that the concentration c of (C) in the food is 10 to 5000 parts by weight ppb with respect to the total weight at the time of eating the food.

35. The enhancing method according to claim 29 or 30, when the enhancing method comprises at least adding (A), the addition of (A) is performed in such a manner that the concentration a of (A) in the food is 10 to 1000 parts by weight ppb with respect to the total weight at the time of eating the food; when the enhancing method comprises at least adding (B), the addition of (B) is performed in such a manner that the concentration b of (B) in the food is 500 to 5000 parts by weight ppb with respect to the total weight at the time of eating the food; when the enhancing method comprises at least adding (C), the addition of (C) is performed in such a manner that the concentration c of (C) in the food is 500 to 5000 parts by weight ppb with respect to the total weight at the time of eating the food.

36. The enhancing method according to claim 29 or 30, when the enhancing method comprises at least adding (A) and (B), the addition of (A) and (B) is performed in such a manner that the weight ratio of the concentration a of (A) to the concentration b of (B) in the food is a : b = 1 : 0.001 to 1000; when the enhancing method comprises at least adding (A) and (C), the addition of (A) and (C) is performed in such a manner that the weight ratio of the concentration a of (A) to the concentration c of (C) in the food is a : c = 1 : 0.001 to 1000; when the enhancing method comprises at least adding (B) and (C), the addition of (B) and (C) is performed in such a manner that the weight ratio of the concentration b of (B) to the concentration c of (C) in the food is b : c = 1 : 0.001 to 1000.

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