Mouth coating enhancer

Abstract

The object of the present invention is to provide an effective oral coating enhancer, coffee roasting enhancer, etc. The present invention relates to an oral coating enhancer, coffee roasting enhancer, etc., which comprises the following (A) and / or (B) heated product or at least one compound selected from the compound group (C) described in the present specification. (A) (A1) A compound represented by the general formula (I): [wherein each symbol is as defined in the present specification], and (A2) At least one selected from the group consisting of aliphatic aldehydes having 3 to 14 carbon atoms, aromatic aldehydes having 7 to 12 carbon atoms, aliphatic alcohols having 3 to 12 carbon atoms, and substances that produce at least one of these compounds by heating, (B) At least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene-like compounds.

Description

Technical Field

[0001] The present invention relates to an oral coating enhancer and a method for producing the same. In addition, the present invention relates to a food having an enhanced oral coating feeling and a method for producing the same, and a method for enhancing the oral coating feeling. Furthermore, the present invention relates to an agent for enhancing a coffee roasted feeling and a method for producing the same, and a method for enhancing the coffee roasted feeling, etc. Background Art

[0002] "Mouth-coating feel" refers to the feeling of the mouth being covered with a thin film, the feeling of the mouth being covered with a fat or fat-like film, the smooth feeling felt in the mouth, and the fat-like thick feeling (heaviness) spreading throughout the mouth. If there is a method that can easily enhance the mouth-coating feel, for example, even a small amount of fat can fully provide the satisfactory feeling that is clearly felt when the mouth contains fat, etc., and it is believed that it can suppress excessive calorie intake and has the advantage of being expected to be effective in preventing metabolic diseases such as obesity.

[0003] As a method for enhancing the oral coating feeling, methods using hydrocolloids, low molecular weight compounds, polyphenols or glycosides have been reported in the past (Non-Patent Documents 1 to 5). However, the feeling enhanced by any method has the problem of being different in quality from the oral coating feeling that is clearly felt when the oral cavity contains oils and fats.

[0004] Prior art literature

[0005] Non-patent literature

[0006] Non-patent document 1: Arocas et al., "Sensory properties determined by starchtype in white sauces: effects of freeze / thaw and hydrocolloid addition." J FoodSci 2010, 75: S132-S140.

[0007] Non-patent document 2: Flett et al., "Perceived creaminess and viscosity of aggregated particles of casein micelles and κ-carrageenan." J Food Sci 2010, 75: S255-S261.

[0008] Non-patent document 3: Dawid et al., “Identification of sensory-active phytochemicals in asparagus (Asparagus officinalis L.)” J Agric Food Chem 2012, 60: 11877-11888.

[0009] Non-patent document 4: Schwarz et al., “Identification of novel orosensory active molecules in cured vanilla beans (Vanilla planifolia).” J Agric and Food Chem 2009, 57: 3729-3737.

[0010] Non-patent document 5: Scharbert et al., "Identification of the astringent tastecompounds in black tea infusions by combining instrumental analysis and human bioresponse." J Agric and Food Chem 2004, 52: 3498-3508. Summary of the invention

[0011] Problems to be solved by the invention

[0012] The present invention is made in view of the above situation, and the problem to be solved is to provide an effective agent for enhancing the coating sensation in the oral cavity. In addition, the problem to be solved by the present invention is to provide an effective agent for enhancing the roasted sensation of coffee.

[0013] Technical solutions to the problem

[0014] The present inventors have conducted in-depth research on the above-mentioned problems, and as a result, have found that a heated product obtained by heating a predetermined compound can enhance the coating feeling in the mouth. In addition, the present inventors have newly found that the heated product can enhance the roasted coffee feeling. The present inventors have also found that a predetermined compound that can be produced in the heated product can enhance the coating feeling in the mouth and the roasted coffee feeling. Based on these findings, the present inventors have further conducted in-depth research and completed the present invention.

[0015] That is, the present invention is as follows:

[0016] [1] An agent for enhancing oral coating sensation, comprising a heated product of the following (A) and / or (B), or at least one compound selected from the following compound group (C).

[0017] (A)(A1) A compound represented by the general formula (I):

[0018] [Chemistry 1]

[0019]

[0020] 〔In the formula,

[0021] R 1 It is an acyl group, a hydroxyl group or a pyrrol group having 1 to 6 carbon atoms;

[0022] Z is a single bond or an alkylene group having 1 to 6 carbon atoms;

[0023] R 2 is a substituent;

[0024] n represents an integer from 0 to 3], and

[0025] (A2) at least one selected from the group consisting of aliphatic aldehydes having 3 to 14 carbon atoms, aromatic aldehydes having 7 to 12 carbon atoms, aliphatic alcohols having 3 to 12 carbon atoms, and substances that generate at least one of these compounds upon heating,

[0026] (B) at least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene-like compounds,

[0027] [Compound Group (C)]

[0028] β-Caryophyllene oxide;

[0029] α-Pinene oxide;

[0030] Limonene oxide;

[0031] α-Terpinenol;

[0032] The compound represented by the general formula (II):

[0033] [Chemistry 2]

[0034]

[0035] 〔In the formula, R 3 and R 4 each independently represents a hydrogen atom, an acyl group having 1 to 18 carbon atoms, or an alkyl group having 1 to 6 carbon atoms];

[0036] The compound represented by the general formula (III):

[0037] [Chemistry 3]

[0038]

[0039] 〔In the formula, R 5 represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms];

[0040] The compound represented by the general formula (IV):

[0041] [Chemistry 4]

[0042]

[0043] 〔In the formula, R 6 represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms];

[0044] The compound represented by the general formula (V):

[0045] [Chemistry 5]

[0046]

[0047] 〔In the formula, R 7 and R 8 each independently represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms]:

[0048] (1S,6S,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecan-5-one,

[0049] (1S,6R,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecan-5-one,

[0050] (1R,4R,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carbaldehyde,

[0051] (1R,4S,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carbaldehyde,

[0052] (1S,2S,5R,9S)-1,4,4,8-tetramethyl-12-oxatricyclo[7.2.1.0 2,5 ] dodec-7-ene,

[0053] (1R,2S,5R,8R,9R)-1,4,4,8-tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ] dodecan-9-ol,

[0054] (1R,2S,5R,8R,9S)-1,4,4,8-tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ] dodecan-9-ol,

[0055] [1R-(1α,2α,5β,8β,9α)]-4,4,8-trimethyl-tricyclo[6.3.1.0 2,5 ]Dodecane-1,9-diol.

[0056] [2] The oral coating feeling enhancer according to [1], wherein

[0057] In the general formula (I), R 1 is formyl or acetyl, and Z is a single bond, or

[0058] In the general formula (I), R 1 is hydroxy or pyrrolyl, and Z is methylene.

[0059] [3] The oral coating feeling enhancer according to [1] or [2], wherein R 2 It is an alkyl group having 1 to 6 carbon atoms.

[0060] [4] The oral coating feeling enhancer according to any one of [1] to [3], wherein n represents 0 or 1.

[0061] [5] The oral coating enhancer according to any one of [1] to [4], wherein the compound represented by the general formula (I) is at least one compound selected from the group consisting of furfural, 5-methylfurfural, 2-furanylmethyl ketone, furfuryl alcohol and 1-furfurylpyrrole.

[0062] [6] The agent for enhancing oral coating sensation according to any one of [1] to [5], wherein (A2) is oil or fat.

[0063] [7] The oral coating enhancer according to any one of [1] to [6], wherein the β-caryophyllene-like compound is at least one compound selected from the group consisting of isocaryophyllene, β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, eugenol, limonene, 4-vinylphenol, linalool, linalool oxide, p-cymene, farnesene, myrcene, ocimene, α-phellandrene, α-terpinene, γ-terpinene and terpinolene (preferably at least one compound selected from the group consisting of β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, eugenol, limonene, 4-vinylphenol, linalool, linalool oxide, p-cymene, farnesene, myrcene, ocimene, α-phellandrene, α-terpinene, γ-terpinene and terpinolene).

[0064] [8] The oral coating enhancer according to [1], wherein at least one compound selected from compound group (C) is at least one compound selected from the group consisting of β-caryophyllene oxide, (1R,3Z,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol, (1R,4R,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undecane-4,5-diol, α-pinene oxide, limonene oxide, α-terpinenol, syringabicycloalkanediol, syringabicycloalkanediol-3-monoacetate, syringabicycloalkanediol diacetate and syringabicycloalkanediol-3-monoisovalerate.

[0065] [9] The agent for enhancing oral coating sensation according to any one of [1] to [8], which is used for fat-containing food.

[0066]

[10] A method for enhancing a coating sensation in the oral cavity, comprising the step of adding a heated substance of the following (A) and / or (B) or at least one compound selected from the following compound group (C).

[0067] (A)(A1) A compound represented by the general formula (I):

[0068] [Chemistry 6]

[0069]

[0070] 〔In the formula,

[0071] R 1 It is an acyl group, a hydroxyl group or a pyrrol group having 1 to 6 carbon atoms;

[0072] Z is a single bond or an alkylene group having 1 to 6 carbon atoms;

[0073] R 2 is a substituent;

[0074] n represents an integer from 0 to 3], and

[0075] (A2) at least one selected from the group consisting of aliphatic aldehydes having 3 to 14 carbon atoms, aromatic aldehydes having 7 to 12 carbon atoms, aliphatic alcohols having 3 to 12 carbon atoms, and substances that generate at least one of these compounds upon heating,

[0076] (B) at least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene-like compounds,

[0077] [Compound Group (C)]

[0078] β-Caryophyllene oxide;

[0079] α-Pinene oxide;

[0080] Limonene oxide;

[0081] α-Terpinenol;

[0082] The compound represented by the general formula (II):

[0083] [Chemistry 7]

[0084]

[0085] 〔In the formula, R 3 and R 4 each independently represents a hydrogen atom, an acyl group having 1 to 18 carbon atoms, or an alkyl group having 1 to 6 carbon atoms];

[0086] The compound represented by the general formula (III):

[0087] [Chemistry 8]

[0088]

[0089] 〔In the formula, R 5 represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms];

[0090] The compound represented by the general formula (IV):

[0091] [Chemistry 9]

[0092]

[0093] 〔In the formula, R 6 represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms];

[0094] The compound represented by the general formula (V):

[0095] [Chemistry 10]

[0096]

[0097] 〔In the formula, R 7 and R 8 each independently represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms]:

[0098] (1S,6S,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecan-5-one,

[0099] (1S,6R,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecan-5-one,

[0100] (1R,4R,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carbaldehyde,

[0101] (1R,4S,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carbaldehyde,

[0102] (1S,2S,5R,9S)-1,4,4,8-tetramethyl-12-oxatricyclo[7.2.1.0 2,5 ] dodec-7-ene,

[0103] (1R,2S,5R,8R,9R)-1,4,4,8-tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ] dodecan-9-ol,

[0104] (1R,2S,5R,8R,9S)-1,4,4,8-tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ] dodecan-9-ol,

[0105] [1R-(1α,2α,5β,8β,9α)]-4,4,8-trimethyl-tricyclo[6.3.1.0 2,5 ]Dodecane-1,9-diol.

[0106]

[11] The method for enhancing oral coating sensation according to

[10] , wherein:

[0107] In the general formula (I), R 1 is formyl or acetyl, and Z is a single bond, or

[0108] In the general formula (I), R 1 is hydroxy or pyrrolyl, and Z is methylene.

[0109]

[12] The method for enhancing oral coating feeling according to

[10] or

[11] , wherein R 2 It is an alkyl group having 1 to 6 carbon atoms.

[0110]

[13] The method for enhancing a coating feeling in the oral cavity according to any one of

[10] to

[12] , wherein n represents 0 or 1.

[0111]

[14] The method for enhancing the oral coating feeling according to any one of

[10] to

[13] , wherein the compound represented by the general formula (I) is at least one compound selected from the group consisting of furfural, 5-methylfurfural, 2-furanylmethyl ketone, furfuryl alcohol and 1-furfurylpyrrole.

[0112]

[15] The method for enhancing the oral coating feeling according to any one of

[10] to

[14] , wherein the (A2) is oil.

[0113]

[16] The method for enhancing the coating feeling in the oral cavity according to any one of

[10] to

[15] , wherein the β-caryophyllene-like compound is at least one compound selected from the group consisting of isocaryophyllene, β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, eugenol, limonene, 4-vinylphenol, linalool, linalool oxide, p-cymene, farnesene, myrcene, ocimene, α-phellandrene, α-terpinene, γ-terpinene and terpinolene (preferably at least one compound selected from the group consisting of β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, eugenol, limonene, 4-vinylphenol, linalool, linalool oxide, p-cymene, farnesene, myrcene, ocimene, α-phellandrene, α-terpinene, γ-terpinene and terpinolene).

[0114]

[17] The method for enhancing the oral coating feeling according to

[10] , wherein at least one compound selected from compound group (C) is at least one compound selected from the group consisting of β-caryophyllene oxide, (1R,3Z,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol, (1R,4R,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undecane-4,5-diol, α-pinene oxide, limonene oxide, α-terpinenol, eugenol, eugenol-3-monoacetate, eugenol-3-monoisovalerate.

[0115]

[18] The method for enhancing the oral coating feeling according to any one of

[10] to

[17] , which is a method for enhancing the oral coating feeling of a fat-containing food.

[0116]

[19] A method for producing a food, comprising the steps of heating the following (A) and / or (B) or adding at least one compound selected from the following compound group (C).

[0117] (A)(A1) A compound represented by the general formula (I):

[0118] [Chemistry 11]

[0119]

[0120] 〔In the formula,

[0121] R 1 It is an acyl group, a hydroxyl group or a pyrrol group having 1 to 6 carbon atoms;

[0122] Z is a single bond or an alkylene group having 1 to 6 carbon atoms;

[0123] R 2 is a substituent;

[0124] n represents an integer from 0 to 3], and

[0125] (A2) at least one selected from the group consisting of aliphatic aldehydes having 3 to 14 carbon atoms, aromatic aldehydes having 7 to 12 carbon atoms, aliphatic alcohols having 3 to 12 carbon atoms, and substances that generate at least one of these compounds upon heating,

[0126] (B) at least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene-like compounds,

[0127] [Compound Group (C)]

[0128] β-Caryophyllene oxide;

[0129] α-Pinene oxide;

[0130] Limonene oxide;

[0131] α-Terpinenol;

[0132] The compound represented by the general formula (II):

[0133] [Chemistry 12]

[0134]

[0135] 〔In the formula, R 3 and R 4 each independently represents a hydrogen atom, an acyl group having 1 to 18 carbon atoms, or an alkyl group having 1 to 6 carbon atoms];

[0136] The compound represented by the general formula (III):

[0137] [Chemistry 13]

[0138]

[0139] 〔In the formula, R 5 represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms];

[0140] The compound represented by the general formula (IV):

[0141] [Chemistry 14]

[0142]

[0143] 〔In the formula, R 6represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms];

[0144] The compound represented by the general formula (V):

[0145] [Chemistry 15]

[0146]

[0147] 〔In the formula, R 7 and R 8 each independently represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms]:

[0148] (1S,6S,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecan-5-one,

[0149] (1S,6R,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecan-5-one,

[0150] (1R,4R,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carbaldehyde,

[0151] (1R,4S,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carbaldehyde,

[0152] (1S,2S,5R,9S)-1,4,4,8-tetramethyl-12-oxatricyclo[7.2.1.0 2,5 ] dodec-7-ene,

[0153] (1R,2S,5R,8R,9R)-1,4,4,8-tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ] dodecan-9-ol,

[0154] (1R,2S,5R,8R,9S)-1,4,4,8-tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ] dodecan-9-ol,

[0155] [1R-(1α,2α,5β,8β,9α)]-4,4,8-trimethyl-tricyclo[6.3.1.0 2,5 ]Dodecane-1,9-diol.

[0156]

[20] The manufacturing method according to

[19] , wherein:

[0157] In the general formula (I), R 1 is formyl or acetyl, and Z is a single bond, or

[0158] In the general formula (I), R 1 is hydroxy or pyrrolyl, and Z is methylene.

[0159]

[21] The method according to

[19] or

[20] , wherein R 2 It is an alkyl group having 1 to 6 carbon atoms.

[0160]

[22] The production method according to any one of

[19] to

[21] , wherein n represents 0 or 1.

[0161]

[23] The production method according to any one of

[19] to

[22] , wherein the compound represented by the general formula (I) is at least one compound selected from the group consisting of furfural, 5-methylfurfural, 2-furanylmethyl ketone, furfuryl alcohol and 1-furfurylpyrrole.

[0162]

[24] The production method according to any one of

[19] to

[23] , wherein the (A2) is fat or oil.

[0163]

[25] The production method according to any one of

[19] to

[24] , wherein the β-caryophyllene-like compound is at least one compound selected from the group consisting of isocaryophyllene, β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, eugenol, limonene, 4-vinylphenol, linalool, linalool oxide, p-cymene, farnesene, myrcene, ocimene, α-phellandrene, α-terpinene, γ-terpinene and terpinolene (preferably at least one compound selected from the group consisting of β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, eugenol, limonene, 4-vinylphenol, linalool, linalool oxide, p-cymene, farnesene, myrcene, ocimene, α-phellandrene, α-terpinene, γ-terpinene and terpinolene).

[0164]

[26] The production method according to any one of

[19] to

[25] , wherein

[0165] The heating temperature of the component (A) is 40 to 200° C., and the heating time is 0.1 to 500 minutes.

[0166] The heating temperature of the component (B) is 40 to 200° C., and the heating time is 0.1 to 500 minutes.

[0167]

[27] The production method according to

[19] , wherein at least one compound selected from compound group (C) is at least one compound selected from the group consisting of β-caryophyllene oxide, (1R,3Z,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol, (1R,4R,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undecane-4,5-diol, α-pinene oxide, limonene oxide, α-terpinenol, syringabicycloalkanediol, syringabicycloalkanediol-3-monoacetate, syringabicycloalkanediol diacetate and syringabicycloalkanediol-3-monoisovalerate.

[0168]

[28] The production method according to any one of

[19] to

[27] , wherein the food is a food having an enhanced oral coating feeling.

[0169]

[29] The production method according to any one of

[19] to

[28] , wherein the food is a fat-containing food.

[0170]

[30] A food comprising the heated product of the following (A) and / or (B) or at least one compound selected from the following compound group (C).

[0171] (A)(A1) A compound represented by the general formula (I):

[0172] [Chemistry 16]

[0173]

[0174] 〔In the formula,

[0175] R 1 It is an acyl group, a hydroxyl group or a pyrrol group having 1 to 6 carbon atoms;

[0176] Z is a single bond or an alkylene group having 1 to 6 carbon atoms;

[0177] R 2 is a substituent;

[0178] n represents an integer from 0 to 3], and

[0179] (A2) at least one selected from the group consisting of aliphatic aldehydes having 3 to 14 carbon atoms, aromatic aldehydes having 7 to 12 carbon atoms, aliphatic alcohols having 3 to 12 carbon atoms, and substances that generate at least one of these compounds upon heating,

[0180] (B) at least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene-like compounds,

[0181] [Compound Group (C)]

[0182] β-Caryophyllene oxide;

[0183] α-Pinene oxide;

[0184] Limonene oxide;

[0185] α-Terpinenol;

[0186] The compound represented by the general formula (II):

[0187] [Chemistry 17]

[0188]

[0189] 〔In the formula, R 3 and R 4 each independently represents a hydrogen atom, an acyl group having 1 to 18 carbon atoms, or an alkyl group having 1 to 6 carbon atoms];

[0190] The compound represented by the general formula (III):

[0191] [Chemistry 18]

[0192]

[0193] 〔In the formula, R 5 represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms];

[0194] The compound represented by the general formula (IV):

[0195] [Chemistry 19]

[0196]

[0197] 〔In the formula, R 6 represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms];

[0198] The compound represented by the general formula (V):

[0199] [Chemistry 20]

[0200]

[0201] 〔In the formula, R 7 and R 8 each independently represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms]:

[0202] (1S,6S,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecan-5-one,

[0203] (1S,6R,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecan-5-one,

[0204] (1R,4R,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carbaldehyde,

[0205] (1R,4S,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carbaldehyde,

[0206] (1S,2S,5R,9S)-1,4,4,8-tetramethyl-12-oxatricyclo[7.2.1.0 2,5 ] dodec-7-ene,

[0207] (1R,2S,5R,8R,9R)-1,4,4,8-tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ] dodecan-9-ol,

[0208] (1R,2S,5R,8R,9S)-1,4,4,8-tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ] dodecan-9-ol,

[0209] [1R-(1α,2α,5β,8β,9α)]-4,4,8-trimethyl-tricyclo[6.3.1.0 2,5 ]Dodecane-1,9-diol.

[0210]

[31] A method for producing an agent for enhancing oral coating sensation, comprising the step of heating the following (A) and / or (B).

[0211] (A)(A1) A compound represented by the general formula (I):

[0212] [Chemistry 21]

[0213]

[0214] 〔In the formula,

[0215] R 1 It is an acyl group, a hydroxyl group or a pyrrol group having 1 to 6 carbon atoms;

[0216] Z is a single bond or an alkylene group having 1 to 6 carbon atoms;

[0217] R 2 is a substituent;

[0218] n represents an integer from 0 to 3], and

[0219] (A2) at least one selected from the group consisting of aliphatic aldehydes having 3 to 14 carbon atoms, aromatic aldehydes having 7 to 12 carbon atoms, aliphatic alcohols having 3 to 12 carbon atoms, and substances that generate at least one of these compounds upon heating,

[0220] (B) At least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene-like compounds.

[0221]

[32] The manufacturing method according to

[31] , wherein:

[0222] In the general formula (I), R 1 is formyl or acetyl, and Z is a single bond, or

[0223] In the general formula (I), R 1 is hydroxy or pyrrolyl, and Z is methylene.

[0224]

[33] The method according to

[31] or

[32] , wherein R 2 It is an alkyl group having 1 to 6 carbon atoms.

[0225]

[34] The production method according to any one of

[31] to

[33] , wherein n represents 0 or 1.

[0226]

[35] The production method according to any one of

[31] to

[34] , wherein the compound represented by the general formula (I) is at least one compound selected from the group consisting of furfural, 5-methylfurfural, 2-furanylmethyl ketone, furfuryl alcohol and 1-furfurylpyrrole.

[0227]

[36] The production method according to any one of

[31] to

[35] , wherein the (A2) is fat.

[0228]

[37] The production method according to any one of

[31] to

[36] , wherein the β-caryophyllene-like compound is at least one compound selected from the group consisting of isocaryophyllene, β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, eugenol, limonene, 4-vinylphenol, linalool, linalool oxide, p-cymene, farnesene, myrcene, ocimene, α-phellandrene, α-terpinene, γ-terpinene and terpinolene (preferably at least one compound selected from the group consisting of β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, eugenol, limonene, 4-vinylphenol, linalool, linalool oxide, p-cymene, farnesene, myrcene, ocimene, α-phellandrene, α-terpinene, γ-terpinene and terpinolene).

[0229]

[38] The production method according to any one of

[31] to

[37] , wherein

[0230] The heating temperature of the component (A) is 40 to 200° C., and the heating time is 0.1 to 500 minutes.

[0231] The heating temperature of the component (B) is 40 to 200° C., and the heating time is 0.1 to 500 minutes.

[0232]

[39] The production method according to

[31] , wherein at least one compound selected from compound group (C) is at least one compound selected from the group consisting of β-caryophyllene oxide, (1R,3Z,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol, (1R,4R,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undecane-4,5-diol, α-pinene oxide, limonene oxide, α-terpinenol, syringabicycloalkanediol, syringabicycloalkanediol-3-monoacetate, syringabicycloalkanediol diacetate and syringabicycloalkanediol-3-monoisovalerate.

[0233]

[40] The production method according to any one of

[31] to

[39] , wherein the oral coating feeling enhancer is used for fat-containing food.

[0234]

[41] A coffee roasting enhancer comprising a heated product of the following (A) and / or (B) or at least one compound selected from the following compound group (C).

[0235] (A)(A1) A compound represented by the general formula (I):

[0236] [Chemistry 22]

[0237]

[0238] 〔In the formula,

[0239] R 1 It is an acyl group, a hydroxyl group or a pyrrol group having 1 to 6 carbon atoms;

[0240] Z is a single bond or an alkylene group having 1 to 6 carbon atoms;

[0241] R 2 is a substituent;

[0242] n represents an integer from 0 to 3], and

[0243] (A2) at least one selected from the group consisting of aliphatic aldehydes having 3 to 14 carbon atoms, aromatic aldehydes having 7 to 12 carbon atoms, aliphatic alcohols having 3 to 12 carbon atoms, and substances that generate at least one of these compounds upon heating,

[0244] (B) at least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene-like compounds,

[0245] [Compound Group (C)]

[0246] β-Caryophyllene oxide;

[0247] α-Pinene oxide;

[0248] Limonene oxide;

[0249] α-Terpinenol;

[0250] The compound represented by the general formula (II):

[0251] [Chemistry 23]

[0252]

[0253] 〔In the formula, R 3 and R 4 each independently represents a hydrogen atom, an acyl group having 1 to 18 carbon atoms, or an alkyl group having 1 to 6 carbon atoms];

[0254] The compound represented by the general formula (III):

[0255] [Chemistry 24]

[0256]

[0257] 〔In the formula, R 5 represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms];

[0258] The compound represented by the general formula (IV):

[0259] [Chemistry 25]

[0260]

[0261] 〔In the formula, R 6 represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms];

[0262] The compound represented by the general formula (V):

[0263] [Chemistry 26]

[0264]

[0265] 〔In the formula, R 7 and R 8 each independently represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms]:

[0266] (1S,6S,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecan-5-one,

[0267] (1S,6R,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecan-5-one,

[0268] (1R,4R,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carbaldehyde,

[0269] (1R,4S,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carbaldehyde,

[0270] (1S,2S,5R,9S)-1,4,4,8-tetramethyl-12-oxatricyclo[7.2.1.0 2,5 ] dodec-7-ene,

[0271] (1R,2S,5R,8R,9R)-1,4,4,8-tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ] dodecan-9-ol,

[0272] (1R,2S,5R,8R,9S)-1,4,4,8-tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ] dodecan-9-ol,

[0273] [1R-(1α,2α,5β,8β,9α)]-4,4,8-trimethyl-tricyclo[6.3.1.0 2,5 ]Dodecane-1,9-diol.

[0274]

[42] The coffee roasting enhancer according to

[41] , wherein

[0275] In the general formula (I), R 1 is formyl or acetyl, and Z is a single bond, or

[0276] In the general formula (I), R 1 is hydroxy or pyrrolyl, and Z is methylene.

[0277]

[43] The roasted coffee enhancer according to

[41] or

[42] , wherein R 2It is an alkyl group having 1 to 6 carbon atoms.

[0278]

[44] The roasted coffee enhancer according to any one of

[41] to

[43] , wherein n represents 0 or 1.

[0279]

[45] The roasted coffee enhancer according to any one of

[41] to

[44] , wherein the compound represented by general formula (I) is at least one compound selected from the group consisting of furfural, 5-methylfurfural, 2-furanylmethyl ketone, furfuryl alcohol and 1-furfurylpyrrole.

[0280]

[46] The roasted coffee enhancer according to any one of

[41] to

[45] , wherein (A2) is oil.

[0281]

[47] The roasted coffee enhancer according to any one of

[41] to

[46] , wherein the β-caryophyllene-like compound is at least one compound selected from the group consisting of isocaryophyllene, β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, eugenol, limonene, 4-vinylphenol, linalool, linalool oxide, p-cymene, farnesene, myrcene, ocimene, α-phellandrene, α-terpinene, γ-terpinene and terpinolene (preferably at least one compound selected from the group consisting of β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, eugenol, limonene, 4-vinylphenol, linalool, linalool oxide, p-cymene, farnesene, myrcene, ocimene, α-phellandrene, α-terpinene, γ-terpinene and terpinolene).

[0282]

[48] ​​The coffee roasting enhancer according to

[41] , wherein at least one compound selected from compound group (C) is at least one compound selected from the group consisting of β-caryophyllene oxide, (1R,3Z,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol, (1R,4R,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undecane-4,5-diol, α-pinene oxide, limonene oxide, α-terpinenol, syringabicycloalkanediol, syringabicycloalkanediol-3-monoacetate, syringabicycloalkanediol diacetate and syringabicycloalkanediol-3-monoisovalerate.

[0283]

[49] A method for enhancing a roasted taste of coffee, comprising the step of adding a heated material of (A) and / or (B) described below or at least one compound selected from the following compound group (C).

[0284] (A)(A1) A compound represented by the general formula (I):

[0285] [Chemistry 27]

[0286]

[0287] 〔In the formula,

[0288] R 1 It is an acyl group, a hydroxyl group or a pyrrol group having 1 to 6 carbon atoms;

[0289] Z is a single bond or an alkylene group having 1 to 6 carbon atoms;

[0290] R 2 is a substituent;

[0291] n represents an integer from 0 to 3], and

[0292] (A2) at least one selected from the group consisting of aliphatic aldehydes having 3 to 14 carbon atoms, aromatic aldehydes having 7 to 12 carbon atoms, aliphatic alcohols having 3 to 12 carbon atoms, and substances that generate at least one of these compounds upon heating,

[0293] (B) at least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene-like compounds,

[0294] [Compound Group (C)]

[0295] β-Caryophyllene oxide;

[0296] α-Pinene oxide;

[0297] Limonene oxide;

[0298] α-Terpinenol;

[0299] The compound represented by the general formula (II):

[0300] [Chemistry 28]

[0301]

[0302] 〔In the formula, R 3 and R 4 each independently represents a hydrogen atom, an acyl group having 1 to 18 carbon atoms, or an alkyl group having 1 to 6 carbon atoms];

[0303] The compound represented by the general formula (III):

[0304] [Chemistry 29]

[0305]

[0306] 〔In the formula, R 5represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms];

[0307] The compound represented by the general formula (IV):

[0308] [Chemistry 30]

[0309]

[0310] 〔In the formula, R 6 represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms];

[0311] The compound represented by the general formula (V):

[0312] [Chemistry 31]

[0313]

[0314] 〔In the formula, R 7 and R 8 each independently represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms]:

[0315] (1S,6S,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecan-5-one,

[0316] (1S,6R,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecan-5-one,

[0317] (1R,4R,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carbaldehyde,

[0318] (1R,4S,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carbaldehyde,

[0319] (1S,2S,5R,9S)-1,4,4,8-tetramethyl-12-oxatricyclo[7.2.1.0 2,5 ] dodec-7-ene,

[0320] (1R,2S,5R,8R,9R)-1,4,4,8-tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ] dodecan-9-ol,

[0321] (1R,2S,5R,8R,9S)-1,4,4,8-tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ] dodecan-9-ol,

[0322] [1R-(1α,2α,5β,8β,9α)]-4,4,8-trimethyl-tricyclo[6.3.1.0 2,5 ]Dodecane-1,9-diol.

[0323]

[50] The method for enhancing the roasted taste of coffee according to

[49] , wherein:

[0324] In the general formula (I), R 1 is formyl or acetyl, and Z is a single bond, or

[0325] In the general formula (I), R 1 is hydroxy or pyrrolyl, and Z is methylene.

[0326]

[51] The method for enhancing the roasted taste of coffee according to

[49] or

[50] , wherein R 2 It is an alkyl group having 1 to 6 carbon atoms.

[0327]

[52] The method for enhancing roasted coffee according to any one of

[49] to

[51] , wherein n represents 0 or 1.

[0328]

[53] The method for enhancing the roasted feel of coffee according to any one of

[49] to

[52] , wherein the compound represented by the general formula (I) is at least one compound selected from the group consisting of furfural, 5-methylfurfural, 2-furanylmethyl ketone, furfuryl alcohol and 1-furfurylpyrrole.

[0329]

[54] The method for enhancing roasted coffee according to any one of

[49] to

[53] , wherein (A2) is oil.

[0330]

[55] The method for enhancing the roasted taste of coffee according to any one of

[49] to

[54] , wherein the β-caryophyllene-like compound is at least one compound selected from the group consisting of isocaryophyllene, β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, eugenol, limonene, 4-vinylphenol, linalool, linalool oxide, p-cymene, farnesene, myrcene, ocimene, α-phellandrene, α-terpinene, γ-terpinene and terpinolene (preferably at least one compound selected from the group consisting of β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, eugenol, limonene, 4-vinylphenol, linalool, linalool oxide, p-cymene, farnesene, myrcene, ocimene, α-phellandrene, α-terpinene, γ-terpinene and terpinolene).

[0331]

[56] The method for enhancing the roasted feel of coffee according to

[49] , wherein at least one compound selected from compound group (C) is at least one compound selected from the group consisting of β-caryophyllene oxide, (1R,3Z,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol, (1R,4R,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undecane-4,5-diol, α-pinene oxide, limonene oxide, α-terpinenol, syringabicycloalkanediol, syringabicycloalkanediol-3-monoacetate, syringabicycloalkanediol diacetate and syringabicycloalkanediol-3-monoisovalerate.

[0332] Effects of the Invention

[0333] According to the present invention, a mouth-coating feeling enhancer capable of enhancing the mouth-coating feeling and a method for producing the same can be provided.

[0334] Furthermore, according to the present invention, a food having an enhanced oral coating feeling and a method for producing the same can be provided.

[0335] Furthermore, according to the present invention, a method for enhancing the oral coating feeling can be provided.

[0336] Furthermore, according to the present invention, a coffee roasting enhancer capable of enhancing the roasting sensation of coffee and a method for producing the same can be provided.

[0337] Furthermore, according to the present invention, a coffee beverage having an enhanced coffee roasting sensation and a method for producing the same can be provided.

[0338] Furthermore, according to the present invention, a method for enhancing the roasted taste of coffee can be provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0339] Figure 1 This is a graph showing the results of the two-point discrimination evaluation in Test Example 10. The numerical value in the graph (the vertical axis of the graph) indicates the number of times (n=9) the mouth-coating feeling of the evaluation samples 10-1 and 10-2 was compared under dark evaluation conditions and the mouth-coating feeling was selected as strong. In addition, * in the graph indicates p<0.05.

[0340] Figure 2 This is a graph showing the results of the scoring evaluation in Test Example 10. The numerical values ​​in the graph (the vertical axis of the graph) represent the scores of the sensory evaluation of the intensity of the oral coating feeling of the evaluation samples 10-1 and 10-2 under dark evaluation conditions (average score ± standard error of 3 professional evaluators) (n = 9). In addition, * in the graph indicates p < 0.05. DETAILED DESCRIPTION

[0341] <Oral coating enhancer>

[0342] One of the characteristics of the oral coating feeling enhancer of the present invention is that it contains the following heated product of (A) and / or (B) as an active ingredient, as one embodiment.

[0343] The following (A), (A1), (A2) and (B) used in the present invention may be referred to as "(A) component", "(A1) component", "(A2) component" and "(B) component" in this specification, respectively. In addition, in this specification, a heated product of the (A) component and a heated product of the (B) component may be referred to as "a heated product of the (A) component" and "a heated product of the (B) component", respectively.

[0344] (A)(A1) A compound represented by the general formula (I):

[0345] [Chemistry 32]

[0346]

[0347] 〔In the formula,

[0348] R 1 It is an acyl group, a hydroxyl group or a pyrrol group having 1 to 6 carbon atoms;

[0349] Z is a single bond or an alkylene group having 1 to 6 carbon atoms;

[0350] R 2 is a substituent;

[0351] n represents an integer from 0 to 3]

[0352] as well as

[0353] (A2) at least one selected from the group consisting of aliphatic aldehydes having 3 to 14 carbon atoms, aromatic aldehydes having 7 to 12 carbon atoms, aliphatic alcohols having 3 to 12 carbon atoms, and substances that generate at least one of these compounds upon heating,

[0354] (B) At least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene-like compounds.

[0355] In another embodiment, the oral coating feeling enhancer of the present invention comprises, as an active ingredient, at least one compound selected from the compound group (C) described below.

[0356] At least one compound selected from the compound group (C) used in the present invention may be referred to as "component (C)" in this specification.

[0357] [(A)Component]

[0358] The component (A) of the present invention consists of the component (A1) and the component (A2).

[0359] [(A1) Ingredient]

[0360] In the present invention, the compound represented by the general formula (I) which can be used as the component (A1) may be referred to as "compound (I)" in this specification.

[0361] Next, each group of the general formula (I) is described.

[0362] R in the general formula (I) 1 It represents an acyl group having 1 to 6 carbon atoms, a hydroxyl group or a pyrrolyl group.

[0363] R 1 The "acyl group having 1 to 6 carbon atoms" in the formula (A) may be straight-chain or branched, but is preferably straight-chain. The acyl group may be saturated or contain an unsaturated bond. The number of carbon atoms contained in the acyl group is preferably 1 to 4. Specific examples of the acyl group having 1 to 6 carbon atoms include formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, pivaloyl, hexanoyl, etc., preferably formyl, acetyl, propionyl, butyryl, isobutyryl, more preferably formyl, acetyl, propionyl, and particularly preferably formyl and acetyl.

[0364] R in the general formula (I) 1 It is preferably an acyl group having 1 to 4 carbon atoms, a hydroxyl group or a pyrrolyl group, more preferably a formyl group, an acetyl group, a hydroxyl group or a pyrrolyl group, and particularly preferably a formyl group or an acetyl group.

[0365] Z in the general formula (I) represents a single bond or an alkylene group having 1 to 6 carbon atoms.

[0366] The "alkylene group having 1 to 6 carbon atoms" in Z may be linear or branched, but is preferably linear. The number of carbon atoms contained in the alkylene group is preferably 1 to 4. Specific examples of the alkylene group having 1 to 6 carbon atoms include methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, etc., preferably methylene, ethylene, trimethylene, tetramethylene, more preferably methylene and ethylene, and particularly preferably methylene.

[0367] Z in the general formula (I) is preferably a single bond or an alkylene group having 1 to 4 carbon atoms, and more preferably a single bond or a methylene group.

[0368] Compound (I), in one embodiment, preferably has R 1 is an acyl group having 1 to 6 carbon atoms, and Z is a single bond; more preferably R 1 is an acyl group having 1 to 4 carbon atoms, and Z is a single bond; particularly preferably R 1 is formyl or acetyl, and Z is a single bond.

[0369] In another embodiment, compound (I) is preferably R 1 is hydroxyl or pyrrol, and Z is an alkylene group having 1 to 6 carbon atoms; more preferably R 1 is a hydroxyl group or a pyrrol group, and Z is an alkylene group having 1 to 4 carbon atoms; R 1 is hydroxy or pyrrolyl, and Z is methylene.

[0370] R in the general formula (I) 2 Represents a substituent. 2 The substituent in is not particularly limited, but examples thereof include alkyl groups having 1 to 6 carbon atoms (e.g., methyl, ethyl, propyl, isopropyl, butyl, isobutyl, etc.), cycloalkyl groups having 3 to 8 carbon atoms (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, etc.), alkenyl groups having 2 to 6 carbon atoms (e.g., vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, etc.), alkynyl groups having 2 to 6 carbon atoms (e.g., ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2- The present invention also includes butynyl, 3-butynyl, etc.), acyl having 1 to 6 carbon atoms (e.g., formyl, acetyl, propionyl, butyryl, isobutyryl, etc.), alkoxy having 1 to 6 carbon atoms (e.g., methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, etc.), hydroxyalkyl having 1 to 6 carbon atoms (e.g., hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, etc.), etc., preferably an alkyl having 1 to 6 carbon atoms, more preferably an alkyl having 1 to 4 carbon atoms, and particularly preferably a methyl group.

[0371] n in the general formula (I) represents an integer of 0 to 3. n preferably represents an integer of 0 to 2, and more preferably represents 0 or 1.

[0372] As one embodiment, when n in the general formula (I) is 2 or 3, a plurality of R 2 Can be the same or different.

[0373] Preferred compounds (I) are shown below.

[0374] [Compound (IA)]

[0375] The following compound (I):

[0376] R 1 is formyl, acetyl, hydroxyl or pyrrolyl;

[0377] Z is a single bond or a methylene group;

[0378] R 2 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms);

[0379] n represents an integer of 0 to 3.

[0380] [Compound (IB)]

[0381] The following compound (I):

[0382] R 1 is formyl, acetyl, hydroxyl or pyrrolyl;

[0383] Z is a single bond or a methylene group;

[0384] R 2 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms);

[0385] n represents 0 or 1.

[0386] [Compound (IC)]

[0387] The following compound (I):

[0388] R 1 It is an acyl group or a hydroxyl group having 1 to 6 carbon atoms;

[0389] Z is a single bond or an alkylene group having 1 to 6 carbon atoms;

[0390] R 2 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms); and n is an integer of 0 to 3.

[0391] [Compound (ID)]

[0392] The following compound (I):

[0393] R 1 is formyl, acetyl or hydroxyl;

[0394] Z is a single bond or a methylene group;

[0395] R 2 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms);

[0396] n represents an integer of 0 to 3.

[0397] [Compound (IE)]

[0398] The following compound (I):

[0399] R 1 is formyl, acetyl or hydroxyl;

[0400] Z is a single bond or a methylene group;

[0401] R 2 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms);

[0402] n represents 0 or 1.

[0403] [Compound (IF)]

[0404] The following compound (I):

[0405] R 1 It is an acyl group or a pyrrolyl group having 1 to 6 carbon atoms;

[0406] Z is a single bond or an alkylene group having 1 to 6 carbon atoms;

[0407] R 2 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms);

[0408] n represents an integer of 0 to 3.

[0409] [Compound (IG)]

[0410] The following compound (I):

[0411] R 1 is formyl, acetyl or pyrrolyl;

[0412] Z is a single bond or a methylene group;

[0413] R 2 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms);

[0414] n represents an integer of 0 to 3 (preferably 0 or 1).

[0415] [Compound (IH)]

[0416] The following compound (I):

[0417] R 1 is formyl, acetyl or pyrrolyl;

[0418] Z is a single bond or a methylene group;

[0419] R 2 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms);

[0420] n represents 0 or 1.

[0421] Specific examples of preferred compound (I) include:

[0422] Furfural (CAS registration number: 98-01-1, etc.):

[0423] [Chemistry 33]

[0424]

[0425] 5-Methylfurfural (CAS registration number: 620-02-0):

[0426] [Chemistry 34]

[0427]

[0428] 2-Furanyl methyl ketone (CAS registration number: 1192-62-7, etc.):

[0429] [Chemistry 35]

[0430]

[0431] Furfuryl alcohol (CAS registration number: 98-00-0, etc.):

[0432] [Chemistry 36]

[0433]

[0434] 1-Furfurylpyrrole (CAS registration number: 1438-94-4, etc.):

[0435] [Chemistry 37]

[0436]

[0437] Among them, furfural is preferred because it can obtain clear effects and has good flavor quality.

[0438] The method for producing the component (A1) is not particularly limited, and the component can be produced by a known method or a method based thereon, and may be, for example, a synthetic product or an extract, etc. In addition, commercially available products may be used, which are preferred because of their convenience.

[0439] [(A2) ingredient]

[0440] As the component (A2), in the present invention, an aliphatic aldehyde having 3 to 14 carbon atoms, an aromatic aldehyde having 7 to 12 carbon atoms, or an aliphatic alcohol having 3 to 12 carbon atoms can be used.

[0441] The "aliphatic aldehyde" that can be used as the component (A2) in the present invention may be linear or branched, but is preferably linear. The aliphatic aldehyde may be a saturated aliphatic aldehyde (aliphatic aldehyde having no carbon-carbon double bond or triple bond in the molecule), or may be an unsaturated aliphatic aldehyde (aliphatic aldehyde having a carbon-carbon double bond or triple bond in the molecule), but is preferably an unsaturated aliphatic aldehyde. The number of carbon atoms contained in the aliphatic aldehyde is preferably 3 to 14, more preferably 3 to 12, further preferably 4 to 10, and particularly preferably 6 to 10. Examples of the aliphatic aldehyde that can be used as the component (A2) include propionaldehyde, butyraldehyde, valeraldehyde, 2-pentenal, hexanal, 2-hexenal, 2,4-hexadienal, heptaldehyde, 2,4-heptadienal, octanal, 2-octenal, 2,4-octadienal, nonanal, 2,6-nonadienal, decanal, 2-decenal, 2,4-decadienal, undecanal, 2,4-undecadienal, dodecanal, 2-dodecenal, 2,4-dodecadienal, tridecanal, 2-tridecenal, tetradecanal, 3-(methylthio)propanal (Meth ional), etc., preferably hexanal, 2-hexenal, 2,4-hexadienal, heptaldehyde, 2,4-heptadienal, octanal, 2-octenal, 2,4-octadienal, nonanal, 2,6-nonadienal, decanal, 2-decenal, 2,4-decadienal, undecanal, 2,4-undecadienal, dodecanal, 2-dodecenal, 2,4-dodecadienal, and 3-(methylthio)propanal, and more preferably hexanal, 2-hexenal, octanal, 2-octenal, decanal, 2-decenal, 2,4-decadienal, and 3-(methylthio)propanal.

[0442] The number of carbon atoms contained in the "aromatic aldehyde" that can be used as the component (A2) in the present invention is preferably 7 to 12, more preferably 7 to 10, and particularly preferably 7 to 9. Examples of the aromatic aldehyde that can be used as the component (A2) include benzaldehyde, o-tolualdehyde (2-methylbenzaldehyde), m-tolualdehyde (3-methylbenzaldehyde), p-tolualdehyde (4-methylbenzaldehyde), 4-ethylbenzaldehyde, and 2,6-dimethylbenzaldehyde, among which benzaldehyde, o-tolualdehyde, m-tolualdehyde, and p-tolualdehyde are preferred, and benzaldehyde and p-tolualdehyde are more preferred.

[0443] The "aliphatic alcohol" that can be used as the component (A2) in the present invention may be straight-chain or branched, but is preferably straight-chain. The aliphatic alcohol may be a saturated aliphatic alcohol (an aliphatic alcohol having no carbon-carbon double bond or triple bond in the molecule), or may be an unsaturated aliphatic alcohol (an aliphatic alcohol having a carbon-carbon double bond or triple bond in the molecule), but is preferably a saturated aliphatic alcohol. The number of carbon atoms contained in the aliphatic alcohol is preferably 3 to 12, more preferably 3 to 10, and particularly preferably 6 to 10. The valence of the aliphatic alcohol is not particularly limited, but is preferably 1 to 3, and more preferably 1 or 3. Examples of the aliphatic alcohol that can be used as the component (A2) include propanol, butanol, pentanol, hexanol, 2-hexenol, heptanol, 2-heptenol, 2,4-dimethyl-3-pentanol, octanol, 2-octenol, 2,6-dimethyl-2-heptanol, nonanol, 3-nonenol, decanol, 2-decenol, undecanol, 2-undecenol, dodecanol, 2-dodecenol, glycerol, and trimethylolpropane. Preferred are hexanol, heptanol, octanol, and glycerol, and more preferred are hexanol, octanol, and glycerol.

[0444] As the component (A2), in the present invention, in addition to the above-mentioned aliphatic aldehydes having 3 to 14 carbon atoms, aromatic aldehydes having 7 to 12 carbon atoms and aliphatic alcohols having 3 to 12 carbon atoms, substances that generate at least one of these compounds upon heating can be used.

[0445] The substance that can be used as the (A2) component in the present invention and that generates at least one of an aliphatic aldehyde having 3 to 14 carbon atoms, an aromatic aldehyde having 7 to 12 carbon atoms, and an aliphatic alcohol having 3 to 12 carbon atoms upon heating is not particularly limited as long as it is edible. For example, examples of the substance that generates an aliphatic aldehyde having 3 to 14 carbon atoms upon heating include oils and fats, fatty acids (including saturated fatty acids and unsaturated fatty acids), ketones, lactones, etc., and oils and fats are preferred in terms of obtaining clear effects and good flavor quality.

[0446] In the present invention, "oil" refers to a substance with acylglycerol (triglyceride, diglyceride, monoglyceride, etc.) as the main component. Generally, those that are fluid at room temperature are called "oil" and those that are not fluid are called "fats", but it is a concept that includes both.

[0447] In the present invention, as the fats and oils that can be used as the component (A2), for example, can be cited: vegetable fats and oils such as rapeseed oil, corn oil, soybean oil, sesame oil, rice oil, rice bran oil, safflower oil, coconut oil, palm oil, palm kernel oil, sunflower oil, perilla oil, wild sesame oil, linseed oil, olive oil, grape seed oil, medium-chain fatty acid oil; animal fats and oils such as lard (lard), beef tallow, chicken fat, sheep fat, horse fat, fish oil, whale oil, etc. In addition, ester exchange oils obtained by esterifying the above-mentioned fats and oils, solidified oils obtained by hydrogenating the above-mentioned fats and oils, etc. can also be used. The above-mentioned fats and oils can also be purified fats and oils (such as salad oils, etc.). These fats and oils can be used alone or in combination of two or more.

[0448] The fatty acid that can be used as the component (A2) in the present invention may be any of saturated and unsaturated. The number of carbon atoms contained in the fatty acid is preferably 12 to 24, more preferably 14 to 22, and particularly preferably 16 to 20. Examples of the fatty acid that can be used as the component (A2) include lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, arachidic acid, behenic acid, etc., preferably stearic acid, oleic acid, and linoleic acid.

[0449] The ketone that can be used as the component (A2) in the present invention may be any of saturated and unsaturated. The number of carbon atoms contained in the ketone is preferably 4 to 14, more preferably 6 to 12, and particularly preferably 6 to 10. Examples of the ketone that can be used as the component (A2) include 2-pentanone, 3-pentanone, 2-hexanone, 3-hexanone, 2-heptanone, 3-heptanone, 2-octanone, 3-octanone, 3-methyl-2-heptanone, 5-methyl-3-heptanone, 1-octen-3-one, 2-nonanone, 5-nonanone, 2-undecanone, 6-undecanone, 7-tridecanone, and the like, preferably 3-octanone.

[0450] The heating conditions for producing aliphatic aldehydes having 3 to 14 carbon atoms, aromatic aldehydes having 7 to 12 carbon atoms, and aliphatic alcohols having 3 to 12 carbon atoms by heating are not particularly limited as long as the aliphatic aldehydes can be produced, and can be appropriately set according to the type of the substance, etc. However, the heating temperature is usually 40 to 200°C, preferably 60 to 180°C, and the heating time is usually 0.5 to 480 minutes, preferably 1 to 360 minutes.

[0451] As the component (A2) which can be used in the present invention, preferably, an aliphatic aldehyde having 3 to 14 carbon atoms (e.g., an aliphatic aldehyde having 4 to 10 carbon atoms, etc.), an aromatic aldehyde having 7 to 12 carbon atoms (e.g., an aromatic aldehyde having 7 to 10 carbon atoms, etc.), an aliphatic alcohol having 3 to 12 carbon atoms (e.g., an aliphatic alcohol having 3 to 10 carbon atoms, etc.), oils and fats, fatty acids (e.g., fatty acids having 3 to 14 carbon atoms, etc.), ketones (e.g., Atomic number of 3 to 14 ketones, etc.), more preferably hexanal, 2-hexenal, octanal, 2-octenal, decanal, 2-decenal, 2,4-decadienal, 3-(methylthio)propanal, benzaldehyde, p-tolualdehyde, hexanol, octanol, glycerol, oils and fats (for example, rapeseed oil, soybean oil, corn oil, olive oil, safflower oil, linseed oil, wild sesame oil, hydrogenated palm kernel oil, medium-chain fatty acid oil and other vegetable oils and fats), stearic acid, oleic acid, linoleic acid, 3-octanone.

[0452] When aliphatic aldehydes having 3 to 14 carbon atoms (e.g., aliphatic aldehydes having 4 to 10 carbon atoms), aromatic aldehydes having 7 to 12 carbon atoms (e.g., aromatic aldehydes having 7 to 10 carbon atoms), aliphatic alcohols having 3 to 12 carbon atoms (e.g., aliphatic alcohols having 3 to 10 carbon atoms), fatty acids (e.g., fatty acids having 3 to 14 carbon atoms), or ketones (e.g., ketones having 3 to 14 carbon atoms) are used as the component (A2), the weight ratio of the component (A1) to be heated to the component (A2) is not particularly limited, but is preferably A1:A2=1:0.001 to 1000, more preferably A1:A2=1:0.01 to 100, and particularly preferably A1:A2=1:0.08 to 15.

[0453] In addition, when using oils and fats (e.g., rapeseed oil, soybean oil, corn oil, olive oil, safflower oil, linseed oil, wild sesame oil, hydrogenated palm kernel oil, medium-chain fatty acid oil, etc.) as component (A2), the concentration of component (A1) in the heated oil and fat during heating is preferably 0.0008 to 12000 ppm by weight, more preferably 0.0008 to 1200 ppm by weight, further preferably 0.08 to 120 ppm by weight, and particularly preferably 0.8 to 120 ppm by weight. This concentration, as one embodiment, is preferably 0.0008 to 100000 ppm by weight, more preferably 0.0008 to 50000 ppm by weight, further preferably 0.08 to 10000 ppm by weight, and particularly preferably 0.8 to 5000 ppm by weight.

[0454] The method for producing the component (A2) is not particularly limited, and the component can be produced by a known method or a method based on the method, and may be, for example, a synthetic product or an extract, etc. In addition, commercially available products may be used, which are preferred because of their convenience.

[0455] The method for heating component (A) is not particularly limited. For example, component (A) may be directly heated, or component (A) may be dissolved or dispersed in a medium such as a solvent or a dispersion medium and then heated, that is, component (A) may be heated in the medium. When component (A) is heated in the medium, it may be heated while standing, or it may be heated while stirring as appropriate. In addition, component (A) may also be heated in the presence of a component other than the medium (e.g., component (B) etc.), as long as the purpose of the present invention is not impaired.

[0456] The heating temperature of the component (A) can be appropriately adjusted by the heating time, etc., but is preferably 40 to 200°C, more preferably 50 to 150°C, further preferably 50 to 120°C, and particularly preferably 80 to 120°C, since a heated product of the component (A) having a more excellent effect of enhancing the mouth coating feeling can be obtained.

[0457] The heating time of the component (A) can be appropriately adjusted according to the heating temperature, etc., but is preferably 0.1 to 500 minutes, more preferably 2.5 to 400 minutes, more preferably 3.5 to 150 minutes, and particularly preferably 8 to 100 minutes, because a heated product of the component (A) having a more excellent effect of enhancing the mouth coating feeling can be obtained.

[0458] The heating of the component (A) may be performed under normal pressure or under pressure.

[0459] The heated material of component (A) used in the present invention may be a material obtained by heating component (A) by any method, for example, a material obtained by heating component (A) in a medium, etc. As one embodiment, when component (A) is heated in a medium, the medium used is not particularly limited, but examples thereof include lipids such as sterols, carotenoids, phospholipids, glycolipids, waxes, hydrocarbon oils (such as mineral oils, etc.), ethanol, polyethylene glycol, water, etc.

[0460] When the heated product of component (A) used in the present invention is a product obtained by heating component (A) in a medium, in the component (A) heated to obtain the heated product of component (A), the concentration of component (A1) in the medium during heating is preferably 0.0008 to 12000 ppm by weight, more preferably 0.0008 to 1200 ppm by weight, further preferably 0.08 to 120 ppm by weight, and particularly preferably 0.8 to 120 ppm by weight, because the oral coating feeling can be more effectively enhanced. The concentration, as a mode, is preferably 0.0008 to 100000 ppm by weight, more preferably 0.0008 to 50000 ppm by weight, further preferably 0.08 to 10000 ppm by weight, and particularly preferably 0.8 to 5000 ppm by weight.

[0461] After heating component (A) in a medium, the obtained heated product of component (A) can be separated from the medium for use, or, for example, when the medium used for heating can be used as a food material, the obtained heated product of component (A) can be used together with the medium without being separated from the medium.

[0462] [(B) ingredient]

[0463] The component (B) of the present invention is at least one compound selected from the group consisting of β-caryophyllene (CAS registration number: 87-44-5) and β-caryophyllene-like compounds.

[0464] Examples of the β-caryophyllene-like compound that can be used as the component (B) in the present invention include isocaryophyllene (CAS registration number: 118-65-0), β-pinene (CAS registration number: 127-91-3, 18172-67-3, etc.), sabinene (CAS registration number: 3387-41-5), eugenol (CAS registration number: 97-53-0), limonene (CAS registration number: 5989-27-5, etc.), linalool (CAS registration number: 78-70-6, etc.), linalool oxide (CAS registration number: 60047-17-8, etc.), p-cymene (CAS registration number: 99-87-6, etc.), farnesene (CAS registration number: 14-12-15), and linalool (CAS registration number: 14-12-16). Terpene hydrocarbons such as terpenes (CAS registration number: 502-61-4, 26560-14-5, etc.), myrcene (CAS registration number: 123-35-3, etc.), ocimene (CAS registration number: 13877-91-3, etc.), α-phellandrene (CAS registration number: 99-83-2, etc.), α-terpinene (CAS registration number: 99-86-5), γ-terpinene (CAS registration number: 99-85-4), terpinolene (CAS registration number: 586-62-9, etc.); phenols such as 4-allyl-2,6-dimethoxyphenol (CAS registration number: 6627-88-9), 4-vinylphenol (CAS registration number: 2628-17-3, etc.), etc. These compounds may be used alone or in combination of two or more. The β-caryophyllene-like compound is preferably at least one compound selected from the group consisting of isocaryophyllene, β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, eugenol, limonene, 4-vinylphenol, linalool, linalool oxide, p-cymene, farnesene, myrcene, ocimene, α-phellandrene, α-terpinene, γ-terpinene and terpinolene. Since the oral coating feeling can be effectively improved, it is more preferably selected from the group consisting of At least one compound selected from the group consisting of β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, 4-vinylphenol, linalool oxide, p-cymene, farnesene, myrcene, α-phellandrene, α-terpinene, γ-terpinene and terpinolene, particularly preferably at least one compound selected from the group consisting of β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, myrcene, α-phellandrene and terpinolene.

[0465] The method for producing component (B) is not particularly limited, and it can be produced by a known method or a method based on the method, and may be, for example, a synthetic product or an extract, etc. In addition, commercially available products may be used, which are preferred because of their convenience.

[0466] The method for heating the component (B) is not particularly limited, and may be, for example, the same as the method for heating the component (A) described above, and the preferred aspects thereof are also the same.

[0467] The heating temperature of the component (B) can be appropriately adjusted by the heating time, etc., but is preferably 40 to 200°C, more preferably 50 to 150°C, further preferably 50 to 120°C, and particularly preferably 80 to 120°C, because a heated product of the component (B) having a more excellent effect of enhancing the mouth coating feeling can be obtained.

[0468] The heating time of the component (B) can be appropriately adjusted according to the heating temperature, etc., and is preferably 0.1 to 500 minutes, more preferably 2.5 to 400 minutes, more preferably 3.5 to 150 minutes, and particularly preferably 8 to 100 minutes, because a heated product of the component (B) having a more excellent effect of enhancing the mouth coating feeling can be obtained.

[0469] The heated material of component (B) used in the present invention may be a substance obtained by heating component (B) by any method, for example, a substance obtained by heating component (B) in a medium, etc. As one mode, when component (B) is heated in a medium, the medium used is not particularly limited, but for example, lipids such as oils, fatty acids (such as acetic acid, isovaleric acid, etc.), sterols, carotenoids, phospholipids, glycolipids, waxes, etc.; glycerol, aliphatic alcohols, hydrocarbon oils (such as mineral oils, etc.), ethanol, polyethylene glycol, water, inorganic acids (such as hydrochloric acid, sulfuric acid, etc.). As a medium for heating component (B), component (A2) may also be used. As long as the purpose of the present invention is not impaired, component (B) may also be heated in the presence of components other than the medium (such as component (A), etc.).

[0470] As fats and oils that can be used for heating component (B), for example, can be cited: vegetable fats and oils such as rapeseed oil, corn oil, soybean oil, sesame oil, rice oil, rice bran oil, safflower oil, coconut oil, palm oil, palm kernel oil, sunflower oil, perilla oil, wild sesame oil, linseed oil, olive oil, grape seed oil, medium-chain fatty acid oil; animal fats and oils such as lard (lard), beef tallow, chicken fat, sheep fat, horse fat, fish oil, whale oil, etc. In addition, ester exchange oils obtained by esterifying the above-mentioned fats and oils, solidified oils obtained by hydrogenating the above-mentioned fats and oils, etc. can also be used. The above-mentioned fats and oils can also be purified fats and oils (such as salad oils, etc.). These fats and oils can be used alone or in combination of two or more.

[0471] In the case where the heated product of component (B) used in the present invention is a product obtained by heating component (B) in a medium, since the oral coating feeling can be more effectively enhanced, the concentration of component (B) in the medium during heating is preferably 0.0008 to 12000 ppm by weight, more preferably 0.0008 to 1200 ppm by weight, further preferably 0.08 to 120 ppm by weight, and particularly preferably 0.8 to 120 ppm by weight. The concentration, as a mode, is preferably 0.0008 to 100000 ppm by weight, more preferably 0.0008 to 50000 ppm by weight, further preferably 0.08 to 10000 ppm by weight, and particularly preferably 0.8 to 5000 ppm by weight.

[0472] After heating the component (B) in the medium, the obtained heated product of the component (B) can be separated from the medium and used in the oral coating feeling enhancer of the present invention, or, for example, when the medium used for heating can be used as a food material, the obtained heated product of the component (B) can be used in the oral coating feeling enhancer of the present invention together with the medium without being separated from the medium.

[0473] The oral coating enhancer of the present invention, in one embodiment, comprises a heated product of component (A) and a heated product of component (B) as active ingredients, wherein in component (A) heated to obtain the heated product of component (A), the amount of component (A1) is set to A1. 1 The amount of the component (B) heated to obtain the heated product of the component (B) is referred to as B. 1 (weight), the B 1 With A1 1 The ratio (B 1 :A1 1 ) is preferably in the range of 1:0.00000008 to 12000000, more preferably in the range of 1:0.000008 to 1200000, further preferably in the range of 1:0.008 to 12000, and particularly preferably in the range of 1:0.08 to 1200. Here, A1 1 and B 1 The weight units are the same.

[0474] The oral coating enhancer of the present invention, as one embodiment, contains a heated product of component (A) and a heated product of component (B) as active ingredients, and the heated product of component (A) and component (B) may be products obtained by heating component (A) and component (B) separately, or may be products obtained by heating them together. That is, in this specification, "heated product of component (A) and heated product of component (B)" include: a mixture of heated products of component (A) and component (B) obtained separately, and a heated product obtained by heating component (A) and component (B) together. As "heated product of component (A) and component (B)" obtained by heating component (A) and component (B) together, for example, there can be mentioned: a heated product obtained by heating component (A) and component (B) in a medium, etc.

[0475] [(C) ingredient]

[0476] The component (C) of the present invention is at least one selected from the following compound group (C).

[0477] [Compound Group (C)]

[0478] β-Caryophyllene oxide (CAS registration number: 1139-30-6)

[0479] ·α-Pinene oxide (CAS registration number: 72936-74-4, 19894-99-6)

[0480] ·Limonene oxide (CAS registration number: 1195-92-2, etc.)

[0481] ·α-Terpinenol (CAS registration number: 98-55-5)

[0482] Compounds represented by general formula (II):

[0483] [Chemistry 38]

[0484]

[0485] 〔In the formula, R 3 and R 4 each independently represents a hydrogen atom, an acyl group having 1 to 18 carbon atoms, or an alkyl group having 1 to 6 carbon atoms],

[0486] Compounds represented by general formula (III):

[0487] [Chemistry 39]

[0488]

[0489] 〔In the formula, R 5 represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms],

[0490] Compounds represented by general formula (IV):

[0491] [Chemistry 40]

[0492]

[0493] 〔In the formula, R 6 represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms],

[0494] Compounds represented by general formula (V):

[0495] [Chemistry 41]

[0496]

[0497] 〔In the formula, R 7 and R 8 each independently represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms],

[0498] (1S,6S,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecan-5-one (CAS registration number: 68263-68-3):

[0499] [Chemistry 42]

[0500]

[0501] (1S,6R,9R)-6,10,10-Trimethyl-2-methylenebicyclo[7.2.0]undecan-5-one (CAS registration number: 68330-80-3):

[0502] [Chemistry 43]

[0503]

[0504] (1R,4R,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carbaldehyde (CAS registration number: 151121-36-7):

[0505] [Chemistry 44]

[0506]

[0507] (1R,4S,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carbaldehyde (CAS registration number: 2073828-10-9):

[0508] [Chemistry 45]

[0509]

[0510] ·(1S,2S,5R,9S)-1,4,4,8-tetramethyl-12-oxatricyclo[7.2.1.0 2,5 ] Dodec-7-ene (CAS registration number: 1039439-81-0):

[0511] [Chemistry 46]

[0512]

[0513] ·(1R,2S,5R,8R,9R)-1,4,4,8-Tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ] Dodecan-9-ol (CAS registration number: 1040220-66-3):

[0514] [Chemistry 47]

[0515]

[0516] ·(1R,2S,5R,8R,9S)-1,4,4,8-Tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ] Dodecan-9-ol (CAS registration number: 103189-32-8):

[0517] [Chemistry 48]

[0518]

[0519] ·[1R-(1α,2α,5β,8β,9α)]-4,4,8-trimethyl-tricyclo[6.3.1.0 2,5 ] Dodecane-1,9-diol (CAS registration number: 155485-75-9):

[0520] [Chemistry 49]

[0521]

[0522] (Compound represented by general formula (II))

[0523] Next, each group of the general formula (II) is described.

[0524] R in the general formula (II) 3 and R 4 Each independently represents a hydrogen atom, an acyl group having 1 to 18 carbon atoms, or an alkyl group having 1 to 6 carbon atoms.

[0525] R 3 and R4 The "acyl group having 1 to 18 carbon atoms" in the formula (A) may be straight-chain or branched. The acyl group may be saturated or contain an unsaturated bond. The number of carbon atoms contained in the acyl group is preferably 1 to 5. Specific examples of the acyl group having 1 to 18 carbon atoms include formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, pivaloyl, hexanoyl, caproyl, lauroyl, myristoyl, palmitoyl, stearoyl, etc., preferably formyl, acetyl, propionyl, butyryl, isobutyryl, isovaleryl, more preferably formyl, acetyl, isovaleryl, particularly preferably acetyl and isovaleryl.

[0526] R 3 and R 4 The "alkyl group having 1 to 6 carbon atoms" in the formula (a) may be straight-chain or branched, but is preferably straight-chain. The number of carbon atoms contained in the alkyl group is preferably 1 to 4. Specific examples of the alkyl group having 1 to 6 carbon atoms include methyl, ethyl, propyl, butyl, pentyl, hexyl, etc., preferably methyl, ethyl, propyl, butyl, more preferably methyl and ethyl, and particularly preferably methyl.

[0527] R in the general formula (II) 3 Preferred is a hydrogen atom, an acyl group having 1 to 18 carbon atoms, or an alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom, an acyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 4 carbon atoms, particularly preferably a hydrogen atom, an acetyl group, an isovaleryl group, or a methyl group.

[0528] R in the general formula (II) 4 It is preferably a hydrogen atom or an acyl group having 1 to 18 carbon atoms, more preferably a hydrogen atom or an acyl group having 1 to 5 carbon atoms, and particularly preferably a hydrogen atom or an acetyl group.

[0529] Preferred compounds (II) are shown below.

[0530] [Compound (IIA)]

[0531] The following compound (II):

[0532] R 3 is a hydrogen atom, an acyl group having 1 to 18 carbon atoms, or an alkyl group having 1 to 6 carbon atoms; R 4 It represents a hydrogen atom or an acyl group having 1 to 18 carbon atoms.

[0533] [Compound (IIB)]

[0534] The following compound (II):

[0535] R 3is a hydrogen atom, an acyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 4 carbon atoms; R 4 It represents a hydrogen atom or an acyl group having 1 to 5 carbon atoms.

[0536] [Compound (IIC)]

[0537] The following compound (II):

[0538] R 3 is a hydrogen atom, an acetyl group, an isovaleryl group or a methyl group;

[0539] R 4 represents a hydrogen atom or an acetyl group.

[0540] Specific examples of preferred compound (II) include:

[0541] Syringa tricycloalkanediol (CAS registration number: 2649-64-1):

[0542] [Chemistry 50]

[0543]

[0544] Clove tricycloalkanediol-3-monoacetate (CAS registration number: 127156-28-9):

[0545] [Chemistry 51]

[0546]

[0547] Clove tricycloalkanediol diacetate (CAS registration number: 2649-68-5):

[0548] [Chemistry 52]

[0549]

[0550] Clove tricycloalkanediol-3-monoisovalerate (CAS registration number: 1891070-50-0):

[0551] [Chemistry 53]

[0552]

[0553] 2-Methoxysyringanol (Clovanol) (CAS registration number: 127156-29-0):

[0554] [Chemistry 54]

[0555]

[0556] wait.

[0557] (Compound represented by general formula (III))

[0558] Next, each group of the general formula (III) is described.

[0559] R in the general formula (III) 5 It represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms.

[0560] R 5 The "acyl group having 1 to 6 carbon atoms" in the formula (a) may be straight-chain or branched, but is preferably straight-chain. The acyl group may be saturated or contain an unsaturated bond. The number of carbon atoms contained in the acyl group is preferably 1 to 4. Specific examples of the acyl group having 1 to 6 carbon atoms include formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, pivaloyl, hexanoyl, etc., preferably formyl, acetyl, propionyl, butyryl, isobutyryl, more preferably formyl, acetyl, propionyl, and particularly preferably acetyl.

[0561] R 5 The "alkyl group having 1 to 6 carbon atoms" in the formula (a) may be straight-chain or branched, but is preferably straight-chain. The number of carbon atoms contained in the alkyl group is preferably 1 to 4. Specific examples of the alkyl group having 1 to 6 carbon atoms include methyl, ethyl, propyl, butyl, pentyl, hexyl, etc., preferably methyl, ethyl, propyl, butyl, more preferably methyl and ethyl, and particularly preferably methyl.

[0562] R in the general formula (III) 5 It is preferably a hydrogen atom or an acyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom or an acyl group having 1 to 4 carbon atoms, and particularly preferably a hydrogen atom or an acetyl group.

[0563] The wavy line in the general formula (III) refers to either one of the cis and trans isomers or a mixture of both.

[0564] Specific examples of preferred compound (III) include:

[0565] Caryophyllene II (CAS registration number: 32214-89-4):

[0566] [Chemistry 55]

[0567]

[0568] Caryophyllene alcohol I (CAS registration number: 32214-88-3):

[0569] [Chemistry 56]

[0570]

[0571] (1R,3Z,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol (CAS registration number: 19431-76-6):

[0572] [Chemistry 57]

[0573]

[0574] (1R,3Z,5S,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol (CAS registration number: 19431-77-7):

[0575] [Chemistry 58]

[0576]

[0577] (1R,3EZ,5R,9S)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol-5-acetate

[0578] [Chemistry 59]

[0579]

[0580] wait.

[0581] (Compound represented by general formula (IV))

[0582] Next, each group of the general formula (IV) is described.

[0583] R in the general formula (IV) 6 It represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms.

[0584] R 6 The "acyl group having 1 to 6 carbon atoms" in the formula (a) may be straight-chain or branched, but is preferably straight-chain. The acyl group may be saturated or contain an unsaturated bond. The number of carbon atoms contained in the acyl group is preferably 1 to 4. Specific examples of the acyl group having 1 to 6 carbon atoms include formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, pivaloyl, hexanoyl, etc., preferably formyl, acetyl, propionyl, butyryl, isobutyryl, more preferably formyl, acetyl, propionyl, and particularly preferably acetyl.

[0585] R 6The "alkyl group having 1 to 6 carbon atoms" in the formula (a) may be straight-chain or branched, but is preferably straight-chain. The number of carbon atoms contained in the alkyl group is preferably 1 to 4. Specific examples of the alkyl group having 1 to 6 carbon atoms include methyl, ethyl, propyl, butyl, pentyl, hexyl, etc., preferably methyl, ethyl, propyl, butyl, more preferably methyl and ethyl, and particularly preferably methyl.

[0586] R in the general formula (IV) 6 It is preferably a hydrogen atom or an acyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom or an acyl group having 1 to 4 carbon atoms, and particularly preferably a hydrogen atom or an acetyl group.

[0587] Specific examples of preferred compound (IV) include:

[0588] Caryophyllene glycol II (CAS registration number: 19431-79-9):

[0589] [Chemistry 60]

[0590]

[0591] Caryophyllene glycol I (CAS registration number: 19431-80-2):

[0592] [Chemistry 61]

[0593]

[0594] (1S,5R,9R)-10,10-dimethyl-2,6-dimethoxy-bicyclo[7.2.0]undecane-5-ol acetate (CAS registration number: 99805-59-1):

[0595] [Chemistry 62]

[0596]

[0597] (1S,5S,9R)-10,10-dimethyl-2,6-dimethoxy-bicyclo[7.2.0]undecane-5-ol acetate (CAS registration number: 99881-55-7):

[0598] [Chemistry 63]

[0599]

[0600] wait.

[0601] (Compound represented by general formula (V))

[0602] Next, each group of the general formula (V) is described.

[0603] R in the general formula (V)7 and R 8 Each independently represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms.

[0604] R 7 and R 8 The "acyl group having 1 to 6 carbon atoms" in the formula (a) may be straight-chain or branched, but is preferably straight-chain. The acyl group may be saturated or contain an unsaturated bond. The number of carbon atoms contained in the acyl group is preferably 1 to 4. Specific examples of the acyl group having 1 to 6 carbon atoms include formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, pivaloyl, hexanoyl, etc., preferably formyl, acetyl, propionyl, butyryl, isobutyryl, more preferably formyl, acetyl, propionyl, and particularly preferably acetyl.

[0605] R 7 and R 8 The "alkyl group having 1 to 6 carbon atoms" in the formula may be straight-chain or branched, and is preferably straight-chain. The number of carbon atoms contained in the alkyl group is preferably 1 to 4. Specific examples of the alkyl group having 1 to 6 carbon atoms include methyl, ethyl, propyl, butyl, pentyl, hexyl, etc., preferably methyl, ethyl, propyl, butyl, more preferably methyl, ethyl, and particularly preferably methyl.

[0606] R in the general formula (V) 7 It is preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and particularly preferably a hydrogen atom or a methyl group.

[0607] R in the general formula (V) 8 Preferred is a hydrogen atom.

[0608] Preferred compounds (V) are shown below.

[0609] [Compound (VA)]

[0610] The following compound (V):

[0611] R 7 It is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms;

[0612] R 8 Represents a hydrogen atom.

[0613] [Compound (VB)]

[0614] The following compound (V):

[0615] R 7 It is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;

[0616] R 8 Represents a hydrogen atom.

[0617] [Compound (VC)]

[0618] The following compound (V):

[0619] R 7 is a hydrogen atom or a methyl group;

[0620] R 8 Represents a hydrogen atom.

[0621] Specific examples of preferred compound (V) include:

[0622] (1R,4R,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undecane-4,5-diol (CAS registration number: 187935-72-4):

[0623] [Chemistry 64]

[0624]

[0625] (1R,4S,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undecane-4,5-diol (CAS registration number: 151029-00-4):

[0626] [Chemistry 65]

[0627]

[0628] (1S,5R,6R,9R)-6-methoxy-6,10,10-trimethyl-2-methylene-bicyclo[7.2.0]undecan-5-ol (CAS registration number: 178939-28-1):

[0629] [Chemistry 66]

[0630]

[0631] (1S,5R,6S,9R)-6-methoxy-6,10,10-trimethyl-2-methylene-bicyclo[7.2.0]undecan-5-ol (CAS registration number: 187935-73-5):

[0632] [Chemistry 67]

[0633]

[0634] wait.

[0635] Component (C) is preferably an oxygen-containing terpene derivative such as β-caryophyllene oxide, (1R,3Z,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol, (1R,4R,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undecane-4,5-diol, α-pinene oxide, limonene oxide, α-terpinenol syringabicyclodiol, syringabicyclodiol-3-monoacetate, syringabicyclodiol diacetate and syringabicyclodiol-3-monoisovalerate.

[0636] The manufacturing method of the (C) component is not particularly limited, and can be manufactured by a method known per se or a method based on the method, for example, a synthetic product or an extract, etc. Specifically, the (C) component can be manufactured by the method described in the embodiments described later. In addition, as the (C) component, a commercially available product can also be used, which is preferred because of its simplicity.

[0637] In one embodiment, when the oral coating enhancer of the present invention contains the component (C), the content of the component (C) in the oral coating enhancer of the present invention is preferably 0.00001% by weight or more, more preferably 0.0001% by weight or more, and particularly preferably 0.001% by weight or more, relative to the oral coating enhancer of the present invention. In addition, the content is preferably 100% by weight or less, more preferably 99% by weight or less, and particularly preferably 90% by weight or less, relative to the oral coating enhancer of the present invention.

[0638] The form of the oral coating feeling enhancer of the present invention is not particularly limited, and examples thereof include solid (including powder, granular, etc.), liquid (including slurry, etc.), gel, and paste.

[0639] The oral coating enhancer of the present invention may be, as one embodiment, a substance consisting only of a heated product of component (A) (and a medium for heating component (A) etc.) or a heated product of component (B) (and a medium for heating component (B) etc.). Alternatively, the substance may be a substance consisting only of a heated product of component (A) (and a medium for heating component (A) etc.) and a heated product of component (B) (and a medium for heating component (B) etc.). However, in addition to these heated products, a base commonly used in the form of the oral coating enhancer of the present invention may be contained.

[0640] The oral coating enhancer of the present invention may be composed of the component (C) alone as another embodiment, and may contain a base commonly used in the form of the oral coating enhancer of the present invention.

[0641] When the oral coating feeling enhancer of the present invention is in a liquid form, examples of the base include water, ethanol, glycerin, and propylene glycol.

[0642] When the oral coating enhancer of the present invention is in a solid form, examples of the base include starch, dextrin, cyclodextrin, various sugars such as sucrose and glucose, protein, peptide, salt, solid fat, silicon dioxide and mixtures thereof, yeast cells and various powdered extracts.

[0643] Unless the purpose of the present invention is impaired, the oral coating feeling enhancer of the present invention may further contain, for example, excipients, pH adjusters, antioxidants, thickeners, sweeteners (for example, sugars), acidulants, spices, colorants, etc., in addition to the heated product of component (A) and / or heated product of component (B), or component (C).

[0644] The oral coating enhancer of the present invention can be produced by a known method. The oral coating enhancer of the present invention can be subjected to, for example, concentration treatment, drying treatment, decolorization treatment, etc., alone or in combination.

[0645] The heated product of component (A) and / or component (B) that can be contained in the oral coating enhancer of the present invention is obtained by heating component (A) and / or component (B) as described above, and thus the method for producing the oral coating enhancer of the present invention may include a step of heating component (A) and / or component (B). In the method for producing the oral coating enhancer of the present invention, the method for heating component (A) and component (B) is the same as the method for heating component (A) and component (B) described above, and the preferred embodiment thereof is also the same. In addition, the respective heating temperatures and heating times may be set in the same manner as described above.

[0646] In one embodiment of the method for producing the oral coating enhancer of the present invention, when the step of heating the components (A) and (B) is included, the amount of the component (A1) in the component (A) to be heated is set to A1 4 (weight) and the amount of the component (B) to be heated is set to B 4 (weight), the B 4 With A1 4 The ratio (B 4 :A1 4 ) Just set it in the same way as above B 1 With A1 1 The ratio (B 1 :A1 1 ) are within the same range, and the preferred range is also the same.

[0647] When the method for producing the oral coating enhancer of the present invention includes the step of heating the components (A) and (B), the components (A) and (B) may be heated separately or together. Examples of the method for heating the components (A) and (B) together include a method of dissolving or dispersing both the components (A) and (B) in a medium and then heating them.

[0648] The oral coating enhancer of the present invention can be added to food for use. By adding the oral coating enhancer of the present invention to food, the oral coating sensation of the food can be enhanced.

[0649] In the present invention, "oral coating feeling" refers to the feeling of being covered by a thin film in the oral cavity, the feeling of being covered by a grease or grease-like film in the oral cavity, the smooth feeling felt in the oral cavity, and the grease-like thick feeling (heaviness) spreading throughout the oral cavity, which is clearly felt when the oral cavity contains grease or a grease-containing solution or food. "Enhancement" of the oral coating feeling means that at least one of the above feelings is enhanced. The presence and degree of the oral coating feeling can be evaluated by sensory evaluation by professional evaluators.

[0650] In the present invention, the term "food" refers to a broad concept that includes foods that can be taken orally, and also includes, for example, beverages, seasonings, food additives, and the like.

[0651] The food to which the oral coating feeling enhancer of the present invention can be added may be provided (sold, distributed) in a state suitable for tasting from the source, or may be provided in a state requiring prescribed treatment and cooking to achieve a state suitable for tasting. For example, the food to which the oral coating feeling enhancer of the present invention can be added may be provided as a concentrate that needs to be diluted with water or the like to achieve a state suitable for tasting.

[0652] The food to which the oral coating enhancer of the present invention can be added is not particularly limited as long as it is a food that can have the desired oral coating feeling, and examples thereof include: fats (e.g., vegetable fats, animal fats, etc.), mayonnaise, soups, seasonings, curry fried foods, snacks, chocolate, biscuits, bread, fat-containing milk and dairy products (e.g., raw milk, milk, low-fat milk, cream, butter, margarine, spreads, cheese, yogurt, etc.), fat-containing beverages, fat-containing noodles (e.g., fried noodles, etc.) and other fat-free foods; oil-free seasonings, fat-free milk and dairy products (fat-free milk, skim milk powder, fat-free milk), fat-free beverages (e.g., coffee drinks, etc.), fat-free noodles (e.g., non-fried noodles, raw noodles, pasta, noodles), etc. Here, the fat-containing food may be a food containing only fat, that is, the fat-containing food may also be fat itself.

[0653] The oral coating enhancer of the present invention can significantly enhance the oral coating sensation felt by the fat in the oral cavity, and is therefore preferably added to fat-containing foods for use, that is, the oral coating enhancer of the present invention is preferably used in fat-containing foods.

[0654] The fats and oils contained in the fat-containing food that can be used in the oral coating enhancer of the present invention are not particularly limited as long as they are edible, and examples thereof include: vegetable fats and oils such as rapeseed oil, corn oil, soybean oil, sesame oil, rice oil, rice bran oil, safflower oil, coconut oil, palm oil, palm kernel oil, sunflower oil, perilla oil, wild sesame oil, linseed oil, olive oil, grape seed oil, medium-chain fatty acid oil; animal fats and oils such as lard (lard), beef tallow, chicken fat, sheep fat, horse fat, fish oil, whale oil, and milk fat. In addition, ester-transesterified oils obtained by transesterifying the above-mentioned fats and oils, and solidified oils obtained by hydrogenating the above-mentioned fats and oils, etc., can also be used. The above-mentioned fats and oils can also be purified fats and oils (such as salad oils, etc.). These fats and oils can be used alone or in combination of two or more.

[0655] The content of fat in the fat-containing food to which the oral coating enhancer of the present invention can be used is not particularly limited, but is preferably 0.1 to 100% by weight, more preferably 0.5 to 100% by weight, in order to more clearly exhibit the effect.

[0656] The method and conditions for adding the oral coating enhancer of the present invention to food are not particularly limited, and can be appropriately set according to the form of the oral coating enhancer of the present invention and the type of food. The timing for adding the oral coating enhancer of the present invention to food is not particularly limited, and it can be added at any time point, for example, during the production of the food, after the food is completed (just before tasting the food, during tasting the food, etc.). The oral coating enhancer of the present invention can also be added to the raw materials before the food is produced.

[0657] In one embodiment, when the oral coating enhancer of the present invention contains the component (C), the oral coating enhancer of the present invention is added to the food in such a manner that the amount of the component (C) added to the food is preferably 0.0001 ppm by weight or more, more preferably 0.0005 ppm by weight or more, and particularly preferably 0.001 ppm by weight or more, relative to the food. In this case, the oral coating enhancer of the present invention can be added to the food in such a manner that the amount of the component (C) added to the food is preferably 100 ppm by weight or less, more preferably 50 ppm by weight or less, and particularly preferably 10 ppm by weight or less, relative to the food.

[0658] <Methods to enhance the feeling of oral coating>

[0659] The present invention also provides a method for enhancing a coating sensation in the oral cavity, comprising the step of adding a heated product of component (A) and / or a heated product of component (B).

[0660] In addition, the present invention also provides a method for enhancing the coating feeling in the oral cavity, which comprises the step of adding component (C).

[0661] In this specification, these methods may be collectively referred to as "the method for enhancing the oral coating feeling of the present invention".

[0662] The heated product of component (A) and / or component (B) that can be used in the method for enhancing the oral coating feeling of the present invention is the same as the heated product of component (A) and / or component (B) that can be contained in the oral coating feeling enhancing agent of the present invention, and the preferred embodiments are also the same. In addition, these can also be produced in the same manner as the above method.

[0663] The component (C) that can be used in the method for enhancing the mouth-coating feeling of the present invention is the same as the component (C) that can be contained in the agent for enhancing the mouth-coating feeling of the present invention, and the preferred embodiment is also the same.

[0664] In one embodiment of the method for enhancing the oral coating feeling of the present invention, when the heated product of the component (A) and the heated product of the component (B) are added, the amount of the component (A1) in the component (A) heated to obtain the heated product is set to A1. 2 (weight) and the amount of the component (B) heated to obtain the heated product is referred to as B 2 (weight), the B 2 With A1 2 The ratio (B 2 :A1 2 ) Just set it in the same way as above B 1 With A1 1 The ratio (B 1 :A1 1 ) are within the same range, and the preferred range is also the same.

[0665] The heated product of component (A) and / or component (B) that can be used in the method for enhancing the oral coating feeling of the present invention is obtained by heating component (A) and / or component (B), respectively, as described above. Therefore, the method for enhancing the oral coating feeling of the present invention may include a step of heating component (A) and / or component (B), and a step of adding the obtained heated product of component (A) and / or heated product of component (B).

[0666] According to the method for enhancing the oral coating feeling of the present invention, the oral coating feeling of a food can be enhanced. Examples of foods to which the oral coating feeling can be enhanced by the method for enhancing the oral coating feeling of the present invention include the same foods as those exemplified as foods to which the oral coating feeling enhancer of the present invention can be added, and preferred foods are also the same.

[0667] The method for enhancing the oral coating sensation of the present invention can significantly enhance the oral coating sensation felt by fats and oils in the oral cavity, and is therefore preferably a method for enhancing the oral coating sensation of fat-containing foods.

[0668] In the method for enhancing the oral coating feeling of the present invention, the method and conditions for adding the heated product of component (A) and / or component (B) are not particularly limited and can be appropriately set according to the type of food, etc. The time for adding the heated product of component (A) and / or component (B) is not particularly limited and can be added at any time point, for example, during the manufacture of the food, after the food is completed (just before tasting the food, during tasting the food, etc.). The heated product of component (A) and / or component (B) can also be added to the raw materials before manufacturing the food.

[0669] In the method for enhancing the oral coating feeling of the present invention, the method and conditions for adding the component (C) are not particularly limited and can be appropriately set according to the type of food, etc. The timing for adding the component (C) is not particularly limited and can be added at any time, for example, during the production of the food, after the food is completed (just before tasting the food, during tasting the food, etc.), etc. The component (C) can also be added to the raw materials before the food is produced.

[0670] In the method for enhancing the mouth coating feeling of the present invention, the addition of the component (C) may be carried out so that the amount of the component (C) added to the food is the same as the amount of the component (C) added to the food when the mouth coating feeling enhancer of the present invention is added to the food (described above).

[0671] <Food production method>

[0672] The present invention also provides a method for producing a food, comprising the step of adding a heated product of component (A) and / or a heated product of component (B).

[0673] Furthermore, the present invention provides a method for producing a food, comprising the step of adding component (C).

[0674] In this specification, these production methods may be collectively referred to as "the production method of the present invention".

[0675] The heated product of component (A) and / or component (B) that can be used in the production method of the present invention is the same as the heated product of component (A) and / or component (B) that can be contained in the oral coating feeling enhancer of the present invention, and the preferred embodiments are also the same. In addition, these can also be produced in the same manner as the above method.

[0676] The component (C) that can be used in the production method of the present invention is the same as the component (C) that can be contained in the oral coating feeling enhancer of the present invention, and the preferred embodiment is also the same. In addition, these can also be produced in the same manner as the above method.

[0677] When the production method of the present invention includes the steps of adding the heated product of component (A) and the heated product of component (B), in the component (A) heated to obtain the heated product, the amount of component (A1) is set to A1. 3 (weight) and the amount of the component (B) heated to obtain the heated product is referred to as B 3 (weight), the B 3 With A1 3 The ratio (B 3 :A1 3 ) can be set in the same way as above B 1 With A1 1 The ratio (B 1 :A1 1 ) are in the same range, the preferred range is also the same.

[0678] The heated product of component (A) and / or component (B) that can be used in the manufacturing method of the present invention is obtained by heating component (A) and / or component (B) respectively as described above, so the manufacturing method of the present invention may include a step of heating component (A) and / or component (B). In addition, the manufacturing method of the present invention may include a step of adding the obtained heated product of component (A) and / or heated product of component (B).

[0679] In the manufacturing method of the present invention, the method and conditions for adding the heated product of component (A) and / or component (B) are not particularly limited, and can be appropriately set according to the type of food to be manufactured. The period for adding the heated product of component (A) and / or component (B) is not particularly limited, and can be added at any time point from the start of the manufacture of the food to the completion. In addition, the heated product of component (A) and / or component (B) can also be added to the raw materials before manufacturing the food.

[0680] In the manufacturing method of the present invention, the method and conditions for adding the (C) component are not particularly limited and can be appropriately set according to the type of food, etc. The period for adding the (C) component is not particularly limited and can be added at any time point from the start to the completion of the manufacture of the food. In addition, the (C) component can also be added to the raw materials before manufacturing the food.

[0681] In the production method of the present invention, the addition of component (C) can be performed so that the amount of component (C) added to the food becomes the same as the amount of component (C) added to the food when the mouth coating feeling enhancer of the present invention is added to the food (described above).

[0682] The manufacturing method of the present invention may include, in addition to the steps of adding the heated product of component (A) and / or the heated product of component (B), or adding component (C), appropriately including processing steps and cooking steps commonly used in the manufacture of food, depending on the type of food to be manufactured.

[0683] According to the production method of the present invention, a food containing a heated product of component (A) and / or a heated product of component (B), or component (C) can be produced, and preferably a food containing a heated product of component (A) and / or a heated product of component (B), or component (C) with an enhanced oral coating feeling can be produced. Examples of foods that can be produced by the production method of the present invention include the same foods as those exemplified as foods to which the oral coating feeling enhancer of the present invention can be added, and preferred foods are also the same.

[0684] The production method of the present invention is preferably a method for producing a fat-containing food, and more preferably a method for producing a fat-containing food having an enhanced coating feeling in the mouth.

[0685] <Coffee roasting enhancer>

[0686] One of the characteristics of the roasted coffee enhancer of the present invention is that it contains a heated product of the component (A) and / or the component (B) as an active ingredient, as one embodiment.

[0687] The heated product of component (A) and / or component (B) that can be contained in the roasted coffee enhancer of the present invention is the same as the heated product of component (A) and / or component (B) that can be contained in the mouth coating enhancer of the present invention, and the preferred embodiments are also the same. In addition, these can also be produced in the same manner as the above method.

[0688] The roasted coffee taste enhancer of the present invention, as another embodiment, is characterized in that it contains component (C) as an active ingredient.

[0689] The component (C) that can be contained in the roasted coffee enhancer of the present invention is the same as the component (C) that can be contained in the mouth coating enhancer of the present invention, and the preferred embodiment is also the same. In addition, the production thereof can be carried out in the same manner as the above method.

[0690] When the roasted coffee enhancer of the present invention includes a heated product of component (A), the heating temperature of component (A) is preferably 80 to 150° C., more preferably 80 to 130° C., and particularly preferably 85 to 120° C., because it can effectively enhance the roasted coffee. In this case, the heating time of component (A) is preferably 5 to 150 minutes, more preferably 10 to 120 minutes, and particularly preferably 20 to 100 minutes, because it can effectively enhance the roasted coffee.

[0691] When the roasted coffee enhancer of the present invention includes a heated product of component (B), the heating temperature of component (B) is preferably 70 to 150° C., more preferably 80 to 130° C., and particularly preferably 85 to 120° C., since it can effectively enhance the roasted coffee. In this case, the heating time of component (B) is preferably 5 to 150 minutes, more preferably 10 to 120 minutes, and particularly preferably 20 to 100 minutes, since it can effectively enhance the roasted coffee.

[0692] The form of the roasted coffee enhancer of the present invention, the amount of the heated product of component (A) and / or the heated product of component (B) that can be contained in the roasted coffee enhancer of the present invention, and the base that can be contained in the roasted coffee enhancer of the present invention are the same as those of the mouth coating enhancer of the present invention.

[0693] When the roasted coffee texture enhancer of the present invention contains the component (C), the content of the component (C) and the amount of the component (C) added to the food are the same as those of the mouth coating texture enhancer of the present invention.

[0694] The coffee roasting enhancer of the present invention comprises, as one embodiment, a heated product of component (A) and a heated product of component (B), wherein in the component (A) heated to obtain the heated product of component (A), the amount of component (A1) is set to A1. 1 The amount of the component (B) heated to obtain the heated product of the component (B) is referred to as B. 1 (weight), the B 1 With A1 1 The ratio (B 1 :A1 1 ) can effectively enhance the roasted feeling of coffee, so it is preferably in the range of 1:1 to 10, more preferably in the range of 1:1 to 8, and particularly preferably in the range of 1:1 to 6. Here, A1 1 and B 1The weight units are the same.

[0695] The production of the roasted coffee texture enhancer of the present invention can be carried out in the same manner as the production of the mouth coating texture enhancer of the present invention, and the preferred embodiments thereof are also the same.

[0696] The method for producing the roasted coffee enhancer of the present invention, in one embodiment, comprises the step of heating the components (A) and (B), wherein the amount of the component (A1) in the component (A) to be heated is set to A1 4 (weight) and the amount of the component (B) to be heated is set to B 4 (weight), the B 4 With A1 4 The ratio (B 4 :A1 4 ) can effectively enhance the roasted feeling of coffee, so it is preferably in the range of 1:1 to 10, more preferably in the range of 1:1 to 8, and particularly preferably in the range of 1:1 to 6. Here, A1 4 and B 4 The weight units are the same.

[0697] The roasted coffee enhancer of the present invention can be added to coffee beverages for use. By adding the roasted coffee enhancer of the present invention to coffee beverages, the roasted taste of the coffee beverages can be enhanced.

[0698] In the present invention, "roasted coffee taste" refers to coffee-like fragrance and bitterness. "Enhancement" of roasted coffee taste means that at least one of the coffee-like fragrance and bitterness is enhanced. The presence and degree of roasted coffee taste can be evaluated by sensory evaluation by professional evaluators.

[0699] In addition, in the present invention, "coffee beverage" refers to a beverage that uses coffee bean-derived ingredients as one of the raw materials. Here, as coffee bean-derived ingredients, for example, there can be mentioned: a liquid extracted from ground roasted coffee beans with water or warm water (coffee extract), instant coffee powder obtained by drying the coffee extract, commercially available instant coffee powder, commercially available deep-roasted coffee (espresso liquid), etc. Coffee beverages may contain ingredients other than coffee bean-derived ingredients (e.g., milk, dairy products, sweeteners, etc.).

[0700] The coffee roasting enhancer of the present invention can also enhance the milky taste. In the present invention, "milky taste" refers to the milk-like aroma and sweetness. "Enhancement" of the milky taste means that at least one of the milk-like aroma and sweetness is enhanced. The presence and degree of the milky taste can be evaluated by sensory evaluation of professional evaluators.

[0701] The method and conditions for adding the roasted coffee enhancer of the present invention to the coffee beverage are not particularly limited, and can be appropriately set according to the form of the roasted coffee enhancer of the present invention, etc. The time when the roasted coffee enhancer of the present invention is added to the coffee beverage is not particularly limited, and can be added at any time, for example, during the production of the coffee beverage, after the coffee beverage is completed (immediately before drinking the coffee beverage, during drinking the coffee beverage, etc.), etc.

[0702] <How to enhance the roasted taste of coffee>

[0703] The present invention also provides a method for enhancing a roasted taste of coffee, comprising the step of adding a heated object as component (A) and / or a heated object as component (B).

[0704] In addition, the present invention also provides a method for enhancing the roasted taste of coffee, which comprises the step of adding component (C).

[0705] In this specification, these methods may be collectively referred to as "the method for enhancing roasted coffee taste of the present invention".

[0706] The heated product of component (A) and / or component (B) that can be used in the method for enhancing roasted coffee texture of the present invention is the same as the heated product of component (A) and / or component (B) that can be contained in the oral coating enhancer or roasted coffee enhancer of the present invention, and the preferred embodiments are also the same. In addition, these can also be produced in the same manner as the above method.

[0707] The component (C) that can be used in the method for enhancing the roasted coffee texture of the present invention is the same as the component (C) that can be contained in the mouth coating enhancer or the roasted coffee enhancer of the present invention, and the preferred embodiment is also the same. In addition, the production thereof can also be carried out in the same manner as the above method.

[0708] Unless otherwise specified, the method for enhancing the roasted coffee taste of the present invention can be carried out in the same manner as the method for enhancing the mouth-coating feeling of the present invention. The method for enhancing the roasted coffee taste of the present invention can include the steps of heating the component (A) and / or the component (B) and adding the heated product of the component (A) and / or the heated product of the component (B), similarly to the method for enhancing the mouth-coating feeling of the present invention.

[0709] In one embodiment of the method for enhancing roasted coffee of the present invention, when the method comprises the steps of adding a heated product of component (A) and a heated product of component (B), in component (A) heated to obtain the heated product, the amount of component (A1) is set to A1. 2 (weight) and the amount of the component (B) heated to obtain the heated product is referred to as B 2 (weight), the B 2With A1 2 The ratio (B 2 :A1 2 ) can effectively enhance the roasted feeling of coffee, so it is preferably in the range of 1:1 to 10, more preferably in the range of 1:1 to 8, and particularly preferably in the range of 1:1 to 6. Here, A1 2 and B 2 The weight units are the same.

[0710] According to the coffee roasting feeling enhancement method of the present invention, the coffee roasting feeling of the coffee beverage can be enhanced. In addition, the milk feeling of the coffee beverage can be enhanced.

[0711] In the method for enhancing roasted coffee taste of the present invention, the time when the heated product of component (A) and / or component (B) is added to the coffee beverage is not particularly limited, and the product may be added at any time, for example, during the production of the coffee beverage, after the coffee beverage is completed (just before the coffee beverage is consumed, during the consumption of food, etc.). The heated product of component (A) and / or component (B) may also be added to the raw materials before the coffee beverage is produced.

[0712] <Coffee beverage production method>

[0713] The present invention also provides a method for producing a coffee beverage, which includes the step of adding a heated material as component (A) and / or a heated material as component (B).

[0714] In addition, the present invention also provides a method for producing a coffee beverage, which includes the step of adding component (C).

[0715] In this specification, these production methods may be collectively referred to as "the production method of the coffee beverage of the present invention".

[0716] The heated product of component (A) and / or component (B) that can be used in the method for producing a coffee beverage of the present invention is the same as the heated product of component (A) and / or component (B) that can be contained in the mouth coating enhancer or coffee roasting enhancer of the present invention, and the preferred embodiments are also the same. In addition, these can also be produced in the same manner as the above method.

[0717] The component (C) that can be used in the method for producing the coffee beverage of the present invention is the same as the component (C) that can be contained in the mouth coating enhancer or the coffee roasting enhancer of the present invention, and the preferred embodiment is also the same. In addition, the production thereof can also be carried out in the same manner as the above method.

[0718] Unless otherwise specified, the method for producing the coffee beverage of the present invention can be carried out in the same manner as the method for producing the coffee beverage of the present invention. The method for producing the coffee beverage of the present invention can include the steps of adding the heated component (A) and / or the component (B) and the step of adding the obtained heated product of the component (A) and / or the heated product of the component (B), similarly to the method for producing the coffee beverage of the present invention.

[0719] When the method for producing a coffee beverage of the present invention includes the steps of adding a heated product of component (A) and a heated product of component (B), in component (A) heated to obtain the heated product, the amount of component (A1) is set to A1. 3 (weight) and the amount of the component (B) heated to obtain the heated product is referred to as B 3 (weight), the B 3 With A1 3 The ratio (B 3 :A1 3 ) can effectively enhance the roasted feeling of coffee, so it is preferably in the range of 1:1 to 10, more preferably in the range of 1:1 to 8, and particularly preferably in the range of 1:1 to 6. Here, A1 3 and B 3 The weight units are the same.

[0720] According to the method for producing a coffee beverage of the present invention, a coffee beverage containing a heated product of component (A) and / or a heated product of component (B), or component (C) can be produced. Preferably, a coffee beverage containing a heated product of component (A) and / or a heated product of component (B) or component (C) with an enhanced roasted coffee taste can be produced. More preferably, a coffee beverage containing a heated product of component (A) and / or a heated product of component (B) or component (C) with an enhanced roasted coffee taste and milk taste can be produced.

[0721] The present invention is described in more detail in the following examples, but the present invention is not limited to these examples. In addition, when "%" or "ppm" is recorded in this specification, it means "weight %" or "weight ppm" unless otherwise specified.

[0722] Example

[0723] (Test Example 1)

[0724] <Positive and negative controls>

[0725] For the positive control, a product obtained by adding 1% by weight of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) to a common commercially available mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "PureSelect (registered trademark) mayonnaise", oil content: 73%) was used.

[0726] For the negative control, a product obtained by adding 1 wt % of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) to a commercially available mayonnaise having a lower fat content than that of the positive control mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "Pure Select (registered trademark) Kokuuma (registered trademark) 65% Calorie Reduction", fat content: 23%) was used.

[0727] <Evaluation samples 1-1 to 1-4>

[0728] β-Caryophyllene and furfuryl alcohol or furfural (both manufactured by Sigma-Aldrich) were added to safflower oil (manufactured by Ajinomoto Co., Ltd.) and dissolved at the concentrations shown in Table 1 below (β-Caryophyllene: 10 ppm relative to safflower oil; furfuryl alcohol: 100 ppm relative to safflower oil; furfural: 1 to 100 ppm relative to safflower oil), and then the safflower oil was heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikaki Co., Ltd.). 1 wt % of each heated safflower oil was added to the commercially available mayonnaise used in the preparation of the negative control instead of adding unheated safflower oil, and the obtained mayonnaise was used as evaluation samples 1-1 to 1-4.

[0729] <Sensory Evaluation>

[0730] The evaluation of the oral coating feeling was scored as follows: 3 professional evaluators tasted the mayonnaise of the positive control, negative control and evaluation sample, scored "5.0 points" for the positive control and "0.0 points" for the negative control, and evaluated the evaluation sample within the range of 0.0 to 5.0 points with a minimum interval of 0.1 point.

[0731] The results are shown in Table 1 below.

[0732] [Table 1]

[0733]

[0734] It can be seen from the results in Table 1 that the oral coating feeling of each evaluation sample is effectively enhanced by heating the (A) component and / or the (B) component (specifically, the heated product of β-caryophyllene, furfural and safflower oil; the heated product of β-caryophyllene, furfural and safflower oil).

[0735] (Test Example 2)

[0736] <Positive and negative controls>

[0737] For the positive control, 1% by weight of unheated mineral oil (manufactured by Kaneda Corporation) was added to a common commercially available mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name “PureSelect (registered trademark) mayonnaise”, fat content: 73%).

[0738] For the negative control, a product obtained by adding 1 wt % of unheated mineral oil (manufactured by KANEDA Co., Ltd.) to a commercially available mayonnaise having a lower fat content than the mayonnaise of the positive control (manufactured by Ajinomoto Co., Ltd., trade name "Pure Select (registered trademark) Kokuuma (registered trademark) 65% Calorie Reduction", fat content: 23%) was used.

[0739] <Evaluation samples 2-1 to 2-4>

[0740] β-Caryophyllene, 2-hexenal, and furfuryl alcohol or furfural (all manufactured by Sigma-Aldrich) were added to mineral oil (manufactured by Kaneda Co., Ltd.) and dissolved at the concentrations shown in Table 2 below (β-Caryophyllene: 10 ppm relative to mineral oil; furfuryl alcohol: 100 ppm relative to mineral oil; furfural: 1 to 100 ppm relative to mineral oil; 2-hexenal: 10 ppm relative to mineral oil), and then the mineral oil was heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikaki Co., Ltd.). 1 wt % of each heated mineral oil was added to the commercially available mayonnaise used in the preparation of the negative control instead of adding unheated mineral oil, and the obtained mayonnaise was used as evaluation samples 2-1 to 2-4.

[0741] <Sensory Evaluation>

[0742] The evaluation of the oral coating feeling was performed in the same manner as in Test Example 1.

[0743] The results are shown in Table 2 below.

[0744] [Table 2]

[0745]

[0746] It can be seen from the results in Table 2 that the oral coating feeling of each evaluation sample is effectively enhanced by heating the (A) component and / or the (B) component (specifically, the heated product of β-caryophyllene, furfural and 2-hexenal; the heated product of β-caryophyllene, furfural and 2-hexenal).

[0747] (Test Example 3)

[0748] <Positive and negative controls>

[0749] For the positive control, a product obtained by adding 0.001 to 1% by weight of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) to a common commercially available mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "PureSelect (registered trademark) mayonnaise", oil content: 73%) was used.

[0750] For the negative control, a product obtained by adding 0.001 to 1% by weight of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) to a commercially available mayonnaise having a lower fat content than that of the positive control mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "Pure Select (registered trademark) Kokuuma (registered trademark) 65% Calorie Reduction", fat content: 23%) was used.

[0751] <Evaluation samples 3-1 to 3-11>

[0752] β-Caryophyllene and furfural (both manufactured by Sigma-Aldrich) were added to safflower oil (manufactured by Ajinomoto Co., Ltd.) and dissolved at the concentrations shown in Table 3 below (β-Caryophyllene: 10 to 10,000 ppm relative to safflower oil; furfural: 10 to 10,000 ppm relative to safflower oil), and the safflower oil was heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikaki Co., Ltd.). 0.001 to 1% by weight of each heated safflower oil was added to the commercially available mayonnaise used in the preparation of the negative control instead of adding unheated safflower oil, and the obtained mayonnaise was used as evaluation samples 3-1 to 3-11.

[0753] <Sensory Evaluation>

[0754] The evaluation of the oral coating feeling was performed in the same manner as in Test Example 1.

[0755] The results are shown in Table 3 below.

[0756] [Table 3]

[0757]

[0758] The results in Table 3 show that the heated product of component (A) and / or heated product of component (B) (specifically, the heated product of β-caryophyllene, furfural and safflower oil) effectively enhances the coating feeling in the mouth of each evaluation sample.

[0759] (Test Example 4)

[0760] <Positive and negative controls>

[0761] For the positive control, a product obtained by adding 0.001 to 1% by weight of unheated mineral oil (manufactured by Kaneda Corporation) to a common commercially available mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "PureSelect (registered trademark) mayonnaise", oil content: 73%) was used.

[0762] For the negative control, a product obtained by adding 0.001 to 1% by weight of unheated mineral oil (manufactured by Kaneda Co., Ltd.) to a commercially available mayonnaise having a lower fat content than that of the positive control mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "Pure Select (registered trademark) Kokuuma (registered trademark) 65% Calorie Reduction", fat content: 23%) was used.

[0763] <Evaluation samples 4-1 to 4-11>

[0764] β-Caryophyllene, furfural and 2-hexenal (all manufactured by Sigma-Aldrich) were added to mineral oil (manufactured by Kaneda Co., Ltd.) and dissolved at the concentrations shown in Table 4 below (β-Caryophyllene: 10 to 10000 ppm relative to mineral oil; furfural: 10 to 10000 ppm relative to mineral oil; 2-hexenal: 10 to 10000 ppm relative to mineral oil), and then the mineral oil was heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikaki Co., Ltd.). 0.001 to 1% by weight of each heated mineral oil was added to the commercially available mayonnaise used in the preparation of the negative control instead of adding unheated mineral oil, and the obtained mayonnaise was used as evaluation samples 4-1 to 4-11.

[0765] <Sensory Evaluation>

[0766] The evaluation of the oral coating feeling was performed in the same manner as in Test Example 1.

[0767] The results are shown in Table 4 below.

[0768] [Table 4]

[0769]

[0770] The results in Table 4 show that the heated product of component (A) and / or the heated product of component (B) (specifically, the heated product of β-caryophyllene, furfural and 2-hexenal) effectively enhances the mouth coating feeling of each evaluation sample.

[0771] (Test Example 5-1)

[0772] <Positive and negative controls>

[0773] For the positive control, a product obtained by adding 0.2% by weight of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) to a common commercially available mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "PureSelect (registered trademark) mayonnaise", oil content: 73%) was used.

[0774] For the negative control, a product obtained by adding 0.2% by weight of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) to a commercially available mayonnaise having a lower fat content than that of the positive control mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "Pure Select (registered trademark) Kokuuma (registered trademark) 65% Calorie Reduction", fat content: 23%) was used.

[0775] <Evaluation samples 5-1 to 5-8>

[0776] β-Caryophyllene and furfural (both manufactured by Sigma-Aldrich) were added to safflower oil (manufactured by Ajinomoto Co., Ltd.) and dissolved at the concentrations shown in Table 5 below (β-Caryophyllene: 100 ppm relative to safflower oil; furfural: 100 ppm relative to safflower oil), and then the safflower oil was heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikakigi Co., Ltd.). 0.1 wt % of the heated safflower oil was added to the commercially available mayonnaise used in the preparation of the negative control, and 0.1 wt % of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) was further added to obtain the mayonnaise as Evaluation Sample 5-1.

[0777] Furfural (manufactured by Sigma-Aldrich) was added to safflower oil (manufactured by Ajinomoto Co., Ltd.) and dissolved in a concentration shown in Table 5 below (100 ppm relative to safflower oil), and then the safflower oil was heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikakigi Co., Ltd.). 0.1% by weight of the heated safflower oil was added to the commercially available mayonnaise used in the preparation of the negative control, and 0.1% by weight of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) was further added to obtain the mayonnaise, which was used as Evaluation Sample 5-2.

[0778] β-Caryophyllene (manufactured by Sigma-Aldrich) was added to safflower oil (manufactured by Ajinomoto Co., Ltd.) and dissolved at the concentration shown in Table 5 below (100 ppm relative to safflower oil), and then the safflower oil was heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikakigi Co., Ltd.). 0.1% by weight of the heated safflower oil was added to the commercially available mayonnaise used in the preparation of the negative control, and 0.1% by weight of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) was further added to obtain the mayonnaise as Evaluation Sample 5-3.

[0779] Safflower oil (manufactured by Ajinomoto Co., Ltd.) was heated at 100°C for 30 minutes in a water bath (manufactured by Tokyo Rikaki Co., Ltd.) Mayonnaise obtained by adding 0.2 wt% of the heated safflower oil to the commercially available mayonnaise used in the preparation of the negative control was used as Evaluation Sample 5-4.

[0780] Safflower oil (manufactured by Ajinomoto Co., Ltd.) and furfural (manufactured by Sigma-Aldrich Co., Ltd.) were heated at 100°C for 30 minutes in a water bath (manufactured by Tokyo Rika Kikai Co., Ltd.) and then mixed. The amount of furfural before heating was 100 ppm relative to the safflower oil before heating. 0.1 wt% of the obtained mixture was added to the commercially available mayonnaise used in the preparation of the negative control, and 0.1 wt% of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) was further added to obtain mayonnaise as evaluation sample 5-5.

[0781] Safflower oil (manufactured by Ajinomoto Co., Ltd.) and β-caryophyllene (manufactured by Sigma-Aldrich Co., Ltd.) were heated at 100°C for 30 minutes in a water bath (manufactured by Tokyo Rika Kikai Co., Ltd.) and then mixed. The amount of β-caryophyllene before heating was 100 ppm relative to the safflower oil before heating. 0.1 wt % of the obtained mixture was added to the commercially available mayonnaise used in the preparation of the above negative control, and 0.1 wt % of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) was further added, and the obtained mayonnaise was used as evaluation sample 5-6.

[0782] Safflower oil (manufactured by Ajinomoto Co., Ltd.), furfural and β-caryophyllene (all manufactured by Sigma-Aldrich Co., Ltd.) were heated at 100°C for 30 minutes in a water bath (manufactured by Tokyo Rika Kikai Co., Ltd.) and then mixed. The amounts of furfural and β-caryophyllene before heating were both 100 ppm relative to the safflower oil before heating. 0.1 wt% of the obtained mixture was added to the commercially available mayonnaise used in the preparation of the above negative control, and 0.1 wt% of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) was further added, and the obtained mayonnaise was used as evaluation sample 5-7.

[0783] Furfural (manufactured by Sigma-Aldrich) was added to safflower oil (manufactured by Ajinomoto Co., Ltd.) and dissolved in the concentration shown in Table 5 below (100 ppm relative to safflower oil), and then the safflower oil was heated at 100°C for 30 minutes in a water bath (manufactured by Tokyo Rikaki Co., Ltd.).

[0784] In addition, β-caryophyllene (manufactured by Sigma-Aldrich) was added to safflower oil (manufactured by Ajinomoto Co., Ltd.) and dissolved in the concentration shown in Table 5 below (100 ppm relative to safflower oil), and then the safflower oil was heated at 100°C for 30 minutes in a water bath (manufactured by Tokyo Rikaki Co., Ltd.).

[0785] To the commercially available mayonnaise used in the preparation of the negative control, 0.1% by weight of each heated safflower oil was added (total 0.2% by weight), and the obtained mayonnaise was designated as Evaluation Samples 5 to 8.

[0786] The evaluation of the oral coating feeling was performed in the same manner as in Test Example 1.

[0787] The results are shown in Table 5 below. In addition, the substances in brackets in the sample content in the table refer to the obtained products mixed before heating. For example, the "(safflower oil + furfural + β-caryophyllene) heated product" of evaluation sample 5-1 refers to safflower oil, furfural and β-caryophyllene mixed before heating, and the "safflower oil heated product + furfural heated product + β-caryophyllene heated product" of evaluation sample 5-7 refers to safflower oil, furfural and β-caryophyllene mixed without mixing before heating, and mixed after heating each separately.

[0788] [Table 5]

[0789]

[0790] It can be seen from the results of Table 5 that the oral coating feeling of evaluation samples 5-1 to 5-3 and 5-6 to 5-8 is effectively enhanced by heating the (A) component and / or the (B) component (specifically, the heated product of β-caryophyllene, furfural and safflower oil, the heated product of furfural and safflower oil; the heated product of β-caryophyllene, etc.).

[0791] On the other hand, in the evaluation sample 5-4 to which only the heated product of the component (A2) was added, and the evaluation sample 5-5 to which the components (A1) and (A2) were heated separately and added, the mouth coating feeling was hardly enhanced.

[0792] (Test Example 5-2)

[0793] For the positive control, a product obtained by adding 0.2% by weight of unheated mineral oil (manufactured by Kaneda Corporation) to a common commercially available mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name “PureSelect (registered trademark) mayonnaise”, fat content: 73%) was used.

[0794] For the negative control, a product obtained by adding 0.2% by weight of unheated mineral oil (manufactured by Kaneda Co., Ltd.) to a commercially available mayonnaise having a lower fat content than that of the positive control mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "Pure Select (registered trademark) Kokuuma (registered trademark) 65% Calorie Reduction", fat content: 23%) was used.

[0795] <Evaluation samples 5-9 to 5-20>

[0796] 2-Hexenal, β-caryophyllene and furfural (all manufactured by Sigma-Aldrich) were added to mineral oil (manufactured by KANEDA Co., Ltd.) and dissolved at the concentrations shown in Table 6 below (2-hexenal: 100 ppm relative to mineral oil, β-caryophyllene: 100 ppm relative to mineral oil; furfural: 100 ppm relative to mineral oil), and then the mineral oil was heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikaki Co., Ltd.). 0.1 wt % of heated mineral oil was added to the commercially available mayonnaise used in the preparation of the negative control, and 0.1 wt % of unheated mineral oil was further added to obtain the mayonnaise as evaluation samples 5-9.

[0797] 2-Hexenal and furfural (both manufactured by Sigma-Aldrich) were added to mineral oil (manufactured by KANEDA Co., Ltd.) and dissolved at the concentrations shown in Table 6 below (2-hexenal: 100 ppm relative to mineral oil; furfural: 100 ppm relative to mineral oil), and the mineral oil was heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikaki Co., Ltd.). 0.1% by weight of the heated mineral oil was added to the commercially available mayonnaise used in the preparation of the negative control, and 0.1% by weight of unheated mineral oil was further added to obtain the mayonnaise, which was used as evaluation samples 5-10.

[0798] 2-Hexenal and β-caryophyllene (both manufactured by Sigma-Aldrich) were added to mineral oil (manufactured by KANEDA Co., Ltd.) and dissolved at the concentrations shown in Table 6 below (2-hexenal: 100 ppm relative to mineral oil, β-caryophyllene: 100 ppm relative to mineral oil), and then the mineral oil was heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikaki Co., Ltd.). 0.1% by weight of the heated mineral oil was added to the commercially available mayonnaise used in the preparation of the negative control, and 0.1% by weight of unheated mineral oil was further added to obtain the mayonnaise, which was used as evaluation samples 5-11.

[0799] β-Caryophyllene and furfural (both manufactured by Sigma-Aldrich) were added to mineral oil (manufactured by KANEDA Co., Ltd.) and dissolved at the concentrations shown in Table 6 below (β-Caryophyllene: 100 ppm relative to mineral oil; furfural: 100 ppm relative to mineral oil), and the mineral oil was heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikaki Co., Ltd.). 0.1 wt % of the heated mineral oil was added to the commercially available mayonnaise used in the preparation of the negative control, and 0.1 wt % of unheated mineral oil was further added to obtain the mayonnaise, which was used as evaluation samples 5-12.

[0800] 2-Hexenal (manufactured by Sigma-Aldrich) was added to mineral oil (manufactured by Kaneda Co., Ltd.) and dissolved at the concentration shown in Table 6 below (100 ppm relative to the mineral oil), and the mineral oil was heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikaki Co., Ltd.). 0.1% by weight of the heated mineral oil was added to the commercially available mayonnaise used in the preparation of the negative control, and 0.1% by weight of unheated mineral oil was further added to obtain the mayonnaise, which was used as evaluation samples 5-13.

[0801] Furfural (manufactured by Sigma-Aldrich) was added to mineral oil (manufactured by Kaneda Co., Ltd.) and dissolved at the concentration shown in Table 6 below (100 ppm relative to the mineral oil), and the mineral oil was heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikaki Co., Ltd.). 0.1% by weight of the heated mineral oil was added to the commercially available mayonnaise used in the preparation of the negative control, and 0.1% by weight of unheated mineral oil was further added to obtain the mayonnaise, which was used as evaluation samples 5-14.

[0802] β-Caryophyllene (manufactured by Sigma-Aldrich) was added to mineral oil (manufactured by Kaneda Co., Ltd.) and dissolved at the concentration shown in Table 6 below (100 ppm relative to the mineral oil), and the mineral oil was heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikaki Co., Ltd.). 0.1% by weight of the heated mineral oil was added to the commercially available mayonnaise used in the preparation of the negative control, and 0.1% by weight of unheated mineral oil was further added to obtain the mayonnaise, which was used as evaluation samples 5-15.

[0803] 2-Hexenal, furfural and β-caryophyllene (all manufactured by Sigma-Aldrich) were heated at 100°C for 30 minutes in a water bath (manufactured by Tokyo Rika Instruments Co., Ltd.), and then mineral oil was added for mixing. The amounts of 2-hexenal, furfural and β-caryophyllene before heating were all 100 ppm relative to the mineral oil. 0.1 wt % of the obtained mixture was added to the commercially available mayonnaise used in the preparation of the above negative control, and 0.1 wt % of unheated mineral oil was further added to obtain the mayonnaise as evaluation samples 5-16.

[0804] 2-Hexenal and furfural (both manufactured by Sigma-Aldrich) were added to mineral oil (manufactured by KANEDA Co., Ltd.) and dissolved in the following concentrations (2-hexenal: 100 ppm relative to mineral oil; furfural: 100 ppm relative to mineral oil) as shown in Table 7 below, and then the mineral oil was heated at 100°C for 30 minutes in a water bath (manufactured by Tokyo Rikakki Co., Ltd.), and β-caryophyllene (manufactured by Sigma-Aldrich Co., Ltd.) heated at 100°C for 30 minutes in a water bath (manufactured by Tokyo Rikakki Co., Ltd.) was added thereto and mixed. The amount of β-caryophyllene before heating was 100 ppm relative to the mineral oil before heating. 0.1% by weight of the obtained mixture was added to the commercially available mayonnaise used in the preparation of the above-mentioned negative control, and 0.1% by weight of unheated mineral oil was further added, and the obtained mayonnaise was used as evaluation sample 5-17.

[0805] 2-Hexenal and β-caryophyllene (both manufactured by Sigma-Aldrich) were added to mineral oil (manufactured by KANEDA Co., Ltd.) and dissolved in the concentrations shown in Table 7 below (2-hexenal: 100 ppm relative to mineral oil, β-caryophyllene: 100 ppm relative to mineral oil). The mineral oil was then heated at 100°C for 30 minutes in a water bath (manufactured by Tokyo Rikakki Co., Ltd.), and furfural (manufactured by Sigma-Aldrich Co., Ltd.) heated at 100°C for 30 minutes in a water bath (manufactured by Tokyo Rikakki Co., Ltd.) was added thereto and mixed. The amount of furfural before heating was 100 ppm relative to the mineral oil before heating. 0.1% by weight of the obtained mixture was added to the commercially available mayonnaise used in the preparation of the negative control, and 0.1% by weight of unheated mineral oil was further added to obtain mayonnaise as evaluation samples 5-18.

[0806] β-Caryophyllene and furfural (both manufactured by Sigma-Aldrich) were added to mineral oil (manufactured by KANEDA Co., Ltd.) and dissolved at the concentrations shown in Table 7 below (β-Caryophyllene: 100 ppm relative to mineral oil; furfural: 100 ppm relative to mineral oil), and then the mineral oil was heated at 100°C for 30 minutes in a water bath (manufactured by Tokyo Rikakki Co., Ltd.), and 2-hexenal (manufactured by Sigma-Aldrich Co., Ltd.) heated at 100°C for 30 minutes in a water bath (manufactured by Tokyo Rikakki Co., Ltd.) was added thereto and mixed. The amount of 2-hexenal before heating was 100 ppm relative to the mineral oil before heating. 0.1% by weight of the obtained mixture was added to the commercially available mayonnaise used in the preparation of the negative control, and 0.1% by weight of unheated mineral oil was further added, and the obtained mayonnaise was used as evaluation sample 5-19.

[0807] 2-Hexenal and furfural (both manufactured by Sigma-Aldrich) were added to mineral oil (manufactured by KANEDA Co., Ltd.) and dissolved in the concentrations shown in Table 7 below (2-hexenal: 100 ppm relative to mineral oil; furfural: 100 ppm relative to mineral oil), and the mineral oil was then heated at 100°C for 30 minutes in a water bath (manufactured by Tokyo Rikaki Co., Ltd.).

[0808] 2-Hexenal and β-caryophyllene (both manufactured by Sigma-Aldrich) were added to mineral oil (manufactured by KANEDA Co., Ltd.) and dissolved in the concentrations shown in Table 7 below (2-hexenal: 100 ppm relative to mineral oil, β-caryophyllene: 100 ppm relative to mineral oil), and the mineral oil was then heated at 100°C for 30 minutes in a water bath (manufactured by Tokyo Rikaki Co., Ltd.).

[0809] To the commercially available mayonnaise used in the preparation of the negative control, 0.1 wt % of each heated mineral oil was added (total 0.2 wt %), and the obtained mayonnaise was designated as Evaluation Samples 5 to 20.

[0810] <Sensory Evaluation>

[0811] The evaluation of the oral coating feeling was performed in the same manner as in Test Example 1.

[0812] The results are shown in the following Tables 6 and 7. In addition, the substances in parentheses in the tables refer to the substances obtained by mixing before heating, similarly to Table 5.

[0813] [Table 6]

[0814]

[0815] [Table 7]

[0816]

[0817] It can be seen from the results of Tables 6 and 7 that the oral coating feeling of evaluation samples 5-9 to 5-12 and 5-15 to 5-20 is effectively enhanced by heating the (A) component and / or the (B) component (specifically, the heated product of β-caryophyllene, furfural and 2-hexenal, the heated product of furfural and 2-hexenal; the heated product of β-caryophyllene, etc.).

[0818] On the other hand, in the case of the heated product of Evaluation Sample 5-13 to which only the component (A2) was added and the heated product of Evaluation Sample 5-14 to which only the component (A1) was added, the coating feeling in the mouth was hardly enhanced.

[0819] (Test Example 6)

[0820] <Positive and negative controls>

[0821] For the positive control, a product obtained by adding 0.1% by weight of unheated mineral oil (manufactured by Kaneda Corporation) to a common commercially available mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name “PureSelect (registered trademark) mayonnaise”, fat content: 73%) was used.

[0822] For the negative control, a product obtained by adding 0.1% by weight of unheated mineral oil (manufactured by Kaneda Co., Ltd.) to a commercially available mayonnaise having a lower fat content than that of the positive control mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "Pure Select (registered trademark) Kokuuma (registered trademark) 65% Calorie Reduction", fat content: 23%) was used.

[0823] <Evaluation samples 6-1 to 6-41>

[0824] Each compound (all manufactured by Sigma-Aldrich) shown in Tables 8 to 10 below was added to mineral oil (manufactured by Kaneda Co., Ltd.) and dissolved at each concentration (100 ppm relative to the mineral oil) shown in Tables 8 to 10 below, and then the mineral oil was heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikaki Co., Ltd.). 0.1% by weight of each heated mineral oil was added to the commercially available mayonnaise used in the preparation of the negative control instead of adding unheated mineral oil, and the obtained mayonnaise was used as evaluation samples 6-1 to 6-41.

[0825] <Sensory Evaluation>

[0826] The evaluation of the oral coating feeling was performed in the same manner as in Test Example 1.

[0827] The results are shown in Tables 8 to 10 below.

[0828] [Table 8]

[0829]

[0830] [Table 9]

[0831]

[0832] [Table 10]

[0833]

[0834] From the results of Tables 8 to 10, it is understood that the addition of the heated product of the component (A) and / or the heated product of the component (B) enhanced the coating feeling in the mouth of each evaluation sample.

[0835] (Test Example 7)

[0836] <Positive and negative controls>

[0837] For the positive control, a product obtained by adding 1 wt % of unheated rapeseed oil (manufactured by Ajinomoto Co., Ltd.) to a common commercially available mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "PureSelect (registered trademark) mayonnaise", oil content: 73%) was used.

[0838] For the negative control, 1 wt % of unheated rapeseed oil (manufactured by Ajinomoto Co., Ltd.) was added to a commercially available mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "Pure Select (registered trademark) Kokuuma (registered trademark) 65% Calorie Reduction", fat content: 23%) having a lower fat content than the mayonnaise of the positive control was used.

[0839] <Evaluation Sample>

[0840] A specified amount of β-caryophyllene and furfuryl alcohol (both manufactured by Sigma-Aldrich) was dissolved in rapeseed oil (manufactured by Ajinomoto Co., Ltd.), and then the rapeseed oil was heated at 100°C for 30 minutes using a water bath (manufactured by Tokyo Rikakigi Co., Ltd.). To the commercially available mayonnaise used in the preparation of the above negative control, 1% by weight of each heated rapeseed oil was added instead of adding unheated rapeseed oil, and the obtained mayonnaise was used as an evaluation sample. The amounts of β-caryophyllene and furfuryl alcohol dissolved in rapeseed oil are shown in Table 11 below, and are adjusted to a range of 0.001 to 10000 ppm relative to rapeseed oil.

[0841] <Sensory Evaluation>

[0842] The evaluation of the oral coating feeling was scored as follows: 2 professional evaluators tasted the mayonnaise of the positive control, negative control and evaluation sample, scored "5.0 points" for the positive control and "0.0 points" for the negative control, and evaluated the evaluation sample within the range of 0.0 to 5.0 points with a minimum interval of 0.1 point.

[0843] The results are shown in Table 11 below.

[0844] [Table 11]

[0845]

[0846] The results in Table 11 show that the heated product of component (A) and / or heated product of component (B) (specifically, heated products of β-caryophyllene, furfuryl alcohol and rapeseed oil, etc.) enhanced the coating feeling in the mouth of each evaluation sample.

[0847] In addition, a slightly downward trend can be seen in the scores of evaluation samples containing high concentrations of various heated materials (for example, evaluation samples in which the β-caryophyllene and furfuryl alcohol contained in rapeseed oil when heated are 1000 to 10000 ppm relative to rapeseed oil). It is speculated that this may be due to the abnormal flavor caused by the increased concentration, which makes it difficult to perceive the coating feeling in the mouth.

[0848] (Test Example 8)

[0849] <Positive and negative controls>

[0850] The same substances as those in Test Example 1 were used as positive control and negative control.

[0851] <Evaluation Sample>

[0852] β-Caryophyllene and furfural (both manufactured by Sigma-Aldrich) were dissolved in rapeseed oil (manufactured by Ajinomoto Co., Ltd.) at 100 ppm relative to the rapeseed oil, and the rapeseed oil was heated in an oil bath (manufactured by Yamato Scientific Co., Ltd.) under the conditions (temperature, time) shown in Table 12 below. Mayonnaise obtained by adding 1% by weight of each heated rapeseed oil to the commercially available mayonnaise used in the preparation of the negative control instead of adding unheated rapeseed oil was used as an evaluation sample.

[0853] <Sensory Evaluation>

[0854] The evaluation of the oral coating feeling was performed in the same manner as in Test Example 7.

[0855] The results are shown in Table 12 below.

[0856] [Table 12]

[0857]

[0858] The results in Table 12 indicate that the heating conditions (temperature, time) of the components (A) and (B) may affect the effect of enhancing the mouth coating feeling of the heated products of the components (A) and (B).

[0859] (Test Example 9)

[0860] <Positive and negative controls>

[0861] For the positive control, a model ramen soup stock was used [2.17 g of "Super Cup Soy Sauce" powder soup stock (manufactured by Acecook Co., Ltd.), 1.60 g of chicken fat (manufactured by Maruzen Food Industries, Ltd.), 1.00 g of thick soy sauce (manufactured by Kikkoman Co., Ltd.), 0.40 g of Koji Base (manufactured by Ajinomoto Co., Ltd.), and 0.20 g of marol lard (manufactured by Maruzen Food Industries, Ltd.) were dissolved in hot water to prepare a total amount of 100 g. The present invention relates to a product obtained by adding 0.1% by weight of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) to a fat spread (manufactured by Meiji Co., Ltd., trade name "7 premium light butter (セブンプレミアムかろやかソフト), fat content: 70%), and a product obtained by adding 0.1% by weight of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) to a commercially available fat spread (manufactured by Meiji Co., Ltd., trade name "7 premium light butter (セブンプレミアムかろやかソフト), fat content: 70%).

[0862] For the negative control, a model ramen soup with a lower fat content than the positive control ramen soup was used [2.17 g of "Super Cup Soy Sauce" powder soup (manufactured by Acecook Co., Ltd.), 0.80 g of chicken fat (manufactured by Maruzen Food Industries, Ltd.), 1.00 g of thick soy sauce (manufactured by Kikkoman Co., Ltd.), 0.40 g of Koji Base (manufactured by Ajinomoto Co., Ltd.), and 0.20 g of marol lard (manufactured by Maruzen Food Industries, Ltd.) were dissolved in hot water to prepare a total amount of 100 g. The present invention relates to a product obtained by adding 0.1% by weight of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) to a fat content of 1.0% [fat content: 1.0%], and a product obtained by adding 0.1% by weight of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) to a commercially available spreadable fat having a lower fat content than that of the positive control spreadable fat (manufactured by Meiji Co., Ltd., trade name "Meiji Corn Butter", fat content: 64%).

[0863] For the positive control of mayonnaise, 0.1% by weight of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) was added to a common commercially available mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "Pure Select (registered trademark) Mayonnaise", oil content: 73%).

[0864] For the negative control, a product obtained by adding 1 wt % of unheated safflower oil to a commercially available mayonnaise having a lower fat content than the positive control mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "Pure Select (registered trademark) Kokuuma (registered trademark) 65% Calorie Reduction", fat content: 23%) was used.

[0865] <Evaluation Sample Group 9-1>

[0866] β-Caryophyllene and furfural (both manufactured by Sigma-Aldrich) were dissolved in safflower oil (manufactured by Ajinomoto Co., Ltd.) at 100 ppm relative to safflower oil. Instead of adding unheated safflower oil, 0.1% by weight of safflower oil (unheated) in which β-caryophyllene and furfural were dissolved was added to each food (commercially available mayonnaise, model ramen soup, commercially available spread) used in the preparation of the negative control, and each of the obtained foods (mayonnaise, ramen soup, and spread) was used as evaluation sample group 9-1.

[0867] <Evaluation Sample Group 9-2>

[0868] β-Caryophyllene and furfural (both manufactured by Sigma-Aldrich) were dissolved in safflower oil (manufactured by Ajinomoto Co., Ltd.) at 100 ppm relative to the safflower oil, and the safflower oil was heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikaki Co., Ltd.). Instead of adding unheated safflower oil, 0.1% by weight of heated safflower oil was added to each of the foods (commercially available mayonnaise, model ramen soup, and commercially available spread fat) used in the preparation of the negative control, and the resulting foods (mayonnaise, ramen soup, and spread fat) were used as evaluation sample group 9-2.

[0869] <Sensory Evaluation>

[0870] The evaluation of the oral coating feeling was scored as follows: 3 professional evaluators tasted the positive control, negative control and each food of the evaluation sample (mayonnaise, ramen soup and spread fat), scored the positive control as "5.0 points" and the negative control as "0.0 points", and evaluated the evaluation sample within the range of 0.0 to 5.0 points with a minimum interval of 0.1 points.

[0871] The results are shown in Table 13 below.

[0872] [Table 13]

[0873]

[0874] From the results in Table 13, it can be seen that the heated product of component (A) and / or the heated product of component (B) (specifically, the heated product of β-caryophyllene, furfural and safflower oil) enhances the mouth coating feeling in any of mayonnaise, ramen soup and spread fat.

[0875] (Test Example 10)

[0876] <Positive and negative controls>

[0877] The same substances as those in Test Example 7 were used as positive controls and negative controls.

[0878] <Evaluation Sample 10-1>

[0879] β-Caryophyllene and furfural (both manufactured by Sigma-Aldrich) were dissolved in rapeseed oil (manufactured by Ajinomoto Co., Ltd.) at 100 ppm, respectively, relative to the rapeseed oil. Instead of adding unheated rapeseed oil, 0.1 wt % of the rapeseed oil (unheated) in which β-caryophyllene and furfural were dissolved was added to the commercially available mayonnaise used in the preparation of the negative control, and the obtained mayonnaise was used as evaluation sample 10-1.

[0880] <Evaluation Sample 10-2>

[0881] β-Caryophyllene and furfural (both manufactured by Sigma-Aldrich) were dissolved in rapeseed oil (manufactured by Ajinomoto Co., Ltd.) at 100 ppm each relative to the rapeseed oil, and the rapeseed oil was heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikakigi Co., Ltd.). 0.1% by weight of heated rapeseed oil was added to the commercially available mayonnaise used in the preparation of the negative control instead of adding unheated rapeseed oil, and the obtained mayonnaise was used as evaluation sample 10-2.

[0882] <Sensory Evaluation>

[0883] The evaluation of the oral coating feeling was scored as follows: the two-point discrimination evaluation under the dark evaluation condition ( Figure 1 ) and rating reviews ( Figure 2 ), and the evaluation was repeated 3 times by 3 professional evaluators (9 times in total). In addition, the scoring evaluation was performed as follows: the mayonnaise of the positive control, the negative control, and the evaluation samples 10-1 and 10-2 was tasted, the positive control was scored as "5.0 points", the negative control was scored as "0.0 points", and the samples 10-1 and 10-2 were evaluated within the range of 0.0 to 5.0 points with a minimum interval of 0.1 points.

[0884] The results are shown in Figure 1 and Figure 2 middle.

[0885] Depend on Figure 1 and Figure 2 The results show that in the sensory evaluation under dark conditions, the mouth coating feeling of mayonnaise is enhanced by the heated product of component (A) and / or the heated product of component (B) (specifically, the heated product of β-caryophyllene, furfural and rapeseed oil).

[0886] (Test Example 11)

[0887] <Positive and negative controls>

[0888] The same substances as those in Test Example 7 were used as positive controls and negative controls.

[0889] <Evaluation samples 11-1 to 11-4>

[0890] (a) β-Caryophyllene (manufactured by Sigma-Aldrich) was dissolved in rapeseed oil (manufactured by Ajinomoto Co., Ltd.) so as to be 10 ppm based on the rapeseed oil, and the rapeseed oil was then heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikaki Co., Ltd.).

[0891] (b) Furfuryl alcohol (manufactured by Sigma-Aldrich) was dissolved in rapeseed oil at a concentration of 100 ppm based on the rapeseed oil. The rapeseed oil (manufactured by Ajinomoto Co., Ltd.) was then heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikaki Co., Ltd.).

[0892] (C) β-Caryophyllene and furfuryl alcohol (both manufactured by Sigma-Aldrich) were dissolved in rapeseed oil (manufactured by Ajinomoto Co., Ltd.) at 10 ppm and 100 ppm, respectively, based on the rapeseed oil, and the rapeseed oil was then heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikaki Co., Ltd.).

[0893] To the commercially available mayonnaise used in the preparation of the negative control, each of the heated rapeseed oils prepared in the above (a) to (c) and a mixture of the heated rapeseed oil prepared in the above (a) and the heated rapeseed oil prepared in the above (b) were added instead of adding unheated rapeseed oil, and the obtained mayonnaises were used as evaluation samples 11-1 to 11-4.

[0894] <Sensory Evaluation>

[0895] The evaluation of the oral coating feeling was performed in the same manner as in Test Example 7.

[0896] The results are shown in Table 14 below.

[0897] [Table 14]

[0898]

[0899] From the results of Table 14, it is understood that the mouth-coating feeling was enhanced in both the evaluation samples prepared using the heated product of the component (A) and the evaluation samples prepared using the heated product of the component (B).

[0900] In addition, the mouth coating feeling was enhanced in both the evaluation samples prepared using the heated product obtained by heating the (A) component and the (B) component together and the evaluation samples prepared using the heated product of the (A) component and the heated product of the (B) component obtained separately.

[0901] (Test Example 12)

[0902] <Positive and negative controls>

[0903] The same substances as those in Test Example 1 were used for the positive control and the negative control.

[0904] <Evaluation Sample Groups 12-1 and 12-2>

[0905] Rapeseed oil (manufactured by Ajinomoto Co., Ltd.), soybean oil (manufactured by Ajinomoto Co., Ltd.), corn oil (manufactured by Ajinomoto Co., Ltd.), olive oil (manufactured by Ajinomoto Co., Ltd.), safflower oil (manufactured by Ajinomoto Co., Ltd.), flaxseed oil (manufactured by Asahi Co., Ltd.), wild sesame oil (manufactured by Asahi Co., Ltd.), hydrogenated palm kernel oil (manufactured by Joil Mills Co., Ltd.) and medium-chain fatty acid oil (manufactured by Nissin Oillio Group Co., Ltd.) were directly heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikakigi Co., Ltd.). Instead of adding unheated rapeseed oil, 1% by weight of each heated solvent was added to the commercially available mayonnaise used in the preparation of the negative control, and the obtained mayonnaise was respectively used as evaluation sample group 12-1.

[0906] (III) β-Caryophyllene and furfural (both manufactured by Sigma-Aldrich) were dissolved in rapeseed oil (manufactured by Ajinomoto Co., Ltd.), soybean oil (manufactured by Ajinomoto Co., Ltd.), corn oil (manufactured by Ajinomoto Co., Ltd.), olive oil (manufactured by Ajinomoto Co., Ltd.), safflower oil (manufactured by Ajinomoto Co., Ltd.), linseed oil (manufactured by Asahi Co., Ltd.), wild sesame oil (manufactured by Asahi Co., Ltd.), hydrogenated palm kernel oil (manufactured by Joil Mills Co., Ltd.), and medium-chain fatty acid oil (manufactured by Nissin Oillio Group Co., Ltd.) so that the concentration of each solvent was 100 ppm with respect to the solvent, and then heated at 100° C. for 30 minutes in a water bath (manufactured by Tokyo Rikakigi Co., Ltd.). 1% by weight of each heated solvent was added to the commercially available mayonnaise used in the preparation of the negative control instead of adding unheated rapeseed oil, and the obtained mayonnaise was used as evaluation sample group 12-2.

[0907] <Sensory Evaluation>

[0908] The evaluation of the oral coating feeling was performed in the same manner as in Test Example 7.

[0909] The results are shown in Table 15 below.

[0910] [Table 15]

[0911]

[0912] From the results in Table 15, it can be seen that when rapeseed oil, soybean oil, corn oil, olive oil, safflower oil, linseed oil, wild sesame oil, hydrogenated palm kernel oil and medium-chain fatty acid oil were used as oils, the oral coating feeling of the evaluated samples was enhanced.

[0913] (Test Example 13)

[0914] <Positive and negative controls>

[0915] For the positive control, 0.1% by weight of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) was added to a common commercially available mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "PureSelect (registered trademark) mayonnaise", oil content: 73%).

[0916] For the negative control, a product obtained by adding 0.1% by weight of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) to a commercially available mayonnaise having a lower fat content than that of the positive control mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "Pure Select (registered trademark) Kokuuma (registered trademark) 65% Calorie Reduction", fat content: 23%) was used.

[0917] <Evaluation Sample>

[0918] A specified amount of β-caryophyllene and furfural (both manufactured by Sigma-Aldrich) was dissolved in safflower oil (manufactured by Ajinomoto Co., Ltd.), and then the safflower oil was heated at 100°C for 30 minutes in a water bath (manufactured by Tokyo Rikakigi Co., Ltd.). To the commercially available mayonnaise used in the preparation of the above negative control, 0.1% by weight of each heated safflower oil was added instead of adding unheated rapeseed oil, and the obtained mayonnaise was used as an evaluation sample. The amount of safflower oil dissolved in β-caryophyllene and furfural was as shown in Tables 16 to 19 below, and was adjusted to a range of 0.001 to 300,000 ppm relative to safflower oil.

[0919] <Sensory Evaluation>

[0920] The intensity of the oral coating feeling was evaluated as follows: 2 professional evaluators tasted the mayonnaise of the positive control, negative control and evaluation sample, scored "5.0 points" for the positive control and "0.0 points" for the negative control, and evaluated the evaluation sample within the range of 0.0 to 5.0 points with a minimum interval of 0.1 point.

[0921] The results are shown in Tables 16 to 19 below.

[0922] [Table 16]

[0923]

[0924] [Table 17]

[0925]

[0926] [Table 18]

[0927]

[0928] [Table 19]

[0929]

[0930] From the results in Tables 16 to 19, it can be seen that the heated product of component (A) and / or heated product of component (B) (specifically, heated products of β-caryophyllene and / or furfural, and safflower oil, etc.) enhanced the mouth coating feeling of each evaluation sample.

[0931] (Test Example 14)

[0932] <Synthesis example>

[0933] (Synthesis of syringabicycloalkanediol and syringabicycloalkanediol-3-monoacetate)

[0934] β-Caryophyllene oxide (11 mg) was dissolved in 80% acetic acid aqueous solution (1 mL) and allowed to stand at room temperature for 11 days. Excess solvent was removed by distillation under reduced pressure, and then the residue was purified by reverse phase high performance liquid chromatography (HPLC) (water-ethanol) to obtain the following compound 1 (syringabicycloalkanediol) (1.2 mg) and compound 2 (syringabicycloalkanediol-3-monoacetate) (0.7 mg).

[0935] Compound 1 (Clove tricycloalkanediol):

[0936] [Chemistry 68]

[0937]

[0938] Compound 2 (syringabicycloalkanediol-3-monoacetate):

[0939] [Chemistry 69]

[0940]

[0941] (Synthesis of Clove Tricycloalkanediol Diacetate)

[0942] Syringtricycloalkanediol (5 mg) was dissolved in acetic acid (0.2 mL) and stirred at 80° C. for 20 hours. The reaction solution was concentrated to dryness under reduced pressure, and the obtained residue was purified by reverse phase HPLC (water-ethanol) to obtain the following compound 3 (syringtricycloalkanediol diacetate) (1.2 mg).

[0943] Compound 3 (Clove tricycloalkanediol diacetate):

[0944] [Chemistry 70]

[0945]

[0946] (Synthesis of 3-monoisovalerate of syringabicycloalkanediol)

[0947] Syringa tricycloalkanediol (5.7 mg) was dissolved in isovaleric acid (0.1 mL) and then stirred at 80° C. for 20 hours. A saturated aqueous sodium bicarbonate solution was added to the reaction solution, and then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated to dryness under reduced pressure. The obtained residue was purified by reverse phase HPLC (water-ethanol) to obtain the following compound 4 (syringa tricycloalkanediol-3-monoisovalerate) (2 mg).

[0948] Compound 4 (Clove tricycloalkanediol-3-monoisovalerate):

[0949] [Chemistry 71]

[0950]

[0951] (Synthesis of 2-methoxysyringanol)

[0952] Tetracyanoethylene (13 mg) was added to a methanol solution (2 mL) of β-caryophyllene oxide (227 mg), and the mixture was stirred at room temperature for 20 hours. The reaction solution was concentrated to dryness under reduced pressure, and the residue obtained was purified by reverse phase HPLC (water-acetonitrile) to obtain the following compound 5 (2-methoxysyringanol) (30 mg).

[0953] Compound 5 (2-methoxysyringanol):

[0954] [Chemistry 72]

[0955]

[0956] Synthesis of (1R,3Z,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol and (1R,4R,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undecane-4,5-diol)

[0957] β-Caryophyllene oxide (32 mg) was heated to reflux in pH 4 acetic acid-sodium acetate buffer / acetonitrile (1:1) (1 mL) for 3 hours. Water and n-hexane were added to the reaction solution for partitioning. The fraction that migrated to the organic layer was purified by reverse phase HPLC (water-acetonitrile) to obtain the following compound 6 (2.5 mg) and compound 7 (0.2 mg).

[0958] Compound 6 ((1R,3Z,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol):

[0959] [Chemistry 73]

[0960]

[0961] Compound 7 ((1R,4R,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undecane-4,5-diol):

[0962] [Chemistry 74]

[0963]

[0964] (Synthesis of Caryophyllene Diol II)

[0965] To an acetone solution (2 mL) of β-caryophyllene oxide (235 mg) was added tetracyanoethylene (28 mg) and lithium bromide (465 mg), and the mixture was stirred at room temperature for 1 hour. A 10% aqueous sodium thiosulfate solution was added to the reaction solution, and then the mixture was extracted with hexane. The organic layer was dried over anhydrous sodium sulfate and then concentrated to dryness under reduced pressure. The residue was purified by reverse phase HPLC (water-acetonitrile) to obtain the following compound 8 (caryophyllene diol II) (105 mg).

[0966] Compound 8 (caryophyllene glycol II):

[0967] [Chemistry 75]

[0968]

[0969] (Synthesis of (1S,5R,9R)-10,10-dimethyl-2,6-dimethoxy-bicyclo[7.2.0]undec-5-ol acetate and (1R,3EZ,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol-5-acetate)

[0970] Anhydrous acetic acid (0.08 mL) was added to a pyridine solution (0.1 mL) of caryophyllene diol (12 mg), and the mixture was allowed to stand at room temperature for 20 hours. The residue obtained by concentrating to dryness under reduced pressure was purified by reverse phase HPLC (water-acetonitrile) to obtain the following compounds 9 (2.1 mg) and 10 (0.7 mg), respectively.

[0971] Compound 9 ((1S,5R,9R)-10,10-dimethyl-2,6-bismethylene-bicyclo[7.2.0]undecane-5-ol acetate):

[0972] [Chemistry 76]

[0973]

[0974] Compound 10 ((1R,3EZ,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol-5-acetate):

[0975] [Chemistry 77]

[0976]

[0977] <Positive and negative controls>

[0978] For the positive control, 0.001 wt% of ethanol (manufactured by Nippon Alcohol Industry Co., Ltd.) was added to a common commercially available mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name “PureSelect (registered trademark) mayonnaise”, fat content: 73%).

[0979] For the negative control, 0.001% by weight of ethanol (manufactured by Nippon Alcohol Industry Co., Ltd.) was added to a commercially available mayonnaise having a lower fat content than the mayonnaise of the positive control (manufactured by Ajinomoto Co., Ltd., trade name "Pure Select (registered trademark) Kokuuma (registered trademark) 65% Calorie Reduction", fat content: 23%).

[0980] <Evaluation Sample>

[0981] Predetermined amounts of β-caryophyllene, β-caryophyllene oxide, syringabicycloalkanediol, (1R,3Z,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol, (1R,4R,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undecane-4,5-diol, syringabicycloalkanediol-3-monoacetate, syringabicycloalkanediol diacetate, syringabicycloalkanediol-3-monoisovalerate, α-pinene, α-pinene oxide, limonene, limonene oxide, α-terpinenol (syringabicycloalkanediol, (1R,3Z,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undecane-4,5-diol) were prepared. -8-methylenebicyclo[7.2.0]undec-3-en-5-ol, (1R,4R,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undecane-4,5-diol, syringabicyclo[7.2.0]undecane-4,5-diol, syringabicyclo[3-monoacetate, syringabicyclo[3-monoacetate and syringabicyclo[3-monoisovalerate] (the products obtained in the above-mentioned synthesis example were used, and except for these, products manufactured by Sigma-Aldrich were used) were dissolved in ethanol (manufactured by Nippon Alcohol Industry Co., Ltd.), and 0.001% by weight of the ethanol was added relative to the commercially available mayonnaise used in the preparation of the above-mentioned negative control, and the obtained mayonnaise was used as an evaluation sample. The amounts of ethanol dissolved in β-caryophyllene, β-caryophyllene oxide, syringabicycloalkanediol, (1R,3Z,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol, (1R,4R,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undecane-4,5-diol, syringabicycloalkanediol-3-monoacetate, syringabicycloalkanediol diacetate, syringabicycloalkanediol-3-monoisovalerate, α-pinene, α-pinene oxide, limonene, limonene oxide, and α-terpinenol were adjusted to be in the range of 0.01 to 1 ppm relative to mayonnaise as shown in Table 20 below.

[0982] <Sensory Evaluation>

[0983] The intensity of the oral coating feeling was evaluated as follows: 3 professional evaluators tasted the mayonnaise of the positive control, negative control and evaluation sample, scored "5.0 points" for the positive control and "0.0 points" for the negative control, and evaluated the evaluation sample within the range of 0.0 to 5.0 points with a minimum interval of 0.1 point.

[0984] The results are shown in Table 20 below.

[0985] [Table 20]

[0986]

[0987] From the results in Table 20, it can be seen that the oral coating feeling of each evaluation sample was enhanced by adding β-caryophyllene oxide, syringabicyclo[7.2.0]undec-3-en-5-ol, (1R,4R,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undecane-4,5-diol, syringabicyclo[7.2.0]undecane-3-monoacetate, syringabicyclo[7.2.0]undecane-4,5-diol, syringabicyclo[3-monoacetate, syringabicyclo[3-monoisovalerate, α-pinene oxide, limonene oxide, and α-terpinenol.

[0988] (Test Example 15)

[0989] <Comparison of the production of instant noodles>

[0990] 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) are dissolved in 34 parts by weight of water, and 35.8 parts by weight of the obtained aqueous solution (kneading water) are added to 100 parts by weight of wheat flour (sub-high gluten flour) and kneaded for 2 minutes. The obtained dough is made into thin sheets (thickness: 1.5 ± 0.2 mm) using an electric noodle press manufactured by MARCATO (MArcato S.pA), the two ends are cut off, and then cut into 1 mm wide and 30 cm long. Knead the obtained noodles, and then steam them for 2 minutes at 100°C in a continuous steamer (manufactured by Fuji Seisakusho). 30 g of 5% salt water heated to about 50°C is added to 100 g of steamed noodles for seasoning. The seasoned noodles were fried in oil (palm oil) at 145°C for 80 seconds in a continuous fryer and then cooled to room temperature to obtain instant noodles (hereinafter referred to as "control instant noodles"). The instant noodles were stored under refrigeration at 5°C until use.

[0991] <Preparation of Heated Material A>

[0992] β-Caryophyllene and furfural (both manufactured by Sigma-Aldrich) were dissolved in a medium-chain fatty acid oil (manufactured by Fuji Oil Co., Ltd.) at 1000 ppm each, and the medium-chain fatty acid oil was then heated at 95°C for 30 minutes using a kneader (TKCOMBI MIX, manufactured by PRIMIX Co., Ltd.) (hereinafter, the obtained heated product is referred to as "heated product A").

[0993] <Production of Instant Noodles of Evaluation Sample 15-1>

[0994] When preparing kneading water by dissolving salt, potassium carbonate and sodium carbonate in water, 0.003 weight parts of heated material A was further added to make it uniformly dispersed, and 35.803 weight parts of the obtained dispersion were added to 100 weight parts of wheat flour. Except for this, instant noodles were prepared by the same steps as the control (hereinafter referred to as "instant noodles of evaluation sample 15-1").

[0995] <Production of Instant Noodles of Evaluation Sample 15-2>

[0996] When preparing kneading water by dissolving salt, potassium carbonate and sodium carbonate in water, 0.007 weight part of heated material A was further added to make it uniformly dispersed, and 35.807 weight parts of the obtained dispersion were added to 100 weight parts of wheat flour. Except for this, instant noodles were prepared by the same steps as the control (hereinafter referred to as "instant noodles of evaluation sample 15-2").

[0997] <Production of Instant Noodles of Evaluation Sample 15-3>

[0998] When preparing kneading water by dissolving salt, potassium carbonate and sodium carbonate in water, 0.02 weight parts of heated material A was further added to make it uniformly dispersed, and 35.82 weight parts of the obtained dispersion were added to 100 weight parts of wheat flour. Except for this, instant noodles were prepared by the same steps as the control (hereinafter referred to as "instant noodles of evaluation sample 15-3").

[0999] <Sensory Evaluation>

[1000] 100 g of evaluation samples 15-1 to 15-3 and control instant noodles were boiled in 300 g of hot water at 100°C for 3 minutes, respectively, and sensory evaluation was performed. The sensory evaluation was performed by three trained professional evaluators who jointly scored the evaluation samples 15-1 to 15-3 based on the following criteria, with the minimum interval unit of 0.5 points, based on the "animal fat-like richness" (the thickness and persistence that appears "from the middle to the back" when the animal fat is held in the mouth (specifically, 3 seconds after the animal fat is held in the mouth)), "animal fat-like sweetness" (the sweetness that appears "from the front to the middle" when the animal fat is held in the mouth (specifically, until 2 seconds after the animal fat is held in the mouth)) and "mouth coating feeling" (the feeling of oil sticking to the mouth when sucking noodles). In addition, as a comprehensive evaluation, when the greasiness is greatly improved compared with the control instant noodles, it is judged as "◎"; when it is given a greasiness compared with the control instant noodles, it is judged as "0"; when there is no greasiness and it is the same as the control instant noodles, it is judged as "×".

[1001] (Evaluation criteria for animal fat-like richness, animal fat-like sweetness, and mouth-coating feeling)

[1002] +2 points: better than the control;

[1003] +1 point: slightly better than the control;

[1004] 0 points: equivalent to the control;

[1005] -1 point: slightly weaker than the control;

[1006] -2 points: weaker than the control.

[1007] The evaluation results are shown in Table 21 below.

[1008] [Table 21]

[1009]

[1010] As shown in Table 21, the oral coating feeling of each evaluation sample was enhanced by heating the component (A) and / or the component (B) (specifically, heating the β-caryophyllene, furfural and medium-chain fatty acid oil). In addition, the richness and sweetness like animal fats were also enhanced.

[1011] (Test Example 16)

[1012] <Method for preparing creaming powder>

[1013] (Model non-dairy creamer 1)

[1014] Model non-dairy creamer 1 is prepared as follows: First, sodium hydroxide, acid casein, dipotassium hydrogen phosphate and maltose in the raw materials shown in Table 22 below are mixed in warm water at 60°C in the proportions shown in Table 22. Next, the remaining raw materials (hydrogenated palm kernel oil, monoglycerol fatty acid ester and sorbitan fatty acid ester) are added to the resulting mixed solution in the proportions shown in Table 22 and mixed. Using a homogenizer (product name: "LABOLUTION", manufactured by PRIMIX Co., Ltd.), the resulting mixture is stirred at 8000 rpm for 15 minutes to pre-emulsify it. Then, a homogenizer (product name: "APV-2000", manufactured by APV) is used at 400 kg / cm 2 The obtained emulsion was homogenized and spray-dried using a spray dryer (product name: "Mini Spray Dryer B-290", manufactured by BUCHI) at an intake temperature of 180°C and an exhaust temperature of 90°C to obtain non-dairy creamer (model non-dairy creamer 1).

[1015] [Table 22]

[1016]

[1017] (Model non-dairy creamer 2)

[1018] A non-dairy creamer (model non-dairy creamer 2) was obtained by the same procedure as that of the model non-dairy creamer 1, except that the emulsion obtained after the preliminary emulsification was heated at 95°C for 30 minutes using a water bath (product name: "EC-Water Bath", manufactured by AS ONE Co., Ltd.) before homogenization.

[1019] (Model non-dairy creamer 3)

[1020] A non-dairy creamer (model non-dairy creamer 3) was obtained by the same procedure as that of model non-dairy creamer 1, except that the raw materials shown in the following Table 23 were used instead of the raw materials shown in Table 22.

[1021] Specifically, first, sodium hydroxide, acid casein, dipotassium hydrogen phosphate and maltose in the raw materials shown in Table 23 below are mixed in warm water at 60°C in the proportions shown in Table 23. Then, the remaining raw materials (hydrogenated palm kernel oil, monoglycerol fatty acid esters and sorbitan fatty acid esters, caryophyllene, furfural) are added to the obtained mixed solution in the proportions shown in Table 23 and mixed. The obtained mixture is stirred at 8000 rpm for 15 minutes using a homogenizer (product name: "LABOLUTION", manufactured by PRIMIX Co., Ltd.) to pre-emulsify it. Then, a homogenizer (product name: "APV-2000", manufactured by APV) is used at 400 kg / cm 2 The obtained emulsion was homogenized and spray-dried using a spray dryer (product name: "Mini Spray Dryer B-290", manufactured by BUCHI) at an intake temperature of 180°C and an exhaust temperature of 90°C to obtain non-dairy creamer (model non-dairy creamer 3).

[1022] [Table 23]

[1023]

[1024] (Model non-dairy creamer 4)

[1025] The emulsion obtained after the preliminary emulsification was heated at 95°C for 30 minutes using a water bath (product name: "EC-Water Bath", manufactured by AS ONE Co., Ltd.) before homogenization, and the same operating procedures as those of the model non-dairy creamer 3 were followed to obtain a non-dairy creamer (model non-dairy creamer 4).

[1026] Commercially available products were used as the raw materials used in the preparation of the model non-dairy creamers 1 to 4. The manufacturers of the raw materials are shown in Table 24 below.

[1027] [Table 24]

[1028] Raw material name Manufacturing Company Maltose Showa Sangyo Co., Ltd. Acid Casein Westland Milk products Hydrogenated Palm Kernel Oil J-Oil Mills Co., Ltd. Sorbitan fatty acid esters Kao Co., Ltd. Monoglyceride of fatty acids Riken Vitamin Co., Ltd. Dipotassium hydrogen phosphate Taihei Chemical Industry Co., Ltd.

[1029] <Preparation of Evaluation Samples (Coffee Au Lait in Test Areas 1 to 8)>

[1030] In a cup, add the amounts of commercially available instant coffee powder (manufactured by Ajinomoto AGF Co., Ltd.), any one of the model non-dairy creamers 1 to 4, and sugar (manufactured by Mitsui Sugar Co., Ltd.) shown in Table 25 below, pour in 180 mL of boiling water, and stir for a few seconds until the powder is completely dissolved to prepare the au gratin coffee of test areas 1 to 8 respectively.

[1031] [Table 25]

[1032]

[1033] <Sensory Evaluation>

[1034] Regarding the intensity of the mouth coating feeling (fat-like thickness that spreads throughout the mouth), milk feeling (milk-like aroma and sweetness), and coffee roasting feeling (similar to the fragrant aroma and bitterness of coffee) of the coffee au lait in test areas 1 to 8, 6 trained professional evaluators scored according to 5 levels (1 to 5 points: 1 point is the weakest and 5 points is the strongest) with a minimum interval unit of 1 point, thereby evaluating. Specifically, taking test area 1 as the standard, all of the mouth coating feeling, milk feeling, and coffee roasting feeling are defined as 1 point. In addition, the mouth coating feeling and milk feeling when the amount of model non-dairy creamer in test area 1 is increased by 1.5 times (test area 2) are defined as 5 points respectively. Further, the roasting feeling of coffee when the amount of instant coffee powder in test area 1 is increased by 1.1 times (test area 7) is defined as 3 points. The scores given by each professional evaluator are averaged, and the average score obtained is used as the evaluation of each coffee au lait. The evaluation results are shown in Table 26 below.

[1035] [Table 26]

[1036]

[1037] From the results in Table 26, it can be seen that the mouth coating feeling, milk feeling and coffee roasting feeling of test area 5 using heated material of component (A) and / or heated material of component (B) (specifically, heated materials of β-caryophyllene, furfural and hydrogenated palm kernel oil, etc.) were enhanced.

[1038] (Test Example 17)

[1039] <Method for preparing non-dairy creamer>

[1040] (Model non-dairy creamer 5)

[1041] Model non-dairy creamer 5 was prepared as follows: First, sodium hydroxide, acid casein, dipotassium hydrogen phosphate and maltose among the raw materials shown in Table 23 were mixed in warm water at 60°C in the proportions shown in Table 17. Then, the remaining raw materials (hydrogenated palm kernel oil, monoglycerol fatty acid ester and sorbitan fatty acid ester, caryophyllene, furfural) were added to the obtained mixed solution in the proportions shown in Table 23 and mixed. The obtained mixture was stirred at 8000 rpm for 15 minutes using a homomixer (product name: "LABOLUTION", manufactured by PRIMIX Co., Ltd.) to pre-emulsify it. Then, the obtained emulsion was sterilized by heating at 95°C for 15 seconds using an ultra-high temperature (UHT) sterilizer for experiments (product name: "ECONOLAB-T MK-2", manufactured by Powerpoint International), and then homogenized at 400 kg / cm using a homogenizer (product name: "APV-2000", manufactured by APV). 2 The homogenized emulsion was spray-dried using a spray dryer (product name: "Mini Spray Dryer B-290", manufactured by BUCHI) at an intake temperature of 180°C and an exhaust temperature of 90°C to obtain non-dairy creamer (model non-dairy creamer 5).

[1042] The raw materials used in the preparation of the model non-dairy creamer 5 are the same as those used in the preparation of the model non-dairy creamers 1 to 4.

[1043] <Preparation of Evaluation Sample (Coffee Au Lait in Test Area 9)>

[1044] Into a cup were added the amounts of commercially available instant coffee powder (manufactured by Ajinomoto AGF Co., Ltd.), model non-dairy creamer 7, and sugar (manufactured by Mitsui Sugar Co., Ltd.) shown in Table 27 below, 180 mL of boiling water was poured, and the mixture was stirred for a few seconds until the powder was completely dissolved to prepare the au gratin coffee of Test Area 9.

[1045] [Table 27]

[1046]

[1047] <Sensory Evaluation>

[1048] The mouth coating feeling, milk feeling, and roasted coffee feeling of the café au lait of Test Zone 9 were evaluated in the same manner as in Test Example 16. The evaluation results are shown in Table 28 below.

[1049] [Table 28]

[1050]

[1051] From the results in Table 28, it can be seen that the heated product obtained by heating β-caryophyllene, furfural, hydrogenated palm kernel oil, etc. at 95° C. for 15 seconds has a sufficiently enhanced mouth-coating feeling and a roasted coffee feeling.

[1052] (Test Example 18)

[1053] <Method for preparing non-dairy creamer>

[1054] (Model non-dairy creamer 6)

[1055] Model non-dairy creamer 6 is prepared as follows: First, sodium hydroxide, acid casein, dipotassium hydrogen phosphate and maltose in the raw materials shown in Table 23 are mixed in warm water at 60°C in the proportions shown in Table 17. Then, the remaining raw materials (hydrogenated palm kernel oil, monoglycerol fatty acid esters and sorbitan fatty acid esters, caryophyllene, furfural) are added to the obtained mixed solution in the proportions shown in Table 23 and mixed. The obtained mixture is stirred at 8000 rpm for 15 minutes using a homogenizer (product name: "LABOLUTION", manufactured by PRIMIX Co., Ltd.) to pre-emulsify it. Then, the obtained emulsion is heated at 95°C for 10 minutes using a water bath (product name: "EC-Water Bath", manufactured by AS ONE Co., Ltd.), and then a homogenizer (product name: "APV-2000", manufactured by APV) is used at 400 kg / cm 2 The homogenized emulsion was spray-dried using a spray dryer (product name: "Mini Spray Dryer B-290", manufactured by BUCHI) at an intake temperature of 180°C and an exhaust temperature of 90°C to obtain non-dairy creamer (model non-dairy creamer 6).

[1056] (Model non-dairy creamer 7)

[1057] A non-dairy creamer (model non-dairy creamer 7) was obtained by the same procedure as that of model non-dairy creamer 6 except that the emulsion obtained after the preliminary emulsification was heated at 95°C for 60 minutes in a water bath before homogenization.

[1058] (Model non-dairy creamer 8)

[1059] A non-dairy creamer (model non-dairy creamer 8) was obtained by the same procedure as that of model non-dairy creamer 6 except that the emulsion obtained after the preliminary emulsification was heated at 80°C for 10 minutes in a water bath before homogenization.

[1060] (Model non-dairy creamer 9)

[1061] A non-dairy creamer (model non-dairy creamer 9) was obtained by the same procedure as that of model non-dairy creamer 6 except that the emulsion obtained after the preliminary emulsification was heated at 80°C for 30 minutes in a water bath before homogenization.

[1062] (Model non-dairy creamer 10)

[1063] A non-dairy creamer (model non-dairy creamer 10) was obtained by the same procedure as that of the model non-dairy creamer 6 except that the emulsion obtained after the preliminary emulsification was heated at 80°C for 60 minutes in a water bath before homogenization.

[1064] (Model non-dairy creamer 11)

[1065] The same procedure as that of the model non-dairy creamer 6 was followed, except that the emulsion obtained after the preliminary emulsification was heated at 70° C. for 10 minutes in a water bath before homogenization, to obtain a non-dairy creamer (model non-dairy creamer 11).

[1066] (Model non-dairy creamer 12)

[1067] A non-dairy creamer (model non-dairy creamer 12) was obtained by the same procedure as that of the model non-dairy creamer 6 except that the emulsion obtained after the preliminary emulsification was heated at 70°C for 30 minutes in a water bath before homogenization.

[1068] (Model non-dairy creamer 13)

[1069] The same procedure as that of the model non-dairy creamer 6 was followed except that the emulsion obtained after the preliminary emulsification was heated at 70° C. for 60 minutes in a water bath before homogenization to obtain a non-dairy creamer (model non-dairy creamer 13).

[1070] The heating conditions (heating temperature, heating time) of the emulsions obtained after pre-emulsification in the preparation of the model non-dairy creamers 6 to 13 are shown in Table 29 below.

[1071] [Table 29]

[1072]

[1073] The raw materials used in the preparation of the model non-dairy creamers 6 to 13 were the same as those used in the preparation of the model non-dairy creamers 1 to 4.

[1074] <Preparation of Evaluation Samples (Coffee Au Lait from Test Areas 10 to 17)>

[1075] In a cup, add the amounts of commercially available instant coffee powder (manufactured by Ajinomoto AGF Co., Ltd.), any one of model non-dairy creamer 6 to 13, and sugar (manufactured by Mitsui Sugar Co., Ltd.) shown in Table 30 below, pour in 180 mL of boiling water, stir for a few seconds until the powder is completely dissolved, and prepare the au gratin for test areas 10 to 17 respectively.

[1076] [Table 30]

[1077]

[1078] <Sensory Evaluation>

[1079] The mouth-coating feeling, milky feeling, and roasted coffee feeling of the café au lait of Test Sections 10 to 17 were evaluated in the same manner as in Test Example 16. The evaluation results are shown in Table 31 below.

[1080] [Table 31]

[1081]

[1082] From the results in Table 31, it can be seen that the heated product obtained by heating β-caryophyllene, furfural, hydrogenated palm kernel oil, etc. at 70° C. or higher has a sufficiently enhanced mouth-coating feeling and milky feeling.

[1083] (Test Example 19)

[1084] <Method for preparing non-dairy creamer>

[1085] (Model non-dairy creamer 14-17)

[1086] Model non-dairy creamers 14 to 17 were prepared as follows: First, sodium hydroxide, acid casein, dipotassium hydrogen phosphate and maltose in the raw materials shown in Table 32 below were mixed in warm water at 60°C in the proportions shown in Table 32. Then, the remaining raw materials (hydrogenated palm kernel oil, monoglycerol fatty acid esters and sorbitan fatty acid esters, caryophyllene, furfural) were added to the resulting mixed solution in the proportions shown in Table 32 and mixed. The resulting mixture was stirred at 8000 rpm for 15 minutes using a homomixer (product name: "LABOLUTION", manufactured by PRIMIX Co., Ltd.) to pre-emulsify it. Then, the resulting emulsion was heated at 95°C for 30 minutes using a water bath (product name: "EC-Water Bath", manufactured by AS ONE Co., Ltd.), and then homogenized at 400 kg / cm 2 The homogenized emulsion was spray-dried using a spray dryer (product name: "Mini SprayDryer B-290", manufactured by BUCHI) at an intake temperature of 180°C and an exhaust temperature of 90°C to obtain non-dairy creamers (model non-dairy creamers 14 to 17).

[1087] [Table 32]

[1088]

[1089] The raw materials used in the preparation of the model non-dairy creamers 14 to 17 were the same as those used in the preparation of the model non-dairy creamers 1 to 4.

[1090] <Preparation of Evaluation Samples (Coffee Au Lait from Test Areas 18 to 21)>

[1091] In a cup, add the amounts of commercially available instant coffee powder (manufactured by Ajinomoto AGF Co., Ltd.), any one of model non-dairy creamer 16 to 19, and sugar (manufactured by Mitsui Sugar Co., Ltd.) shown in Table 33 below, pour in 180 mL of boiling water, and stir for a few seconds until the powder is completely dissolved to prepare the au gratin coffee for test areas 18 to 21 respectively.

[1092] [Table 33]

[1093]

[1094] <Sensory Evaluation>

[1095] The mouth coating feeling, milk feeling, and roasted coffee feeling of the café au lait of Test Sections 18 to 21 were evaluated in the same manner as in Test Example 16. The evaluation results are shown in Table 34 below.

[1096] [Table 34]

[1097]

[1098] As shown in Table 34, when the ratio of furfural is higher than that of β-caryophyllene, the roasted taste of coffee tends to be sufficiently enhanced.

[1099] In addition, it is considered that the roasted coffee of the sample of test section 21 was too strong, and therefore the mouth coating feeling and milk feeling could not be fully evaluated.

[1100] Industrial Applicability

[1101] According to the present invention, a mouth-coating feeling enhancer capable of enhancing the mouth-coating feeling and a method for producing the same can be provided.

[1102] Furthermore, according to the present invention, a food having an enhanced oral coating feeling and a method for producing the same can be provided.

[1103] Furthermore, according to the present invention, a method for enhancing the oral coating feeling can be provided.

[1104] Furthermore, according to the present invention, a coffee roasting enhancer capable of enhancing the roasting sensation of coffee and a method for producing the same can be provided.

[1105] Furthermore, according to the present invention, a coffee beverage having an enhanced coffee roasting sensation and a method for producing the same can be provided.

[1106] Furthermore, according to the present invention, a method for enhancing the roasted taste of coffee can be provided.

[1107] This application is based on Japanese Patent Application No. 2019-046558 (filing date: March 13, 2019) filed in Japan, the entire contents of which are incorporated herein by reference.

Claims

1. An agent for enhancing oral coating sensation, comprising the following heated product (B), The heated product of (B) is a product obtained by heating the component (B) in fats and oils. The oil is at least one selected from the group consisting of rapeseed oil, corn oil, soybean oil, sesame oil, rice oil, rice bran oil, safflower oil, coconut oil, palm oil, palm kernel oil, sunflower oil, perilla oil, wild sesame oil, linseed oil, olive oil, grape seed oil, medium-chain fatty acid oil, animal fat, transesterified oils of these oils and solidified oils of these oils, The concentration of the component (B) in the oil and fat during heating is 10 to 10,000 ppm by weight. (B) at least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene-like compounds, The β-caryophyllene-like compound is at least one compound selected from the group consisting of isocaryophyllene, β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, eugenol, limonene, 4-vinylphenol, linalool, linalool oxide, p-cymene, farnesene, myrcene, ocimene, α-phellandrene, α-terpinene, γ-terpinene and terpinolene.

2. The oral coating enhancer according to claim 1, wherein: Further comprising the following heated product (A), wherein (A) consists of the components (A1) and (A2), (A1) A compound represented by the general formula (I): In the formula, R 1 It is an acyl group, a hydroxyl group or a pyrrol group having 1 to 6 carbon atoms; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 2 is a substituent; n represents an integer from 0 to 3, (A2) at least one selected from the group consisting of aliphatic aldehydes having 3 to 14 carbon atoms, aromatic aldehydes having 7 to 12 carbon atoms, aliphatic alcohols having 3 to 12 carbon atoms, and substances that generate at least one of these compounds upon heating.

3. The oral coating enhancer according to claim 2, wherein: In the general formula (I), R 1 is formyl or acetyl, and Z is a single bond, or In the general formula (I), R 1 is hydroxy or pyrrolyl, and Z is methylene.

4. The oral coating feeling enhancer according to claim 2 or 3, wherein R 2 It is an alkyl group having 1 to 6 carbon atoms.

5. The oral coating enhancer according to claim 2 or 3, wherein: n represents 0 or 1.

6. The oral coating feeling enhancer according to claim 2 or 3, wherein: The compound represented by the general formula (I) is at least one compound selected from the group consisting of furfural, 5-methylfurfural, 2-furanylmethyl ketone, furfuryl alcohol and 1-furfurylpyrrole.

7. The oral coating feeling enhancer according to claim 2 or 3, wherein: The (A2) is oil.

8. The oral coating enhancer according to claim 2, wherein: The concentration of the component (A1) in the medium during heating is 0.0008 to 12000 ppm by weight.

9. The oral coating feeling enhancer according to claim 2, wherein: The concentration of the component (A1) in the medium during heating is 0.08 to 120 ppm by weight.

10. The oral coating enhancer according to claim 2, wherein: The amount of component (A1) heated to obtain a heated product of component (A) is referred to as A1 1 , and the amount of component (B) heated to obtain the heated product of component (B) is referred to as B 1 When B 1 With A1 1 B 1 :A1 1 In the range of 1:0.08~1200, A1 1 With B 1 The unit is weight. The oral coating feeling enhancer according to claim 1 or 2, which is used for fat-containing foods.

12. A method for enhancing oral coating sensation, comprising: A step of adding the following heated material (B), The heated product of (B) is a product obtained by heating the component (B) in fats and oils. The oil is at least one selected from the group consisting of rapeseed oil, corn oil, soybean oil, sesame oil, rice oil, rice bran oil, safflower oil, coconut oil, palm oil, palm kernel oil, sunflower oil, perilla oil, wild sesame oil, linseed oil, olive oil, grape seed oil, medium-chain fatty acid oil, animal fat, transesterified oils of these oils and solidified oils of these oils, The concentration of the component (B) in the oil and fat during heating is 10 to 10,000 ppm by weight. (B) at least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene-like compounds, The β-caryophyllene-like compound is at least one compound selected from the group consisting of isocaryophyllene, β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, eugenol, limonene, 4-vinylphenol, linalool, linalool oxide, p-cymene, farnesene, myrcene, ocimene, α-phellandrene, α-terpinene, γ-terpinene and terpinolene.

13. The method for enhancing the oral coating feeling according to claim 12, wherein: further comprising the step of adding the following heated material (A), (A) is composed of components (A1) and (A2), (A1) A compound represented by the general formula (I): In the formula, R 1 It is an acyl group, a hydroxyl group or a pyrrol group having 1 to 6 carbon atoms; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 2 is a substituent; n represents an integer from 0 to 3, (A2) at least one selected from the group consisting of aliphatic aldehydes having 3 to 14 carbon atoms, aromatic aldehydes having 7 to 12 carbon atoms, aliphatic alcohols having 3 to 12 carbon atoms, and substances that generate at least one of these compounds upon heating.

14. The method for enhancing the oral coating feeling according to claim 13, wherein: In the general formula (I), R 1 is formyl or acetyl, and Z is a single bond, or In the general formula (I), R 1 is hydroxy or pyrrolyl, and Z is methylene.

15. The method for enhancing the oral coating feeling according to claim 13 or 14, wherein: R 2 It is an alkyl group having 1 to 6 carbon atoms.

16. The method for enhancing the oral coating feeling according to claim 13 or 14, wherein: n represents 0 or 1.

17. The method for enhancing oral coating feeling according to claim 13 or 14, wherein: The compound represented by the general formula (I) is at least one compound selected from the group consisting of furfural, 5-methylfurfural, 2-furanylmethyl ketone, furfuryl alcohol and 1-furfurylpyrrole.

18. The method for enhancing oral coating feeling according to claim 13 or 14, wherein: The (A2) is oil.

19. The method for enhancing the oral coating feeling according to claim 13, wherein: The concentration of the component (A1) in the medium during heating is 0.0008 to 12000 ppm by weight.

20. The method for enhancing oral coating feeling according to claim 13, wherein: The concentration of the component (A1) in the medium during heating is 0.08 to 120 ppm by weight.

21. The method for enhancing oral coating feeling according to claim 13, wherein: The amount of component (A1) heated to obtain a heated product of component (A) is referred to as A1 1 , and the amount of component (B) heated to obtain the heated product of component (B) is referred to as B 1 When B 1 With A1 1 B 1 :A1 1 In the range of 1:0.08~1200, A1 1 With B 1 The unit is weight.

22. The method for enhancing the oral coating feeling according to claim 12 or 13, which is a method for enhancing the oral coating feeling of fat-containing food.

23. A method for producing a food, comprising: The following step (B) is heated in oil and fat. The oil is at least one selected from the group consisting of rapeseed oil, corn oil, soybean oil, sesame oil, rice oil, rice bran oil, safflower oil, coconut oil, palm oil, palm kernel oil, sunflower oil, perilla oil, wild sesame oil, linseed oil, olive oil, grape seed oil, medium-chain fatty acid oil, animal fat, transesterified oils of these oils and solidified oils of these oils, The concentration of the component (B) in the oil and fat during heating is 10 to 10,000 ppm by weight. (B) at least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene-like compounds, The β-caryophyllene-like compound is at least one compound selected from the group consisting of isocaryophyllene, β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, eugenol, limonene, 4-vinylphenol, linalool, linalool oxide, p-cymene, farnesene, myrcene, ocimene, α-phellandrene, α-terpinene, γ-terpinene and terpinolene.

24. The manufacturing method according to claim 23, wherein: Further comprising the step of heating the following (A), (A) is composed of components (A1) and (A2), (A1) A compound represented by the general formula (I): In the formula, R 1 It is an acyl group, a hydroxyl group or a pyrrol group having 1 to 6 carbon atoms; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 2 is a substituent; n represents an integer from 0 to 3, (A2) at least one selected from the group consisting of aliphatic aldehydes having 3 to 14 carbon atoms, aromatic aldehydes having 7 to 12 carbon atoms, aliphatic alcohols having 3 to 12 carbon atoms, and substances that generate at least one of these compounds upon heating.

25. The manufacturing method according to claim 24, wherein: In the general formula (I), R 1 is formyl or acetyl, and Z is a single bond, or In the general formula (I), R 1 is hydroxy or pyrrolyl, and Z is methylene.

26. The manufacturing method according to claim 24 or 25, wherein: R 2 It is an alkyl group having 1 to 6 carbon atoms.

27. The manufacturing method according to claim 24 or 25, wherein: n represents 0 or 1.

28. The manufacturing method according to claim 24 or 25, wherein: The compound represented by the general formula (I) is at least one compound selected from the group consisting of furfural, 5-methylfurfural, 2-furanylmethyl ketone, furfuryl alcohol and 1-furfurylpyrrole.

29. The manufacturing method according to claim 24 or 25, wherein: The (A2) is oil.

30. The manufacturing method according to claim 24 or 25, wherein: The heating temperature of the component (A) is 40 to 200° C., and the heating time is 0.1 to 500 minutes. The heating temperature of the component (B) is 40 to 200° C., and the heating time is 0.1 to 500 minutes.

31. The manufacturing method according to claim 24, wherein: The concentration of the component (A1) in the medium during heating is 0.0008 to 12000 ppm by weight.

32. The manufacturing method according to claim 24, wherein: The concentration of the component (A1) in the medium during heating is 0.08 to 120 ppm by weight.

33. The manufacturing method according to claim 24, wherein: The amount of component (A1) heated to obtain a heated product of component (A) is referred to as A1 1 , and the amount of component (B) heated to obtain the heated product of component (B) is referred to as B 1 When B 1 With A1 1 B 1 :A1 1 In the range of 1:0.08~1200, A1 1 With B 1 The unit is weight.

34. The manufacturing method according to claim 23 or 24, wherein: The food product is a food product having an enhanced oral coating sensation.

35. The manufacturing method according to claim 23 or 24, wherein: The food is a fat-containing food.

36. A food comprising the following heated product (B), The heated product of (B) is a product obtained by heating the component (B) in fats and oils. The oil is at least one selected from the group consisting of rapeseed oil, corn oil, soybean oil, sesame oil, rice oil, rice bran oil, safflower oil, coconut oil, palm oil, palm kernel oil, sunflower oil, perilla oil, wild sesame oil, linseed oil, olive oil, grape seed oil, medium-chain fatty acid oil, animal fat, transesterified oils of these oils and solidified oils of these oils, The concentration of the component (B) in the oil and fat during heating is 10 to 10,000 ppm by weight. (B) at least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene-like compounds, The β-caryophyllene-like compound is at least one compound selected from the group consisting of isocaryophyllene, β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, eugenol, limonene, 4-vinylphenol, linalool, linalool oxide, p-cymene, farnesene, myrcene, ocimene, α-phellandrene, α-terpinene, γ-terpinene and terpinolene.

37. The food product according to claim 36, wherein Further comprising the following heated product (A), (A) is composed of components (A1) and (A2), (A1) A compound represented by the general formula (I): In the formula, R 1 It is an acyl group, a hydroxyl group or a pyrrol group having 1 to 6 carbon atoms; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 2 is a substituent; n represents an integer from 0 to 3, (A2) at least one selected from the group consisting of aliphatic aldehydes having 3 to 14 carbon atoms, aromatic aldehydes having 7 to 12 carbon atoms, aliphatic alcohols having 3 to 12 carbon atoms, and substances that generate at least one of these compounds upon heating.

38. A method for producing an agent for enhancing oral coating sensation, comprising the step of heating the following (B) in fats and oils, The oil is at least one selected from the group consisting of rapeseed oil, corn oil, soybean oil, sesame oil, rice oil, rice bran oil, safflower oil, coconut oil, palm oil, palm kernel oil, sunflower oil, perilla oil, wild sesame oil, linseed oil, olive oil, grape seed oil, medium-chain fatty acid oil, animal fat, transesterified oils of these oils and solidified oils of these oils, The concentration of the component (B) in the oil and fat during heating is 10 to 10,000 ppm by weight. (B) at least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene-like compounds, The β-caryophyllene-like compound is at least one compound selected from the group consisting of isocaryophyllene, β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, eugenol, limonene, 4-vinylphenol, linalool, linalool oxide, p-cymene, farnesene, myrcene, ocimene, α-phellandrene, α-terpinene, γ-terpinene and terpinolene.

39. The manufacturing method according to claim 38, wherein: Further comprising the step of heating the following (A), (A) is composed of components (A1) and (A2), (A1) A compound represented by the general formula (I): In the formula, R 1 It is an acyl group, a hydroxyl group or a pyrrol group having 1 to 6 carbon atoms; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 2 is a substituent; n represents an integer from 0 to 3, (A2) at least one selected from the group consisting of aliphatic aldehydes having 3 to 14 carbon atoms, aromatic aldehydes having 7 to 12 carbon atoms, aliphatic alcohols having 3 to 12 carbon atoms, and substances that generate at least one of these compounds upon heating.

40. The manufacturing method according to claim 39, wherein: In the general formula (I), R 1 is formyl or acetyl, and Z is a single bond, or In the general formula (I), R 1 is hydroxy or pyrrolyl, and Z is methylene.

41. The manufacturing method according to claim 39 or 40, wherein: R 2 It is an alkyl group having 1 to 6 carbon atoms.

42. The manufacturing method according to claim 39 or 40, wherein: n represents 0 or 1.

43. The manufacturing method according to claim 39 or 40, wherein: The compound represented by the general formula (I) is at least one compound selected from the group consisting of furfural, 5-methylfurfural, 2-furanylmethyl ketone, furfuryl alcohol and 1-furfurylpyrrole.

44. The manufacturing method according to claim 39 or 40, wherein: The (A2) is oil.

45. The manufacturing method according to claim 39 or 40, wherein: The heating temperature of the component (A) is 40 to 200° C., and the heating time is 0.1 to 500 minutes. The heating temperature of the component (B) is 40 to 200° C., and the heating time is 0.1 to 500 minutes.

46. ​​The manufacturing method according to claim 39, wherein: The concentration of the component (A1) in the medium during heating is 0.0008 to 12000 ppm by weight.

47. The manufacturing method according to claim 39, wherein: The concentration of the component (A1) in the medium during heating is 0.08 to 120 ppm by weight.

48. The manufacturing method according to claim 39, wherein: The amount of component (A1) heated to obtain a heated product of component (A) is referred to as A1 1 , and the amount of component (B) heated to obtain the heated product of component (B) is referred to as B 1 When B 1 With A1 1 B 1 :A1 1 In the range of 1:0.08~1200, A1 1 With B 1 The unit is weight.

49. The manufacturing method according to claim 38 or 39, wherein: Mouth coating enhancers are used in oily foods.

50. A coffee roasting enhancer, comprising a heated product of the following (A) and (B), The heated product of (A) and (B) is obtained by mixing (A) and (B) and heating them when preparing the coffee roasting enhancer. (A) is composed of components (A1) and (A2), (A1) A compound represented by the general formula (I): In the formula, R 1 It is an acyl group, a hydroxyl group or a pyrrol group having 1 to 6 carbon atoms; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 2 is a substituent; n represents an integer from 0 to 3, (A2) at least one selected from the group consisting of aliphatic aldehydes having 3 to 14 carbon atoms, aromatic aldehydes having 7 to 12 carbon atoms, aliphatic alcohols having 3 to 12 carbon atoms, and substances that generate at least one of these compounds upon heating, (B) at least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene-like compounds, The β-caryophyllene-like compound is at least one compound selected from the group consisting of isocaryophyllene, β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, eugenol, limonene, 4-vinylphenol, linalool, linalool oxide, p-cymene, farnesene, myrcene, ocimene, α-phellandrene, α-terpinene, γ-terpinene and terpinolene, The heated product of (B) is a product obtained by heating the component (B) in fats and oils. The oil is at least one selected from the group consisting of rapeseed oil, corn oil, soybean oil, sesame oil, rice oil, rice bran oil, safflower oil, coconut oil, palm oil, palm kernel oil, sunflower oil, perilla oil, wild sesame oil, linseed oil, olive oil, grape seed oil, medium-chain fatty acid oil, animal fat, transesterified oils of these oils and solidified oils of these oils, The concentration of the component (B) in the oil and fat during heating is 0.0008 to 50,000 ppm by weight. The amount of component (A1) heated to obtain a heated product of component (A) is referred to as A1 1 , and the amount of component (B) heated to obtain the heated product of component (B) is referred to as B 1 When B 1 With A1 1 B 1 :A1 1 In the range of 1:1 to 10, A1 1 With B 1 The unit is weight.

51. The coffee roasting enhancer according to claim 50, wherein In the general formula (I), R 1 is formyl or acetyl, and Z is a single bond, or In the general formula (I), R 1 is hydroxy or pyrrolyl, and Z is methylene.

52. The coffee roasting enhancer according to claim 50 or 51, wherein R 2 It is an alkyl group having 1 to 6 carbon atoms.

53. The coffee roasting enhancer according to claim 50 or 51, wherein n represents 0 or 1.

54. The coffee roasting enhancer according to claim 50 or 51, wherein The compound represented by the general formula (I) is at least one compound selected from the group consisting of furfural, 5-methylfurfural, 2-furanylmethyl ketone, furfuryl alcohol and 1-furfurylpyrrole.

55. The coffee roasting enhancer according to claim 50 or 51, wherein The (A2) is oil.

56. The coffee roasting enhancer according to claim 50, wherein The concentration of the component (A1) in the medium during heating is 0.0008 to 12000 ppm by weight.

57. The coffee roasting enhancer according to claim 50, wherein The concentration of the component (A1) in the medium during heating is 0.08 to 120 ppm by weight.

58. The coffee roasting enhancer according to claim 50, wherein The concentration of the component (B) in the medium during heating is 0.08 to 120 ppm by weight.

59. A method for enhancing coffee roasting sensation, comprising: A step of adding the following heated products (A) and (B), The method for enhancing the roasted coffee feeling comprises mixing (A) and (B) and heating them when preparing a roasted coffee feeling enhancer, (A) is composed of components (A1) and (A2), (A1) A compound represented by the general formula (I): In the formula, R 1 It is an acyl group, a hydroxyl group or a pyrrol group having 1 to 6 carbon atoms; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 2 is a substituent; n represents an integer from 0 to 3, (A2) at least one selected from the group consisting of aliphatic aldehydes having 3 to 14 carbon atoms, aromatic aldehydes having 7 to 12 carbon atoms, aliphatic alcohols having 3 to 12 carbon atoms, and substances that generate at least one of these compounds upon heating, (B) at least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene-like compounds, The β-caryophyllene-like compound is at least one compound selected from the group consisting of isocaryophyllene, β-pinene, sabinene, 4-allyl-2,6-dimethoxyphenol, eugenol, limonene, 4-vinylphenol, linalool, linalool oxide, p-cymene, farnesene, myrcene, ocimene, α-phellandrene, α-terpinene, γ-terpinene, and terpinolene The heated product of (B) is a product obtained by heating the component (B) in fats and oils. The oil is at least one selected from the group consisting of rapeseed oil, corn oil, soybean oil, sesame oil, rice oil, rice bran oil, safflower oil, coconut oil, palm oil, palm kernel oil, sunflower oil, perilla oil, wild sesame oil, linseed oil, olive oil, grape seed oil, medium-chain fatty acid oil, animal fat, transesterified oils of these oils and solidified oils of these oils, The concentration of the component (B) in the oil and fat during heating is 0.0008 to 50,000 ppm by weight. The amount of component (A1) heated to obtain a heated product of component (A) is referred to as A1 1 , and the amount of component (B) heated to obtain the heated product of component (B) is referred to as B 1 When B 1 With A1 1 B 1 :A1 1 In the range of 1:1 to 10, A1 1 With B 1 The unit is weight.

60. The method for enhancing coffee roasting sensation according to claim 59, wherein: In the general formula (I), R 1 is formyl or acetyl, and Z is a single bond, or In the general formula (I), R 1 is hydroxy or pyrrolyl, and Z is methylene.

61. The method for enhancing the roasted taste of coffee according to claim 59 or 60, wherein: R 2 It is an alkyl group having 1 to 6 carbon atoms.

62. The method for enhancing the roasted taste of coffee according to claim 59 or 60, wherein: n represents 0 or 1.

63. The method for enhancing coffee roasting sensation according to claim 59 or 60, wherein: The compound represented by the general formula (I) is at least one compound selected from the group consisting of furfural, 5-methylfurfural, 2-furanylmethyl ketone, furfuryl alcohol and 1-furfurylpyrrole.

64. The method for enhancing the roasted taste of coffee according to claim 59 or 60, wherein: The (A2) is oil.

65. The method for enhancing coffee roasting sensation according to claim 59, wherein: The concentration of the component (A1) in the medium during heating is 0.0008 to 12000 ppm by weight.

66. The method for enhancing the roasted taste of coffee according to claim 59, wherein: The concentration of the component (A1) in the medium during heating is 0.08 to 120 ppm by weight.

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