Mouth coating enhancer
Patent Information
- Application Number
- JP2021505142
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2019-03-13
- Filing Date
- 2020-03-12
- Publication Date
- 2025-02-19
- Estimated Expiration
- 2040-03-12
AI Technical Summary
【0070】 本発明によれば、マウスコーティング感を増強することができるマウスコーティング感増強剤及びその製造方法を提供し得る。 また本発明によれば、マウスコーティング感が増強された食品及びその製造方法を提供し得る。 また本発明によれば、マウスコーティング感の増強方法を提供し得る。 また本発明によれば、コーヒー焙煎感を増強することができるコーヒー焙煎感増強剤及びその製造方法を提供し得る。 また本発明によれば、コーヒー焙煎感が増強されたコーヒー飲料及びその製造方法を提供し得る。 また本発明によれば、コーヒー焙煎感の増強方法を提供し得る。
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Abstract
Description
[Technical field]
[0001] The present invention relates to a mouth-coating feel enhancer and a method for producing the same. The present invention also relates to a food with enhanced mouth-coating feel and a method for producing the same, and a method for enhancing mouth-coating feel. The present invention further relates to a coffee roasting feel enhancer and a method for producing the same, and a method for enhancing coffee roasting feel, etc. [Background technology]
[0002] The "mouth-coating feeling" refers to the feeling that the inside of the mouth is coated with a thin film, the feeling that the inside of the mouth is coated with oil or an oil-like film, the smooth feeling felt in the mouth, and the thick oil-like feeling (thickness) that spreads throughout the mouth, which are noticeable when oils or fats, or solutions or foods containing oils or fats, are taken into the mouth. If there was a method for easily enhancing the mouth-coating feeling, for example, even a small amount of oil or fat could be sufficiently provided with the pleasant feeling that is noticeable when oils or fats are taken into the mouth, which is thought to have the advantage of suppressing excessive calorie intake and also being expected to be effective in preventing metabolic diseases such as obesity.
[0003] Methods for enhancing the mouth-coating sensation have been reported in the past, such as those utilizing hydrocolloids, low molecular weight compounds, polyphenols, or glycosides (Non-Patent Documents 1 to 5). However, the sensation enhanced by any of these methods has a problem in that it is different in quality from the mouth-coating sensation that is prominent when oils or fats are placed in the oral cavity. [Prior art documents] [Non-patent literature]
[0004] [Non-Patent Document 1] Arocas et al., “Sensory properties determined by starch type in white sauces: effects of freeze / thaw and hydrocolloid addition.” J Food Sci 2010, 75:S132-S140. [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. [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. [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. [Non-Patent Document 5] Scharbert et al., “Identification of the astringent taste compounds in black tea infusions by combining instrumental analysis and human bioresponse.” J Agric and Food Chem 2004, 52:3498-3508. Summary of the Invention [Problem to be solved by the invention]
[0005] The present invention has been made in view of the above circumstances, and an object of the present invention is to provide an effective mouth-coating feel enhancer. Another object of the present invention is to provide an effective coffee roast feel enhancer. [Means for solving the problem]
[0006] As a result of intensive research into the above-mentioned problems, the inventors have found that a heated product obtained by heating a specific compound can enhance the mouth-coating feeling. The inventors have also newly found that the heated product can enhance the roasted coffee feeling. Furthermore, the inventors have also found that a specific compound that can be generated in the heated product can enhance the mouth-coating feeling and the roasted coffee feeling. The inventors have further researched based on these findings and have completed the present invention. That is, the present invention is as follows.
[0007] [1] A mouth-coating feel enhancer comprising a heated product of the following (A) and / or (B), or at least one compound selected from the following compound group (C): (A)(A1) General formula (I):
[0008] [ka]
[0009] [During the ceremony, R 1 represents an acyl group having 1 to 6 carbon atoms, a hydroxy group, or a pyrrole group; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 2 is a substituent; n represents an integer of 0 to 3. Compounds represented by the formula: (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 upon heating; (B) at least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene analogues [Compound group (C)] β-Caryophyllene oxide α-Pinene oxide Limonene oxide α-Terpinenol General formula (II):
[0010] [ka]
[0011] [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. A compound represented by General formula (III):
[0012] [ka]
[0013] [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. A compound represented by General formula (IV):
[0014] [ka]
[0015] [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. A compound represented by General formula (V):
[0016] [ka]
[0017] [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. A compound represented by (1S,6S,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecane-5-one (1S,6R,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecane-5-one (1R,4R,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carboxaldehyde (1R,4S,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carboxaldehyde (1S,2S,5R,9S)-1,4,4,8-Tetramethyl-12-oxatricyclo[7.2.1.0 2,5 ]Dodes-7-En (1R,2S,5R,8R,9R)-1,4,4,8-Tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ]Dodecan-9-ol (1R,2S,5R,8R,9S)-1,4,4,8-Tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ]Dodecan-9-ol [1R-(1α,2α,5β,8β,9α)]-4,4,8-trimethyl-tricyclo[6.3.1.0 2,5 ]dodecane-1,9-diol [2] R in the above general formula (I) 1 is a formyl group or an acetyl group and Z is a single bond, or R in the general formula (I)1 The mouse-coating sensation enhancer according to [1], wherein is a hydroxy group or a pyrrole group, and Z is a methylene group. [3] R 2 wherein the alkyl group is an alkyl group having 1 to 6 carbon atoms. [4] The mouse-coating feel enhancer according to any one of [1] to [3], wherein n represents 0 or 1. [5] A mouth-coating sensation 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-furyl methyl ketone, furfuryl alcohol, and 1-furfurylpyrrole. [6] The mouth-coating feel enhancer according to any one of [1] to [5], wherein (A2) is an oil or fat. [7] The mouth-coating sensation enhancer according to any one of [1] to [6], wherein the β-caryophyllene analogue 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). [8] The mouth-coating feel enhancer according to [1], wherein the 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, clobandiol, clobandiol-3-monoacetate, clobandiol diacetate and clobandiol-3-monoisovalerate. [9] The mouth-coating feel enhancer according to any one of [1] to [8], which is for use in foods containing fats and oils.
[10] A method for enhancing mouth-coating sensation, comprising adding a heated product of the following (A) and / or (B), or at least one compound selected from the following compound group (C): (A)(A1) General formula (I):
[0018] [ka]
[0019] [During the ceremony, R 1 represents an acyl group having 1 to 6 carbon atoms, a hydroxy group, or a pyrrole group; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 2 is a substituent; n represents an integer of 0 to 3. Compounds represented by the formula: (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 upon heating; (B) at least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene analogues [Compound group (C)] β-Caryophyllene oxide α-Pinene oxide Limonene oxide α-Terpinenol General formula (II):
[0020] [ka]
[0021] [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. A compound represented by General formula (III):
[0022] [ka]
[0023] [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. A compound represented by General formula (IV):
[0024] [ka]
[0025] [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. A compound represented by General formula (V):
[0026] [ka]
[0027] [In the formula, R7 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. A compound represented by (1S,6S,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecane-5-one (1S,6R,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecane-5-one (1R,4R,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carboxaldehyde (1R,4S,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carboxaldehyde (1S,2S,5R,9S)-1,4,4,8-Tetramethyl-12-oxatricyclo[7.2.1.0 2,5 ]Dodes-7-En (1R,2S,5R,8R,9R)-1,4,4,8-Tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ]Dodecan-9-ol (1R,2S,5R,8R,9S)-1,4,4,8-Tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ]Dodecan-9-ol [1R-(1α,2α,5β,8β,9α)]-4,4,8-trimethyl-tricyclo[6.3.1.0 2,5 ]dodecane-1,9-diol
[11] R in the above general formula (I) 1 is a formyl group or an acetyl group and Z is a single bond, or R in the general formula (I) 1 The method for enhancing mouth-coating sensation described in
[10] , wherein is a hydroxy group or a pyrrole group, and Z is a methylene group.
[12] R 2 wherein the alkyl group has 1 to 6 carbon atoms.
[13] The method for enhancing mouth-coating feeling according to any one of
[10] to
[12] , wherein n represents 0 or 1.
[14] A method for enhancing mouth-coating sensation described in 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-furyl methyl ketone, furfuryl alcohol, and 1-furfurylpyrrole.
[15] The method for enhancing mouth-coating feeling according to any one of
[10] to
[14] , wherein (A2) is an oil or fat.
[16] The method for enhancing mouth-coating sensation according to any one of
[10] to
[15] , wherein the β-caryophyllene analogue 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).
[17] The method for enhancing mouth-coating feel according to
[10] , wherein the 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, clobandiol, clobandiol-3-monoacetate, clobandiol diacetate and clobandiol-3-monoisovalerate.
[18] The method for enhancing a mouth-coating feeling of an oil-containing food according to any one of
[10] to
[17] , which is a method for enhancing a mouth-coating feeling of an oil-containing food.
[19] A method for producing a food, comprising heating the following (A) and / or (B) or adding at least one compound selected from the following compound group (C): (A)(A1) General formula (I):
[0028] [ka]
[0029] [During the ceremony, R 1 represents an acyl group having 1 to 6 carbon atoms, a hydroxy group, or a pyrrole group; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 2 is a substituent; n represents an integer of 0 to 3. Compounds represented by the formula: (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 upon heating; (B) at least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene analogues [Compound group (C)] β-Caryophyllene oxide α-Pinene oxide Limonene oxide α-Terpinenol General formula (II):
[0030] [ka]
[0031] [In the formula, R 3 and R 4each independently represents a hydrogen atom, an acyl group having 1 to 18 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. A compound represented by General formula (III):
[0032] [ka]
[0033] [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. A compound represented by General formula (IV):
[0034] [ka]
[0035] [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. A compound represented by General formula (V):
[0036] [ka]
[0037] [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. A compound represented by (1S,6S,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecane-5-one (1S,6R,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecane-5-one (1R,4R,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carboxaldehyde (1R,4S,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carboxaldehyde (1S,2S,5R,9S)-1,4,4,8-Tetramethyl-12-oxatricyclo[7.2.1.0 2,5 ]Dodes-7-En (1R,2S,5R,8R,9R)-1,4,4,8-Tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ]Dodecan-9-ol (1R,2S,5R,8R,9S)-1,4,4,8-Tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ]Dodecan-9-ol [1R-(1α,2α,5β,8β,9α)]-4,4,8-trimethyl-tricyclo[6.3.1.0 2,5 ]dodecane-1,9-diol
[20] R in the above general formula (I) 1 is a formyl group or an acetyl group and Z is a single bond, or R in the general formula (I) 1 is a hydroxy group or a pyrrole group, and Z is a methylene group.
[21] R 2 wherein R is an alkyl group having 1 to 6 carbon atoms.
[22] The method according to any one of
[19] to
[21] , wherein n represents 0 or 1.
[23] The 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-furyl methyl ketone, furfuryl alcohol, and 1-furfurylpyrrole.
[24] The method according to any one of
[19] to
[23] , wherein (A2) is an oil or fat.
[25] The method according to any one of
[19] to
[24] , wherein the β-caryophyllene analogue 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).
[26] The heating temperature of the component (A) is 40 to 200° C., and the heating time is 0.1 to 500 minutes. The method according to any one of
[19] to
[25] , wherein the heating temperature of the component (B) is 40 to 200° C., and the heating time is 0.1 to 500 minutes.
[27] The method according to
[19] , wherein the 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, clobandiol, clobandiol-3-monoacetate, clobandiol diacetate and clobandiol-3-monoisovalerate.
[28] The method for producing a food product according to any one of
[19] to
[27] , wherein the food product has an enhanced mouth-coating feel.
[29] The method for producing a food product according to any one of
[19] to
[28] , wherein the food product is an oil-containing food product.
[30] A heated product of the following (A) and / or (B), or a food containing at least one compound selected from the following compound group (C): (A)(A1) General formula (I):
[0038] [ka]
[0039] [During the ceremony, R 1 represents an acyl group having 1 to 6 carbon atoms, a hydroxy group, or a pyrrole group; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 2 is a substituent; n represents an integer of 0 to 3. Compounds represented by the formula: (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 upon heating; (B) at least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene analogues [Compound group (C)] β-Caryophyllene oxide α-Pinene oxide Limonene oxide α-Terpinenol General formula (II):
[0040] [ka]
[0041] [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. A compound represented by General formula (III):
[0042] [ka]
[0043] [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. A compound represented by General formula (IV):
[0044] [ka]
[0045] [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. A compound represented by General formula (V):
[0046] [ka]
[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. A compound represented by (1S,6S,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecane-5-one (1S,6R,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecane-5-one (1R,4R,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carboxaldehyde (1R,4S,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carboxaldehyde (1S,2S,5R,9S)-1,4,4,8-Tetramethyl-12-oxatricyclo[7.2.1.0 2,5 ]Dodes-7-En (1R,2S,5R,8R,9R)-1,4,4,8-Tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ]Dodecan-9-ol (1R,2S,5R,8R,9S)-1,4,4,8-Tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ]Dodecan-9-ol [1R-(1α,2α,5β,8β,9α)]-4,4,8-trimethyl-tricyclo[6.3.1.0 2,5 ]dodecane-1,9-diol
[31] A method for producing a mouth-coating feel enhancer, comprising heating the following (A) and / or (B): (A)(A1) General formula (I):
[0048] [ka]
[0049] [During the ceremony, R 1 represents an acyl group having 1 to 6 carbon atoms, a hydroxy group, or a pyrrole group; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 2 is a substituent; n represents an integer of 0 to 3. Compounds represented by the formula: (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 upon heating; (B) at least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene analogues
[32] R in the above general formula (I) 1is a formyl group or an acetyl group and Z is a single bond, or R in the general formula (I) 1 is a hydroxy group or a pyrrole group, and Z is a methylene group.
[33] R 2 wherein R is an alkyl group having 1 to 6 carbon atoms.
[34] The method according to any one of
[31] to
[33] , wherein n represents 0 or 1.
[35] The 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-furyl methyl ketone, furfuryl alcohol, and 1-furfurylpyrrole.
[36] The method according to any one of
[31] to
[35] , wherein (A2) is an oil or fat.
[37] The method according to any one of
[31] to
[36] , wherein the β-caryophyllene analogue 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).
[38] The heating temperature of the component (A) is 40 to 200° C., and the heating time is 0.1 to 500 minutes. The method according to any one of
[31] to
[37] , wherein the heating temperature of the component (B) is 40 to 200° C., and the heating time is 0.1 to 500 minutes.
[39] The method according to
[31] , wherein the 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, clobandiol, clobandiol-3-monoacetate, clobandiol diacetate and clobandiol-3-monoisovalerate.
[40] The method according to any one of
[31] to
[39] , wherein the mouth-coating sensation enhancer is for use in foods containing fats and oils.
[41] A coffee roasting sensation enhancer comprising a heated product of the following (A) and / or (B), or at least one compound selected from the following compound group (C): (A)(A1) General formula (I):
[0050] [ka]
[0051] [During the ceremony, R 1 represents an acyl group having 1 to 6 carbon atoms, a hydroxy group, or a pyrrole group; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 2 is a substituent; n represents an integer of 0 to 3. Compounds represented by the formula: (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 upon heating; (B) at least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene analogues [Compound group (C)] β-Caryophyllene oxide α-Pinene oxide Limonene oxide α-Terpinenol General formula (II):
[0052] [ka]
[0053] [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. A compound represented by General formula (III):
[0054] [ka]
[0055] [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. A compound represented by General formula (IV):
[0056] [ka]
[0057] [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. A compound represented by General formula (V):
[0058] [ka]
[0059] [In the formula, R 7 and R8 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. A compound represented by (1S,6S,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecane-5-one (1S,6R,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecane-5-one (1R,4R,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carboxaldehyde (1R,4S,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carboxaldehyde (1S,2S,5R,9S)-1,4,4,8-Tetramethyl-12-oxatricyclo[7.2.1.0 2,5 ]Dodes-7-En (1R,2S,5R,8R,9R)-1,4,4,8-Tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ]Dodecan-9-ol (1R,2S,5R,8R,9S)-1,4,4,8-Tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ]Dodecan-9-ol [1R-(1α,2α,5β,8β,9α)]-4,4,8-trimethyl-tricyclo[6.3.1.0 2,5 ]dodecane-1,9-diol
[42] R in the above general formula (I) 1 is a formyl group or an acetyl group and Z is a single bond, or R in the general formula (I) 1 The coffee roasting sensation enhancer according to
[41] , wherein N is a hydroxy group or a pyrrole group, and Z is a methylene group.
[43] R 2 wherein R is an alkyl group having 1 to 6 carbon atoms.
[44] The coffee roasting sensation enhancer according to any one of
[41] to
[43] , wherein n represents 0 or 1.
[45] The coffee roasting sensation enhancer according to any one of
[41] to
[44] , wherein the compound represented by the general formula (I) is at least one compound selected from the group consisting of furfural, 5-methylfurfural, 2-furyl methyl ketone, furfuryl alcohol, and 1-furfurylpyrrole.
[46] The coffee roasting sensation enhancer according to any one of
[41] to
[45] , wherein (A2) is an oil or fat.
[47] The coffee roasting sensation enhancer according to any one of
[41] to
[46] , wherein the β-caryophyllene analogue 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).
[48] The coffee roasting sensation enhancer according to
[41] , wherein the 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, clobandiol, clobandiol-3-monoacetate, clobandiol diacetate, and clobandiol-3-monoisovalerate.
[49] A method for enhancing the roasted taste of coffee, comprising adding a heated product of the following (A) and / or (B), or at least one compound selected from the following compound group (C): (A)(A1) General formula (I):
[0060] [ka]
[0061] [During the ceremony, R 1 represents an acyl group having 1 to 6 carbon atoms, a hydroxy group, or a pyrrole group; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 2 is a substituent; n represents an integer of 0 to 3. Compounds represented by the formula: (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 upon heating; (B) at least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene analogues [Compound group (C)] β-Caryophyllene oxide α-Pinene oxide Limonene oxide α-Terpinenol General formula (II):
[0062] [ka]
[0063] [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. A compound represented by General formula (III):
[0064] [ka]
[0065] [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. A compound represented by General formula (IV):
[0066] [ka]
[0067] [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. A compound represented by General formula (V):
[0068] [ka]
[0069] [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. A compound represented by (1S,6S,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecane-5-one (1S,6R,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecane-5-one (1R,4R,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carboxaldehyde (1R,4S,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carboxaldehyde (1S,2S,5R,9S)-1,4,4,8-Tetramethyl-12-oxatricyclo[7.2.1.0 2,5 ]Dodes-7-En (1R,2S,5R,8R,9R)-1,4,4,8-Tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ]Dodecan-9-ol (1R,2S,5R,8R,9S)-1,4,4,8-Tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ]Dodecan-9-ol [1R-(1α,2α,5β,8β,9α)]-4,4,8-trimethyl-tricyclo[6.3.1.0 2,5 ]dodecane-1,9-diol
[50] R in the above general formula (I) 1 is a formyl group or an acetyl group and Z is a single bond, or R in the general formula (I) 1 is a hydroxy group or a pyrrole group, and Z is a methylene group.
[51] R 2 wherein the alkyl group has 1 to 6 carbon atoms.
[52] The method for enhancing the roast taste of coffee according to any one of
[49] to
[51] , wherein n represents 0 or 1.
[53] The method for enhancing the coffee roasting sensation described in any one of
[49] to
[52] , wherein the compound represented by general formula (I) is at least one compound selected from the group consisting of furfural, 5-methylfurfural, 2-furyl methyl ketone, furfuryl alcohol, and 1-furfurylpyrrole.
[54] The method for enhancing the roasting taste of coffee according to any one of
[49] to
[53] , wherein (A2) is a fat or oil.
[55] The method for enhancing coffee roasting sensation according to any one of
[49] to
[54] , wherein the β-caryophyllene analogue 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).
[56] The method for enhancing coffee roasting sensation according to
[49] , wherein the 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, clobandiol, clobandiol-3-monoacetate, clobandiol diacetate and clobandiol-3-monoisovalerate. Effect of the Invention
[0070] According to the present invention, a mouth-coating feel enhancer capable of enhancing the mouth-coating feel and a method for producing the same can be provided. Furthermore, the present invention can provide a food product having an enhanced mouth-coating feel and a method for producing the same. The present invention can also provide a method for enhancing the mouth-coating sensation. Furthermore, according to the present invention, a coffee roasting sensation enhancer capable of enhancing the roasting sensation of coffee and a method for producing the same can be provided. Furthermore, according to the present invention, a coffee beverage with an enhanced roasted coffee flavor and a method for producing the same can be provided. Furthermore, the present invention can provide a method for enhancing the roasted taste of coffee. [Brief description of the drawings]
[0071] [Figure 1] Figure 1 is a graph showing the results of the two-point discrimination evaluation in Test Example 10. The values in the figure (vertical axis of the graph) indicate the number of times that the mouth-coating feel of evaluation samples 10-1 and 10-2 was selected as being strong when compared under blind conditions (n=9). Also, * in the figure indicates p<0.05. [Diagram 2] Figure 2 is a graph showing the results of the evaluation in Test Example 10. The values in the figure (vertical axis of the graph) indicate the scores (average score ± standard error by three expert panels) obtained by blind sensory evaluation of the strength of the mouth-coating sensation of evaluation samples 10-1 and 10-2 (n=9). Also, * in the figure indicates p<0.05. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0072] <Mouth coating enhancer> In one embodiment, the mouth-coating feel enhancer of the present invention is characterized in that it contains the following heated product (A) and / or (B) as an active ingredient: The following (A), (A1), (A2) and (B) used in the present invention may be referred to herein as "component (A)", "component (A1)", "component (A2)" and "component (B)", respectively. Furthermore, in this specification, a heated product of component (A) and a heated product of component (B) may be referred to herein as "heated product of component (A)" and "heated product of component (B)", respectively.
[0073] (A)(A1) General formula (I):
[0074] [ka]
[0075] [During the ceremony, R 1 represents an acyl group having 1 to 6 carbon atoms, a hydroxy group, or a pyrrole group; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 2 is a substituent; n represents an integer of 0 to 3.
[0076] Compounds represented by the formula: (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 upon heating; (B) at least one compound selected from the group consisting of β-caryophyllene and β-caryophyllene analogues
[0077] In another embodiment, the mouse-coating sensation enhancer of the present invention is characterized in that it contains, as an active ingredient, at least one compound selected from the compound group (C) described below. 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.
[0078] [Component (A)] The component (A) of the present invention comprises the components (A1) and (A2).
[0079] [Component (A1)] In the present invention, the compound represented by formula (I) used as the component (A1) may be referred to as "compound (I)" in this specification. Each group in formula (I) will be explained below.
[0080] R in general formula (I) 1 represents an acyl group having 1 to 6 carbon atoms, a hydroxy group, or a pyrrole group.
[0081] R 1 The "acyl group having 1 to 6 carbon atoms" in the above may be linear or branched, but is preferably linear. The acyl group may be saturated or may 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 a formyl group, an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a valeryl group, an isovaleryl group, a pivaloyl group, and a hexanoyl group, and are preferably a formyl group, an acetyl group, a propionyl group, a butyryl group, or an isobutyryl group, more preferably a formyl group, an acetyl group, or a propionyl group, and particularly preferably a formyl group or an acetyl group.
[0082] R in general formula (I) 1 is preferably an acyl group having 1 to 4 carbon atoms, a hydroxy group, or a pyrrole group, more preferably a formyl group, an acetyl group, a hydroxy group, or a pyrrole group, and particularly preferably a formyl group or an acetyl group.
[0083] In the general formula (I), Z represents a single bond or an alkylene group having 1 to 6 carbon atoms.
[0084] 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 a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group, and are preferably a methylene group, an ethylene group, a trimethylene group, or a tetramethylene group, more preferably a methylene group or an ethylene group, and particularly preferably a methylene group.
[0085] In formula (I), Z 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.
[0086] In one embodiment, compound (I) is 1 is preferably an acyl group having 1 to 6 carbon atoms, and Z is preferably a single bond; R 1 is more preferably an acyl group having 1 to 4 carbon atoms and Z is a single bond; R 1 It is particularly preferred that is a formyl group or an acetyl group and Z is a single bond. In another embodiment, compound (I) is 1 is preferably a hydroxy group or a pyrrole group, and Z is preferably an alkylene group having 1 to 6 carbon atoms; R 1 is more preferably a hydroxy group or a pyrrole group, and Z is an alkylene group having 1 to 4 carbon atoms; R 1 It is particularly preferred that Z is a hydroxy group or a pyrrole group and Z is a methylene group.
[0087] R in general formula (I) 2 R represents a substituent. 2The substituent in is not particularly limited, and 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., ethenyl, 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-butynyl, 3-butynyl, etc.), ), acyl groups having 1 to 6 carbon atoms (e.g., formyl group, acetyl group, propionyl group, butyryl group, isobutyryl group, etc.), alkoxy groups having 1 to 6 carbon atoms (e.g., methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, etc.), hydroxyalkyl groups having 1 to 6 carbon atoms (e.g., hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, etc.), etc., preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and particularly preferably a methyl group.
[0088] In formula (I), n represents an integer of 0 to 3. n preferably represents an integer of 0 to 2, and more preferably represents 0 or 1.
[0089] In one embodiment, when n in general formula (I) is 2 or 3, a plurality of R 2 may be the same or different.
[0090] Preferred compounds (I) are shown below.
[0091] [Compound (IA)] R 1 is a formyl group, an acetyl group, a hydroxy group, or a pyrrole group; Z is a single bond or a methylene group; R 2is a substituent (preferably an alkyl group having 1 to 6 carbon atoms); n is an integer from 0 to 3 Compound (I).
[0092] [Compound (IB)] R 1 is a formyl group, an acetyl group, a hydroxy group, or a pyrrole group; Z is a single bond or a methylene group; R 2 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms); n represents 0 or 1 Compound (I).
[0093] [Compound (IC)] R 1 is an acyl group having 1 to 6 carbon atoms or a hydroxy group; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 2 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms); n is an integer from 0 to 3 Compound (I).
[0094] [Compound (ID)] R 1 is a formyl group, an acetyl group, or a hydroxy group; Z is a single bond or a methylene group; R 2 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms); n is an integer from 0 to 3 Compound (I).
[0095] [Compound (IE)] R 1 is a formyl group, an acetyl group, or a hydroxy group; Z is a single bond or a methylene group; R 2 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms); n represents 0 or 1 Compound (I).
[0096] [Compound (IF)] R 1 is an acyl group having 1 to 6 carbon atoms or a pyrrole group; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 2 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms); n is an integer from 0 to 3 Compound (I).
[0097] [Compound (IG)] R 1 is a formyl group, an acetyl group, or a pyrrole group; Z is a single bond or a methylene group; R 2 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms); n is an integer of 0 to 3 (preferably 0 or 1). Compound (I).
[0098] [Compound (IH)] R 1 is a formyl group, an acetyl group, or a pyrrole group; Z is a single bond or a methylene group; R 2 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms); n represents 0 or 1 Compound (I).
[0099] Specific examples of suitable compounds (I) include: Furfural (CAS registration number: 98-01-1, etc.):
[0100] [ka]
[0101] 5-Methylfurfural (CAS Registry Number: 620-02-0):
[0102] [ka]
[0103] 2-Furyl methyl ketone (CAS registration number: 1192-62-7, etc.):
[0104] [ka]
[0105] Furfuryl alcohol (CAS registration number: 98-00-0, etc.):
[0106] [ka]
[0107] 1-Furfurylpyrrole (CAS registration number: 1438-94-4, etc.):
[0108] [ka]
[0109] Among them, furfural is preferred because it provides clear effects and has good flavor quality.
[0110] There are no particular limitations on the method for producing the component (A1), and it can be produced by a method known per se or a method equivalent thereto, and it may be, for example, a synthetic product or an extract product, etc. Commercially available products can also be used, which is preferable from the viewpoint of simplicity.
[0111] [(A2) component] In the present invention, as the component (A2), 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.
[0112] 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 (an aliphatic aldehyde having no carbon-carbon double bond or triple bond in the molecule) or an unsaturated aliphatic aldehyde (an 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, even more preferably 4 to 10, and particularly preferably 6 to 10. Examples of aliphatic aldehydes that can be used as component (A2) include propanal, butanal, pentanal, 2-pentenal, hexanal, 2-hexenal, 2,4-hexadienal, heptanal, 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, and 3-(methylthio)propanal (methional). Examples include, preferably, hexanal, 2-hexenal, 2,4-hexadienal, heptanal, 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.
[0113] 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 aromatic aldehydes 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, and are preferably benzaldehyde, o-tolualdehyde, m-tolualdehyde, and p-tolualdehyde, and more preferably benzaldehyde and p-tolualdehyde.
[0114] The "aliphatic alcohol" that can be used as the component (A2) in the present invention may be linear or branched, but is preferably linear. 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 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 monovalent to trivalent, more preferably monovalent or trivalent. Examples of aliphatic alcohols that can be used as 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, glycerin, trimethylolpropane, and the like. Of these, hexanol, heptanol, octanol, and glycerin are preferred, and hexanol, octanol, and glycerin are more preferred.
[0115] 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, a substance that generates at least one of these compounds upon heating can also be used as the component (A2).
[0116] The substance that can be used as component (A2) 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, substances that generate an aliphatic aldehyde having 3 to 14 carbon atoms upon heating include fats and oils, fatty acids (including saturated fatty acids and unsaturated fatty acids), ketones, lactones, etc., and fats and oils are preferred because they provide clear effects and have good flavor and quality.
[0117] In the present invention, "fats and oils" refers to substances whose main component is acylglycerol (triglyceride, diglyceride, monoglyceride, etc.). In general, substances that are fluid at room temperature are called "oils" and substances that are not fluid are called "fats", but the concept encompasses both of these. In the present invention, examples of fats and oils that can be used as component (A2) 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, perilla oil, linseed oil, olive oil, grape seed oil, and medium-chain fatty acid oil; and animal fats and oils such as lard (lard), beef tallow, chicken oil, mutton tallow, horse fat, fish oil, and whale oil. In addition, transesterified oils obtained by transesterifying the above-mentioned fats and oils, and hardened oils obtained by hydrogenating the above-mentioned fats and oils, etc. can also be used. The above-mentioned fats and oils may be refined (e.g., salad oil, etc.). These fats and oils may be used alone or in combination of two or more.
[0118] The fatty acid that can be used as component (A2) in the present invention may be either saturated or 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 fatty acids that can be used as component (A2) include lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, arachidic acid, and behenic acid, and are preferably stearic acid, oleic acid, and linoleic acid.
[0119] The ketone that can be used as the component (A2) in the present invention may be either saturated or 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 ketones 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, and 7-tridecanone, and preferably 3-octanone.
[0120] For a substance that produces 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 upon heating, the heating conditions for producing the aliphatic aldehyde, etc. are not particularly limited as long as the aliphatic aldehyde, etc. is produced, and may be appropriately set depending on the type of the substance, etc., but the heating temperature is usually 40 to 200°C, and preferably 60 to 180°C, and the heating time is usually 0.5 to 480 minutes, and preferably 1 to 360 minutes.
[0121] The component (A2) that can be used in the present invention is preferably an aliphatic aldehyde having 3 to 14 carbon atoms (e.g., an aliphatic aldehyde having 4 to 10 carbon atoms), an aromatic aldehyde having 7 to 12 carbon atoms (e.g., an aromatic aldehyde having 7 to 10 carbon atoms), an aliphatic alcohol having 3 to 12 carbon atoms (e.g., an aliphatic alcohol having 3 to 10 carbon atoms), an oil or fat, a fatty acid (e.g., a fatty acid having 3 to 14 carbon atoms), or a ketone (e.g., a ketone having 3 to 14 carbon atoms), more preferably an aliphatic aldehyde having 3 to 14 carbon atoms, Preferred are hexanal, 2-hexenal, octanal, 2-octenal, decanal, 2-decenal, 2,4-decadienal, 3-(methylthio)propanal, benzaldehyde, p-tolualdehyde, hexanol, octanol, glycerin, oils and fats (e.g., vegetable oils such as rapeseed oil, soybean oil, corn oil, olive oil, safflower oil, linseed oil, perilla oil, hydrogenated palm kernel oil, and medium-chain fatty acid oils), stearic acid, oleic acid, linoleic acid, and 3-octanone.
[0122] When an aliphatic aldehyde having 3 to 14 carbon atoms (e.g., an aliphatic aldehyde having 4 to 10 carbon atoms), an aromatic aldehyde having 7 to 12 carbon atoms (e.g., an aromatic aldehyde having 7 to 10 carbon atoms), an aliphatic alcohol having 3 to 12 carbon atoms (e.g., an aliphatic alcohol having 3 to 10 carbon atoms), a fatty acid (e.g., a fatty acid having 3 to 14 carbon atoms), or a ketone (e.g., a ketone having 3 to 14 carbon atoms) is used as the component (A2), the weight ratio of the component (A1) to the component (A2) to be heated is not particularly limited, but is preferably A1:A2=1:0.001-1000, more preferably A1:A2=1:0.01-100, and particularly preferably A1:A2=1:0.08-15. When fats and oils (e.g., vegetable fats and oils such as rapeseed oil, soybean oil, corn oil, olive oil, safflower oil, linseed oil, perilla oil, hydrogenated palm kernel oil, and medium-chain fatty acid oil) are used as component (A2), the concentration of component (A1) in the fats and oils at the time of heating is preferably 0.0008 to 12000 ppm by weight, more preferably 0.0008 to 1200 ppm by weight, even more preferably 0.08 to 120 ppm by weight, and particularly preferably 0.8 to 120 ppm by weight. In one embodiment, the concentration is preferably 0.0008 to 100000 ppm by weight, more preferably 0.0008 to 50000 ppm by weight, even more preferably 0.08 to 10000 ppm by weight, and particularly preferably 0.8 to 5000 ppm by weight.
[0123] There are no particular limitations on the method for producing the component (A2), and it can be produced by a method known per se or a method equivalent thereto, and it may be, for example, a synthetic product or an extract product, etc. Commercially available products can also be used, which is preferred for simplicity.
[0124] The method of heating component (A) is not particularly limited, and may be, for example, a method of directly heating component (A), or a method of dissolving or dispersing component (A) in a medium such as a solvent or dispersion medium and then heating the resulting solution, i.e., a method of heating component (A) in the medium. When component (A) is heated in a medium, it may be heated under stationary conditions, or may be heated while stirring as appropriate. Furthermore, component (A) may be heated in the coexistence of components other than the medium (e.g., component (B), etc.) as long as the object of the present invention is not impaired.
[0125] The heating temperature of component (A) may be adjusted as appropriate depending on the heating time, etc., but is preferably 40 to 200°C, more preferably 50 to 150°C, even more preferably 50 to 120°C, and particularly preferably 80 to 120°C, since this allows for the production of a heated component (A) that has an excellent mouth-coating feel enhancing effect.
[0126] The heating time for component (A) may be adjusted as appropriate depending on 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, since this allows for the production of a heated component (A) that has an excellent effect of enhancing the mouth-coating feel.
[0127] The component (A) may be heated under normal pressure or under increased pressure.
[0128] The heated product of component (A) used in the present invention may be obtained by heating component (A) by any method, and may be, for example, a product obtained by heating component (A) in a medium, etc. In one embodiment, when component (A) is heated in a medium, the medium used is not particularly limited, and examples thereof include lipids such as sterols, carotenoids, phospholipids, glycolipids, waxes, etc.; hydrocarbon oils (e.g., mineral oil, etc.), ethanol, polyethylene glycol, water, etc.
[0129] In the case where the heated product of component (A) used in the present invention is obtained by heating component (A) in a medium, the concentration of component (A1) in the medium at the time of heating, among the components (A) heated to obtain the heated product of component (A), is preferably 0.0008 to 12000 ppm by weight, more preferably 0.0008 to 1200 ppm by weight, even more preferably 0.08 to 120 ppm by weight, and particularly preferably 0.8 to 120 ppm by weight, since the mouth-coating feeling can be more effectively enhanced. In one embodiment, the concentration is preferably 0.0008 to 100000 ppm by weight, more preferably 0.0008 to 50000 ppm by weight, even more preferably 0.08 to 10000 ppm by weight, and particularly preferably 0.8 to 5000 ppm by weight.
[0130] After heating component (A) in a medium, the resulting heated product of component (A) may be separated from the medium and used; alternatively, for example, in cases where the medium used for heating is one that can be used as a food ingredient, the resulting heated product of component (A) may be used together with the medium without being separated from the medium.
[0131] [(B) Component] The component (B) of the present invention is at least one compound selected from the group consisting of β-caryophyllene (CAS Registry Number: 87-44-5) and β-caryophyllene analogues.
[0132] Examples of β-caryophyllene analogues that can be used as component (B) in the present invention include isocaryophyllene (CAS Registry Number: 118-65-0), β-pinene (CAS Registry Numbers: 127-91-3, 18172-67-3, etc.), sabinene (CAS Registry Number: 3387-41-5), eugenol (CAS Registry Number: 97-53-0), limonene (CAS Registry Number: 5989-27-5, etc.), linalool (CAS Registry Number: 78-70-6, etc.), linalool oxide (CAS Registry Number: 60047-17-8, etc.), p-cymene (CAS Registry Number: 99-87-6, etc.), farnesene (CAS Registry Number: Terpene hydrocarbons such as terpene hydrocarbons (CAS Registry Number: 502-61-4, 26560-14-5, etc.), myrcene (CAS Registry Number: 123-35-3, etc.), ocimene (CAS Registry Number: 13877-91-3, etc.), α-phellandrene (CAS Registry Number: 99-83-2, etc.), α-terpinene (CAS Registry Number: 99-86-5), γ-terpinene (CAS Registry Number: 99-85-4), terpinolene (CAS Registry Number: 586-62-9, etc.); phenols such as 4-allyl-2,6-dimethoxyphenol (CAS Registry Number: 6627-88-9), 4-vinylphenol (CAS Registry Number: 2628-17-3, etc.). These compounds may be used alone or in combination of two or more.The β-caryophyllene analogue 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, and is more 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, which can effectively improve the mouth-coating feeling. 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, and 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.
[0133] The method for producing the component (B) is not particularly limited, and it can be produced by a method known per se or a method similar thereto, and may be, for example, a synthetic product or an extract product, etc. Commercially available products can also be used, which is preferable from the viewpoint of simplicity.
[0134] 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 embodiments thereof are also the same.
[0135] The heating temperature of component (B) may be adjusted as appropriate depending on the heating time, etc., but is preferably 40 to 200°C, more preferably 50 to 150°C, even more preferably 50 to 120°C, and particularly preferably 80 to 120°C, since this allows for the production of a heated component (B) that has an excellent mouth-coating feel enhancing effect.
[0136] The heating time for component (B) may be adjusted as appropriate depending on 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, since this allows a heated product of component (B) to be obtained that has an excellent effect of enhancing the mouth-coating feel.
[0137] The heated product of component (B) used in the present invention may be a product of heating component (B) by any method, for example, a product obtained by heating component (B) in a medium. In one embodiment, when component (B) is heated in a medium, the medium used is not particularly limited, and examples thereof include lipids such as fats and oils, fatty acids (e.g., acetic acid, isovaleric acid, etc.), sterols, carotenoids, phospholipids, glycolipids, waxes, etc.; glycerol, aliphatic alcohols, hydrocarbon oils (e.g., mineral oil, etc.), ethanol, polyethylene glycol, water, and inorganic acids (e.g., hydrochloric acid, sulfuric acid, etc.). Component (A2) can also be used as a medium for heating component (B). Component (B) may be heated in the presence of components other than the medium (e.g., component (A), etc.) as long as the object of the present invention is not impaired.
[0138] Examples of fats and oils that can be used for heating the component (B) 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, perilla oil, linseed oil, olive oil, grape seed oil, and neutral fatty acid oil; and animal fats and oils such as lard (lard), beef tallow, chicken oil, mutton tallow, horse fat, fish oil, and whale oil. In addition, transesterified oils obtained by transesterifying the above-mentioned fats and oils, and hardened oils obtained by hydrogenating the above-mentioned fats and oils, etc. can also be used. The above-mentioned fats and oils may be refined (e.g., salad oil, etc.). These fats and oils may be used alone or in combination of two or more.
[0139] In the case where the heated product of component (B) used in the present invention is obtained by heating component (B) in a medium, 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, even more preferably 0.08 to 120 ppm by weight, and particularly preferably 0.8 to 120 ppm by weight, since the mouth-coating feeling can be more effectively enhanced. In one embodiment, the concentration is preferably 0.0008 to 100000 ppm by weight, more preferably 0.0008 to 50000 ppm by weight, even more preferably 0.08 to 10000 ppm by weight, and particularly preferably 0.8 to 5000 ppm by weight.
[0140] After heating component (B) in a medium, the resulting heated component (B) may be separated from the medium and used in the mouth-coating sensitivity enhancer of the present invention; alternatively, for example, in cases where the medium used for heating is one that can be used as a food ingredient, the resulting heated component (B) may be used together with the medium in the mouth-coating sensitivity enhancer of the present invention without being separated from the medium.
[0141] In one embodiment, the mouth-coating sensation enhancer of the present invention contains a heated product of component (A) and a heated product of component (B) as active ingredients, and the amount of component (A1) in the heated product of component (A) to obtain the heated product of component (A) is set to A1. 1 (weight), and the amount of the (B) component heated to obtain the (B) component heated product is B 1 (weight), the B 1 and A1 1 Ratio to (B 1 :A1 1 ) is preferably within the range of 1:0.00000008 to 12000000, more preferably within the range of 1:0.000008 to 1200000, still more preferably within the range of 1:0.008 to 12000, and particularly preferably within the range of 1:0.08 to 1200. 1 and B. 1 The weight units are the same.
[0142] In one embodiment, when the mouth-coating sensation enhancer of the present invention contains a heated product of component (A) and a heated product of component (B) as active ingredients, the heated product of component (A) and the heated product of component (B) may be obtained by heating component (A) and component (B) separately, or may be obtained by heating them together. That is, in this specification, "heated product of component (A) and heated product of component (B)" includes a mixture of heated product of component (A) and heated product of component (B) obtained separately, and a heated product obtained by heating component (A) and component (B) together. "Heated product of component (A) and heated product of component (B)" obtained by heating component (A) and component (B) together includes, for example, a heated product obtained by heating component (A) and component (B) in one medium.
[0143] [(C) component] The component (C) of the present invention is at least one selected from the following compound group (C). [Compound group (C)] β-Caryophyllene oxide (CAS registration number: 1139-30-6) α-Pinene oxide (CAS registration number: 72936-74-4, 19894-99-6) Limonene oxide (CAS registration number: 1195-92-2, etc.) α-Terpinenol (CAS registration number: 98-55-5) ·General formula (II):
[0144] [ka]
[0145] [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. A compound represented by ·General formula (III):
[0146] [ka]
[0147] [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. A compound represented by ·General formula (IV):
[0148] [ka]
[0149] [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. A compound represented by ·General formula (V):
[0150] [ka]
[0151] [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. A compound represented by (1S,6S,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecan-5-one (CAS Registry Number: 68263-68-3):
[0152] [ka]
[0153] (1S,6R,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecan-5-one (CAS Registry Number: 68330-80-3):
[0154] [ka]
[0155] (1R,4R,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carboxaldehyde (CAS Registry Number: 151121-36-7):
[0156] [ka]
[0157] (1R,4S,8S)-4,10,10-trimethyl-7-methylenebicyclo[6.2.0]decane-4-carboxaldehyde (CAS Registry Number: 2073828-10-9):
[0158] [ka]
[0159] (1S,2S,5R,9S)-1,4,4,8-Tetramethyl-12-oxatricyclo[7.2.1.0 2,5 ]Dodec-7-ene (CAS Registry Number: 1039439-81-0):
[0160] [ka]
[0161] (1R,2S,5R,8R,9R)-1,4,4,8-Tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ]Dodecan-9-ol (CAS Registry Number: 1040220-66-3):
[0162] [ka]
[0163] (1R,2S,5R,8R,9S)-1,4,4,8-Tetramethyl-12-oxatricyclo[6.3.1.0 2,5 ]Dodecan-9-ol (CAS Registry Number: 103189-32-8):
[0164] [ka]
[0165] ·[1R-(1α,2α,5β,8β,9α)]-4,4,8-trimethyl-tricyclo[6.3.1.0 2,5 ]Dodecane-1,9-diol (CAS Registry Number: 155485-75-9):
[0166] [ka]
[0167] (Compound represented by general formula (II)) Each group in formula (II) will be explained below.
[0168] R in 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.
[0169] R 3 and R 4The "acyl group having 1 to 18 carbon atoms" in the above may be linear or branched. The acyl group may be saturated or may 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 a formyl group, an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a valeryl group, an isovaleryl group, a pivaloyl group, a hexanoyl group, a caproyl group, a lauroyl group, a myristoyl group, a palmitoyl group, and a stearoyl group, among which a formyl group, an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, and an isovaleryl group are preferred, a formyl group, an acetyl group, and an isovaleryl group are more preferred, and an acetyl group and an isovaleryl group are particularly preferred.
[0170] R 3 and R 4 The "alkyl group having 1 to 6 carbon atoms" in the above may be linear or branched, but is preferably linear. 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 a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group, and are preferably a methyl group, an ethyl group, a propyl group, or a butyl group, more preferably a methyl group or an ethyl group, and particularly preferably a methyl group.
[0171] R in general formula (II) 3 is preferably 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, and particularly preferably a hydrogen atom, an acetyl group, an isovaleryl group, or a methyl group.
[0172] R in general formula (II) 4 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.
[0173] Preferred compounds (II) are shown below.
[0174] [Compound (IIA)] 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 represents a hydrogen atom or an acyl group having 1 to 18 carbon atoms Compound (II).
[0175] [Compound (IIB)] R 3 is a hydrogen atom, an acyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 4 carbon atoms; R 4 represents a hydrogen atom or an acyl group having 1 to 5 carbon atoms Compound (II).
[0176] [Compound (IIC)] R 3 is a hydrogen atom, an acetyl group, an isovaleryl group, or a methyl group; R 4 represents a hydrogen atom or an acetyl group. Compound (II).
[0177] Specific examples of suitable compound (II) include: Clobandiol (CAS Registry Number: 2649-64-1):
[0178] [ka]
[0179] Clobandiol-3-monoacetate (CAS Registry Number: 127156-28-9):
[0180] [ka]
[0181] Clobandiol diacetate (CAS Registry Number: 2649-68-5):
[0182] [ka]
[0183] Clobandiol-3-monoisovalerate (CAS Registry Number: 1891070-50-0):
[0184] [ka]
[0185] 2-Methoxyclobanol (CAS Registry Number: 127156-29-0):
[0186] [ka]
[0187] etc.
[0188] (Compound represented by general formula (III)) Each group in formula (III) will be explained below.
[0189] R in general formula (III) 5 represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms.
[0190] R 5The "acyl group having 1 to 6 carbon atoms" in the above may be linear or branched, but is preferably linear. The acyl group may be saturated or may 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 a formyl group, an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a valeryl group, an isovaleryl group, a pivaloyl group, and a hexanoyl group, and are preferably a formyl group, an acetyl group, a propionyl group, a butyryl group, or an isobutyryl group, more preferably a formyl group, an acetyl group, or a propionyl group, and particularly preferably an acetyl group.
[0191] R 5 The "alkyl group having 1 to 6 carbon atoms" in the above may be linear or branched, but is preferably linear. 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 a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group, and are preferably a methyl group, an ethyl group, a propyl group, or a butyl group, more preferably a methyl group or an ethyl group, and particularly preferably a methyl group.
[0192] R in general formula (III) 5 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.
[0193] The wavy line in formula (III) means that the compound is a mixture of either one or both of cis- and trans-isomers.
[0194] Specific examples of suitable compounds (III) include: Caryophyllenol II (CAS Registry Number: 32214-89-4):
[0195] [ka]
[0196] Caryophyllenol I (CAS Registry Number: 32214-88-3):
[0197] [ka]
[0198] (1R,3Z,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol (CAS Registry Number: 19431-76-6):
[0199] [ka]
[0200] (1R,3Z,5S,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol (CAS Registry Number: 19431-77-7):
[0201] [ka]
[0202] (1R,3EZ,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol-5-acetate
[0203] [ka]
[0204] etc.
[0205] (Compound represented by general formula (IV)) Each group in formula (IV) will be explained below.
[0206] R in general formula (IV)6 represents a hydrogen atom, an acyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms.
[0207] R 6 The "acyl group having 1 to 6 carbon atoms" in the above may be linear or branched, but is preferably linear. The acyl group may be saturated or may 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 a formyl group, an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a valeryl group, an isovaleryl group, a pivaloyl group, and a hexanoyl group, and are preferably a formyl group, an acetyl group, a propionyl group, a butyryl group, or an isobutyryl group, more preferably a formyl group, an acetyl group, or a propionyl group, and particularly preferably an acetyl group.
[0208] R 6 The "alkyl group having 1 to 6 carbon atoms" in the above may be linear or branched, but is preferably linear. 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 a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group, and are preferably a methyl group, an ethyl group, a propyl group, or a butyl group, more preferably a methyl group or an ethyl group, and particularly preferably a methyl group.
[0209] R in general formula (IV) 6 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.
[0210] Specific examples of suitable compounds (IV) include: Caryophylladienol II (CAS Registry Number: 19431-79-9):
[0211] [ka]
[0212] Caryophylladienol I (CAS Registry Number: 19431-80-2):
[0213] [ka]
[0214] (1S,5R,9R)-10,10-Dimethyl-2,6-bismethylene-bicyclo[7.2.0]undecane-5-ol acetate (CAS Registry Number: 99805-59-1):
[0215] [ka]
[0216] (1S,5S,9R)-10,10-Dimethyl-2,6-bismethylene-bicyclo[7.2.0]undecane-5-ol acetate (CAS Registry Number: 99881-55-7):
[0217] [ka]
[0218] etc.
[0219] (Compound represented by general formula (V)) Each group in formula (V) will be explained below.
[0220] R in 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.
[0221] R 7 and R 8The "acyl group having 1 to 6 carbon atoms" in the above may be linear or branched, but is preferably linear. The acyl group may be saturated or may 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 a formyl group, an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a valeryl group, an isovaleryl group, a pivaloyl group, and a hexanoyl group, and are preferably a formyl group, an acetyl group, a propionyl group, a butyryl group, or an isobutyryl group, more preferably a formyl group, an acetyl group, or a propionyl group, and particularly preferably an acetyl group.
[0222] R 7 and R 8 The "alkyl group having 1 to 6 carbon atoms" in the above may be linear or branched, but is preferably linear. 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 a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group, and are preferably a methyl group, an ethyl group, a propyl group, or a butyl group, more preferably a methyl group or an ethyl group, and particularly preferably a methyl group.
[0223] R in general formula (V) 7 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.
[0224] R in general formula (V) 8 is preferably a hydrogen atom.
[0225] A preferred compound (V) is shown below.
[0226] [Compound (VA)] R 7 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R 8indicates a hydrogen atom Compound (V).
[0227] [Compound (VB)] R 7 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 8 indicates a hydrogen atom Compound (V).
[0228] [Compound (VC)] R 7 is a hydrogen atom or a methyl group; R 8 indicates a hydrogen atom Compound (V).
[0229] Specific examples of suitable compounds (V) include: (1R,4R,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undecane-4,5-diol (CAS Registry Number: 187935-72-4):
[0230] [ka]
[0231] (1R,4S,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undecane-4,5-diol (CAS Registry Number: 151029-00-4):
[0232] [ka]
[0233] (1S,5R,6R,9R)-6-Methoxy-6,10,10-trimethyl-2-methylene-bicyclo[7.2.0]undecane-5-ol (CAS Registry Number: 178939-28-1):
[0234] [ka]
[0235] (1S,5R,6S,9R)-6-Methoxy-6,10,10-trimethyl-2-methylene-bicyclo[7.2.0]undecane-5-ol (CAS Registry Number: 187935-73-5):
[0236] [ka]
[0237] etc.
[0238] 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 clobandiol, clobandiol-3-monoacetate, clobandiol diacetate and clobandiol-3-monoisovalerate.
[0239] The method for producing the component (C) is not particularly limited, and the component can be produced by a method known per se or a method similar thereto, and may be, for example, a synthetic product or an extract product. Specifically, the component (C) can be produced by the method described in the Examples below. In addition, a commercially available product can be used as the component (C), which is preferable because of its simplicity.
[0240] When the mouse-coating sensitivity enhancer of the present invention contains component (C) as one embodiment, the content of component (C) in the mouse-coating sensitivity 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 mouse-coating sensitivity enhancer of the present invention. 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 mouse-coating sensitivity enhancer of the present invention.
[0241] The form of the mouth-coating sensation enhancer of the present invention is not particularly limited, and examples thereof include solid forms (including powders, granules, etc.), liquid forms (including slurries, etc.), gels, pastes, and the like.
[0242] In one embodiment, the mouth-coating sensation enhancer of the present invention may consist only of a heated product of component (A) (and the medium used for heating component (A)), or only of a heated product of component (B) (and the medium used for heating component (B)), or may consist only of a heated product of component (A) (and the medium used for heating component (A)) and a heated product of component (B) (and the medium used for heating component (B)). In addition to these heated products, the mouth-coating sensation enhancer may further contain a conventional base depending on the form, etc. of the mouth-coating sensation enhancer of the present invention. In another embodiment, the mouse-coating sensation enhancer of the present invention may consist only of component (C). In addition, it may further contain a conventional base depending on the form, etc., of the mouse-coating sensation enhancer of the present invention.
[0243] When the mouth-coating sensation enhancer of the present invention is in the form of a liquid, examples of the base include water, ethanol, glycerin, propylene glycol, etc. When the mouth-coating sensation enhancer of the present invention is in the form of a solid, 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, as well as yeast cells and various powdered extracts.
[0244] The mouth-coating sensation enhancer of the present invention may further contain, in addition to the heated component (A) and / or the heated component (B), or the component (C), for example, excipients, pH adjusters, antioxidants, thickening stabilizers, sweeteners (e.g., sugars, etc.), acidulants, spices, colorants, etc., as long as the object of the present invention is not impaired.
[0245] The mouse-coating feel enhancer of the present invention can be produced by a method known per se. The mouse-coating feel enhancer of the present invention may be subjected to, for example, a concentration treatment, a drying treatment, a decolorization treatment, etc., either alone or in combination.
[0246] The heated product of component (A) and / or heated product of component (B) that may be contained in the mouse-coating sensitivity enhancer of the present invention is a substance obtained by heating component (A) and / or component (B) as described above, and therefore the method for producing the mouse-coating sensitivity enhancer of the present invention may include heating component (A) and / or component (B). In the method for producing the mouse-coating sensitivity enhancer of the present invention, the method for heating component (A) and component (B) is the same as the above-mentioned method for heating component (A) and component (B), and the preferred embodiments are also the same. Furthermore, the respective heating temperatures and heating times may be set in the same manner as described above.
[0247] In one embodiment of the method for producing the mouth-coating feel enhancer of the present invention, the amount of the component (A1) in the component (A) to be heated is set to A1 4 (weight), and the amount of component (B) to be heated is B 4 (weight), the B 4 and A1 4 Ratio to (B 4 :A1 4 ) is the above B1 and A1 1 Ratio to (B 1 :A1 1 ) may be set within the same range, and the preferred range is also the same.
[0248] When the method for producing the mouth-coating sensation enhancer of the present invention includes heating the components (A) and (B), the components (A) and (B) may be heated separately or together. An example of a method for heating the components (A) and (B) together is a method in which both the components (A) and (B) are dissolved or dispersed in a medium and then heated.
[0249] The mouth-coating feel enhancer of the present invention can be used by being added to food. By adding the mouth-coating feel enhancer of the present invention to food, the mouth-coating feel of the food can be enhanced. In the present invention, the term "mouth-coating feeling" refers to the feeling that the oral cavity is covered with a thin film, the feeling that the oral cavity is covered with an oil or oil-like film, the smooth feeling felt in the oral cavity, and the thick oil-like feeling (thickness) that spreads throughout the oral cavity, which are prominently felt when oil or fat, or a solution or food containing oil or fat, is taken into the oral cavity. "Enhanced" mouth-coating feeling refers to enhancement of at least one of the above sensations. The presence or absence and the degree of mouth-coating feeling can be evaluated by sensory evaluation by a specialist panel. In the present invention, the term "food" is a concept that broadly includes anything that can be orally ingested, and includes, for example, beverages, seasonings, food additives, and the like.
[0250] The food to which the mouth-coating sensation enhancer of the present invention can be added may be provided (sold, distributed) in a state suitable for eating from the beginning, or may be provided in a state that requires a specific treatment or cooking to become suitable for eating. For example, the food to which the mouth-coating sensation enhancer of the present invention can be added may be provided as a concentrate that requires dilution with water or the like to become suitable for eating.
[0251] Foods to which the mouth-coating sensation enhancer of the present invention can be added are not particularly limited as long as they are desired to have a mouth-coating sensation, and examples thereof include fats and oils (e.g., vegetable fats and oils, animal fats and oils, etc.), mayonnaise, soup, dressing, fried curry food, snacks, chocolate, cookies, bread, fats and oils-containing milk and dairy products (e.g., raw milk, milk, low-fat milk, cream, butter, margarine, fat spreads, cheese, yogurt, etc.), fats and oils-containing beverages, fats and oils-containing noodles (e.g., fried noodles, etc.); fats and oils-free foods such as non-oil dressings, fats and oils-free milk and dairy products (fat-free milk, skim milk powder, fat-free yogurt), fats and oils-free beverages (e.g., coffee beverages, etc.), fats and oils-free noodles (e.g., non-fried noodles, raw noodles, pasta, noodle strips). Here, the fats and oils-containing foods may contain only fats and oils, that is, the fats and oils-containing foods may be fats and oils themselves.
[0252] Since the mouth-coating sensation enhancer of the present invention can significantly enhance the mouth-coating sensation felt when fats and oils are held in the oral cavity, it is preferably used by adding it to fat-and-oil-containing foods, that is, the mouth-coating sensation enhancer of the present invention is preferably for use in fat-and-oil-containing foods.
[0253] The fats and oils contained in the fat-containing food in which the mouth-coating sensation enhancer of the present invention can be used 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, perilla oil, linseed oil, olive oil, grape seed oil, and neutral fatty acid oil; and animal fats and oils such as lard (lard), beef tallow, chicken oil, mutton tallow, horse fat, fish oil, whale oil, and milk fat. In addition, transesterified oils obtained by transesterifying the above-mentioned fats and oils, and hardened oils obtained by hydrogenating the above-mentioned fats and oils, etc. can also be used. The above-mentioned fats and oils may be refined (e.g., salad oil, etc.). These fats and oils may be used alone or in combination of two or more.
[0254] The content of oil and fat in the oil-containing food in which the mouth-coating sensation enhancer of the present invention can be used is not particularly limited, but since the effect can be more clearly exhibited, it is preferably 0.1 to 100% by weight, and more preferably 0.5 to 100% by weight.
[0255] The method and conditions for adding the mouse-coating sensitivity enhancer of the present invention to food are not particularly limited, and can be appropriately set depending on the form of the mouse-coating sensitivity enhancer of the present invention and the type of food, etc. The timing for adding the mouse-coating sensitivity enhancer of the present invention to food is not particularly limited, and it can be added at any time, for example, during the production of the food, after the food is completed (just before eating the food, while eating the food, etc.), etc. The mouse-coating sensitivity enhancer of the present invention may also be added to raw materials before the food is produced.
[0256] In one embodiment, when the mouse-coating sensitivity enhancer of the present invention contains component (C), the mouse-coating sensitivity enhancer of the present invention can be added to food so that the amount of 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 mouse-coating sensitivity enhancer of the present invention can be added to food so that the amount of 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.
[0257] <Method to enhance mouth coating sensation> The present invention also provides a method for enhancing mouth-coating sensation, which comprises adding a heated product of component (A) and / or a heated product of component (B). The present invention also provides a method for enhancing mouth-coating sensation, which comprises adding component (C). In this specification, these methods may be collectively referred to as the "method for enhancing mouth-coating feeling of the present invention."
[0258] The heated product of component (A) and / or the heated product of component (B) that can be used in the method for enhancing a mouth-coating sensation of the present invention is the same as the heated product of component (A) and / or the heated product of component (B) that can be contained in the mouth-coating sensation enhancer of the present invention, and the preferred embodiments are also the same. In addition, they can be produced in the same manner as the method described above.
[0259] The component (C) that can be used in the method for enhancing mouse-coating sensation of the present invention is the same as the component (C) that can be contained in the mouse-coating sensation enhancer of the present invention, and the preferred embodiments are also the same. In addition, they can be produced in the same manner as the method described above.
[0260] In one embodiment of the method for enhancing mouth-coating sensation of the present invention, when the method includes adding a heated product of component (A) and a heated product of component (B), the amount of component (A1) in the component (A) heated to obtain the heated product is 2 (weight), and the amount of the heated component (B) to obtain the heated product is B 2 (weight), the B 2 and A1 2 Ratio to (B 2 :A1 2 ) is the above B 1 and A1 1 Ratio to (B 1 :A1 1 ) may be set within the same range, and the preferred range is also the same.
[0261] The heated product of component (A) and / or the heated product of component (B) that can be used in the method for enhancing mouth-coating sensation of the present invention are substances obtained by heating component (A) and / or component (B), respectively, as described above. Therefore, the method for enhancing mouth-coating sensation of the present invention can comprise heating component (A) and / or component (B) and adding the obtained heated product of component (A) and / or heated product of component (B).
[0262] According to the method for enhancing a mouth-coating feeling of the present invention, the mouth-coating feeling of food can be enhanced. Examples of foods that can enhance the mouth-coating feeling by the method for enhancing a mouth-coating feeling of the present invention include the same foods as those exemplified as foods to which the mouth-coating feeling enhancer of the present invention can be added, and the same is also true for preferred foods.
[0263] The method for enhancing a mouth-coating feeling of the present invention can significantly enhance the mouth-coating feeling felt when fats and oils are held in the oral cavity, and is therefore preferably a method for enhancing a mouth-coating feeling of fats and oils-containing foods.
[0264] In the method for enhancing mouth-coating sensation of the present invention, the method and conditions for adding the heated (A) component and / or the heated (B) component are not particularly limited and can be appropriately set depending on the type of food, etc. The timing for adding the heated (A) component and / or the heated (B) component 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 eating the food, while eating the food, etc.), etc. The heated (A) component and / or the heated (B) component can also be added to the raw materials before the food is produced.
[0265] In the method for enhancing mouth-coating sensation of the present invention, the method and conditions for adding component (C) are not particularly limited and can be appropriately set depending on the type of food, etc. The timing for adding 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 eating the food, while eating the food, etc.), etc. Component (C) may also be added to the raw materials before the food is produced.
[0266] In the method for enhancing mouth-coating sensation of the present invention, the addition of component (C) may be carried out so that the amount of component (C) added to the food is similar to the amount of component (C) added to the food when the mouth-coating sensation enhancer of the present invention is added to the food (described above).
[0267] <Food manufacturing method> The present invention also provides a method for producing a food product, the method comprising adding a heated product of component (A) and / or a heated product of component (B). The present invention also provides a method for producing a food product, which comprises adding component (C). In this specification, these production methods may be collectively referred to as the "production method of the present invention."
[0268] The heated product of component (A) and / or the heated product of 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 the heated product of component (B) that can be contained in the mouth-coating sensation enhancer of the present invention, and the preferred embodiments are also the same. In addition, they can be produced in the same manner as the above-mentioned method.
[0269] 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 mouth-coating sensation enhancer of the present invention, and the preferred embodiments are also the same. In addition, the production of these components can be carried out in the same manner as the above-mentioned method.
[0270] When the production method of the present invention includes adding a heated product of the component (A) and a heated product of the component (B), the amount of the component (A1) in the component (A) heated to obtain the heated product is 3 (weight), and the amount of the heated component (B) to obtain the heated product is B 3 (weight), the B 3 and A1 3 Ratio to (B 3 :A1 3 ) is the above B 1 and A1 1 Ratio to (B 1 :A1 1 ) may be set within the same range, and the preferred range is also the same.
[0271] As described above, the heated product of component (A) and / or the heated product of component (B) that can be used in the production method of the present invention are substances obtained by heating component (A) and / or component (B), respectively, and therefore the production method of the present invention may include heating component (A) and / or component (B). Furthermore, the production method of the present invention may include adding the obtained heated product of component (A) and / or heated product of component (B).
[0272] In the production method of the present invention, the method and conditions for adding the heated component (A) and / or the heated component (B) are not particularly limited and can be appropriately set depending on the type of food to be produced, etc. The timing for adding the heated component (A) and / or the heated component (B) is not particularly limited and can be added at any time from the start to the completion of food production. In addition, the heated component (A) and / or the heated component (B) can be added to raw materials before the food is produced.
[0273] In the manufacturing method of the present invention, the method and conditions for adding component (C) are not particularly limited and can be appropriately set depending on the type of food, etc. The timing of adding component (C) is not particularly limited and can be added at any time from the start to the completion of food manufacturing. Also, component (C) can be added to raw materials before the food is manufactured.
[0274] In the manufacturing method of the present invention, the addition of component (C) can be carried out so that the amount of component (C) added to the food is similar to the amount of component (C) added to the food when the mouth-coating sensation enhancer of the present invention is added to the food (described above).
[0275] The production method of the present invention may include, in addition to adding the heated component (A) and / or the heated component (B), or the component (C), appropriate processing steps and cooking steps conventionally used in food production depending on the type of food to be produced, etc.
[0276] 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 a 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 a component (C) and having an enhanced mouth-coating feel 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 mouth-coating feel enhancer of the present invention can be added, and the same is also true for preferred foods.
[0277] The production method of the present invention is preferably a method for producing an oil-containing food, and more preferably a method for producing an oil-containing food having an enhanced mouth-coating feeling.
[0278] <Coffee roast enhancer> One aspect of the coffee roasting sensation enhancer of the present invention is characterized in that it contains a heated product of component (A) and / or component (B) as an active ingredient. The heated product of component (A) and / or the heated product of component (B) that can be contained in the coffee roasting sensation enhancer of the present invention is the same as the heated product of component (A) and / or the heated product of component (B) that can be contained in the mouth-coating sensation enhancer of the present invention, and the preferred embodiments are also the same. In addition, they can be produced in the same manner as described above.
[0279] In another embodiment, the coffee roasting sensation enhancer of the present invention is characterized in that it contains component (C) as an active ingredient. The component (C) that can be contained in the coffee roasting sensation enhancer of the present invention is the same as the component (C) that can be contained in the mouth-coating sensation enhancer of the present invention, and the preferred embodiments are also the same. In addition, the preparation thereof can be carried out in the same manner as described above.
[0280] When the coffee roast sensation enhancer of the present invention contains a heated product of component (A), the heating temperature of component (A) is, since the coffee roast sensation can be effectively enhanced, preferably 80 to 150° C., more preferably 80 to 130° C., and particularly preferably 85 to 120° C. In this case, the heating time of component (A) is, since the coffee roast sensation can be effectively enhanced, preferably 5 to 150 minutes, more preferably 10 to 120 minutes, and particularly preferably 20 to 100 minutes.
[0281] When the coffee roast sensation enhancer of the present invention contains a heated product of component (B), the heating temperature of component (B) is, since the coffee roast sensation can be effectively enhanced, preferably 70 to 150° C., more preferably 80 to 130° C., and particularly preferably 85 to 120° C. In this case, the heating time of component (B) is, since the coffee roast sensation can be effectively enhanced, preferably 5 to 150 minutes, more preferably 10 to 120 minutes, and particularly preferably 20 to 100 minutes.
[0282] The form of the coffee roast feeling enhancer of the present invention, the amount of the heated component (A) and / or the heated component (B) that may be contained in the coffee roast feeling enhancer of the present invention, and the base that may be contained in the coffee roast feeling enhancer of the present invention are all the same as those of the mouth-coating feeling enhancer of the present invention.
[0283] Furthermore, when the coffee roasting sensation enhancer of the present invention contains component (C), the content of component (C) and the amount of component (C) added to the food are both the same as those of the mouth-coating sensation enhancer of the present invention.
[0284] In one embodiment, the coffee roasting sensation enhancer of the present invention contains a heated product of component (A) and a heated product of component (B), and the amount of component (A1) in the heated product of component (A) to obtain the heated product of component (A) is set to A1. 1 (weight), and the amount of the (B) component heated to obtain the (B) component heated product is B 1 (weight), the B 1 and A1 1 Ratio to (B 1 :A11 ) 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, because this can effectively enhance the roasted coffee flavor. 1 and B. 1 The weight units are the same.
[0285] The coffee roasting sensation enhancer of the present invention can be produced in the same manner as in the production of the mouth-coating sensation enhancer of the present invention, and the preferred embodiments thereof are also the same.
[0286] In one embodiment of the method for producing a coffee roasting sensation enhancer of the present invention, the amount of component (A1) in the component (A) to be heated is set to A1 4 (weight), and the amount of component (B) to be heated is B 4 (weight), the B 4 and A1 4 Ratio to (B 4 :A1 4 ) 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, because this can effectively enhance the roasted coffee flavor. 4 and B. 4 The weight units are the same.
[0287] The coffee roast sensation enhancer of the present invention can be added to a coffee beverage for use. By adding the coffee roast sensation enhancer of the present invention to a coffee beverage, the roast sensation of the coffee beverage can be enhanced. In the present invention, the term "roasted coffee flavor" refers to a coffee-like fragrant aroma and bitterness. "Enhancement" of the roasted coffee flavor refers to enhancement of at least one of the coffee-like fragrant aroma and bitterness. The presence or absence and the degree of the roasted coffee flavor can be evaluated by sensory evaluation by a specialist panel. In the present invention, the term "coffee beverage" refers to a beverage containing a component derived from coffee beans as one of its ingredients. Examples of the component derived from coffee beans include a liquid (coffee extract) extracted with water or hot water from ground roasted coffee beans, instant coffee powder obtained by subjecting a coffee extract to a drying process or the like, commercially available instant coffee powder, and commercially available coffee portions (concentrated coffee liquid). Coffee beverages may contain components other than the components derived from coffee beans (e.g., milk, dairy products, sweeteners, etc.).
[0288] The coffee roasting sensation enhancer of the present invention can also enhance the milky sensation. In the present invention, the term "milky sensation" refers to a milk-like aroma and sweetness. "Enhancement" of the milky sensation refers to enhancement of at least one of the milky aroma and sweetness. The presence or absence and the degree of the milky sensation can be evaluated by sensory evaluation by a specialist panel.
[0289] The method and conditions for adding the coffee roast sensation enhancer of the present invention to a coffee beverage are not particularly limited, and can be appropriately set depending on the form of the coffee roast sensation of the present invention, etc. The timing for adding the coffee roast sensation enhancer of the present invention to a coffee beverage is not particularly limited, and the agent may 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, while drinking the coffee beverage, etc.), etc.
[0290] <How to enhance the roasted taste of coffee> The present invention also provides a method for enhancing the roast flavor of coffee, comprising adding a heated product of component (A) and / or a heated product of component (B). The present invention also provides a method for enhancing coffee roast flavor, which comprises adding component (C). In this specification, these methods may be collectively referred to as the "method for enhancing coffee roast taste of the present invention."
[0291] The heated product of component (A) and / or the heated product of component (B) that can be used in the method for enhancing coffee roast feel of the present invention is the same as the above-mentioned heated product of component (A) and / or the heated product of component (B) that can be contained in the mouth-coating feel enhancer or coffee roast feel enhancer of the present invention, and the preferred embodiments are also the same. In addition, they can be produced in the same manner as the above-mentioned method.
[0292] The component (C) that can be used in the method for enhancing coffee roast feeling of the present invention is the same as the component (C) that can be contained in the mouth-coating feel enhancer or coffee roast feeling enhancer of the present invention, and the preferred embodiments are also the same. In addition, the production thereof can be carried out in the same manner as the above-mentioned method.
[0293] The method for enhancing coffee roast feeling of the present invention may be carried out in the same manner as the method for enhancing mouthfulness of the present invention, unless otherwise specified. The method for enhancing coffee roast feeling of the present invention may include, like the method for enhancing mouthfulness of the present invention, heating component (A) and / or component (B) and adding the obtained heated product of component (A) and / or heated product of component (B).
[0294] In one embodiment of the method for enhancing the coffee roasting sensation of the present invention, when the method includes adding a heated product of component (A) and a heated product of component (B), the amount of component (A1) in the component (A) heated to obtain the heated product is 2 (weight), and the amount of the heated component (B) to obtain the heated product is B 2 (weight), the B 2 and A1 2 Ratio to (B 2 :A1 2 ) 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, because this can effectively enhance the roasted coffee flavor. 2 and B. 2 The weight units are the same.
[0295] According to the method for enhancing the roast taste of coffee of the present invention, it is possible to enhance the roast taste of coffee in a coffee beverage and also to enhance the milky taste of the coffee beverage.
[0296] In the method for enhancing the coffee roast taste of the present invention, the timing of adding the heated product of component (A) and / or the heated product of component (B) to the coffee beverage is not particularly limited and may 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, while drinking the food, etc.), etc. The heated product of component (A) and / or the heated product of component (B) may also be added to the raw materials before the production of the coffee beverage.
[0297] <How to make coffee drinks> The present invention also provides a method for producing a coffee beverage, which comprises adding a heated product of component (A) and / or a heated product of component (B). The present invention also provides a method for producing a coffee beverage, which comprises adding component (C). In this specification, these production methods may be collectively referred to as "the method for producing a coffee beverage of the present invention."
[0298] The heated product of component (A) and / or the heated product of component (B) that can be used in the method for producing a coffee beverage of the present invention is the same as the above-mentioned heated product of component (A) and / or heated product of component (B) that can be contained in the mouth-coating feel enhancer or coffee roasting feel enhancer of the present invention, and the preferred embodiments are also the same. In addition, they can be produced in the same manner as the above-mentioned method.
[0299] The component (C) that can be used in the method for producing a coffee beverage of the present invention is the same as the component (C) that can be contained in the mouth-coating feel enhancer or coffee roasting feel enhancer of the present invention, and the preferred embodiments are also the same. In addition, the production thereof can be carried out in the same manner as described above.
[0300] The method for producing a coffee beverage of the present invention may be carried out in the same manner as the production method of the present invention, unless otherwise specified. The method for producing a coffee beverage of the present invention may include, like the production method of the present invention, heating component (A) and / or component (B) and adding the obtained heated product of component (A) and / or heated product of component (B).
[0301] When the method for producing a coffee beverage of the present invention includes adding a heated product of component (A) and a heated product of component (B), the amount of component (A1) in the component (A) heated to obtain the heated product is 3 (weight), and the amount of the heated component (B) to obtain the heated product is B 3 (weight), the B 3 and A1 3 Ratio to (B 3 :A1 3 ) 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, because this can effectively enhance the roasted coffee flavor. 3 and B. 3 The weight units are the same.
[0302] According to the method for producing a coffee beverage of the present invention, a coffee beverage can be produced that contains a heated product of component (A) and / or a heated product of component (B), or component (C), preferably a coffee beverage can be produced that contains a heated product of component (A) and / or a heated product of component (B), or component (C) and has an enhanced roasted coffee flavor, and more preferably a coffee beverage can be produced that contains a heated product of component (A) and / or a heated product of component (B), or component (C) and has an enhanced roasted coffee flavor and milk flavor.
[0303] The present invention will be described in more detail in the following examples, but the present invention is not limited to these examples. In this specification, "%" and "ppm" mean "% by weight" and "ppm by weight" unless otherwise specified. EXAMPLES
[0304] (Test Example 1) <Positive and negative controls> As a positive control, a regular commercially available mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Mayonnaise", oil content: 73%) was used to which 1 wt% unheated safflower oil (manufactured by Ajinomoto Co., Inc.) was added. The negative control was a commercially available mayonnaise with a lower fat content than the positive control mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Kokuma (registered trademark) 65% calorie reduction", fat content: 23%) to which 1% by weight of unheated safflower oil (manufactured by Ajinomoto Co., Inc.) was added. <Evaluation Samples 1-1~1-4> β-caryophyllene, furfuryl alcohol, or furfural (all manufactured by Sigma-Aldrich) was added to safflower oil (manufactured by Ajinomoto Co., Inc.) and dissolved at the concentrations shown in Table 1 below (β-caryophyllene: 10 ppm in safflower oil, furfuryl alcohol: 100 ppm in safflower oil, furfural: 1 to 100 ppm in safflower oil), and the safflower oil was heated at 100° C. for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.). Each heated safflower oil was added at 1% by weight to the commercially available mayonnaise used in the preparation of the negative control instead of adding unheated safflower oil, and the resulting mayonnaises were designated as evaluation samples 1-1 to 1-4. <Sensory evaluation> The mouth-coating feel was evaluated by a three-member expert panel who tasted each of the positive control, negative control, and evaluation sample mayonnaises and scored the evaluation samples in increments of 0.1 points from 0.0 to 5.0 points, with the positive control being assigned a score of "5.0 points" and the negative control being assigned a score of "0.0 points." The results are shown in Table 1 below.
[0305] [Table 1]
[0306] As is clear from the results in Table 1, the mouth-coating feel of each evaluation sample was effectively enhanced by the heated product of component (A) and / or the heated product of component (B) (specifically, the heated product of β-caryophyllene, furfuryl alcohol, and safflower oil, and the heated product of β-caryophyllene, furfural, and safflower oil).
[0307] (Test Example 2) <Positive and negative controls> As a positive control, a regular commercially available mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Mayonnaise", oil content: 73%) was used to which 1 wt% unheated mineral oil (manufactured by Kaneda Co., Ltd.) was added. The negative control was a commercially available mayonnaise with a lower fat content than the positive control mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Kokuma (registered trademark) 65% calorie reduction", fat content: 23%) to which 1% by weight of unheated mineral oil (manufactured by Kaneda Co., Ltd.) was added. <Evaluation Samples 2-1~2-4> 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 the mineral oil was heated at 100°C for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.). Each heated mineral oil was added at 1% by weight to the commercially available mayonnaise used in the preparation of the negative control, instead of adding unheated mineral oil, and the resulting mayonnaises were designated as evaluation samples 2-1 to 2-4. <Sensory evaluation> The mouth-coating sensation was evaluated in the same manner as in Test Example 1. The results are shown in Table 2 below.
[0308] [Table 2]
[0309] As is clear from the results in Table 2, the mouth-coating feel of each evaluation sample was effectively enhanced by the heated products of component (A) and / or the heated products of component (B) (specifically, the heated products of β-caryophyllene, furfuryl alcohol, and 2-hexenal, and the heated products of β-caryophyllene, furfural, and 2-hexenal).
[0310] (Test Example 3) <Positive and negative controls> For the positive control, a regular commercially available mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Mayonnaise", oil content: 73%) was used to which 0.001 to 1 wt% of unheated safflower oil (manufactured by Ajinomoto Co., Inc.) was added. The negative control was a commercially available mayonnaise with a lower fat content than the positive control mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Kokuma (registered trademark) 65% calorie reduction", fat content: 23%) to which 0.001 to 1 weight % of unheated safflower oil (manufactured by Ajinomoto Co., Inc.) was added. <Evaluation Samples 3-1~3-11> β-caryophyllene and furfural (both manufactured by Sigma-Aldrich) were added to safflower oil (manufactured by Ajinomoto Co., Inc.) and dissolved at the concentrations shown in Table 3 below (β-caryophyllene: 10 to 10,000 ppm in safflower oil, furfural: 10 to 10,000 ppm in safflower oil), and the safflower oil was heated at 100° C. for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.). Each heated safflower oil was added at 0.001 to 1% by weight to the commercially available mayonnaise used in the preparation of the negative control, instead of adding unheated safflower oil, and the resulting mayonnaises were designated as evaluation samples 3-1 to 3-11. <Sensory evaluation> The mouth-coating sensation was evaluated in the same manner as in Test Example 1. The results are shown in Table 3 below.
[0311] [Table 3]
[0312] As is clear from the results in Table 3, the mouth-coating feel of each evaluation sample was effectively enhanced by the heated product of component (A) and / or the heated product of component (B) (specifically, the heated products of β-caryophyllene, furfural and safflower oil).
[0313] (Test Example 4) <Positive and negative controls> For the positive control, a regular commercially available mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Mayonnaise", oil content: 73%) was used to which 0.001 to 1 wt% of unheated mineral oil (manufactured by Kaneda Co., Ltd.) was added. The negative control was a commercially available mayonnaise with a lower fat content than the positive control mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Kokuma (registered trademark) 65% calorie reduction", fat content: 23%) to which 0.001 to 1% by weight of unheated mineral oil (manufactured by Kaneda Co., Ltd.) was added. <Evaluation Samples 4-1~4-11> β-caryophyllene, furfural, and 2-hexenal (all manufactured by Sigma-Aldrich Co., Ltd.) were added to mineral oil (manufactured by Kaneda Co., Ltd.) and dissolved at the concentrations shown in Table 4 below (β-caryophyllene: 10 to 10,000 ppm relative to mineral oil, furfural: 10 to 10,000 ppm relative to mineral oil, 2-hexenal: 10 to 10,000 ppm relative to mineral oil), and the mineral oil was heated at 100°C for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.). Each heated mineral oil was added at 0.001 to 1% by weight to the commercially available mayonnaise used in the preparation of the negative control above, instead of adding unheated mineral oil, and the obtained mayonnaises were used as evaluation samples 4-1 to 4-11. <Sensory evaluation> The mouth-coating sensation was evaluated in the same manner as in Test Example 1. The results are shown in Table 4 below.
[0314] [Table 4]
[0315] As is clear from the results in Table 4, the mouth-coating feel of each evaluation sample was effectively enhanced by the heated product of component (A) and / or the heated product of component (B) (specifically, the heated products of β-caryophyllene, furfural and 2-hexenal).
[0316] (Test Example 5-1) <Positive and negative controls> The positive control was a regular commercially available mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Mayonnaise", oil content: 73%) to which 0.2 wt% unheated safflower oil (manufactured by Ajinomoto Co., Inc.) was added. The negative control was a commercially available mayonnaise with a lower fat content than the positive control mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Kokuma (registered trademark) 65% calorie reduction", fat content: 23%) to which 0.2 wt% unheated safflower oil (manufactured by Ajinomoto Co., Inc.) was added.
[0317] <Evaluation Samples 5-1~5-8> β-caryophyllene and furfural (both manufactured by Sigma-Aldrich) were added to safflower oil (manufactured by Ajinomoto Co., Inc.) and dissolved at the concentrations shown in Table 5 below (β-caryophyllene: 100 ppm in safflower oil, furfural: 100 ppm in safflower oil), and the safflower oil was heated at 100° C. for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.) The heated safflower oil was added at 0.1% by weight 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., Inc.) was further added to obtain a mayonnaise, which was designated as evaluation sample 5-1.
[0318] Furfural (Sigma-Aldrich) was added to safflower oil (Ajinomoto Co., Inc.) and dissolved at the concentration shown in Table 5 below (100 ppm relative to the safflower oil), and the safflower oil was then heated at 100°C for 30 minutes using a water bath (Tokyo Rikakikai Co., Ltd.) The heated safflower oil was added at 0.1% by weight to the commercially available mayonnaise used in the preparation of the negative control, and 0.1% by weight of unheated safflower oil (Ajinomoto Co., Inc.) was further added to obtain mayonnaise, which was designated as evaluation sample 5-2.
[0319] β-Caryophyllene (Sigma-Aldrich) was added to safflower oil (Ajinomoto Co., Inc.) and dissolved at the concentration shown in Table 5 below (100 ppm relative to the safflower oil), and the safflower oil was then heated at 100° C. for 30 minutes using a water bath (Tokyo Rikakikai Co., Ltd.) The heated safflower oil was added at 0.1% by weight to the commercially available mayonnaise used in the preparation of the negative control, and 0.1% by weight of unheated safflower oil (Ajinomoto Co., Inc.) was further added to obtain mayonnaise, which was designated as evaluation sample 5-3.
[0320] Safflower oil (Ajinomoto Co., Inc.) was heated at 100° C. for 30 minutes using a water bath (Tokyo Rikakikai Co., Ltd.). The heated safflower oil was added in an amount of 0.2% by weight to the commercially available mayonnaise used in the preparation of the negative control, and the resulting mayonnaise was designated as evaluation sample 5-4.
[0321] Safflower oil (Ajinomoto Co., Inc.) and furfural (Sigma-Aldrich Co., Ltd.) were each heated at 100°C for 30 minutes using a water bath (Tokyo Rikakikai Co., Ltd.), and then mixed. The amount of furfural before heating was 100 ppm relative to the safflower oil before heating. The resulting mixture was added at 0.1% by weight to the commercially available mayonnaise used in the preparation of the negative control, and 0.1% by weight of unheated safflower oil (Ajinomoto Co., Inc.) was further added to obtain mayonnaise, which was designated as evaluation sample 5-5.
[0322] Safflower oil (Ajinomoto Co., Inc.) and β-caryophyllene (Sigma-Aldrich Co., Ltd.) were each heated at 100°C for 30 minutes using a water bath (Tokyo Rikakikai Co., Ltd.), and then mixed. The amount of β-caryophyllene before heating was 100 ppm relative to the safflower oil before heating. The mixture obtained was added at 0.1% by weight to the commercially available mayonnaise used in the preparation of the negative control, and 0.1% by weight of unheated safflower oil (Ajinomoto Co., Inc.) was further added to obtain mayonnaise, which was designated as evaluation sample 5-6.
[0323] Safflower oil (Ajinomoto Co., Inc.), furfural and β-caryophyllene (all manufactured by Sigma-Aldrich Co., Ltd.) were each heated at 100°C for 30 minutes using a water bath (Tokyo Rikakikai Co., Ltd.), and then mixed. The amount of furfural and β-caryophyllene before heating was 100 ppm relative to the safflower oil before heating. The obtained mixture was added at 0.1 wt% to the commercially available mayonnaise used in the preparation of the negative control, and 0.1 wt% of unheated safflower oil (Ajinomoto Co., Inc.) was further added to obtain mayonnaise, which was designated as evaluation sample 5-7.
[0324] Furfural (Sigma-Aldrich) was added to safflower oil (Ajinomoto Co., Inc.) and dissolved at the concentration shown in Table 5 below (100 ppm relative to the safflower oil). The safflower oil was then heated at 100°C for 30 minutes using a water bath (Tokyo Rikakikai Co., Ltd.). In addition, β-caryophyllene (Sigma-Aldrich Co., Ltd.) was added to safflower oil (Ajinomoto Co., Inc.) and dissolved at the concentration shown in Table 5 below (100 ppm relative to safflower oil), and the safflower oil was then heated at 100°C for 30 minutes using a water bath (Tokyo Rikakikai Co., Ltd.). Each heated safflower oil was added in an amount of 0.1% by weight to the commercially available mayonnaise used in preparing the negative control (total of 0.2% by weight), and the resulting mayonnaise was designated as evaluation sample 5-8.
[0325] The mouth-coating sensation was evaluated in the same manner as in Test Example 1. The results are shown in Table 5 below. In the table, the substances in parentheses in the sample details mean that they were mixed before heating. For example, Evaluation Sample 5-1 "Heated (safflower oil + furfural + β-caryophyllene)" means that safflower oil, furfural and β-caryophyllene were mixed before heating, and Evaluation Sample 5-7 "Heated safflower oil + heated furfural + heated β-caryophyllene" means that safflower oil, furfural and β-caryophyllene were not mixed before heating, but were heated separately and then mixed.
[0326] [Table 5]
[0327] As is clear from the results in Table 5, the mouth-coating feel of evaluation samples 5-1 to 5-3 and 5-6 to 5-8 was effectively enhanced by the heated product of component (A) and / or the heated product of component (B) (specifically, heated products of β-caryophyllene, furfural and safflower oil, heated products of furfural and safflower oil, heated products of β-caryophyllene, etc.). On the other hand, in evaluation sample 5-4, in which only heated component (A2) was added, and evaluation sample 5-5, in which components (A1) and (A2) were heated separately and added, the mouth-coating feeling was hardly enhanced at all.
[0328] (Test Example 5-2) The positive control was a regular commercially available mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Mayonnaise", oil content: 73%) to which 0.2 wt% unheated mineral oil (manufactured by Kaneda Co., Ltd.) was added. The negative control was a commercially available mayonnaise with a lower fat content than the positive control mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Kokuma (registered trademark) 65% calorie reduction", fat content: 23%) to which 0.2 wt% unheated mineral oil (manufactured by Kaneda Co., Ltd.) was added.
[0329] <Evaluation Samples 5-9~5-20> 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 the mineral oil was heated at 100°C for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.). The heated mineral oil was added at 0.1% by weight 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 resulting mayonnaise was designated as evaluation sample 5-9.
[0330] 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 using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.) The heated mineral oil was added at 0.1% by weight 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 resulting mayonnaise was designated as evaluation sample 5-10.
[0331] 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 the mineral oil was heated at 100°C for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.) The heated mineral oil was added at 0.1% by weight 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 resulting mayonnaise was designated as evaluation sample 5-11.
[0332] 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 using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.) The heated mineral oil was added at 0.1% by weight 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, which was designated as evaluation sample 5-12.
[0333] 2-Hexenal (Sigma-Aldrich) was added to mineral oil (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 using a water bath (Tokyo Rikakikai Co., Ltd.) The heated mineral oil was added at 0.1% by weight to the commercially available mayonnaise used in the preparation of the negative control, and then 0.1% by weight of unheated mineral oil was added to obtain mayonnaise, which was used as evaluation sample 5-13.
[0334] Furfural (Sigma-Aldrich) was added to mineral oil (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 then heated at 100°C for 30 minutes using a water bath (Tokyo Rikakikai Co., Ltd.) The heated mineral oil was added at 0.1% by weight 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 a mayonnaise, which was designated as evaluation sample 5-14.
[0335] β-Caryophyllene (Sigma-Aldrich) was added to mineral oil (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 then heated at 100°C for 30 minutes using a water bath (Tokyo Rikakikai Co., Ltd.) The heated mineral oil was added at 0.1% by weight 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, which was designated as evaluation sample 5-15.
[0336] 2-Hexenal, furfural and β-caryophyllene (all manufactured by Sigma-Aldrich) were heated at 100°C for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.), and then added to mineral oil and mixed. The amount of 2-hexenal, furfural and β-caryophyllene before heating was 100 ppm relative to the mineral oil. The obtained mixture was added at 0.1% by weight 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 a mayonnaise, which was designated as evaluation sample 5-16.
[0337] 2-Hexenal and furfural (both manufactured by Sigma-Aldrich Co., Ltd.) were added to mineral oil (manufactured by Kaneda Co., Ltd.) and dissolved at the concentrations shown in Table 7 below (2-hexenal: 100 ppm relative to mineral oil, furfural: 100 ppm relative to mineral oil). The mineral oil was then heated at 100°C for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.), and β-caryophyllene (manufactured by Sigma-Aldrich Co., Ltd.) heated at 100°C for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.) was added and mixed. The amount of β-caryophyllene before heating was 100 ppm relative to the mineral oil before heating. The mixture obtained was added at 0.1% by weight 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, which was used as evaluation sample 5-17.
[0338] 2-Hexenal and β-caryophyllene (both manufactured by Sigma-Aldrich Co., Ltd.) were added to mineral oil (manufactured by Kaneda Co., Ltd.) and dissolved at 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 using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.), and furfural (manufactured by Sigma-Aldrich Co., Ltd.) heated at 100°C for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.) was added and mixed. The amount of furfural before heating was 100 ppm relative to the mineral oil before heating. The obtained mixture was added at 0.1% by weight 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 5-18.
[0339] β-Caryophyllene and furfural (both manufactured by Sigma-Aldrich Co., Ltd.) 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). The mineral oil was then heated at 100°C for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.), and 2-hexenal (manufactured by Sigma-Aldrich Co., Ltd.) heated at 100°C for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.) was added and mixed. The amount of 2-hexenal before heating was 100 ppm relative to the mineral oil before heating. The obtained mixture was added at 0.1% by weight 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.
[0340] 2-Hexenal and furfural (both manufactured by Sigma-Aldrich Co., Ltd.) 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 then heated at 100°C for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.). 2-Hexenal and β-caryophyllene (both manufactured by Sigma-Aldrich Co., Ltd.) 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 the mineral oil was then heated at 100°C for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.). Each of the heated mineral oils was added in an amount of 0.1% by weight to the commercially available mayonnaise used in the preparation of the negative control (total of 0.2% by weight), and the resulting mayonnaise was designated as evaluation sample 5-20.
[0341] <Sensory evaluation> The mouth-coating sensation was evaluated in the same manner as in Test Example 1. The results are shown in Tables 6 and 7 below. In the tables, the substances in parentheses indicate that they were mixed before heating, as in Table 5.
[0342] [Table 6]
[0343] [Table 7]
[0344] As is clear from the results in Tables 6 and 7, the mouth-coating feel of evaluation samples 5-9 to 5-12 and 5-15 to 5-20 was effectively enhanced by the heated product of component (A) and / or the heated product of component (B) (specifically, heated products of β-caryophyllene, furfural and 2-hexenal, heated products of furfural and 2-hexenal, heated products of β-caryophyllene, etc.). On the other hand, in evaluation sample 5-13 in which only the heated product of component (A2) was added, and evaluation sample 5-14 in which only the heated product of component (A1) was added, the mouth-coating feeling was hardly enhanced.
[0345] (Test Example 6) <Positive and negative controls> As a positive control, a regular commercially available mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Mayonnaise", oil content: 73%) was used to which 0.1 wt% unheated mineral oil (manufactured by Kaneda Co., Ltd.) was added. The negative control was a commercially available mayonnaise with a lower fat content than the positive control mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Kokuuma (registered trademark) 65% calorie reduction", fat content: 23%) to which 0.1 wt% unheated mineral oil (manufactured by Kaneda Co., Ltd.) was added. <Evaluation Samples 6-1~6-41> Each compound shown in Tables 8 to 10 (all manufactured by Sigma-Aldrich) was added to mineral oil (manufactured by Kaneda Co., Ltd.) and dissolved at each concentration (100 ppm relative to mineral oil) shown in Tables 8 to 10, and the mineral oil was heated at 100°C for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.) Each heated mineral oil was added at 0.1 wt % to the commercially available mayonnaise used in the preparation of the negative control above, instead of adding unheated mineral oil, and the resulting mayonnaises were designated as evaluation samples 6-1 to 6-41. <Sensory evaluation> The mouth-coating sensation was evaluated in the same manner as in Test Example 1. The results are shown in Tables 8 to 10 below.
[0346] [Table 8]
[0347] [Table 9]
[0348] [Table 10]
[0349] As is clear from the results in Tables 8 to 10, the mouth-coating feel of each evaluation sample was enhanced by adding the heated product of component (A) and / or the heated product of component (B).
[0350] (Test Example 7) <Positive and negative controls> As a positive control, a regular commercially available mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Mayonnaise", oil content: 73%) was used to which 1 wt% of unheated rapeseed oil (manufactured by Ajinomoto Co., Inc.) was added. The negative control was a commercially available mayonnaise with a lower fat content than the positive control mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Kokuuma (registered trademark) 65% calorie reduction", fat content: 23%) to which 1% by weight of unheated rapeseed oil (manufactured by Ajinomoto Co., Inc.) was added. <Evaluation sample> A predetermined amount of β-caryophyllene and furfuryl alcohol (both manufactured by Sigma-Aldrich) was dissolved in rapeseed oil (manufactured by Ajinomoto Co., Inc.), and the rapeseed oil was heated at 100°C for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.). Each of the heated rapeseed oils was added at 1% by weight to the commercially available mayonnaise used in the preparation of the negative control, instead of adding unheated rapeseed oil, and the resulting mayonnaise was used as an evaluation sample. The amount of β-caryophyllene and furfuryl alcohol dissolved in the rapeseed oil was adjusted to be in the range of 0.001 to 10,000 ppm relative to the rapeseed oil, as shown in Table 11 below. <Sensory evaluation> The mouth-coating feel was evaluated by two expert panelists who tasted each of the positive control, negative control, and evaluation sample mayonnaises and scored the evaluation samples in increments of 0.1 points from 0.0 to 5.0 points, with the positive control being assigned a score of "5.0 points" and the negative control being assigned a score of "0.0 points." The results are shown in Table 11 below.
[0351] [Table 11]
[0352] As is clear from the results in Table 11, the mouth-coating feel of each evaluation sample was enhanced by the heated product of component (A) and / or the heated product of component (B) (specifically, heated products of β-caryophyllene, furfuryl alcohol, and rapeseed oil, etc.). Furthermore, there was a tendency for the scores of evaluation samples containing high concentrations of each heated substance (for example, evaluation samples in which the β-caryophyllene and furfuryl alcohol contained in the rapeseed oil at the time of heating was 1,000 to 10,000 ppm relative to the rapeseed oil) to tend to be slightly lower. This is presumably because a high concentration can result in an off-flavor, which makes it difficult to detect the mouth-coating sensation.
[0353] (Test Example 8) <Positive and negative controls> The positive and negative controls used were the same as those used in Test Example 1. <Evaluation sample> β-Caryophyllene and furfural (both manufactured by Sigma-Aldrich) were dissolved in rapeseed oil (manufactured by Ajinomoto Co., Inc.) so that each was 100 ppm relative to the rapeseed oil, and the rapeseed oil was then heated using an oil bath (manufactured by Yamato Scientific Co., Ltd.) under the conditions (temperature, time) shown in Table 12 below. Each of the heated rapeseed oils was added at 1 wt % to the commercially available mayonnaise used in the preparation of the negative control, instead of adding unheated rapeseed oil, and the resulting mayonnaise was used as an evaluation sample. <Sensory evaluation> The mouth-coating feel was evaluated in the same manner as in Test Example 7. The results are shown in Table 12 below.
[0354] [Table 12]
[0355] The results in Table 12 suggest that the heating conditions (temperature, time) of components (A) and (B) may affect the mouth-coating sensation enhancing effect of the resulting heated products of component (A) and component (B).
[0356] (Test Example 9) <Positive and negative controls> For the positive control, we used a model ramen soup [2.17 g of "Super Cup Soy Sauce" powdered soup (manufactured by Acecook Co., Ltd.), 1.60 g of chicken oil (manufactured by Maruzen Food Industry Co., Ltd.), 1.00 g of dark soy sauce (manufactured by Kikkoman Co., Ltd.), 0.40 g of Koji Base (manufactured by Ajinomoto Co., Ltd.), and 0.20 g of Maro Pork Oil (manufactured by Maruzen Food Industry Co., Ltd.) dissolved in hot water to make a total of 100 g. Fat content: 1.8%] to which 0.1% by weight of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) was added, and a commercially available fat spread (manufactured by Meiji Co., Ltd., product name "Seven Premium Karoyaka Soft", fat content: 70%) to which 0.1% by weight of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) was added was used. For the negative control, we used a model ramen soup with less fat and oil content than the positive control ramen soup [2.17 g of "Super Cup Soy Sauce" powdered soup (manufactured by Acecook Co., Ltd.), 0.80 g of chicken oil (manufactured by Maruzen Food Industry Co., Ltd.), 1.00 g of dark soy sauce (manufactured by Kikkoman Co., Ltd.), 0.40 g of Koji Base (manufactured by Ajinomoto Co., Ltd.), and 0.20 g of Maro Pork Oil (manufactured by Maruzen Food Industry Co., Ltd.) dissolved in hot water to make a total of 100 g. Fat and oil content: 1.0%] to which 0.1% by weight of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) was added, and a commercially available fat spread with less fat and oil content than the positive control fat spread (manufactured by Meiji Co., Ltd., product name "Meiji Corn Soft", fat and oil content: 64%) to which 0.1% by weight of unheated safflower oil (manufactured by Ajinomoto Co., Ltd.) was added. The positive control for mayonnaise was a regular commercially available mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Mayonnaise", oil content: 73%) to which 0.1 wt% unheated safflower oil (manufactured by Ajinomoto Co., Inc.) was added. The negative control was a commercially available mayonnaise with a lower fat content than the positive control mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Kokuma (registered trademark) 65% calorie reduction", fat content: 23%) to which 1% by weight of unheated safflower oil (manufactured by Ajinomoto Co., Inc.) was added. <Evaluation sample group 9-1> β-caryophyllene and furfural (both manufactured by Sigma-Aldrich) were dissolved in safflower oil (manufactured by Ajinomoto Co., Inc.) to a concentration of 100 ppm relative to the safflower oil. Instead of adding unheated safflower oil to each of the foods (commercially available mayonnaise, model ramen soup, and commercially available fat spread) used in the preparation of the negative control, 0.1% by weight of the safflower oil (unheated) in which the above-mentioned β-caryophyllene and furfural had been dissolved was added, and the resulting foods (mayonnaise, ramen soup, and fat spread) were designated as evaluation sample group 9-1. <Evaluation sample group 9-2> β-caryophyllene and furfural (both manufactured by Sigma-Aldrich) were dissolved in safflower oil (manufactured by Ajinomoto Co., Inc.) so that each was 100 ppm relative to the safflower oil, and the safflower oil was heated at 100° C. for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.) The heated safflower oil was added at 0.1% by weight to each of the foods (commercially available mayonnaise, model ramen soup, and commercially available fat spread) used in the preparation of the negative control above, instead of adding unheated safflower oil, and the resulting foods (mayonnaise, ramen soup, and fat spread) were designated as evaluation sample group 9-2. <Sensory evaluation> The mouth-coating feel was evaluated by a three-member expert panel who tasted the positive control, negative control, and evaluation sample foods (mayonnaise, ramen soup, and fat spread) and scored the evaluation samples in increments of 0.1 points from 0.0 to 5.0 points, with the positive control being assigned a score of "5.0 points" and the negative control being assigned a score of "0.0 points." The results are shown in Table 13 below.
[0357] [Table 13]
[0358] As is clear from the results in Table 13, the heated product of component (A) and / or the heated product of component (B) (specifically, heated products of β-caryophyllene, furfural and safflower oil) enhanced the mouth-coating feel in mayonnaise, ramen soup and fat spread.
[0359] (Test Example 10) <Positive and negative controls> The same positive and negative controls as those used in Test Example 7 were used. <Evaluation sample 10-1> β-caryophyllene and furfural (both manufactured by Sigma-Aldrich) were dissolved in rapeseed oil (manufactured by Ajinomoto Co., Inc.) to a concentration of 100 ppm relative to the rapeseed oil. Instead of adding unheated rapeseed oil to the commercially available mayonnaise used in the preparation of the negative control, 0.1% by weight of the rapeseed oil (unheated) in which the above-mentioned β-caryophyllene and furfural had been dissolved was added, and the resulting mayonnaise was designated as evaluation sample 10-1. <Evaluation sample 10-2> β-caryophyllene and furfural (both manufactured by Sigma-Aldrich) were dissolved in rapeseed oil (manufactured by Ajinomoto Co., Inc.) so that each was 100 ppm relative to the rapeseed oil, and the rapeseed oil was heated at 100° C. for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.) The heated rapeseed oil was added at 0.1% by weight to the commercially available mayonnaise used in the preparation of the negative control, instead of adding unheated rapeseed oil, and the resulting mayonnaise was designated as evaluation sample 10-2. <Sensory evaluation> The evaluation of mouth-coating sensation was carried out by a blind two-point discrimination evaluation (Figure 1) and a rating evaluation (Figure 2) by three expert panelists, each repeating three times (total of nine times). The rating evaluation was carried out by eating each of the mayonnaises of the positive control, negative control, and evaluation samples 10-1 and 10-2, and rating the evaluation samples 10-1 and 10-2 in the range of 0.0 to 5.0 points in 0.1 point increments, with the positive control being "5.0 points" and the negative control being "0.0 points." The results are shown in Figures 1 and 2.
[0360] As is clear from the results of Figures 1 and 2, in the blind sensory evaluation, the mouth-coating feel of mayonnaise was enhanced by the heated product of component (A) and / or the heated product of component (B) (specifically, the heated products of β-caryophyllene, furfural, and rapeseed oil).
[0361] (Test Example 11) <Positive and negative controls> The positive and negative controls used were the same as those used in Test Example 7. <Evaluation Samples 11-1~11-4> (a) β-caryophyllene (Sigma-Aldrich) was dissolved in rapeseed oil (Ajinomoto Co., Inc.) to a concentration of 10 ppm relative to the rapeseed oil, and the rapeseed oil was then heated at 100°C for 30 minutes using a water bath (Tokyo Rikakikai Co., Ltd.). (b) Furfuryl alcohol (Sigma-Aldrich) was dissolved in rapeseed oil to give a concentration of 100 ppm, and the rapeseed oil (Ajinomoto Co., Inc.) was then heated at 100°C for 30 minutes using a water bath (Tokyo Rikakikai Co., Ltd.). (c) β-caryophyllene and furfuryl alcohol (both manufactured by Sigma-Aldrich) were dissolved in rapeseed oil (manufactured by Ajinomoto Co., Inc.) to give concentrations of 10 ppm and 100 ppm, respectively, relative to the rapeseed oil, and the rapeseed oil was then heated at 100°C for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.). Instead of adding unheated rapeseed oil to the commercially available mayonnaise used to prepare the negative control, each of the heated rapeseed oils prepared in (a) to (c) above, and a mixture of the heated rapeseed oil prepared in (a) above and the heated rapeseed oil prepared in (b) above were added, and the resulting mayonnaises were designated evaluation samples 11-1 to 11-4. <Sensory evaluation> The mouth-coating feel was evaluated in the same manner as in Test Example 7. The results are shown in Table 14 below.
[0362] [Table 14]
[0363] As is clear from the results in Table 14, the mouth-coating feel was enhanced in both the evaluation sample prepared using the heated product of component (A) and the evaluation sample prepared using the heated product of component (B). Furthermore, the mouth-coating sensation was enhanced in both evaluation samples prepared using the heated product obtained by heating component (A) and component (B) together, and evaluation samples prepared using the heated product of component (A) and the heated product of component (B) obtained separately.
[0364] (Test Example 12) <Positive and negative controls> The positive and negative controls used were the same as those used in Test Example 1. <Evaluation sample groups 12-1 and 12-2> Rapeseed oil (Ajinomoto Co., Inc.), soybean oil (Ajinomoto Co., Inc.), corn oil (Ajinomoto Co., Inc.), olive oil (Ajinomoto Co., Inc.), safflower oil (Ajinomoto Co., Inc.), linseed oil (Asahi Co., Ltd.), perilla oil (Asahi Co., Ltd.), hydrogenated palm kernel oil (J Oil Mills Co., Ltd.), and medium chain fatty acid oil (Nisshin Oillio Group, Inc.) were heated directly at 100°C for 30 minutes using a water bath (Tokyo Rikakikai Co., Ltd.). Each heated solvent was added at 1% by weight to the commercially available mayonnaise used in the preparation of the negative control instead of adding unheated rapeseed oil, and the resulting mayonnaise was designated as evaluation sample group 12-1. (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.), perilla oil (manufactured by Asahi Co., Ltd.), hydrogenated palm kernel oil (manufactured by J Oil Mills Co., Ltd.), and medium-chain fatty acid oil (manufactured by Nisshin Oillio Group, Inc.) so that each was 100 ppm relative to the solvent, and then heated at 100°C for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.). Each of the heated solvents was added at 1% by weight to the commercially available mayonnaise used in the preparation of the negative control instead of adding unheated rapeseed oil, and the resulting mayonnaise was designated as evaluation sample group 12-2. <Sensory evaluation> The mouth-coating feel was evaluated in the same manner as in Test Example 7. The results are shown in Table 15 below.
[0365] [Table 15]
[0366] As is clear from the results in Table 15, the mouth-coating feel of the evaluation samples was enhanced regardless of whether rapeseed oil, soybean oil, corn oil, olive oil, safflower oil, linseed oil, perilla oil, hydrogenated palm kernel oil or medium-chain fatty acid oil was used as the oil or fat.
[0367] (Test Example 13) <Positive and negative controls> The positive control was a regular commercially available mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Mayonnaise", oil content: 73%) to which 0.1 wt% unheated safflower oil (manufactured by Ajinomoto Co., Inc.) was added. The negative control was a commercially available mayonnaise with a lower fat content than the positive control mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Kokuma (registered trademark) 65% calorie reduction", fat content: 23%) to which 0.1 wt% unheated safflower oil (manufactured by Ajinomoto Co., Inc.) was added. <Evaluation sample> A predetermined amount of β-caryophyllene and furfural (both manufactured by Sigma-Aldrich) was dissolved in safflower oil (manufactured by Ajinomoto Co., Inc.), and the safflower oil was heated at 100°C for 30 minutes using a water bath (manufactured by Tokyo Rikakikai Co., Ltd.). Each heated safflower oil was added at 0.1% by weight to the commercially available mayonnaise used in the preparation of the negative control, instead of adding unheated rapeseed oil, and the resulting mayonnaise was used as an evaluation sample. The amount of β-caryophyllene and furfural dissolved in the safflower oil was adjusted to be in the range of 0.001 to 300,000 ppm relative to the safflower oil, as shown in Tables 16 to 19 below. <Sensory evaluation> The intensity of the mouth-coating sensation was evaluated by two expert panelists who tasted each of the positive control, negative control, and evaluation sample mayonnaises and scored the evaluation samples in increments of 0.1 points from 0.0 to 5.0 points, with the positive control being assigned a score of "5.0 points" and the negative control being assigned a score of "0.0 points." The results are shown in Tables 16 to 19 below.
[0368] [Table 16]
[0369] [Table 17]
[0370] [Table 18]
[0371] [Table 19]
[0372] As is clear from the results in Tables 16 to 19, the mouth-coating feel of each evaluation sample was enhanced by heating component (A) and / or heating component (B) (specifically, β-caryophyllene and / or furfural, and heated safflower oil, etc.).
[0373] (Test Example 14) <Synthesis Example> (Synthesis of Clobandiol and Clobandiol-3-monoacetate) β-Caryophyllene oxide (11 mg) was dissolved in 80% acetic acid aqueous solution (1 mL) and left at room temperature for 11 days. Excessive solvent was removed by distillation under reduced pressure, and the residue was purified by reversed-phase high performance liquid chromatography (HPLC) (water-ethanol) to obtain the following compound 1 (clobandiol) (1.2 mg) and compound 2 (clobandiol-3-monoacetate) (0.7 mg).
[0374] Compound 1 (Clobandiol):
[0375] [ka]
[0376] Compound 2 (Clobandiol-3-monoacetate):
[0377] [ka]
[0378] (Synthesis of clobandiol diacetate) Clobandiol (5 mg) was dissolved in acetic acid (0.2 mL) and stirred for 20 hours at 80° C. The reaction solution was concentrated to dryness under reduced pressure, and the resulting residue was purified by reverse phase HPLC (water-ethanol) to obtain the following compound 3 (clobandiol diacetate) (1.2 mg).
[0379] Compound 3 (Clobandiol diacetate):
[0380] [ka]
[0381] (Synthesis of clobandiol-3-monoisovalerate) Clobandiol (5.7 mg) was dissolved in isovaleric acid (0.1 mL) and stirred at 80° C. for 20 hours. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution, followed by partition extraction with ethyl acetate. The organic layer was dehydrated and dried over anhydrous sodium sulfate, and then concentrated to dryness under reduced pressure. The resulting residue was purified by reverse phase HPLC (water-ethanol) to obtain the following compound 4 (clobandiol-3-monoisovalerate) (2 mg).
[0382] Compound 4 (Clobandiol-3-monoisovalerate):
[0383] [ka]
[0384] (Synthesis of 2-methoxyclobanol) Tetracyanoethylene (13 mg) was added to a methanol solution (2 mL) of β-caryophyllene oxide (227 mg) and stirred at room temperature for 20 hours. The reaction solution was concentrated to dryness under reduced pressure, and the resulting residue was purified by reversed-phase HPLC (water-acetonitrile) to obtain the following compound 5 (2-methoxyclobanol) (30 mg).
[0385] Compound 5 (2-Methoxyclobanol):
[0386] [ka]
[0387] 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 β-Caryophyllene oxide (32 mg) was heated under reflux for 3 hours in pH 4 acetic acid-sodium acetate buffer / acetonitrile (1:1) (1 mL). Water and n-hexane were added to the reaction solution and partitioned. The organic layer fraction was purified by reverse phase HPLC (water-acetonitrile) to obtain the following compound 6 (2.5 mg) and compound 7 (0.2 mg).
[0388] Compound 6 ((1R,3Z,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol):
[0389] [ka]
[0390] Compound 7 ((1R,4R,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undecane-4,5-diol):
[0391] [ka]
[0392] (Synthesis of Caryophylladienol II) Tetracyanoethylene (28 mg) and lithium bromide (465 mg) were added to an acetone solution (2 mL) of β-caryophyllene oxide (235 mg) and stirred at room temperature for 1 hour. A 10% aqueous solution of sodium thiosulfate was added to the reaction solution, followed by partition extraction with hexane. The organic layer was dehydrated and 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 (caryophylladienol II) (105 mg).
[0393] Compound 8 (Caryophylladienol II):
[0394] [ka]
[0395] (Synthesis of (1S,5R,9R)-10,10-dimethyl-2,6-bismethylene-bicyclo[7.2.0]undecane-5-ol acetate and (1R,3EZ,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol-5-acetate) Acetic anhydride (0.08 mL) was added to a pyridine solution (0.1 mL) of caryophylladienol (12 mg) and the mixture was left 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 compound 9 (2.1 mg) and compound 10 (0.7 mg), respectively.
[0396] Compound 9 ((1S,5R,9R)-10,10-dimethyl-2,6-bismethylene-bicyclo[7.2.0]undecane-5-ol acetate):
[0397] [ka]
[0398] Compound 10 ((1R,3EZ,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol-5-acetate):
[0399] [ka]
[0400] <Positive and negative controls> As a positive control, a regular commercially available mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Mayonnaise", oil content: 73%) to which 0.001 wt % ethanol (manufactured by Japan Alcohol Industry Co., Ltd.) was added was used. The negative control was a commercially available mayonnaise with a lower fat content than the positive control mayonnaise (manufactured by Ajinomoto Co., Inc., product name "Pure Select (registered trademark) Kokuuma (registered trademark) 65% calorie reduction", fat content: 23%) to which 0.001% by weight of ethanol (manufactured by Japan Alcohol Industry Co., Ltd.) was added. <Evaluation sample> A given amount of β-caryophyllene, β-caryophyllene oxide, cloveniol, (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, cloveniol-3-monoacetate, cloveniol diacetate, cloveniol-3-monoisovalerate, α-pinene, α-pinene oxide, limonene, limonene oxide, α-terpinenol (cloveniol, (1R,3Z,5R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undecane-4,5-diol, Lenbicyclo[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, clobandiol-3-monoacetate, clobandiol diacetate, and clobandiol-3-monoisovalerate were obtained as in the above Synthesis Examples, and all other compounds were manufactured by Sigma-Aldrich Corporation) and dissolved in ethanol (manufactured by Japan Alcohol Industry Co., Ltd.), and 0.001% by weight of the ethanol was added to the commercially available mayonnaise used in the preparation of the negative control, and the resulting mayonnaise was used as the evaluation sample. The amounts of β-caryophyllene, β-caryophyllene oxide, cloveniol, (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, cloveniol-3-monoacetate, cloveniol diacetate, cloveniol-3-monoisovalerate, α-pinene, α-pinene oxide, limonene, limonene oxide, and α-terpinenol dissolved in ethanol were adjusted to be in the range of 0.01 to 1 ppm relative to the mayonnaise, as shown in Table 20 below. <Sensory evaluation> The intensity of the mouth-coating sensation was evaluated by a three-member expert panel who tasted each of the positive control, negative control, and evaluation sample mayonnaises and scored the evaluation samples in increments of 0.1 points from 0.0 to 5.0 points, with the positive control being assigned a score of "5.0 points" and the negative control being assigned a score of "0.0 points." The results are shown in Table 20 below.
[0401] [Table 20]
[0402] As is clear from the results in Table 20, the mouth-coating feel of each evaluation sample was enhanced by the addition of β-caryophyllene oxide, clobandiol, (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, clobandiol-3-monoacetate, clobandiol diacetate, clobandiol-3-monoisovalerate, α-pinene oxide, limonene oxide, and α-terpinenol.
[0403] (Test Example 15) <Preparation of control instant noodles> 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) were dissolved in 34 parts by weight of water, and 35.8 parts by weight of the resulting aqueous solution (kneading water) was added to 100 parts by weight of wheat flour (semi-strong flour) and kneaded for 2 minutes. The resulting noodle dough was made into a sheet (thickness: 1.5±0.2 mm) using an electric pasta machine manufactured by Marcato S.pA., and after cutting off both ends, it was cut into a width of 1 mm and a length of 30 cm. The resulting noodles were kneaded, and then passed through a continuous steamer (manufactured by Fuji Seisakusho Co., Ltd.) and steamed with steam at 100°C for 2 minutes. 30 g of 5% saline solution heated to about 50°C was added to 100 g of steamed noodles to season them. The flavored 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, the instant noodles are referred to as "control instant noodles"). The instant noodles were stored in a refrigerator at 5°C until use. <Preparation of heated object A> β-Polyolefin and furfural (both manufactured by Sigma-Aldrich) were dissolved in medium-chain fatty acid oil (manufactured by Fuji Oil Co., Ltd.) to a concentration of 1000 ppm each, and the medium-chain fatty acid oil was then heated at 95°C for 30 minutes using a kneader (TK Combimix, manufactured by Primix Corporation) (the resulting heated product is hereinafter referred to as "heated product A"). <Preparation of instant noodles for evaluation sample 15-1> Instant noodles were produced in the same manner as the control, except that when preparing the kneading water by dissolving salt, potassium carbonate, and sodium carbonate in water, 0.003 parts by weight of heated product A was further added and uniformly dispersed, and 35.803 parts by weight of the obtained dispersion liquid was added to 100 parts by weight of wheat flour (hereinafter, this instant noodles will be referred to as "instant noodles of evaluation sample 15-1"). <Preparation of instant noodles for evaluation sample 15-2> Instant noodles were produced in the same manner as the control, except that when preparing the kneading water by dissolving salt, potassium carbonate, and sodium carbonate in water, 0.007 parts by weight of heated product A was further added and uniformly dispersed, and 35.807 parts by weight of the obtained dispersion was added to 100 parts by weight of wheat flour (hereinafter, this instant noodles will be referred to as "instant noodles of evaluation sample 15-2"). <Preparation of instant noodles for evaluation sample 15-3> Instant noodles were produced in the same manner as the control, except that when preparing the kneading water by dissolving salt, potassium carbonate, and sodium carbonate in water, 0.02 parts by weight of heated product A was further added and uniformly dispersed, and 35.82 parts by weight of the obtained dispersion liquid was added to 100 parts by weight of wheat flour (hereinafter, this instant noodles will be referred to as "instant noodles of evaluation sample 15-3"). <Sensory evaluation> 100 g of evaluation samples 15-1 to 15-3 and the control instant noodles were boiled in 300 g of hot water at 100° C. for 3 minutes, and a sensory evaluation was performed. The sensory evaluation was performed by three trained expert panelists who gave scores by consensus in increments of 0.5 points for the evaluation samples 15-1 to 15-3 on the following criteria: "animal fat-like richness" (thickness and sustained sensation that appears "from the middle to the end" when animal fat is held in the mouth (specifically, 3 seconds after holding the animal fat in the mouth)), "animal fat-like sweetness" (sweetness that appears "from the tip to the middle" when animal fat is held in the mouth (specifically, within 2 seconds after holding the animal fat in the mouth)), and "mouth-coating sensation" (sensation of oil clinging to the inside of the mouth when slurping the noodles). In addition, for the overall evaluation, a product with a significantly improved oily feel compared to the control instant noodles was judged as "◎", a product with an oily feel compared to the control instant noodles was judged as "◯", and a product with no oily feel and the same as the control instant noodles was judged as "X".
[0404] (Evaluation criteria for animal fat-like richness, animal fat-like sweetness, and mouth-coating feel) +2 points: Stronger than control +1 point: Slightly stronger than control 0 points: equivalent to control -1 point: Slightly weaker than the control -2 points: Weaker than the control
[0405] The evaluation results are shown in Table 21 below.
[0406] [Table 21]
[0407] As is clear from the results in Table 21, the heated product of component (A) and / or the heated product of component (B) (specifically, the heated products of β-caryophyllene, furfural, and medium-chain fatty acid oil) enhanced the mouth-coating feel of each evaluation sample. Also, the animal fat-like richness and sweetness were enhanced.
[0408] (Test Example 16) <How to prepare creaming powder> (Model Creaming Powder 1) Model creaming powder 1 was prepared as follows. First, of the raw materials shown in Table 22 below, sodium hydroxide, acid casein, dipotassium hydrogen phosphate and powdered sugar were mixed with warm water at 60°C in the ratios shown in Table 22. Next, the remaining raw materials (hydrogenated palm kernel oil, monoglycerin fatty acid ester and sorbitan fatty acid ester) were added to the resulting mixture in the ratios shown in Table 22 and mixed. The resulting mixture was stirred at 8000 rpm for 15 minutes using a homomixer (product name: "Labo-lution", manufactured by Primix Corporation) for preliminary emulsification. Thereafter, the resulting emulsion was mixed at 400 kg / cm using a homogenizer (product name: "APV-2000", manufactured by APV Corporation). 2 The homogenized emulsion was spray-dried using a spray dryer (product name: "Mini Spray Dryer B-290", manufactured by BUCHI) under conditions of an intake air temperature of 180°C and an exhaust air temperature of 90°C, to obtain a creaming powder (model creaming powder 1).
[0409] [Table 22]
[0410] (Model Creaming Powder 2) A creaming powder (model creaming powder 2) was obtained in the same manner as model creaming powder 1, except that the emulsion obtained after preliminary emulsification was heated at 95°C for 30 minutes using a water bath (product name: "EC-Water Bath", manufactured by AS ONE Corporation) before homogenization.
[0411] (Model Creaming Powder 3) A creaming powder (model creaming powder 3) was obtained in the same manner as model creaming powder 1, except that the ingredients shown in Table 23 below were used instead of the ingredients shown in Table 22. Specifically, first, of the raw materials shown in Table 23 below, sodium hydroxide, acid casein, dipotassium hydrogen phosphate, and powdered candy were mixed with warm water at 60°C in the ratios shown in Table 23. Next, the remaining raw materials (hydrogenated palm kernel oil, monoglycerin fatty acid ester and sorbitan fatty acid ester, caryophyllene, and furfural) were added to the resulting mixture in the ratios shown in Table 23 and mixed. The resulting mixture was stirred at 8,000 rpm for 15 minutes using a homomixer (product name: "Labo-lution", manufactured by Primix Corporation) to perform pre-emulsification. Thereafter, the resulting emulsion was mixed at 400 kg / cm using a homogenizer (product name: "APV-2000", manufactured by APV Corporation). 2 The homogenized emulsion was spray-dried using a spray dryer (product name: "Mini Spray Dryer B-290", manufactured by BUCHI) under conditions of an intake air temperature of 180°C and an exhaust air temperature of 90°C, to obtain a creaming powder (model creaming powder 3).
[0412] [Table 23]
[0413] (Model Creaming Powder 4) A creaming powder (model creaming powder 4) was obtained in the same manner as model creaming powder 3, except that the emulsion obtained after preliminary emulsification was heated at 95°C for 30 minutes using a water bath (product name: "EC-Water Bath", manufactured by AS ONE Corporation) before homogenization.
[0414] All of the raw materials used in the preparation of model creaming powders 1 to 4 were commercially available. The manufacturers of each raw material are shown in Table 24 below.
[0415] [Table 24]
[0416] <Preparation of evaluation samples (cafe au lait in test areas 1 to 8)> The cafe au lait for test plots 1 to 8 were prepared by pouring 180 mL of boiling water into a cup containing the amounts of commercially available instant coffee powder (manufactured by Ajinomoto AGF Co., Ltd.), one of model creaming powders 1 to 4, and granulated sugar (manufactured by Mitsui Sugar Co., Ltd.) shown in Table 25 below, and stirring for several seconds until the powder was completely dissolved.
[0417] [Table 25]
[0418] <Sensory evaluation> The intensity of the mouth-coating feel (oil-like thickness that spreads throughout the mouth), milkiness (milky aroma and sweetness), and roasted coffee feel (coffee-like fragrant aroma and bitterness) of the cafe au lait of test plots 1 to 8 was evaluated by six trained expert panelists by rating them on a five-point scale (1 to 5 points: 1 point is the weakest and 5 points is the strongest) in increments of 1 point. Specifically, test plot 1 was used as the standard, and all of the mouth-coating feel, milkiness, and roasted coffee feel were defined as 1 point each. In addition, when the amount of model creaming powder in test plot 1 was increased by 1.5 times (test plot 2), the mouth-coating feel and milkiness were each defined as 5 points. Furthermore, when the amount of instant coffee powder in test plot 1 was increased by 1.1 times (test plot 7), the roasted coffee feel was defined as 3 points. The scores given by each expert panel were averaged, and the average score obtained was used as the evaluation of each cafe au lait. The evaluation results are shown in Table 26 below.
[0419] [Table 26]
[0420] As is clear from the results in Table 26, the mouth-coating feel, milky feel, and roasted coffee feel were enhanced in test group 5, which used heated components (A) and / or heated components (B) (specifically, heated products of β-caryophyllene, furfural, hydrogenated palm kernel oil, etc.).
[0421] (Test Example 17) <How to prepare creaming powder> (Model Creaming Powder 5) Model creaming powder 5 was prepared as follows. First, among the raw materials shown in Table 23, sodium hydroxide, acid casein, dipotassium hydrogen phosphate, and powdered candy were mixed with warm water at 60°C in the ratios shown in Table 17. Next, the remaining raw materials (hydrogenated palm kernel oil, monoglycerin fatty acid ester and sorbitan fatty acid ester, caryophyllene, and furfural) were added to the obtained mixture in the ratios shown in Table 23 and mixed. The obtained mixture was stirred at 8000 rpm for 15 minutes using a homomixer (product name: "Labo-lution", manufactured by Primix Corporation) to perform pre-emulsification. Thereafter, the obtained emulsion was sterilized by heating at 95°C for 15 seconds using a laboratory ultra-high temperature (UHT) sterilizer (product name: "ECONOLAB-T MK-2", manufactured by Power Point International), and then heated at 400 kg / cm using a homogenizer (product name: "APV-2000", manufactured by APV Corporation). 2 The homogenized emulsion was spray-dried using a spray dryer (product name: "Mini Spray Dryer B-290", manufactured by BUCHI) under conditions of an intake air temperature of 180°C and an exhaust air temperature of 90°C, to obtain a creaming powder (model creaming powder 5).
[0422] The raw materials used in the preparation of model creaming powder 5 were the same as those used in the preparation of model creaming powders 1 to 4.
[0423] <Preparation of evaluation sample (cafe au lait in test area 9)> The cafe au lait for test group 9 was prepared by pouring 180 mL of boiling water into a cup containing the amounts of commercially available instant coffee powder (manufactured by Ajinomoto AGF Co., Ltd.), model creaming powder 7, and granulated sugar (manufactured by Mitsui Sugar Co., Ltd.) shown in Table 27 below, and stirring for several seconds until the powder was completely dissolved.
[0424] [Table 27]
[0425] <Sensory evaluation> The cafe au lait of Test Plot 9 was evaluated for the intensity of mouth-coating feel, milky feel, and roasted coffee feel in the same manner as in Test Example 16. The evaluation results are shown in Table 28 below.
[0426] [Table 28]
[0427] As is clear from the results in Table 28, the heated products obtained by heating β-caryophyllene, furfural, hydrogenated palm kernel oil, etc. at 95°C for 15 seconds sufficiently enhanced the mouth-coating feel and roasted coffee feel.
[0428] (Test Example 18) <How to prepare creaming powder> (Model Creaming Powder 6) Model creaming powder 6 was prepared as follows. First, among the raw materials shown in Table 23, sodium hydroxide, acid casein, dipotassium hydrogen phosphate, and powdered candy were mixed with warm water at 60°C in the ratios shown in Table 17. Next, the remaining raw materials (hydrogenated palm kernel oil, monoglycerin fatty acid ester and sorbitan fatty acid ester, caryophyllene, and furfural) were added to the obtained mixture in the ratios shown in Table 23 and mixed. The obtained mixture was stirred at 8000 rpm for 15 minutes using a homomixer (product name: "Labo-lution", manufactured by Primix Corporation) to perform pre-emulsification. Thereafter, the obtained emulsion was heated at 95°C for 10 minutes using a water bath (product name: "EC-Water Bath", manufactured by AS ONE Corporation), and then heated at 400 kg / cm using a homogenizer (product name: "APV-2000", manufactured by APV Corporation). 2 The homogenized emulsion was spray-dried using a spray dryer (product name: "Mini Spray Dryer B-290", manufactured by BUCHI) under conditions of an intake air temperature of 180°C and an exhaust air temperature of 90°C, to obtain a creaming powder (model creaming powder 6).
[0429] (Model Creaming Powder 7) A creaming powder (model creaming powder 7) was obtained in the same manner as model creaming powder 6, except that the emulsion obtained after preliminary emulsification was heated at 95°C for 60 minutes using a water bath before homogenization.
[0430] (Model Creaming Powder 8) A creaming powder (model creaming powder 8) was obtained in the same manner as model creaming powder 6, except that the emulsion obtained after preliminary emulsification was heated at 80°C for 10 minutes using a water bath before homogenization.
[0431] (Model Creaming Powder 9) A creaming powder (model creaming powder 9) was obtained in the same manner as model creaming powder 6, except that the emulsion obtained after preliminary emulsification was heated at 80°C for 30 minutes using a water bath before homogenization.
[0432] (Model Creaming Powder 10) A creaming powder (model creaming powder 10) was obtained in the same manner as model creaming powder 6, except that the emulsion obtained after preliminary emulsification was heated at 80°C for 60 minutes using a water bath before homogenization.
[0433] (Model Creaming Powder 11) A creaming powder (model creaming powder 11) was obtained in the same manner as model creaming powder 6, except that the emulsion obtained after preliminary emulsification was heated at 70°C for 10 minutes using a water bath before homogenization.
[0434] (Model Creaming Powder 12) A creaming powder (model creaming powder 12) was obtained in the same manner as model creaming powder 6, except that the emulsion obtained after preliminary emulsification was heated at 70°C for 30 minutes using a water bath before homogenization.
[0435] (Model Creaming Powder 13) A creaming powder (model creaming powder 13) was obtained in the same manner as model creaming powder 6, except that the emulsion obtained after preliminary emulsification was heated at 70°C for 60 minutes using a water bath before homogenization.
[0436] In the preparation of model creaming powders 6 to 13, the heating conditions (heating temperature, heating time) of the emulsion obtained after preliminary emulsification are shown in Table 29 below.
[0437] [Table 29]
[0438] The raw materials used in the preparation of model creaming powders 6 to 13 were the same as those used in the preparation of model creaming powders 1 to 4.
[0439] <Preparation of evaluation samples (cafe au lait in test areas 10 to 17)> The cafe au lait for test plots 10 to 17 was prepared by pouring 180 mL of boiling water into a cup containing commercially available instant coffee powder (manufactured by Ajinomoto AGF Co., Ltd.), one of model creaming powders 6 to 13, and granulated sugar (manufactured by Mitsui Sugar Co., Ltd.) in the amounts shown in Table 30 below, and stirring for several seconds until the powder was completely dissolved.
[0440] [Table 30]
[0441] <Sensory evaluation> The cafe au lait of test plots 10 to 17 were evaluated for the intensity of mouth-coating feel, milky feel, and roasted coffee feel in the same manner as in Test Example 16. The evaluation results are shown in Table 31 below.
[0442] [Table 31]
[0443] As is clear from the results in Table 31, the heated products obtained by heating β-caryophyllene, furfural, hydrogenated palm kernel oil, etc. at 70°C or higher sufficiently enhanced the mouth-coating feel and milky feel.
[0444] (Test Example 19) <How to prepare creaming powder> (Model Creaming Powder 14~17) Model creaming powders 14 to 17 were prepared as follows. First, sodium hydroxide, acid casein, dipotassium hydrogen phosphate, and powdered candy, among the raw materials shown in Table 32 below, were mixed with warm water at 60°C in the ratios shown in Table 32. Next, the remaining raw materials (hydrogenated palm kernel oil, monoglycerin fatty acid ester and sorbitan fatty acid ester, caryophyllene, and furfural) were added to the obtained mixture in the ratios shown in Table 32 and mixed. The obtained mixture was stirred at 8000 rpm for 15 minutes using a homomixer (product name: "Labo-lution", manufactured by Primix Corporation) to perform pre-emulsification. Thereafter, the obtained emulsion was heated at 95°C for 30 minutes using a water bath (product name: "EC-Water Bath", manufactured by AS ONE Corporation), and then heated at 400 kg / cm using a homogenizer (product name: "APV-2000", manufactured by APV Corporation). 2 The homogenized emulsion was spray-dried using a spray dryer (product name: "Mini Spray Dryer B-290", manufactured by BUCHI) under conditions of an intake air temperature of 180°C and an exhaust air temperature of 90°C to obtain creaming powders (model creaming powders 14 to 17).
[0445] [Table 32]
[0446] The raw materials used in the preparation of model creaming powders 14 to 17 were the same as those used in the preparation of model creaming powders 1 to 4.
[0447] <Preparation of evaluation samples (cafe au lait for test plots 18 to 21)> The cafe au lait for test plots 18 to 21 was prepared by pouring 180 mL of boiling water into a cup containing the amounts of commercially available instant coffee powder (manufactured by Ajinomoto AGF Co., Ltd.), one of model creaming powders 16 to 19, and granulated sugar (manufactured by Mitsui Sugar Co., Ltd.) shown in Table 33 below, and stirring for several seconds until the powder was completely dissolved.
[0448] [Table 33]
[0449] <Sensory evaluation> The cafe au lait of test plots 18 to 21 were evaluated for the intensity of mouth-coating feel, milky feel, and roasted coffee feel in the same manner as in Test Example 16. The evaluation results are shown in Table 34 below.
[0450] [Table 34]
[0451] As shown in Table 34, the roasted flavor of coffee tended to be significantly enhanced when the proportion of furfural was greater than that of β-caryophyllene. In addition, it is considered that the sample of Test Plot 21 had a strong roasted coffee flavor, and therefore the mouth-coating flavor and milky flavor could not be fully evaluated. [Industrial Applicability]
[0452] According to the present invention, a mouth-coating feel enhancer capable of enhancing the mouth-coating feel and a method for producing the same can be provided. Furthermore, the present invention can provide a food product having an enhanced mouth-coating feel and a method for producing the same. The present invention can also provide a method for enhancing the mouth-coating sensation. Furthermore, according to the present invention, a coffee roasting sensation enhancer capable of enhancing the roasting sensation of coffee and a method for producing the same can be provided. Furthermore, according to the present invention, a coffee beverage with an enhanced roasted coffee flavor and a method for producing the same can be provided. Furthermore, the present invention can provide a method for enhancing the roasted taste of coffee.
[0453] This application is based on patent application No. 2019-046558 filed in Japan (filing date: March 13, 2019), the contents of which are incorporated in their entirety herein.
Claims
1. A method for enhancing a coating feeling on a mouse, comprising adding a heated product (A) as follows, the heated product being obtained by heating at least (A) at 40 to 180°C for 0.1 to 500 minutes (excluding those obtained by heating (A) in the presence of shrimp, mushroom, sweet corn, or brewed miso): (A) (A1) General formula (I): 【Chemistry 1】 [During the ceremony, R 1 is an acyl group having 1 to 6 carbon atoms, a hydroxy group, or a 1-pyrrolyl group; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 2 is an alkyl group having 1 to 6 carbon atoms; n represents an integer of 0 to 3. Compounds represented by the formula: (A2) At least one selected from the group consisting of an aliphatic aldehyde having 3 to 14 carbon atoms, an aromatic aldehyde having 7 to 12 carbon atoms, an aliphatic alcohol having 3 to 12 carbon atoms, and an oil or fat.
2. R in the general formula (I) 1 is a formyl group or an acetyl group and Z is a single bond; or R in the general formula (I) 1 2. The method for enhancing mouth-coating feel according to claim 1, wherein is a hydroxy group or a 1-pyrrolyl group, and Z is a methylene group.
3. The method for enhancing mouth-coating feeling according to claim 1 or 2, wherein n is 0 or 1.
4. The method for enhancing mouth-coating sensation according to any one of claims 1 to 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-furyl methyl ketone, furfuryl alcohol, and 1-furfurylpyrrole.
5. The method for enhancing mouth-coating feeling according to any one of claims 1 to 4, wherein (A2) is an oil or fat.
6. The method for enhancing a mouth-coating feeling according to any one of claims 1 to 5, which is a method for enhancing a mouth-coating feeling of an oil-containing food.
7. A method for producing a food, comprising heating the following (A) at 40 to 180°C for 0.1 to 500 minutes (excluding the case where (A) is heated in the presence of shrimp, mushroom, sweet corn, or brewed miso): (A) (A1) General formula (I): 【Chemistry 2】 [During the ceremony, R 1 is an acyl group having 1 to 6 carbon atoms, a hydroxy group, or a 1-pyrrolyl group; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 2 is an alkyl group having 1 to 6 carbon atoms; n represents an integer of 0 to 3. Compounds represented by the formula: (A2) At least one selected from the group consisting of an aliphatic aldehyde having 3 to 14 carbon atoms, an aromatic aldehyde having 7 to 12 carbon atoms, an aliphatic alcohol having 3 to 12 carbon atoms, and an oil or fat.
8. R in the general formula (I) 1 is a formyl group or an acetyl group and Z is a single bond; or R in the general formula (I) 1 8. The process according to claim 7, wherein Z is a hydroxy group or a 1-pyrrolyl group, and Z is a methylene group.
9. The method according to claim 7 or 8, wherein n is 0 or 1.
10. The method according to any one of claims 7 to 9, wherein the compound represented by the general formula (I) is at least one compound selected from the group consisting of furfural, 5-methylfurfural, 2-furyl methyl ketone, furfuryl alcohol, and 1-furfurylpyrrole.
11. The method according to any one of claims 7 to 10, wherein (A2) is an oil or fat.
12. The method according to any one of claims 7 to 11, wherein the food is a food with enhanced mouth-coating sensation.
13. The method according to any one of claims 7 to 12, wherein the food is an oil-containing food.
14. A method for producing a mouth-coating feel enhancer, comprising heating the following (A) at 40 to 180° C. for 0.1 to 500 minutes (excluding the case where (A) is heated in the presence of shrimp, mushroom, sweet corn, or brewed miso): (A) (A1) General formula (I): 【Chemistry 3】 [During the ceremony, R 1 is an acyl group having 1 to 6 carbon atoms, a hydroxy group, or a 1-pyrrolyl group; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R 2 is an alkyl group having 1 to 6 carbon atoms; n represents an integer of 0 to 3. Compounds represented by the formula: (A2) At least one selected from the group consisting of an aliphatic aldehyde having 3 to 14 carbon atoms, an aromatic aldehyde having 7 to 12 carbon atoms, an aliphatic alcohol having 3 to 12 carbon atoms, and an oil or fat.
15. R in the general formula (I) 1 is a formyl group or an acetyl group and Z is a single bond; or R in the general formula (I) 1 The process according to claim 14, wherein Z is a hydroxy group or a 1-pyrrolyl group, and Z is a methylene group.
16. The method according to claim 14 or 15, wherein n is 0 or 1.
17. The method according to any one of claims 14 to 16, wherein the compound represented by the general formula (I) is at least one compound selected from the group consisting of furfural, 5-methylfurfural, 2-furyl methyl ketone, furfuryl alcohol, and 1-furfurylpyrrole.
18. The method according to any one of claims 14 to 17, wherein (A2) is an oil or fat.
19. The method according to any one of claims 14 to 18, wherein the mouth-coating sensation enhancer is for use in foods containing fats and oils.
Citation Information
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