Classifications

• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
  • A23L7/00—Cereal-derived products; Malt products; Preparation or treatment thereof
  • A23L7/10—Cereal-derived products
  • A23L7/109—Types of pasta, e.g. macaroni or noodles
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
  • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
  • A23L29/03—Organic compounds
  • A23L29/035—Organic compounds containing oxygen as heteroatom
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/88—Taste or flavour enhancing agents
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
  • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
  • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
  • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
  • A23L33/30—Dietetic or nutritional methods, e.g. for losing weight
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
  • C11B9/00—Essential oils; Perfumes
  • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
  • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
  • A23F5/00—Coffee; Coffee substitutes; Preparations thereof
  • A23F5/24—Extraction of coffee; Coffee extracts; Making instant coffee
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
  • A23F5/00—Coffee; Coffee substitutes; Preparations thereof
  • A23F5/46—Coffee flavour; Coffee oil; Flavouring of coffee or coffee extract
  • A23F5/465—Flavouring with flavours other than natural coffee flavour or coffee oil

Definitions

• the present invention relates to a fragrance composition, and more particularly to a fragrance composition suitably used for enhancing a mouse coating feeling.
• the present invention also relates to a food product and a method for producing the same, and more particularly to a food product having an enhanced mouse coating feeling and the method for producing the same. Further, the present invention relates to a method for enhancing the feeling of mouse coating.
• “Mouth coating feeling” is the sensation that the oral cavity is covered with a thin film, which is noticeable when the oral cavity is filled with fat or oil-containing solution or food, and the oral cavity is covered with fat or oil-like film. If there is a method that can easily enhance the feeling of mouth coating, for example, even a small amount of fats and oils , Since it can sufficiently provide a favorable sensation that is noticeably felt when fats and oils are contained in the oral cavity, it is possible to suppress excessive calorie intake, and it can be expected to be effective in preventing metabolic diseases such as obesity. It is thought that there is.
• Non-Patent Documents 1 to 5 a method for enhancing the feeling of mouse coating.
• a method for enhancing the feeling of mouse coating a method utilizing hydrocolloids, small molecule compounds, polyphenols or glycosides (Non-Patent Documents 1 to 5) and the like have been reported.
• Patent Document 1 It has been reported that by adding cycloten, isovaleric acid and octanic acid to foods, a stewed dish-like flavor can be imparted.
• the present invention has been made in view of the above circumstances, and the problem to be solved thereof is a perfume composition capable of effectively enhancing the mouse coating feeling, a food having an effectively enhanced mouse coating feeling, and a food product thereof. It is an object of the present invention to provide a manufacturing method, a method for effectively enhancing a mouse coating feeling, and the like.
• the present inventors have (A) a compound represented by the following general formula (I) (eg, cycloten, etc.), (B) ⁇ -cariophyllene oxide, and (C) the following. It was found that the mouth coating feeling could be enhanced by adding at least two compounds selected from the group consisting of the compounds represented by the general formula (II) (eg, furfural, etc.) to foods, and further research was conducted. By proceeding, the present invention was completed. That is, the present invention is as follows.
• Ring A is a 5- or 6-membered, saturated or unsaturated, carbocyclic or oxygen-containing or nitrogen-containing heterocycle;
• R 1 is an oxo group, a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an acyloxy group having 1 to 4 carbon atoms, a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, or a hydrocarbon group.
• R 1 is a hydrogen atom and R 1 is a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, the carbon atom in the hydrocarbon group is bonded to the carbon atom of the ring A.
• R2 is a hydrocarbon group, a hydroxy group or a hydrogen atom having 1 to 8 carbon atoms; n indicates an integer of 1 to 3]
• R 3 is an acyl group having 1 to 6 carbon atoms, a hydroxy group, a pyrrole group or an acyloxy group having 1 to 6 carbon atoms;
• Z is a single bond or an alkylene group having 1 to 6 carbon atoms;
• R4 is a substituent;
• m indicates an integer from 0 to 3]
• a fragrance composition containing at least two compounds selected from the group consisting of the compounds represented by.
• the above (A) is cycloten, ⁇ -butyrolactone, 2-methyltetrahydrofuran-3-one, ⁇ -angelicalactone, maltor, 3-methyl-1,2-cyclohexanedione, ⁇ -dodecalactone, 5-dodecanolide.
• the above (C) is furfural, 2-acetylfuran, 2-acetyl-5-methylfuran, 3-acetyl-2,5-dimethylfuran, furfuryl alcohol, 1-furfurylpyrrole, furfuryl propionate,
• the composition according to [1] or [2] which is at least one compound selected from the group consisting of 5-methylfurfural and 5- (hydroxymethyl) furfural.
• the compound of [1] to [3], wherein at least two compounds selected from the group consisting of (A), (B) and (C) are any of the following (i) to (xviii).
• At least two compounds selected from the group consisting of one compound (iv) (A) ⁇ -angelicalactone, (B) ⁇ -cariophyllene oxide and (C) furfural (v) (A) maltor, (B) ⁇ -cariophyllene. From the group consisting of at least two compounds (vi) (A) 3-methyl-1,2-cyclohexanedione, (B) ⁇ -cariophyllene oxide and (C) fulfural selected from the group consisting of oxide and (C) flufural.
• Two compounds (xv) At least two compounds (xvi) (A) cycloten, (B) ⁇ -cariophyllene oxide and (C) propionic acid selected from the group consisting of cloten, (B) ⁇ -cariophyllene oxide and (C) 1-furfurylpyrrole.
• At least two compounds selected from the group consisting of flufuryl At least two compounds selected from the group consisting of (B) ⁇ -cariophyllene oxide and (C) 5-methylfurfural (xviii)
• the compound of [1] to [4], wherein at least two compounds selected from the group are at least two compounds selected from the group consisting of (A) cycloten, (B) ⁇ -cariophyllene oxide and (C) furfural.
• the composition contains at least (A) and (B), and the weight ratio (A: B) of the content of (A) to the content of (B) in the composition is A: B.
• the composition contains at least (A) and (C), and the weight ratio (A: C) of the content of (A) to the content of (C) in the composition is A: C.
• the composition contains at least (B) and (C), and the weight ratio (B: C) of the content of (B) to the content of (C) in the composition is B: C.
• the concentration a of (A) in the food is 0.05 to 5000 weight ppb with respect to the total weight of the food at the time of eating.
• composition contains at least (B), the composition has a concentration b of (B) in the food of 0.1 to 50,000 by weight ppb with respect to the total weight of the food when eaten. , Which is added to foods;
• the composition contains at least (C)
• the composition has a concentration c of (C) in the food of 0.1 to 50,000 by weight ppb with respect to the total weight of the food when eaten.
• the composition according to any one of [1] to [11], which is added to food. [13]
• the composition contains at least (A), and the concentration a of (A) in the food is 0.05 to 5000 weight ppb with respect to the total weight of the food at the time of eating.
• the composition contains at least (B), and the concentration b of (B) in the food is 0.1 to 50,000 by weight ppb with respect to the total weight of the food at the time of eating.
• the composition contains at least (C), and the concentration c of (C) in the food is 0.1 to 50,000 by weight ppb with respect to the total weight of the food at the time of eating.
• the composition contains at least (A) and (B)
• the composition has a weight ratio (a: b) of the concentration a of (A) to the concentration b of (B) in the food.
• A: b 1: 0.001 to 1000, which is added to foods;
• the composition contains at least (A) and (C)
• the composition has a weight ratio (a: c) of the concentration a of (A) to the concentration c of (C) in the food as a :.
• composition contains at least (B) and (C), the composition has a weight ratio (b: c) of the concentration b of (B) to the concentration c of (C) in the food b :.
• the composition contains at least (A) and (B), and the composition has a weight ratio (a: b) of the concentration a of (A) to the concentration b of (B) in the food.
• the composition according to any one of [1] to [16], which is added to foods so that a: b 1: 0.001 to 1000.
• the composition contains at least (A) and (C), and the composition has a weight ratio (a: c) of the concentration a of (A) to the concentration c of (C) in the food.
• the composition contains at least (B) and (C), and the composition has a weight ratio (b: c) of the concentration b of (B) to the concentration c of (C) in the food.
• the composition according to any one of [1] to [18], which is added to foods so that b: c 1: 0.001 to 1000.
• (A) General formula (I):
• Ring A is a 5- or 6-membered, saturated or unsaturated, carbocyclic or oxygen-containing or nitrogen-containing heterocycle;
• R 1 is an oxo group, a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an acyloxy group having 1 to 4 carbon atoms, a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, or a hydrocarbon group.
• R 1 is a hydrogen atom and R 1 is a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, the carbon atom in the hydrocarbon group is bonded to the carbon atom of the ring A.
• R2 is a hydrocarbon group, a hydroxy group or a hydrogen atom having 1 to 8 carbon atoms; n indicates an integer of 1 to 3]
• R 3 is an acyl group having 1 to 6 carbon atoms, a hydroxy group, a pyrrole group or an acyloxy group having 1 to 6 carbon atoms;
• Z is a single bond or an alkylene group having 1 to 6 carbon atoms;
• R4 is a substituent;
• m indicates an integer from 0 to 3]
• the above (A) is cycloten, ⁇ -butyrolactone, 2-methyltetrahydrofuran-3-one, ⁇ -angelicalactone, maltor, 3-methyl-1,2-cyclohexanedione, ⁇ -dodecalactone, 5-dodecanolide. , 4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-one and D-camper, which is at least one compound selected from the group, according to the production method according to [20].
• At least two compounds selected from the group consisting of one compound (iv) (A) ⁇ -angelicalactone, (B) ⁇ -cariophyllene oxide and (C) furfural (v) (A) maltor, (B) ⁇ -cariophyllene. From the group consisting of at least two compounds (vi) (A) 3-methyl-1,2-cyclohexanedione, (B) ⁇ -cariophyllene oxide and (C) fulfural selected from the group consisting of oxide and (C) flufural.
• Two compounds (xv) At least two compounds (xvi) (A) cycloten, (B) ⁇ -cariophyllene oxide and (C) propionic acid selected from the group consisting of cloten, (B) ⁇ -cariophyllene oxide and (C) 1-furfurylpyrrole.
• At least two compounds selected from the group consisting of flufuryl At least two compounds selected from the group consisting of (B) ⁇ -cariophyllene oxide and (C) 5-methylfurfural (xviii)
• the manufacturing method according to any one.
• the addition of (A) means that the concentration a of (A) in the food is 0. Performed to be 05-5000 weight ppb;
• the addition of (B) means that the concentration b of (B) in the food is 0.1 to 50,000 with respect to the total weight of the food when eaten.
• the production method comprises adding at least (C)
• the addition of (C) means that the concentration c of (C) in the food is 0.1 to 50,000 with respect to the total weight of the food when eaten.
• the production method includes adding at least (A), and the addition of (A) means that the concentration a of (A) in the food is 0.05 with respect to the total weight of the food at the time of eating.
• the production method includes adding at least (B), and the addition of (B) means that the concentration b of (B) in the food is 0.1 with respect to the total weight of the food at the time of eating.
• the production method includes adding at least (C), and the addition of (C) means that the concentration c of (C) in the food is 0.1 with respect to the total weight of the food at the time of eating.
• the production method comprises adding at least (A) and (B)
• the addition of (A) and (B) is the concentration a of (A) and the concentration b of (B) in the food.
• the production method comprises adding at least (A) and (C)
• the addition of (A) and (C) is the weight of the concentration a of (A) and the concentration c of (C) in the food.
• the addition of (B) and (C) is the weight of the concentration b of (B) and the concentration c of (C) in the food.
• the production method comprises adding at least (A) and (B), and the addition of (A) and (B) includes the concentration a of (A) and the concentration b of (B) in the food.
• the production method comprises adding at least (A) and (C), and the addition of (A) and (C) includes the concentration a of (A) and the concentration c of (C) in the food.
• the production method according to any one of [20] to [32], wherein the weight ratio (a: c) of the above is a: c 1: 0.001 to 1000.
• the production method comprises adding at least (B) and (C), and the addition of (B) and (C) includes the concentration b of (B) and the concentration c of (C) in the food.
• the production method according to any one of [20] to [33], wherein the weight ratio (b: c) of the above is b: c 1: 0.001 to 1000.
• Ring A is a 5- or 6-membered, saturated or unsaturated, carbocyclic or oxygen-containing or nitrogen-containing heterocycle;
• R 1 is an oxo group, a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an acyloxy group having 1 to 4 carbon atoms, a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, or a hydrocarbon group.
• R 1 is a hydrogen atom and R 1 is a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, the carbon atom in the hydrocarbon group is bonded to the carbon atom of the ring A.
• R2 is a hydrocarbon group, a hydroxy group or a hydrogen atom having 1 to 8 carbon atoms; n indicates an integer of 1 to 3]
• R 3 is an acyl group having 1 to 6 carbon atoms, a hydroxy group, a pyrrole group or an acyloxy group having 1 to 6 carbon atoms;
• Z is a single bond or an alkylene group having 1 to 6 carbon atoms;
• R4 is a substituent;
• m indicates an integer from 0 to 3]
• (A) is cycloten, ⁇ -butyrolactone, 2-methyltetrahydrofuran-3-one, ⁇ -angelicalactone, maltor, 3-methyl-1,2-cyclohexanedione, ⁇ -dodecalactone, 5-dodecanolide,
• the food according to [35] which is at least one compound selected from the group consisting of 4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one and D-camfer.
• (C) is furfural, 2-acetylfuran, 2-acetyl-5-methylfuran, 3-acetyl-2,5-dimethylfuran, furfuryl alcohol, 1-furfurylpyrrole, furfuryl propionate, 5 -Food according to [35] or [36], which is at least one compound selected from the group consisting of methylfurfural and 5- (hydroxymethyl) furfural.
• At least two compounds selected from the group consisting of one compound (iv) (A) ⁇ -angelicalactone, (B) ⁇ -cariophyllene oxide and (C) furfural (v) (A) maltor, (B) ⁇ -cariophyllene. From the group consisting of at least two compounds (vi) (A) 3-methyl-1,2-cyclohexanedione, (B) ⁇ -cariophyllene oxide and (C) fulfural selected from the group consisting of oxide and (C) flufural.
• Two compounds (xv) At least two compounds (xvi) (A) cycloten, (B) ⁇ -cariophyllene oxide and (C) propionic acid selected from the group consisting of cloten, (B) ⁇ -cariophyllene oxide and (C) 1-furfurylpyrrole.
• At least two compounds selected from the group consisting of flufuryl At least two compounds selected from the group consisting of (B) ⁇ -cariophyllene oxide and (C) 5-methylfurfural (xviii) ( At least two compounds selected from the group consisting of A) cycloten, (B) ⁇ -cariophyllene oxide and (C) 5- (hydroxymethyl) furfural [39] (A) cycloten, (B) ⁇ -cariophyllene oxide and ( C) The food according to any one of [35] to [38], which contains at least two compounds selected from the group consisting of furfural. [40] The food according to any one of [35] to [39], which is a food having an enhanced mouse coating feeling.
• the concentration a of (A) in the food is 0.05 to 5000 weight ppb with respect to the total weight of the food at the time of eating;
• the concentration b of (B) in the food is 0.1 to 50,000 by weight ppb with respect to the total weight of the food when eaten;
• the concentration c of (C) in the food is 0.1 to 50,000 by weight ppb with respect to the total weight of the food at the time of eating, [35] to [41].
• the food contains at least (A), and the concentration a of (A) in the food is 0.05 to 5000 weight ppb with respect to the total weight of the food at the time of eating, [35] to The food product according to any one of [42].
• the food contains at least (B), and the concentration b of (B) in the food is 0.1 to 50,000 by weight ppb with respect to the total weight of the food at the time of eating, [35] to The food product according to any one of [43].
• the food contains at least (C), and the concentration c of (C) in the food is 0.1 to 50,000 by weight ppb with respect to the total weight of the food at the time of eating, [35] to The food according to any one of [44].
• Ring A is a 5- or 6-membered, saturated or unsaturated, carbocyclic or oxygen-containing or nitrogen-containing heterocycle;
• R 1 is an oxo group, a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an acyloxy group having 1 to 4 carbon atoms, a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, or a hydrocarbon group.
• R 1 is a hydrogen atom and R 1 is a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, the carbon atom in the hydrocarbon group is bonded to the carbon atom of the ring A.
• R2 is a hydrocarbon group, a hydroxy group or a hydrogen atom having 1 to 8 carbon atoms; n indicates an integer of 1 to 3]
• R 3 is an acyl group having 1 to 6 carbon atoms, a hydroxy group, a pyrrole group or an acyloxy group having 1 to 6 carbon atoms;
• Z is a single bond or an alkylene group having 1 to 6 carbon atoms;
• R4 is a substituent;
• m indicates an integer from 0 to 3]
• a method for enhancing the feeling of mouse coating which comprises adding at least two compounds selected from the group consisting of the compounds represented by.
• the above (A) is cycloten, ⁇ -butyrolactone, 2-methyltetrahydrofuran-3-one, ⁇ -angelicalactone, maltor, 3-methyl-1,2-cyclohexanedione, ⁇ -dodecalactone, 5-dodecanolide. , 4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-one and D-camper, which is at least one compound selected from the group, according to [50].
• the above (C) is furfural, 2-acetylfuran, 2-acetyl-5-methylfuran, 3-acetyl-2,5-dimethylfuran, furfuryl alcohol, 1-furfurylpyrrole, furfuryl propionate,
• the enhancement method according to [50] or [51] which is at least one compound selected from the group consisting of 5-methylfurfural and 5- (hydroxymethyl) furfural.
• the compound of [50] to [52] wherein at least two compounds selected from the group consisting of (A), (B) and (C) are any of the following (i) to (xviii).
• At least two compounds selected from the group consisting of one compound (iv) (A) ⁇ -angelicalactone, (B) ⁇ -cariophyllene oxide and (C) furfural (v) (A) maltor, (B) ⁇ -cariophyllene. From the group consisting of at least two compounds (vi) (A) 3-methyl-1,2-cyclohexanedione, (B) ⁇ -cariophyllene oxide and (C) fulfural selected from the group consisting of oxide and (C) flufural.
• Two compounds (xv) At least two compounds (xvi) (A) cycloten, (B) ⁇ -cariophyllene oxide and (C) propionic acid selected from the group consisting of cloten, (B) ⁇ -cariophyllene oxide and (C) 1-furfurylpyrrole.
• At least two compounds selected from the group consisting of flufuryl At least two compounds selected from the group consisting of (B) ⁇ -cariophyllene oxide and (C) 5-methylfurfural (xviii)
• the enhancement method according to any one of [50] to [54], which comprises adding (A), (B) and (C).
• the enhancing method includes adding at least (A)
• the addition of (A) means that the concentration a of (A) in the food is 0. Performed to be 05-5000 weight ppb
• the addition of (B) means that the concentration b of (B) in the food is 0.1-50000 with respect to the total weight of the food when eaten. Made to weigh ppb
• the addition of (C) means that the concentration c of (C) in the food is 0.1-50000 with respect to the total weight of the food when eaten.
• the augmentation method according to any one of [50] to [55], which is carried out so as to have a weight of ppb.
• the enhancing method includes adding at least (A), and the addition of (A) means that the concentration a of (A) in the food is 0.05 with respect to the total weight of the food at the time of eating.
• the enhancement method comprises adding at least (B), wherein the concentration b of (B) in the food is 0.1 relative to the total weight of the food when eaten.
• the augmentation method according to any one of [50] to [57], which is carried out so as to have a weight of up to 50,000 ppb.
• the enhancement method comprises adding at least (C), wherein the concentration c of (C) in the food is 0.1 with respect to the total weight of the food when eaten.
• the enhancing method comprises adding at least (A) and (B)
• the addition of (A) and (B) is the concentration a of (A) and the concentration b of (B) in the food.
• the addition of (A) and (C) is the weight of the concentration a of (A) and the concentration c of (C) in the food.
• the addition of (B) and (C) is the weight of the concentration b of (B) and the concentration c of (C) in the food.
• the enhancing method comprises adding at least (A) and (B), and the addition of (A) and (B) includes the concentration a of (A) and the concentration b of (B) in the food.
• the enhancing method comprises adding at least (A) and (C), and the addition of (A) and (C) includes the concentration a of (A) and the concentration c of (C) in the food.
• the enhancing method comprises adding at least (B) and (C), and the addition of (B) and (C) includes the concentration b of (B) and the concentration c of (C) in the food.
• the enhancement method according to any one of [50] to [62], wherein the weight ratio (b: c) of is b: c 1: 0.001 to 1000.
• a fragrance composition capable of effectively enhancing the feeling of mouse coating.
• a perfume composition capable of effectively enhancing the mouse coating feeling without imparting a strange flavor to the food.
• a food having an effectively enhanced mouse coating feeling and a method for producing the same.
• a food product having no off-flavor and having an effectively enhanced mouse coating feeling and a method for producing the same.
• INDUSTRIAL APPLICABILITY According to the present invention, it is possible to provide a method capable of effectively enhancing the feeling of mouse coating. Further, according to the present invention, it is possible to provide a method capable of effectively enhancing the feeling of mouse coating without imparting a strange flavor to food.
• composition of the present invention is (A) general formula (I) :.
• Ring A is a 5- or 6-membered, saturated or unsaturated, carbocyclic or oxygen-containing or nitrogen-containing heterocycle;
• R 1 is an oxo group, a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an acyloxy group having 1 to 4 carbon atoms, a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, or a hydrocarbon group.
• R 1 is a hydrogen atom and R 1 is a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, the carbon atom in the hydrocarbon group is bonded to the carbon atom of the ring A.
• R2 is a hydrocarbon group, a hydroxy group or a hydrogen atom having 1 to 8 carbon atoms; n indicates an integer of 1 to 3] (In the present specification, it may be simply referred to as "(A)"), (B) ⁇ -caryophyllene oxide (in the present specification, it may be simply referred to as "(B)”) and (C) General formula (II):
• R 3 is an acyl group having 1 to 6 carbon atoms, a hydroxy group, a pyrrole group or an acyloxy group having 1 to 6 carbon atoms; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R4 is a substituent; m indicates an integer from 0 to 3] (In the present specification, it may be simply referred to as "(C)").
• the main feature is that it contains at least two compounds selected from the group consisting of the active ingredients as active ingredients.
• the "flavor” refers to a food additive used to impart aroma, flavor, taste, etc. to a food.
• hydrocarbon group may be saturated or unsaturated, and examples thereof include an alkyl group, an alkenyl group, an alkynyl group, and an alkylidene group.
• the "alkyl group having 1 to 8 carbon atoms" may be linear or may have a branch.
• Specific examples of the alkyl group having 1 to 8 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a neopentyl group, and an isopentyl.
• alkenyl group having 2 to 8 carbon atoms may be linear or may have a branch.
• Specific examples of the alkenyl group having 2 to 8 carbon atoms include an ethenyl group, a 1-propenyl group, a 2-propenyl group, a 1-methylethenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group and a 2- Methyl-1-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 3-methyl-2-butenyl group, 1-hexenyl group, 3-hexenyl group, 5-hexenyl group , 4-Methyl-3-pentenyl group, 1-heptenyl group, 1-octenyl group and the like.
• alkynyl group having 2 to 8 carbon atoms may be linear or may have a branch.
• Specific examples of the alkynyl group having 2 to 8 carbon atoms include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group and a 2-.
• Examples include pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-hexynyl group, 2-hexynyl group, 3-hexynyl group, 4-hexynyl group, 5-hexynyl group, 1-heptynyl group, 1-octynyl group and the like. Be done.
• alkylidene group having 1 to 8 carbon atoms may be linear or may have a branch.
• Specific examples of the alkylidene group having 1 to 8 carbon atoms include a methylidene group, an ethylidene group, a propylidene group, an isopropylidene group, a butylidene group, a pentylidene group, a hexylidene group, a heptylidene group, an octylidene group and the like.
• the "substituted group" of “may have a substituent” includes, for example, a halogen atom, a hydroxy group, a nitro group, a cyano group, an alkyl group, an alkoxy group, an alkoxycarbonyl group, and an acyl group. , Acyloxy group, amino group, oxo group and the like.
• the substituent may be further substituted with the above-mentioned substituent.
• alkoxy group having 1 to 4 carbon atoms may be linear or may have a branch.
• Specific examples of the alkoxy group having 1 to 4 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a sec-butoxy group, a tert-butoxy group, an isobutoxy group and the like.
• acyloxy group having 1 to 4 carbon atoms include formyloxy group, acetoxy group, propionyloxy group and the like.
• Ring A in the general formula (I) represents a saturated or unsaturated carbon ring or oxygen-containing or nitrogen-containing heterocycle, and is preferably a saturated or unsaturated carbon ring or oxygen-containing heterocycle.
• the number of members of the ring A is 5 or 6, preferably 5.
• the heteroatom number of the heterocycle is 1 or 2, preferably 1.
• Ring A may, in one aspect, be a 5-membered, saturated or unsaturated, carbocycle or oxygen-containing or nitrogen-containing heterocycle.
• the ring A is a 5- or 6-membered saturated or unsaturated carbocycle or oxygen-containing heterocycle (preferably a carbocycle or an oxygen-containing heterocycle having 1 heteroatom). It may be there.
• the ring A may be a 5-membered, saturated or unsaturated, carbon ring or oxygen-containing heterocycle (preferably a carbon ring or an oxygen-containing heterocycle having 1 heteroatom). ..
• the ring A include a cyclopentane ring, a cyclopentadiene ring, a cyclopentadiene ring, a cyclohexane ring, a cyclohexene ring, a 1,3-cyclohexadiene ring, a 1,4-cyclohexadiene ring, a carbon ring such as a benzene ring; , 2,3-Dihydrofuran ring, 2,5-dihydrofuran ring, furan ring, tetrahydropyran ring, 2H-pyran ring, 4H-pyran ring and other oxygen-containing heterocycles; Rings and the like can be mentioned.
• Ring A is substituted with at least one oxo group as shown in the general formula (I).
• R 1 and R 2 in the general formula (I) are substituents bonded to a substitutable position of the ring A.
• R 1 and R 2 may be bonded to different atoms (carbon atom, hetero atom), or may be bonded to the same carbon atom if they can be substituted.
• R 1 in the general formula (I) has an oxo group, a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an acyloxy group having 1 to 4 carbon atoms, and 1 to 1 carbon atoms which may have a substituent.
• 8 shows a hydrocarbon group or a hydrogen atom.
• alkoxy group having 1 to 4 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a sec-butoxy group, a tert-butoxy group, an isobutoxy group and the like. It is preferably a methoxy group.
• the number of carbon atoms of the alkoxy group is preferably 1 to 3, and more preferably 1 or 2.
• acyloxy group having 1 to 4 carbon atoms include a formyloxy group, an acetoxy group, a propionyloxy group, and the like, preferably a formyloxy group and an acetoxy group.
• the number of carbon atoms of the acyloxy group is preferably 1 to 3, and more preferably 1 or 2.
• the "hydrocarbon group having 1 to 8 carbon atoms" of the "hydrocarbon group having 1 to 8 carbon atoms which may have a substituent" in R1 is, for example, an alkyl having 1 to 8 carbon atoms.
• Examples thereof include a group, an alkenyl group having 2 to 8 carbon atoms, an alkynyl group having 2 to 8 carbon atoms, an alkylidene group having 1 to 8 carbon atoms, and preferably an alkyl group having 1 to 8 carbon atoms and carbon. It is an alkenyl group having 2 to 8 atoms.
• alkyl group having 1 to 8 carbon atoms examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, and a pentyl group.
• Neopentyl group isopentyl group, 1-ethylpropyl group, hexyl group, isohexyl group, 1,1-dimethylbutyl group, 2,2-dimethylbutyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group , Octyl group and the like, preferably methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group, and more preferably methyl group, ethyl group, propyl.
• It is a group or an isopropyl group, and particularly preferably a methyl group or an ethyl group.
• the number of carbon atoms of the alkyl group is preferably 1 to 6, more preferably 1 to 5, still more preferably 1 to 4, and particularly preferably 1 to 3.
• alkenyl group having 2 to 8 carbon atoms include an ethenyl group, a 1-propenyl group, a 2-propenyl group, a 1-methylethenyl group, a 1-butenyl group, a 2-butenyl group and a 3-.
• the number of carbon atoms of the alkyl group is preferably 2 to 6, more preferably 2 to 5, still more preferably 2 to 4, and particularly preferably 2 or 3.
• alkynyl group having 2 to 8 carbon atoms include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, and a 1-.
• the number of carbon atoms of the alkynyl group is preferably 2 to 6, more preferably 2 to 5, still more preferably 2 to 4, and particularly preferably 2 or 3.
• alkylidene group having 1 to 8 carbon atoms examples include a methylidene group, an ethylidene group, a propyridene group, an isopropyridene group, a butylidene group, a pentylidene group, a hexylidene group, a heptylidene group, an octaliden group and the like.
• the number of carbon atoms of the alkylidene group is preferably 1 to 6, more preferably 1 to 5, still more preferably 1 to 4, and particularly preferably 1 to 3.
• Examples of the "substituent" of the "hydrocarbon group having 1 to 8 carbon atoms which may have a substituent" in R1 include a halogen atom, a hydroxy group, a nitro group, a cyano group, an alkyl group and an alkoxy. Examples thereof include a group, an alkoxycarbonyl group, an acyl group, an acyloxy group, an amino group, an oxo group and the like, and among them, a substituent containing an oxygen atom (eg, a hydroxy group, an alkoxycarbonyl group, an oxo group and the like) is preferable.
• a substituent containing an oxygen atom eg, a hydroxy group, an alkoxycarbonyl group, an oxo group and the like
• the number of substituents is not particularly limited as long as it can be substituted, but is preferably 1 to 3 and more. It is preferably one or two.
• each substituent may be the same or different.
• R 1 in the general formula (I) is a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent
• the carbon atom in the hydrocarbon group is bonded to the carbon atom of the ring A. Then, a crosslinked structure or a saturated or unsaturated ring structure may be formed.
• R 1 preferably contains an oxo group, a hydroxy group, an alkoxy group having 1 to 4 carbon atoms (eg, methoxy group, etc.), an acyloxy group having 1 to 4 carbon atoms (eg, acetoxy group, etc.), and a substituent. It may have a hydrocarbon group having 1 to 8 carbon atoms (eg, an alkyl group, an alkenyl group, etc.) or a hydrogen atom, and more preferably an oxo group, a hydroxy group, a methoxy group, an acetoxy group, or a substituent.
• Alkyl group having 1 to 8 carbon atoms eg, methyl group, ethyl group, heptyl group, octyl group, etc.
• alkenyl having 2 to 8 carbon atoms which may have a substituent. It is a group (eg, 1-methylethenyl group, etc.) or a hydrogen atom, and particularly preferably has an oxo group, a hydroxy group, a methoxy group, an acetoxy group, a substituent (eg, a hydroxy group, an alkoxycarbonyl group, etc.).
• a substituent eg, a hydroxy group, an alkoxycarbonyl group, etc.
• R 2 in the general formula (I) represents a hydrocarbon group having 1 to 8 carbon atoms, a hydroxy group or a hydrogen atom.
• R2 is preferably an alkyl group having 1 to 8 carbon atoms, an alkylidene group having 1 to 8 carbon atoms, a hydroxy group or a hydrogen atom, and more preferably an alkyl group having 1 to 8 carbon atoms (eg). , Methyl group, ethyl group, pentyl group, etc.), an alkylidene group having 1 to 8 carbon atoms (eg, a propylidene group, etc.), a hydroxy group or a hydrogen atom, and particularly preferably a methyl group, a pentyl group, a propyridene group, etc. It is a hydroxy group or a hydrogen atom.
• N in the general formula (I) represents an integer of 1 to 3.
• n preferably indicates 1 or 2, and more preferably 1.
• n in the general formula (I) is 2 or 3
• the plurality of R 2s may be the same or different.
• the suitable compound (I) is shown below.
• Ring A is a 5- or 6-membered saturated or unsaturated carbon ring;
• R 1 may have an oxo group, a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an acyloxy group having 1 to 4 carbon atoms, and a substituent, and may have 1 to 8 carbon atoms (preferably 1).
• It is an alkenyl group or a hydrogen atom having 2 to 8 (preferably 2 to 6) carbon atoms which may have an alkyl group and a substituent of (6), and R 1 has a substituent.
• alkenyl group having 2 to 8 (preferably 2 to 6) carbon atoms which may have an alkyl group or a substituent having 1 to 8 (preferably 1 to 6) carbon atoms.
• the carbon atom in the alkyl group or alkenyl group may be bonded to the carbon atom of ring A to form a crosslinked structure or a saturated or unsaturated ring structure;
• R2 is an alkyl group having 1 to 8 carbon atoms (preferably 1 to 6), an alkylidene group having 1 to 8 carbon atoms (preferably 1 to 6), a hydroxy group or a hydrogen atom;
• Compound (I) wherein n represents an integer of 1 to 3 (preferably 1, 2).
• Ring A is a 5- or 6-membered saturated or unsaturated oxygen-containing heterocycle;
• R 1 may have an oxo group, a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an acyloxy group having 1 to 4 carbon atoms, and a substituent, and may have 1 to 8 carbon atoms (preferably 1).
• It is an alkenyl group or a hydrogen atom having 2 to 8 (preferably 2 to 6) carbon atoms which may have an alkyl group and a substituent of (6), and R 1 has a substituent.
• alkenyl group having 2 to 8 (preferably 2 to 6) carbon atoms which may have an alkyl group or a substituent having 1 to 8 (preferably 1 to 6) carbon atoms.
• the carbon atom in the alkyl group or alkenyl group may be bonded to the carbon atom of ring A to form a crosslinked structure or a saturated or unsaturated ring structure;
• R2 is an alkyl group having 1 to 8 carbon atoms (preferably 1 to 6), an alkylidene group having 1 to 8 carbon atoms (preferably 1 to 6), a hydroxy group or a hydrogen atom;
• Compound (I) wherein n represents an integer of 1 to 3 (preferably 1, 2).
• Ring A is a 5- or 6-membered saturated or unsaturated nitrogen-containing heterocycle; R 1 may have an oxo group, a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an acyloxy group having 1 to 4 carbon atoms, and a substituent, and may have 1 to 8 carbon atoms (preferably 1). It is an alkenyl group or a hydrogen atom having 2 to 8 (preferably 2 to 6) carbon atoms which may have an alkyl group and a substituent of (6), and R 1 has a substituent.
• alkenyl group having 2 to 8 (preferably 2 to 6) carbon atoms which may have an alkyl group or a substituent having 1 to 8 (preferably 1 to 6) carbon atoms.
• the carbon atom in the alkyl group or alkenyl group may be bonded to the carbon atom of ring A to form a crosslinked structure or a saturated or unsaturated ring structure;
• R2 is an alkyl group having 1 to 8 carbon atoms (preferably 1 to 6), an alkylidene group having 1 to 8 carbon atoms (preferably 1 to 6), a hydroxy group or a hydrogen atom;
• Compound (I) wherein n represents an integer of 1 to 3 (preferably 1, 2).
• the compound (I) has the following general formula (Ia):
• Ring Aa is a 5- or 6-membered, saturated or unsaturated, carbocyclic or oxygen-containing or nitrogen-containing heterocycle; R 1a is an oxo group, a hydroxy group or a hydrogen atom; R 2a represents an alkyl group or a hydrogen atom having 1 to 8 carbon atoms] It may be a compound represented by.
• the compound represented by the general formula (Ia) may be referred to as "compound (Ia)".
• compound (Ia) each group of the general formula (Ia) will be described.
• the ring Aa in the general formula (Ia) is the same as the ring A in the general formula (I), and the preferred embodiments and specific examples are also the same.
• Ring Aa is substituted with at least one oxo group as shown in the general formula (Ia).
• the portion represented by is preferably selected from the following.
• portion in the general formula (Ia) is selected from the following.
• R 1a and R 2a in the general formula (Ia) are substituents bonded to a substitutable position of the ring Aa.
• R 1a and R 2a may be bonded to different atoms (carbon atom, hetero atom), or may be bonded to the same carbon atom if they can be substituted.
• R 1a in the general formula (Ia) represents an oxo group, a hydroxy group or a hydrogen atom.
• R 1a is preferably a hydroxy group or a hydrogen atom.
• R 2a in the general formula (Ia) represents an alkyl group or a hydrogen atom having 1 to 8 carbon atoms.
• alkyl group having 1 to 8 carbon atoms examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, and a pentyl group.
• Neopentyl group isopentyl group, 1-ethylpropyl group, hexyl group, isohexyl group, 1,1-dimethylbutyl group, 2,2-dimethylbutyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group , Octyl group and the like, preferably methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group, and more preferably methyl group and ethyl group.
• a propyl group and an isopropyl group and particularly preferably a methyl group and an ethyl group.
• the number of carbon atoms of the alkyl group is preferably 1 to 6, more preferably 1 to 5, still more preferably 1 to 4, and particularly preferably 1 to 3.
• R 2a is preferably an alkyl group or a hydrogen atom having 1 to 6 carbon atoms, more preferably an alkyl group or a hydrogen atom having 1 to 4 carbon atoms, and further preferably a methyl group or an ethyl group.
• the suitable compound (Ia) is shown below.
• Ring A is a 5- or 6-membered saturated or unsaturated carbon ring; R 1a is an oxo group, a hydroxy group or a hydrogen atom; Compound (Ia), wherein R 2a represents an alkyl group or a hydrogen atom having 1 to 6 carbon atoms (preferably 1 to 4).
• Ring A is a 5- or 6-membered saturated or unsaturated oxygen-containing heterocycle; R 1a is an oxo group, a hydroxy group or a hydrogen atom; Compound (Ia), wherein R 2a represents an alkyl group or a hydrogen atom having 1 to 6 carbon atoms (preferably 1 to 4).
• Ring A is a 5- or 6-membered saturated or unsaturated nitrogen-containing heterocycle; R 1a is a hydrogen atom; Compound (Ia), wherein R 2a represents an alkyl group or a hydrogen atom having 1 to 6 carbon atoms (preferably 1 to 4).
• the part represented by is selected from the following;
• R 1a is an oxo group, a hydroxy group or a hydrogen atom;
• the part represented by is selected from the following;
• R 1a is an oxo group, a hydroxy group or a hydrogen atom;
• R 1a is an oxo group, a hydroxy group or a hydrogen atom (preferably a hydroxy group or a hydrogen atom);
• R 2a represents an alkyl group or a hydrogen atom having 1 to 6 carbon atoms (preferably 1 to 4)].
• R 1a is an oxo group, a hydroxy group or a hydrogen atom
• R 2a represents an alkyl group or a hydrogen atom having 1 to 6 carbon atoms (preferably 1 to 4)].
• R 1a is an oxo group, a hydroxy group or a hydrogen atom
• R 2a represents an alkyl group or a hydrogen atom having 1 to 6 carbon atoms (preferably 1 to 4)].
• R 2a represents an alkyl group or a hydrogen atom having 1 to 6 carbon atoms (preferably 1 to 4)].
• R 1a is an oxo group, a hydroxy group or a hydrogen atom (preferably a hydroxy group or a hydrogen atom);
• R 2a represents an alkyl group or a hydrogen atom having 1 to 6 carbon atoms (preferably 1 to 4)].
• Suitable compound (I) include Cycloten (CAS Registry Number is 80-71-7):
• cycloten ⁇ -butyrolactone, 2-methyltetrahydrofuran-3-one, ⁇ -angelicalactone, maltor, 3-methyl-1,2-cyclohexanedione, ⁇ - Dodecalactone, 5-dodecanolide, 4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one, D-camper are preferred, and cycloten is particularly preferred.
• the production method of (A) is not particularly limited, and a method known per se (for example, a chemical synthesis method, an enzyme method, a fermentation method, an extraction method, etc.) or a method similar thereto may be used.
• cycloten-related compounds are extracted from plants such as coffee beans (MA. Gianturco, AS. Giammarino, RG Pitcher, Tetrahedron 19 2051 (1963)), and high-temperature treatment of wood (J. Meyerfeld, Chem. Zt. 36 549 (1912)) or thermoalkaline treatment (T. Enkvist, B. Alfredson, M. Merikallio, P. Paakonen, O. Jarrella, Acta. Chem. Sand. 8 51 (1954), international sugar treatment.
• Component (B) The ⁇ -caryophyllene oxide used as (B) in the present invention is represented by the following formula, and its CAS Registry Number is 1139-30-6.
• the production method of (B) is not particularly limited, and a method known per se (for example, a chemical synthesis method, an enzyme method, a fermentation method, an extraction method, etc.) or a method similar thereto may be used.
• a commercially available product may be used.
• Component (C) The compound represented by the general formula (II) used as (C) in the present invention may be referred to as "Compound (II)" in the present specification.
• Compound (II) each group of the general formula (II) will be described.
• the "acyl group having 1 to 6 carbon atoms" may be linear or may have a branch, but is preferably linear.
• the acyl group may be saturated or may contain an unsaturated bond.
• 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, a hexanoyl group and the like.
• the "acyloxy group having 1 to 6 carbon atoms" may be linear or may have a branch, but is preferably linear.
• the acyl group may be saturated or may contain an unsaturated bond.
• Specific examples of the acyl group having 1 to 6 carbon atoms include a formyloxy group, an acetoxy group, a propionyloxy group, a butyryloxy group, an isobutyryloxy group, a valeryloxy group, an isovaleryloxy group, a pivaloyloxy group and a hexanoyloxy group. The group etc. can be mentioned.
• alkylene group having 1 to 6 carbon atoms may be linear or may have a branch, but is preferably linear.
• 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, a hexamethylene group and the like.
• R 3 in the general formula (II) represents an acyl group having 1 to 6 carbon atoms, a hydroxy group, a pyrrole group, or an acyloxy group having 1 to 6 carbon atoms.
• acyl group having 1 to 6 carbon atoms include formyl group, acetyl group, propionyl group, butyryl group, isobutyryl group, valeryl group, isovaleryl group, pivaloyl group, hexanoyl group and the like. It is 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.
• the number of carbon atoms of the acyl group is preferably 1 to 4.
• acyloxy group having 1 to 6 carbon atoms include formyloxy group, acetoxy group, propionyloxy group, butyryloxy group, isobutyryloxy group, valeryloxy group, isovaleryloxy group, and pivaloyloxy.
• examples thereof include a group, a hexanoyloxy group, and the like, preferably a formyloxy group, an acetoxy group, a propionyloxy group, a butyryloxy group, and an isobutyryloxy group, and more preferably a formyloxy group, an acetoxy group, and a propionyloxy group.
• the number of carbon atoms of the acyloxy group is preferably 1 to 4.
• R 3 in the general formula (II) is preferably an acyl group having 1 to 4 carbon atoms, a hydroxy group, a pyrrole group or an acyloxy group having 1 to 4 carbon atoms, and more preferably a formyl group or an acetyl group.
• Z in the general formula (II) indicates a single bond or an alkylene group having 1 to 6 carbon atoms.
• alkylene group having 1 to 6 carbon atoms examples include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group and the like, and a methylene group and an ethylene group are preferable. It is a group, a trimethylene group or a tetramethylene group, more preferably a methylene group or an ethylene group, and particularly preferably a methylene group.
• the number of carbon atoms of the alkylene group is preferably 1 to 4.
• Z in the general formula (II) 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.
• R 3 is an acyl group having 1 to 6 carbon atoms and Z is a single bond; R 3 is an acyl group having 1 to 4 carbon atoms. It is more preferable that the group is a group and Z is a single bond; it is particularly preferable that R 3 is a formyl group or an acetyl group and Z is a single bond.
• R 3 is a hydroxy group, a pyrrole group or an acyloxy group having 1 to 6 carbon atoms, and Z is an alkylene group having 1 to 6 carbon atoms.
• R 3 is a hydroxy group, a pyrrole group or an acyloxy group having 1 to 4 carbon atoms, and Z is an alkylene group having 1 to 4 carbon atoms; R 3 is hydroxy. It is particularly preferable that the group is a pyrrole group or a propionyloxy group, and Z is a methylene group.
• R4 in the general formula (II) represents a substituent.
• the substituent in R4 is not particularly limited, but is, for example, an alkyl group having 1 to 6 carbon atoms (eg, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, etc.) and a carbon atom.
• Cycloalkyl group of number 3-8 (eg, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, etc.), alkenyl group of 2-6 carbon atoms (eg, ethenyl group, 1-propenyl group, etc.) 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, etc.), alkynyl group having 2 to 6 carbon atoms (eg, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group) Group, 2-butynyl group, 3-butynyl group, etc.), acyl group with 1 to 6 carbon atoms (eg, formyl group, acetyl group, propionyl group, butyryl group, isobutyryl group, etc.), carbon atom number 1 to 6 An al
• alkyl group having 1 to 6 carbon atoms preferably an alkyl group having 1 to 6 carbon atoms and a hydroxyalkyl group having 1 to 6 carbon atoms. It is a group, more preferably an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, and particularly preferably a methyl group or a hydroxymethyl group.
• M in the general formula (II) indicates an integer of 0 to 3.
• m preferably represents an integer of 0 to 2, and more preferably 0 or 1.
• the plurality of R4s may be the same or different.
• R 3 is a formyl group, an acetyl group, a hydroxy group, a pyrrole group or a propionyloxy group; Z is a single bond or a methylene group; R4 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms); Compound (II) in which m represents an integer of 0 to 3.
• R 3 is a formyl group, an acetyl group, a hydroxy group, a pyrrole group or a propionyloxy group; Z is a single bond or a methylene group; R4 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms); Compound (II) in which m represents 0 or 1.
• R 3 is an acyl group or a hydroxy group having 1 to 6 carbon atoms
• Z is a single bond or an alkylene group having 1 to 6 carbon atoms
• R4 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms);
• R 3 is a formyl group, an acetyl group or a hydroxy group; Z is a single bond or a methylene group; R4 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms); Compound (II) in which m represents an integer of 0 to 3.
• R 3 is a formyl group, an acetyl group or a hydroxy group; Z is a single bond or a methylene group; R4 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms); Compound (II) in which m represents 0 or 1.
• R 3 is an acyl group or a pyrrole group having 1 to 6 carbon atoms; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R4 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms); Compound (II) in which m represents an integer of 0 to 3.
• R 3 is a formyl group, an acetyl group or a pyrrole group; Z is a single bond or a methylene group; R4 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms); Compound (II) in which m represents an integer of 0 to 3 (preferably 0 or 1).
• R 3 is a formyl group, an acetyl group or a pyrrole group; Z is a single bond or a methylene group; R4 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms); Compound (II) in which m represents 0 or 1.
• R 3 is an acyl group having 1 to 6 carbon atoms or an acyloxy group having 1 to 6 carbon atoms
• Z is a single bond or an alkylene group having 1 to 6 carbon atoms
• R4 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms);
• R 3 is a formyl group, an acetyl group or a propionyloxy group; Z is a single bond or a methylene group; R4 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms); Compound (II) in which m represents an integer of 0 to 3 (preferably 0 or 1).
• R 3 is a formyl group, an acetyl group or a propionyloxy group; Z is a single bond or a methylene group; R4 is a substituent (preferably an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms); Compound (II) in which m represents 0 or 1.
• Suitable compound (II) include Furfural (CAS Registry Number: 98-01-1):
• Furfuryl alcohol (CAS Registry Number: 98-00-0):
• furfural is preferable because it can effectively enhance the feeling of mouse coating.
• the production method of (C) is not particularly limited, and a method known per se (for example, a chemical synthesis method, an enzyme method, a fermentation method, an extraction method, etc.) or a method similar thereto may be used.
• a commercially available product may be used for (C).
• (A), (B) and (C) are, in one embodiment, a chemically synthesized product produced by a chemical synthesis method, respectively, or at least one compound selected from (A), (B) and (C). It may be an isolated product extracted and purified from a material containing. Examples of the material containing at least one of (A), (B) and (C) include natural products such as agricultural, livestock and fishery products (eg, maple, walnut, black pepper, white pepper, flower pepper, molasses, etc.).
• Culture solution obtained by culturing microorganisms, fermented products such as bacterial cells; and processed products thereof (For example, smoke agent, caramel sauce, wine, processed sugar cane, brown sugar, wasanbon sugar, sanon tou, molasses, coffee beans, coffee, spice extract, etc.) and the like.
• the present invention substitutes for the chemically synthesized product or isolated product of (A), (B) or (C), or in addition to the chemically synthesized product or isolated product, (A), (B) and A material containing at least one compound selected from (C) may be used as it is or after being purified to a desired degree.
• the amounts of (A), (B) and (C) contained in the material containing at least one compound selected from (A), (B) and (C) are gas chromatograph-mass spectrometry. It is measured by a meter (GC-MS) or the like.
• At least two compounds selected from the group consisting of (A), (B) and (C) contained in the composition of the present invention may be any of the following (i) to (xviii).
• (V) At least two compounds selected from the group consisting of (A) maltol, (B) ⁇ -caryophyllene oxide and (C) furfural (preferably all three compounds).
• (Ix) At least two compounds selected from the group consisting of (A) 4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one, (B) ⁇ -caryophyllene oxide and (C) furfural. (Preferably all three compounds) At least two compounds selected from the group consisting of (x) (A) D-camphor, (B) ⁇ -caryophyllene oxide and (C) furfural (preferably all three compounds). At least two compounds selected from the group consisting of (xi) (A) cycloten, (B) ⁇ -caryophyllene oxide and (C) 2-acetylfuran (preferably all three compounds).
• composition of the present invention may contain at least two compounds selected from the group consisting of (A) cycloten, (B) ⁇ -caryophyllene oxide and (C) furfural. Further, the composition of the present invention may contain (A) cycloten, (B) ⁇ -caryophyllene oxide and (C) furfural.
• the content of (A) in the composition of the present invention is usually 0.001% by weight or more, preferably 0, based on the composition of the present invention. It is 0.01% by weight or more, more preferably 0.1% by weight or more, further preferably 1% by weight or more, and particularly preferably 10% by weight or more.
• the content of (A) in the composition of the present invention is usually 99% by weight or less, preferably 95% by weight, based on the composition of the present invention. It is 0% by weight or less, more preferably 90% by weight or less.
• the content of (A) in the composition of the present invention is, in one aspect, usually 0.001 to 99% by weight based on the composition of the present invention. Yes, preferably 0.01 to 95% by weight, more preferably 0.1 to 90% by weight.
• the content of (B) in the composition of the present invention is usually 0.001% by weight or more, preferably 0, based on the composition of the present invention. It is 0.01% by weight or more, more preferably 0.1% by weight or more, further preferably 1% by weight or more, and particularly preferably 10% by weight or more.
• the content of (B) in the composition of the present invention is usually 99% by weight or less, preferably 95% by weight, based on the composition of the present invention. It is 0% by weight or less, more preferably 90% by weight or less.
• the content of (B) in the composition of the present invention is, in one aspect, usually 0.001 to 99% by weight based on the composition of the present invention. Yes, preferably 0.01 to 95% by weight, more preferably 0.1 to 90% by weight.
• the content of (C) in the composition of the present invention is usually 0.001% by weight or more, preferably 0, based on the composition of the present invention. It is 0.01% by weight or more, more preferably 0.1% by weight or more, further preferably 1% by weight or more, and particularly preferably 10% by weight or more.
• the content of (C) in the composition of the present invention is usually 99% by weight or less, preferably 95% by weight, based on the composition of the present invention. It is 0% by weight or less, more preferably 90% by weight or less.
• the content of (C) in the composition of the present invention is, in one aspect, usually 0.001 to 99% by weight based on the composition of the present invention. Yes, preferably 0.01 to 95% by weight, more preferably 0.1 to 90% by weight.
• the weight ratio (A: B) of the content of (A) to the content of (B) in the composition of the present invention is particularly high. It is preferably 1: 0.001 to 1000, more preferably 1: 0.5 to 1000, and even more preferably 1: 1 to 500, because it can effectively enhance the feeling of mouse coating. It is more preferably 1:10 to 250, particularly preferably 1:25 to 100, and most preferably 1:30 to 75.
• the weight ratio (A: C) of the content of (A) to the content of (C) in the composition of the present invention is particularly high. It is preferably 1: 0.001 to 1000, more preferably 1: 0.5 to 1000, and even more preferably 1: 1 to 500, because it can effectively enhance the feeling of mouse coating. It is more preferably 1:10 to 250, particularly preferably 1:25 to 100, and most preferably 1:30 to 75.
• the weight ratio (B: C) of the content of (B) to the content of (C) in the composition of the present invention is particularly high. It is preferably 1: 0.001 to 1000, more preferably 1: 0.01 to 100, and even more preferably 1: 0.02 to 50, because it can effectively enhance the feeling of mouse coating. Particularly preferably, it is 1: 0.3 to 3, and most preferably 1: 0.5 to 2.
• composition of the present invention may contain all of (A), (B) and (C) as one aspect.
• composition of the present invention is not particularly limited, and examples thereof include solid (including powder, granule, etc.), liquid (including slurry, etc.), gel, paste, and the like.
• composition of the present invention may consist of only at least two compounds selected from (A), (B) and (C), but in addition to these, in the form of the composition of the present invention and the like. It may further contain a suitable conventional base.
• the base when the composition of the present invention is in the form of a liquid examples include water, ethanol, glycerin, propylene glycol, various animal and vegetable oils, and the like.
• the base may be, for example, various sugars such as starch, dextrin, cyclodextrin, sucrose and glucose, proteins, peptides, salt, solid fat, silicon dioxide, and the like. Examples thereof include mixtures, yeast cells and various powder extracts.
• composition of the present invention in addition to at least two compounds selected from (A), (B) and (C), is described, for example, as an excipient, a pH adjuster, and an oxidation, as long as the object of the present invention is not impaired. It may further contain an inhibitor, a thickening stabilizer, a sweetener (eg, sugars, etc.), an acidulant, a spice, a coloring agent, and the like.
• composition of the present invention can be produced by a method commonly used in the field of food flavors.
• the composition of the present invention may be subjected to, for example, concentration treatment, drying treatment, decolorization treatment, etc., alone or in combination.
• the composition of the present invention can be added to foods and used. By adding the composition of the present invention to a food, the mouse coating feeling of the food can be enhanced. In addition, by adding the composition of the present invention to a food, the mouse coating feeling can be enhanced without imparting a strange flavor to the food. Therefore, the composition of the present invention can be suitably used as a perfume composition for enhancing the mouse coating feeling of foods.
• the "mouse coating sensation" is a sensation that the oral cavity is covered with a thin film, which is noticeably felt when a solution or food containing fat or oil is contained in the oral cavity, and the oral cavity is oily or fat-like.
• “Enhancement” of the mouse coating sensation means that at least one of the above sensations is enhanced.
• the presence or absence and degree of mouse coating feeling can be evaluated by sensory evaluation by a specialized panel.
• the "unusual flavor” refers to an unpleasant flavor (taste, aroma) that is not normally felt in foods.
• a different flavor to a food for example, when a specific unfavorable taste or aroma (eg, chemical odor, etc.) is imparted by adding a component that is not originally contained in the food, Examples thereof include cases where the original taste and aroma of foods change in an unfavorable manner.
• the presence or absence and degree of off-flavor can be evaluated by sensory evaluation by a specialized panel.
• "food” is a concept that broadly includes foods that can be ingested orally, and also includes, for example, beverages, seasonings, food additives, and the like.
• the food to which the composition of the present invention can be added may be originally provided (sold, distributed) in a state suitable for eating, or may be subjected to predetermined treatment or cooking to be in a state suitable for eating. It may be provided in the required condition.
• the food to which the composition of the present invention can be added may be provided as a concentrate or the like that needs to be diluted with water or the like in order to be in a state suitable for eating.
• the food to which the composition of the present invention can be added is not particularly limited as long as it can be desired to have a mouth-coated feeling, and for example, fats and oils (eg, vegetable fats and oils, animal fats and oils, etc.), mayonnaise, soup (eg, etc.).
• fats and oils eg, vegetable fats and oils, animal fats and oils, etc.
• mayonnaise e.g., soup, etc.
• composition of the present invention can remarkably enhance the mouse coating feeling felt when fats and oils are contained in the oral cavity, it is preferable that the composition of the present invention is added to foods containing fats and oils, that is, the composition of the present invention is used. , Preferably for fat-containing foods.
• the oil and fat contained in the oil and fat-containing food to which the composition of the present invention can be used is not particularly limited as long as it is edible, and for example, rapeseed oil, corn oil, soybean oil, sesame oil, rice oil, bran oil, red flower oil, palm oil, etc.
• Vegetable fats and oils such as palm oil, palm kernel oil, sunflower oil, sesame oil, sesame oil, flaxseed oil, olive oil, grape seed oil, medium chain fatty acid oil; pork fat (lard), beef fat, chicken oil, sheep fat, horse fat , Fish oil, whale oil, animal fats and oils such as milk fat and the like.
• transesterified oil obtained by transesterifying the above-mentioned fat and oil hydrogenated cured oil obtained by hydrogenating the above-mentioned fat and oil, and the like can also be used.
• the above-mentioned fats and oils may be refined (eg, salad oil, etc.). These fats and oils may be used alone or in combination of two or more.
• the content of fats and oils in the fats and oils-containing foods to which the composition of the present invention can be used is not particularly limited, but is preferably 0.1 to 100% by weight, more preferably 0.5, because the effect can be more clearly exhibited. ⁇ 100% by weight.
• the method and conditions for adding the composition of the present invention to the food are not particularly limited, and can be appropriately set according to the form of the composition of the present invention, the type of food, and the like.
• the time when the composition of the present invention is added to the food is not particularly limited and may be added at any time. For example, during the production of the food, after the completion of the food (immediately before eating the food, during eating the food, etc.), etc. Can be mentioned.
• the composition of the present invention may be added to the raw material before producing the food.
• the composition of the present invention contains at least (A)
• the composition of the present invention can effectively enhance the mouth coating feeling without imparting an offensive flavor to the food, and therefore, the composition of (A) in the food.
• the concentration (which may be referred to as "a” or “concentration a of (A)” in the present specification) is added to the food so as to be in a specific range with respect to the total weight of the food when eaten. Is preferable.
• the concentration a of (A) in the food is preferably 0.05 weight ppb or more, more preferably 0.1 weight ppb or more, and particularly, with respect to the total weight of the food at the time of eating. It is preferably 0.3 weight ppb or more.
• the concentration a of (A) in the food is preferably 5000 weight ppb or less, more preferably 3000 weight ppb or less, and particularly preferably 1500 weight ppb or less with respect to the total weight of the food at the time of eating.
• the concentration a of (A) in the food is, in one aspect, preferably 0.05 to 5000 weight ppb, more preferably 0.1 to 3000 weight ppb, based on the total weight of the food at the time of eating. Particularly preferably, it is 0.3 to 1500 weight ppb.
• the composition of the present invention contains at least (B)
• the composition of the present invention can effectively enhance the mouth coating feeling without imparting an off-flavor to the food, and therefore, the composition of (B) in the food.
• the concentration (which may be referred to as "b” or “concentration b of (B)” in the present specification) is added to the food so as to be in a specific range with respect to the total weight of the food when eaten. Is preferable.
• the concentration b of (B) in the food is preferably 0.1 weight ppb or more, more preferably 0.5 weight ppb or more, and particularly, with respect to the total weight of the food at the time of eating. It is preferably 1 weight ppb or more.
• the concentration b of (B) in the food is preferably 50,000 weight ppb or less, more preferably 10,000 weight ppb or less, and further preferably 7,000 weight ppb or less with respect to the total weight of the food at the time of eating. Yes, particularly preferably 6000 weight ppb or less.
• the concentration b of (B) in the food is, in one aspect, preferably 0.1 to 50,000 by weight ppb, more preferably 0.5 to 10,000 by weight ppb, based on the total weight of the food when eaten. Particularly preferably, it is 1 to 6000 weight ppb.
• the composition of the present invention can effectively enhance the mouth coating feeling without imparting an offensive flavor to the food, and therefore, the composition of (C) in the food.
• the concentration (which may be referred to as “c” or “concentration c of (C)” in the present specification) is added to the food so as to be in a specific range with respect to the total weight of the food when eaten. Is preferable.
• the concentration c of (C) in the food is preferably 0.1 weight ppb or more, more preferably 0.5 weight ppb or more, and particularly, with respect to the total weight of the food at the time of eating. It is preferably 1 weight ppb or more.
• the concentration c of (C) in the food is preferably 50,000 weight ppb or less, more preferably 10,000 weight ppb or less, and further preferably 7,000 weight ppb or less with respect to the total weight of the food at the time of eating. Yes, particularly preferably 6000 weight ppb or less.
• the concentration c of (C) in the food is, in one aspect, preferably 0.1 to 50,000 by weight ppb, more preferably 0.5 to 10,000 by weight ppb, based on the total weight of the food when eaten. Particularly preferably, it is 1 to 6000 weight ppb.
• the composition of the present invention can enhance the mouse coating feeling particularly effectively, and thus the concentration a of (A) in the food and ( It is preferable that the weight ratio (a: b) of B) to the concentration b is added to the food so as to be in a specific range.
• the weight ratio (a: b) of the concentration a of (A) to the concentration b of (B) in the food is preferably 1: 0.001 to 1000, and more preferably 1: 0. It is 5 to 1000, more preferably 1: 1 to 500, still more preferably 1:10 to 250, particularly preferably 1:25 to 100, and most preferably 1:30 to 75. ..
• the composition of the present invention can enhance the mouse coating feeling particularly effectively, and thus the concentration a of (A) in the food and ( It is preferable that the weight ratio (a: c) of C) to the concentration c is added to the food so as to be in a specific range.
• the weight ratio (a: c) of the concentration a of (A) to the concentration c of (C) in the food is preferably 1: 0.001 to 1000, and more preferably 1: 0. It is 5 to 1000, more preferably 1: 1 to 500, still more preferably 1:10 to 250, particularly preferably 1:25 to 100, and most preferably 1:30 to 75. ..
• the composition of the present invention can enhance the mouse coating feeling particularly effectively, so that the concentration b of (B) in the food and ( It is preferable that the weight ratio (b: c) of C) to the concentration c is added to the food so as to be in a specific range.
• the weight ratio (b: c) of the concentration b of (B) to the concentration c of (C) in the food is preferably 1: 0.001 to 1000, and more preferably 1: 0. It is 01 to 100, more preferably 1: 0.02 to 50, particularly preferably 1: 0.3 to 3, and most preferably 1: 0.5 to 2.
• the present invention is based on (A) general formula (I) :.
• Ring A is a 5- or 6-membered, saturated or unsaturated, carbocyclic or oxygen-containing or nitrogen-containing heterocycle;
• R 1 is an oxo group, a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an acyloxy group having 1 to 4 carbon atoms, a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, or a hydrocarbon group.
• R 1 is a hydrogen atom and R 1 is a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, the carbon atom in the hydrocarbon group is bonded to the carbon atom of the ring A.
• R2 is a hydrocarbon group, a hydroxy group or a hydrogen atom having 1 to 8 carbon atoms; n indicates an integer of 1 to 3]
• R 3 is an acyl group having 1 to 6 carbon atoms, a hydroxy group, a pyrrole group or an acyloxy group having 1 to 6 carbon atoms; Z is a single bond or an alkylene group having 1 to 6 carbon atoms; R4 is a substituent; m indicates an integer from 0 to 3] Also provided are foods (sometimes referred to simply as "foods of the invention” herein) containing at least two compounds selected from the group consisting of the compounds represented by.
• (A), (B) and (C) that can be contained in the food of the present invention are the same as (A), (B) and (C) that can be contained in the composition of the present invention, respectively, and preferred embodiments are also included. The same is true.
• At least two compounds selected from the group consisting of (A), (B) and (C) contained in the food of the present invention may be any of the above (i) to (xviii).
• the food product of the present invention may contain at least two compounds selected from the group consisting of (A) cycloten, (B) ⁇ -caryophyllene oxide and (C) furfural. Further, the food product of the present invention may contain (A) cycloten, (B) ⁇ -caryophyllene oxide and (C) furfural.
• the concentration of (A) in the food product of the present invention can be effectively enhanced because the food product of the present invention does not have an unusual flavor and the mouse coating feeling can be effectively enhanced.
• the concentration of (A) in the food product of the present invention can be set in the same manner as the concentration a of (A) described above, and the preferred range is also the same.
• the concentration of (B) in the food product of the present invention can be effectively enhanced because the food product of the present invention does not have an unusual flavor and the mouse coating feeling can be effectively enhanced.
• the concentration of (B) in the food product of the present invention can be set in the same manner as the concentration b of (B) described above, and the preferred range is also the same.
• the concentration of (C) in the food product of the present invention can be effectively enhanced because the food product of the present invention does not have an unusual flavor and the mouse coating feeling can be effectively enhanced.
• the concentration of (C) in the food product of the present invention can be set in the same manner as the concentration c of (C) described above, and the preferred range is also the same.
• the concentration of (A) and the concentration of (B) in the food product of the present invention can be enhanced.
• the weight ratio is preferably in a specific range. Specifically, the weight ratio of the concentration of (A) to the concentration of (B) in the food of the present invention is the weight ratio (a: b) of the above-mentioned concentration a of (A) and concentration b of (B). ), And the preferred range is also the same.
• the concentration of (A) and the concentration of (C) in the food product of the present invention can be enhanced.
• the weight ratio is preferably in a specific range. Specifically, the weight ratio of the concentration of (A) to the concentration of (C) in the food of the present invention is the weight ratio (a: c) of the above-mentioned concentration a of (A) and concentration c of (C). ), And the preferred range is also the same.
• the concentration of (B) and the concentration of (C) in the food product of the present invention can be enhanced.
• the weight ratio is preferably in a specific range. Specifically, the weight ratio of the concentration of (B) to the concentration of (C) in the food of the present invention is the weight ratio (b: c) of the concentration b of (B) and the concentration c of (C) described above. ), And the preferred range is also the same.
• the food of the present invention may contain all of (A), (B) and (C) as one aspect.
• the type of food of the present invention is not particularly limited as long as it can be desired to have a mouse-coated feeling, and examples thereof include foods similar to those exemplified as foods to which the composition of the present invention can be added. The same applies to preferred ones.
• the food of the present invention is preferably a food having an enhanced mouse coating feeling, and more preferably a food having an enhanced mouse coating feeling and no off-flavor.
• the food product of the present invention may contain fats and oils, that is, the food product of the present invention may be foods and fats containing fats and oils.
• the food product of the present invention may be an oil / fat-containing food having an enhanced mouse coating feeling, or may be an oil / fat-containing food having an enhanced mouse coating feeling and having no off-flavor.
• the fats and oils contained in the food of the present invention are not particularly limited as long as they are edible, but for example, the present invention.
• the fats and oils contained in the fats and oils-containing foods for which the composition of the above can be used include the same as those exemplified, and the preferred ones are also the same.
• the content of fats and oils in the food of the present invention is not particularly limited, but the effect can be more clearly exhibited. Therefore, it is preferably 0.1 to 99.9% by weight, more preferably 0.5 to 99.5% by weight.
• At least two compounds selected from the group consisting of (A), (B) and (C) added in the production method of the present invention may be any of the above (i) to (xviii).
• the production method of the present invention may include the addition of at least two compounds selected from the group consisting of (A) cycloten, (B) ⁇ -caryophyllene oxide and (C) furfural. Further, the production method of the present invention may include addition of (A) cycloten, (B) ⁇ -caryophyllene oxide and (C) furfural.
• the addition of (A) effectively enhances the mouse coating feeling and can produce a food having no off-flavor. It is preferable that the concentration of (A) in (A) is within a specific range with respect to the total weight of the food at the time of eating. Specifically, in the production method of the present invention, the concentration of (A) in the food can be set in the same manner as the concentration a of (A) described above, and the preferred range is also the same.
• the addition of (B) effectively enhances the mouse coating feeling and can produce a food having no off-flavor. It is preferable that the concentration of (B) in (B) is in a specific range with respect to the total weight of the food at the time of eating. Specifically, in the production method of the present invention, the concentration of (B) in the food can be set in the same manner as the above-mentioned concentration b of (B), and the preferable range is also the same.
• the addition of (C) effectively enhances the mouse coating feeling and can produce a food having no off-flavor. It is preferable that the concentration of (C) in (C) is in a specific range with respect to the total weight of the food at the time of eating. Specifically, in the production method of the present invention, the concentration of (C) in the food can be set in the same manner as the above-mentioned concentration c of (C), and the preferable range is also the same.
• the production method of the present invention comprises adding at least (A) and (B)
• the addition of (A) and (B) can produce a food having an enhanced mouse coating feeling particularly effectively. Therefore, it is preferable that the weight ratio of the concentration of (A) to the concentration of (B) in the food is within a specific range.
• the weight ratio of the concentration of (A) to the concentration of (B) in the food is the weight ratio of the above-mentioned concentration a of (A) and the concentration b of (B) ( It can be set in the same manner as in a: b), and the preferred range is also the same.
• the production method of the present invention comprises adding at least (A) and (C)
• the addition of (A) and (C) can produce a food with enhanced mouse coating feeling particularly effectively. Therefore, it is preferable that the weight ratio of the concentration of (A) to the concentration of (C) in the food is within a specific range.
• the weight ratio of the concentration of (A) to the concentration of (C) in the food is the weight ratio of the above-mentioned concentration a of (A) and the concentration c of (C) ( It can be set in the same manner as in a: c), and the preferred range is also the same.
• the production method of the present invention comprises adding at least (B) and (C)
• the addition of (B) and (C) can produce a food with enhanced mouse coating feeling particularly effectively. Therefore, it is preferable that the weight ratio of the concentration of (B) to the concentration of (C) in the food is within a specific range.
• the weight ratio of the concentration of (B) to the concentration of (C) in the food is the weight ratio of the above-mentioned concentration b of (B) and the concentration c of (C) ( b: It can be set in the same manner as in c), and the preferred range is also the same.
• At least two compounds selected from (A), (B) and (C) may be added individually, but these compounds are mixed in advance before addition to obtain a mixture. May be added. Alternatively, the addition of these compounds may be carried out using the compositions of the invention described above.
• the order and intervals of addition are not particularly limited, and for example, when (A) and (B) are added, (A), (B) may be added in the order of, or vice versa, and (A) and (B) may be added at the same time.
• the production method of the present invention may include, as one embodiment, adding all of (A), (B) and (C).
• a conventional processing step and cooking step in the production of food are produced. Etc. may be included as appropriate.
• the production method of the present invention is preferably a method for producing a food having an enhanced mouse coating feeling, and more preferably a method for producing a food having an enhanced mouse coating feeling and having no off-flavor.
• the production method of the present invention may be a method for producing an oil-containing food.
• the production method of the present invention may be a method for producing an oil / fat-containing food having an enhanced mouse coating feeling, or may be a method for producing an oil / fat-containing food having an enhanced mouse coating feeling and having no off-flavor. ..
• the present invention is based on (A) general formula (I) :.
• Ring A is a 5- or 6-membered, saturated or unsaturated, carbocyclic or oxygen-containing or nitrogen-containing heterocycle;
• R 1 is an oxo group, a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an acyloxy group having 1 to 4 carbon atoms, a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, or a hydrocarbon group.
• R 1 is a hydrogen atom and R 1 is a hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, the carbon atom in the hydrocarbon group is bonded to the carbon atom of the ring A.
• R2 is a hydrocarbon group, a hydroxy group or a hydrogen atom having 1 to 8 carbon atoms; n indicates an integer of 1 to 3]
• R 3 is an acyl group having 1 to 6 carbon atoms, a hydroxy group, a pyrrole group or an acyloxy group having 1 to 6 carbon atoms;
• Z is a single bond or an alkylene group having 1 to 6 carbon atoms;
• R4 is a substituent;
• m indicates an integer from 0 to 3]
• a method for enhancing the feeling of mouse coating which comprises adding at least two compounds selected from the group consisting of the compounds represented by Also provide.
• (A), (B) and (C) that can be used in the enhancing method of the present invention are the same as (A), (B) and (C) that can be contained in the composition of the present invention, respectively, and are preferred embodiments. Is the same.
• the enhancing method of the present invention can be carried out in the same manner as the above-mentioned manufacturing method of the present invention, and the preferred embodiment is also the same.
• the method and conditions for adding at least two compounds selected from (A), (B) and (C) are not particularly limited, and are appropriately depending on the type of food to which these are added and the like. Can be set.
• the time when at least two compounds selected from (A), (B) and (C) are added to the food is not particularly limited and may be added at any time, for example, during the production of the food and in the food. After completion (eg, just before eating food, while eating food, etc.). At least two compounds selected from (A), (B) and (C) may be added to the food material before producing the food.
• the mouse coating feeling of food can be effectively enhanced. Further, according to the enhancing method of the present invention, the mouse coating feeling can be effectively enhanced without imparting a strange flavor to the food.
• the food that can enhance the mouse coating feeling by the enhancing method of the present invention is not particularly limited as long as it can be desired to have a mouse coating feeling, and is exemplified as a food to which the composition of the present invention can be added. The same is true for the above, and the preferred one is also the same.
• the enhancing method of the present invention is preferably a method for enhancing the mouse coating feeling of foods containing fats and oils because it can remarkably enhance the mouse coating feeling felt when the fats and oils are contained in the oral cavity.
• Example 1 ⁇ Positive control and negative control> Normal commercially available mayonnaise (manufactured by Ajinomoto Co., Inc., trade name “Pure Select (registered trademark) mayonnaise", oil content: 73%) is used for positive control (PC), and positive for negative control (NC). Commercially available mayonnaise (manufactured by Ajinomoto Co., Inc., trade name “Pure Select (registered trademark) Kokuuma (registered trademark) 65% calorie cut", oil content: 23%) was used, which has a lower oil and fat content than the control mayonnaise.
• test sample was a commercially available mayonnaise (manufactured by Ajinomoto Co., Inc., trade name "Pure Select (registered trademark) Kokuuma (registered trademark) 65% calorie cut", fat content: 23%) used as the above-mentioned negative control, and cycloten.
• ⁇ -cariophyllene oxide and at least one compound selected from furfural were added so that the concentration of each compound in the food (mayonnaise) was the concentration shown in Tables 1 to 3 below (in each of the following, each).
• the test sample is also referred to as "sample of test group 1-1" to "sample of test group 1-39").
• Control area 1 Commercially available mayonnaise (manufactured by Ajinomoto Co., Inc., trade name "Pure Select (registered trademark) Kokuuma (registered trademark) 65% calorie cut", fat content: 23%) used as the above-mentioned negative control, cycloten, octanoic acid and Isovaleric acid was added so that the concentration of cycloten in the food (mayonnaise) was 100% by weight ppb, the concentration of octanoic acid was 200% by weight ppb, and the concentration of isovaleric acid was 100% by weight ppb to prepare a sample of control group 1. ..
• the four specialized panels were trained in advance so that the panel had a common understanding of how much the mouse coating feeling should fluctuate in order for the score to fluctuate by 0.1 points.
• four specialized panels eat each mayonnaise of the test sample and determine the presence or absence of the unusual flavor (taste and aroma that the mayonnaise does not originally have, such as chemical odor) based on the following criteria. It was decided by a consensus (non-blind). (Evaluation criteria for unusual flavor) ++: There is a strange flavor +: There is a slightly strange flavor-: There is no strange flavor
• Example 2 At least one compound selected from cycloten, ⁇ -cariophyllene oxide and furfural was added to a coffee beverage prepared using instant coffee powder, and a sensory evaluation was performed on the mouse coating feeling. Specifically, first, a coffee beverage was produced according to the formulation shown in Table 4 below using instant coffee powder, creaming powder, defatted milk powder, sugar and hot water spray-dried with hot water extract of roasted coffee beans. .. Commercially available products were used for creaming powder, skim milk powder, and sugar. Next, at least one compound selected from cycloten, ⁇ -cariophyllene oxide and furfural was added to the coffee beverage so that the concentration of each compound in the food (coffee beverage) would be the concentration shown in Table 5 below.
• test sample was prepared (hereinafter, referred to as "sample of test group 2-1" to “sample of test group 2-8", respectively).
• a coffee beverage (negative control) to which none of the compounds was added was set as "0.0 points”, and each test sample was prepared by three specialized panels based on the following criteria in the range of 0.0 to 5.0 points.
• Each test sample was prepared by three specialized panels based on the following criteria in the range of 0.0 to 5.0 points.
• the three specialized panels were trained in advance so that the panel had a common understanding of how much the mouse coating feeling should fluctuate in order for the score to fluctuate by 0.5 points.
• evaluation criteria for mouse coating feeling 5.0 points: Sufficient mouse coating feeling 2.5 points: Constant mouse coating feeling 1.0 points: Slightly mouse coating feeling
• any of the samples of Test Groups 2-4 to 2-8 of the present invention to which at least two compounds selected from the group consisting of cycloten, ⁇ -caryophyllene oxide and furfural were added.
• the feeling of mouse coating was effectively enhanced. No offensive flavor was confirmed in any of the samples in the test groups 2-1 to 2-8. From the results, it was confirmed that the mouse coating feeling can be effectively enhanced by adding at least two compounds selected from the group consisting of cycloten, ⁇ -caryophyllene oxide and furfural to foods.
• Example 3 At least one compound selected from cycloten, ⁇ -caryophyllene oxide and furfural was added to the instant noodles, and the mouse coating feeling was sensory evaluated. Specifically, first, instant noodles (manufactured by Toyo Suisan Kaisha, Ltd., trade name "Noodle making combined miso”: containing vegetable fats and oils and animal fats and oils (lard)) are prepared according to the instructions on the product packaging, and the instant noodles are prepared. At least one compound selected from cycloten, ⁇ -cariophyllene oxide and furfural was added to the soup category so that the concentration of each compound in the food (soup category) was the concentration shown in Table 6 below, and the test sample was added.
• sample of test group 3-1 to “sample of test group 3-10”
• the instant noodle soup (negative control) to which neither compound is added is set as “0.0 points", and in the range of 0.0 to 5.0 points, two specialized panels are each based on the following criteria. Test samples were scored in 0.5-point increments by consensus and sensory evaluation was performed. When the evaluation score was 1.0 or higher, it was determined that the mouse coating feeling was enhanced. The two specialized panels were trained in advance so that the panel had a common understanding of how much the mouse coating feeling should fluctuate in order for the score to fluctuate by 0.5 points. (Evaluation criteria for mouse coating feeling) 5.0 points: Sufficient mouse coating feeling 3.0 points: Constant mouse coating feeling 1.0 points: Slightly mouse coating feeling
• Example 4 At least one compound selected from cycloten, ⁇ -caryophyllene oxide and furfural was added to the instant noodles, and the mouse coating feeling was sensory evaluated. Specifically, first, prepare instant noodles (manufactured by Sanyo Foods Co., Ltd., product name "Sapporo Ichiban Miso Ramen Donburi”: containing vegetable oils and fats) according to the instructions on the product packaging, and then put them in the soup category of the instant noodles. At least one compound selected from cycloten, ⁇ -cariophyllene oxide and furfural was added so that the concentration of each compound in the food (soup category) was the concentration shown in Table 7 below to prepare a test sample ().
• sample of test group 4-1 to “sample of test group 4-10”, respectively).
• the instant noodle soup (negative control) to which neither compound is added is set as “0.0 points”, and in the range of 0.0 to 5.0 points, two specialized panels are each based on the following criteria. Test samples were scored in 0.5-point increments by consensus and sensory evaluation was performed. When the evaluation score was 1.0 or higher, it was determined that the mouse coating feeling was enhanced. The two specialized panels were trained in advance so that the panel had a common understanding of how much the mouse coating feeling should fluctuate in order for the score to fluctuate by 0.5 points. (Evaluation criteria for mouse coating feeling) 5.0 points: Sufficient mouse coating feeling 3.0 points: Constant mouse coating feeling 1.0 points: Slightly mouse coating feeling
• test groups 3-4 to 3-10 and tests of the present invention to which at least two compounds selected from the group consisting of cycloten, ⁇ -caryophyllene oxide and furfural were added.
• the feeling of mouse coating was effectively enhanced. No unusual flavor was confirmed in any of the samples in the test groups 3-1 to 3-10 and the test groups 4-1 to 4-10. From the results, it was confirmed that the mouse coating feeling can be effectively enhanced by adding at least two compounds selected from the group consisting of cycloten, ⁇ -caryophyllene oxide and furfural to foods.
• Example 5 ⁇ Positive control and negative control>
• the same commercially available mayonnaise as in Example 1 was used.
• test sample was prepared under the commercially available mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "Pure Select (registered trademark) Kokuuma (registered trademark) 65% calorie cut", oil content: 23%) used as the above-mentioned negative control.
• Compound (I) was added so that the concentration of compound (I) in the food (mayonnaise) was 10% by weight ppb, and ⁇ -cariophyllene oxide was added so that the concentration of ⁇ -cariophyllene oxide in the food (mayonnaise) was 500% by weight ppb.
• the flufural was added so that the concentration of the flufural in the food (mayonnaise) was 500 weight ppb.
• Example 6 ⁇ Positive control and negative control>
• the same commercially available mayonnaise as in Example 1 was used.
• test sample was prepared under the commercially available mayonnaise (manufactured by Ajinomoto Co., Ltd., trade name "Pure Select (registered trademark) Kokuuma (registered trademark) 65% calorie cut", oil content: 23%) used as the above-mentioned negative control.
• Compound (II) shown in Table 9 (furfural, 2-acetylfuran, 2-acetyl-5-methylfuran, 3-acetyl-2,5-dimethylfuran, furfuryl alcohol, 1-furfurylpyrrole, furfuryl propionate, It was prepared by adding at least one compound selected from 5-methylfurfural and 5- (hydroxymethyl) furfural), ⁇ -cariophyllene oxide and cycloten.
• Compound (II) was added so that the concentration of compound (II) in the food (mayonnaise) was 10% by weight ppb
• ⁇ -cariophyllene oxide was added so that the concentration of ⁇ -cariophyllene oxide in the food (mayonnaise) was 500% by weight ppb.
• Cycloten was added so that the concentration of cycloten in the food (mayonnaise) was 500% by weight ppb.
• Example 7 ⁇ Making instant noodles in control area 1> An aqueous solution obtained by dissolving 1.6 parts by weight of salt, 0.1 part by weight of potassium carbonate (food additive grade) and 0.1 part by weight of sodium carbonate (food additive grade) in 35 parts by weight of water (hereinafter). 36.8 parts by weight (referred to as “kneaded water”) was added to 100 parts by weight of wheat flour (quasi-strong flour) and kneaded for 5 minutes. The obtained noodle dough is made into a sheet (thickness: 1.3 ⁇ 0.1 mm) using an electric pasta machine (RM-220 manufactured by Imperia), both ends are cut off, and then the width is 1 mm and the length is 30 cm.
• RM-220 manufactured by Imperia electric pasta machine
• instant noodles were prepared by the same procedure as in the control group 1 except that cycloten and ⁇ -cariophyllene oxide were further dissolved in water in addition to salt, potassium carbonate and sodium carbonate (in the following, in the following, The instant noodles are referred to as "instant noodles in Test Zone 1").
• cycloten is used so that the concentration of cycloten in the prepared instant noodles is 376 weight ppb
• ⁇ -cariophyllene oxide is used so that the concentration of ⁇ -cariophyllen oxide in the prepared instant noodles is 18751 weight ppb. Was used for.
• ⁇ Making instant noodles in Test Zone 2> In the preparation of the kneaded water, instant noodles were prepared by the same procedure as in the control group 1 except that ⁇ -cariophyllene oxide and furfural were further dissolved in water in addition to salt, potassium carbonate and sodium carbonate (in the following, The instant noodles are referred to as "instant noodles in Test Zone 2").
• ⁇ -cariophyllene oxide is used so that the concentration of ⁇ -cariophyllene oxide in the prepared instant noodles is 18751 weight ppb
• furfural is used so that the concentration of furfural in the prepared instant noodles is 18751 weight ppb.
• instant noodles were prepared by the same procedure as in the control group 1 except that cycloten and furfural were further dissolved in water in addition to salt, potassium carbonate and sodium carbonate (hereinafter, the instant noodles). Is referred to as "instant noodles in test plot 3").
• cycloten was used so that the concentration of cycloten in the prepared instant noodles was 376 weight ppb
• furfural was used so that the concentration of furfural in the prepared instant noodles was 18751 weight ppb.
• instant noodles were prepared by the same procedure as in the control group 1 except that cycloten, ⁇ -cariophyllene oxide and furfural were further dissolved in water in addition to salt, potassium carbonate and sodium carbonate (hereinafter).
• the instant noodles are referred to as "instant noodles in Test Zone 4").
• cycloten is used so that the concentration of cycloten in the prepared instant noodles is 376 weight ppb
• ⁇ -cariophyllene oxide is used so that the concentration of ⁇ -cariophyllen oxide in the prepared instant noodles is 18751 weight ppb.
• the flufural was used so that the concentration of the fulfural in the prepared instant noodles was 18751 weight ppb.
• instant noodles were prepared by the same procedure as in the control group 1 except that cycloten, ⁇ -cariophyllene oxide and furfural were further dissolved in water in addition to salt, potassium carbonate and sodium carbonate (hereinafter).
• the instant noodles are referred to as "instant noodles in Test Zone 5").
• cycloten is used so that the concentration of cycloten in the prepared instant noodles is 470 weight ppb
• ⁇ -cariophyllene oxide is used so that the concentration of ⁇ -cariophyllen oxide in the prepared instant noodles is 23438 weight ppb.
• the flufural was used so that the concentration of the fulfural in the prepared instant noodles was 23438 weight ppb.
• instant noodles were prepared by the same procedure as in the control group 1 except that cycloten, ⁇ -cariophyllene oxide and furfural were further dissolved in water in addition to salt, potassium carbonate and sodium carbonate (hereinafter).
• the instant noodles are referred to as "instant noodles in Test Zone 6").
• cycloten is used so that the concentration of cycloten in the prepared instant noodles is 564 weight ppb
• ⁇ -cariophyllene oxide is used so that the concentration of ⁇ -cariophyllen oxide in the prepared instant noodles is 28126 weight ppb.
• the flufural was used so that the concentration of the fulfural in the prepared instant noodles was 28126 weight ppb.
• instant noodles were prepared by the same procedure as in the control group 1 except that furfural was further dissolved in water in addition to salt, potassium carbonate and sodium carbonate (in the following, the instant noodles are referred to as "instant noodles”. "Instant noodles in Comparative Zone 3").
• furfural was used so that the concentration of furfural in the prepared instant noodles was 18751 weight ppb.
• a fragrance composition capable of effectively enhancing the feeling of mouse coating.
• a perfume composition capable of effectively enhancing the mouse coating feeling without imparting a strange flavor to the food.
• a food having an effectively enhanced mouse coating feeling and a method for producing the same.
• a food product having no off-flavor and having an effectively enhanced mouse coating feeling and a method for producing the same.
• INDUSTRIAL APPLICABILITY According to the present invention, it is possible to provide a method capable of effectively enhancing the feeling of mouse coating. Further, according to the present invention, it is possible to provide a method capable of effectively enhancing the feeling of mouse coating without imparting a strange flavor to food.

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