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
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/20—Synthetic spices, flavouring agents or condiments

Definitions

• the present invention relates to a masking agent for unpleasant food odors.
• the present invention also relates to a method for masking unpleasant odors in food.
• the present invention relates to a method for producing food in which unpleasant odors are masked.
• Patent Document 1 For example, by including 2-furfuryl ethyl ether in liquid seasonings, the effect of masking off-flavors such as the animal odor of meat, the fishy odor of fish, the grassy odor of vegetables, and the milky odor of dairy products is improved (Patent Reference 1), by using a seasoning liquid for boiling containing this brewed soy sauce, sugars, salt and 4-hydroxy-2 (or 5) ethyl-5 (or 2) methyl-3 (2H) furanone, seafood or meat The fishy smell and retort smell can be reduced (Patent Document 2), and the fishy smell peculiar to fish can be masked by using soup stock containing catechins and thickening polysaccharides for cooking miso boiled fish (Patent Document 3).
• Patent Document 4 It has been reported that the unpleasant flavor caused by EPA/DHA can be reduced by adding a predetermined amount of protein to a liquid nutrient containing EPA/DHA (Patent Document 4). However, none of these methods provided a sufficient unpleasant odor masking effect.
• Patent Documents 5-7 do not describe an unpleasant odor masking effect.
• the present invention has been made in view of the above circumstances, and the problems to be solved are a masking agent capable of effectively masking the unpleasant odor of food, a method for masking the unpleasant odor of food, and a method for masking the unpleasant odor.
• the object is to provide a method for producing a prepared food.
• the present inventors found that a specific compound can effectively mask the unpleasant odor of food. Arrived. That is, the present invention is as follows.
• Masking agent for unpleasant food odors containing at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one .
• An unpleasant odor masking agent for food containing at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran and ⁇ -caryophyllene oxide.
• the food contains at least one raw material selected from the group consisting of meat raw materials, marine raw materials, plant raw materials, milk raw materials, yeast raw materials, fats and oils, egg raw materials and edible insects, or is retort food.
• Unpleasant food odors include bloody odor derived from meat raw materials, metallic odor derived from meat raw materials, animal odor derived from meat raw materials, lipid oxidation/deterioration odor derived from meat raw materials, visceral odor derived from meat raw materials, and meat raw materials.
• the masking agent according to [3], which is [5] The masking agent according to any one of [1] to [4], which is used in contact with food or its ingredients.
• the addition of the masking agent to the food or its raw material is carried out so that the amount of the compound added to the food or its raw material is 0.1 to 50000 ppb by weight with respect to the food. ]
• the addition of the masking agent to the food or its raw material is such that the amount of cyclotene added to the food or its raw material is 0.1 to 5000 ppb by weight of the food.
• the addition of the masking agent to the food or its raw material is such that the amount of propionic acid added to the food or its raw material is 1 to 50000 ppb by weight relative to the food.
• the addition of the masking agent to the food or its raw material is such that the amount of furfural added to the food or its raw material is 0.1 to 5000 ppb by weight relative to the food.
• the masking agent contains 2-acetylfuran the amount of 2-acetylfuran added to the food or its raw material is 0.00 to 0.000 to the food.
• the masking agent according to any one of [6] to [10] which is adjusted to 1 to 5000 weight ppb.
• the amount of ⁇ -caryophyllene oxide added to the food or its raw material is 1 to 1
• the masking agent contains 2-methyltetrahydrofuran-3-one
• the addition of the masking agent to the food or its ingredients is such that the amount of 2-methyltetrahydrofuran-3-one added to the food or its ingredients is .
• the concentration of ⁇ -caryophyllene oxide in the liquid containing the masking agent is 1 to 500000 ppb by weight relative to the liquid, [15] to [20] Masking agent according to any one of. [22] When the masking agent contains 2-methyltetrahydrofuran-3-one, the concentration of 2-methyltetrahydrofuran-3-one in the liquid containing the masking agent is 1 to 500000 ppb by weight relative to the liquid. , the masking agent according to any one of [15] to [21].
• the food contains at least one raw material selected from the group consisting of meat raw materials, marine raw materials, plant raw materials, milk raw materials, yeast raw materials, oils and fats, egg raw materials and edible insects, or is a retort food.
• Unpleasant food odors include bloody odor derived from meat raw materials, metallic odor derived from meat raw materials, animal odor derived from meat raw materials, lipid oxidation/deterioration odor derived from meat raw materials, visceral odor derived from meat raw materials, and meat raw materials.
• the food contains at least one raw material selected from the group consisting of meat raw materials, marine raw materials, plant raw materials, milk raw materials, yeast raw materials, oils and fats, egg raw materials and edible insects, or is a retort food.
• the amount of the compound added to the food or its raw material is 0.1 to 50,000 ppb by weight with respect to the food.
• the masking agent which can mask the unpleasant smell of food can be provided.
• the masking agent of the present invention can mask unpleasant odors without imparting flavor derived from its active ingredients to foods. Further, according to the present invention, it is possible to provide a method for masking an unpleasant odor of food and a method for producing food in which the unpleasant odor is masked.
• the masking agent for unpleasant food odor of the present invention (which may be referred to herein as the "masking agent of the present invention”) includes cyclotene, propionic acid, furfural, 2-acetylfuran, containing at least one compound selected from the group consisting of ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one (herein sometimes referred to as an “unpleasant odor masking compound”) as an active ingredient. , as one of the features.
• the term "food” broadly encompasses foods that can be taken orally, and includes so-called food, beverages, seasonings, supplements, and the like, unless otherwise specified. Food is a concept that also includes food compositions.
• the "unpleasant odor" of food refers to an odor that causes discomfort due to the raw materials, manufacturing process, etc. of the food. Visceral odor, grass odor, fishy odor, vegetable odor, grain odor, vegetable protein odor, amino acid odor, grassy odor, sulfur odor, insect odor, retort odor, steamy odor, and the like.
• "masking" an unpleasant odor means making the unpleasant odor partially or completely imperceptible.
• Cyclotene also commonly referred to as methylcyclopentenolone used as one of the unpleasant odor masking compounds in the present invention is a compound represented by the following formula (CAS registration number: 80-71-7).
• Propionic acid used as one of the unpleasant odor masking compounds in the present invention is a compound represented by CH 3 CH 2 COOH (CAS Registry Number: 79-09-4).
• Furfural which is used as one of the unpleasant odor masking compounds in the present invention, is a compound represented by the following formula (CAS registration number: 98-01-1).
• the 2-acetylfuran used as one of the unpleasant odor masking compounds in the present invention is a compound represented by the following formula (CAS registration number: 1192-62-7).
• the ⁇ -caryophyllene oxide used as one of the unpleasant odor masking compounds in the present invention is a compound represented by the following formula (CAS registration number: 1139-30-6).
• 2-methyltetrahydrofuran-3-one used as one of the unpleasant odor masking compounds in the present invention is a compound represented by the following formula (CAS registration number: 3188-00-9).
• Any one of the unpleasant odor masking compounds may be used alone, or two or more of them may be used. may be used in combination.
• the masking agent of the present invention may contain, as an active ingredient, at least one compound selected from the group consisting of propionic acid, furfural, 2-acetylfuran and ⁇ -caryophyllene oxide.
• the masking agent of the present invention may contain, as an active ingredient, at least one compound selected from the group consisting of cyclotene, propionic acid, 2-acetylfuran and ⁇ -caryophyllene oxide.
• the masking agent of the present invention may contain, as an active ingredient, at least one compound selected from the group consisting of cyclotene, propionic acid, furfural and 2-acetylfuran.
• the masking agent of the present invention may contain, as an active ingredient, at least one compound selected from the group consisting of propionic acid and 2-acetylfuran.
• the manufacturing method of the unpleasant odor masking compound is not particularly limited, and one manufactured by a method known per se (eg, chemical synthesis method, enzymatic method, fermentation method, extraction method, etc.) or a method equivalent thereto may be used.
• a commercial product may be used as the unpleasant odor masking compound.
• the unpleasant odor masking compound used in the present invention may be, as one aspect, a chemically synthesized product produced by a chemical synthesis method, or an isolated product extracted and purified from a material containing the unpleasant odor masking compound.
• Materials containing an unpleasant odor masking compound include, for example, natural products such as agricultural, livestock and fishery products; culture solutions obtained by culturing microorganisms, fermentation products such as fungal cells; and processed products thereof. be done.
• the present invention provides a material containing an unpleasant odor masking compound as it is or to a desired degree in place of a chemically synthesized product or isolated product of an unpleasant odor masking compound, or in addition to the chemically synthesized product or isolated product of the unpleasant odor masking compound. You may refine
• the content of unpleasant odor masking compounds in the material can be measured by gas chromatograph-mass spectrometer (GC-MS).
• the content of the unpleasant odor masking compound in the masking agent of the present invention is not particularly limited, but is generally 0.001% by weight or more, preferably 0.1% by weight or more, and particularly It is preferably 1% by weight or more.
• the amount is generally 100% by weight or less, preferably 99% by weight or less, more preferably 90% by weight or less, relative to the masking agent of the present invention.
• the form of the masking agent of the present invention is not particularly limited, and examples include solid (including powder, granule, etc.), liquid (including slurry, etc.), gel, paste, and the like.
• the masking agent of the present invention is only an unpleasant odor masking compound (at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one).
• it may further contain a conventional base.
• the base includes, for example, starch, dextrin, cyclodextrin, various sugars such as sucrose and glucose, proteins, peptides, salt, solid fats, silicon dioxide, and their Mixtures, yeast cells, various powder extracts, and the like can also be mentioned.
• examples of the base include water, ethanol, glycerin, propylene glycol, and various animal and vegetable oils.
• the masking agent of the present invention may be selected from the group consisting of unpleasant odor masking compounds (cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one) as long as the object of the present invention is not impaired.
• at least one selected compound for example, excipients, antioxidants, thickening stabilizers, emulsifiers, sweeteners (e.g., sugar, etc.), salt, organic salts, nucleic acids, seasonings (e.g., umami seasonings such as monosodium glutamate), acidifiers, coloring agents, coloring agents, and the like may be further contained.
• the masking agent of the present invention can be produced by a method known per se or a method equivalent thereto.
• the masking agent of the present invention is used in contact with foods having an unpleasant odor or raw materials thereof.
• Foods for which the masking agent of the present invention can be used are not particularly limited, but for example, at least one selected from the group consisting of meat raw materials, marine raw materials, plant raw materials, dairy raw materials, yeast raw materials, oils and fats, egg raw materials, and edible insects. as a raw material. Unpleasant odors that can be masked by the masking agent of the present invention may originate from the raw material.
• the "meat raw material” means livestock meat (e.g., pork, beef, horse meat, mutton, goat meat, rabbit meat, etc.), poultry meat (e.g., chicken, duck meat, turkey meat, etc.), or processed thereof.
• Food ingredients eg, ham, sausage, dried meat, etc. obtained by
• foods containing meat ingredients as raw materials include hamburgers, liver pastes, steaks, grilled meat, yakitori, braised pork, grilled pork, 1976uni, fried chicken, tonkatsu, sukiyaki, beef bowl, oyakodon, double pot meat, and green pepper.
• meat strings include, but are not limited to, meat strings, mapo tofu, curry, stew, ramen soup, seasonings (eg, flavor seasonings, yakiniku sauce, nabetsuyu, etc.).
• marine raw material refers to seafood (e.g., mackerel, tuna, bonito, sardines, cod, horse mackerel, yellowtail, sea bream, hoki, salmon and other fish; clams, scallops, abalone, tokobushi, surf clam, and other shellfish). ; squid, octopus, shrimp, crab, whale, etc.), algae (e.g., kelp, wakame seaweed, seaweed, hijiki, agaricus, Gracilaria, spirulina, etc.) or food materials obtained by processing these (e.g., dried fish, dried scallop) , frozen seafood, dried kelp, etc.).
• seafood e.g., mackerel, tuna, bonito, sardines, cod, horse mackerel, yellowtail, sea bream, hoki, salmon and other fish; clams, scallops, abalone, tokobushi, surf clam, and other shell
• foods containing marine raw materials as raw materials include grilled fish, fried fish, boiled food, dried fish, tempura, sushi, sashimi, salad, carpaccio, salted fish, ramen soup, seasonings (e.g., oyster sauce, fish sauce, flavor seasonings , nabetsuyu, etc.), but are not limited to these.
• seasonings e.g., oyster sauce, fish sauce, flavor seasonings , nabetsuyu, etc.
• plant material means vegetables (eg, cabbage, carrot, onion, etc.), grains (eg, wheat, barley, rye, rice, corn, etc.), fruits (eg, lemon, banana, mandarin orange, peach, etc.). ), beans (eg, soybeans, peas, broad beans, peanuts, etc.), potatoes, or food ingredients obtained by processing these (eg, vegetable proteins, etc.).
• the term "vegetable protein” refers to a protein-containing plant that has been processed to increase the protein content.
• specific examples of vegetable proteins include soybean protein, pea protein, faba protein, chickpea protein, almond protein, sunflower protein and the like.
• the form of the vegetable protein is not particularly limited, and may be, for example, in the form of powder, granules, fibers, paste, or the like.
• foods containing plant materials as raw materials include noodles (e.g., ramen, udon, soba, etc.), stir-fried vegetables, grilled vegetables, tempura, boiled beans, tofu, alternative meat foods, and beverages (e.g., coffee, alcoholic beverages). , non-alcoholic beverages, tea, soy milk, etc.), seasonings (eg, miso, soy sauce, sauces, dressings, flavor seasonings, etc.), etc., but are not limited thereto.
• noodles e.g., ramen, udon, soba, etc.
• stir-fried vegetables grilled vegetables, tempura, boiled beans, tofu
• alternative meat foods e.g., coffee, alcoholic beverages
• beverages e.g., coffee, alcoholic beverages
• non-alcoholic beverages e.g., tea, soy milk, etc.
• seasonings eg, miso, soy sauce, sauces, dressings, flavor seasonings, etc.
• "dairy raw material” means animal milk (e.g., raw milk, cow's milk, raw goat milk, pasteurized goat milk, raw sheep's milk, raw buffalo milk, etc.) or food raw materials obtained by processing this (e.g., cream, butter, butter oil, cheese, concentrated whey, ice creams, concentrated milk, whole milk powder, skimmed milk powder, cream powder, whey powder, fermented milk, lactic acid beverages, milk beverages, etc.).
• animal milk e.g., raw milk, cow's milk, raw goat milk, pasteurized goat milk, raw sheep's milk, raw buffalo milk, etc.
• food raw materials obtained by processing this e.g., cream, butter, butter oil, cheese, concentrated whey, ice creams, concentrated milk, whole milk powder, skimmed milk powder, cream powder, whey powder, fermented milk, lactic acid beverages, milk beverages, etc.
• foods containing dairy ingredients include, but are not limited to, milk drinks, cream soups, pizza, stews, seasonings (eg, cheese sauce, dressing, etc.).
• yeast raw material refers to edible yeast or food raw materials obtained by processing it (eg, yeast extract, etc.).
• foods containing yeast ingredients as ingredients include, but are not limited to, natural seasonings, flavor seasonings, and the like.
• fat and oil means edible fat and oil (e.g., canola oil, rapeseed oil, corn oil, soybean oil, sesame oil, rice oil, rice bran oil, rice germ oil, safflower oil, coconut oil, palm oil, palm kernel oil, sunflower oil, perilla oil, linseed oil, olive oil, grapeseed oil, beef tallow, lard, chicken fat, mutton fat, etc.) or food materials obtained by processing these (e.g., interesterified oil, hardened oil, etc.) .
• canola oil rapeseed oil, corn oil, soybean oil, sesame oil, rice oil, rice bran oil, rice germ oil, safflower oil, coconut oil, palm oil, palm kernel oil, sunflower oil, perilla oil, linseed oil, olive oil, grapeseed oil, beef tallow, lard, chicken fat, mutton fat, etc.
• food materials obtained by processing these e.g., interesterified oil, hardened oil, etc.
• oils and fats as raw materials
• foods containing oils and fats as raw materials include noodles, instant noodles, butter, margarine, curry roux, fried chicken, croquettes, snacks, seasonings (eg, nabetsuyu, dressings, mayonnaise, flavor seasonings, etc.).
• seasonings eg, nabetsuyu, dressings, mayonnaise, flavor seasonings, etc.
• egg raw materials refer to whole eggs, egg yolks, egg whites, or food raw materials obtained by processing these (eg, whole egg powder, egg yolk powder, egg white powder, enzyme-treated egg yolk, salted egg yolk, etc.).
• foods containing egg ingredients include fried eggs, egg soup, chawanmushi, puddings, seasonings (eg, mayonnaise, dressing, etc.), but are not limited to these.
• edible insects refers to edible insects (e.g., crickets, silkworms, locusts, honeycombs, moths, ants, grasshoppers, etc.) or food materials obtained by processing these (e.g., insect proteins, etc.).
• foods containing edible insects as raw materials include alternative meat foods (e.g., hamburger-like foods, meatball-like foods, nugget-like foods, etc.), beverages, seasonings (soy sauce, miso, flavor seasonings, etc.), Boiled foods, sweets and the like can be mentioned, but are not limited to these.
• alternative meat foods e.g., hamburger-like foods, meatball-like foods, nugget-like foods, etc.
• beverages e.g., seasonings (soy sauce, miso, flavor seasonings, etc.), Boiled foods, sweets and the like can be mentioned, but are not limited to these.
• retort food refers to food sealed in an airtight container or package and subjected to pressurized heat sterilization (retort treatment).
• retort treatment may be carried out by a method known per se or a method based thereon, and various treatment conditions, equipment to be used (retort sterilization equipment), containers and packaging of retort foods are not particularly limited.
• the method for producing food in which the masking agent of the present invention can be used is not particularly limited, and can be produced by a method known per se or a method equivalent thereto.
• the method of bringing the masking agent of the present invention into contact with food or raw materials thereof is not particularly limited.
• (1) adding the masking agent of the present invention to food or its raw materials It can be carried out by, for example, immersing the food or its raw material in the containing liquid.
• the method of addition is not particularly limited. mixing the masking agent of the present invention with raw materials; This can be done by dispersing a masking agent or the like.
• an unpleasant odor masking compound added to food or its raw material is preferably 0.1 weight ppb or more (more preferably 1 weight ppb or more, particularly preferably 5 weight ppb or more) with respect to the food.
• the masking agent of the present invention is added to the food or its ingredients from the viewpoint of obtaining a sufficient unpleasant odor masking effect without imparting the flavor derived from the unpleasant odor masking compound to the food.
• the amount of the masking compound is 50000 weight ppb or less (more preferably 20000 weight ppb or less, particularly preferably 15000 weight ppb or less) with respect to the food.
• the amount of the unpleasant odor masking compound added to food or its raw material is 0.1 to 50,000 weight ppb (more preferably 1 to 20,000 weight ppb, particularly Preferably, it is carried out so that the content is 5 to 15,000 weight ppb).
• the masking agent of the present invention contains cyclotene as an unpleasant odor masking compound, and the contact of the masking agent of the present invention with food or ingredients thereof is controlled by adding the masking agent of the present invention to food or ingredients thereof.
• the masking agent of the present invention is added by more preferably 1 weight ppb or more, still more preferably 5 weight ppb or more, particularly preferably 50 weight ppb or more).
• the addition of the masking agent of the present invention from the viewpoint of obtaining a sufficient unpleasant odor-masking effect without imparting the flavor derived from the unpleasant odor-masking compound to the food, reduces the amount of cyclotene added to the food or its ingredients.
• the amount is preferably 5000 weight ppb or less (more preferably 2000 weight ppb or less, particularly preferably 1500 weight ppb or less) with respect to the food.
• the amount of cyclotene added to the food or its raw material is 0.1 to 5000 weight ppb (more preferably 1 to 2000 weight ppb, particularly preferably 50 weight ppb) relative to the food. It is preferable to carry out so that it becomes ⁇ 1500 weight ppb).
• the masking agent of the present invention contains propionic acid as an unpleasant odor masking compound, and the contact of the masking agent of the present invention with food or ingredients thereof is controlled by adding the masking agent of the present invention to food or ingredients thereof.
• the amount of propionic acid added to the food or its raw material is 1 ppb or more by weight of the food ( more preferably 10 weight ppb or more, still more preferably 50 weight ppb or more, particularly preferably 500 weight ppb or more).
• the addition of the masking agent of the present invention is such that the amount of propionic acid added to the food or its raw material is , 50000 weight ppb or less (more preferably 20000 weight ppb or less, particularly preferably 15000 weight ppb or less) of the food.
• the amount of propionic acid added to food or its raw material is 1 to 50,000 weight ppb (more preferably 10 to 20,000 weight ppb, particularly preferably 500 to 500 weight ppb). 15000 weight ppb).
• the masking agent of the present invention contains furfural as an unpleasant odor masking compound, and the contact of the masking agent of the present invention with food or ingredients thereof is controlled by adding the masking agent of the present invention to food or ingredients thereof.
• the masking agent of the present invention is added by more preferably 1 weight ppb or more, still more preferably 5 weight ppb or more, particularly preferably 50 weight ppb or more).
• the addition of the masking agent of the present invention is from the viewpoint of masking the unpleasant odor without imparting the flavor derived from the unpleasant odor masking compound to the food.
• the food is 5000 weight ppb or less (more preferably 2000 weight ppb or less, particularly preferably 1500 weight ppb or less).
• the amount of furfural added to the food or its raw material is 0.1 to 5000 weight ppb (more preferably 1 to 2000 weight ppb, particularly preferably 50 It is preferable to carry out so that it becomes ⁇ 1500 weight ppb).
• the masking agent of the present invention contains 2-acetylfuran as an unpleasant odor masking compound, and contact of the masking agent of the present invention with food or raw materials thereof is controlled by contacting the masking agent of the present invention with food or raw materials thereof.
• the amount of 2-acetylfuran added to the food or its raw material is 0 from the viewpoint of obtaining a sufficient unpleasant odor masking effect. .1 weight ppb or more (more preferably 1 weight ppb or more, still more preferably 5 weight ppb or more, particularly preferably 50 weight ppb or more).
• the addition of the masking agent of the present invention is the addition of 2-acetylfuran added to the food or its raw material.
• the amount is preferably 5000 weight ppb or less (more preferably 2000 weight ppb or less, particularly preferably 1500 weight ppb or less) with respect to the food.
• the amount of 2-acetylfuran added to food or its raw material is 0.1 to 5000 weight ppb (more preferably 1 to 2000 weight ppb, particularly Preferably, it is carried out so that it becomes 50 to 1500 weight ppb).
• the masking agent of the present invention contains ⁇ -caryophyllene oxide as an unpleasant odor masking compound, and contact of the masking agent of the present invention with food or raw materials thereof is controlled by contacting the masking agent of the present invention with food or raw materials thereof.
• the amount of ⁇ -caryophyllene oxide added to the food or its raw material is 1, from the viewpoint of obtaining a sufficient unpleasant odor masking effect. It is preferable to carry out the weight ppb or more (more preferably 10 weight ppb or more, still more preferably 50 weight ppb or more, particularly preferably 500 weight ppb or more).
• addition of the masking agent of the present invention is one aspect from the viewpoint of masking the unpleasant odor without imparting the flavor derived from the unpleasant odor masking compound to the food.
• the amount of caryophyllene oxide is 5000 weight ppb or less (more preferably 2000 weight ppb or less, particularly preferably 1500 weight ppb or less) with respect to food, or as another aspect, food or
• the amount of ⁇ -caryophyllene oxide added to the raw material is preferably 50,000 weight ppb or less (more preferably 20,000 weight ppb or less, particularly preferably 15,000 weight ppb or less) of the food.
• one aspect of the addition of the masking agent of the present invention is that the amount of ⁇ -caryophyllene oxide added to the food or its raw material is 1 to 5000 weight ppb (more preferably 10 to 2000 weight ppb) relative to the food. , particularly preferably 500 to 1500 weight ppb), or as another aspect, the amount of ⁇ -caryophyllene oxide added to the food or its raw material is 1 to 50000 weight ppb relative to the food. ppb (more preferably 10 to 20,000 weight ppb, particularly preferably 500 to 15,000 weight ppb).
• the masking agent of the present invention contains 2-methyltetrahydrofuran-3-one as an unpleasant odor masking compound, and contact of the masking agent of the present invention with food or its ingredients is controlled by the masking agent of the present invention.
• the amount of 2-methyltetrahydrofuran-3-one added to the food or its raw material is adjusted from the viewpoint of obtaining a sufficient unpleasant odor masking effect.
• the content of the food is 0.1 weight ppb or more (more preferably 1 weight ppb or more, still more preferably 5 weight ppb or more, and particularly preferably 50 weight ppb or more).
• the addition of the masking agent of the present invention is effective from the viewpoint of masking the unpleasant odor without imparting the flavor derived from the unpleasant odor masking compound to the food, 2-methyltetrahydrofuran- It is preferable that the amount of 3-one is 5000 weight ppb or less (more preferably 2000 weight ppb or less, particularly preferably 1500 weight ppb or less) with respect to the food.
• the amount of 2-methyltetrahydrofuran-3-one added to the food or its raw material is 0.1 to 5000 weight ppb (more preferably 1 to 2000 ppb). ppb by weight, particularly preferably 50 to 1500 ppb by weight).
• the time (timing) for adding the masking agent of the present invention to the food or its raw material is not particularly limited, but examples include during the production of the food and after the production of the food.
• the masking agent of the present invention is brought into contact with food or its raw material by (2) immersing the food or its raw material in a liquid containing the masking agent of the present invention (hereinafter sometimes referred to as "masking liquid" for convenience).
• a liquid containing the masking agent of the present invention hereinafter sometimes referred to as "masking liquid” for convenience.
• the unpleasant odor masking compound at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one
• the concentration is preferably 0.1 weight ppb or more, more preferably 0.5 weight ppb or more, and particularly preferably 1 weight ppb or more with respect to the masking liquid, from the viewpoint of obtaining a sufficient unpleasant odor masking effect.
• the concentration is preferably 500000 weight ppb or less, more preferably 200000 weight ppb or less relative to the masking liquid, from the viewpoint of masking the unpleasant odor without imparting the flavor derived from the unpleasant odor masking compound to the food. and particularly preferably 150,000 weight ppb or less.
• the concentration is preferably 0.1 to 500,000 weight ppb, more preferably 0.5 to 200,000 weight ppb, and particularly preferably 1 to 150,000 weight ppb with respect to the masking liquid.
• the masking agent of the present invention contains cyclotene as an unpleasant odor masking compound, and the masking agent of the present invention is brought into contact with the food or its raw material by immersing the food or its raw material in the masking liquid.
• the concentration of cyclotene in the masking liquid is preferably 1 ppb or more by weight, more preferably 15 ppb or more by weight, and still more preferably It is 100 weight ppb or more, particularly preferably 1000 weight ppb or more.
• the concentration is preferably 10000 weight ppb or less, more preferably 5000 weight ppb or less relative to the masking liquid, from the viewpoint of masking the unpleasant odor without imparting the flavor derived from the unpleasant odor masking compound to the food. and particularly preferably 3000 weight ppb or less.
• the concentration is preferably 1 to 10000 weight ppb, more preferably 15 to 5000 weight ppb, particularly preferably 1000 to 3000 weight ppb, relative to the masking liquid.
• the masking agent of the present invention contains propionic acid as an unpleasant odor masking compound, and the masking agent of the present invention is brought into contact with food or its raw materials by immersing the food or its raw materials in the masking liquid.
• the concentration of propionic acid in the masking liquid is preferably 1 ppb by weight or more, more preferably 10 ppb by weight or more, and It is preferably 50 weight ppb or more, and particularly preferably 500 weight ppb or more.
• the concentration is preferably 500000 weight ppb or less, more preferably 200000 weight ppb or less relative to the masking liquid, from the viewpoint of masking the unpleasant odor without imparting the flavor derived from the unpleasant odor masking compound to the food. and particularly preferably 150,000 weight ppb or less.
• the concentration is preferably 1 to 500,000 weight ppb, more preferably 10 to 200,000 weight ppb, particularly preferably 500 to 150,000 weight ppb, relative to the masking liquid.
• the masking agent of the present invention contains furfural as an unpleasant odor masking compound, and the masking agent of the present invention is brought into contact with the food or its raw material by immersing the food or its raw material in the masking liquid.
• the concentration of furfural in the masking liquid is preferably 0.1 weight ppb or more, more preferably 0.5 weight ppb or more, relative to the masking liquid, from the viewpoint of obtaining a sufficient unpleasant odor masking effect. More preferably, it is 1 weight ppb or more, and particularly preferably 30 weight ppb or more.
• the concentration is preferably 20000 weight ppb or less, more preferably 10000 weight ppb or less with respect to the masking liquid, from the viewpoint of masking the unpleasant odor without imparting the flavor derived from the unpleasant odor masking compound to the food. and particularly preferably 7000 weight ppb or less.
• the concentration is preferably 0.1 to 20000 weight ppb, more preferably 0.5 to 10000 weight ppb, and particularly preferably 30 to 7000 weight ppb with respect to the masking liquid.
• the masking agent of the present invention contains 2-acetylfuran as an unpleasant odor masking compound, and the masking agent of the present invention is brought into contact with food or its raw material by immersing the food or its raw material in the masking liquid.
• the concentration of 2-acetylfuran in the masking liquid is preferably 1 ppb or more by weight, more preferably 10 ppb or more by weight, with respect to the masking liquid, from the viewpoint of obtaining a sufficient unpleasant odor masking effect. , more preferably 50 weight ppb or more, particularly preferably 8000 weight ppb or more.
• the concentration is preferably 500000 weight ppb or less, more preferably 200000 weight ppb or less relative to the masking liquid, from the viewpoint of masking the unpleasant odor without imparting the flavor derived from the unpleasant odor masking compound to the food. and particularly preferably 150,000 weight ppb or less.
• the concentration is preferably 1 to 500,000 weight ppb, more preferably 10 to 200,000 weight ppb, and particularly preferably 8,000 to 150,000 weight ppb with respect to the masking liquid.
• the masking agent of the present invention contains ⁇ -caryophyllene oxide as an unpleasant odor masking compound, and the masking agent of the present invention is brought into contact with the food or its raw material by immersing the food or its raw material in the masking liquid.
• the concentration of ⁇ -caryophyllene oxide in the masking liquid is preferably 1 ppb or more by weight, more preferably 10 ppb or more by weight, with respect to the masking liquid, from the viewpoint of obtaining a sufficient unpleasant odor masking effect. and particularly preferably 50 weight ppb or more.
• the concentration is preferably 500000 weight ppb or less, more preferably 200000 weight ppb or less relative to the masking liquid, from the viewpoint of masking the unpleasant odor without imparting the flavor derived from the unpleasant odor masking compound to the food. and particularly preferably 150,000 weight ppb or less.
• the concentration is preferably 1 to 500,000 weight ppb, more preferably 10 to 200,000 weight ppb, particularly preferably 50 to 150,000 weight ppb, relative to the masking liquid.
• the masking agent of the present invention contains 2-methyltetrahydrofuran-3-one as an unpleasant odor masking compound, and contact of the masking agent of the present invention with food or its raw materials is controlled by the masking liquid.
• the concentration of 2-methyltetrahydrofuran-3-one in the masking liquid is preferably 0.1 weight ppb or more with respect to the masking liquid from the viewpoint of obtaining a sufficient unpleasant odor masking effect. , more preferably 0.5 weight ppb or more, still more preferably 1 weight ppb or more, and particularly preferably 30 weight ppb or more.
• the concentration is preferably 20000 weight ppb or less, more preferably 10000 weight ppb or less with respect to the masking liquid, from the viewpoint of masking the unpleasant odor without imparting the flavor derived from the unpleasant odor masking compound to the food. and particularly preferably 7000 weight ppb or less.
• the concentration is preferably 0.1 to 20000 weight ppb, more preferably 0.5 to 10000 weight ppb, and particularly preferably 30 to 7000 weight ppb with respect to the masking liquid.
• the method of preparing the masking liquid is not particularly limited, and may be carried out by a method known per se or a method analogous thereto. For example, it can be prepared by dissolving in water, etc.).
• the masking liquid may contain, in addition to the masking agent and solvent (eg, water) of the present invention, other ingredients (eg, seasonings, etc.) as long as the object of the present invention is not impaired.
• the masking agent of the present invention when the masking agent of the present invention is in a liquid form, the masking agent of the present invention may be used as it is or diluted with water or the like as a masking liquid.
• the amount of masking liquid used is not particularly limited, but it is usually 10 to 500 parts by weight, preferably 15 to 500 parts by weight, per 100 parts by weight of the food or its raw material. 150 parts by weight.
• the time for which the food or its raw materials are immersed in the masking liquid is not particularly limited, but it is usually 10 minutes or more, preferably 1 hour or more.
• the timing of immersing the food or its ingredients in the masking liquid is not particularly limited, but includes, for example, during food production and after food production.
• the unpleasant odors that can be masked by the masking agent of the present invention are not particularly limited.
• the masking agent of the present invention can be suitably used to mask the unpleasant odor caused by the raw material.
• unpleasant odors caused by meat ingredients include bloody odors, metallic odors, animal odors, lipid oxidation/deterioration odors, visceral odors, and glass odors.
• the "fishy odor derived from meat raw materials” refers to the odor peculiar to the blood contained in the meat raw materials and the odor produced by the oxidation or enzymatic reaction of the blood contained in the meat raw materials.
• the “metallic odor derived from meat raw materials” refers to the odor peculiar to metals (e.g., iron, etc.) contained in meat raw materials and odors caused by changes in metals contained in meat raw materials. The origin of the iron odor, etc. are included.
• Examples of compounds that cause bloody odors derived from meat ingredients and metallic odors (eg, iron odors) derived from meat ingredients include 1-octen-3-ol and 1-penten-3-one.
• the "animal odor derived from meat raw materials" is an odor reminiscent of animals.
• Compounds that cause animal odors derived from meat ingredients include, for example, p-cresol, m-cresol, and 2,4-decadienal.
• the "lipid oxidation/deterioration odor derived from meat raw materials” is an odor caused by oxidation or deterioration of fat and oil components contained in meat raw materials.
• Examples of compounds that cause lipid oxidation/deterioration odors derived from meat ingredients include isovaleric acid, trans-2-nonenal, and 1-octen-3-ol.
• the "visceral odor derived from meat raw materials” refers to the odor peculiar to raw livestock or poultry internal organs, and the odor produced by oxidation or enzymatic reaction of livestock or poultry internal organs.
• Examples of compounds that cause visceral odor derived from meat ingredients include sulfur-containing compounds (eg, methional, hydrogen sulfide, methyl mercaptan, methyl sulfide, dimethyl mercaptan, ethyl mercaptan, dimethyl disulfide, sulfur dioxide, etc.).
• sulfur-containing compounds eg, methional, hydrogen sulfide, methyl mercaptan, methyl sulfide, dimethyl mercaptan, ethyl mercaptan, dimethyl disulfide, sulfur dioxide, etc.
• the "grass odor derived from meat ingredients” is an odor reminiscent of grass.
• Examples of compounds that cause grass odor derived from meat ingredients include volatile aldehydes (e.g., methanal (formaldehyde), ethanal (acetaldehyde), propanal (propionaldehyde), butanal, hexanal, octanal (caprylaldehyde), decanal (caprin aldehyde), 2-propenal (acrolein, acrylaldehyde), 2-butenal (crotonaldehyde), benzaldehyde, etc.).
• volatile aldehydes e.g., methanal (formaldehyde), ethanal (acetaldehyde), propanal (propionaldehyde), butanal, hexanal, octanal (caprylaldehyde), decanal (caprin aldehyde), 2-propenal (acrolein, acrylaldehyde), 2-butenal (crotonaldehyde
• unpleasant odors caused by marine raw materials include fishy odors, oxidized lipid odors, deterioration odors, and visceral odors.
• the "fishy odor derived from marine raw materials" is an odor peculiar to raw marine raw materials.
• Examples of fishy odor-causing compounds derived from marine raw materials include trimethylamine, triethylamine, ammonia, dimethylamine, ⁇ -aminovaleric acid, ⁇ -aminovaleral, and the like.
• the "lipid oxidation/deterioration odor derived from marine raw materials” is an odor caused by changes due to oxidation or deterioration of oil and fat components contained in marine raw materials.
• Examples of compounds that cause lipid oxidation/deterioration odors derived from marine raw materials include unsaturated fatty acids (e.g., docosahexaenoic acid, eicosapentaenoic acid, etc.) and their oxidation products, 3-methyl-1-butanol, pentadecane, and 1-pentene.
• unsaturated fatty acids e.g., docosahexaenoic acid, eicosapentaenoic acid, etc.
• 3-methyl-1-butanol e.g., pentadecane, and 1-pentene.
• aldehydes e.g., methanal (formaldehyde), ethanal (acetaldehyde), propanal (propionaldehyde)
• butanal hexanal
• octanal caprylaldehyde
• decanal caprinaldehyde
• 2-propenal acrolein, acrylaldehyde
• 2-butenal crotonaldehyde
• benzaldehyde etc.
• the "visceral odor derived from marine raw materials” refers to the odor peculiar to the internal organs of marine raw materials (fish and shellfish raw materials) and the smell produced by the oxidation or enzymatic reaction of the internal organs of marine raw materials (fish and shellfish raw materials).
• Compounds that cause visceral odors derived from marine raw materials include, for example, trimethylamine, triethylamine, diosmin, and geosmin.
• unpleasant odors caused by plant raw materials include plant odors, grain odors, lipid oxidation/deterioration odors, vegetable protein odors, amino acid odors, grassy odors, and the like.
• the "plant odor derived from plant raw materials" is an odor peculiar to plants contained in the plant raw materials.
• the "plant-derived grain odor" is the odor peculiar to the grains contained in the plant raw material.
• the "lipid oxidation/deterioration odor derived from plant raw materials” is an odor caused by changes in the oil and fat components contained in the plant raw materials due to oxidation or deterioration.
• Compounds that cause plant odors derived from plant materials, grain odors derived from plant materials, and lipid oxidation/deterioration odors derived from plant materials include, for example, hexanol, hexanal, methional, pentanal, 2-heptanal, 2-octenal, and 2-nonenal.
• the "plant protein odor derived from plant raw materials” refers to the odor peculiar to the protein contained in the plant raw material and the odor produced by the oxidation or enzymatic reaction of the protein contained in the plant raw material.
• the "plant raw material-derived amino acid odor" is an odor caused by oxidation of the amino acids contained in the plant raw material.
• Examples of compounds that cause plant protein odors derived from plant raw materials and amino acid odors derived from plant raw materials include methional, 2-methyl-3-furanthiol, o-aminoacetophenone, and hexanal.
• the "grassy odor derived from plant raw materials" is an odor reminiscent of grass or the like.
• Compounds derived from plant materials that cause grassy smell include, for example, sulfur-containing compounds such as hexanal and sulfides.
• unpleasant odors caused by dairy ingredients include lipid oxidation/deterioration odors (heated deterioration odors, etc.).
• the "lipid oxidation/deterioration odor derived from dairy ingredients” is an odor caused by changes due to oxidation or deterioration of fat and oil components contained in dairy ingredients.
• Compounds that cause oxidized odors derived from dairy ingredients and deteriorated odors derived from dairy ingredients include, for example, 2-heptanone, 2-nonanone, 2-decanone, capric acid (decanoic acid), lauric acid (dodecanoic acid), 2,3 -butanedione, 2-methylpropanal, 3-methylbutanal, nonanal, decanal, dimethylsulfide and the like.
• the "unpleasant odor caused by the yeast raw material” is an odor peculiar to the yeast contained in the yeast raw material.
• oils and fats include lipid oxidation and deterioration odors.
• the "lipid oxidation/deterioration odor derived from fats and oils” is an odor that occurs when fat components change due to oxidation or deterioration.
• Compounds that cause oil-derived lipid oxidation odors and oil-derived deterioration odors include, for example, (E,E)-2,4-decadienal, 1-octen-3-one, 4,5-epoxy-trans-2- desenal, hexanal, 2-propenal and the like.
• unpleasant odors derived from egg raw materials include sulfur odor derived from egg raw materials and fishy odor derived from egg raw materials.
• the "sulfur odor derived from the egg raw material" is the smell of sulfur-containing compounds contained in the egg raw material.
• sulfur odor-causing compounds derived from egg raw materials include hydrogen sulfide, methyl mercaptan, methyl sulfide, dimethyl mercaptan, ethyl mercaptan, dimethyl disulfide, sulfur dioxide, and methional.
• the "fishy odor derived from egg raw materials" is the odor peculiar to raw eggs.
• Examples of compounds that cause a fishy odor derived from egg raw materials include hexanal and butyl acetate.
• unpleasant odors caused by edible insects include visceral odors, insect odors, protein odors, and lipid oxidation/deterioration odors.
• the "visceral odor derived from edible insects” refers to the odor peculiar to the raw viscera of edible insects and the odor produced by the oxidation or enzymatic reaction of the viscera of edible insects.
• visceral odor-causing compounds derived from edible insects include sulfur-containing compounds (eg, methional, hydrogen sulfide, methyl mercaptan, methyl sulfide, dimethyl mercaptan, ethyl mercaptan, dimethyl disulfide, sulfur dioxide, etc.).
• sulfur-containing compounds eg, methional, hydrogen sulfide, methyl mercaptan, methyl sulfide, dimethyl mercaptan, ethyl mercaptan, dimethyl disulfide, sulfur dioxide, etc.
• insects Insect odor derived from edible insects
• odor-causing compounds derived from edible insects include 2-hexanal, 2-octanal, 2-hexenyl acetate, and 2-octenyl acetate.
• the "protein odor derived from edible insects” refers to the odor peculiar to proteins contained in edible insects and the odor produced by oxidation or enzymatic reaction of proteins contained in edible insects.
• Examples of compounds that cause protein odors derived from edible insects include methional and 2-methyl-3-furanthiol.
• the "lipid oxidation/deterioration odor derived from edible insects” is an odor caused by oxidation of oils and fats contained in edible insects.
• Compounds that cause lipid oxidation/degradation odors derived from edible insects include, for example, 3-methyl-1-butanol, pentadecane, 1-pentene-3-ol, 1-octen-3-ol, 2,3-pentanedione, and butyric acid.
• butanoic acid isovaleric acid
• volatile aldehydes e.g., methanal (formaldehyde), ethanal (acetaldehyde), propanal (propionaldehyde), butanal, hexanal, octanal (caprylaldehyde), decanal (caprinaldehyde)
• propenal acrolein, acrylaldehyde
• 2-butenal crotonaldehyde
• the masking agent of the present invention can be suitably used to mask the retort odor.
• the retort odor is an unpleasant odor caused by retort processing, and specific examples thereof include sulfur odor (specific odor of sulfur-containing compounds), stuffy odor (stuffy odor when heated in a sealed container), and the like. be done.
• compounds causing sulfur odors include, for example, hydrogen sulfide, methyl mercaptan, methyl sulfide, dimethyl mercaptan, ethyl mercaptan, dimethyl disulfide, sulfur dioxide, and methional.
• compounds that cause stuffiness include, for example, sulfur-containing compounds (eg, methional, hydrogen sulfide, methyl mercaptan, methyl sulfide, dimethyl mercaptan, ethyl mercaptan, dimethyl disulfide, sulfur dioxide, etc.).
• sulfur-containing compounds eg, methional, hydrogen sulfide, methyl mercaptan, methyl sulfide, dimethyl mercaptan, ethyl mercaptan, dimethyl disulfide, sulfur dioxide, etc.
• the concentration (content) of the compound responsible for the unpleasant odor described above in food is not particularly limited, as long as it is an amount that can normally be contained in food. Specifically, it varies depending on the type of the causative compound, the type of food, etc., but it is usually 0.01 weight ppb to 1 weight % of the food.
• unpleasant food odors e.g., fishy odor derived from meat raw materials, metallic odor derived from meat raw materials, animal odors derived from meat raw materials, lipid oxidation/deterioration odors derived from meat raw materials, visceral odors derived from meat raw materials, Grass odor from meat ingredients, fishy odor from marine ingredients, lipid oxidation/deterioration odor from marine ingredients, visceral odor from marine ingredients, lipid oxidation/deterioration odor from dairy ingredients, vegetable odors from plant ingredients, plant ingredients Grain odor derived from plant raw materials, lipid oxidized/degraded odor derived from plant raw materials, vegetable protein odor derived from plant raw materials, amino acid odor derived from plant raw materials, grassy odor derived from plant raw materials, lipid oxidized/degraded odor derived from oils and fats, egg raw materials Sulfur odor, fishy odor derived from egg raw materials, visceral odor derived from meat raw materials
• the masking agent of the present invention when used in contact with a food containing at least one selected from the group consisting of meat raw materials, marine raw materials, plant raw materials, and yeast raw materials as raw materials or raw materials thereof, the present The masking agent of the invention may contain as an active ingredient at least one compound selected from the group consisting of propionic acid, furfural, 2-acetylfuran and ⁇ -caryophyllene oxide.
• the masking agent of the present invention when used in contact with a food containing as a raw material at least one selected from the group consisting of meat raw materials, marine raw materials, plant raw materials and egg raw materials or raw materials thereof, the present The masking agent of the invention may contain as an active ingredient at least one compound selected from the group consisting of cyclotene, propionic acid, 2-acetylfuran and ⁇ -caryophyllene oxide.
• the masking agent of the present invention when used in contact with a food containing at least one selected from the group consisting of vegetable proteins and oils and fats as a raw material or a raw material thereof, the masking agent of the present invention is It may contain as an active ingredient at least one compound selected from the group consisting of cyclotene, propionic acid, furfural and 2-acetylfuran.
• foods containing the masking agent of the present invention can also be provided.
• the present invention provides a food or raw material thereof by adding at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one. Also provided is a method for producing a food (sometimes simply referred to herein as the "production method of the present invention") comprising contacting with.
• An unpleasant odor masking compound that can be used in the production method of the present invention (at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one ) is the same as the unpleasant odor masking compound described in the above “1.
• Masking agent for unpleasant odor of food is the same as the unpleasant odor masking compound described in the above “1.
• an unpleasant odor masking compound at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one
• the method of bringing the food or its raw material into contact is not particularly limited. It can be carried out by immersion or the like.
• an unpleasant odor masking compound at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one
• the amount of the unpleasant odor masking compound added to the food or its raw material is The amount of the unpleasant odor masking compound added to the food or its raw material is the same as that of the unpleasant odor masking compound added to the food or its raw material when it is added to the food, and the preferred range is also the same.
• an unpleasant odor masking compound at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one
• an unpleasant odor masking compound at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one
• Use amount of liquid containing unpleasant odor masking compound (at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one) (food Or the amount of liquid used for immersing the raw material) is not particularly limited, but is the same as the amount of the liquid containing the masking agent of the present invention (masking liquid), and the preferred range is also the same.
• an unpleasant odor masking compound at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one
• the time for immersing is not particularly limited, it is the same as the time for immersing the food or its raw material in the liquid containing the masking agent of the present invention (masking liquid), and the preferred range is also the same.
• the production method of the present invention includes an unpleasant odor masking compound (from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one). At least one selected compound) may be included as appropriate in addition to contacting with the food, depending on the type of food to be produced and the like.
• the food that can be produced by the production method of the present invention is the same as the food that can use the masking agent of the present invention.
• unpleasant food odors e.g., bloody odor derived from meat raw materials, metallic odor derived from meat raw materials, animal odors derived from meat raw materials, lipid oxidation/deterioration odors derived from meat raw materials, visceral odor from meat ingredients, glass odor from meat ingredients, fishy odor from marine ingredients, lipid oxidation/deterioration odor from marine ingredients, visceral odor from marine ingredients, lipid oxidation/deterioration odor from dairy ingredients, plant ingredients Plant odor, plant-derived grain odor, plant-derived lipid oxidation/deterioration odor, plant-derived vegetable protein odor, plant-derived amino acid odor, plant-derived odor, oil-derived lipid oxidation/deterioration odor , sulfur odor derived from egg raw materials, fishy odor derived from egg raw materials, visceral odor derived from edible insects, insect odor derived from edible insects, protein odor derived from edible insects, lipid oxidation/deterioration odor ,
• the food that can be produced by the production method of the present invention is a food containing as a raw material at least one selected from the group consisting of meat raw materials, marine raw materials, plant raw materials and yeast raw materials.
• the production method may comprise contacting at least one compound selected from the group consisting of propionic acid, furfural, 2-acetylfuran and ⁇ -caryophyllene oxide.
• the food that can be produced by the production method of the present invention is a food containing as a raw material at least one selected from the group consisting of meat raw materials, marine raw materials, plant raw materials and egg raw materials.
• the production method may comprise contacting at least one compound selected from the group consisting of cyclotene, propionic acid, 2-acetylfuran and ⁇ -caryophyllene oxide.
• the production method of the present invention when the food that can be produced by the production method of the present invention is a food containing as a raw material at least one selected from the group consisting of vegetable proteins and fats and oils, the production method of the present invention includes cyclotene, It may comprise contacting with at least one compound selected from the group consisting of propionic acid, furfural and 2-acetylfuran.
• the present invention provides a method for adding at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one to food. Also provided is a method for masking an unpleasant odor of food (in this specification, it may be simply referred to as the “masking method of the present invention”), which includes contacting the raw material of the food.
• An unpleasant odor masking compound that can be used in the masking method of the present invention (at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one ) is the same as the unpleasant odor masking compound described in the above “1.
• Masking agent for unpleasant odor of food is the same as the unpleasant odor masking compound described in the above “1.
• an unpleasant odor masking compound at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one
• the method of bringing the food or its raw material into contact is not particularly limited. It can be carried out by immersion or the like.
• an unpleasant odor masking compound at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one
• the amount of the unpleasant odor masking compound added to the food or its raw material is The amount of the unpleasant odor masking compound added to the food or its raw material is the same as that of the unpleasant odor masking compound added to the food or its raw material when it is added to the food, and the preferred range is also the same.
• an unpleasant odor masking compound at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one
• an unpleasant odor masking compound at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one
• Use amount of liquid containing unpleasant odor masking compound (at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one) (food Or the amount of liquid used for immersing the raw material) is not particularly limited, but is the same as the amount of the liquid containing the masking agent of the present invention (masking liquid), and the preferred range is also the same.
• an unpleasant odor masking compound at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one
• the time for immersing is not particularly limited, it is the same as the time for immersing the food or its raw material in the liquid containing the masking agent of the present invention (masking liquid), and the preferred range is also the same.
• an unpleasant odor masking compound at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one
• the timing of immersion is not particularly limited, but includes, for example, during food production, after food production, and the like.
• an unpleasant odor masking compound at least one compound selected from the group consisting of cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide and 2-methyltetrahydrofuran-3-one
• the time (timing) is not particularly limited, but includes, for example, during food production, after food production, and the like.
• the foods for which the masking method of the present invention can be used are the same as the foods for which the masking agent of the present invention can be used.
• unpleasant food odors e.g., bloody odor derived from meat raw materials, metallic odor derived from meat raw materials, animal odors derived from meat raw materials, lipid oxidation/deterioration odors derived from meat raw materials, visceral odor from meat ingredients, glass odor from meat ingredients, fishy odor from marine ingredients, lipid oxidation/deterioration odor from marine ingredients, visceral odor from marine ingredients, lipid oxidation/deterioration odor from dairy ingredients, plant ingredients Plant odor, plant-derived grain odor, plant-derived lipid oxidation/deterioration odor, plant-derived vegetable protein odor, plant-derived amino acid odor, plant-derived odor, oil-derived lipid oxidation/deterioration odor , sulfur odor derived from egg raw materials, fishy odor derived from egg raw materials, visceral odor derived from edible insects, insect odor derived from edible insects, protein odor derived from edible insects, lipid odor derived from edible insects, lipid
• the food that can be used with the masking method of the present invention is a food containing as a raw material at least one selected from the group consisting of meat raw materials, marine raw materials, plant raw materials, and yeast raw materials.
• Masking methods may include contacting with at least one compound selected from the group consisting of propionic acid, furfural, 2-acetylfuran and ⁇ -caryophyllene oxide.
• One aspect of the food that can be used with the masking method of the present invention is a food containing as a raw material at least one selected from the group consisting of meat raw materials, marine raw materials, plant raw materials and egg raw materials.
• Masking methods may include contacting with at least one compound selected from the group consisting of cyclotene, propionic acid, 2-acetylfuran and ⁇ -caryophyllene oxide.
• the masking method of the present invention when the food to which the masking method of the present invention can be applied is a food containing as a raw material at least one selected from the group consisting of vegetable proteins and fats and oils, the masking method of the present invention includes cyclotene, It may comprise contacting with at least one compound selected from the group consisting of propionic acid, furfural and 2-acetylfuran.
• Raw materials, reagents, compounds, and the like used in the present examples are readily available or can be prepared according to methods commonly practiced in the technical field, or are commercially available, unless otherwise specified. is.
• a control beef hamburger was prepared in the same manner as the evaluation samples, except that no unpleasant odor masking compounds (cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide) were used.
• the beef hamburgers to which cyclotene, propionic acid, furfural, 2-acetylfuran or ⁇ -caryophyllene oxide were added all had unpleasant odors (bloody odor derived from meat raw materials, iron odor, animal odor derived from meat raw materials, lipid oxidation/deterioration odor derived from meat raw materials, and glass odor derived from meat raw materials) were masked. confirmed.
• Example 2 Preparation of evaluation sample
• the compounds shown in Table 2 below cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide, 2-methyltetrahydrofuran-3-one
• concentrations shown in Table 2 below concentrations shown in Table 2 below. (percentage to the total weight of the evaluation sample), and then mixed for about 1 minute using a spatula to prepare each evaluation sample.
• liver pastes to which cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide or 2-methyltetrahydrofuran-3-one were added all had an unpleasant odor ( visceral odor) was masked, it was confirmed that each of these compounds has an effect of masking an unpleasant odor.
• Example 3 Preparation of evaluation sample 1-octen-3-ol was dissolved in water to a concentration of 50 weight ppb, and the resulting aqueous solution was added with the compounds shown in Table 3 below (cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide, 2-methyltetrahydrofuran-3-one) were added at concentrations shown in Table 3 below (proportion to the total weight of the evaluation sample) to prepare each evaluation sample.
• Table 3 cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide, 2-methyltetrahydrofuran-3-one
• Example 4 (Preparation of evaluation sample) To 40 parts by weight of water (masking liquid) to which the compounds (cyclotene, propionic acid, furfural, 2-acetylfuran) shown in Table 4 below are added at the concentrations shown in Table 4 below, 100 parts by weight of mackerel fillet, After being immersed overnight in a refrigerator (about 5°C), the liquid was drained and both sides were baked for 3 minutes each at medium heat using a frying pan to prepare each evaluation sample (grilled mackerel).
• water mass liquid
• mackerel fillet 100 parts by weight of mackerel fillet
• Control grilled mackerel was prepared in the same manner as for the evaluation samples, except that the mackerel fillet was immersed in water to which the compound shown in Table 4 below was not added, instead of the masking solution.
• the grilled mackerel obtained by immersing the raw material (mackerel fillet) in a liquid containing cyclotene, propionic acid, furfural or 2-acetylfuran has an unpleasant odor (fishy odor derived from marine raw materials, fishery Since the lipid oxidation/deterioration odor derived from the raw materials was masked, it was confirmed that each of these compounds has the effect of masking the unpleasant odor.
• Example 5 (Preparation of evaluation sample) Water (masking liquid ), 100 parts by weight of boiled clams were immersed overnight in a refrigerator (about 5°C) and then immersed in hot water at 85°C for 20 minutes to prepare an evaluation sample (boiled clams).
• Control boiled clams were prepared in the same manner as the evaluation samples, except that the boiled clams were not immersed in the masking solution.
• Example 6 (Preparation of evaluation sample) Trimethylamine was dissolved in water to a concentration of 50 ppb by weight, and the resulting aqueous solution was added with the compounds shown in Table 6 below (cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide, 2- methyltetrahydrofuran-3-one) was added at the concentration shown in Table 6 below (percentage relative to the total weight of the evaluation sample) to prepare each evaluation sample.
• Table 6 cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide, 2- methyltetrahydrofuran-3-one
• Example 7 (Preparation of evaluation sample) 2 g of instant coffee powder (Nescafe Gold Blend (Nestlé Japan Co., Ltd.)) was dissolved in 140 mL of hot water, and 10 parts by weight of granulated sugar and 5 parts by weight of milk were added to 85 parts by weight of the resulting coffee liquid and stirred well. 180 mL of the resulting milk drink was placed in a can, sealed by a can making machine, and then subjected to retort treatment (120° C., 20 minutes).
• control Except that no unpleasant odor masking compounds (cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide, 2-methyltetrahydrofuran-3-one) were added, the control was prepared in the same manner as the evaluation sample. A retort milk drink was prepared.
• Example 8> Preparation of evaluation sample 2-nonanone was dissolved in water so that the concentration was 2 ppm by weight, and the resulting aqueous solution was added with the compounds shown in Table 8 below (cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide, 2-Methyltetrahydrofuran-3-one) was added at the concentration shown in Table 8 below (percentage to the total weight of the evaluation sample) to prepare each evaluation sample.
• Table 8 below cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide, 2-Methyltetrahydrofuran-3-one
• Example 9 Preparation of evaluation sample 4 g of soy protein powder (SUPURO 661 (DDP Specialty Products Japan K.K.)) was added to 96 g of water, stirred, left overnight in a refrigerator (about 5°C), and then the supernatant was collected. The collected supernatant was added with the compounds (cyclotene, propionic acid, furfural, 2-acetylfuran, 2-methyltetrahydrofuran-3-one) shown in Table 9 below at concentrations shown in Table 9 below (total of evaluation samples weight ratio) to prepare each evaluation sample (soybean powder aqueous solution).
• soy protein powder SUPURO 661 (DDP Specialty Products Japan K.K.)
• control soybean powder aqueous solution was prepared in the same procedure as for the evaluation samples, except that no unpleasant odor masking compounds (cyclotene, propionic acid, furfural, 2-acetylfuran, 2-methyltetrahydrofuran-3-one) were added. did.
• Example 11 (Preparation of evaluation sample) Methional was dissolved in water to a concentration of 300 ppb by weight, and the resulting aqueous solution was added with the compounds shown in Table 11 below (cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide, 2- methyltetrahydrofuran-3-one) was added at the concentration shown in Table 11 below (percentage to the total weight of the evaluation sample) to prepare evaluation samples.
• Table 11 cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide, 2- methyltetrahydrofuran-3-one
• Example 12 (Preparation of evaluation sample) Isovaleric acid was dissolved in water to a concentration of 3 ppb by weight, and the resulting aqueous solution was added with the compounds shown in Table 12 below (cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide, 2-Methyltetrahydrofuran-3-one) was added at concentrations shown in Table 12 below (percentage of total weight of evaluation sample) to prepare evaluation samples.
• Table 12 cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide, 2-Methyltetrahydrofuran-3-one
• Example 13 (Preparation of evaluation sample) Hexanal was dissolved in water to a concentration of 0.5 ppb by weight, and the resulting aqueous solution was added with the compounds shown in Table 13 below (cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide, 2-Methyltetrahydrofuran-3-one) was added at concentrations shown in Table 13 below (percentage of total weight of evaluation sample) to prepare evaluation samples.
• Table 13 cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide, 2-Methyltetrahydrofuran-3-one
• Example 14 (Preparation of evaluation sample) Dimethyl disulfide was dissolved in water to a concentration of 3 ppb by weight, and the resulting aqueous solution was added with the compounds shown in Table 14 below (cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide, 2 -methyltetrahydrofuran-3-one) was added at the concentration shown in Table 14 below (as a percentage of the total weight of the evaluation sample) to prepare evaluation samples.
• Table 14 cyclotene, propionic acid, furfural, 2-acetylfuran, ⁇ -caryophyllene oxide, 2 -methyltetrahydrofuran-3-one
• the masking agent which can mask the unpleasant smell of food can be provided.
• the masking agent of the present invention can mask unpleasant odors without imparting flavor derived from its active ingredients to foods. Further, according to the present invention, it is possible to provide a method for masking an unpleasant odor of food and a method for producing food in which the unpleasant odor is masked.

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• 2022
  • 2022-03-15 JP JP2023510889A patent/JPWO2022209861A1/ja active Pending
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