Oil / fat deterioration smell-masking agent

Abstract

To provide a novel masking agent for oil / fat deterioration smell.SOLUTION: An oil / fat deterioration masking agent, containing at least one compound selected from the following group: styralyl alcohol, benzyl alcohol, ethyl pyruvate, γ-butyrolactone, methyl jasmonate, methyl dihydrojasmonate, 1,8-cineole, dihydroactinidiolide, rose oxide, β-damascenone, anethole, sclareolide, menthone, 1,4-cineole, and 6-methyl-5-heptene-2-one.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a masking agent for the deterioration odor of fats and oils and a method for using the same. More specifically, the present invention relates to a masking agent for suppressing deterioration (oxidation) odor caused by heating, storage, etc. of fats and oils, a method for masking the deterioration odor of fats and oils using the masking agent, a fat-containing product containing the masking agent, and a method for producing the fat-containing product. [Background technology]

[0002] Fats and oils, or products containing fats and oils, often undergo a heating process during their manufacturing process. It is known that during this heating process and during the subsequent storage period, fats and oils deteriorate due to oxidation, resulting in a deterioration odor (off-flavor) (Patent Document 1). The odor of deteriorated fats and oils does not only occur when the product itself contains fats and oils, but also when the odor of deteriorated fats and oils in the environment transfers to the product, such as when the odor of fried food floating in the store transfers to a product displayed in a convenience store.

[0003] Because such deterioration odors have a significant impact on product quality, attempts have been made to suppress the generation of deterioration odor components or to suppress the deterioration odors by using masking agents. For example, attempts have been made to add ethyl decanoate to foods and beverages that have an oily deterioration odor (Patent Document 1).

[0004] However, as the issues surrounding the odor of deteriorated oils and fats are diversifying, such as the transfer of the smell of fried food to products displayed in convenience stores, there is a demand for technology that can more versatilely and effectively mask the odor of deteriorated oils and fats. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Patent Publication No. 2006-197857 Summary of the Invention [Problem to be solved by the invention]

[0006] In view of the problems in the conventional technology, the present invention aims to provide a novel masking agent for the odor of deteriorated oils and fats. Another object of the present invention is to provide a novel masking method using the novel masking agent, a method for producing an oil-containing product, and an oil-containing product obtained by the method. [Means for solving the problem]

[0007] Under such circumstances, the present inventors, through extensive trial and error, identified the main odorous substances that constitute the deterioration odor derived from oils and fats in oil-containing products. Based on the above findings, the present inventors conducted extensive research into the masking effect of a wide variety of components and their combinations on the deterioration odor of oils and fats, and found that the components or combinations thereof described below have a masking effect on the deterioration odor of oils and fats, thereby completing the present invention.

[0008] Thus, the present invention provides the following: Item 1. An oil and fat deterioration odor masking agent comprising at least one compound selected from the group consisting of the following groups A to C: (Group A) styraryl alcohol, benzyl alcohol, ethyl pyruvate, γ-butyrolactone, methyl jasmonate, and methyl dihydrojasmonate (Group B) 1,8-cineole, dihydroactinidiolide, rose oxide, and β-da Massenon (Group C) anethole, sclareolide, menthone, 1,4-cineole, and 6-methyl-5-hepten-2-one.

[0009] Item 2. The masking agent according to item 1, wherein at least two of the compounds contained in the masking agent are compounds belonging to different groups among Groups A to C.

[0010] Item 3. A method for masking an odor of oil and fat deterioration, comprising adding the masking agent according to item 1 or 2 to a product that may emit an odor of oil and fat deterioration.

[0011] Item 4. A method for producing an oil-containing product, comprising adding the masking agent according to item 1 or 2 to an oil-containing product.

[0012] Item 5. An oil-containing product containing the masking agent according to item 1 or 2. Effect of the Invention

[0013] According to the present invention, a novel masking agent for the deterioration odor of oils and fats can be provided. Since the present invention can mask the deterioration odor of oils and fats, it is possible to suppress the deterioration of the flavor of oil-containing products and easily and effectively maintain the quality of the oil-containing products. In addition, even if the odor of fried food is transferred to products displayed in a convenience store, supermarket, etc. (for example, the odor is transferred to paper-packaged beverages, etc.), the deterioration odor can be made less noticeable. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0014] As used herein, the phrase "comprise" or "containing" is intended to encompass the phrase "consisting of" and the phrase "consisting only of".

[0015] The operations and steps described herein may be carried out at room temperature unless otherwise specified.

[0016] In this specification, the term "room temperature" is understood in accordance with common technical knowledge, and can mean, for example, a temperature within the range of 10°C to 35°C.

[0017] The present invention will be described in detail below. The products to which the present invention is directed broadly include general products that may produce the odor of deteriorated oils and fats, such as products containing oils and fats. The oils and fats are not particularly limited, but examples thereof include vegetable oils and fats (e.g., tallow seed oil, linseed oil, almond nut oil, perilla oil, olive oil, orange seed oil, pumpkin seed oil, kapok oil, mustard oil, bitter melon seed oil, catalpa seed oil, conjugated linoleic acid-containing oils and fats, calendula seed oil, wheat germ oil, rice bran oil, corn oil, sesame oil, cherry seed oil, safflower oil, pomegranate seed oil, perilla oil, snake guard seed oil, soybean oil, tea oil, and moon-viewing oil). grass seed oil, camellia oil, rapeseed oil, bitter melon seed oil, trumpet vine seed oil, balsam apple seed oil, palm oil, sunflower oil, peanut oil, grape seed oil, impatiens seed oil, macadamia nut oil, cottonseed oil, peanut oil), animal fats and oils (e.g., beef tallow, horse oil, lard, egg yolk oil, fish oil, liver oil, orbital oil, seal oil, krill oil), other fats and oils (e.g., fats and oils derived from the genus Schizochytrium, fats and oils derived from the genus Nitzschia, fats and oils derived from the genus Nannochloris, and fats and oils derived from the genus Mortierella). Typical examples of fat-and-oil-containing products include foods containing fat-and-oil. Examples of foods include foods made of one or more foods selected from all of the foods listed below, foods made from one or more foods selected from all of the foods listed below as raw materials, and foods made from one or more foods selected from all of the foods listed below as raw materials. Examples of foods include foods containing one or more of the foods listed below.

[0018] (1) Agricultural products and processed agricultural foods: Brown rice, semi-polished rice, 70% polished rice, polished rice, germ polished rice, indica rice, fortified rice, porridge, alpha rice, mochi, red rice, rice vermicelli, rice malt, buckwheat, corn, popcorn, corn flakes, cornmeal, oats, millet, pearl barley, barnyard millet, sorghum, rye, Jerusalem artichoke, potato, sweet potato, yam, taro, konjac, millet, oatmeal, quaker oatmeal, barley, millet, wheat, starch (potato starch, arrowroot, cornstarch, tapioca , rice flour, shiratama flour), starch noodles (harusame, kuzukiri), white bread, dry bread, French bread, rye bread, grape bread, roll bread, croissant, bread crumbs, sweet bread, bean paste bread, cream bread, jam bread, chocolate cornet, Danish pastry, pancake, udon, dried udon, somen, hiyamugi, Chinese noodles, instant ramen, non-fried noodles, cup noodles, pasta, macaroni, spaghetti, wheat gluten, raw wheat gluten, baked wheat gluten, chikuwa wheat gluten, wheat germ, pickles, boiled beans, natto, frozen tofu, tofu, nametake tea pickles, processed wild vegetables, seasoned Menma (bamboo shoots), jams and marmalades, peanut butter and peanut cream, canned tomatoes, salads, canned ingredients, frozen vegetables, processed potatoes, fruits such as akebia japonica and acerola , avocado, apricot, strawberry, fig, iyokan, plum, olive, orange, persimmon, kabosu, quince, kiwi fruit, kumquat, guava, gumi, grapefruit, cherry, pomegranate, sanbokan, shiikuwasha, watermelon, sudachi, plum, daidai, cherimoya, durian, pear, summer mandarin, hyuganatsu, loquat, feijoa, nectarine, pineapple, hassaku, passion fruit, banana, papaya, loquat, grape, blueberry, pomegranate, ponkan, makuwauri, mango, mangosteen, unshu mikan, kiyomi mikan, seminole, melon, peach, bayberry, yuzu, pear, lychee, lime, raspberry, longan, apple, lemon, and beans, adzuki beans, kidney beans. , peas, cowpeas, broad beans, soybeans, grape peas, chickpeas, lima beans, lentils, mung beans, tofu (silk, cotton, soft, filled), grilled tofu, fresh tofu, fried tofu, tofu dumplings, frozen tofu, natto, tempeh, kinako, miso (rice miso, barley miso, soybean miso, kinzanji miso), okara, soy milk, adjusted soy milk, yuba (fresh, dried), chickpeas, almonds, hemp seeds, cashew nuts, pumpkin seeds, ginkgo nuts, chestnuts, walnuts, poppy seeds, coconut, sesame seeds, sesame paste, lotus nuts, pistachios, sunflower seeds, hazelnuts, pecans, macadamia nuts, pine nuts, peanuts, mushrooms such as enoki mushrooms, kikurage mushrooms, shiitake mushrooms , Buna-shimeji, Hon-shimeji, Hatake-shimeji, Nameko, Hatsutake, Oyster, Fukuro-dake, Maitake, Mushrooms, Matsutake, Vegetables include artichokes, Asatsuki, Ashitaba, asparagus, burdock, edamame, Osaka Shirona, hijiki, okra, radish sprouts, turnip, pumpkin, mustard, cauliflower, kanpyo, chrysanthemum, cabbage, cucumber, kyona, kintzai, green peas, watercress, arrowhead, kohlrabi, burdock, komatsuna, konjac, zha cai, sweet potato, taro, green beans, snow peas Duck, lettuce, Chinese cabbage, shishito pepper, perilla, potato, chrysanthemum, watercress, ginger, Japanese radish, Chinese taro, zucchini, zucchini, parsley, celeriac, celery, fern, broad beans, tatsoi, daikon, Chinese cabbage, bamboo shoots, onion, taro buds, chicory, bok choy, horsetail, mustard greens, vine mustard, purple morning glory, Japanese butterbur , chili pepper, gourd, corn, tomato, donburi, eggplant, rape blossoms, rapeseed, bitter melon, chives, carrots, garlic, garlic sprouts, green onions, nozawana, nobiru, Chinese cabbage, lotus root, parsley, chives flowers, chayote, beets, bell peppers, hinona, Hiroshimana, butterbur, butterbur sprouts, Japanese cucumber, broccoli, loofah, spinach, horseradish , mitsuba, myoga, Brussels sprouts, bean sprouts, molokheiya, mountain burdock, mountain yam (icchoimo, jinenjo, naigam), yugao, lily root, yomena, mugwort, shallot, radish, leek, rhubarb, lettuce, scallions, wasabi, bracken, etc., can be prepared raw, salted, pickled, pickled in rice bran, mustard-pickled, eggplant-pickled, in vinegared dishes, simmered, grilled, steamed, dried, in powder, or as kimchi. Seaweeds include green laver, akameku, arame, iwanori, egonori, ogonori, and ko Nbu, suizenji nori, tengusa, tosaka nori, amanore, hijiki, hitoegusa, funori, hondawara, makusa, mozuku, wakame, white seaweed, blue seaweed.

[0019] (2) Milk oil products: Milk, raw milk, processed milk, low-fat milk, dairy drinks (coffee, fruit), cream, fat-replacement cream, coffee whitener, fermented milk, lactic acid bacteria drinks, yogurt, skim milk powder, modified milk powder, unsweetened condensed milk, sweetened condensed milk, cheese (Edam, Emmental, cottage, Camembert) , cream, gouda, cheddar, parmesan, blue, gruyere, mascarpone, mozzarella, roquefort, pizza cheese, processed cheese, cheese spread, cheese food, processed cheese, natural cheese, cheese spread, cheese fondue, ice cream, ice milk, lacto ice cream, soft serve ice cream, sorbet, butter, margarine, fat spread, fresh cream, coffee cream, bottle cream, portioned cream, instant creamy powder, infant formula, As for food oils, soybean, rapeseed, cottonseed, sesame, safflower, corn, sunflower, palm, olive, rice bran, and blended oils are used. As for animal oils, beef tallow, lard, shortening, margarine, and fats are used. spreads, butter, fish oil, whale oil.

[0020] (3) Meat and processed livestock products, etc.: Duck, wild boar, rabbit, beef (shoulder, shoulder roast, rib roast, sirloin, rump, fillet, belly, shank, round, rump, tail) (with or without fat), pork, trotters, quail, horse, frog, wild duck, pheasant, deer, whale, turkey, sparrow, soft-shelled turtle, chicken (wing, breast, thigh, fillet) (with or without skin), skin, pigeon, guinea finch, mountain geese, insects, roast pork, beet Con, shoulder bacon, ham, sausage (dry, semi-dry, bologna, frankfurter, wiener), liver paste, gelatine, mutton, lamb, goat, eggs (duck, century egg, quail, chicken), egg tofu, rolled omelet, organ meats such as tongue, heart Liver, kidneys, stomach, tail, gizzard, corned beef, Canned processed meat products, grilled meat, roast beef, etc.

[0021] (4) Fish, fishery products, etc.: Bluefin tuna, red fish, red sea bream, conger eel, cherry sea bream, horse mackerel, tilefish, net, sweetfish, monkfish, squid, sand lance, grunt, threadfin tuna, stonefish, warty sea bream, sardine, rock char, ugui, eel, sea urchin, filefish, ray, shrimp, oyster, large net, scorpionfish, scorpionfish, halibut, scorpionfish, sculpin, swordfish, bonito, Japanese amberjack, crab (hairy crab, snow crab, king crab, blue crab), barracuda, flounder, amberjack, yellow croaker, Japanese smelt, Japanese smelt, silver herring, cucumberfish, caviar, silver cod, golden tuna, black croaker, jellyfish, carp, flathead, salmon (sujiko, salmon roe, mefun) Fish meat and / or innards such as: saba, mackerel, shark, halfbeak, crayfish, Japanese Spanish mackerel, saury, whitebait, capelin, solefish, mantis shrimp, striped jack, whitebait, Japanese sea bass, sardine, sea bream, sea bream, octopus, Japanese batfish, cod (cod roe, milt, roe), loach, flying fish, sea cucumber, catfish, bitterling, herring (herring roe), goby, sandfish, conger eel, flatfish, pufferfish, crucian carp, flounder, black bass, gurnard, firefly squid, atka mackerel, ascidian, mullet, tuna, trout, mandarin tuna, mutsu, mejina, rockfish, hake, sardine, yagara, lamprey eel, mountain trout, smelt, smelt, smelt, sashimi, surimi, simmered , grilled, tsukudani, candied, pickled in sweet vinegar, salted, smoked, raw dried, whole dried, mezashi, canned in water, canned in seasoning, canned in oil, flakes, unglazed grilled, kabayaki, shiokara, dried squid, sakiika, smoked, niboshi, shirasu-boshi, tazukuri, tatami-iwashi, mirin-boshi, anchovies (in the case of sardines), namari, bonito flakes, kakuni (in the case of bonito), shellfish such as green goats, akagai, a Raw and preserved seafood such as clams, clams, abalone, cockles, escargots, oysters, turban shells, corbicula, flathead clams, snails, whelks, cockles, chicken clams, turban shells, sea cucumbers, fin clams, scallops, surf clams, fin clams, mussels, mussels, and cockles. Boiled, boiled, scallops, dried sardines.

[0022] (5) Confectionery: Amanatto, fresh yatsuhashi with bean paste filling, imagawayaki, uiro, uguisu mochi, kashiwa mochi, castella cake, kanoko, karukan, millet dango, gyuhi, kirizansho, gold sugar, kintsuba, kusamochi, skewered dango, sakura mochi, daifuku mochi, chimaki, chatu, dorayaki, nerikiri, manju, monaka, yubeshi, yokan (kneaded, water, steamed), candy, potato karinto, okoshi, karinto, gokabo, shio gama, hina arare, boro, matsukaze, bean sweets, yatsuhashi, rakugan, senbei, rice crackers (arare, fried senbei, sweet and spicy senbei, salted senbei), apple pie, custard pudding Rins, cupcakes, cream puffs, shortcakes, jellies, doughnuts, bavarois, marron glacés, meat pies, milk puddings, waffles, wafers, crackers, sables, snacks (potato chips, fabricated potatoes, potato juice rings, etc., potato-based, corn-based, flour-based, rice-based, others), puff pies, biscuits, cookies, Russian cakes, caramel, tablets, jelly candy, jelly beans, China marble, drops, nougat, butterscotch, brittle, marshmallows, chocolate, chocolate candy, chewing gum, Chinese sweets (geppei, Chinese cookies, Chinese buns), confectionery B, pretzels, semi-dried cakes, chocolate cakes, candy, menthol candy, throat lozenges, herb candy, mouth refreshing sweets, caramel, gummy candy, nuts, bean sweets, toy sweets, jelly sweets, karinto, amanatto, mixed sweets, wafer sweets, marshmallows, mint tablet sweets.

[0023] (6) Seasonings: Sugar (white sugar, brown sugar, brown sugar, wasanbon sugar, granulated sugar, sugar cubes, rock sugar, coffee sugar, powdered sugar), starch syrup, honey, maple syrup, soy sauce (dark, light, tamari, lightly salted, reduced salt), dashi soy sauce, vinegar (grain vinegar, rice vinegar, fruit vinegar, ponzu, wine vinegar, processed vinegar), sauces (Worcestershire, medium-thick, rich, okonomiyaki sauce, yakisoba sauce, oyster sauce, steak sauce, pepper sauce), dashi stock (powder, liquid, solid), Chinese style Seasonings, tomato ketchup, chili sauce, hayashi roux, pizza sauce, stew roux, curry roux, dressing, dressing-type seasonings, mayonnaise, noodle soup base, mirin, mirin-style seasoning, fermented seasonings, flavor seasonings, edible oil, olive oil, sesame oil, miso, soup base, tomato processed products, yakiniku sauce, shabu-shabu sauce, sukiyaki sauce, pure curry, consomme bouillon, nucleic acid complex seasoning, pickled vegetables base, ramen soup, udon soup, clear soup.

[0024] (7)Spices: Allspice, onion powder, mustard, garlic, curry, cloves, pepper, sansho pepper, cinnamon, ginger, sage, thyme, chili powder, chili pepper, nutmeg, paprika, pepper sauce, mustard, chili oil, wasabi, yeast, sake lees.

[0025] (8) Cooked processed foods: Curry (canned / retort), corn cream soup, corn potage soup, stew, mapo tofu base, meat sauce, spring rolls, dogs, egg tofu, toaster oven food, microwave food, baby food, tamagoyaki (Japanese rolled omelette), hamburger, chicken nuggets, french fries, shakes, fried chicken, bento, prepared foods, snack noodles, fresh snack noodles, instant noodles, fresh noodles, dried noodles, pasta, retort rice, aseptically packaged cooked rice, porridge, porridge, packaged mochi, Chinese steamed buns, Real foods, premix powder (unsweetened), okonomiyaki mix, premix powder (sweetened), rice vermicelli, nutritionally balanced meals (solid type), instant curry, canned curry, retort curry, pasta sauce, menu-specific combined seasonings, sushi mix, kamameshi mix, donburi mix, oden mix, ochazuke, furikake, rice ball mix, zosui mix, pizza sauce, western-style sauce, instant stew, retort stew, instant hayashi, retort hayashi, fried rice mix, frozen and chilled foods (Udon, shrimp gratin, shrimp doria, shrimp pilaf, fried shrimp, gyoza, fried rice, croquettes, shumai, fried chicken, pie crust, hamburger, french fries, mixed pizza, mixed vegetables, meatballs, minced meat cutlet, grilled rice balls, cutlets, gratin, tempura, okonomiyaki, takoyaki, fried seafood, chawanmushi, noodles, rice dishes, pilaf dishes, pizza pie), soups (cooking soup, instant soup, cup soup (Soups, retort soups, canned soups, frozen soups, chilled soups, seaweed soups, Chinese soups, vendor canned soups, egg soups, instant miso soups).

[0026] (9) Beverage: Fruit drinks: natural fruit juice, fruit juice drinks, soft drinks with fruit juice, honey drinks, diluted drinks, fruit drinks with fruit pellets, fruit pulp drinks, tomato drinks, vegetable drinks, mixed fruit juice drinks with vegetables, fruit water, soft drinks with fruit pellets; carbonated drinks: cola-flavored drinks, clear carbonated drinks, rum Ne-flavored drinks, low-alcohol fruit juice carbonated drinks, fruit colored carbonated drinks, low-alcohol fruit juice carbonated drinks, ginger ale, dairy carbonated drinks, wine-like fruit juice carbonated drinks, high-alcohol fruit juice carbonated drinks, fruit juice carbonated drinks, dairy drinks such as drinking milk, pasteurized milk, dairy drinks, high-fat drinks, Low-fat beverages, dairy lactic acid bacteria beverages, lactic acid bacteria beverages, pasteurized dairy lactic acid bacteria beverages (concentrated), pasteurized dairy lactic acid bacteria beverages (straight), LL drinking milk, soft drinks containing dairy, and beverages of your choice Green tea (gyokuro, matcha, sencha, bancha, roasted green tea, genmaicha), oolong tea, black tea, mate tea, kombucha, barley tea, tochu tea, herbal tea, medicinal herb tea, tea containing herbal ingredients, amazake, cocoa, coffee, coffee drinks, shiruko, non-alcoholic beer, jelly drinks, Vermont drinks, health drinks, food drinks, sports drinks, soy milk, vinegar drinks, malt Drinks, functional drinks, vitamin supplement drinks, mineral supplement drinks, alcoholic drinks and We have sake, unpasteurized sake, shochu type A, shochu type B, chuhai, whiskey, brandy, beer, 100% malt beer, dry beer, imported beer, light beer, new spirits, spirits, wine, cocktail drinks, water-diluted liquor, sparkling wine, plum wine, white sake, medicated sake, Other beverages include mineral water, sour drinks, meal-type beverages, and tonic water. Eater, carbonated water, near water.

[0027] (10) Desserts: Chilled pudding, chilled jelly, daily desserts, plain yogurt, hard yogurt, soft yogurt, drinking yogurt, frozen yogurt, ice cream, high-quality ice cream, multi-pack ice cream, bite-sized jellies, Western-style packed desserts, dessert bases (retort), dessert bases (powder), Japanese-style desserts, frozen cakes, homemade-style desserts, fruit sorbets, desserts with nata de coco, retort shiruko and zenzai, dried jelly.

[0028] The proportion of fats and oils contained in the fat-and-oil-containing product is not particularly limited, but for example, fats and oils in the range of 0.0001 to 100 mass%, 0.001 to 95 mass%, 0.01 to 90 mass%, etc. based on the mass of the fat-and-oil-containing product can be used.

[0029] In addition, the oil-deterioration odor masking agent of the present invention can mask not only oil-containing products, but also oil-deterioration odors transferred from objects other than the target product (oil-containing products other than the target product, heated oil for food processing, etc.) as described above. Therefore, the oil-deterioration odor masking agent of the present invention is applicable to oil-containing products in which an oil-deterioration odor has occurred or may occur, and products to which an oil-deterioration odor derived from objects other than the target product has adhered or may adhere. In the present invention, "oil-containing products in which an oil-deterioration odor has occurred or may occur, and products to which an oil-deterioration odor derived from objects other than the target product has adhered or may adhere" is sometimes referred to as "products that can emit an oil-deterioration odor."

[0030] As described in the Examples below, the present inventors have investigated the effect of the present invention on the oil content of oil-containing products. The main odorous substances that make up the deterioration odor derived from fat were identified. In brief, the inventors identified the main odorous substances that constitute the odor of deteriorated oils and fats by analyzing corn oil that had been heat-treated to produce a deteriorated odor using a gas chromatography olfactometer (hereinafter abbreviated as GC / O).

[0031] Suitable specific examples of such major odor substances include trans-4,5-epoxy-(E)-2-decenal, 1-octen-3-one, and (E,E)-2,4-decadienal. Thus, in a typical embodiment, the odor of oil deterioration is produced by a combination of odor substances containing the above three components. As described below, according to the present invention, such an odor of oil deterioration can be masked by adding at least one compound selected from the group consisting of the above-mentioned groups A, B, and C.

[0032] The oil and fat deterioration odor masking agent of the present invention (hereinafter, this may be referred to as a "deterioration odor masking agent" or a "masking agent") contains, as an active ingredient, one or more compounds selected from the group consisting of the following Group A, Group B, and Group C (hereinafter, this may be referred to as a masking agent compound); (Group A) styraryl alcohol, benzyl alcohol, ethyl pyruvate, γ-butyrolactone, methyl jasmonate, and methyl dihydrojasmonate (Group B) 1,8-cineole, dihydroactinidiolide, rose oxide, and β-damascenone (Group C) anethole, sclareolide, menthone, 1,4-cineole, and 6-methyl-5-hepten-2-one.

[0033] The compounds in groups A, B, and C are all known aroma components. In the present invention, the compound may be a product purified from a natural flavoring or a product synthesized by a chemical reaction, without any restrictions. For convenience, these commercially available products may be preferably used in the present invention.

[0034] In addition, natural flavors containing the compound can be used as the masking agent of the present invention, provided that the effect of the present invention is not impaired. Examples of such natural flavors include, but are not limited to, natural flavors containing styralyl alcohol, such as cocoa flavor, plum flavor, and honey flavor; natural flavors containing benzyl alcohol, such as grape flavor, hop flavor, and black tea flavor; natural flavors containing ethyl pyruvate, such as cheese flavor, wine lees flavor, and honey flavor; natural flavors containing γ-butyrolactone, such as coffee flavor and milk flavor; natural flavors containing methyl jasmonate, such as jasmine flavor, black tea flavor, and lemon flavor; natural flavors containing methyl dihydrojasmonate, such as jasmine flavor and black tea flavor; natural flavors containing 1,8-cineole, such as eucalyptus flavor. natural flavors containing dihydroactinidiolide include black tea flavor and melissa flavor; natural flavors containing rose oxide include rose flavor, geranium flavor, tomato flavor, etc.; natural flavors containing β-damascenone include rose flavor, geranium flavor, coffee flavor, etc.; natural flavors containing anethole include star anise flavor and fennel flavor; natural flavors containing menthone include peppermint flavor and peppermint flavor; natural flavors containing 1,4-cineole include rosemary flavor and laurel flavor; and natural flavors containing 6-methyl-5-hepten-2-one include lemongrass flavor and ginger flavor.

[0035] The deterioration odor masking agent of the present invention is characterized in that it contains one or more compounds selected from the group consisting of Group A, Group B, and Group C (i.e., a compound group including all of the compounds belonging to Group A, Group B, and Group C). Unless otherwise specified, the compound "two or more compounds selected from the group consisting of Group A, Group B, and Group C" includes not only two or more compounds containing compounds belonging to different groups, but also two or more compounds containing only compounds belonging to the same group.

[0036] The masking effect can be obtained by using only one of the compounds, a better effect can be obtained by using two or more of the compounds, and an even better effect can be obtained by using three or more of the compounds.

[0037] In the present invention, from the viewpoint of the good masking effect, It is preferable to use a combination of one or more compounds selected from two of groups A, B, and C (two or more compounds in total), It is more preferable to use a combination of at least one compound selected from each of the three groups A, B and C (a total of three or more compounds).

[0038] The amount of the deterioration odor masking compound used in the present invention (for example, the content of the deterioration odor masking agent of the present invention relative to the target product) may be an amount that exhibits a deterioration odor masking effect, specifically, The concentration of each of the masking agent compounds in the target product as a whole is It is preferable to use it so that the concentration is within the range of 0.00001 ppb to 100,000 ppb. It is more preferable to use it so that the concentration is within the range of 0.00005 ppb to 50,000 ppb, and It is more preferable to use it so that the concentration is within the range of 0.0001 ppb to 10000 ppb. The above-mentioned amount is preferred from the viewpoint of providing a masking effect when an odor of deteriorated oils and fats occurs and / or adheres, while minimizing the effect on the original flavor, etc. of the target product. In addition, when a masking agent compound belonging to Group A is used, the total concentration of the masking agent compound belonging to Group A in the entire target product is It is preferable to use it in the range of 0.0001 ppb to 100,000 ppb. It is more preferable to use it in the range of 0.0005 ppb to 50,000 ppb, and It is more preferable to use it so that the concentration is within the range of 0.001 ppb to 10,000 ppb. In addition, when a masking agent compound belonging to group B is used, the total concentration of the masking agent compound belonging to group B in the entire target product is It is preferable to use it so that the concentration is within the range of 0.00001 ppb to 100,000 ppb. It is more preferable to use it so that the concentration is within the range of 0.00005 ppb to 50,000 ppb or 0.001 ppb to 100 ppb, and It is more preferable to use it so that the concentration is within the range of 0.0001 ppb to 10000 ppb. In addition, when a masking agent compound belonging to group C is used, the total concentration of the masking agent compound belonging to group C in the entire target product is It is preferable to use it in the range of 0.0001 ppb to 100,000 ppb. It is more preferable to use it in the range of 0.0005 ppb to 50,000 ppb, and It is more preferable to use it so that the concentration is within the range of 0.001 ppb to 10,000 ppb. In addition, the total concentration of the masking agent compound in the entire target product is It is preferable to use it so that the concentration is within the range of 0.00001 ppb to 100,000 ppb. It is more preferable to use it so that the concentration is within the range of 0.00005 ppb to 50,000 ppb, and It is more preferable to use it so that the concentration is within the range of 0.0001 ppb to 10000 ppb.

[0039] By using one or more compounds selected from the group consisting of Group A, Group B, and Group C, the present invention makes it possible to mask the odor of deteriorated oils and fats easily, safely, and without affecting the aroma and / or taste of the final product at each stage of the production, distribution, storage, sale, etc. of the target product.

[0040] The deterioration odor masking agent of the present invention may contain compounds other than the masking agent compound. The form of the deterioration odor masking agent of the present invention and the type and amount of the other compounds can be appropriately set according to the usage mode of the deterioration odor masking agent of the present invention.

[0041] The deterioration odor masking agent of the present invention may consist of the masking agent compound alone, or may contain a suitable diluent (thickener) or carrier in addition to the masking agent compound. In this case, the ratio of the masking agent compound in the deterioration odor masking agent can be appropriately set and adjusted within the range of 0.000001 to 99 mass% (0.01 to 990000 ppm) so that the deterioration odor masking agent exerts the effect of suppressing the oil and fat deterioration odor.

[0042] The diluent or carrier used in combination with the masking agent compound is not particularly limited as long as it does not impair the oil and fat deterioration odor suppressing action of the masking agent compound. Examples include solid diluents or carriers such as gum arabic, dextrin, cyclodextrin, glucose, sucrose, etc.; or liquid diluents or carriers such as water, ethanol, propylene glycol, glycerin, glycerin fatty acid esters, edible oils and fats. These diluents or carriers include additives used to prepare the deterioration odor masking agent of the present invention into a desired shape (form), such as excipients, binders, disintegrants, emulsifiers, dissolving agents, thickeners, lubricants, flavoring agents, colorants, antioxidants, etc. Among them, emulsifiers can be suitably used to prepare an aqueous solution (dispersion, suspension) or emulsion-like deterioration odor masking agent by dispersing the masking agent compound in a liquid diluent. Examples of such emulsifiers include, but are not limited to, sucrose fatty acid esters, glycerin fatty acid esters, sorbitan fatty acid esters, lecithin, enzymatically decomposed lecithin, Quillaja extract, saponin, polysorbate, gum arabic, and gum ghatti. By using such diluents or carriers, the deterioration odor masking agent of the present invention can be made into any dosage form, such as liquid, suspension, emulsion, paste, powder, granule, and others. The dosage form of the deterioration odor masking agent of the present invention can be appropriately set according to the type and shape of the object for which the deterioration odor of oils and fats is to be suppressed.

[0043] In addition, the deterioration odor masking agent of the present invention may be prepared as a powder formulation by mixing an excipient such as dextrin with an aqueous solution in which the above-mentioned masking agent compound is dissolved or dispersed, and powdering the mixture according to a standard method such as spray drying or freeze drying, or may be prepared as a granular formulation by further granulating the mixture.

[0044] The deterioration odor masking agent of the present invention may be a fragrance composition containing, as a fragrance component, one or more of the masking agent compounds described above, or may be a fragrance composition containing, in addition to the masking agent compound, one or more other fragrance components (fragrance components other than the masking agent compound).

[0045] Such other fragrance components are not required to impair the effect of the present invention when used in combination with the above-mentioned masking agent compound, and are preferably not adversely affected by the fragrance tone of the target product in which the deterioration odor masking agent is blended. Examples of such fragrance components include those listed in "Patent Office Publication: Well-Known and Commonly Used Technology Collection (Fragrances) Part II Food Fragrances" edited by the Japan Patent Office (January 14, 2000) and "Patent Office Publication: Well-Known and Commonly Used Technology Collection (Fragrances) Part II Food Fragrances" ... Examples of such natural and synthetic flavors include those listed in the "Fragrances of Citrus Fruits" (pages 88-135), which have the scent of citrus fruits (orange, lemon, lime, grapefruit, yuzu, sudachi, etc.), and those with the scent of fruits other than citrus fruits (apple, grapefruit, etc.). fruit-based flavors having the aroma of strawberries, strawberries, bananas, peaches, melons, apricots, plums, cherries, berries, etc. (pages 136-257); milk-based flavors having the aroma of dairy products (milk flavor, butter flavor, cheese flavor, cream flavor, yogurt flavor, etc.) (pages 258-347); vanilla-based flavors having the aroma of vanilla beans (pages 348-366); tea-based flavors having the aroma of green tea, oolong tea, black tea, etc. (pages 367-426); cocoa and chocolate flavors having the aroma of cocoa or chocolate (pages 427-446); Heat-based flavors (pages 447-475), mint-based flavors having the aroma of peppermint or spearmint (pages 476-495), spice-based flavors having the aroma of spices (pages 496-580), nut-based flavors having the aroma of nuts such as almonds (pages 581-608), Western liquor-based flavors having the aroma of Western liquor (e.g. wine, whiskey, brandy, rum, gin, liqueur, etc.) (pages 759-825), flower-based flavors having the aroma of flowers (pages 826-836), vegetable-based flavors having the aroma of vegetables (e.g. onion, garlic, green onion, carrot, burdock, shiitake mushroom, matsutake mushroom, mitsuba, etc.) (pages 837 (Page 907) and the like. Preferred are citrus fragrances, fruit fragrances, Examples of flavors include milk flavors, cocoa / chocolate flavors, mint flavors, and vegetable flavors.

[0046] The fragrance composition of the present invention may contain one or more of the above-mentioned masking agent compounds in a proportion of 0.000001 to 99% by mass, as long as the effects of the present invention are achieved. When the fragrance composition of the present invention contains other fragrance components in addition to the above-mentioned masking agent compounds, the blending proportion of the other fragrance components is, without limitation, 0.000001 to 99% by mass, preferably 0.00001 to 10% by mass.

[0047] The timing and method for adding or applying the deterioration odor masking agent of the present invention or a preparation containing the same to a target product are not particularly limited, and it may be added or applied at any stage during the production of the target product.

[0048] For example, the deterioration odor masking agent of the present invention, or a formulation containing the same, may be added or applied in advance to the raw materials of the target product, and then the raw materials may be added or applied to the target product, thereby adding or applying the deterioration odor masking agent of the present invention to the target product.

[0049] The deterioration odor masking agent of the present invention can also be used in products containing various commonly used food ingredients.

[0050] Examples of the food ingredients include carbohydrates, sweeteners, thickeners, emulsifiers, vitamins, milk, dairy products, oils and fats, acidulants, flavorings, starch, dextrin, glycerin, eggs, and colorings. More specifically, the food ingredients include, for example, Carbohydrates such as sucrose, glucose, fructose, palatinose, xylose, starch syrup and maltose; Sugar alcohols such as sorbitol, xylitol, erythritol, palatinit, and reduced starch syrup; High-intensity sweeteners such as aspartame, thaumatin, sucralose, acesulfame potassium, and stevia; Thickening agents such as agar, gelatin, carrageenan, guar gum, xanthan gum, pectin, locust bean gum, galactomannan, glucomannan and gellan gum; Emulsifiers such as sucrose fatty acid esters, glycerin fatty acid esters, sorbitan fatty acid esters, and lecithin; Vitamins such as Vitamin A, B vitamins, Vitamin C, and Vitamin E; Milk, including raw milk, cow's milk, skimmed milk, and processed milk; Dairy products such as fermented milk, concentrated milk, condensed milk, whole milk powder, skim milk powder, cream, cheese, and butter; acidulants such as citric acid, malic acid, tartaric acid, and lactic acid; Fragrances exemplified in "Other Fragrances" above etc. can be mentioned.

[0051] In addition, the method for masking the odor of deteriorated oils and fats of the present invention, the method for producing an oil-containing product of the present invention, and the oil-containing product of the present invention can be understood from the above-mentioned explanation of the oil-deteriorated odor masking agent of the present invention, etc. EXAMPLES

[0052] The present invention will now be described in detail with reference to the following examples, but the present invention is not limited to these examples in any way.

[0053] In the following examples, amounts and concentrations may be based on mass unless otherwise specified.

[0054] Experimental Example 1 (Identification of major odorous substances) The main odorous substances in the odor of deteriorated oils were identified according to the procedure described below.

[0055] (Preparation of oils and fats containing aged odor) One liter of commercially available corn oil was placed in a heat-resistant container and heated at 170 to 180° C. for 30 minutes while stirring appropriately to prepare corn oil having a deteriorated oil odor.

[0056] (Identification of the main odorous substances in the odor of deteriorated oils and fats) The corn oil having the odor of aged oil prepared as described above was analyzed by GC / O, and it was confirmed that the main odorous substances in the odor of aged oil were three compounds: trans-4,5-epoxy-(E)-2-decenal, 1-octen-3-one, and (E,E)-2,4-decadienal. The measurement conditions for GC / O are as follows: GC / O equipment: 6890N (Agilent Technologies) / CharmAnalysis(TM) (Datu) Column: DB-WAX / length 15m, inner diameter 0.32mm (Agilent Technologies) Column temperature conditions: 40 to 230°C, 6°C / min heating Carrier gas: Helium.

[0057] Example 1 (Masking effect of the odor of deteriorated oils and fats in paper-packaged beverages (1)) <Preparation of a paper-packed beverage with an odor of deteriorated oil and fat> One liter of commercially available corn oil was placed in a heat-resistant container and heated at 170 to 180° C. for 30 minutes while stirring appropriately to prepare corn oil having a deteriorated oil odor. In a sealable plastic container (230mm x 320mm x H190mm), two plastic cups (top diameter 70mm) containing 100g of heat-treated corn oil and one commercially available paper pack were placed. A peach juice drink (1% fruit juice, 1000 ml volume) was placed in the container and the container was sealed. Separately, a sealed plastic container was prepared containing only the paper-packaged peach juice drink. The plastic containers prepared above were stored in a refrigerator at 5° C. for 3 days. The peach juice beverage stored with the heat-treated corn oil was used as a control, and the beverage stored with only the peach juice beverage was used as a standard.

[0058] <Preparation of beverages for evaluation> To the control product prepared above, the masking agent components shown in Table 1, which had been dissolved in 95% ethanol in advance, were added so that the final concentration in the beverage was the amount shown in Table 1 (the concentration units in the table are ppb).

[0059] The control product to which no masking agent was added was given a score of "Strongly detectable odor of deteriorated oils: 4 points" and the standard product was given a score of "No detectable odor of deteriorated oils: 0 points." The following evaluation criteria were set, and a sensory evaluation was conducted on the masking effect of the control product to which a masking agent was added against the odor of deteriorated oils. The sensory evaluation was conducted by seven panelists well trained in the sensory evaluation of odors, and the average evaluation scores are shown in Table 1: <Evaluation criteria> Strong smell of deteriorated oil: 4 points Slightly strong smell of deteriorated oil: 3 points Smell of deteriorated oil: 2 points Slight smell of deteriorated oil: 1 point No smell of deteriorated oil: 0 points <Evaluation Results>

[0060] [Table 1]

[0061] Example 2 (Masking effect of oil deterioration odor on paper-packaged beverages (2)) "Paper carton peach juice drink" replaced with "Paper carton apple juice drink (100% juice)" The masking effect was evaluated in the same manner as in Example 1 above, except that a masking agent was used, storage in a 5°C refrigerator was changed to 5 days, and the masking agent added to the control product was changed to the components and amounts shown in Table 2. The results are shown in Table 2.

[0062] [Table 2]

[0063] Example 3 (Masking effect against the oily odor of fried chicken) <Preparation of fried chicken> Fried chicken was prepared according to the recipe in Table 3 below. Specifically, the batter liquid was prepared by mixing the raw materials other than water, adding water, and mixing with a stirrer. The pickle liquid was prepared by adding the raw materials other than water to water and mixing with a stirrer. Then, 100g of chicken breast meat cut into about 15g size and 30g of pickle liquid were placed in a tumbler, tumbled for 1 hour, and then left to stand in a refrigerator for 1 hour. After removing the excess pickle liquid, the total weight of the chicken meat and pickle liquid was 115g. The pickle liquid-impregnated chicken meat was battered with the batter liquid, and then fried in corn oil (J-Oil Mills) at 170 to 175°C for 3 minutes to prepare fried chicken. The amount of batter liquid attached to the chicken meat was 20g per 100g of chicken meat. The prepared fried chicken was left to stand at room temperature for 24 hours to promote oxidation of the oil.

[0064] [Table 3]

[0065] *Esprogen KAM4: Meat quality improver / manufactured by San-Ei Gen F.F.I. Co., Ltd. *PO-30: Sugar alcohol / Mitsubishi Corporation Foodtech Co., Ltd.

[0066] [Table 4]

[0067] A control product to which no masking agent was added was fried and then left to stand at room temperature for 24 hours, and given a score of "strong odor of deteriorated oils: 4 points," and a control product to which no masking agent was added was fried and then left to stand at room temperature for 30 minutes, and given a score of "no odor of deteriorated oils at all: 0 points." The following evaluation criteria were set, and a sensory evaluation was conducted on the masking effect of the masking agent on the odor of deteriorated oils. The sensory evaluation was conducted by seven panelists well trained in the sensory evaluation of odors, and the average scores are shown in Table 5. <Evaluation criteria> Strong smell of oxidized oil: 4 points Slightly strong oxidized oily smell: 3 points Oxidized oily smell: 2 points Slightly smells of oxidized oil: 1 point No oxidized oily smell: 0 points

[0068] [Table 5]

[0069] Example 4 (Masking effect on the odor of deteriorated oil in foods containing oil and fat) <Preparation of whole milk powder solution> An aqueous whole milk powder solution was prepared by adding 90 parts by mass of ion-exchanged water to 10 parts by mass of whole milk powder (Megmilk Snow Brand Co., Ltd.).

[0070] <Preparation of whole milk powder solution containing masking agent> 0.1 parts by mass of the masking agent solution shown in Table 6 below was mixed with 100 parts by mass of the whole milk powder aqueous solution described above to prepare a whole milk powder aqueous solution containing a masking agent.

[0071] [Table 6]

[0072] The whole milk powder solution to which no masking agent was added was rated as "strongly smelling the smell of deteriorated oils and fats: 4 points" and commercially available milk to which no masking agent was added was rated as "no smell of deteriorated oils and fats at all: 0 points." The following evaluation criteria were set, and a sensory evaluation was carried out on the masking effect of the masking agent in masking the smell of deteriorated oils and fats. The sensory evaluation was carried out by seven panelists well trained in the sensory evaluation of odors, and the average evaluation scores are shown in Table 7. In addition, in all tests, the smell of the masking agent compound itself was not detected. <Evaluation criteria> Strong smell of oxidized oil: 4 points Slightly strong oxidized oily smell: 3 points Oxidized oily smell: 2 points Slightly smells of oxidized oil: 1 point No oxidized oily smell: 0 points

[0073] [Table 7]

[0074] Example 5 (Masking effect of the smell of deteriorated oil in potato chips) <Preparation of Potato Chips Containing Masking Agent> 20 g of commercially available potato chips (lightly salted flavor / Calbee Inc.) were placed on a paper plate so that they did not overlap each other. 2 g of the masking agent solution in Table 8 below was sprayed evenly onto the potato chips using a spray bottle. The samples were then left to stand at room temperature for 24 hours together with potato chips (control products) that had not been sprayed with the masking agent solution to allow the oil to oxidize.

[0075] [Table 8]

[0076] Potato chips (control products) that had not been sprayed with a masking agent were opened and left to stand at room temperature for 24 hours, and were scored as "strongly smelling the odor of deteriorated oils and fats: 4 points," while control products that were opened and left to stand at room temperature for less than 10 minutes were scored as "no smell of deteriorated oils and fats at all: 0 points." The following evaluation criteria were set, and a sensory evaluation was conducted on the masking effect of the masking agent in masking the odor of deteriorated oils and fats. The sensory evaluation was conducted by seven panelists well trained in the sensory evaluation of odors, and the average evaluation scores are shown in Table 9. In addition, in all tests, the odor of the masking agent compound itself was not detected. <Evaluation criteria> Strong smell of oxidized oil: 4 points Slightly strong oxidized oily smell: 3 points Oxidized oily smell: 2 points Slightly smells of oxidized oil: 1 point No oxidized oily smell: 0 points

[0077] [Table 9]

[0078] From the results of Examples 1 to 5 above, it was found that the masking agent compounds (styrallyl alcohol, benzyl alcohol, ethyl pyruvate, γ-butyrolactone, methyl jasmonate, methyl dihydrojasmonate, 1,8-cineole, dihydroactinidiolide, rose oxide, β-damascenone, anethole, sclareolide, menthone, 1,4-cineole, and 6-methyl-5-hepten-2-one) can effectively mask the odor of deteriorated oils and fats. In the above experimental examples, the range of evaluation points (difference between maximum and minimum values) given by the panelists for the same sample was 0 or 1 for many samples, and was within the range of 0 to 2 for all samples.

Claims

1. An oil / fat deterioration odor masking agent containing at least one compound selected from the group consisting of styrallyl alcohol, benzyl alcohol, ethyl pyruvate, γ-butyrolactone, methyl jasmonate, methyl dihydrojasmonate, 1,8-cineole, dihydroactinidiolide, rose oxide, β-damascenone, anethole, sclareolide, menthone, 1,4-cineole, and 6-methyl-5-hepten-2-one.

2. The masking agent according to claim 1, comprising at least two compounds selected from the following group: Styrallyl alcohol, benzyl alcohol, ethyl pyruvate, γ-butyrolactone, methyl jasmonate, methyl dihydrojasmonate, 1,8-cineole, dihydroactinidiolide, rose oxide, β-damascenone, anethole, sclareolide, menthone, 1,4-cineole, and 6-methyl-5-hepten-2-one.

3. A method for masking the odor of oil and fat deterioration, comprising adding the masking agent according to claim 1 or 2 to a product that may emit the odor of oil and fat deterioration.

4. A method for producing an oil-containing product, comprising adding the masking agent according to claim 1 or 2 to the oil-containing product.

5. An oil-containing product comprising the masking agent according to claim 1 or 2.

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