JP6076037B2 - Flavor improver of soy sauce or soy sauce flavoring agent - Google Patents

Description

  The present invention is a soy sauce or soy sauce flavor imparting agent characterized by containing dithioether as an active ingredient, a soy sauce flavor improving method for foods and beverages characterized by adding a specific amount of the flavor improving agent, It is related with the food / beverage products containing the flavor composition which contains a flavor improving agent, and the soy sauce or the soy sauce flavor improving agent to which the said flavor improving agent was added.

Soy sauce is also called an all-purpose seasoning because of its versatility, and it is one of the essential seasonings for the Japanese table. In addition, because of the recent healthy food and Japanese food boom, its use is not limited to Japan. It is widely used overseas as Soy Sauce.
Japanese soy sauce is a fermented, salt-containing soy food that has been decomposed with the enzymes of soybeans, proteins, lipids, and carbohydrates, which are components of soybeans and wheat, and then fermented and aged with yeast and lactic acid bacteria. Therefore, soy sauce flavor is composed of many components, and more than 300 kinds of compounds have already been identified. Many of these ingredients are involved in the flavor, creating a unique, complex and delicate flavor.

  Most of the soy sauce produced in Japan is of the thick soy sauce type, and in recent years, the main brewing soy sauce produced using almost the same amount of soybean and wheat has been increasing. The flavor of this brewed soy sauce is affected by various factors such as sugars, alcohol, organic acids, esters, carbonyl compounds, lactic acid bacteria in the manufacturing process, fermented products by yeast, and component changes during ripening. Is given. For example, homofuronol (HEMF) and 4-ethyl-2-methoxyphenol, which are important aroma components of soy sauce, are produced by the action of yeast during fermentation. Furthermore, it is said that the component which determines the characteristic flavor of this brewed soy sauce is produced by the browning reaction (amino acid and sugar Maillard reaction) caused by heating.

Soy sauce or processed soy sauce products manufactured by traditional manufacturing methods are processed to a high degree according to the purpose of cooking due to the diversification of demand in recent years, and various soy sauces such as soy sauce flavored seasonings and soy sauce with reduced salt treatment Flavored foods and drinks are manufactured and sold.
In addition, homofuronol, furaneol (HDMF), norfuraneol (HMMF), 4-ethyl-2-methoxyphenol, 4-ethylphenol, methionol, maltol, 2- Artificial soy sauce flavoring agents obtained by selecting and combining methoxy-4-vinylphenol, methional, 3-hydroxy-4,5-dimethyl-2 (5H) -furanone and the like are also used.
However, processed foods and drinks that use soy sauce may not completely satisfy the consumer's needs because some of the soy sauce flavor may be altered or lost depending on the processing method and degree, and soy sauce's original flavor may deteriorate. Is the current situation. Moreover, the soy sauce flavor imparting agent combining only the characteristic flavor components of soy sauce has a problem that it does not reach the original flavor of soy sauce.

  On the other hand, various methods have been proposed to improve the soy sauce flavor. For example, a method of adding and enhancing the rich taste by adding an acidic insoluble fraction of livestock meat and seafood extract to food and drink (Patent Document 1), a method of adding an amino acid derivative to food and drink and adding thickness to the taste (Patent Document) 2), a seasoning (Patent Document 3) that has a soy sauce feeling composed of sodium, potassium, isoleucine and methionine has been proposed.

  However, the above-described method for improving the soy sauce flavor can sufficiently meet the demand for soy sauce flavored foods and drinks that have the original flavor of brewed soy sauce with a natural and rich fermented and matured taste that matches the natural orientation of consumers. It was not a thing.

Japanese Patent Laid-Open No. 9-94076 JP-A-8-143551 JP 2011-45247 A

  The object of the present invention is to restore the original flavor of soy sauce immediately after production to soy sauce that has been taste-degraded in the processing stage, and the flavor of soy sauce or soy sauce flavoring agent for imparting the preferred flavor of soy sauce that suits consumer preferences Furthermore, a soy sauce flavor improving method for foods and beverages to which a specific amount of the flavor improving agent is added, a flavor composition comprising the flavor improving agent and a food flavor, and the flavor improving agent are added. To provide food and drink containing soy sauce or soy sauce flavoring agent.

  The present inventors have studied in detail the aroma and flavor characteristics of dithioether, and found that it has an effect of imparting a rich fermented feeling and aging feeling of soy sauce, and further, the present inventors can use various dithioethers alone or Discovered the new fact that a rich amount of fermentation and ripening can be provided by adding a very small amount to the soy sauce flavored food and drink by combining a plurality of them, and the present invention has been completed. It came to do.

That is, the present invention is as follows.
[1] The following general formula (1)
R ₁ -SS-R ₂ (1)
(Wherein R ₁ is methyl, furfurylmethyl or 2-methyl-3-furyl, and R ₂ is furfurylmethyl or 2-methyl-3-furyl). It is the flavor improving agent of the soy sauce or soy sauce flavor imparting agent characterized by the above-mentioned.
Preferably, the dithioether is a compound selected from the group consisting of furfuryl methyl disulfide, methyl 2-methyl-3-furyl disulfide, difurfuryl disulfide and bis (2-methyl-3-furyl) disulfide.

[2] A method for improving the soy sauce flavor of foods and drinks containing soy sauce or a soy sauce flavoring agent, furfuryl methyl disulfide, methyl 2-methyl-3-furyl disulfide, difurfuryl disulfide or bis (2-methyl-3-furyl) ) A method for improving the soy sauce flavor of foods and drinks, wherein disulfide is added to the foods and drinks in a concentration range of 0.001 ppt to 10 ppt.

[3] In the method for improving the soy sauce flavor of food and drink by adding the flavor improver to food and drink containing soy sauce or soy sauce flavor imparting agent, dithioether is added to the food and drink in a concentration range of 0.001ppt to 10ppt, And the concentration ratio of dithioether and soy sauce or homofuronol derived from a soy sauce flavor imparting agent is added in a concentration range of 1: 50000000-1: 5000000.

[4] A flavor composition for foods and drinks having a soy sauce flavor, wherein the flavor improver is added to a food flavor in a concentration of 0.1 ppt to 100 ppb.

[5] A method for improving the soy sauce flavor of a food or drink, comprising adding 0.01% by mass to 1% by mass of the above flavoring composition to a food or drink containing soy sauce or a soy sauce flavoring agent.

[6] A food or drink containing soy sauce or a soy sauce flavoring agent, wherein furfuryl methyl disulfide, methyl 2-methyl-3-furyl disulfide, difurfuryl disulfide or bis (2-methyl-3-furyl) disulfide is 0. A food or drink containing soy sauce or a soy sauce flavoring agent, which is added in a concentration range of 0.001 ppt to 10 ppt.

When the flavor improver or flavor composition of the present invention is used in soy sauce flavored foods and drinks, the soy sauce that has been taste-degraded in the processing stage is restored to the original flavor of the soy sauce immediately after production, and the soy sauce that suits consumer preferences A soy sauce-flavored food or drink having a preferred flavor, that is, a rich fermented and matured soy sauce can be provided to consumers.
In addition, a soy sauce flavor-imparting agent that combines only the characteristic flavor components of soy sauce can give a rich fermented or matured sensation that reaches the soy sauce flavor of this brew.

フルフリルメチルジスルフィド、メチル２−メチル−３−フリルジスルフィド、ジフルフリルジスルフィド又はビス（２−メチル−３−フリル）ジスルフィドは、香料や試薬として市販されている。本発明においては、市販品を適宜購入して使用することができる。
また、上記のジチオエーテル類である限り、異なる化合物２種以上を併用することができる。本発明においては、市販品あるいは合成品を使用することができる。 Hereinafter, the present invention will be described in detail according to embodiments.
[1] Flavor improver (1) active ingredient The active ingredient of the flavor improver of the present invention is represented by the following general formula (1)
R ₁ -SS-R ₂ (1)
(Wherein R ₁ is methyl, furfurylmethyl or 2-methyl-3-furyl, and R ₂ is furfurylmethyl or 2-methyl-3-furyl).
Preferably, the dithioether of the formula (1) is furfuryl methyl disulfide (the following compound (a)), methyl 2-methyl-3-furyl disulfide (the following compound (b)), difurfuryl disulfide (the following compound). (c)) or bis (2-methyl-3-furyl) disulfide (the following compound (d)).

Furfuryl methyl disulfide, methyl 2-methyl-3-furyl disulfide, difurfuryl disulfide or bis (2-methyl-3-furyl) disulfide are commercially available as perfumes and reagents. In the present invention, commercially available products can be purchased and used as appropriate.
Moreover, as long as it is said dithioether, 2 or more types of different compounds can be used together. In the present invention, commercially available products or synthetic products can be used.

The dithioethers that are the active ingredients of the present invention are known as perfume compounds. For example, furfurylmethyl disulfide is present in pork liver and the like, has a white bread skin aroma, and is used in soups and the like. .
In addition, difurfuryl disulfide has a caramel-like roasted aroma, exists in coffee and the like, and is used for coffee flavor and the like.
In addition, methyl 2-methyl-3-furyl disulfide has sulfur-like, meat-like, medium-like, and roasted flavors and is used as a flavor for meat, onion, and seasoning (Motoichi Indo, “Synthetic Fragrance-Chemical And product knowledge ", 1996, see Chemical Industry Daily Inc.).
In addition, one or more compounds selected from the group consisting of furfurylmethyl disulfide, methyl 2-methyl-3-furyl disulfide, difurfuryl disulfide and bis (2-methyl-3-furyl) disulfide are milk-related. There is a proposal to impart and enhance the natural feeling, freshness, and richness of milk to products (Japanese Patent Laid-Open No. 2008-92890). However, it has not been known that the above-mentioned dithioethers have a flavor improving effect on foods and drinks having a soy sauce flavor at a very small concentration.

(2) Subject of flavor improvement The flavor improver of the present invention is soy sauce, especially soy sauce with a deteriorated flavor, that is, flavouring, deodorizing or being added to food and drink to enhance sterilization and storage. It is effective in improving the flavor of soy sauce, in which a part of the aroma and flavor is altered and lost due to heating in the production process of food and drink and freezing means in the production process of frozen food.
Moreover, when it adds to the soy sauce which is not processed, it is effective and can further improve the original flavor of soy sauce.
Japanese soy sauce depends on the manufacturing method, raw materials, characteristics, etc., depending on the production method, raw materials, characteristics, etc., “Kokuchi soy sauce”, “Usukuchi soy sauce”, “Tamari soy sauce”, “Re-filled soy sauce”, “White” The flavor improving agent of the present invention is particularly remarkable for the flavor improving effect of brewed thick soy sauce.

The flavor improving agent of the present invention has the effect of enhancing the original soy sauce flavor by applying it to a material that has expressed the soy sauce flavor to some extent. Therefore, it is effective for artificial soy sauce flavoring agents that are prepared by selecting characteristic aroma components from a wide variety of soy sauce flavors, making artificial soy sauce-like flavors rich in the flavors of brewed soy sauce. It can also be improved to reach.
Such a soy sauce flavoring agent has a typical and characteristic flavor component homofuronol as a main component, and other soy sauce flavor components furaneol, norfuraneol, 4-ethyl-2-methoxyphenol, 4-ethylphenol, methionol. , Maltol, 2-methoxy-4-vinylphenol, methional, 3-hydroxy-4,5-dimethyl-2 (5H) -furanone and the like are generally blended as appropriate.

Here, homofuronol (also known as homofuraneol) is 2 (or5) -ethyl-4-hydroxy-5 (or2) -methyl-3 (2H) -furanone [HEMF]) of each structure. It is a characteristic scent component of brewed soy sauce that has been proven as a natural product for the first time from Japanese brewed soy sauce, and has a sweet caramel flavor associated with soy sauce. In addition to soy sauce, it has been confirmed to be present in coffee, strawberry and miso. The aroma is strong, the threshold in water is 0.04 ppb or more, and the abundance in soy sauce is 50 to 100 ppm.

(3) Addition amount of flavor improver The flavor improver of the present invention is generally added in a concentration range of 0.001 ppt to 10 ppt to food and drink containing soy sauce or soy sauce flavor-imparting agent.
Since dithioether as an active ingredient has a slight difference in the improvement effect depending on the type of substituent, it is preferable to define a more specific addition amount for each compound.
That is, when using furfuryl methyl disulfide, methyl 2-methyl-3-furyl disulfide, difurfuryl disulfide or bis (2-methyl-3-furyl) disulfide as a flavor improver, the amount added to the soy sauce flavored food or drink is The addition concentration is in the range of 0.001 ppt to 10 ppt, preferably 0.01 ppt to 1 ppt.
When the addition amount is less than 0.001 ppt, the flavor improving effect may not be sufficient, while when the addition amount exceeds 10 ppt, the flavor of the compound may be raised.

More strictly speaking, the soy sauce flavor depends on the concentration of soy sauce or soy sauce flavoring agent contained in the food or drink. Therefore, it is reasonable to define the addition amount of the flavor improving agent based on homofuronol, which is a characteristic aroma component contained in soy sauce and is the main component of an artificial soy sauce flavor imparting agent.
That is, in a concentration range in which the concentration ratio of dithioether to soy sauce or homofuronol derived from soy sauce flavoring agent (dithioether: homofuronol) is 1: 50000000-1: 5000000, particularly 1: 500000000-1: 50000000. It is preferred to add dithioether.

(4) Additional components and dosage form of flavor improver In addition to the active ingredient dithioether, other components commonly used for food and drink, such as sweeteners, colorants, preservatives, thickening stabilizers , Antioxidants, bitters, acidulants, emulsifiers, reinforcing agents, manufacturing agents, excipients, disintegrants, binders, lubricants, coating agents, plasticizers, etc. Can also be used.
The flavor improver can be used as it is in liquid form, but it can also be made into powder by spray drying by adding excipients (dextrin, etc.), and various dosage forms should be adopted depending on the application. Can do.

[2] Flavoring Composition A flavor improving composition containing the dithioether of the present invention as an active ingredient is added to one or more general-purpose food flavors and mixed in a conventional manner to prepare a flavoring composition. It can also be used by adding it to food and drink.
That is, the flavor improving agent of the present invention can be used alone in a soy sauce flavored food or drink, and can be added as an optional component to a soy sauce flavoring agent or other food flavors.
As a soy sauce flavoring agent, homofuronol is a main component, and 4-ethyl-2-methoxyphenol, 4-hydroxy-2,5-dimethyl-3 (2H) -furanone, 2-methoxy-4-vinylphenol, methional, and A flavor composition containing 3-hydroxy-4,5-dimethyl-2 (5H) -furanone can be exemplified.
Moreover, as a fragrance | flavor for foodstuffs, the following natural or synthetic fragrance | flavors can be illustrated, for example.

Ethyl acetoacetate, acetophenone, anisaldehyde, α-amylcinnamaldehyde, methyl anthranilate, ionone, isoeugenol, isoamyl isovalerate, ethyl isovalerate, allyl isothiocyanate, 3-butenyl isothiocyanate, 4-pentenyl isothiocyanate, Benzyl isothiocyanate, 3-methylthiopropyl isothiocyanate, isothiocyanates, indole and its derivatives, γ-undecalactone, esters, ethyl vanillin, ethers, eugenol, octanol, octanal, ethyl octoate, isoamyl formate, geranyl formate , Citronellyl formate, cinnamic acid, ethyl cinnamate, methyl cinnamate, ketones, geraniol, isoamyl acetate, ethyl acetate,

Geranyl acetate, cyclohexyl acetate, citronellyl acetate, cinnamyl acetate, terpinyl acetate, phenethyl acetate, butyl acetate, benzyl acetate, l-menthyl acetate, linalyl acetate, methyl salicylate, allyl cyclohexylpropionate, citral, citronellal, citronellol, 1,8- Cineol, fatty acids, higher aliphatic alcohols, higher aliphatic aldehydes, higher aliphatic hydrocarbons, cinnamyl alcohol, cinnamaldehyde, thioethers, thiols, decanal, decanol, ethyl decanoate, terpineol, limonene, pinene , Myrcene, tapinolen, terpene hydrocarbons, γ-nonalactone, vanillin, paramethylacetophenone, hydroxycitronellal, hydroxycitronellal dimethylacetal, Peronaru,

Isoamyl phenylacetate, isobutyl phenylacetate, ethyl phenylacetate, phenol ethers, phenols, furfural and derivatives thereof, propionic acid, isoamyl propionate, ethyl propionate, benzyl propionate, hexanoic acid, allyl hexanoate, ethyl hexanoate, Ethyl heptanoate, l-perilaldehyde, benzyl alcohol, benzaldehyde, aromatic alcohols, aromatic aldehydes, d-borneol, maltol, methyl N-methylanthranylate, methyl β-naphthyl ketone, dl-menthol, l-menthol Synthetic or natural flavors such as butyric acid, isoamyl butyrate, ethyl butyrate, cyclohexyl butyrate, butyl butyrate, lactones, linalool, orange, lemon, lime, grapefruit Citrus essential oils,

Fruit-based essential oils such as apple, banana, grape, melon, peach, pineapple, strawberry, or flavors such as milk, cream, butter, cheese, yogurt, flavored milk, green tea, oolong tea, tea, coffee, cocoa Mint essential oils such as flavors, peppermint, spearmint, asanomi, asafetida, ajowan, anise, angelica, fennel, turmeric, oregano, allspice, orange nope, pepper, cassia, camomil, mustard, cardamom, curry leaf, licorice , Caraway, gardenia, cumin, watercress, clove, poppy flea, caper, pepper, sesame, coriander, sassafras, saffron, savorie, salvia, salamander, perilla, cinnamon, sha Tsu door, juniper berry,

Ginger, Star Anise, Spearmint, Horseradish, Celery, Sorrel, Thyme, Onion, Tamarind, Tarragon, Chives, Dill, Pepper, Nutmeg, Scallop, Nigera, Carrot, Garlic, Basil, Parsley, Pepper, Vanilla, Paprika, Hisop Spice extract obtained from phenegrigree, peppermint, horse mint, horse radish, marjoram, ginger, lavender, linden, lemongrass, lemon balm, rose, rosemary, laurel, wasabi, Iceland moss, red pepper, akebi, Asa, Asafetida , Asian Tam, Ajowan, Azuki, Asparagus Linea Alice, Apple Mint, Artichoke, Anise, Avocado, Amateur, Amatazuru, Amiga Sayuri, Amiri , Almonds, Chenopodium ambrosioides L.,

Arcanna, Artemisia, Arnica, Alfalfa, Aloe, Angostura, Angola Weed, Apricot, Apricot, Angelica, Amber, Ambergris, Ambret, Squid, Epimedium, Rabbit, East, Plover, Strawberry, Fig, Ginkgo, Ginkgo, Iran Iran, Iwaogi, Imperatoria, Inmortel, Wintergreen, Watercress, Ukogi, Turmeric, Usbasaishin, Woodruff, Sea Urchin, Ume, Oolongcha, Egoma, Enokitake, Shrimp, Ebisugusa, Erigeron, Elder, Eletrocock, Elecanpen, Jeremi, Engosaku, Enju , Endive, European thistle, auren, plantain, casserole, krill, oak, oak moss, okera, osmanthus, opoponax, ominae , Alismataceae,

Dutch sennici, origanum, oris, olibanum, olives, allspice, orange, orange flower, chi, cainous, cacao, oysters, cassai, cashew nuts, cascara, cascarilla, castrium, bonito, bonito, cassie, cashia fistula, catechu, crab , Carnation, valerian, camomil, kayapte, mustard, crow crisp, crow biscak, guarana, calamus, galanga, currant, carissa, karin, cardamom, galvanum, curry, kawamidori, licorice, gambia, kanran, kiwifruit, kikaigaraki, kikyo garlic Jellyfish, catalpa, scallop, yellow-tailed aloe, kina, yellowfin, yellow-headed eagle, hosta, gymnema sylvestre, catnip, caraway, Yaroppu, cucumber, Quillaja,

Goldfish, guava, guayak, wolfberry, peony, kuboboke, kuzu, camphor, camphor, gooseberry, gardenia, cuber, bearberry, gummy, cumin, ground ivy, clara, clarisage, cranberry, chestnut, walnut, cream, grain of paras Detany, grapefruit, clover, clove, black moji, mulberry, quassha, caper, ghetto, cade, kebraco, gelmander, centur, kenponashi, genonosho, kouji, kodatake, kocha, kohone, coca, koganebana, kokuto, kokului, coconut , Goshyu, pepper, costas, costmary, copaipa, coffee, kobushi, burdock, sesame, cola, coriander, coltsfoot, golden rod Colombo, root vegetables,

Conzu Lango, Comfrey, Cypress, Fish, Sakura, Cherry, Pomegranate, Salmon Cass, Sasa, Sasakusa, Search, Sassafras, Saffron, Sapodilla, Cactus, Salamander, Salsaparilla, Salsify, Sarno shikake, Hawthorn, Sanshuyu, Salamander, Santa Herb, Sandalac, Sandalwood, Sandal Red, Shiitake, Gene, Perilla, Cedar, Citrus, Citronella, Sinus, Civet, Shimaruba, Shimeji, Peonies, Jasmine, Janohige, Jaborangi, Shallot, Shukusha, Juniper Berry, Ginger, Shoyu, Shoyukas, Joryushu, Shoro, Shirotamogitake, Ginseng, Cinnamon, Vinegar, Watermelon, Daffodil, Sugi, Star anise, Star fruit, Stylax, Suppo , Phallus Impudicus, Zudorabettsu,

Snake Root, Spike Nard, Spruce, Spearmint, Spruce, Slow Berry, Savory, Ginger, Sage, Zedary, Senega, Geranium, Celery, Senkyu, Centauria, Sengen, St. John's Walt, Senna, Sauce, Diou, Soy, Thyme, Bamboo Shoot , Octopus, Tade, Davana, Egg, Egg, Onion, Tamarind, Damiana, Tamogitake, Tarragon, Taranki, Tansy, Tangerine, Dandelion, Cherimola, Cherry Laurel, Cherry Wild, Chigaya, Chicory, Cheese, Chichitake, Chives, Chervil, Champaca , Tuberose, dung beetle, tilata, tsukushi, ivy, ivy, camellia, camellia, garlic carrot, tsurudukudami, diatang, thistle, Itani, dill, dates,

Ladybug, Tenma, Capsicum, Toki, Dokushokutsu Protein Sat, Dokushokutsuyu, Tomitsu, Corn, Dokudami, Tochu, Doggrass, Tomato, Dragon Blood, Dorian, Truffle, Truval Sam, Tonka, Naginata Koju, Pear, Naster Siam, Nuts , Natto, jujube, nutmeg, radish, sea cucumber, larvae, niauri, garlic, carrots, garlic, mouse potato, nettle, leeks, knotgrass, violet, pineapple, hibiscus, malt, coconut, basil, lotus, lotus cup, perth Cup, parsley, butter, butter oil, buttermilk, birch, honey, patchouli, mint, buck bean, kkoshu, hakkounyu, hakkoumieki, pa Deployment fruit, Hatsutake,

Buffalo berry, pearl barley, hanasuge, banana, vanilla, honeysuckle, papaya, barberry, clam, hamasuge, hamanasu, kingfish, hamamelis, rose, palmarosa, van litchi, hikiokoshi, hishi, pistachio, hisop, hickory, peanut, hinoki, peanut, hinoki cypress , Himehagi, hyacinth, oyster mushroom, loquat, betel nut, feijoa, fenugreek, fennel, fujibakama, fujimodoki, fusuma, fuselyu, petitgrain, butchu, grapes, grape salmon casserole, yellow peach, beech, beech, black caraway, blackberry, plum, Bryonia, Prickly Ash, Primrose, Prunella, Blueberry, Breadfruit, Hay, Bay, Hazelnut, Vetiver, Bethel, Nibana, Penny Royal,

Peppermint, snake, pepino, peptone, bergamot, bergamot mint, peru balsam, velvena, veronica, benzoin, boadrose, hoahound, hou, broomtake, shochu, bowfish, whey, honoki, horsemint, horseradish, button, hop, poppy, Poplar, popau, jojoba, squirt, bordeaux, bologna, maitake, magwalt, marshmallow, marjoram, mastic, masoy, matsutake, machiko, pine, pine moji, mushroom, matsutake, matsutake, matsuhodo, matecha, bean, marigold, maruba Daio, quince, malein, mallow, mango, mangosteen, mandarin orange, mishima psycho, miso, mitsumata, beeswax, meat, mimosa, ginger, milk, myrte, mirfu Yl, myrrh, Mirobaran, barley tea, musk, purple, mesquite, Meadow Sweet, Mehajiki,

Maple, Melissa, Merilot, Melon, Moennego, Moniria bayou, Echinome, Momo, Morohaya, Yakuchi, Yamamuro, Eucalyptus, Yukinoshita, Yuzu, Yucca, Lily, Yosai, Yoroigusa, Lionsfoot, Lychee, Life Everlasting Flower, Lime , Lilac, Lacanca, Lacancho, Raspberry, Latania, Radish, Labdanum, Lavender, Langwald, Langmoth, Rambutan, Liqueur, Leak, Lyzea, Linaroe, Longan, Ryofunso, Ryokucha, Apple, Linden, Gentian, Lou, Borage Reseda, lemon, lemongrass, forsythia, forsythia, renbu, rosemary, lobe, laurel, longosa, wasabi, cotton bud, wormwood, worm sea , Bracken, is like the illustration natural flavors derived from such burnet, are appropriately selected and used.

  In addition to the above-described flavor improver and the fragrance component, other components that are usually used for food and drink can be added to the flavor composition of the present invention. Examples of optional components used additionally include sweeteners, coloring agents, preservatives, thickening stabilizers, antioxidants, bittering agents, acidulants, emulsifiers, reinforcing agents, manufacturing agents, excipients, and disintegrating agents. , Binders, lubricants, coating agents, plasticizers, and the like, and these can be added and used as various preparations and dosage forms.

  The flavoring composition thus obtained can be used as it is in a liquid state, but it can also be made into powder by spray drying by adding excipients (dextrin, etc.). Various dosage forms can be employed.

  The addition amount of the flavor improving agent in the case of preparing a flavor composition by combining the flavor improving agent containing the dithioether of the present invention with the above-mentioned food flavor is generally different depending on the purpose or the type of the dithioether. Is 0.1ppt to 100ppb, preferably 1ppt to 10ppb of the total amount of the flavoring composition at the added concentration. When the addition amount is less than 0.1 ppt, the effect of addition may not be sufficient, and when the addition amount exceeds 100 ppb, the flavor improving agent itself may have a strong flavor.

[3] Soy sauce flavored food and drink The soy sauce flavored food and drink to which the flavor improving agent or flavor composition of the present invention is applied are a product using soy sauce and a product using a soy sauce flavoring agent.
Such soy sauce flavored foods and drinks include Japanese-style soup seasonings, Chinese seasonings, salad dressings, processed vegetables and meat, seafood, marine products (kamaboko, chikuwa, hampen, etc.), cooked foods (soba, ramen, Fried rice, etc.), prepared foods, snacks (potato chips, popcorn, etc.), snack foods (pizza, cup noodles, etc.), delicacies (noced squid, squid squid, shellfish, beef jerky, etc.), nutritional foods, frozen desserts (Ice cream, sherbet, etc.), desserts such as jelly, pudding, sheep candy, rice cakes (rice crackers, arabe etc.), confectionery such as cookies, cakes, buns, breads (confectionery bread, bread etc.) and the like.

EXAMPLES Next, although an Example is shown and this invention is demonstrated further more concretely, this invention is not limited to these Examples.
The various dithioethers used in the examples are as follows.

[Examples 1 to 3]
1 ppt, 100 ppt and 10 ppb ethanol solutions of furfurylmethyl disulfide were prepared.
0.1 mass% of this was added to the commercially available deep-mouthed soy sauce (Kikkoman company make) diluted 10 times with distilled water, and the soy sauce flavor liquids 1-3 of this invention were prepared.

[Examples 4 to 6]
1 ppt, 100 ppt, and 10 ppb ethanol solutions of methyl 2-methyl-3-furyl disulfide were prepared.
0.1 mass% of this was added to commercially available deep-mouthed soy sauce (manufactured by Kikkoman) diluted 10 times with distilled water to prepare soy sauce flavor solutions 4 to 6 of the present invention.

[Examples 7 to 9]
1 ppt, 100 ppt and 10 ppb ethanol solutions of difurfuryl disulfide were prepared.
0.1 mass% of this was added to the commercially available concentrated soy sauce (made by Kikkoman) diluted 10 times with distilled water, and soy sauce flavor liquids 7-9 of this invention were prepared.

[Examples 10 to 12]
A 1ppt, 100ppt, 10ppb ethanol solution of bis (2-methyl-3-furyl) disulfide was prepared.
0.1 mass% of this was added to commercially available concentrated soy sauce (Kikkoman Co., Ltd.) diluted 10 times with distilled water to prepare soy sauce flavor solutions 10 to 12 of the present invention.

[Comparative Example 1]
Soy sauce seasoning liquid comparative example 1 which does not contain the flavor improving agent of the present invention by blending ethanol instead of the flavor improving agent of Example 1 was prepared.

[Test Example 1]
Sensory evaluation of the soy sauce seasoning liquids of Examples 1 to 12 and Comparative Example 1 was performed by 10 skilled panels using the additive-free product as a control.
The flavor improvement effect was evaluated according to the following criteria. Table 2 shows the average value of the evaluation points.
Remarkably excellent flavor: 7 points Excellent flavor: 6 points Slightly excellent flavor: 5 points Control: 4 points Slight off-flavor odor: 3 points Off-flavor odor: 2 points Strong off-flavor odor: 1 point

[Examples 13 to 24]
Each component shown in Table 3 is adjusted to have each part by mass and mixed with a soy sauce flavoring agent and a solvent according to the formulation in Table 4 to prepare the soy sauce flavoring composition of the present invention (Examples 13 to 24). did.

なお、上記醤油香味付与剤で使用した香料成分は、以下のとおりである。

In addition, the fragrance | flavor component used with the said soy sauce flavor imparting agent is as follows.

[Comparative Example 2]
In the formulation of Table 3, a soy sauce flavoring composition of Comparative Example 2 was prepared by blending ethanol instead of the flavor improving agents of Examples 13-24.

[Test Example 2]
0.1 parts by mass of the soy sauce flavoring compositions prepared in Examples 13 to 24 and Comparative Example 2 were added to 100 parts by mass of commercially available concentrated kelp soup (Yamasa Co., Ltd.) diluted 10 times with distilled water. The kelp soup seasoning liquids of Examples 25 to 36 and Comparative Example 3 were prepared.
Next, sensory evaluation was performed by 7 skilled panelists using the additive-free product as a control.
The flavor improvement effect was evaluated according to the following criteria. Table 6 shows the average value of the evaluation points.
Remarkably excellent flavor: 7 points Excellent flavor: 6 points Slightly excellent flavor: 5 points Control: 4 points Slight off-flavor odor: 3 points Off-flavor odor: 2 points Strong off-flavor odor: 1 point

[Test Example 3] (baked rice ball sauce)
After 80 parts by weight of thick soy sauce, 10 parts by weight of mirin and 10 parts by weight of sugar were dissolved by heating and stirring, the soy sauce flavoring compositions prepared in Examples 14, 17, 20, 23 and Comparative Example 2 were each 0. .1 part by mass was added to prepare the grilled rice balls of Examples 37 to 40 and Comparative Example 4.
After baking 80-80 g of rice, 5 g of the prepared grilled rice ball was applied with a brush and dried with hot air (240 ° C., 3 minutes) to prepare each grilled rice ball. The sensory evaluation test was conducted by six professional panelists. The results are shown in Table 7.

[Test Example 4] (teriyaki sauce)
Examples 14, 17, 20, 23, and Comparative Example 2 after 40 parts by weight of soy sauce, 20 parts by weight of mirin, 24 parts by weight of sugar, 1 part by weight of salt and 15 parts by weight of distilled water were dissolved by heating and stirring. The teriyaki sauces of Examples 41 to 44 and Comparative Example 5 were prepared by adding 0.1 parts by mass of each of the flavoring compositions prepared in Step 1 and heating at 90 ° C. for 60 minutes.
A sensory evaluation test was conducted by 7 expert panelists. The results are shown in Table 8.

[Test Example 5] (Japanese style dressing)
Examples 14, 17 after stirring and homogenizing 15 parts by mass of vinegar, 5 parts by mass of fructose glucose liquid sugar, 4 parts by mass of salt, 40 parts by mass of edible fats and oils, 0.2 part by mass of lecithin and 35.7 parts by mass of distilled water. , 20, 23 and 0.1 parts by mass of the flavoring composition prepared in Comparative Example 2 were added to prepare Japanese-style dressings of Examples 45 to 48 and Comparative Example 6, respectively.
A sensory evaluation test was conducted by 8 expert panelists. The results are shown in Table 9.

[Test Example 6] (Hard Candy)
After 50 parts by weight of sugar, 30 parts by weight of starch syrup, and 16 parts by weight of water were cooked at 155 ° C., they were cooled to 120 ° C., and the flavoring compositions prepared in Examples 14, 17, 20, 23 and Comparative Example 2 were respectively used. 0.1 mass part was added, it shape | molded, and the soy sauce flavor hard candy of Examples 49-52 and the comparative example 7 was prepared.
A sensory evaluation test was conducted by 8 expert panelists. The results are shown in Table 10.

  When the flavor improving agent or soy sauce flavor flavoring composition of the present invention is used in foods and drinks, the rich fermented feeling and aging feeling of soy sauce, the volume of taste, the food and drink having a rich soy sauce flavor to consumers Can be provided.

Claims (7)

A soy sauce flavor improving agent that imparts a soy sauce fermentation and aging feeling to soy sauce or soy sauce flavoring agent,
The following general formula (1)
R ₁ -SS-R ₂ (1)
Wherein R ₁ is methyl, furfurylmethyl or 2-methyl-3-furyl, and R ₂ is furfurylmethyl or 2-methyl-3-furyl.
The above-mentioned soy sauce flavor improving agent characterized by comprising as an active ingredient a dithioether represented by the formula (excluding bis (2-methyl-3-furyl) disulfide).   The soy sauce flavor improving agent according to claim 1, wherein the dithioether is a compound selected from the group consisting of furfuryl methyl disulfide, methyl 2-methyl-3-furyl disulfide and difurfuryl disulfide. A method for improving the soy sauce flavor of a food or drink that imparts a fermented and matured feeling of soy sauce to a food or drink containing a soy sauce or soy sauce flavoring agent,
Said soy sauce characterized by adding furfuryl methyl disulfide, methyl 2-methyl-3-furyl disulfide or difurfuryl disulfide to a food or drink containing soy sauce or soy sauce flavoring agent in a concentration range of 0.001 ppt to 10 ppt. To improve the flavor. The soy sauce flavor improving agent according to claim 1 or 2 is added to a food or drink containing soy sauce or a soy sauce flavor imparting agent to improve the soy sauce flavor of the food or drink so as to impart a fermented and matured feeling of soy sauce. A method,
The dithio ether [However, bis except (2-methyl-3-furyl) disulfide] in a concentration range of 0.001ppt~10ppt to food or drink and a Homofuronoru that and from the dithioether and soy sauce or soy sauce flavorings The soy sauce flavor improving method as described above, wherein the concentration ratio is 1: 50000000000000 to 1: 5000000. The soy sauce flavor improving agent according to claim 1 or 2 is added to a food flavor in a concentration range of 0.1 ppt to 100 ppb, and soy sauce for food and drink containing a soy sauce or soy sauce flavor enhancer is used. A flavor composition that imparts a sense of maturity.   Add the 0.01% by mass to 1% by mass of the flavoring composition according to claim 5 to a food or drink containing soy sauce or a soy sauce flavor imparting agent, thereby imparting a fermented and matured feeling of soy sauce for the food or drink. To improve soy sauce flavor. A food or drink containing soy sauce or a soy sauce flavoring agent,
The above-mentioned food and drink in which furfuryl methyl disulfide, methyl 2-methyl-3-furyl disulfide or difurfuryl disulfide is added to the food and drink in a concentration range of 0.001 ppt to 10 ppt to give the soy sauce fermented and matured Goods.