WO2006087991A1

WO2006087991A1 - Taste-improving agent for sweetener having high sweetness

Info

Publication number: WO2006087991A1
Application number: PCT/JP2006/302468
Authority: WO
Inventors: Toshio Miyazawa; Tomoko Matsuda; Shuichi Muranishi; Kazuyuki Miyake
Original assignee: Ogawa & Co., Ltd.
Priority date: 2005-02-15
Filing date: 2006-02-13
Publication date: 2006-08-24
Also published as: JP4688517B2; JP2006223104A; TW200640377A

Abstract

It is intended to provide a taste-improving agent for a sweetener having a high sweetness which can effectively inhibit, even in a small amount, the bitterness, harsh taste and unpleasant aftertaste characteristic to sweeteners with high sweetness without altering the inherent flavors of foods and which can be easily produced. By adding a taste-improving agent comprising spirantol or a plant extract or a plant essential oil containing spirantol to a food or a drink containing a sweetener having a high sweetness, the unpleasant aftertaste of the sweetener having a high sweetness can be relieved. This taste-improving agent can exert its effect only in a small amount. Thus, the unpleasant aftertaste, etc. of a sweetener having a high sweetness can be relieved thereby without affecting the taste of a food or a drink.

Description

Taste improver for high-intensity sweeteners

Technical field

[0001] The present invention relates to a taste improving agent for high-intensity sweeteners. More specifically, the present invention relates to a taste improver that improves the unpleasant aftertaste, bitterness, and eda taste of high-sweetness sweeteners.

Background art

[0002] With the recent increase in health orientation, products using low-calorie high-intensity sweeteners such as aspartame, stevia, acesulfame K, and sucralose are increasing. Such a high-intensity sweetener has a sweetness several hundred times that of sucrose, but has an excellent performance, but often has a peculiar bitter taste or eda taste. Further, since the aftertaste has a long lasting sweetness, the quality of taste is inferior to that of sucrose as a result of poor taste loss. Therefore, for the general use of high-intensity sweeteners, improving the taste is the biggest issue.

[0003] For improving the taste of high-intensity sweeteners, methods using amino acids such as L-asparagine, organic acids such as dalconic acid and quenoic acid, and salts thereof (Patent Documents 1 to 3), high sweetness A method of combining sweeteners with natural products such as rutin and hesperidin (Patent Documents 4 and 5), galactmannan degradation products, and sugars such as gelooligosaccharide, beet oligosaccharide and mannose to improve the sweetness of sweeteners The methods used (Patent Documents 6 to 9) and the methods of blending plant-derived extracts such as sugarcane-derived bagasse extract and enzyme-treated yew leaf extract into high-intensity sweeteners (Patent Documents 10 and 11) are proposed. The present inventors also used a quinic acid obtained by purifying a processed product obtained by hydrolyzing coffee beans with an enzyme or an alkali as a sweet taste improver, so that Suppresses unpleasant aftertaste Proposes law (Patent Document 12). However, these existing methods cannot sufficiently reduce the unpleasant aftertaste with a small addition amount, and increasing the addition amount can change the original taste and aroma of the food or increase the sweetness level. Had the problem of complicated production of sweetness improvers

[0004] Patent Document 1: Japanese Unexamined Patent Publication No. 2000-270804 Patent Document 2: Japanese Patent Laid-Open No. 2003-210147

Patent Document 3: Japanese Patent Application Laid-Open No. 60-188035

Patent Document 4: Japanese Patent Laid-Open No. 10-146165

Patent Document 5: JP-A-8-256725

Patent Document 6: JP-A-9 19268

Patent Document 7: JP-A-10-234331

Patent Document 8: Japanese Unexamined Patent Publication No. 2000-197462

Patent Document 9: JP 2002-272411 A

Patent Document 10: Japanese Unexamined Patent Publication No. 2000-217540

Patent Document 11: Japanese Unexamined Patent Publication No. 2003-180288

Patent Document 12: Japanese Patent Laid-Open No. 2001-321115

Disclosure of the invention

Problems to be solved by the invention

[0005] The problem to be solved by the present invention is that the bitterness, eda taste and unpleasant aftertaste peculiar to high-intensity sweeteners can be effectively suppressed without changing the original flavor of the food with an added amount, and production. It is an object of the present invention to provide a taste-improving agent for high-intensity sweeteners that is easy to handle.

Means for solving the problem

[0006] As a result of repeated studies to solve the above problems, the present inventors have found that spirantol can suppress the unpleasant taste of high-intensity sweeteners, and have completed the present invention.

[0007] That is, the present invention relates to a taste improving agent for high-intensity sweeteners characterized by becoming spirantol or an extract of a plant containing spirantol or an essential oil, and further a plant containing spirantol. It is a taste improver for the above-mentioned high-intensity sweetener, which is Dutch Senchi or Kibana Dutch Senchi.

In addition, the present invention is the taste improving agent for a high-intensity sweetener, wherein the high-intensity sweetener is aspartame, sucralose, or acesulfame K.

In addition, the present invention provides the taste improver for high-intensity sweeteners, wherein the taste improving agent for high-intensity sweeteners further contains quinic acid or a hydrolyzate of coffee beans containing quinic acid as an active ingredient. It is an improving agent. In addition, the present invention provides a high-intensity sweetener that is unpleasant due to a high-intensity sweetener, characterized by adding a taste improving agent for the high-intensity sweetener to a high-intensity sweetener or a food or drink containing the high-intensity sweetener This is a method for suppressing aftertaste.

The present invention also provides a high-sweetness sweetener-containing flavor composition for foods and drinks, which comprises the high-sweetness sweetener taste improver.

Furthermore, the present invention comprises a high-intensity sweetener, which contains a high-intensity sweetener and a taste improving agent for the high-intensity sweetener, with an unpleasant aftertaste caused by the high-intensity sweetener suppressed. It is a food composition or a food or drink.

The invention's effect

[0008] The taste-improving agent for high-intensity sweeteners of the present invention can remarkably suppress the unpleasant sweetness remaining as bitterness, eda taste and aftertaste peculiar to high-intensity sweeteners when added in a small amount. Further, a complicated production process such as hydrolysis with an enzyme or alkali is unnecessary, and the production can be performed only by extraction and distillation operations.

BEST MODE FOR CARRYING OUT THE INVENTION

[0009] Spirantol used in the present invention is N-isobutyryl 1,6,8-decatrienamide represented by the following chemical formula, and is a asteraceae (Spilanthes acmella) or kibana. It is a pungent ingredient contained in Dutch senchi (Spilanthes acmella var. Oleracea).

CH CH = CH-CH = CH (CH) CH = CHCONHCH CH (CH)

3 2 2 2 3 2

Spirantol can be obtained by collecting and purifying from the above-mentioned plants and can also be chemically synthesized. In the present invention, even spirantol obtained by the misalignment method can be used, and it is not necessary to have high purity. If the taste or odor of other ingredients does not affect the flavor of the food and drink, it may be used without refining the plant extract or essential oil containing spirantol. From the viewpoint of safety, it is preferable to use extracts or essential oils obtained from plants with dietary experience, and from the viewpoint of practicality such as supply, price, etc. Particular preference is given to using extracts of Dutch senchi or essential oils.

[0010] Spirantol is, for example, Dutch senchi or kibana having a high spirantol content. Dutch whole plant or flower head strength Can be collected by extraction or distillation. As an example of the extraction method by extraction, the flower heads of Dutch sennithi or kibana holland sennitchi are dried and ground and then extracted with an organic solvent to obtain an extract containing spiranthol. The organic solvent used for the extraction is not particularly limited. Alcohols such as methanol, ethanol, propanol and propylene glycol, ketones such as acetone, esters such as ethyl acetate, ethers such as jetyl ether, hexane and heptane And the like can be used alone or in combination as appropriate. Safety viewpoint power that polar organic solvents such as alcohols are preferable. Ethanol is particularly preferable. The solvent is removed from the obtained extract to obtain a spirantol-containing extract.

[0011] The obtained spirantol-containing extract can be used as it is as a taste improver of the high-intensity sweetener of the present invention, but the influence of ingredients other than spirantol contained in the extract on the flavor of food and drink In such a case, it is preferable to further increase the spirantol content by a purification method such as distillation. Examples of the purification method include molecular distillation, thin film distillation, various chromatography, and the like. By using these purification methods alone or in appropriate combination, the taste of a high-intensity sweetener with a higher spirantol content can be obtained. An improver can be obtained.

[0012] The taste-improving agent for high-intensity sweeteners according to the present invention can further enhance its effect by using spirantol together with quinic acid or a coffee bean hydrolyzate containing quinic acid. For quinic acid, a commercially available product or a natural product extract containing quinic acid may be used as it is. A coffee bean hydrolyzate containing quinic acid can be obtained by hydrolyzing green coffee beans with an alkali or an enzyme according to a method described in, for example, JP-A-2001-321115.

[0013] The taste improving agent of the present invention can be directly added to a high-intensity sweetener to obtain a high-intensity sweetener composition in which an unpleasant aftertaste peculiar to the high-intensity sweetener is improved. . In the case of a high-intensity sweetener composition, in addition to the high-intensity sweetener and the taste improver of the present invention, various sugars, organic acids, starches, dextrins, etc., commonly used dispersants, excipients, etc. Can be included as appropriate. Furthermore, by adding to foods and drinks containing high-intensity sweeteners, the unpleasant aftertaste caused by high-intensity sweeteners can be suppressed and the taste of food and drinks can be improved. The When the taste improver of the present invention is added to a high-intensity sweetener, the amount of added calories is 10 to LOOOOppm, preferably 100 to 1000 ppm as the spirantol content relative to the high-intensity sweetener. When added directly to foods and drinks containing high-intensity sweeteners, an appropriate amount of spices to be added is 0.01 to LOppm, preferably 0.1 to 1 ppm as the spirantol content in the final product. is there. When quinic acid or a coffee bean hydrolyzate containing quinic acid is used in combination, an addition amount of 0.005 to 10 ppm, preferably 0.1 to 2 ppm as the quinic acid content is appropriate. When used in combination, the ratio of spirantol and quinic acid can be used in any ratio that is not particularly limited.

In the present invention, a high-intensity sweetener is a sweetener having a sweetness that is several hundred times higher than that of sucrose. Stevia, licorice extract, thaumatin, glycyrrhizin, glycyrrhizin Examples thereof include disodium acid, ammonium glycyrrhizinate, saccharin, saccharin sodium, aspartame, acesulfame K, sucralose, aliteme, neotame, cyclamate (sodium or calcium cyclamate), and the like. The taste-improving agent of the present invention can be used without being limited by the type of high-intensity sweetener, especially for asparta me, stevia, sucralose, and acesulfam K. Is preferred.

[0015] The taste-improving agent for high-intensity sweeteners of the present invention can be added alone to foods and drinks containing high-intensity sweeteners, but can be arbitrarily combined with other flavoring ingredients to provide high-intensity sweetness. It can also be used as a flavor composition for food-containing foods and drinks. The perfume ingredients to be combined are not particularly limited, for example acetoacetyl acetate, acetophenone, anisaldehyde, α-amylcinnamaldehyde, methyl anthrallate, ionone, isoeugenol, isoamyl isovalerate, ethyl isovalerate, isothiocyanate , Isothiocyanic acid 3-butyl, isothiocyanic acid 4-pentyl, isothiocyanic acid benzyl, isothiocyanic acid 3-methylthiopropyl, isothiocyanates, indole and its derivatives, γ undecalactone, esters, ethylvaline, ethers Eugenol, octanol, otatanal, ethyl octoate, isoamyl formate, gerael formate, citronellyl formate, kain cinnamate, ketyl cinnamate, methyl cinnamate, ketones, ger-ol, isoamyl acetate, acetic acid Chill, acetate galley - le, cyclohexyl acetate cycloalkyl, citronellyl acetate, acetic acid Nannyl, terbyl acetate, phenethyl acetate, butyl acetate, benzyl acetate, 1-methyl acetate, linalyl acetate, methyl salicylate, aralkyl cyclohexylpropionate, citral, citronellal, citronellol, 1,8 cineole, fatty acids , Higher aliphatic alcohols, higher aliphatic aldehydes, higher aliphatic hydrocarbons, cinnamyl alcohol, cinnamaldehyde, thioethers, thiols, decanal, decanol, decanoyl decanoate, terpineol, limonene, pinene, Myrcene, tapinolen, terbene hydrocarbons, Ί-nonalatatone, phosphorus, paramethylacetophenone, hydroxycitronellal, hydroxycitronellal dimethylacetal, piperonal, isoamyl amylacetate, phe -Isobutyl acetate Phenyl acetate, phenol ethers, phenols, furfural and its derivatives, propionic acid, isoamyl propionate, ethyl propionate, benzyl propionate, hexanoic acid, allylic hexanoate, ethyl hexanoate, heptanoic acid Ethyl, 1-perylaldehyde, benzyl alcohol, benzaldehyde, aromatic alcohols, aromatic aldehydes, d-borneol, maltol, methyl N-methylanthranylate, methyl β-naphthyl ketone, dl-menthol, 1 menthol , Butyric acid, isoamyl butyrate, ethyl butyrate, cyclohexyl butyrate, butyl butyrate, ratatones, linac mouthol and other synthetic or natural flavors, oranges, lemons, limes, grapefruit citrus essential oils, apples, bananas , Grape, me Fruit-based essential oils or recovered flavors such as milk, cream, butter, cheese and yogurt, flavored flavors such as green tea, tea, coffee and cocoa, peppermint and spearmint Mint essential oil, Asanomi, Asafuetida, Ajowan, Ryo varnish, Angelica, Wikiwe, Tucon, Orega All spices, Orange nope, Power show, Katsushia, Chamomile, Mustard, Cardamom, Curry leaf, Kanzo, Caraway, Gardenia, cumin, taleson, clove, poppy flea, caper, pepper, sesame, coriander, sassafras, saffron, savory, salvia, salamander, perilla, cinnamon, charlotte, juverberry, ginger, sugi -Ryo varnish, spearmint, cicada rust, celery, solore, thyme, onion, tamarind, tarragon, chiayibu, dill, capsicum, nutmeg,-goatberry,-jeela, carrot, garlic, basil, parsley, heart force, vanilla, Paprika, Hyssop, Huene Greek, Spice extract obtained from peppermint, horsemint, horseradish, marjoram, miyouga, lavender, linden, lemongrass, lemon balm, rose, rosemary, laurel, coral rust, Iceland moss, aka jay, akebi, Asa, Asafuchida, Asian Tam, Ajowan, Azuki, Asno Lasasrine Alice, Upnore Mint, Artichoke, Anise, Avocado, Amachiya, Amatyazuru, Amiga Sayuri, Amiris, Armand, Aritasou, Arcanna, Artemisia, Al-Power, Alfalfa, Aloe, Angos La, Angola Weed, Apricot, Apricot, Angelica, Amber, Ambergris, Amblet, Squid, Squid, Idasa, East, Plover, Strawberry, Fig, A Yeo, Inokochi, Ylang Ylang, Iwaogi, Imperatria, Inmortel, Wintergreen, Watercress, Ukogi, Ukon, Uspasaisin, Woodruff, U-, Ume, Uronchiya, Egoma, Enokitake, Shrimp, Yebisugusa, Erigeron, Enoleda , Eleute Mouthcock, Ele Kampen, Eremi, Yengosaku, Yenju, Endive, European Thistle, Oren, Obako , Honoré spice, orange, aged range flower, chi, kaininsou, cacao, oysters, force rhinoceros, cashew nuts, cascara, cascarilla, castrium, katatari, cutlet bush, cutlet , Katsushi Fistula, force tech, force two, carnation, force nokosou, camomile, cape te, force rashi, karasuri, karasubishak, guarana, calamus, galanga, currant, carissa, karin, cardamom, galvanum, curry, casami , Licorice, Gambia, kanran, kiwi fruit, kikai gartake, kikiyou, chrysanthemum, jellyfish, scallop, swordfish, kitachi aloe, kina, kihada, kibanaougi, giboshi, gymnema norevesta, cat-top, caraway, kyalop, cucumber , Quilla, goldworm, guava, guayata, wolfberry, Japanese cedar, Japanese cedar, kuboboke, kuzu, tatsunoki, tasunohagashi, gooseberry, gardenia, kubeba, bearberry, gummy, cumin, ground ibi, clara, clarinese , Cranberry, tari, tarmi, cream, grainobu paradise, taleta di tanny, grape funolec, clover, clove, black moji, cucumber, crusher, caper, ghetto, cade, quebraco, germanand, kenchuyuru, kenponashi, geno shoko , Kouji, Kodake, Kochiya, Kohone, Coca, Koganenona, Kokuto, Konorei, Coconut, Goshu, Pepper, Kostas, Costmary, Ko Paipa, coffee, kobushi, burdock, sesame, cola, coriander, colts foot, gonored den rod, colombo, consai, conzu rango, comfrey, cypress, fish, cherry, sakura lamppo, pomegranate, salmon casserole, sasas, sasakusa, search, sasafras, saffron , Sapodilla, cactus, salamander, salsano lyra, salsifia, sarnoch moss, hawthorn, sanshu, sansho, santa herb, sandalac, sandalwood, sandallet, shiitake, diene, perilla, fern, citrus, citronella, sinus, civet , Simarouba, Shimeji, Peonies, Jasmine, Jianohige, Jaborangi, Shallot, Stasha, Juniper Berry, Ginger, Sho, Shochu, Jiyoushu, Sho Mouth, White bamboo, Ginseng, Cinnamon, Vinegar, Watermelon, Sisen, Sugi, Star anise, Star funole, Stylax, Sutubon, Subonbontake, Zdravets, Snake Norate, Spitanard, Spnolace, Spearmint, Sverhihu, Slow belly, Savory, Sekisho Sage, Zedary, Senega, Zeranium, Celery, Senukiyu, Centauria, Sengen, Sento Jonswold, Senna, Sauce, Daio, Soybean, Thyme, Bamboo Shoot, Octopus, Tade, Davana, Egg, Egg Bamboo, Onion, Tamarind , Damiana, Tamogitake, Tarragon, Taranoki, Tansy, Tangielin, Dandelion, Cherimola, Cherry Laurel, Cherry Wai Nored, Chigaya, Chicory, Cheese, Chichitake, Chiayibu Chiabinole, Champa power, tuberos, dung beetle, tilata, kushi, tsukemo ritta, camellia, camellia, crayfish carrot, tsudukudami, diatanda, tissuru, dittany, dill, dates, tendaijak, tenma, red pepper, dough, dough Shochubutsutsu, Doshoshotsuyu, Tomitsu, Corn, Dokudami, Tochu, Doggrass, Tomato, Dragon Blood, Dorian, Truffle, Truval Sam, Ton Force, Naginata Koju, Pear, Nastah Sham, Nuts, Natto, Natsu Nutmeg, Nadeshiko, Nameko, Narratake, -Auli, Niyusankinbayoeki, carrot, garlic, mouse mochi, nettle, nymphaea, knotgrass, violet, knap nore, nobiscus Malt, nokobe, nozinole, nose, lotus cup, nose cup, seri, nota, nootainore, noterminolek, noch, nochimitsu, noichiyuri, hatatsu force, knock bean, nokkoshu, nokko Yu, Nokkomieki, Nosyyon Fnore, Nottatake, No, / F: TP One-Bed, No-Tsugi, Nonasuge, Nonana, Noninira, Nonessa, / Kunore, Nonoya, No One-Berry, Nomagou, Nomasuge Hermanus, Nomadomafu, Nomadameris, Nora No Nore Marosa, Van Reishi, Hikoshishi, Hishi, Pistachio, Hyssop, Hickory, Peanuts, Hinoki, Hino, Pipsishi mushroom, Himehagi, hyacinth, oyster mushroom, birch, betel row, feijoa, fuenegrik, fennel, fujibakama, fujifudoki, fusuma fuzel Buchu, grapes, Budousakekasu, rose apple, beech, Bunaharitake, black Canon Laue I, blackberry, plum, Brio - §, Prickly ash, Primrose, Prunella, Funore ¹ ~ ~ Berri ¹ ~~ "" / Reddofunore ¹ to ~ Tsu Hey to the base I '~~ Senorenattsu exponentiation ¹ ~~ Baie' ~~ Tenore safflower, bi- Peniroiyanore, Bae Roh one mint to,, Bae Pino, peptone, Benoregamotto, base Norre gamut mint, Bae Norebanoresamu, Benore base Na, Veronica and Benzo Inn, Boad Rose, Hoa Hound, Ho, Bamboo Bamboo, Hou Sho, Bow Fu, Whey, Hoonoki, Horse Mint, Horseradish, Button, Hop, Poppy, Poplar, Popo, Jojoba, Hoya, Bonoredo, Boguchi, Maitake, Magnoreto, Marshmallow, Marjoram, Mastic, Masoy, Mata Tabi, Machiko, Pine, Matsuouji, Mashnolem, Matsutake, Matsubusa, Matsuhodo, Mate Chiya, Beans, Marigo Noredo, Manoleno Daio, Mango Mello, Mano Maro, Mano Citrus, Mishima Psycho, Miso, Mitsumata, Beeswax, Meat, Mimosa, Miyuga, Miruku, Mirte, Mirfu Oil, Myrrh, Mirobaran, Mugichiya, Musk, Murasaki, Mesquite, Meadow Sweet, Mejiki, Mape , Melissa, Merilot, Melon, Moosenoke, Moria Baiyoueki, Momokinoki, Momo, Morohaya, Kakuchi, Gillberry, Eucalyptus, Yukinoshita, Yuz, Yucca, Yuri, Yosai, Yoroda, Lions Foot, Lychee, Life Everlasting Flower, Lime, Lilac, Lacan Power, Lacanshaw, Raspberry, Rattan, Radish, Love Danum, Lavender, Langwald, Langmoth, Rambutan, Liqueur, Leak, Lituea, Linaroe, Longan, Liyo Funsou, Reyokucha, Apple, Linden, Lin Dough, roux, borage, reseda, lemon, lemongrass, forsythia, lotus, renbu, rosemary, mushrooms, lorenore, longoza, rust, shark toad, wormwood, worm sea , Warabi, are like the illustrated force resulting natural flavors like Waremokou, they are appropriately selected and used.

The taste improving agent of the present invention can be used without particular limitation for foods and beverages in which high-intensity sweeteners are used. Examples include beverages such as coffee, tea, sports drinks and milk beverages, confectionery such as candies, tablet confectionery and chewing gum, frozen desserts such as jelly and chilled desserts, and milk Products.

Example

[0017] The present invention will be specifically described below with reference to examples, but the present invention is not limited to the description of the examples.

[0018] [Production Example 1] (Crude Spirantol 1)

100 kg of 99% ethanol was extracted for 5 hours at 75 ° C to reflux temperature. The extract was cooled to 40 ° C and then solid-liquid separated by a centrifuge, and the extract was concentrated to 20 kg under reduced pressure. After adding 0.2 kg of activated carbon to the concentrate and stirring for 1 hour, diatomaceous earth was added and filtered under pressure to remove the activated carbon, followed by concentration under reduced pressure to obtain 0.43 kg of Dutch Senchi concentrate. Distilled water (2 kg) was added to the concentrate, and the mixture was extracted 3 times with 2 kg of ethyl acetate. The extracted ethyl acetate layers were combined, diatomaceous earth was added, and the mixture was filtered under pressure, and concentrated under reduced pressure to obtain 0.3 lkg of a crude Dutch Senchi extract. Yield 3.1%. Spiranthol content 12.4%.

The above Dutch Sennici crude extract lOOg is mixed with fatty acid triglyceride lOOg, and distilled using a vacuum thin film distillation apparatus at a vacuum of 3 to 5 Pa and an evaporation surface temperature of 110 to 150 ° C., and the distillate (crude spirantol). 1) 33.3 g was obtained. Yield 33%. Spirantol content: 38.0% by weight. The crude spilanthol 1 0. lg diluted with 50 weight ^_0/0 aqueous ethanol 760 g, after cooling to 5 ° C, rows Ka卩E filtration kieselguhr, crude Spira Ntoru solution of spilanthol concentration 50 ppm (w / w) 1 was prepared.

[Production Example 2] (Crude Spirantol 2)

Netherlandssen-chi crude extract of production example 1 (spirantol content: 12.4%) 50 g of fatty acid triglyceride is mixed with lOOg, and using a vacuum thin film distillation apparatus, vacuum degree: 4-5 Pa, evaporation surface temperature: 120 ° Distillation with C gave 12.3 g of distillate (crude spirantol 2). Yield 12.3%. Spilanthol content: 67.3 mass ^_0/0.

The crude spilanthol 2 0. lg diluted with 50 weight ^_0/0 aqueous ethanol 1346G, after cooling at 5 ° C until the crude spiran torr solution 2 spilanthol concentration 50ppm performed diatomaceous earth was added filtration (w / w) Prepared.

[0020] [Production Example 3] (Purified Spirantol) Dutchsen-chi dried flower head (300 g) was refluxed and extracted with 3200 g of 95% ethanol by volume for 1 hour. The extract was cooled and solid-liquid separated, and diatomaceous earth was added and filtered. The filtrate was concentrated under reduced pressure to remove ethanol, 300 g of water was added, and the mixture was extracted 3 times with 300 ml of hexane. The extracted hexane layers were combined and concentrated under reduced pressure to distill off the hexane to obtain 8.4 g of a crude extract. Yield 2.8% (spirantol content 9.5%).

The crude extract 8.4 g was fractionated by silica gel column chromatography (silica gel 200 g, Φ5 «η) (eluted with n-hexane: ethyl acetate = 8: 2), and the spirantol fraction (Rf value = 0. 2 to 0.3 n-hexane: ethyl acetate = 7: 3) was collected, and the solvent was distilled off under reduced pressure to obtain 2.76 g of crude spirantol fraction 1. Subsequently, the crude spirantol fraction 1 was purified by simple distillation (180 ° C.) using a Kugelrohr distillation apparatus under reduced pressure (0. ImmHg) to obtain 0.98 g of crude spirantol fraction 2. Yield 0.33% (spirantol content 41.9%). Further, 0.98 g of the crude spirantol fraction 2 was fractionated by silica gel column chromatography (silica gel 200 g, Φ 5 cm) (elution with n-hexane: ethyl acetate = 95: 5-90: 10), The spirantol fraction (Rf value = 0.2: n-hexane: ethyl acetate = 7: 3) was collected, and the solvent was distilled off under reduced pressure to obtain 0.4 g of purified spirantol. Yield 0.13%. Spilanthol content 98 mass ^_0/0. The structure of spirantol was confirmed by measuring proton and carbon 13N MR and comparing with known literature data.

The purified spilanthol 0. 104 g was diluted with 50 weight ^_0/0 ethanol 2000 g, to prepare a purified spilanthol solution of scan Pirantoru concentration 50ppm (w / w).

[0021] Chlorogenic acid esterase hydrolyzate of green coffee beans prepared by the method described in JP-A-2001-321115 in addition to the crude spirantol solutions 1 and 2 obtained in Production Examples 1 to 3 and the purified spirantol solution The taste-improving effect on high-intensity sweeteners was examined using a sweet taste improving agent consisting of (a quinic acid content of 32%, hereinafter referred to as “raw green coffee hydrolyzate”). In the following test examples, the scoring criteria for sensory evaluation were those listed in Table 1.

[0022] [Table 1] Lightness ・ Rear cut Bitterness “Egu taste Citrus or Spa feeling Very desirable 7 points Very strong 7 points Very strong 7 points Desired 6 points Strong 6 points Strong 6 points Slightly desirable 5 points Slightly strong 5 points Slightly Strong 5 points Equivalent to control 4 points Equivalent to control 4 points Equivalent to control 4 points Slightly bad 3 points Slightly weak 3 points Slightly weak 3 points Sub- \ 2 points Weak 2 points Weak and 2 points Very bad 1 point Very good Weak 1 point Very weak 1 point

[0023] [Test Example 1] Effect on aspartame

Crude spirantol solution 1, crude spirantol solution 2, and purified spirrantol solution were added to the aspartame aqueous solution of Formula 1 so that the spirantol content in the aspartame aqueous solution was 0.5 ppm. In addition, green coffee bean hydrolyzate was added so that the quinic acid content in the aspartame aqueous solution was 1 ppm. Further, the crude sprantol solution 2 was added together so that the spirantol content in the aspartame aqueous solution was 0.2 ppm and the green coffee bean hydrolyzate was 0.3 ppm in the quinic acid content. These aspartame aqueous solutions were subjected to sensory evaluations using 10 panelists who were trained using the additive-free product as a control (comparative example), and the results are shown in Table 2. The score in Table 2 is the average score of each panel scored according to the scoring standards in Table 1 (1 to 7 points).

[0024] (Prescription 1)

Lolo name

Aspartame 0.6

Quenic acid 1.0

Water residue

A doo 1000. 0 pH: 2.7

Sterilization conditions: 70 ° CX for 10 minutes [0025] [Table 2] Evaluation sample

No additive (comparative example) 4.0

Crude spirantol 1 5. 1

Crude spirantol 2 5. 3

Purified Spirantol 5.4

Coffee green bean hydrolyzate 5.0

Crude spirantol 2 +

6. 0

Coffee raw bean hydrolyzate

As apparent from Table 2, the unpleasant aftertaste peculiar to aspartame was improved by adding spirantol to the aspartame aqueous solution. Spirantol showed the same or better taste-improving effect than the green coffee bean hydrolyzate, and the effect was further enhanced when spirrantol and coffee green bean hydrolyzate were used in combination.

[0027] [Test Example 2] Effect on sucralose

Crude spirantol solution 2 was added to the sucralose aqueous solution of formulation 2 so that the spirrantol content in the beverage was 0.2 ppm. In addition, crude spirantol solution 2 was added in combination so that the spirantol content in the sucralose aqueous solution was 0.05 ppm, and the green coffee bean hydrolyzate had a quinic acid content of 0.1 ppm. These three sucralose aqueous solutions were subjected to sensory evaluations using a panel of 10 persons who were trained using the additive-free product as a control (comparative example). The results are shown in Table 3. The score in Table 3 is the average score (1-7 points) based on the criteria in Table 1.

[0028] (Prescription 2)

Product name Blending amount (g)

Sucralose 0.2

Quenic acid 0.5

Water residue

Total 1000.0 pH: 2.6

Sterilization conditions: 70 ° CX for 10 minutes [0029] [Table 3]

[0030] As is apparent from Table 3, by adding spirantol to the sucralose aqueous solution, the bitterness / eda taste peculiar to sucralose was reduced, and unpleasant sweetness sustained as an aftertaste was suppressed. In addition, the combined effect of spirantol and green coffee bean hydrolyzate has an additional effect of seven.

[0031] [Test Example 3] Effect on acesulfame K

Crude sprantol solution 2 was added to the acesulfame K aqueous solution of Formula 3 so that the spirantol content in the acesulfame K aqueous solution was 0.2 ppm. The crude spirrantol solution 2 was added together so that the spirantol content in the acesulfame K aqueous solution was 0.1 ppm, and the coffee raw bean hydrolyzate had a quinic acid content of 0.1 ppm. These acesulfame K aqueous solutions were subjected to sensory evaluations using a panel of 10 people who were trained using the non-supplemented product as a control (comparative example). The results are shown in Table 4. The score in Table 4 is the average score (1-7 points) based on the criteria in Table 1.

[0032] (Prescription 3)

Lolo name

Acesulfame K 0. 4

Quenic acid 0. 05

Water residue

A doo 1000. 0 pH: 2. 9

Sterilization conditions: 70 ° CX for 10 minutes [0033] [Table 4] Evaluation sample

No additive (comparative example) 4.0 0 4.0

Coarse spiran! 2 5. 7 1.6

Coarse spiran! Le 2 +

6. 0 1. 6

Coffee bean hydrolyzate

[0034] As is apparent from Table 4, the addition of spirantanol to the aqueous solution of acesulfame K reduced the bitterness and eda taste peculiar to acesulfame K and suppressed the unpleasant sweetness that persisted as the aftertaste.

The effect was further enhanced when spirantol was used in combination with green coffee bean hydrolyzate.

[0035] [Example 1] Functional beverage containing aspartame

Crude spirantol solution 1, crude spirantol solution 2, and purified spirantol solution were added to the functional beverage of Formula 4 so that the spirantol content in the beverage was 0.2 ppm, respectively. Further, the green coffee bean hydrolyzate was added so that the quinic acid content in the beverage was 0.2 ppm. Further, the crude spirrantol solution 2 was added together so that the spirrantol content in the beverage was 0.05 ppm and the green coffee bean hydrolyzate was 0.1 ppm in the beverage. These solutions were subjected to sensory evaluations using a panel of 10 trained experts who used non-additive strength as a control (comparative example). The results are shown in Table 5. The evaluation score in Table 5 is the average score (1-7 points) based on the criteria in Table 1.

[0036] (Prescription 4)

Lolo name Compounding amount (g)

Aspartame 0.240

Chenic acid 2.000

Sodium quenate 0. 800

Anoleginine 0. 300

Kelp extract 0. 180

Sodium chloride 0.150

Calcium lactate 0. 100 vitamin. 0. 050

Niacin 0. 010

Calcium pantetonate 0.005

Vitamin B6 0. 002

Grapefruit flavored fragrance (Ogawa Fragrance Co., Ltd.)

Water residue

Total 1000. 000

Brix: 0.35

pH: 3.4

Sterilization conditions: 70 ° C x 10 minutes

[0037] [Table 5]

[0038] As is apparent from Table 5, the addition of spirantol to a functional beverage containing aspartame enhanced the citrus feel of the beverage and improved the lightness and afterbreak. In addition, spirantol showed the same or better taste-improving effect on green coffee bean hydrolyzate, and the effect was further enhanced when spirantol and coffee green bean hydrolyzate were used in combination.

[Example 2] Functional drink containing sucralose

Crude spirantol solution 3 was added to the functional beverage of Formula 5 so that the spirantol content in the beverage was 0.2 ppm. In addition, the crude spirantol solution 2 has a spirantol content of 0.1 ppm in the beverage, and the coffee bean hydrolyzate is quinic acid in the beverage. The combined addition was carried out so that the content was 0.1 ppm. These solutions were subjected to sensory evaluations using a panel of 10 trained experts using the additive-free product as a control (comparative example). The results are shown in Table 6. The evaluation score in Table 6 is the average score (1-7 points) based on the following criteria.

(Prescription 5)

Lolo name Compounding amount ( _g )

Sucralose 0. 080

Chenic acid 2.000

Sodium quenate 0. 800

Anoleginine 0. 300

Kelp extract 0. 180

Sodium chloride 0.150

Calcium lactate 0. 100

Vitamin C 0. 050

Niacin 0. 010

Calcium pantetonate 0.005

Vitamin B6 0. 002

Grapefruit flavored fragrance (made by Ogawa Fragrance Co.) 0. 015

water

A

σ DOO P I 1000. 000

Brix: 0.33

pH: 3.4

Sterilization conditions: 70 ° CX for 10 minutes [Table 6] Evaluation sample Cirrus feeling Lightness

No additive (comparative example) 4.0 0 4.0

Coarse spirant 2 4. 9 5. 3

Coarse spirant 2 +

4. 9 5. 6

Coffee bean hydrolyzate

[0042] As is apparent from Table 6, the addition of spirantol to a functional beverage containing sucralose enhanced the citrus feel of the beverage and improved its lightness and afterbreak. In addition, the effect of spirantol and coffee green beans hydrolyzate was further enhanced.

[0043] [Example 3] Carbonated beverage containing aspartame

To the carbonated beverage of formula 6, the crude spirantol solution 2 was added so that the spirantol content in the beverage was 0.5 ppm. In addition, the crude spirantol solution 2 was added in combination so that the spyrantol content in the beverage was 0.2 ppm, and the green coffee bean hydrolyzate was 0.3 ppm in the beverage. These solutions were subjected to sensory evaluations using a panel of 10 people who were familiar with the use of non-restrained products as control consoles (comparative examples). Table 7 shows the results. The score in Table 7 is the average score (1-7 points) based on the criteria in Table 1.

[0044] (Prescription 6)

Product name Blending amount (g)

Diacid 1.00

Aspartame 0.45

Chenic acid 0.60

Caffeine 0. 10

Caramenole 2. 70

Cola flavored fragrance (Ogawa Fragrance Co., Ltd.) 1. 00

Carbonated water 850. 00

Water residue

Total 1000.00 Brix: 0.5

pH: 2.8

Sterilization conditions: not sterilized

[0045] [Table 7]

[0046] As is apparent from Table 7, the addition of spirantol to the aspartame-containing carbonated beverage enhanced the citrus and spice sensation of the beverage and improved its lightness. Moreover, the effect was further enhanced by the combined use of spyrantol and green coffee bean hydrolyzate.

[0047] [Example 4] Acesulfame K composition

10 g of crude spirantol 2, 20 g of modified starch, and 70 g of dextrin were added to 150 g of water for emulsification, and this was spray-dried to obtain spirantol powder. 0.5 g of this powder was added to acesulfame KlOOg and mixed uniformly to obtain acesulfame K mixed powder. When this acesulfame K mixed powder is added to foods and drinks, the bitterness and eda taste peculiar to acesulfame K is reduced, and unpleasant sweetness that persists as an aftertaste is suppressed, compared to those without the taste improver of the present invention. did.

[0048] [Example 5] Aspartame composition

Spirrantol powder obtained in Example 4 1. Og was added to 100 g of aspartame and mixed uniformly to obtain an aspartame mixed powder. Water was added to 10 g of this ammonium nitrate mixed powder to make a total amount of 100 g, and the mixture was uniformly heated and dissolved. To this solution, 10 g of ethanol was added to obtain an aspartame mixed aqueous solution. When this aspartame mixed aqueous solution was added to foods and drinks, unpleasant sweetness sustained as an aspartame-specific aftertaste was suppressed as compared to the product without the addition of a sweet taste improving agent.

Industrial applicability The taste improver of the present invention is added to a food or drink containing a high sweetness degree sweetener, or the high sweetness sweetener composition containing the taste improver of the present invention is added to a food or drink. As a result, the unpleasant sweetness, bitterness, and eda taste remaining as a aftertaste, which are characteristic of high-intensity sweeteners, can be reduced. Since the taste improving agent of the present invention is effective when added in a small amount, it can improve the unpleasant aftertaste of a high-intensity sweetener without affecting the taste of food and drink.

Claims

The scope of the claims

[1] A taste-improving agent for high-intensity sweeteners, characterized by comprising spirantol or a plant extract or essential oil containing spirantol.

[2] The taste-improving agent for high-intensity sweeteners according to claim 1, wherein the plant containing spirrantol is Dutchsenchi or Kibana Dutchsenchi.

[3] The taste-improving agent for high-intensity sweeteners according to claim 1 or 2, wherein the high-intensity sweetener is aspartame, sucralose, or acesulfame K.

[4] The taste-improving agent for high-intensity sweeteners according to any one of claims 1 to 3, further comprising quinic acid or a coffee bean hydrolyzate containing quinic acid as an active ingredient. .

[5] Adding a taste improver for high-intensity sweeteners according to any one of claims 1 to 4 to a high-intensity sweetener or a food or drink containing high-intensity sweeteners. A method for suppressing an unpleasant aftertaste, characterized by a high-sweetness sweetener.

[6] A flavor composition for foods and beverages containing a high-intensity sweetener, comprising the taste-improving agent for a high-intensity sweetener according to any one of claims 1 to 4.

[7] An unpleasant sensation caused by a high-intensity sweetener, comprising a high-intensity sweetener and a taste improver for high-intensity sweetener according to any one of claims 1 to 4. A high-intensity sweetener composition having a suppressed aftertaste.

[8] An unpleasant sensation caused by a high-intensity sweetener, comprising a high-intensity sweetener and a taste improver of the high-intensity sweetener according to any one of claims 1 to 4. A loro with a reduced aftertaste.