US 2008.005 0500A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2008/0050500 A1 Muranishi et al. (43) Pub. Date: Feb. 28, 2008

(54) ADDITIVE FOR CARBONATED BEVERAGE Publication Classification (51) Int. Cl. (75) Inventors: Shuichi Muranishi, Okayama (JP): A2.3L 2/56 (2006.01) Kazuyuki Miyake, Saitama (JP); A2.3L. I./22 (2006.01) Takashi Uesugi, Chiba (JP); Yuka A2.3L 2/38 (2006.01) Mori, Chiba (JP); Toshio Miyazawa, (52) U.S. Cl...... 426/590: 426/651 Chiba (JP) (57) ABSTRACT It is intended to provide a carbonated beverage excelling in Correspondence Address: function as thirst-quenching beverage and taste through OBLON, SPIVAK, MCCLELLAND MAIER & strengthening or Sustaining of carbonated feel peculiar to NEUSTADT, P.C. carbonated beverage (brisk intense stimulation and sensa 194O DUKE STREET tion at pass through the throat, brought about by carbon ALEXANDRIA, VA 22314 (US) dioxide gas, and sensation of coolness (refreshing sensation) produced by a combination of carbon dioxide gas and flavor) (73) Assignee: OGAWA & Co., LTD., Chuo-ku, Tokyo which after opening, rapidly drops depending upon a com (JP) bination of employed raw materials, such as fruit juice, Sweetener, color additives and flavoring, and upon evapo (21) Appl. No.: 11/722,132 ration of carbon dioxide gas. The drop of carbonated feel brought about depending upon a combination of raw mate (22) PCT Filed: Dec. 19, 2005 rials, such as fruit juice and Sweetener, can be relieved by adding to a carbonated beverage an additive for carbonated (86). PCT No.: PCT/UP05/23221 beverage comprising spilanthol or a spilanthol-containing S 371(c)(1), extract or plant essential oil as an active ingredient. (2), (4) Date: Jun. 19, 2007 Further, the addition would help inhibit drop of carbonated feel brought about depending upon evaporation of carbon (30) Foreign Application Priority Data dioxide gas after opening and would help retain the taste and function as function as thirst-quenching beverage inherently Dec. 20, 2004 (JP)...... 2004-367385 to be had by carbonated beverage even after opening. US 2008/005 0500 A1 Feb. 28, 2008

ADDITIVE FOR CARBONATED BEVERAGE Means for Solving the Problems TECHNICAL FIELD 0007 As a result of research on materials that enhance the carbonated feel of carbonated beverages with the aim of 0001. The present invention relates to an additive for solving the problems described above, the present inventors carbonated beverages that comprises as the active ingredient have completed this invention upon discovering that addi spilanthol or a spilanthol-containing plant extract or plant tion of a small amount of spilanthol enhances the desirable essential oil, to carbonated beverages and flavorings for stimulation of carbonation produced by carbon dioxide gas, carbonated beverages that contain the aforementioned addi thereby enhancing and maintaining the carbonated feel of tive, and to a method of enhancing or maintaining the beverages. carbonated feel of carbonated beverages by addition of the additive. 0008 Specifically, the present invention provides an additive for carbonated beverages that comprises as the BACKGROUND ART active ingredient spilanthol or a spilanthol-containing plant extract or plant essential oil, as well as an additive for 0002 Carbonated beverages such as soda pops and colas carbonated beverages wherein the spilanthol-containing add pleasure to daily life and have long been popular types plant is Spillanthes acmella or Spilanthes acmella var. Olera of Soft drinks among children and adults. They are particu CaC larly enjoyed as thirst quenching beverages in hot Summer periods or when perspiring after exercise. Carbonated bev 0009. The invention further provides a flavoring compo erages have a characteristic "carbonated feel” (an intense, sition for carbonated beverages characterized by containing refreshing stimulation on the throat produced by carbon the aforementioned additive for carbonated beverages. The dioxide gas, or a cool (refreshing) feel created by the invention still further provides carbonated beverages char combination of carbon dioxide gas and flavor) not shared by acterized by containing the aforementioned additive for other types of soft drinks, which contributes to its effect of carbonated beverages or flavoring composition for carbon quenching thirst. However, carbonated beverages may not ated beverages, wherein the carbonated beverages contain exhibit a satisfactory carbonated feel when prepared in spilanthol at 1-300 ppb. The carbonated beverages are also combination with added substances Such as juices, Sweet characterized by having -based flavors. eners, color additives, flavorings and the like. Furthermore, 0010. The invention still further provides a method for when rapid escape of carbon dioxide gas occurs after cap enhancing or maintaining the carbonated feel of a carbon opening, resulting in “flatness', the carbonated beverage ated beverage, by addition of the aforementioned additive loses the essential intense, refreshing stimulation of the for carbonated beverages or flavoring composition for car carbon dioxide gas, thereby reducing the carbonated feel and bonated beverages to a spilanthol content of 1-300 ppb in the quickly lowering the palatability after the cap has been carbonated beverage. opened. 0003 Carbonated beverages hitherto proposed include EFFECT OF THE INVENTION carbonated beverages containing specific proportions of 0011 Addition of the additive for carbonated beverages high-Sweetness Sweeteners in formulations containing rela of the invention to a carbonated beverage prevents loss of tively large amounts of carbon dioxide gas and plant com the carbonated feel that occurs by combination with mate ponents such as fruit juices, to provide a soothing, refreshing rials such as fruit juices, sweeteners and the like. Moreover, feel along with both the rich taste of the plant components loss of the carbonated feel due to escape of carbon dioxide and the stimulation of carbon dioxide gas (Patent document gas after cap opening is minimized, and the intended func 1), and carbonated beverages with enhanced quality of taste tion and palatability as a thirst-quenching beverage is main including stimulation, creamy texture and rich taste, pro tained even after opening of the cap. duced with addition of DE9-20 amylolysis product to the carbonated beverages (Patent document 2). However, no BEST MODE FOR CARRYING OUT THE methods are yet known for enhancing the carbonated feel, INVENTION including the stimulating and refreshing feel of carbon dioxide gas, which is reduced due to the effects of other 0012. The spilanthol used for the invention is N-isobutyl materials in the beverage and escape of gas after cap 2.6,8-decatrieneamide, represented by the chemical formula opening. shown below, which is a pungent component found in Spilanthes acmella, Spilanthes acmella var. Oleracea, and 0004 Patent document 1 WO 2002/067702 other varieties. 0005 Patent document 2.JP 2002-330735. A CHCH=CH CH-CH(CH),CH=CHCONHCH-CH(CH), DISCLOSURE OF INVENTION 0013 Spilanthol can be obtained by extraction and puri fication from these , or it may be chemically synthe Problems to be Solved by the Invention sized. Spilanthol obtained by any such methods may be used 0006. It is an object of the present invention to solve the for the invention, and it does not need to be a highly purified problems of reduced carbonated feel resulting from combi form. Spilanthol-containing plant extracts or essential oils nation with added materials such as fruit juices, Sweeteners, may be used without purification so long as their tastes and color additives and flavorings, of reduced carbonated feel odors do not adversely affect the flavor of the carbonated caused by rapid escape of carbon dioxide gas after cap beverage. From the viewpoint of safety it is preferred to use opening, and of accelerated loss of function or palatability as extracts or essential oils obtained from proven edible plants, a thirst-quenching beverage after opening of the cap. while from the viewpoint of supply, cost and other practical US 2008/005 0500 A1 Feb. 28, 2008 factors, it is particularly preferred to use extracts or essential furfural and its derivatives, propionic acid, isoamyl propi oils of Spillanthes acmella or Spillanthes acmella var. Olera onate, ethyl propionate, benzyl propionate, hexanoic acid, cea, which have high spilanthol contents. allyl hexanoate, ethylhexanoate, ethylheptanoate, 1-peril 0014. The spilanthol may be obtained by extraction or laldehyde, benzyl alcohol, benzaldehyde, aromatic alcohols, distillation from the total or head of Spilanthes aromatic aldehydes, d-borneol, maltol, methyl N-methylan acmella or Spillanthes acmella var. Oleracea, which have thranilate, methyl 3-naphthylketone, d1-menthol, 1-men high spilanthol contents. Using extraction for the sake of thol, butyric acid, isoamyl butyrate, ethylbutyrate, cyclo illustration, flower heads of Spilanthes acmella or Spilanthes hexylbutyrate, butylbutyrate, lactones, linalool and the like: acmella var. Oleracea are dried and crushed and then Sub Essential oils of citrus fruits such as orange, lemon, lime and jected to extraction with an organic solvent to obtain a grapefruit, essential oils or recovered flavors of fruits such spilanthol-containing extract. The organic solvent used for as apple, banana, grape, melon, peach, pineapple and Straw extraction is not particularly restricted, and may be an berry, extract flavors of dairy products such as Such as milk, alcohol Such as methanol, ethanol, propanol or propylene cream, butter, cheese and yogurt, recovered flavors of pal glycol, a ketone Such as acetone, an ester Such as ethyl atable products such as green tea, black tea, coffee and acetate, an ether Such as diethyl ether or a hydrocarbon Such cocoa, or essential oils of mints such as and as hexane or heptane, either alone or in admixture as , as well as extracts obtained from appropriate. A polar organic solvent Such as an alcohol is seed, , ajowan, , angelica, , , preferred, with ethanol being particularly preferred from the , , orange peel, SZechuan pepper, cassia, standpoint of safety. The solvent is distilled off from the chamomile, , , or curry obtained extract solution to obtain the spilanthol-containing tree, , , Zhi pear, , water cress, eXtract. , , caper, pepper, , , Sassa fras, , savory, Salvia, , beefsteak plant, 0.015 The spilanthol-containing extract may be used , shallot, , , star anise, spear directly as an additive for carbonated beverages according to mint, , , , , onion, , the invention, but in cases where components other than the , chive, , pepper, , wormwood, nigella, spilanthol in the extract may adversely affect the taste of the ginseng, , , , peppermint, , Chinese carbonated beverage, it is preferred to increase the spilanthol chive, bell pepper, hyssop, , peppermint, horse content by a purification method such as distillation. mint, horseradish, , , lavender, linden, lem 0016. The purification method may be molecular distil ongrass, , rose, , bay, horseradish and lation, thin-film distillation or a chromatography method, the like, or natural obtained from Iceland moss, and Such purification methods may be used alone or in rehman di huang, akebia, cannabis, asafoetida, maidenhair appropriate combinations to obtain an additive for carbon fern, ajowan, azuki bean, rooibos, applemint, artichoke, ated beverages with a higher spilanthol content. anise, , hydrangea, jiaogulan, fritilla lily, amyris, Sweet , almond, epazote, alkanet, artemisia, arnica, 0017. The additive for carbonated beverages of the inven alfalfa, aloe, angostura, angola weed, apricot, chanterelle, tion may be added alone to a carbonated beverage, but it may angelica, amber, ambergris, ambrette, Squid, barrenwort, also be combined with any other desired flavoring compo rush, yeast, Japanese knotweed, strawberry, fig, ginkgo, nents for use in a flavoring composition for carbonated Oxknee, ylangylang, hedysa huang qi, imperatoria, immor beverages. Flavoring components to be used in combination telle, wintergreen, watercress, ivy, turmeric, uSubasai wild therewith are not particularly restricted, and as suitable ginger, Woodruff, sea urchin, ume, oolong tea, peril Sesame, examples there may be mentioned synthetic and natural enokitake, shrimp, ebisugusa, erigeron, elder, eleutherococ derived flavorings such as ethyl acetoacetate, acetophenone, cus, elecampane, elemi, engosaku, huaijiao, endive, blessed anisaldehyde, C.-amylcinnamaldehyde, methyl anthranilate, thistle, huang lian, plantain, cnidium fruit, krill, , oak ionone, isoeugenol, isoamyl isovalerate, ethyl isovalerate, moss, cricket, osmanthus, opoponax, ominaeshi, water allyl isothiocyanate, 3-butenyl isothiocyanate, 4-pentenyl plantain, origanum, orris, olibanum, olive, allspice, orange, isothiocyanate, benzyl isothiocyanate, 3-methylthiopropyl orangeflower, seaweed, kaininso, cacao, persimmon, fruit isothiocyanate, other isothiocyanates, indole and its deriva vegetables, cashew nut, cascara, cascarilla, castoreum, tives, Y-undecalactone, esters, ethylvanillin, ethers, eugenol, kataku chestnut, dried skipjack, cassie, purging cassia, cat octanol, octanal, ethyl octanoate, isoamyl formate, geranyl echu, crab, carnation, Valerian, chamomile, cajeput, mus formate, citronellyl formate, cinnamic acid, ethyl cinnamate, tard, karasuuri, crowdipper, guarana, calamus, galanga, cur methyl cinnamate, ketones, geraniol, isoamyl acetate, ethyl rant, carissa, Chinese quince, cardamom, galbanum, curry, acetate, geranyl acetate, cyclohexyl acetate, citronellyl kawamidori, liquorice, gambir, Chinese olive, kiwifruit, acetate, cinnamyl acetate, terpinyl acetate, phenethyl kikaiga seaweed, take, baloonflower, juhua, Jews ear, kisas acetate, butyl acetate, benzyl acetate, 1-menthyl acetate, grasse, gishigishi, kidachi, aloe, Peruvian bark, linallyl acetate, methyl salicylate, cyclohexylallyl propi kihada, kibanao huang qi, giboshi, gymnema Sylvestre, onate, citral, citronellal, citronellol, 1,8-cineol, fatty acids, catnip, caraway, carob, cucumber, quillaia, agrimony, guava, aliphatic higher alcohols, aliphatic higher aldehydes, ali guaiacum, gou qi Zi, kusasugik cedarura, Japanese quince, phatic higher hydrocarbons, cinnamyl alcohol, cinnamalde kudzu, camphor, kamala, gooseberry, Zhi pear, cubeb, bear hyde, thioethers, thiols, decanal, decanol, ethyl decanoate, berry, peach, oleaster, cumin, ground ivy, kurara, clary sage, terpineol, limonene, pinene, myrcene, terpinolene, terpene cranberry, chestnut, walnut, cream, grains of paradise, dit based hydrocarbons, Y-nomalactone, Vanillin, paramethylac tany of crete, water-pepper, dittany, grapefruit, clover, clove, etophenone, hydroxycitronellal, hydroxycitronellaldimethy kuromoji, mulberry, quassia, caper, getto, cade, quebracho, lacetal, piperonal, isoamyl phenylacetate, isobutyl germander, kencur, Japanese rais pear, gennoshoko, koji, phenylacetate, ethyl phenylacetate, phenol ethers, phenols, koutake, black tea, kohone, coca, skullcap, brown Sugar, US 2008/005 0500 A1 Feb. 28, 2008 cereals, coco nut, Wu Zhu yu, pepper, costus, costmary, podocarp, raspberry, rhatany, radish, labdanum, lavender, copaiba, coffee, kobushi, burdock, Sesame, cola, coriander, lungwort, lungmoss, ramboutan, liqueur, leek, litsea, linaloe, coltsfoot, golden rod, calumba, root vegetable, condurango, longan, ryofunso, green tea, apple, linden, gentian, rue, comfrey, cypress, fish, cherry flower, cherry, , , reseda, lemon, lemongrass, lian qiao, lotus, wax sake cake, bamboo grass, Sasakusa, sea buckthorn, , jambu, rosemary, , bay, longose, horseradish, saffron, sapodilla, cactus, Sarashina pearoma, Sarsaparilla, watafujiutsugi, wormwood, wormseed, bracken, burnet and Salsify, polypore, hawthorn, shan Zhu yu, Sichuan pepper, the like. Santa herb, sandarac, Sandalwood, red sandalwood, Shiitake, genet, beefsteak plant, cedar, citrus, citronella, Schinus, 0018 When an additive for carbonated beverages or a civet, Simaro rulea, shimeji, Chinese peony, jasmin, Mondo flavoring composition containing an additive for carbonated grass, jaborandi, shallot, shukusha, juniper berry, ginger, beverages according to the invention is added to a carbon Soy, soy sauce cake, spirits, shoro, elm mushroom, tamogi ated beverage, it prevents loss of the carbonated feel that take, ginseng, cinnamon, Vinegar, watermelon, Squid, nar occurs by mixture with materials such as fruit juices, Sweet cissus, cedar, star anise, starfruit, styrax, terrapin, Suppon eners and the like, while also preventing a reduced carbon take, Zdravetz, Snakeroot, spikenard, spruce, spearmint, ated feel due to escape of carbon dioxide gas after opening purslane, sloe berry, savory, grassy-leaved Sweet flag, sage, of the cap. Zedoary, Senega, geranium, celery, Senkyu, centaury, sendan, 0019. There are no particular restrictions on the amount St. John’s wort, Senna, Sauce, rhubarb, soybean, thyme, added to a carbonated beverage, but generally the spilanthol bamboo shoot, octopus, water-pepper, davana, egg, royal content in the final carbonated beverage product is preferred agaric, onion, tamarind, damiana, tamogitake, tarragon, to be 1-300 ppb, more preferably 5-150 ppb and even more angelica tree, tansy, tangerine, dandelion, cherimoya, cherry preferably 15-100 ppb. A spilanthol content of less than 1 la bay, wild cherry, Cogon Grass, chicory, cheese, chichi ppb may not produce a sufficient effect, while a spilanthol take, chive, , champaca, tuber rose, Wuwei Zi, chirata, content of greater than 300 ppb will tend to bring out the fern-ally, pickled products, ivy, camellia, tsuyukusa, tsurig pungency of the spilanthol. Spilanthol is used in oral com aneni ginseng, tsurudoku chameleon, deertongue, thistle, positions such as dental pastes to enhance the refreshing feel dittany, dill, date, lindera root, tenma, pepper, toki, proteins, of menthol and the like (JPS48-43870 B), but the amount of oils and fats, molasses, cornsilk, chameleon, eucommia, dog spilanthol added is 1 ppm or greater in Such oral composi grass, tomato, dragon's blood, dorian, truffle, tolu ruelsum, tions; in contrast, the additive for carbonated beverages of tonka, naginata koju, pear, nasturtium, nut, fermented Soy the invention provides a maintaining and enhancing effect bean, Chinese dates, nutmeg, pink, nameko, naratake, ti on the carbonated feel even with an addition amount of tree, cultured lactic acid bacteria Solution, ginseng, garlic, below 1 ppm. neZumimochi, nettle, silk tree, knotgrass, violet, pineapple, hibiscus, malt, chickweed, basil, lotus, hasukappu, parsley, 0020. The term “carbonated beverage' generally refers to butter, butter oil, buttermilk, birch, honey, patchouli, pep beverages having carbon dioxide gas injected into water and permint, bagbean, fermented alcoholic beverages, fermented beverages further containing Sweeteners, acidulants, flavor sea urchinlk, fermented , passion fruit, hatsutake ings and the like, but according to the invention the term ivy, buffaloberry, Job’s tears, hanasuge, banana, Vanilla, “carbonated beverage also includes carbon dioxide-con Chinese chive, honeysuckle, papaya, burberry, hamago, taining alcohol beverages. hamasuge, rugosa rose, hama fang feng, winter bloom, rose, palma mallowa, Sugar apple, ling Zhi, hikiokoshi, water 0021. As examples there may be mentioned carbonated chestnut, pistachio, hyssop, hickory, peanut, cypress, hiba, water, carbonated beverages (Soda pop, lemonade, etc.) with popsissewa, himehagi, hyacinth, hiratake, loquat, areca nut, added flavors such as lemon, lemon-lime, lime, orange, feijoa, Fenugreek, fennel, fujibakama, fujimodoki, bran, grapefruit, grape, apple and the like, ginger ale, cola car fusel oil, petitgrain, buchu, grape, wine sake cake, rose bonated beverages, fruit juice-containing carbonated bever apple, peach, beech, bunaharitake, black caraway, black ages, dairy product-containing carbonated beverages, car berry, plum, bryonia, prickly ash, primrose, prunella, blue bon dioxide-containing liquors such as canned chu-hi, berry, breadfruit, hay, bay, hazel nut, Vetiver, , saf sparkling wine, beer, low-malt beer (Happoshu) and the like, flower, pennyroyal, peppermint, Snake, pepino, peptone, although there is no limitation to these. bergamot, bergamot mint, Peru balsam, verbena, Veronica, 0022. Also, as mentioned above, the term “carbonated benzoin, rosewood, rose, horehound, haw, houkitake, feel used for the purpose of the invention refers to an houshou, fang feng, whey, honoki, horsemint, horseradish, intense, refreshing stimulation on the throat produced by peony, hop, poppy, poplar, papaw, jojoba, Sea Squirt, bor carbon dioxide gas, or a cool (refreshing) feel created by the deaux, boronia, maitake, , marshmallow, marjoram, combination of carbon dioxide gas and flavor, and the , massoi, catnip, matico, pine, matsuoji, mushroom, additive for carbonated beverages of the invention exhibits matsutake, matsubusa, poria, mate tea, bean, marigold, a particularly notable effect for soda pop beverages with garden rhubarb, quince, mullein, mallow, mango, mangos citrus-based flavors, or cola carbonated beverages. Because teen, tangerine, chai chai hu, miso, mitsumata, bees wax, the effect is particularly notable for enhancing citrus-based meat, mimoza, myoga, milk, myrtle, milfoil, myrrh, flavors, the additive is preferably used for carbonated bev myrobalan, roasted barley, musk, gromwell, mesquite, erages with citrus-based flavors. meadowsweet, motherwort, maple, melissa, melilot, melon, Sundew, cultured Moniliaceae solution, fir, peach, Jews EXAMPLES mallow, yakuchi, bayberry, peach, eucalyptus, yukinoshita, , yucca, lily, leaf vegetables, yoroigusa, lions foot, litchi, 0023 The present invention will now be explained in life everlasting flower, lime, lilac, rakanka, long-leaved greater detail through examples. US 2008/005 0500 A1 Feb. 28, 2008

Production Example 1 hexane layers were combined and concentrated under reduced pressure for removal of the hexane to obtain 8.4g Crude Silanthol 1 of a crude extract. Yield: 2.8% (spilanthol content: 9.5%). 0024. To 10 kg of dried flower heads of Spilanthes 0031. An 8.4 g portion of the crude extract was fraction acmella (crushed to about 5 mm) there was added 100 kg of ated (elution with n-hexane:ethyl acetate=8:2) by silica gel 99 vol% ethanol, and extraction was carried out at 75° C. column chromatography (200 g of silica gel, d5 cm), and reflux temperature for 5 hours. After cooling the extract the spilanthol fraction (Rf value=0.2-0.3, n-hexane:ethyl solution to 40° C., the solid and liquid portions were acetate=7:3) was separated off and the solvent was distilled separated with a centrifugal separator and the extract was off under reduced pressure to obtain 2.76 g of a crude concentrated to 20 kg under reduced pressure. After adding spilanthol fraction 1. The crude spilanthol fraction 1 was 0.2 kg of active carbon to the concentrate and stirring for 1 then subjected to simple distillation and purification (180° hour, diatomaceous earth was added, pressure filtration was C.) using a Kugel-Rohr distilling apparatus under reduced performed to remove the active carbon, and the extract was pressure (0.1 mmHg) to obtain 0.98 g of a crude spilanthol further concentrated under reduced pressure to obtain 0.43 fraction 2. Yield: 0.33% (spilanthol content: 41.9%). kg of a Spilanthes acmella concentrate. Next, 2 kg of 0032. An 0.98 g portion of the crude spilanthol fraction distilled water was added to the concentrate and extraction was further fractionated (elution with n-hexane:ethyl was performed three times with 2 kg of ethyl acetate. acetate=95:5-90:10) by silica gel column chromatography 0.025 The extracted ethyl acetate layers were pooled, (200 g of silica gel, d5 cm), and then the spilanthol fraction diatomaceous earth was added, pressure filtration was per (Rf value=0.2, n-hexane:ethyl acetate=7:3) was separated formed, and the mixture was concentrated under reduced off and the solvent was distilled off under reduced pressure pressure to obtain 0.31 kg of a Spilanthes acmella crude to obtain 0.52g of purified spilanthol. Yield: 0.17%. Spilan extract. Yield: 3.1%. Spilanthol content: 12.4%. thol content: 98 wt %. The spilanthol structure was con 0026. After combining 100 g of the Spilanthes acmella firmed by proton and 13C NMR measurement in comparison crude extract to 100 g of fatty acid triglycerides, a reduced with the known published data. pressure thin-film distillation apparatus was used for distil 0033. A 0.104 g portion of the purified spilanthol was lation at a degree of vacuum of 3-5 Pa and a vaporization diluted with 2000 g of a 50 wt % ethanol solution to prepare surface temperature of 110-150° C., to obtain 33.3 g of a purified spilanthol Solution with a spilanthol concentration distillate. Yield: 33%. Spilanthol content: 38.0 wt %. of 50 ppm (w/w). 0027. A 0.1 g portion of the distillate was diluted with Example 1 760 g of a 50 wt % ethanol aqueous solution, and after cooling to 5° C., diatomaceous earth was added and the Diet Soda Pop Beverage mixture was filtered to prepare a crude spilanthol solution 1 with a spilanthol concentration of 50 ppm (w/w). 0034) To 295.22 g of distilled water there were added 0.08 g of sucralose, 0.3 g of Acesulfame K, 1 g of citric acid, Production Example 2 0.8 g of malic acid, 0.5 g of vitamin C, 1.5 g of Soda-pop flavoring (product of Ogawa & Co., Ltd.) and 0.6 g of the Crude Spilanthol 2 crude spilanthol solution of Production Example 1, and the components were uniformly dissolved. The solution was 0028. With 100 g of the Spilanthes acmella crude extract cooled to 5°C. in ice water and weighed out to 75 g in a 250 of Production Example 1 (spilanthol content: 12.4%) there ml Volume can. was mixed 50 g of fatty acid triglycerides, and a reduced pressure thin-film distillation apparatus was used for distil 0035 A diet soda pop carbonated beverage according to lation at a degree of vacuum of 4-5 Pa and a vaporization the invention was prepared by further adding 175 g of surface temperature of 120° C., to obtain 12.3 g of distillate. carbonated water to the Solution. A diet Soda pop carbonated Yield: 12.3%. Spilanthol content: 67.3 wt %. beverage was also prepared in the same manner by addition of the crude spilanthol solution 2 of Production Example 2. 0029. A 0.1 g portion of the distillate was diluted with 1346 g of a 50 wt % ethanol aqueous solution, and after Comparative Example 1 cooling to 5° C., diatomaceous earth was added and the mixture was filtered to prepare a crude spilanthol solution 2 0036) To 295.22 g of distilled water there were added with a spilanthol concentration of 50 ppm (w/w). 0.08 g of sucralose, 0.3 g of Acesulfame K, 1 g of citric acid, 0.8 g of malic acid, 0.5 g of vitamin C, 1.5 g of Soda-pop Production Example 3 flavoring (product of Ogawa & Co., Ltd.) and 0.6 g of a 50 wt % ethanol aqueous solution, and the components were Purified Spilanthol uniformly dissolved. 0030) A300 g portion of dried flower heads of Spilanthes 0037. The solution was cooled to 5° C. in ice water and acmella was subjected to reflux extraction for 1 hour with weighed out to 75 g in a 250 ml volume can. A diet soda pop 3200 g of 95 vol% ethanol. The extract solution was cooled, beverage for Comparative Example 1 was prepared by the solid and liquid portions were separated, and diatoma further adding 175 g of carbonated water to the solution. ceous earth was added for filtration. The filtration was concentrated under reduced pressure to remove the ethanol, Test Example 1 and then 300 g of water was added and extraction was 0038. The tastes of the diet soda pop beverage of performed three times with 300 ml of hexane. The extracted Example 1 and the diet Soda pop beverage of Comparative US 2008/005 0500 A1 Feb. 28, 2008

Example 1 were compared by an organoleptic evaluation Example 2 was prepared by further adding 212.5 g of with a panel of 20 experienced evaluators. The evaluation of carbonated water to the solution. carbonated stimulation and flavor strength was conducted on a 7-level scale centered around 4 points as equivalent to the Test Example 2 comparative example. The point averages and comments on 0049. The tastes of the ginger ale beverage of Example 2 flavor are shown in Table 1. and the ginger ale beverage of Comparative Example 2 were (Score System) compared by an organoleptic evaluation with a panel of 20 experienced evaluators. The evaluation of carbonated Stimu 0.039 Very strong flavor (highly desirable): 7 points lation and flavor strength was conducted on a 7-level scale 0040 Strong flavor (desirable): 6 points centered around 4 points as equivalent to the comparative example. The point averages and comments on flavor are 0041. Somewhat strong flavor (somewhat desirable): 5 shown in Table 2. The score system was the same as for Test points Example 1. 0.042 Equivalent: 4 points TABLE 2 0043. Somewhat weak flavor (somewhat undesirable): 3 points Carbonated Strength of stimulation flavor Comment 0044) Weak flavor (undesirable): 2 points Comparative 4.0 4.0 Example 2 0045 Very weak flavor (highly undesirable): 1 point Example 2 6.4 6.O Fresh, pleasant feel on throat TABLE 1. Carbonated Strength of stimulation flavor Comment 0050. As shown in Table 2, addition of the crude spilan thol to the ginger ale beverage produced particularly strong Comparative 4.0 4.0 carbonation-attributed stimulation with enhanced flavor Example 1 Example 1 6.6 5.5 Fresh, pleasant compared to the comparative example. Crude feel on throat spilanthol 1 Example 3 Example 1 6.2 5.8 Cool and Crude refreshing spilanthol 2 Diet Cola Beverage 0051) To 142.65 g of distilled water there were added 0.45 g of aspartame, 0.6 g of citric acid, 1 g of phosphoric 0046. As shown in Table 1, addition of the crude spilan acid, 0.1 g of caffeine, 2.7 g of caramel, 1 g of cola flavoring thol to the diet Soda pop beverage produced particularly (product of Ogawa & Co., Ltd.) and 1.5 g of the crude strong carbonation-attributed stimulation with enhanced fla spilanthol solution 2 of Production Example 2, and the Vor compared to the comparative example. components were uniformly dissolved. The solution was cooled to 5° C. in ice water and weighed out to 37.5 g in a Example 2 250 ml volume can. Ginger Ale Beverage 0052 A diet cola beverage according to the invention was 0047. To 15.61 g of distilled water there were added prepared by further adding 212.5g of carbonated water to 131.4 g of high-fructose corn syrup, 0.7 g of citric acid, 0.8 the Solution. A diet cola beverage was also prepared in the g of phosphoric acid, 0.14 g of caramel, 0.05 g of caffeine, same manner by addition of the purified spilanthol solution 1.0 g of ginger ale flavoring (product of Ogawa & Co., Ltd.) 3 of Production Example 3. and 0.3 g of the crude spilanthol solution 2 of Production Example 2, and the components were uniformly dissolved. Comparative Example 3 The solution was cooled to 5°C. in ice water and weighed 0053) To 142.65 g of distilled water there were added out to 37.5 g in a 250 ml Volume can. Aginger ale beverage 0.45 g of aspartame, 0.6 g of citric acid, 1 g of phosphoric according to the invention was prepared by further adding acid, 0.1 g of caffeine, 2.7 g of caramel, 1 g of cola flavoring 212.5g of carbonated water to the solution. (product of ogawa & Co., Ltd.) and 1.5 g of a 50 wt % ethanol aqueous Solution, and the components were uni Comparative Example 2 formly dissolved. Ginger Ale Beverage 0054 The solution was cooled to 5° C. in ice water and weighed out to 37.5 g in a 250 ml volume can. A diet cola 0048. To 15.61 g of distilled water there were added beverage for Comparative Example 3 was prepared by 131.4 g of high-fructose corn syrup, 0.7 g of citric acid, 0.8 g of phosphoric acid, 0.14 g of caramel, 0.05 g of caffeine, further adding 212.5g of carbonated water to the solution. 1.0 g of ginger ale flavoring (product of Ogawa & Co., Ltd.) Test Example 3 and 0.3 g of a 50 wt % ethanol aqueous solution, and the components were uniformly dissolved. The Solution was 0055. The tastes of the diet cola beverage of Example 3 cooled to 5° C. in ice water and weighed out to 37.5 g in a and the diet cola beverage of Comparative Example 3 were 250 ml Volume can. Aginger ale beverage for Comparative compared by an organoleptic evaluation with a panel of 20 US 2008/005 0500 A1 Feb. 28, 2008

experienced evaluators. The evaluation of carbonated feel, Example 4 flavor strength and palatability was conducted on a 7-level scale centered around 4 points as equivalent to the com Cola Beverage parative example. The point averages and comments on 0059) To 15.2 g of distilled water there were added 129.2 flavor are shown in Table 3. The same score system was used g of high-fructose corn syrup, 0.2 g of citric acid, 0.8 g of as for Test Example 1, but evaluation of palatability was phosphoric acid, 2.5g of caramel, 0.1 g of caffeine, 1.0 g of included. cola flavoring (product of Ogawa & Co., Ltd.) and 1 g of the crude spilanthol solution 2 of Production Example 2, and the 0056 A 250 ml portion of the diet cola beverage was components were uniformly dissolved. The solution was placed in a 300 ml beaker in a refrigerator at 5° C. after cooled to 5° C. in ice water and weighed out to 37.5 g in a opening of the container, and the beverage stored for 30 250 ml Volume can. A cola beverage according to the minutes in the opened State was evaluated in the same invention was prepared by further adding 212.5 g of car manner, giving the results shown in Table 4. The score bonated water to the solution. system was the same as for Test Example 1, with evaluation centered around 4 points as equivalent to the comparative Comparative Example 4 example after 30 minutes in an opened state. Palatability was Cola Beverage also included in the evaluation as in Table 3. 0060. To 15.2 g of distilled water there were added 129.2 TABLE 3 g of high-fructose corn syrup, 0.2 g of citric acid, 0.8 g of phosphoric acid, 2.5g of caramel, 0.1 g of caffeine, 1.0 g of Strength cola flavoring (product of Ogawa & Co., Ltd.) and 1 g of a Carbonated of 50 wt % ethanol aqueous solution, and the components were stimulation flavor Palatability Comment uniformly dissolved. The solution was cooled to 5°C. in ice Comparative 4.0 4.0 4.0 water and weighed out to 37.5 g in a 250 ml volume can. A Example 3 cola beverage for Comparative Example 4 was prepared by Example 3 6.6 6.O 6.2 Strong Crude spiciness further adding 212.5g of carbonated water to the solution. spilanthol 2 with pleasant Test Example 4 aftertaste Example 3 6.6 6.1 6.8 Strong 0061 The tastes of the cola beverage of Example 4 and Purified spiciness the cola beverage of Comparative Example 4 were com spilanthol with fresh pared by an organoleptic evaluation with a panel of 20 taste experienced evaluators. The evaluation was conducted for carbonated feel, strength of flavor, aftertaste and palatability, each on a 7-level scale centered around 4 points as equiva 0057. As shown in Table 3, addition of the crude spilan lent to the comparative example. The point averages and thol or purified spilanthol to the diet cola beverage produced comments on flavor are shown in Table 5. The score system particularly strong carbonation-attributed stimulation with was the same as for Test Example 1. enhanced flavor and improved palatability as a carbonated beverage, compared to the comparative example. TABLE 5 Carbonated Strength of TABLE 4 stimulation flavor Comment Strength Comparative 4.0 4.0 Carbonated of Example 4 stimulation flavor Palatability Comment Example 4 6.1 6.6 Strong flavor with fresh feel Comparative 4.0 4.0 4.0 Example 3 Example 3 6.O 6.2 6.1 Good Crude aftertaste 0062. As shown in Table 5, addition of the crude spilan spilanthol 2 with thol to the cola beverage produced particularly strong car satisfying bonation-attributed stimulation with enhanced flavor com feel Example 3 6.1 5.8 6.4 Fresh pared to the comparative example. Purified taste with spilanthol satisfying Example 5 feel 10% Orange Juice-Added Lightly Carbonated Beverage 0.058 As shown in Table 4, addition of the crude spilan 0063) To 463 g of distilled water there were added 20 g thol or purified spilanthol to the diet cola beverage produced of 5-fold orange concentrate, 114.3 g of high-fructose corn particularly strong carbonation-attributed stimulation with syrup, 1.5g of citric acid, 0.1 g of vitamin C, 1.0 g of orange maintenance of strong flavor and high palatability as a flavoring (product of Ogawa & Co., Ltd.) and 0.1 g of the carbonated beverage after 30 minutes in an opened state, purified spilanthol solution of Production Example 3, and compared to the comparative example. the components were uniformly dissolved. US 2008/005 0500 A1 Feb. 28, 2008

0064. The solution was cooled to 5° C. in ice water and 0074 The solution was cooled to 5° C. in ice water and weighed out to 150 g in a 250 ml volume can. weighed out to 100 g in a 250 ml volume can. 0065. A 10% orange juice-added lightly carbonated bev 0075) A lemon chu-hi beverage according to the inven erage according to the invention was prepared by further tion was prepared by further adding 150 g of carbonated adding 100 g of carbonated water to the solution. water to the solution. Comparative Example 5 Comparative Example 6 10% Orange Juice-Added Lightly Carbonated Lemon Chu-Hi Beverage Beverage 0076) To 168.7 g of distilled water there were added 180 g of Vodka, 6.1 g of 5-fold concentrated transparent lemon 0066. To 463 g of distilled water there were added 20 g juice, 42 g of high-fructose corn Syrup, 0.9 g of citric acid, of 5-fold orange concentrate, 114.3 g of high-fructose corn 2 g of lemon flavoring (product of ogawa & Co., Ltd.) and syrup, 1.5g of citric acid, 0.1 g of vitamin C, 1.0 g of orange 0.3 g of a 50 wt % ethanol aqueous solution, and the flavoring (product of Ogawa & Co., Ltd.) and 0.1 g of a 50 components were uniformly dissolved. The solution was wt % ethanol aqueous solution, and the components were cooled to 5° C. in ice water and weighed out to 100 g in a uniformly dissolved. 250 ml volume can. A lemon chu-hi beverage for Compara 0067. The solution was cooled to 5° C. in ice water and tive Example 6 was prepared by further adding 150 g of weighed out to 150 g in a 250 ml volume can. carbonated water to the solution. 0068 A 10% orange juice-added lightly carbonated bev Test Example 6 erage for Comparative Example 5 was prepared by further adding 100 g of carbonated water to the solution. 0077. The tastes of the lemon chu-hi beverage of Example 6 and the lemon chu-hi beverage of Comparative Test Example 5 Example 6 were compared by an organoleptic evaluation with a panel of 20 experienced evaluators. The evaluation 0069. The tastes of the 10% orange juice-added lightly was conducted for carbonated feel, strength of flavor, after carbonated beverage of Example 5 and the 10% orange taste and palatability, each on a 7-level scale centered around juice-added lightly carbonated beverage of Comparative 4 points as equivalent to the comparative example. The point Example 5 were compared by an organoleptic evaluation averages and comments on flavor are shown in Table 7. The with a panel of 20 experienced evaluators. score system was the same as for Test Example 1. 0070 The evaluation was conducted for carbonated feel, strength of flavor, aftertaste and palatability, each on a TABLE 7 7-level scale centered around 4 points as equivalent to the Carbonated Strength of comparative example. stimulation flavor Comment 0071. The point averages and comments on flavor are Comparative 4.0 4.0 Example 6 shown in Table 6. The score system was the same as for Test Example 6 6.6 5.8 Very strong Example 1. stimulation with refreshing feel TABLE 6 Carbonated Strength of 0078. As shown in Table 7, addition of the purified stimulation flavor Comment spilanthol to the lemon chu-hi beverage produced particu Comparative 4.0 4.0 larly strong carbonation-attributed stimulation with Example 5 Example 5 5.7 4.8 Fresh feel enhanced flavor compared to the comparative example. Example 7 0072. As shown in Table 6, addition of the purified spilanthol to the 10% orange juice-added lightly carbonated Lemon Juice-Added Lightly Carbonated Beverage beverage produced particularly strong carbonation-attrib 0079) To 361.678 g of distilled water there were added uted stimulation with enhanced flavor compared to the 2.1 g of 5-fold concentrated transparent lemon juice, 95g of comparative example. high-fructose corn syrup, 25g of Sucrose, 1 g of citric acid, 0.8 g of sodium citrate, 2.86 g of vitamin C, 0.003 g of Example 6 vitamin B6, 0.007 g of calcium pantothenate, 0.05 g of safflower pigment, 0.002 g of carotene pigment, 1.0 g of Lemon Chu-Hi Beverage lemon flavoring (product of Ogawa & Co., Ltd.) and 0.5g of the crude spilanthol solution 2 of Production Example 2, 0073) To 168.7 g there were added 180g of vodka, 6.1 g and the components were uniformly dissolved. The solution of transparent lemon 5-fold concentrate, 42 g of high was cooled to 5° C. in ice water and weighed out to 122.5 fructose corn Syrup, 0.9 g of citric acid, 2 g of lemon g in a 250 ml Volume can. A lemon juice-added lightly flavoring (product of Ogawa & Co., Ltd.) and 0.3 g of the carbonated beverage according to the invention was pre purified spilanthol solution of Production Example 3, and pared by further adding 137.5 g of carbonated water to the the components were uniformly dissolved. Solution. US 2008/005 0500 A1 Feb. 28, 2008

INDUSTRIAL APPLICABILITY 23. The carbonated beverage according to claim 15, characterized in that the carbonated beverage has a citrus 0080 Addition of an additive for carbonated beverages based flavor. according to the invention to a carbonated beverage can 24. The carbonated beverage according to claim 16, provide a carbonated beverage with an enhanced and pro characterized in that the carbonated beverage has a citrus longed carbonated feel which is essential for carbonated based flavor. beverages, as well as a refreshing feel on the throat. 25. The carbonated beverage according to claim 17, 1-9. (canceled) characterized in that the carbonated beverage has a citrus 10. An additive for carbonated beverages comprising a based flavor. spilanthol or a spilanthol-containing plant extract or a plant 26. The carbonated beverage according to claim 18, essential oil. characterized in that the carbonated beverage has a citrus 11. The additive for carbonated beverages according to based flavor. claim 10, wherein the spilanthol-containing plant is Spillan 27. The carbonated beverage according to claim 19, thes acmella or Spilanthes acmella var. Oleracea. characterized in that the carbonated beverage has a citrus 12. A flavoring composition for carbonated beverages, based flavor. characterized by containing an additive for carbonated bev 28. The carbonated beverage according to claim 20, erages according to claim 10. characterized in that the carbonated beverage has a citrus 13. A flavoring composition for carbonated beverages, based flavor. characterized by containing an additive for carbonated bev 29. The carbonated beverage according to claim 21, erages according to claim 11. characterized in that the carbonated beverage has a citrus 14. A carbonated beverage characterized by containing an based flavor. additive for carbonated beverages according to claim 10. 30. A method for enhancing or maintaining the carbonated 15. A carbonated beverage characterized by containing an feel of a carbonated beverage, comprising adding an additive additive for carbonated beverages according to claim 11. for carbonated beverages according to claim 1 to a spilanthol 16. A carbonated beverage characterized by containing a content of 1-300 ppb in the carbonated beverage. flavoring composition for carbonated beverages according 31. A method for enhancing or maintaining the carbonated to claim 12. feel of a carbonated beverage, comprising adding an additive 17. A carbonated beverage characterized by containing a for carbonated beverages according to claim 11 to a spilan flavoring composition for carbonated beverages according thol content of 1-300 ppb in the carbonated beverage. to claim 13. 32. A method for enhancing or maintaining the carbonated 18. The carbonated beverage according to claim 14. feel of a carbonated beverage, comprising adding a flavoring characterized by containing spilanthol at 1-300 ppb. composition for carbonated beverages according to claim 12 19. The carbonated beverage according to claim 15, to a spilanthol content of 1-300 ppb in the carbonated characterized by containing spilanthol at 1-300 ppb. beverage. 20. The carbonated beverage according to claim 16, 33. A method for enhancing or maintaining the carbonated characterized by containing spilanthol at 1-300 ppb. feel of a carbonated beverage, comprising adding a flavoring 21. The carbonated beverage according to claim 17, composition for carbonated beverages according to claim 13 characterized by containing spilanthol at 1-300 ppb. to a spilanthol content of 1-300 ppb in the carbonated 22. The carbonated beverage according to claim 14, beverage. characterized in that the carbonated beverage has a citrus based flavor.