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(19) TZZ¥ZZ_T (11) EP 3 005 884 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A23L 27/10 (2016.01) A23L 7/126 (2016.01) 19.04.2017 Bulletin 2017/16 A21D 2/26 (2006.01) A21D 2/36 (2006.01) A23L 2/56 (2006.01) A61Q 11/00 (2006.01) (2017.01) (2006.01) (21) Application number: 15189164.5 A61K 8/97 A61K 36/232 A23L 23/00 (2016.01) (22) Date of filing: 09.10.2015 (54) TASTE MODULATOR AND METHOD OF USE THEREOF GESCHMACKSMODULATOR UND VERFAHREN ZUR VERWENDUNG DAVON MODULATEUR DE GOÛT ET SON PROCÉDÉ D’UTILISATION (84) Designated Contracting States: • JOHN, Thumpalasseril V. AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Morganville, NJ 07751 (US) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO • KIM, Jung-A PL PT RO RS SE SI SK SM TR Edgewater, NJ 07020 (US) • SINGH, Ajay Pratap (30) Priority: 10.10.2014 US 201414511963 Highland Park, NJ 08904 (US) (43) Date of publication of application: (74) Representative: Lawrence, John 13.04.2016 Bulletin 2016/15 Barker Brettell LLP 100 Hagley Road (73) Proprietor: International Flavors & Fragrances Inc. Edgbaston New York, NY 10019 (US) Birmingham B16 8QQ (GB) (72) Inventors: (56) References cited: • CHIN, Hsi-Wen EP-A1- 2 641 479 WO-A1-2013/085014 Tinton Falls, NJ 07724 (US) JP-A- 2006 191 826 JP-A- 2007 176 919 JP-B1- 4 606 505 Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 3 005 884 B1 Printed by Jouve, 75001 PARIS (FR) EP 3 005 884 B1 Description Background 5 [0001] Health practitioners have been promoting the benefits of whole grain foods. The importance of increasing whole grain consumption is reflected in the changes in recommendations set forth by government and health organization expert groups. In the Healthy People 2010 Report (National Academy Press, 1999), it is recommended that for a 2,000 calorie diet, individuals two years and older should consume at least six daily servings of grain products with at least three being whole grains. In the 2005 Dietary Guidelines for Americans it is recommended that consumers should eat 10 three or more ounce equivalents of whole grain foods each day, with the rest coming from enriched or whole grain flours. In general, at least half of the intake should come from whole grains. The American Heart Association, American Diabetes Association and the American Cancer Society also make specific recommendations regarding increasing the consump- tion of whole grains. [0002] Despite the well-documented nutritional advantages of eating whole grain products as compared to refined 15 flour products, consumers often like refined breads better than whole wheat breads, indicating that sensory properties are a barrier to consumption of whole wheat bread (Bakke & Vickers (2007) J. Food Sci. 72:S473-S480; Moskowitz, et al. (2012) J. Agric. Food Chem. 60:11245-11252). Currently, in the United States, consumption of white bread made from refined wheat flour is greater than that of whole wheat bread. Such consumer preference for refined flour products may limit the use of current whole grain wheat flours in bakery and snack products. 20 [0003] Improving the palatability of whole grain foods would help promote the acceptance and consumption of the healthful whole grain foods by consumers. In this respect, the use of methylsulfonylmethane to reduce bitterness and undesirable flavors in various food products, including grain products, has been suggested. See WO 2010/141889. WO 2013/085014 and JP 2007176919 describe a taste-masking compositions comprising a vegetable extract, including Angelica keiskei. However, there remains a need in the art to develop nutritious, high fiber food products and fiber 25 supplements which have a texture and taste more palatable to a number of consumers. Summary of the Invention [0004] The invention provides a method of reducing an undesirable taste in a product selected from the group consisting 30 of a food product, a dental product, an oral hygiene product and a medicinal product comprising the step of incorporating a taste-masking composition, wherein the taste-masking composition comprises a taste-masking effective amount rang- ing from 1 to 5000 ppm by weight of the composition of an Angelica root extract, and wherein the Angelica root extract is prepared by a process comprising the steps of: (i) submerging a root of an Angelica sinensis in a solvent selected from the group consisting of water, an organic solvent and a mix thereof; (ii) circulating the solvent continuously through 35 the root of the Angelica sinensis at a temperature ranging from room temperature to 100 °C to provide a soluble extract; and (iii) collecting the soluble extract from step (ii) and evaporating the solvent to provide the Angelica root extract. [0005] The present invention relates to a novel taste-masking composition and its unexpected advantageous use in reducing an undesirable taste in a food product ( e.g., a beverage, broth, or whole grain food product), a dental product, an oral hygiene product or a medicinal product. Specifically, the present invention relates to the taste-masking composition 40 comprising a taste-masking effective amount of an Angelica sinensis. extract. [0006] The present invention also relates to the surprising finding of the unexpected effectiveness of the taste-masking composition provided above in reducing an undesirable taste in a food product ( e.g., a beverage, broth, or whole grain food product), a dental product, an oral hygiene product or a medicinal product. [0007] The present invention further relates to a method of reducing an undesirable taste in a food product, a dental 45 product, an oral hygiene product or a medicinal product through the incorporation of the taste-masking composition provided above. [0008] These and other embodiments of the present invention will be apparent by reading the following specification. Brief Description of the Drawings 50 [0009] Figure 1 shows the flavor profile of a wheat cracker containing an extract of Angelica sinensis root. N=11. * Directional difference at p=0.10. ** Significant difference between the two samples at p=0.05. 55 Figure 2 shows the number of samples preferred in a paired comparison test between a basic wheat cracker and a wheat cracker treated with Angelica root extract. N=22. 2 EP 3 005 884 B1 Detailed Description of the Invention [0010] An extract of Angelica root is known for its medicinal use. It also has the organoleptic characteristics of herba- ceous, celery, hay, grainy, woody, bitter, dried and cardboard and is therefore used in perfumery and flavoring. It has 5 now been surprisingly found that at a taste-masking effective amount theAngelica sinensis root extract is effective in masking the off-flavors associated with various products and, in particular, food products such as whole grain foods. Specifically, water and/or organic solvent extracts of root samples of A. sinensis and A. archangelica improve the taste of whole grain foods by reducing bitter and astringent tastes and the harsh mouthfeel of whole grain products such as bread, crackers and pasta. In addition, Angelica root extracts were found to reduce bitter, metallic, astringent, and off- 10 taste/linger of beverages and broths. Therefore, the present invention provides a method for reducing an undesirable taste of various products such as food products by adding an Angelica sinensis root extract as described herein. [0011] Angelica sinensis, also known as Dong Quai, is perennial herb used in traditional Chinese herbal medicine. A. sinensis contains a number of compounds including, but not limited to vitamin B12, vitamin E, carotene, pantothenic acid, folic acid, folinic acid, biotin, nicotinic acid, nicotinamide, sucrose, butylidene phthalide, n-valerophenone-o-car- 15 boxylic acid dehydrophthalic anhydride, beta-sitosterol, sitosterol-D-glucoside, monoterpene hydrocarbons, monoter- pene alcohols, oxygenated sesquiterpenes, ethyl ethers of monoterpene alcohols, ethyl sterols of long chain fatty acids, falcarinol, falcarindiol, falcarinolone, choline, scopoletin, archangelicin, 8(S),9(R)-9-angeloyl-oxy-8,9-dihydrooroselol, psoralen, bergapten, xanthotoxin, chalcones such as asitaba-chalcone, 4-hydroxyderricin, water soluble tannin,α- pinene, myrcene, p-cymene, oxypeucedanin, imperatorin, isoimeratorin, ferulic acid, columbianetin, columbianetin ac- 20 etate, columbiadin, osthol, isoimperatorin, columbianetin-β-D-glucopyranoside, and AR-4E-2, 1, safrole, isosafrole, n- dodecanol, n-tetradecanol, palmitic acid. See, Monograph Angelica sinensis (2004) Alter. Med. Rev. 9:429-433; Noé (1998) J. Naturopathic Med. 7:66-72. In addition, A. sinensis contains alkyl phthalides such as ligustilide, (Z)-ligustilide, (Z)-6,7-epoxyligustilide, angelicide, (Z)-butylidene phthalide, butyl-phthalide, and 2,4-dihydrophthalic anhydride, which are the major components of the essential oil fraction of the roots. The non-volatile constituents reported are phenylpro- 25 panoids ((E)-ferulic acid coniferyl ferulate); benzenoids (valerophenone-o-carboxylic acid and vanillic acid); and cou- marins (angelol G, angelicone and umbelliferone. See, WHO Monographs on Selected Medicinal Plants (2004) Vol. 2, pages 25-34. Other known components found in the root ofA. sinensis include, but are not limited to, alanine,α - tocopherol, angelic acid, Angelica polymorpha alkaloid, Angelica polysaccharide-AS-1, compound E-232, angelicone, angelol, arachidonic acid, brefeldin A, cadinene, carvacrol, choline, dodecan-1-ol, GABA, gamma-aminobutyric acid, 30 lignoceric acid, n-tetradecane, n-valerophenone-o-carbonic acid, and neoangelide. See, Dr. Duke’s Phytochemical and Ethnobotanical Databases provided by the Agricultural Research Service, Germplasm Resources Information Network.

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