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(12) United States Patent (10) Patent No.: US 9,131,719 B2 Backes Et Al

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(12) United States Patent (10) Patent No.: US 9,131,719 B2 Backes Et Al US009131719B2 (12) United States Patent (10) Patent No.: US 9,131,719 B2 Backes et al. (45) Date of Patent: *Sep. 15, 2015 (54) USE OF CERTAIN NEOFLAVONOIDS FOR (56) References Cited INTENSIFYING AND/OR PRODUCINGA SENSORY MIPRESSION OF SWEETNESS U.S. PATENT DOCUMENTS 7,005,146 B2* 2/2006 Lee ............................... 424,725 (75) Inventors: Michael Backes, Holzminden (DE); 2008. O1769 12 A1 7/2008 Kuo et al. Tobias Vössing, Beverungen (DE); 2008/0305.052 A1 12/2008 Ley et al. Jakob Peter Ley, Holzminden (DE); 2010. 0233102 A1 9/2010 Krammer et al. Susanne Paetz, Höxter (DE) 2011 0160311 A1* 6/2011 Prakash et al. ................ 514,777 (73) Assignee: SYMRISE AG, Holzminden (DE) FOREIGN PATENT DOCUMENTS DE 27.01280 A1 7, 1978 (*) Notice: Subject to any disclaimer, the term of this EP 2298 084 A1 3, 2011 patent is extended or adjusted under 35 OTHER PUBLICATIONS U.S.C. 154(b) by 198 days. R.S.J. Keast and P.A.S. Breslin. An overview of binary taste-taste This patent is Subject to a terminal dis interactions. Food Quality and Preference 14 (2002) 111-124.* claimer. Li Hongfang, Ma Qingyun, Liu Yuqing, Qian Jinfu, Zhou Jun & Zhao Youxing. Chemical Constituents from Polygonum perfoliatum. Chin J Appl Environ Biol. 2009, 15(5): 615-620.* (21) Appl. No.: 13/616,134 Abu T.M. Serajuddin. Salt formation to improve drug solubility. Advanced Drug Delivery Reviews 59 (2007) 603-616.* (22) Filed: Sep. 14, 2012 Property prediction cpds 7 and 8 from “Drug Relevant Properties Predictor' found online Oct. 27, 2014 from the site: http://www. (65) Prior Publication Data rdchemicals.com/drug-relevant-properties.html. Roelens F. et al., “Regioselective synthesis and estrogenicity of (+/-)- US 2013/OO84252A1 Apr. 4, 2013 8-alkyl-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4- dihydrocoumarins”, European Journal of Medicinal Chemistry Edi tions Scientifique Elsevier, Paris, FR, vol. 40, No. 10, 2005, pp. 1042-1051, XPO27857667. Related U.S. Application Data European Search Report, European Application No. 11 181511.4. (60) Provisional application No. 61/535,127, filed on Sep. dated Jun. 13, 2012. 15, 2011. * cited by examiner (30) Foreign Application Priority Data Primary Examiner — Frederick Krass Assistant Examiner — Michael P Cohen Sep. 15, 2011 (EP) ................................... 11 181511 (74) Attorney, Agent, or Firm — Novak Druce Connolly Bove + Quigg LLP (51) Int. Cl. A2.3L I/236 (2006.01) (57) ABSTRACT A6 IK 47/22 (2006.01) The present invention primarily relates to the use of one or a A6 IK 8/49 (2006.01) plurality of neoflavonoids of formula (I) and/or one or a A61O 19/00 (2006.01) plurality of physiologically acceptable salts of one or a plu A2.3L. I./22 (2006.01) rality of neoflavonoids of formula (I) for producing a sensory A2.3L. I./226 (2006.01) impression of Sweetness (i.e. an impression of Sweetness) in CO7D 3L/20 (2006.01) an orally consumable preparation or for intensifying the sen C07C 57/52 (2006.01) sory impression of Sweetness of an orally consumable prepa C07C 57/60 (2006.01) ration comprising at least one further Sweet-tasting and/or C07C 57/64 (2006.01) Sweet-smelling Substance. The present invention further (52) U.S. Cl. relates to certain semifinished products and certain orally CPC ........... A23L I/2363 (2013.01); A23L I/22091 consumable preparations containing one or a plurality of (2013.01); A23L I/22657 (2013.01); A23L neoflavonoids of formula (I) and/or one or a plurality of I/22671 (2013.01); A61K 8/498 (2013.01); physiologically acceptable salts of one or a plurality of A61K47/22 (2013.01); A61O 19/00 (2013.01); neoflavonoids of formula (I). Finally the invention also C07C 57/52 (2013.01); C07C 57/60 (2013.01); relates to a method of producing an orally consumable prepa C07C 57/64 (2013.01); C07D 311/20 (2013.01) ration and a method of producing and/or intensifying a sen (58) Field of Classification Search sory impression of Sweetness in/of an orally consumable None preparation. See application file for complete search history. 14 Claims, No Drawings US 9, 131,719 B2 1. 2 USE OF CERTAIN NEOFLAVONOIDS FOR Sweetness effect (strong Sweet aftertaste, e.g. saccharin, INTENSIFYING AND/OR PRODUCINGA Sucralose, Stevioside, rebaudioside, neotame, advantame, SENSORY IMPRESSION OF SWEETNESS Superaspartame). Therefore it is desirable to find (Sweet) substances that The present invention primarily relates to the use of one or 5 have or impart an intensive Sweet taste similar to cane Sugar a plurality of neoflavonoids of formula (I) defined hereunder and furthermore are stable and/or can be used widely, prefer and/or one or a plurality of physiologically acceptable salts of ably in orally consumable preparations. one or a plurality of neoflavonoids of formula (I) defined Another possibility for lowering the caloric content of hereunder for producing a sensory impression of Sweetness foodstuffs or beverages—without the use of normutritive (i.e. an impression of Sweetness) in an orally consumable 10 Sweeteners—consists of reducing the Sugar content of foods preparation or for intensifying the sensory impression of and/or semi-luxury food products and adding sensorily Sweetness of an orally consumable preparation comprising at weakly perceptible or imperceptible substances, which inten least one other Sweet-tasting Substance. The present invention Sify the Sweetness indirectly or directly, as described e.g. in further relates to certain semifinished products and certain 15 WO 2005/041684. orally consumable preparations containing one or a plurality Such substances of natural origin (pyridinium betaines) are of neoflavonoids of formula (I) and/or one or a plurality of described in EP 1 291 342; however, they do not influence physiologically acceptable salts of one or a plurality of Sweet taste selectively, but also other tastes such as umami or neoflavonoids of formula (I). Finally the invention also saltiness. Moreover, the Substances disclosed can only be relates to a method of producing an orally consumable prepa purified at high cost and/or are difficult to produce syntheti ration and a method of producing and/or intensifying a sen cally. sory impression of Sweetness in/of an orally consumable The use of hesperetin is recommended in WO 2007/ preparation. 014879 A1 and phloretin is recommended in WO 2007/ Foods and semi-luxury food products that have a high 107596 A1 as an intensifier of the sweet taste of reduced Sugar content (mainly Sucrose (Saccharose), lactose, glu 25 Sugar preparations used for nutrition or for pleasure. cose or fructose or mixtures thereof), are as a rule greatly However, the comparatively low level of intensification of preferred by consumers on account of their sweetness. How Sweetness in foods and semi-luxury food products that con ever, it is generally known that a high content of carbohy tain high proportions of proteins, in particular denatured pro drates that can be easily metabolized causes a large rise in teins or polysaccharides, e.g. yoghurt products, is sometimes blood Sugar level, leads to the formation offat depots and can 30 a disadvantage when using hesperetin and phloretin. More ultimately lead to health problems such as overweight, obe sity, insulin resistance, adult-onset diabetes and the sequelae over, hesperetin also has the drawback that it is not suffi thereof. In particular, a further complication is that many of ciently effective in very acidic and carbonized applications the aforementioned carbohydrates can additionally have an Such as lemonades or cola beverages. adverse effect on dental health, as they are degraded by cer 35 Therefore it is also desirable to find a possible way of tain types of bacteria in the oral cavity, for example to lactic lowering the content of Sweet compounds, in particular acid, and can attack the enamel of juvenile or adult teeth Sweet-tasting compounds in orally consumable preparations, (caries). while the impression of Sweetness remains the same, so that Therefore it has long been an aim to reduce the Sugar reduced-Sugar preparations are obtained. In particular, there content of foods and/or semi-luxury food products as much as 40 is a need for agents that intensify a given impression of possible, and the preferred aim is to achieve this reduction Sweetness, in particular even beyond a purely additive effect. with the minimum possible decrease in the impression of Accordingly, the primary aim of the present invention was Sweetness. A corresponding measure consists of the use of to find substances (individual substances or mixtures of sub Sweeteners: these are chemically homogeneous Substances, stances) that can produce an impression of Sweetness (i.e. which themselves have no or only a very slight calorific value 45 have intrinsic Sweetness) and/or can intensify the impression and at the same time produce a strong impression of Sweet of sweetness of other sweet substances. taste; the Substances are as a rule noncariogenic (a review is Furthermore, corresponding orally consumable prepara given e.g. in Journal of the American Dietetic Association tions should be provided, for which the impression of sweet 2004, 104 (2), 255-275). The so-called bulk sweeteners such ness is produced by these Substances or whose impression of as Sorbitol, mannitol or other Sugar alcohols are admittedly 50 sweetness is intensified by these substances while the con Sometimes excellent Sweeteners and can also partially replace centration of other Sweet compounds, in particular Sweet the other food-processing properties of Sugars, but ifingested tasting compounds, is largely unaltered, or for which, while too often, lead in a certain segment of the population to the impression of Sweetness remains the same, the content of osmotically-induced digestive problems. The normutritive, other compounds producing an impression of Sweet taste is highly intensive Sweeteners are very Suitable, owing to the 55 low concentration at which they are used, for imparting decreased, preferably with no or only slight negative sensory sweetness to foodstuffs.
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