EP-4740749-A2 - USE OF 3-(3-HYDROXY-4-METHOXY-PHENYL)-1-(2,4,6-TRIHYDROXY-PHENYL)-PROPAN-1-ONE

EP4740749A2EP 4740749 A2EP4740749 A2EP 4740749A2EP-4740749-A2

Abstract

The present invention concerns the use of 3-(3-Hydroxy-4-methoxy-phenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one for masking, reducing or suppressing an unpleasant taste impression, preferably bitter, sour and/or astringent taste impression of unpleasant-tasting substances or mixture of substances, preferably bitter-, sour-, and/or astringent- tasting sub-stances or mixtures of substances, and in particular the bitter taste impression of bitter-tasting substances, and/or modulating the taste impressions selected from the group consisting of cooling, umami, fruity and spicy notes of cooling-, umami-, fruity- or spicy-tasting substances or mixture of substances, and simultaneously intensifying the sweet-taste impression of sweet-tasting substances or mixtures of substances or both sweet- and bitter-tasting tasting substances or mixture of substances.

Inventors

KRAMMER, GERHARD
LEY, JAKOB PETER
Hentschel, Fabia, Dr.
PAETZ, SUSANNE
RIESS, THOMAS
BACKES, MICHAEL

Assignees

Symrise AG

Dates

Publication Date: 20260513
Application Date: 20160428

Claims (14)

Use (a) of hesperetin dihydrochalcone (I), or - a salt of the hesperetin dihydrochalcone (I) or a mixture comprising or consisting of a plurality of salts of the hesperetin dihydrochalcone (I), or - a mixture comprising or consisting of hesperetin dihydrochalcone (I) and a salt or a plurality of salts of the hesperetin dihydrochalcone (I), as described in each case above, in a mixture comprising (b) one or more sweet-tasting substance(s) for the intensification - preferably synergistic intensification - of the sweet taste of the substance(s) (b), wherein the sweet-tasting substance(s) is/are selected from the group consisting of sodium cyclamate, acesulfame K, neohesperidine dihydrochalcone, naringin hydrochalcone, saccharin, saccharin sodium salt, aspartame, superaspartame, neotame, sucralose or naturally occurring sweeteners such as monellin, mabinlin, thaumatin, curculin, brazzein, steviolglycosides, steviosides, steviolbioside, rebaudiosides, rebaudioside A, rebaudioside C, rebaudioside D, rebaudioside M, rebaudioside Z, rubusoside, dihydroquercetin-3-acetate, transanethole, trilobatin, chlorogenic acid, mogrosides, monatin, glycyrrhetin acid and derivatives and salts thereof and phyllodulcin.
Use according to claim 1, wherein the mixture comprises unpleasant-tasting substance(s) (c) and (a) is additionally used for masking or reducing the unpleasant taste impression of an unpleasant-tasting substance(s) (c), preferably bitter-, sour-, and/or astringent-tasting substances, in particular bitter-tasting substances.
Use according to claim 1 or 2, wherein the mixture comprises both sweet-tasting substances and unpleasant-tasting substances (d), in particular bitter - tasting substances (d) and (a) is additionally used for masking or reducing the unpleasant taste impression of an unpleasant-tasting substance(s) (d).
The use of any of claims 1 to 3, wherein the mixture is an aroma composition or preparation selected from the group consisting of preparations serving for nutrition, food supplements, for oral care or for pleasure, cosmetic preparations, pharmaceutical preparations intended to be taken orally, flavouring mixtures for use in one of the preparations and semi-finished products for manufacturing one of the preparations.
Aroma composition comprising or consisting of: (a) a compound of formula (I) or a salt of the compound of formula (I) or a mixture comprising or consisting of a plurality of salts of the compound of formula (I), or a mixture comprising or consisting the compound of formula (I) and a salt or a plurality of salts of the compound of formula (I); and (b) one or more sweet-tasting substances, wherein the sweet-tasting substance(s) is/are selected from the group consisting of sodium cyclamate, acesulfame K, neohesperidine dihydrochalcone, naringin hydrochalcone, saccharin, saccharin sodium salt, aspartame, superaspartame, neotame, sucralose or naturally occurring sweeteners such as monellin, mabinlin, thaumatin, curculin, brazzein, steviolglycosides, steviosides, steviolbioside, rebaudiosides, rebaudioside A, rebaudioside C, rebaudioside D, rebaudioside M, rebaudioside Z, rubusoside, dihydroquercetin-3-acetate, transanethole, trilobatin, chlorogenic acid, mogrosides, monatin, glycyrrhetin acid and derivatives and salts thereof and phyllodulcin.
Aroma composition according to claim 5, comprising at least one or a plurality of the substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter-, sour-, and/or astringent-tasting substances, in particular bitter-tasting substances - substance(s) (d) means one or more both sweet-tasting substances and unpleasant-tasting substances, in particular bitter - tasting substances.
Aroma composition according to claim 5 or 6, further comprising (e) one or more substances to mask or reduce an unpleasant taste impression, in particular a bitter taste impression, and/or (f) one or more further substances for intensifying a sweet taste impression, and/or (g) one or more substances to mask or reduce a metallic, chalky, sour, or astringent taste impression, and/or (h) one or more substances having a taste impression selected from the group consisting of cooling, umami, fruity and spicy taste impression or mixtures thereof; wherein components (c)-(h) do not comprise hesperetin dihydrochalcone (I) or a salt of hesperetin dihydrochalcone (I).
The aroma composition according to any of claims 6 to 7, wherein the total amount of component (a) is sufficient to enhance - preferably synergistically - the sweet taste of the sweet-tasting substance, in comparison to an otherwise equivalent composition without hesperetin dihydrochalcone (I) and/or salt(s) thereof, and wherein the total amount of hesperetin dihydrochalcone (I) and/or salt(s) thereof is sufficient to reduce and/or mask the unpleasant taste of the bitter-, sour-, and/or astringent-tasting substance(s).
A preparation selected from the group consisting of (1) a preparation for nourishment, a food supplement preparation, or a preparation for oral care or pleasure, (2) a cosmetic preparation, (3) a pharmaceutical preparation intended for oral administration, (4) a flavouring mixtures for use in one of the preparations mentioned in (1) to (3), and (5) a semi-finished product for manufacturing one of the preparations mentioned in (1) to (3), wherein the preparation comprises the aroma composition as defined in claims 5 to 8.
The preparation as claimed in claim 9, selected from the group consisting of (1) a preparation for nourishment, a food supplement preparation, or a preparation for oral care or pleasure, (2) a cosmetic preparation, (3) a pharmaceutical preparation intended for oral administration, wherein the preparation (1), (2) or (3) based on its total weight comprises 0.00001% by weight (0.1 ppm) - 0.005 % by weight (50 ppm) of (i) hesperetin dihydrochalcone (I) and (ii) its salts (component (a)).
The preparation as claimed in claim 9, wherein the preparation (1), (2) or (3) based on its total weight comprises 0.00005% by weight (0.5 ppm) - 0.003 (30 ppm) of (i) hesperetin dihydrochalcone (I) and (ii) its salts (component (a)).
The preparation as claimed in claim 9, selected from the group consisting of (4) a flavouring mixtures for use in one of the preparations mentioned in (1) to (3), and (5) semi-finished products for manufacturing one of the preparations mentioned in claim 9, wherein the preparation (5) based on its total weight comprises 0.0001% by weight--95% by weight of (i) hesperetin dihydrochalcone (I) and (ii) its salts (component (a)).
A method for manufacturing of an aroma composition as defined in claims 5 to 8 or a preparation as defined in claims 9 to 12 comprising the steps (1) Providing the following components: (a) hesperetin dihydrochalcone (I) or a salt of the hesperetin dihydrochalcone (I) or a mixture comprising or consisting of a plurality of salts of the hesperetin dihydrochalcone (I) or a mixture comprising or consisting of hesperetin dihydrochalcone (I) and a salt or a plurality of salts of the hesperetin dihydrochalcone (I), and (b) one or more sweet-tasting substances wherein component (b) does not comprise hesperetin dihydrochalcone (I) or a salt of hesperetin dihydrochalcone (I) and, (2) mixing of components (a)and (b) with the further components, wherein the sweet-tasting substance(s) is/are selected from the group consisting of sodium cyclamate, acesulfame K, neohesperidine dihydrochalcone, naringin hydrochalcone, saccharin, saccharin sodium salt, aspartame, superaspartame, neotame, sucralose or naturally occurring sweeteners such as monellin, mabinlin, thaumatin, curculin, brazzein, steviolglycosides, steviosides, steviolbioside, rebaudiosides, rebaudioside A, rebaudioside C, rebaudioside D, rebaudioside M, rebaudioside Z, rubusoside, dihydroquercetin-3-acetate, transanethole, trilobatin, chlorogenic acid, mogrosides, monatin, glycyrrhetin acid and derivatives and salts thereof and phy-lodulcin.
A method for intensifying - preferably synergistically - the sweet-taste impression of sweet-tasting substances or mixtures of substances with the following step - mixing of the following components (a) hesperetin dihydrochalcone (I) or a salt of the hesperetin dihydrochalcone (I) or a mixture comprising or consisting of a plurality of salts of the hesperetin dihydro-chalcone (I) or a mixture comprising or consisting of hesperetin dihydrochalcone (I) and a salt or a plurality of salts of the hesperetin dihydrochalcone (I), and (b) one or more sweet-tasting substances, and if necessary further components, and wherein the total quantity of component (a) in the mixture is sufficient to intensify - preferably synergistically - the sweet-taste impression of sweet-tasting substances or mixtures of substances, wherein the sweet-tasting substance(s) is/are selected from the group consisting of sodium cyclamate, acesulfame K, neohesperidine dihydrochalcone, naringin hydrochalcone, saccharin, saccharin sodium salt, aspartame, superaspartame, neotame, sucralose or naturally occurring sweeteners such as monellin, mabinlin, thaumatin, curculin, brazzein, steviolgylcosides, steviosides, steviolbioside, rebaudiosides, rebaudioside A, rebaudioside C, rebaudioside D, rebaudioside M, rebaudioside Z, rubusoside, dihydroquercetin-3-acetate, transanethole, trilobatin, chlorogenic acid, mogrosides, monatin, glycyrrhetin acid and derivatives and salts thereof and phyllodulcin.

Description

FIELD OF INVENTION The present invention concerns the use of 3-(3-Hydroxy-4-methoxy-phenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one (compound of Formula (I)), in the following referred to as hesperetin dihydrochalcone (I), wherein (I) is understood to be a reference to Formula (I), or a salt of hesperetin dihydrochalcone (I) or a mixture comprising or consisting of a plurality of salts of the hesperetin dihydrochalcone (I) or a mixture comprising or consisting of hesperetin dihydrochalcone (I) and a salt or a plurality of salts of the hesperetin dihydrochalcone (I) for (i) masking, reducing or suppressing an unpleasant taste impression, preferably bitter, sour and/or astringent taste impression of unpleasant-tasting substances or mixture of substances, preferably bitter-, sour-, and/or astringent- tasting substances or mixtures of substances, and in particular the bitter taste impression of bitter-tasting substances, and/or(ii) modulating the taste impressions selected from the group consisting of cooling, sweet, umami, fruity and spicy notes of cooling-, sweet-, umami-, fruity- or spicy- tasting sub-stances or mixture of substances. The present invention also concerns aroma compositions comprising hesperetin dihydrochalcone (I) or a salt of the hesperetin dihydrochalcone (I) or a mixture comprising or consisting of a plurality of salts of the hesperetin dihydrochalcone (I) or a mixture comprising or consisting of hesperetin dihydrochalcone (I) and a salt or a plurality of salts of the hesperetin dihydrochalcone (I). The present invention also concerns preparations, in particular preparations serving for nutrition, as food supplements, for oral care or for pleasure, as cosmetics or pharmaceuticals for oral administration as well as intermediate goods comprising such an aroma com-position. In addition, the present invention concerns a method for manufacturing such aroma compositions, such preparations or such intermediate goods. Furthermore, the present invention concerns a method for masking, reducing or suppressing an unpleasant taste impression, preferably bitter, sour and/or astringent taste impression of unpleasant-tasting substances or mixture of substances, preferably bitter-, sour-, and/or astringent- tasting substances or mixtures of substances, and in particular the bitter taste impression of bitter-tasting substances. In addition, the present invention also concerns a method for modulating the taste impressions selected from the group consisting of cooling, sweet, umami, fruity and spicy notes of cooling-, sweet-, umami-, fruity- or spicy- tasting substances or mixture of substances. Further aspects of the present invention and preferred embodiments of it will emerge from the following description and the attached claims. STATE OF THE ART Foodstuffs or semi-luxury products, with a high sugar content (especially sucrose (=saccharose), lactose, glucose or fructose or mixtures of these), are generally particularly preferred by consumers because of their sweetness. On the other hand, it is well known that a high content of carbohydrates which are easy to metabolize results in a sharp increase in the blood sugar level, and the formation of fatty deposits and ultimately can lead to health problems such as obesity, adiposity, insulin-resistance, adult-onset diabetes and the associated conditions of these. In particular this is compounded by the fact that many of the stated carbohydrates can also have an adverse effect on dental health, since they are broken down in the oral cavity by certain kinds of bacteria into lactic acid, for example, which can attack the dental enamel of young and adult teeth (tooth decay). It has therefore long been an objective to reduce the sugar content of foodstuffs and/or semi-luxury foods to the absolute minimum or below. One such measure is the use of sweeteners. These are substances which in themselves have no or only a very low calorific value and which at the same time bring about a strong sweet taste impression; these substances are as a rule non-cariogenic (an overview can be found, by way of example, in the Journal of the American Dietetic Association 2004, 104 (2), 255-275). So-called bulk sweeteners such as sorbitol, mannitol or other sugar alcohols are in-deed to some extent exceptional sweeteners and can also partly replace the other characteristics of sugar for food technology purposes, but if these are ingested too often they can cause osmotic related digestive problems in some people. Non-nutritious, highly intensive sweeteners are in fact, due to their low usage concentration, well suited to providing sweetness in foodstuffs, but often demonstrate taste problems due to a time-intensity profile that differs from that of sugar (e.g. sucralose, steviosides, cyclamate), a bitter and/or astringent aftertaste (e.g. acesulfame K, saccharin, stevioside, rebaudioside) and/or pronounced additional flavour impressions (e.g. glycyrrhizic acid ammonium salt). Some of these