Bitter taste masking compositions and method of masking bitter taste

Abstract

A composition for masking the bitter taste of potassium chloride or other potassium salt used in a consumable product as a substitute, in whole or in part, for common table salt, said composition comprising a sugar alcohol and a compound of formula (I)
CH.sub.2OH(CHOH).sub.4CONHCH.sub.2CH.sub.2X;
a compound of the formula (II):
R.sup.1CR.sup.2(OR.sup.3)COY;
or a mixture thereof.

Claims

1. A method of masking the bitter taste associated with the use in a consumable product of potassium chloride or another potassium salt, said method comprising the step of adding to said product a bitter masking composition comprising a sugar alcohol together with at least two of: a compound of formula (I):
CH.sub.2OH(CHOH).sub.4CONHCH.sub.2CH.sub.2X; a compound of formula (II):
R.sup.1CR.sup.2(OR.sup.3)COY; and a flavour modulating substance of formula (III):
R.sub.1CR.sub.2(OR.sub.3)CONR.sub.4YX; wherein: X represents OH, O(CO)R, OPO.sub.3H.sub.2, PO.sub.3H.sub.2, OSO.sub.3H or SO.sub.3H, and R represents a C.sub.2-C.sub.10 group comprising at least one carboxylic acid group, or edible salts thereof; Y represents either (i) a substituted or unsubstituted six membered heterocyclic ring, comprising at least two nitrogen atoms, wherein if substituted the heterocyclic ring is substituted with one or more substituents selected from the group of amino; hydroxyl; oxo; alkyl; and an esterified or unesterified monosaccharide unit, wherein if esterified said monosaccharide unit is esterified with one or more mono-, di- and/or triphosphate groups; or (ii) a bicyclic system comprising a five membered heterocyclic ring and a six membered heterocyclic ring, each ring comprising at least two nitrogen atoms, and each ring being unsubstituted or substituted with one or more substituents selected from the group of amino; hydroxyl; oxo; alkyl; and an esterified or unesterified monosaccharide unit, wherein if esterified said monosaccharide unit is esterified with one or more mono-, di- and/or triphosphate groups; R.sup.1 represents hydrogen; C.sub.1-C.sub.8 alkyl, C.sub.2-C.sub.8 alkenyl, C.sub.3-C.sub.8 cycloalkyl or C.sub.3-C.sub.8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C.sub.1-C.sub.3 alkyl; C.sub.2-C.sub.3 alkenyl and C.sub.1-C.sub.3 carboxyl; R.sup.2 represents hydrogen; C.sub.1-C.sub.8 alkyl, C.sub.2-C.sub.8 alkenyl, C.sub.3-C.sub.8 cycloalkyl or C.sub.3-C.sub.8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C.sub.1-C.sub.3 alkyl, C.sub.2-C.sub.3 alkenyl and C.sub.1-C.sub.3 carboxyl; R.sup.3 represents hydrogen; C.sub.1-C.sub.3 acyl or C.sub.1-C.sub.3 alkyl, each unsubstituted or substituted with 1-3 hydroxyl groups; and wherein Y represents a covalent bond, C.sub.1-C.sub.5 alkylene or C.sub.2-C.sub.5 alkenyl, each unsubstituted or substituted with 1-5 substituents selected from hydroxyl, C.sub.1-C.sub.3 alkoxyl and C.sub.1-C.sub.3 acyl; X represents phenyl, substituted with one or more substituents selected from hydroxyl, C.sub.1-C.sub.3 alkoxyl, and C.sub.1-C.sub.3 hydroxyalkyl; R.sub.1 represents hydrogen; C.sub.1-C.sub.8 alkyl, C.sub.2-C.sub.8 alkenyl, C.sub.3-C.sub.8 cycloalkyl or C.sub.3-C.sub.8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, oxo, C.sub.1-C.sub.3 alkyl, C.sub.2-C.sub.3 alkenyl, C.sub.1-C.sub.3 alkoxyl, C.sub.1-C.sub.3 acyl and C.sub.1-C.sub.3 carboxyl; R.sub.2 represents hydrogen; C.sub.1-C.sub.8 alkyl, C.sub.2-C.sub.8 alkenyl, C.sub.3-C.sub.8 cycloalkyl, or C.sub.3-C.sub.8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C.sub.1-C.sub.3 alkyl, C.sub.2-C.sub.3 alkenyl and C.sub.1-C.sub.3 carboxyl; R.sub.3 represents hydrogen; or C.sub.1-C.sub.3 acyl or C.sub.1-C.sub.3 alkyl, each unsubstituted or substituted with 1-3 hydroxyl groups; and R.sub.4 represents hydrogen; C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.1-C.sub.3 acyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.6 cycloalkenyl or C.sub.1 to C.sub.6 acyl, each unsubstituted or substituted with 1-6 substituents selected from hydroxyl, C.sub.1-C.sub.3 alkyl and C.sub.2-C.sub.3 alkenyl, wherein the at least two of the compound of formula (I), the compound of formula (II) and the flavour modulating substance of formula (III) are present in said bitter masking composition in a concentration sufficient to mask the bitter taste associated with the use in a consumable product of potassium chloride or another potassium salt, wherein the bitter masking composition comprises the sugar alcohol together with at least two of: the compound of formula (I) in amounts of 0.2% to 5% by weight; the compound of formula (II) in amounts of 5% to 25% by weight; and the flavour modulating substance of formula (III) in amounts of 1% to 15% by weight, based on the total weight of said bitter masking composition.

2. The method according to claim 1 wherein the weight ratio of sugar alcohol to potassium salt is 1:20 to 2:1.

3. The method according to claim 1 wherein the weight ratio of sugar alcohol to potassium salt is about 1:5 to 1:1.

4. The method according to claim 1 wherein a compound of formula (I) is N-gluconyl ethanolamine, or an edible salt thereof.

5. The method according to claim 1 wherein a compound of formula (II) is selected from N-lactoyl GMP, N-lactoyl AMP, N-lactoyl CMP, N-lactoyl IMP, N-gluconyl GMP, N-gluconyl AMP, N-gluconyl CMP and N-gluconyl IMP.

6. The method according to claim 5 wherein the compound of formula (II) is in pure form or forms a part of a Maillard flavour composition.

7. The method according to claim 1 wherein the flavour modulating substance (III) is N-lactoyl tyramine.

8. The method according to claim 1 wherein the sugar alcohol is selected from the group consisting of Ethylene glycol, Glycerol, Erythritol, Threitol, Ribitol, Arabitol, Xylitol, Lyxitol, Allitol, Altritol, Glucitol (=sorbitol), Mannitol, Gulitol, Iditol, Galactitol (=dulcitol), Talitol, Lactitol, Maltitol, Cellobiitol, Raffinitol, or compounds structurally related to sugar alcohols, Inositol, Tetrahydroxycyclobutane, Pentahydroxycyclopentane, Heptahydroxycycloheptane, partially hydrolyzed polysaccharides that have undergone a NaBH4 reduction step, and derivatives thereof.

9. The method according to claim 1 wherein the sugar alcohol is mannitol.

10. A method of potentiating the bitter masking effect of sugar alcohols in consumable products containing potassium chloride or another potassium salt, said method comprising the step of adding to said consumable product at least two of: a compound of formula (I):
CH.sub.2OH(CHOH).sub.4CONHCH.sub.2CH.sub.2X; a compound of formula (II):
R.sup.1CR.sup.2(OR.sup.3)COY; and a flavour modulating substance of formula (III):
R.sub.1CR.sub.2(OR.sub.3)CONR.sub.4YX; wherein: X represents OH, O(CO)R, OPO.sub.3H.sub.2, PO.sub.3H.sub.2, OSO.sub.3H or SO.sub.3H, and R represents a C.sub.2-C.sub.10 group comprising at least one carboxylic acid group, or edible salts thereof; Y represents either (i) a substituted or unsubstituted six membered heterocyclic ring, comprising at least two nitrogen atoms, wherein if substituted the heterocyclic ring is substituted with one or more substituents selected from the group of amino; hydroxyl; oxo; alkyl; and an esterified or unesterified monosaccharide unit, wherein if esterified said monosaccharide unit is esterified with one or more mono-, di- and/or triphosphate groups; or (ii) a bicyclic system comprising a five membered heterocyclic ring and a six membered heterocyclic ring, each ring comprising at least two nitrogen atoms, and each ring being unsubstituted or substituted with one or more substituents selected from the group of amino; hydroxyl; oxo; alkyl; and an esterified or unesterified monosaccharide unit, wherein if esterified said monosaccharide unit is esterified with one or more mono-, di- and/or triphosphate groups; R.sup.1 represents hydrogen; C.sub.1-C.sub.8 alkyl, C.sub.2-C.sub.8 alkenyl, C.sub.3-C.sub.8 cycloalkyl or C.sub.3-C.sub.8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C.sub.1-C.sub.3 alkyl; C.sub.2-C.sub.3 alkenyl and C.sub.1-C.sub.3 carboxyl; R.sup.2 represents hydrogen; C.sub.1-C.sub.8 alkyl, C.sub.2-C.sub.8 alkenyl, C.sub.3-C.sub.8 cycloalkyl or C.sub.3-C.sub.8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C.sub.1-C.sub.3 alkyl, C.sub.2-C.sub.3 alkenyl and C.sub.1-C.sub.3 carboxyl; R.sup.3 represents hydrogen; C.sub.1-C.sub.3 acyl or C.sub.1-C.sub.3 alkyl, each unsubstituted or substituted with 1-3 hydroxyl groups; and wherein Y represents a covalent bond, C.sub.1-C.sub.5 alkylene or C.sub.2-C.sub.5 alkenyl, each unsubstituted or substituted with 1-5 substituents selected from hydroxyl, C.sub.1-C.sub.3 alkoxyl and C.sub.1-C.sub.3 acyl; X represents phenyl, substituted with one or more substituents selected from hydroxyl, C.sub.1-C.sub.3 alkoxyl, and C.sub.1-C.sub.3 hydroxyalkyl; R.sub.1 represents hydrogen; C.sub.1-C.sub.8 alkyl, C.sub.2-C.sub.8 alkenyl, C.sub.3-C.sub.8 cycloalkyl or C.sub.3-C.sub.8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, oxo, C.sub.1-C.sub.3 alkyl, C.sub.2-C.sub.3 alkenyl, C.sub.1-C.sub.3 alkoxyl, C.sub.1-C.sub.3 acyl and C.sub.1-C.sub.3 carboxyl; R.sub.2 represents hydrogen; C.sub.1-C.sub.8 alkyl, C.sub.2-C.sub.8 alkenyl, C.sub.3-C.sub.8 cycloalkyl, or C.sub.3-C.sub.8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C.sub.1-C.sub.3 alkyl, C.sub.2-C.sub.3 alkenyl and C.sub.1-C.sub.3 carboxyl; R.sub.3 represents hydrogen; or C.sub.1-C.sub.3 acyl or C.sub.1-C.sub.3 alkyl, each unsubstituted or substituted with 1-3 hydroxyl groups; and R.sub.4 represents hydrogen; C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.1-C.sub.3 acyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.6 cycloalkenyl or C.sub.1 to C.sub.6 acyl, each unsubstituted or substituted with 1-6 substituents selected from hydroxyl, C.sub.1-C.sub.3 alkyl and C.sub.2-C.sub.3 alkenyl, wherein the at least two of the compound of formula (I), the compound of formula (II) and the flavour modulating substance of formula (III) are added to said consumable product in a concentration sufficient to potentiate the bitter masking effect of sugar alcohols in consumable products containing potassium chloride or another potassium salt, wherein the step of adding comprises adding to said consumable product at least two of the compound of formula (I) in amounts of 5 to 250 ppm; the compound of formula (II) in amounts of 10 to 2500 ppm; and the flavour modulating substance of formula (III) in amounts of 10 to 100 ppm.

11. A bitter masking composition comprising a sugar alcohol and at least two of: a compound of formula (I):
CH.sub.2OH(CHOH).sub.4CONHCH.sub.2CH.sub.2X; a compound of formula (II):
R.sup.1CR.sup.2(OR.sup.3)COY; and a flavour modulating substance of formula (III):
R.sub.1CR.sub.2(OR.sub.3)CONR.sub.4YX; wherein: X represents OH, O(CO)R, OPO.sub.3H.sub.2, PO.sub.3H.sub.2, OSO.sub.3H or SO.sub.3H, and R represents a C.sub.2-C.sub.10 group comprising at least one carboxylic acid group, or edible salts thereof; Y represents either (i) a substituted or unsubstituted six membered heterocyclic ring, comprising at least two nitrogen atoms, wherein if substituted the heterocyclic ring is substituted with one or more substituents selected from the group of amino; hydroxyl; oxo; alkyl; and an esterified or unesterified monosaccharide unit, wherein if esterified said monosaccharide unit is esterified with one or more mono-, di- and/or triphosphate groups; or (ii) a bicyclic system comprising a five membered heterocyclic ring and a six membered heterocyclic ring, each ring comprising at least two nitrogen atoms, and each ring being unsubstituted or substituted with one or more substituents selected from the group of amino; hydroxyl; oxo; alkyl; and an esterified or unesterified monosaccharide unit, wherein if esterified said monosaccharide unit is esterified with one or more mono-, di- and/or triphosphate groups; R.sup.1 represents hydrogen; C.sub.1-C.sub.8 alkyl, C.sub.2-C.sub.8 alkenyl, C.sub.3-C.sub.8 cycloalkyl or C.sub.3-C.sub.8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C.sub.1-C.sub.3 alkyl; C.sub.2-C.sub.3 alkenyl and C.sub.1-C.sub.3 carboxyl; R.sup.2 represents hydrogen; C.sub.1-C.sub.8 alkyl, C.sub.2-C.sub.8 alkenyl, C.sub.3-C.sub.8 cycloalkyl or C.sub.3-C.sub.8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C.sub.1-C.sub.3 alkyl, C.sub.2-C.sub.3 alkenyl and C.sub.1-C.sub.3 carboxyl; R.sup.3 represents hydrogen; C.sub.1-C.sub.3 acyl or C.sub.1-C.sub.3 alkyl, each unsubstituted or substituted with 1-3 hydroxyl groups; and wherein Y represents a covalent bond, C.sub.1-C.sub.5 alkylene or C.sub.2-C.sub.5 alkenyl, each unsubstituted or substituted with 1-5 substituents selected from hydroxyl, C.sub.1-C.sub.3 alkoxyl and C.sub.1-C.sub.3 acyl; X represents phenyl, substituted with one or more substituents selected from hydroxyl, C.sub.1-C.sub.3 alkoxyl, and C.sub.1-C.sub.3 hydroxyalkyl; R.sub.1 represents hydrogen; C.sub.1-C.sub.8 alkyl, C.sub.2-C.sub.8 alkenyl, C.sub.3-C.sub.8 cycloalkyl or C.sub.3-C.sub.8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, oxo, C.sub.1-C.sub.3 alkyl, C.sub.2-C.sub.3 alkenyl, C.sub.1-C.sub.3 alkoxyl, C.sub.1-C.sub.3 acyl and C.sub.1-C.sub.3 carboxyl; R.sub.2 represents hydrogen; C.sub.1-C.sub.8 alkyl, C.sub.2-C.sub.8 alkenyl, C.sub.3-C.sub.8 cycloalkyl, or C.sub.3-C.sub.8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C.sub.1-C.sub.3 alkyl, C.sub.2-C.sub.3 alkenyl and C.sub.1-C.sub.3 carboxyl; R.sub.3 represents hydrogen; or C.sub.1-C.sub.3 acyl or C.sub.1-C.sub.3 alkyl, each unsubstituted or substituted with 1-3 hydroxyl groups; and R.sub.4 represents hydrogen; C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.1-C.sub.3 acyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.6 cycloalkenyl or C.sub.1 to C.sub.6 acyl, each unsubstituted or substituted with 1-6 substituents selected from hydroxyl, C.sub.1-C.sub.3 alkyl and C.sub.2-C.sub.3 alkenyl, wherein the at least two of the compound of formula (I), the compound of formula (II) and the flavour modulating substance of formula (III) are present in said bitter masking composition in a concentration sufficient to mask bitter taste, the compound of formula (I) is present in amounts of 0.2% to wherein said at least two of 5% by weight; the compound of formula (II) is present in amounts of 5% to 25% by weight; and the flavour modulating substance of formula (III) is present in amounts of 1% to 15% by weight, based on the total weight of said bitter masking composition.

12. The bitter masking composition according to claim 11 comprising a sugar alcohol and a compound of formula (I) and a compound of formula (II).

13. The bitter masking composition according to claim 12 wherein the sugar alcohol is mannitol.

14. The bitter masking composition according to claim 11 wherein a compound of formula (I) is N-gluconyl ethanolamine, or an edible salt thereof; a compound of the formula (II) is selected from the group consisting of N-lactoyl GMP, N-lactoyl AMP, N-lactoyl CMP, N-lactoyl IMP, N-gluconyl GMP, N-gluconyl AMP, N-gluconyl CMP and N-gluconyl IMP; and a flavour modulating substance (III) is N-lactoyl tyramine.

15. The bitter masking composition according to claim 11 wherein a compound of formula (I) is N-gluconyl ethanolamine, or an edible salt thereof; a compound of the formula (II) is selected from the group consisting of N-lactoyl GMP, N-lactoyl AMP, N-lactoyl CMP, N-lactoyl IMP, N-gluconyl GMP, N-gluconyl AMP, N-gluconyl CMP and N-gluconyl IMP.

16. The bitter masking composition according to claim 11 wherein the compound of formula (II) is employed as part of a Maillard flavour composition.

17. A consumer product containing potassium chloride or another potassium salt comprising the bitter masking composition as defined in claim 11.

18. The bitter masking composition according to claim 11 comprising a sugar alcohol, a compound of formula (I) and a flavour modulating substance of formula (III).

19. The bitter masking composition according to claim 11 comprising a sugar alcohol, a compound of formula (I), a compound of formula (II), and a flavour modulating substance of formula (III).

20. The method according to claim 1 wherein the step of adding comprises adding to said product the bitter masking composition comprising the sugar alcohol together with at least two of: the compound of formula (I) in amounts of 5 to 250 ppm; the compound of formula (II) in amounts of 10 to 2500 ppm; and the flavour modulating substance of formula (III) in amounts of 10 to 100 ppm, said amounts based on the weight of said product.

Description

EXAMPLE 1

(1) Three solutions were prepared: A 1600 ppm of KCl and 800 ppm of NaCl in water B 1600 ppm of KCl and 800 ppm of NaCl in water containing 5000 ppm of mannitol C 1600 ppm of KCl and 800 ppm of NaCl in water containing 5000 ppm of dulcitol

(2) The solutions were compared by a panel of professional tasters. They agreed that both mannitol and dulcitol mask the off-notes KCl well. However the dulcitol was noticeably better in masking and gave a more positive, described as rounded-off, perception.

EXAMPLE 2

(3) Light Margarine was obtained from a local supermarket. In one box 0.4% KCl was thoroughly mixed in (sample A) and in another box 0.4% KCl together with 0.5% mannitol, 30 ppm N-2-hydroxyethyl gluconamide and 500 ppm of a flavour containing a compound of formula (II), i.e. Lac GMP as part of a flavour preparation as prepared in WO2005/096844, was thoroughly mixed (Sample B). A panel of professional tasters compared the two samples and all agreed the sample B was significantly less bitter than sample A

EXAMPLE 3

(4) Light Margarine was obtained from a local supermarket. Three samples were prepared: A Margarine containing 0.4% KCl B Margarine containing 0.4% KCl and 0.5% mannitol C Margarine containing 0.4% KCl, 0.5% mannitol and 30 ppm N-2-hydroxyethyl gluconamide and 500 ppm of a flavour containing a compound of formula (II), i.e. Lac GMP as part of a flavour preparation as prepared in WO2005/096844.

(5) A panel of professional tasters compared the three samples and there was consensus that in sample C the KCl off-taste was better reduced than in sample B.

EXAMPLE 4

(6) A salad dressing with low salt level was prepared as follows: Water (28.92), Sugar (20.25), Colemans Mustard Powder (1.16), Salt (2.00), Egg Yolk Powder (0.58), Col Flo 67 (0.31), Guar (0.23), Xanthan (0.04), Riboflavin (0.002) and Maltodextrin (0.22) were mixed in a Termomix at high mixing speed for 3 minutes at 60 C and 1 minute at 90 C. Subsequently the Vegetable oil (32.40), was added in slowly at maximum mixing speed. At last the Vinegar 8% (13.88) is mixed in slowly.

(7) Two samples were prepared for tasting: A Salad dressing with 2% KCl B Salad dressing with 2% KCl and 0.5% dulcitol, 30 ppm N-2-hydroxyethyl gluconamide and 500 ppm of a flavour containing a compound of formula (II), i.e. Lac GMP as part of a flavour preparation as prepared in WO2005/096844

(8) The two samples were compared by a professional panel. The panel agreed that the Typical KCl bitterness tasted in sample A was almost completely masked in sample B.

EXAMPLE 5

(9) A vegetarian bouillon (5% salt) was prepared as follows: Salt (15.5), Dextrose Monohydrate (Tapioca) (15.7), Celery Oleoresin (0.02), Oleoresin Turmeric Vegex (0.03), Oleoresin Coriander Seed (0.02), Maltodextrin 5-8 DE (44.48), Vegetable Oil Soybean Refined (4), Yeast Standard Light (3), Onion Powder (0.4), Garlic Powder (0.4), White Pepper (0.05) and Potato Starch (16.4) were mixed in a dry blender. 32G of bouillon powder was dosed per liter of water.

(10) Two samples were prepared for tasting: A Bouillon with 0.4% KCl B Bouillon with 0.4% KCl and 0.5% dulcitol, 30 ppm N-2-hydroxyethyl gluconamide and 500 ppm of a flavour containing a compound of formula (II), i.e. Lac GMP as part of a flavour preparation as prepared in WO2005/096844.

(11) The two samples were compared by a professional panel. The panel agreed that sample B lacked the offnotes that were present in sample A.

EXAMPLE 6

(12) Bread was prepared by mixing 1250 g of wheat flour, 250 g of white wheat flour, 60 g of yeast. Three salt mixtures were added to separate flour blends: A 30 g NaCl B 18 g NaCl and 15 g KCl C 18 g NaCl, 15g KCl and 12 g dulcitol

(13) Doughs were prepared by mixing the ingredients and adding 900 g of water. The doughs were allowed to rise at room temperature for 2 hours and baked at 220 C for 45 minutes.

(14) A panel of professional tasters compared the breads. The reference sample A was 10 preferred. Sample B was disliked. Sample C came close to the reference bread but some off-notes were noticeable.

EXAMPLE 7

(15) Light margarine was obtained from a supermarket. KCl at 0.4% was thoroughly mixed into one box containing the margarine to give a sample A. In another box, 0.4% KCl, together with dulcitol (0.5%); N-2-hydroxy gluconamide (30 ppm), N-lactoyl tyramine (90 ppm) and 500 ppm of a flavour preparation containing Lactoyl GMP and prepared according to the teaching of WO 2005/096844, to provide a sample B. A panel of professional tasters compared the two samples and all agreed that sample B was significantly less bitter and had more body and more mouthfell than sample A.