Bitter taste masking compositions and method of masking bitter taste

Patent metadata

Field	Value
Publication number	US-9596874-B2
Application number	US-201113989107-A
Country	US
Kind code	B2
Filing date	Nov 30, 2011
Priority date	Nov 30, 2010
Publication date	Mar 21, 2017
Grant date	Mar 21, 2017

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 2 OH—(CHOH) 4 —CO—NH—CH 2 —CH 2 —X;

a compound of the formula (II):

R 1 —CR 2 (OR 3 )—CO—Y;

or a mixture thereof.

First claim

The invention claimed is:

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 2 OH—(CHOH) 4 —CO—NH—CH 2 —CH 2 —X;

a compound of formula (II):
R 1 —CR 2 (OR 3 )—CO—Y; and

a flavour modulating substance of formula (III):
R 1 —CR 2 (OR 3 )—CO—NR 4 —Y′—X′;

wherein:
X represents —OH, —O(CO)R, —OPO 3 H 2 , —PO 3 H 2 , —OSO 3 H or —SO 3 H, and
R represents a C 2 -C 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 1 represents hydrogen; C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 cycloalkyl or C 3 -C 8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C 1 -C 3 alkyl; C 2 -C 3 alkenyl and C 1 -C 3 carboxyl;
R 2 represents hydrogen; C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 cycloalkyl or C 3 -C 8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C 1 -C 3 alkyl, C 2 -C 3 alkenyl and C 1 -C 3 carboxyl;
R 3 represents hydrogen; C 1 -C 3 acyl or C 1 -C 3 alkyl, each unsubstituted or substituted with 1-3 hydroxyl groups; and wherein
Y′ represents a covalent bond, C 1 -C 5 alkylene or C 2 -C 5 alkenyl, each unsubstituted or substituted with 1-5 substituents selected from hydroxyl, C 1 -C 3 alkoxyl and C 1 -C 3 acyl;
X′ represents phenyl, substituted with one or more substituents selected from hydroxyl, C 1 -C 3 alkoxyl, and C 1 -C 3 hydroxyalkyl;
R 1 represents hydrogen; C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 cycloalkyl or C 3 -C 8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, oxo, C 1 -C 3 alkyl, C 2 -C 3 alkenyl, C 1 -C 3 alkoxyl, C 1 -C 3 acyl and C 1 -C 3 carboxyl;
R 2 represents hydrogen; C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 cycloalkyl, or C 3 -C 8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C 1 -C 3 alkyl, C 2 -C 3 alkenyl and C 1 -C 3 carboxyl;
R 3 represents hydrogen; or C 1 -C 3 acyl or C 1 -C 3 alkyl, each unsubstituted or substituted with 1-3 hydroxyl groups; and
R 4 represents hydrogen; C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 1 -C 3 acyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkenyl or C 1 to C 6 acyl, each unsubstituted or substituted with 1-6 substituents selected from hydroxyl, C 1 -C 3 alkyl and C 2 -C 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 2 OH—(CHOH) 4 —CO—NH—CH 2 —CH 2 —X;

a compound of formula (II):
R 1 —CR 2 (OR 3 )—CO—Y; and

a flavour modulating substance of formula (III):
R 1 —CR 2 (OR 3 )—CO—NR 4 —Y′—X′;

wherein:
X represents —OH, —O(CO)R, —OPO 3 H 2 , —PO 3 H 2 , —OSO 3 H or —SO 3 H, and
R represents a C 2 -C 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 1 represents hydrogen; C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 cycloalkyl or C 3 -C 8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C 1 -C 3 alkyl; C 2 -C 3 alkenyl and C 1 -C 3 carboxyl;
R 2 represents hydrogen; C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 cycloalkyl or C 3 -C 8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C 1 -C 3 alkyl, C 2 -C 3 al

Assignees

• Haseleu Gesa
• Lubian Elisabetta
• Renes Harry
• Winkel Cornelis
• Givaudan Sa

Inventors

• Haseleu Gesa
• Lubian Elisabetta
• Renes Harry
• Winkel Cornelis

Classifications

• A23L27/86 Primary

  Addition of bitterness inhibitors · CPC title

• A23L27/202

  Aliphatic compounds · CPC title

• A23L27/88

  Taste or flavour enhancing agents · CPC title

• A23L27/40

  Table salts; Dietetic salt substitutes · CPC title

• A23C9/1544 Primary

  Non-acidified gels, e.g. custards, creams, desserts, puddings, shakes or foams, containing eggs or thickening or gelling agents other than sugar; Milk products containing natural or microbial polysaccharides, e.g. cellulose or cellulose derivatives; Milk products containing nutrient fibres · CPC title