IPC분류정보
국가/구분 |
United States(US) Patent
등록
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국제특허분류(IPC7판) |
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출원번호 |
US-0989107
(2011-11-30)
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등록번호 |
US-9596874
(2017-03-21)
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우선권정보 |
GB-1020255.4 (2010-11-30) |
국제출원번호 |
PCT/EP2011/071428
(2011-11-30)
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§371/§102 date |
20130812
(20130812)
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국제공개번호 |
WO2012/072701
(2012-06-07)
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발명자
/ 주소 |
- Haseleu, Gesa
- Lubian, Elisabetta
- Renes, Harry
- Winkel, Cornelis
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출원인 / 주소 |
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대리인 / 주소 |
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인용정보 |
피인용 횟수 :
0 인용 특허 :
3 |
초록
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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) CH2OH—(CHOH)4—CO—NH—CH2—CH2—X; a compound of th
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) CH2OH—(CHOH)4—CO—NH—CH2—CH2—X; a compound of the formula (II): R1—CR2(OR3)—CO—Y; or a mixture thereof.
대표청구항
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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 form
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): CH2OH—(CHOH)4—CO—NH—CH2—CH2—X;a compound of formula (II): R1—CR2(OR3)—CO—Y; anda flavour modulating substance of formula (III): R1—CR2(OR3)—CO—NR4—Y′—X′;wherein:X represents —OH, —O(CO)R, —OPO3H2, —PO3H2, —OSO3H or —SO3H, andR represents a C2-C10 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;R1 represents hydrogen; C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl or C3-C8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C1-C3 alkyl; C2-C3 alkenyl and C1-C3 carboxyl;R2 represents hydrogen; C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl or C3-C8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C1-C3 alkyl, C2-C3 alkenyl and C1-C3 carboxyl;R3 represents hydrogen; C1-C3 acyl or C1-C3 alkyl, each unsubstituted or substituted with 1-3 hydroxyl groups; and whereinY′ represents a covalent bond, C1-C5 alkylene or C2-C5 alkenyl, each unsubstituted or substituted with 1-5 substituents selected from hydroxyl, C1-C3 alkoxyl and C1-C3 acyl;X′ represents phenyl, substituted with one or more substituents selected from hydroxyl, C1-C3 alkoxyl, and C1-C3 hydroxyalkyl;R1 represents hydrogen; C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl or C3-C8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, oxo, C1-C3 alkyl, C2-C3 alkenyl, C1-C3 alkoxyl, C1-C3 acyl and C1-C3 carboxyl;R2 represents hydrogen; C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl, or C3-C8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C1-C3 alkyl, C2-C3 alkenyl and C1-C3 carboxyl;R3 represents hydrogen; or C1-C3 acyl or C1-C3 alkyl, each unsubstituted or substituted with 1-3 hydroxyl groups; andR4 represents hydrogen; C1-C6 alkyl, C2-C6 alkenyl, C1-C3 acyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl or C1 to C6 acyl, each unsubstituted or substituted with 1-6 substituents selected from hydroxyl, C1-C3 alkyl and C2-C3 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): CH2OH—(CHOH)4—CO—NH—CH2—CH2—X;a compound of formula (II): R1—CR2(OR3)—CO—Y; anda flavour modulating substance of formula (III): R1—CR2(OR3)—CO—NR4—Y′—X′;wherein:X represents —OH, —O(CO)R, —OPO3H2, —PO3H2, —OSO3H or —SO3H, andR represents a C2-C10 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;R1 represents hydrogen; C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl or C3-C8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C1-C3 alkyl; C2-C3 alkenyl and C1-C3 carboxyl;R2 represents hydrogen; C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl or C3-C8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C1-C3 alkyl, C2-C3 alkenyl and C1-C3 carboxyl;R3 represents hydrogen; C1-C3 acyl or C1-C3 alkyl, each unsubstituted or substituted with 1-3 hydroxyl groups; and whereinY′ represents a covalent bond, C1-C5 alkylene or C2-C5 alkenyl, each unsubstituted or substituted with 1-5 substituents selected from hydroxyl, C1-C3 alkoxyl and C1-C3 acyl;X′ represents phenyl, substituted with one or more substituents selected from hydroxyl, C1-C3 alkoxyl, and C1-C3 hydroxyalkyl;R1 represents hydrogen; C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl or C3-C8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, oxo, C1-C3 alkyl, C2-C3 alkenyl, C1-C3 alkoxyl, C1-C3 acyl and C1-C3 carboxyl;R2 represents hydrogen; C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl, or C3-C8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C1-C3 alkyl, C2-C3 alkenyl and C1-C3 carboxyl;R3 represents hydrogen; or C1-C3 acyl or C1-C3 alkyl, each unsubstituted or substituted with 1-3 hydroxyl groups; andR4 represents hydrogen; C1-C6 alkyl, C2-C6 alkenyl, C1-C3 acyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl or C1 to C6 acyl, each unsubstituted or substituted with 1-6 substituents selected from hydroxyl, C1-C3 alkyl and C2-C3 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 ofthe 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): CH2OH—(CHOH)4—CO—NH—CH2—CH2—X;a compound of formula (II): R1—CR2(OR3)—CO—Y; anda flavour modulating substance of formula (III): R1—CR2(OR3)—CO—NR4—Y′—X′;wherein:X represents —OH, —O(CO)R, —OPO3H2, —PO3H2, —OSO3H or —SO3H, andR represents a C2-C10 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;R1 represents hydrogen; C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl or C3-C8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C1-C3 alkyl; C2-C3 alkenyl and C1-C3 carboxyl;R2 represents hydrogen; C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl or C3-C8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C1-C3 alkyl, C2-C3 alkenyl and C1-C3 carboxyl;R3 represents hydrogen; C1-C3 acyl or C1-C3 alkyl, each unsubstituted or substituted with 1-3 hydroxyl groups; and whereinY′ represents a covalent bond, C1-C5 alkylene or C2-C5 alkenyl, each unsubstituted or substituted with 1-5 substituents selected from hydroxyl, C1-C3 alkoxyl and C1-C3 acyl;X′ represents phenyl, substituted with one or more substituents selected from hydroxyl, C1-C3 alkoxyl, and C1-C3 hydroxyalkyl;R1 represents hydrogen; C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl or C3-C8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, oxo, C1-C3 alkyl, C2-C3 alkenyl, C1-C3 alkoxyl, C1-C3 acyl and C1-C3 carboxyl;R2 represents hydrogen; C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl, or C3-C8 cycloalkenyl, each unsubstituted or substituted with 1-8 substituents selected from hydroxyl, C1-C3 alkyl, C2-C3 alkenyl and C1-C3 carboxyl;R3 represents hydrogen; or C1-C3 acyl or C1-C3 alkyl, each unsubstituted or substituted with 1-3 hydroxyl groups; andR4 represents hydrogen; C1-C6 alkyl, C2-C6 alkenyl, C1-C3 acyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl or C1 to C6 acyl, each unsubstituted or substituted with 1-6 substituents selected from hydroxyl, C1-C3 alkyl and C2-C3 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.
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