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US 2014/0004243 A1Published application
Salty taste enhancer
AssigneeAjinomoto Co., Inc.
InventorsYuki TAHARA, Yusuke Amino, Takami Maekawa, Yuzuru Eto, Takashi Miyaki, Wakana Saikawa, Yuko Kai, Yutaka Ishiwatari
Life of this patent
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Abstract
The present invention provides a compound having a salty taste enhance activity, and a salty taste enhancer containing the compound, and the like. The present invention relates to a salty taste enhancer for a food or drink, which contains a compound represented by the following formula: wherein each symbol is as defined in the specification, or an edible salt thereof.
Claims13
A method of enhancing salty taste of a food or drink, comprising mixing a compound represented by formula (I):
- wherein:
- R1′ to R5′ are each independently:
- (i) a hydrogen atom,
- (ii) a hydroxyl group,
- (iii) a halogen atom,
- (iv) a carboxyl group,
- (v) a C1-4 alkoxy-carbonyl group,
- (vi) a C1-4 alkoxy group,
- (vii) an amino group optionally substituted by a C1-4 alkoxy-carbonyl group,
- (viii) a cyano group,
- (ix) a nitro group,
- (x) a C1-4 alkyl group optionally substituted by 1 to 3 halogen atoms,
- (xi) a C1-4 alkyl-carbonylamino group optionally substituted by an amino group optionally substituted by a C1-4 alkoxy-carbonyl group,
- (xii) a C1-4 alkylsulfonylamino group, or
- (xiii) a C6-10 arylsulfonylamino group optionally substituted by a C1-4 alkyl group, or
- any two of R1′ to R5′ are optionally joined to form a C1-4 alkylenedioxy group,
- each R6′ is independently:
- (i) a hydrogen atom,
- (ii) a hydroxyl group,
- (iii) a C1-4 alkyl group optionally substituted by 1 to 3 substituents selected from a hydroxyl group, a alkoxy group and a C7-14 aralkyloxy group,
- (iv) a C1-4 alkoxy group,
- (v) a carboxyl group,
- (vi) a C1-4 alkoxy-carbonyl group,
- (vii) a C6-40 aryl group, or
- (viii) a carbamoyl group, or
- R6′ and R5′ are optionally joined to form a C1-4 alkylene group,
- m is an integer of 0 to 2,
- Ra′ is a hydrogen atom, a hydroxyl group, a C1-4 alkyl group or a C7-14 aralkyl group, or
- Ra′ and R5′ are optionally joined to form a C1-4 alkylene group,
- Rb′ is a hydrogen atom, a hydroxyl group, a C1-4 alkyl group or a C7-14 aralkyl group, or
- Rb′ and R6′ are optionally joined to form a carbonyl group,
- p is 0 or 1,
- U is a single bond, —NH—CH2—, —N═CR12′—, wherein R12′ is a hydrogen atom or a C1-4 alkyl group, or U is a group represented by the following formula:
- wherein:
- each Rc′ is independently:
- (i) a hydrogen atom,
- (ii) a hydroxyl group,
- (iii) a C1-4 alkyl group optionally substituted by 1 to 3 substituents selected from a hydroxyl group, a C1-4 alkoxy group and a C7-14 aralkyloxy group,
- (iv) a C1-4 alkoxy group,
- (v) a carboxyl group,
- (vi) a C1-4 alkoxy-carbonyl group,
- (vii) a C6-10 aryl group, or
- (viii) a carbamoyl group, and
- q is an integer of 1 to 3, and
- E is a hydroxyl group, an amino group, a carbamoyl group, or E is a C3-10 cycloalkyl group, a C6-14 aryl group, or an aromatic heterocyclic group, each of which is optionally substituted by 1 to 3 substituents selected from the group consisting of (a) a hydroxyl group, (b) a halogen atom, (c) a carboxyl group, (d) a alkoxy-carbonyl group, (e) a C1-4 alkoxy group, (f) an amino group optionally substituted by a C1-4 alkoxy-carbonyl group, (g) a cyano group, (h) a nitro group, (i) a C1-4 alkyl group optionally substituted by 1 to 3 halogen atoms, (j) a C1-4 alkyl-carbonylamino group optionally substituted by an amino group optionally substituted by a C1-4 alkoxy-carbonyl group, (k) a C1-4 alkylsulfonylamino group, and (l) a C6-10 arylsulfonylamino group optionally substituted by a C1-4 alkyl group,
- provided that partial structures:
- wherein * shows a binding position with a thiocarbonyl group, are not
- wherein * is as defined above,
- or an edible salt thereof,
- with a food or drink.
47 more elements
A method of adjusting salty taste of a food or drink, comprising mixing a compound represented by formula (I):
- wherein:
- R1′ to R5′ are each independently:
- (i) a hydrogen atom,
- (ii) a hydroxyl group,
- (iii) a halogen atom,
- (iv) a carboxyl group,
- (v) a C1-4 alkoxy-carbonyl group,
- (vi) a C1-4 alkoxy group,
- (vii) an amino group optionally substituted by a C1-4 alkoxy-carbonyl group,
- (viii) a cyano group,
- (ix) a nitro group,
- (x) a C1-4 alkyl group optionally substituted by 1 to 3 halogen atoms,
- (xi) a C1-4 alkyl-carbonylamino group optionally substituted by an amino group optionally substituted by a C1-4 alkoxy-carbonyl group,
- (xii) a C1-4 alkylsulfonylamino group, or
- (xiii) a C6-10 arylsulfonylamino group optionally substituted by a C1-4 alkyl group, or
- any two of R1′ to R5′ are optionally joined to form a C1-4 alkylenedioxy group,
- each R6′ is independently:
- (i) a hydrogen atom,
- (ii) a hydroxyl group,
- (iii) a C1-4 alkyl group optionally substituted by 1 to 3 substituents selected from a hydroxyl group, a C1-4 alkoxy group and a C7-14 aralkyloxy group,
- (iv) a C1-4 alkoxy group,
- (v) a carboxyl group,
- (vi) a C1-4 alkoxy-carbonyl group,
- (vii) a C6-10 aryl group, or
- (viii) a carbamoyl group, or
- R6′ and R5′ are optionally joined to form a C1-4 alkylene group,
- m is an integer of 0 to 2,
- Ra′ is a hydrogen atom, a hydroxyl group, a C1-4 alkyl group or a C7-14 aralkyl group, or
- Ra′ and R5′ are optionally joined to form a C1-4 alkylene group,
- Rb′ is a hydrogen atom, a hydroxyl group, a C1-4 alkyl group or a C7-14 aralkyl group, or
- Rb′ and R6′ are optionally joined to form a carbonyl group,
- p is 0 or 1,
- U is a single bond, —NH—CH2—, —N═CR12′—, wherein R12′ is a hydrogen atom or a C1-4 alkyl group, or U is a group represented by the following formula:
- wherein:
- each Rc′ is independently:
- (i) a hydrogen atom,
- (ii) a hydroxyl group,
- (iii) a alkyl group optionally substituted by 1 to 3 substituents selected from a hydroxyl group, a C1-4 alkoxy group and a C7-14 aralkyloxy group,
- (iv) a C1-4 alkoxy group,
- (v) a carboxyl group,
- (vi) a C1-4 alkoxy-carbonyl group,
- (vii) a C6-10 aryl group, or
- (viii) a carbamoyl group, and
- q is an integer of 1 to 3, and
- E is a hydroxyl group, an amino group, a carbamoyl group, or E is a C3-10 cycloalkyl group, a C6-14 aryl group, or an aromatic heterocyclic group, each of which is optionally substituted by 1 to 3 substituents selected from the group consisting of (a) a hydroxyl group, (b) a halogen atom, (c) a carboxyl group, (d) a C1-4 alkoxy-carbonyl group, (e) a C1-4 alkoxy group, (f) an amino group optionally substituted by a C1-4 alkoxy-carbonyl group, (g) a cyano group, (h) a nitro group, (i) a C1-4 alkyl group optionally substituted by 1 to 3 halogen atoms, (j) a C1-4 alkyl-carbonylamino group optionally substituted by an amino group optionally substituted by a C1-4 alkoxy-carbonyl group, (k) a C1-4 alkylsulfonylamino group, and (l) a C6-10 arylsulfonylamino group optionally substituted by a C1-4 alkyl group,
- provided that partial structures:
- wherein * shows a binding position with a thiocarbonyl group, are not
- wherein * is as defined above,
- or an edible salt thereof,
- with a food or drink.
47 more elements
A method of producing a food or drink, which comprises mixing a compound represented by formula (I):
- wherein:
- R1′ to R5′ are each independently:
- (i) a hydrogen atom,
- (ii) a hydroxyl group,
- (iii) a halogen atom,
- (iv) a carboxyl group,
- (v) a C1-4 alkoxy-carbonyl group,
- (vi) a C1-4 alkoxy group,
- (vii) an amino group optionally substituted by a C1-4 alkoxy-carbonyl group,
- (viii) a cyano group,
- (ix) a nitro group,
- (x) a C1-4 alkyl group optionally substituted by 1 to 3 halogen atoms,
- (xi) a C1-4 alkyl-carbonylamino group optionally substituted by an amino group optionally substituted by a C1-4 alkoxy-carbonyl group,
- (xii) a C1-4 alkylsulfonylamino group, or
- (xiii) a C6-10 arylsulfonylamino group optionally substituted by a C1-4 alkyl group, or
- any two of R1′ to R5′ are optionally joined to form a C1-4 alkylenedioxy group,
- each R6′ is independently:
- (i) a hydrogen atom,
- (ii) a hydroxyl group,
- (iii) a C1-4 alkyl group optionally substituted by 1 to 3 substituents selected from a hydroxyl group, a C1-4 alkoxy group and a C7-14 aralkyloxy group,
- (iv) a C1-4 alkoxy group,
- (v) a carboxyl group,
- (vi) a C1-4 alkoxy-carbonyl group,
- (vii) a C6-10 aryl group, or
- (viii) a carbamoyl group, or
- R6′ and R5′ are optionally joined to form a C1-4 alkylene group,
- m is an integer of 0 to 2,
- Ra′ is a hydrogen atom, a hydroxyl group, a C1-4 alkyl group or a C7-14 aralkyl group, or
- Ra′ and R5′ are optionally joined to form a C1-4 alkylene group,
- Rb′ is a hydrogen atom, a hydroxyl group, a C1-4 alkyl group or a C7-14 aralkyl group, or
- Rb′ and R6′ are optionally joined to form a carbonyl group,
- p is 0 or 1,
- U is a single bond, —NH—CH2—, —N═CR12′—, wherein R12′ is a hydrogen atom or a C1-4 alkyl group, or U is a group represented by the following formula:
- wherein:
- each Rc′ is independently:
- (i) a hydrogen atom,
- (ii) a hydroxyl group,
- (iii) a C1-4 alkyl group optionally substituted by 1 to 3 substituents selected from a hydroxyl group, a C1-4 alkoxy group and a C7-14 aralkyloxy group,
- (iv) a C1-4 alkoxy group,
- (v) a carboxyl group,
- (vi) a C1-4 alkoxy-carbonyl group,
- (vii) a C6-10 aryl group, or
- (viii) a carbamoyl group, and
- q is an integer of 1 to 3, and
- E is a hydroxyl group, an amino group, a carbamoyl group, or E is a C3-10 cycloalkyl group, a C6-14 aryl group, or an aromatic heterocyclic group, each of which is optionally substituted by 1 to 3 substituents selected from the group consisting of (a) a hydroxyl group, (b) a halogen atom, (c) a carboxyl group, (d) a C1-4 alkoxy-carbonyl group, (e) a C1-4 alkoxy group, (f) an amino group optionally substituted by a C1-4 alkoxy-carbonyl group, (g) a cyano group, (h) a nitro group, (i) a C1-4 alkyl group optionally substituted by 1 to 3 halogen atoms, (j) a C1-4 alkyl-carbonylamino group optionally substituted by an amino group optionally substituted by a C1-4 alkoxy-carbonyl group, (k) a C1-4 alkylsulfonylamino group, and (l) a C6-10 arylsulfonylamino group optionally substituted by a C1-4 alkyl group,
- provided that partial structures:
- wherein * shows a binding position with a thiocarbonyl group, are not
- wherein * is as defined above,
- or an edible salt thereof,
- with a food or drink.
47 more elements
A method of producing a food or drink having an enhanced salty taste, comprising mixing not less than an effective amount of a compound represented by formula (I):
- wherein:
- R1′ to R5′ are each independently:
- (i) a hydrogen atom,
- (ii) a hydroxyl group,
- (iii) a halogen atom,
- (iv) a carboxyl group,
- (v) a C1-4 alkoxy-carbonyl group,
- (vi) a C1-4 alkoxy group,
- (vii) an amino group optionally substituted by a C1-4 alkoxy-carbonyl group,
- (viii) a cyano group,
- (ix) a nitro group,
- (x) a C1-4 alkyl group optionally substituted by 1 to 3 halogen is atoms,
- (xi) a C1-4 alkyl-carbonylamino group optionally substituted by an amino group optionally substituted by a C1-4 alkoxy-carbonyl group,
- (xii) a C1-4 alkylsulfonylamino group, or
- (xiii) a C6-10 arylsulfonylamino group optionally substituted by a C1-4 alkyl group, or
- any two of R1′ to R5′ are optionally joined to form a C1-4 alkylenedioxy group,
- each R6′ is independently:
- (i) a hydrogen atom,
- (ii) a hydroxyl group,
- (iii) a C1-4 alkyl group optionally substituted by 1 to 3 substituents selected from a hydroxyl group, a C1-4 alkoxy group and a C7-14 aralkyloxy group,
- (iv) a C1-4 alkoxy group,
- (v) a carboxyl group,
- (vi) a C1-4 alkoxy-carbonyl group,
- (vii) a C6-10 aryl group, or
- (viii) a carbamoyl group, or
- R6′ and R5′ are optionally joined to form a C1-4 alkylene group,
- m is an integer of 0 to 2,
- Ra′ is a hydrogen atom, a hydroxyl group, a C1-4 alkyl group or a C7-14 aralkyl group, or
- Ra′ and R5′ are optionally joined to form a C1-4 alkylene group,
- Rb′ is a hydrogen atom, a hydroxyl group, a C1-4 alkyl group or a C7-14 aralkyl group, or
- Rb′ and R6′ are optionally joined to form a carbonyl group,
- p is 0 or 1,
- U is a single bond, —NH—CH2—, —N═CR12′—, wherein R12′ is a hydrogen atom or a C1-4 alkyl group, or U is a group represented by the following formula:
- wherein:
- each Rc′ is independently:
- (i) a hydrogen atom,
- (ii) a hydroxyl group,
- (iii) a C1-4 alkyl group optionally substituted by 1 to 3 substituents selected from a hydroxyl group, a C1-4 alkoxy group and a C7-14 aralkyloxy group,
- (iv) a C1-4 alkoxy group,
- (v) a carboxyl group,
- (vi) a C1-4 alkoxy-carbonyl group,
- (vii) a C6-10 aryl group, or
- (viii) a carbamoyl group, and
- q is an integer of 1 to 3, and
- E is a hydroxyl group, an amino group, a carbamoyl group, or E is a C3-10 cycloalkyl group, a C6-14 aryl group, or an aromatic heterocyclic group, each of which is optionally substituted by 1 to 3 substituents selected from the group consisting of (a) a hydroxyl group, (b) a halogen atom, (c) a carboxyl group, (d) a C1-4 alkoxy-carbonyl group, (e) a C1-4 alkoxy group, (f) an amino group optionally substituted by a C1-4 alkoxy-carbonyl group, (g) a cyano group, (h) a nitro group, (i) a C1-4 alkyl group optionally substituted by 1 to 3 halogen atoms, (j) a C1-4 alkyl-carbonylamino group optionally substituted by an amino group optionally substituted by a C1-4 alkoxy-carbonyl group, (k) a C1-4 alkylsulfonylamino group, and (l) a C6-40 arylsulfonylamino group optionally substituted by a C1-4 alkyl group,
- provided that partial structures:
- wherein * shows a binding position with a thiocarbonyl group, are not
- wherein * is as defined above,
- or an edible salt thereof,
- with a food or drink.
47 more elements
A food or drink having an enhanced salty taste, which comprises effective amounts of (A) a compound represented by formula (I):
- wherein:
- R1′ to R5′ are each independently:
- (i) a hydrogen atom,
- (ii) a hydroxyl group,
- (iii) a halogen atom,
- (iv) a carboxyl group,
- (v) a C1-4 alkoxy-carbonyl group,
- (vi) a C1-4 alkoxy group,
- (vii) an amino group optionally substituted by a C1-4 alkoxy-carbonyl group,
- (viii) a cyano group,
- (ix) a nitro group,
- (x) a C1-4 alkyl group optionally substituted by 1 to 3 halogen atoms,
- (xi) a C1-4 alkyl-carbonylamino group optionally substituted by an amino group optionally substituted by a C1-4 alkoxy-carbonyl group,
- (xii) a alkylsulfonylamino group, or
- (xiii) a C6-10 arylsulfonylamino group optionally substituted by a C1-4 alkyl group, or
- any two of R1′ to R5′ are optionally joined to form a C1-4 alkylenedioxy group,
- each R6′ is independently:
- (i) a hydrogen atom,
- (ii) a hydroxyl group,
- (iii) a C1-4 alkyl group optionally substituted by 1 to 3 substituents selected from a hydroxyl group, a C1-4 alkoxy group and a C7-14 aralkyloxy group,
- (iv) a C1-4 alkoxy group,
- (v) a carboxyl group,
- (vi) a C1-4 alkoxy-carbonyl group,
- (vii) a C6-10 aryl group, or
- (viii) a carbamoyl group, or
- R6′ and R5′ are optionally joined to form a C1-4 alkylene group,
- m is an integer of 0 to 2,
- Ra′ is a hydrogen atom, a hydroxyl group, a C1-4 alkyl group or a C7-14 aralkyl group, or
- Ra′ and R5′ are optionally joined to form a C1-4 alkylene group,
- Rb′ is a hydrogen atom, a hydroxyl group, a C1-4 alkyl group or a C7-14 aralkyl group, or
- Rb′ and R6′ are optionally joined to form a carbonyl group,
- p is 0 or 1,
- U is a single bond, —NH—CH2—, —N═CR12′—, wherein R12′ is a hydrogen atom or a C1-4 alkyl group, or U is a group represented by the following formula:
- wherein:
- each Rc′ is independently:
- (i) a hydrogen atom,
- (ii) a hydroxyl group,
- (iii) a C1-4 alkyl group optionally substituted by 1 to 3 substituents selected from a hydroxyl group, a C1-4 alkoxy group and a C7-14 aralkyloxy group,
- (iv) a C1-4 alkoxy group,
- (v) a carboxyl group,
- (vi) a C1-4 alkoxy-carbonyl group,
- (vii) a C6-10 aryl group, or
- (viii) a carbamoyl group, and
- q is an integer of 1 to 3, and
- E is a hydroxyl group, an amino group, a carbamoyl group, or E is a C3-10 cycloalkyl group, a C6-14 aryl group, or an aromatic heterocyclic group, each of which is optionally substituted by 1 to 3 substituents selected from the group consisting of (a) a hydroxyl group, (b) a halogen atom, (c) a carboxyl group, (d) a C1-4 alkoxy-carbonyl group, (e) a C1-4 alkoxy group, (f) an amino group optionally substituted by a C1-4 alkoxy-carbonyl group, (g) a cyano group, (h) a nitro group, (i) a C1-4 alkyl group optionally substituted by 1 to 3 halogen atoms, (j) a C1-4 alkyl-carbonylamino group optionally substituted by an amino group optionally substituted by a C1-4 alkoxy-carbonyl group, (k) a C1-4 alkylsulfonylamino group, and (l) a C6-10 arylsulfonylamino group optionally substituted by a C1-4 alkyl group,
- provided that partial structures:
- wherein * shows a binding position with a thiocarbonyl group, are not
- wherein * is as defined above,
- or an edible salt thereof;
- and
- (B) potassium chloride.
48 more elements
A compound represented by formula (II-1):
- wherein:
- R1 to R5 are each independently a hydrogen atom, a hydroxyl group, a C1-4 alkoxy group, a halogen atom, or an amino group, R6 is:
- (i) a hydrogen atom,
- (ii) a C1-4 alkyl group optionally substituted by a hydroxyl group or a C1-4 alkoxy group,
- (iii) a carboxyl group, or
- (vi) a C1-4 alkoxy-carbonyl group,
- Ra and Rb are each independently a hydrogen atom, a hydroxyl group, or a methyl group,
- Rc is:
- (i) a hydrogen atom,
- (ii) a carboxyl group,
- (iii) a C1-4 alkyl group optionally substituted by a hydroxyl group or a C1-4 alkoxy group, or
- (iv) a C1-4 alkoxy-carbonyl group;
- Rd is:
- (i) a hydrogen atom,
- (ii) a hydroxyl group, or
- (iii) a C1-4 alkyl group optionally substituted by a hydroxyl group or a C1-4 alkoxy group;
- R7 to R11 are each independently a hydrogen atom, a hydroxyl group, a carboxyl group, a halogen atom, a C1-4 alkyl group, or a C1-4 alkoxy group;
- and
- n is 0 or 1,
- provided that
- (1) when n is 0, then at least two of R1 to R5 are each a hydroxyl group,
- (2) when n is 1 and R6 is an unsubstituted C1-4 alkyl group, then at least one of R1 to R5 and R7 to R11 is a hydroxyl group, and
- (3) when n is 1, R6 is a hydrogen atom, Ra is a hydrogen atom or a methyl group, Rc is (i) a hydrogen atom, (ii) a carboxyl group, (iii) a C1-4 alkyl group optionally substituted by a C1-4 alkoxy group, or (iv) a C1-4 alkoxy-carbonyl group, and
- Rd is (i) a hydrogen atom, or (ii) a C1-4 alkyl group optionally substituted by a hydroxyl group, then
- (i) at least one of R1 to R5 is a hydroxyl group,
- (ii) when R3 is a hydroxyl group and R4 is a hydrogen atom, then R2 is not a methoxy group,
- (iii) R9 is not a halogen atom or a methoxy group, and
- (iv) when Rb is a methyl group, then Rd is not a hydroxyl group,
- or an edible salt thereof.
26 more elements
A compound represented by formula (II-2):
- wherein:
- R1 is a hydrogen atom, a hydroxyl group, a carboxyl group, or a C1-4 alkoxy-carbonyl group,
- R2 to R5 are each independently a hydrogen atom, a hydroxyl group, a C1-4 alkoxy group, or an amino group,
- Ra and Rb are each independently a hydrogen atom, a hydroxyl group, or a C1-4 alkyl group,
- Rc and Rd are each independently a hydrogen atom or a C1-4 alkyl group,
- R7 to R11 are each independently a hydrogen atom, a hydroxyl group, a carboxyl group, a halogen atom, a C1-4 alkyl group, or a C1-4 alkoxy group, and
- n is 0 or 1,
- provided that
- (1) when n is 0, then
- (i) R1 is a hydroxyl group or a carboxyl group, and Rc is a C1-4 alkyl group, or
- (ii) at least two of R1 to R5 are each a hydroxyl group, and
- (2) when n is 1, then
- (i) at least two of R1 to R5 are each a hydroxyl group, or
- (ii) when R1 is a carboxyl group or a C1-4 alkoxy-carbonyl group, then (a) Rb is a C1-4 alkyl group, and (b) at least one of R2 to R5 and R7 to R11 is a hydroxyl group, or an edible salt thereof.
11 more elements
A compound represented by formula (II-3):
- wherein:
- R1 to R5 are each independently a hydrogen atom, a hydroxyl group, a C1-4 alkoxy group, or an amino group,
- R6 is a C1-4 alkyl group,
- Ra and Rb are each independently a hydrogen atom, a hydroxyl group, or a C1-4 alkyl group,
- T is —NH—CH2— or —N═CR12—, wherein R12 is a hydrogen atom or a C1-4 alkyl group, and
- R7 to R11 are each independently a hydrogen atom, a hydroxyl group, a carboxyl group, a halogen atom, a C1-4 alkyl group, a C1-4 alkoxy group, or a C1-4 alkoxy-carbonyl group,
- provided that
- (1) at least one of R7 to R11 is not a hydrogen atom, and
- (2) when T is —N═CH— and R7 is a hydroxyl group, then R1′ is not a hydrogen atom,
- or an edible salt thereof.
7 more elements
A compound represented by formula (II-4):
- wherein:
- R1 to R5 are each independently a hydrogen atom, a hydroxyl group, a halogen atom, a carboxyl group, a C1-4 alkyl group, a C1-4 alkoxy group, or a C1-4 alkoxy-carbonyl group,
- Rc is a hydrogen atom, a carboxyl group, a C1-4 alkyl group optionally substituted by 1 to 3 hydroxyl groups, or a C1-4 alkoxy-carbonyl group, and
- R13 to R17 are each independently a hydrogen atom, a hydroxyl group, a halogen atom, a C1-4 alkyl group, or a C1-4 alkoxy group, provided that
- (i) at least one of R1 to R5 is a hydroxyl group, or
- (ii) when R1 is a C1-4 alkoxy group, then R5 is not a hydrogen atom,
- or an edible salt thereof.
4 more elements
A compound or edible salt thereof, wherein said compound is selected from the group consisting of
- 1-(3,4-dihydroxybenzyl)-3-(2-phenylethyl)thiourea;
- N-(2-phenylethyl)-3,4-dihydro-6,7-dihydroxyisoquinoline-2(1H)-carbothioamide;
- 1-(3,4-dihydroxybenzyl)-1-methyl-3-(2-phenylethyl)thiourea;
- 1-(4-hydroxybenzyl)-3-(2-phenylethyl)thiourea;
- 1-(3-hydroxybenzyl)-3-(2-phenylethyl)thiourea;
- 1-(3,4-dihydroxybenzyl)-3-phenylthiourea;
- 1-(3,4-dihydroxybenzyl)-1-isobutyl-3-(2-phenylethyl)thiourea;
- 1-((S)-2-hydroxy-1-phenylethyl)-3-(2-phenylethyl)thiourea;
- 1-benzyl-3-[(R)-1-(hydroxymethyl)-2-phenylethyl]thiourea;
- 1-benzyl-3-(2-hydroxy-2-phenylethyl)thiourea;
- 1-benzyl-3-[(S)-1-(hydroxymethyl)-2-phenylethyl]thiourea;
- 1-[2-(2-hydroxyphenyl)ethyl]-3-benzylthiourea;
- 1-[2-(3-hydroxyphenyl)ethyl]-3-benzylthiourea;
- 1-benzyl-1-hydroxy-3-(2-phenylethyl)thiourea;
- 1-benzyl-3-((R)-2-hydroxy-2-phenylethyl)thiourea;
- 1-benzyl-3-((S)-2-hydroxy-2-phenylethyl)thiourea;
- 1-((S)-2-methoxy-1-phenylethyl)-3-(2-phenylethyl)thiourea;
- 1-benzyl-3-(2-methoxy-2-phenylethyl)thiourea;
- 1-(3-aminobenzyl)-3-(2-phenylethyl)thiourea;
- 1-[(3-[(2-aminoacetyl)amino]benzyl]-3-(2-phenylethyl)thiourea;
- 1-[2-(2-hydroxyphenyl)ethyl]-3-((R)-1-phenylethyl)thiourea;
- 1-[3-(mesylamino)benzyl]-3-(2-phenylethyl)thiourea;
- 1-[2-(2-hydroxyphenyl)ethyl]-3-((R)-2,3-dihydro-1H-inden-1-yl)thiourea;
- 1-[2-(2-hydroxyphenyl)ethyl]-3-[(R)-1-(3-hydroxyphenyl)ethyl]thiourea;
- 1-(2-hydroxybenzyl)-4-((R)-1-phenylethyl)thiosemicarbazide;
- 1-(2,6-dihydroxyphenyl)-3-((R)-1-phenylethyl)thiourea;
- 2-{(E)-[4-((R)-1-phenylethyl)thiosemicarbazido]methylidene}benzoic acid;
- 1-[2-(2-hydroxyphenyl)ethyl]-3-((R)-1-phenylpropyl)thiourea;
- 1-[2-(2-hydroxyphenyl)ethyl]-3-[(R)-1-(3,4-dimethoxyphenyl)ethyl]thiourea;
- (S)-2-[3-(2-phenylethyl)thioureido]-2-phenylacetic acid;
- (S)-2-{3-[2-(2-hydroxyphenyl)ethyl]thioureido}-2-phenylacetic acid;
- 1-[2-(2-hydroxyphenyl)ethyl]-3-[(R)-1-(3,4-dihydroxyphenyl)ethyl]thiourea;
- 1-[2-(2-hydroxyphenyl)-2-hydroxyethyl]-3-[(R)-1-(3-hydroxyphenyl)ethyl]thiourea;
- 2-{3-[(R)-1-(3-hydroxyphenyl)ethyl]thioureido}-3-(2-hydroxyphenyl)propanoic acid;
- (R)-2-{3-[(R)-1-(3-hydroxyphenyl)ethyl]thioureido}-3-phenylpropanoic acid;
- (S)-2-{3-[(R)-1-(3-hydroxyphenyl)ethyl]thioureido}-3-phenylpropanoic acid;
- (R)-2-{3-[(R)-1-(3-hydroxyphenyl)ethyl]thioureido}-3-(4-hydroxyphenyl)propanoic acid;
- (S)-2-{3-[(R)-1-(3-hydroxyphenyl)ethyl]thioureido}-3-(4-hydroxyphenyl)propanoic acid;
- 1-[2-(2,3-dihydroxyphenyl)-2-hydroxyethyl]-3-[(R)-1-(3-hydroxyphenyl)ethyl]thiourea;
- 1-[2-(2,5-dihydroxyphenyl)-2-hydroxyethyl]-3-[(R)-1-(3-hydroxyphenyl)ethyl]thiourea;
- 1-[2-(2-hydroxy-5-methylphenyl)-2-hydroxyethyl]-3-[(R)-1-(3-hydroxyphenyl)ethyl]thiourea;
- 1-[2-(2,4-dihydroxyphenyl)-2-hydroxyethyl]-3-[(R)-1-(3-hydroxyphenyl)ethyl]thiourea;
- 1-[2-(5-chloro-2-hydroxyphenyl)-2-hydroxyethyl]-3-[(R)-1-(3-hydroxyphenyl)ethyl]thiourea;
- 1-[2-(5-bromo-2-hydroxyphenyl)-2-hydroxyethyl]-3-[(R)-1-(3-hydroxyphenyl)ethyl]thiourea;
- 2-{3-(4-chlorophenyl)thioureido}benzoic acid;
- 2-{3-[(R)-1-(3-hydroxyphenyl)ethyl]thioureido}benzoic acid;
- 5-hydroxy-2-[3-methyl-3-(2-phenylethyl)thioureido]benzoic acid;
- methyl 2-{(3-methyl-3-[2-(2-hydroxyphenyl)ethyl]thioureido}benzoate;
- methyl 2-{3-methyl-3-[2-(2-hydroxyphenyl)ethyl]thioureido}-5-hydroxybenzoate;
- 2-{3-methyl-3-[2-(2-hydroxyphenyl)ethyl]thioureido}benzoic acid;
- 2-{3-methyl-3-[2-(2-hydroxyphenyl)ethyl]thioureido}-5-hydroxybenzoic acid;
- and
- 2-(2-{3-[(R)-1-(3-hydroxyphenyl)ethyl]thioureido}ethyl)benzoic acid;
- or an edible salt of said compound.
51 more elements
Dependencies are inferred from the claim text.