Back to results
US 2025/0066690 A1Published application
Spiro Compounds as Malodor Counteracting Ingredients
AssigneeFirmenich SA
InventorsHuey-Ling KAO, Stefan Alexander RUIDER, Steven WILLIAMS, Julien COULOMB
Life of this patent
Estimating the term…
Abstract
The various aspects presented herein relate to the perfumery industry. More particularly, the various aspects presented herein relate to malodor counteracting compositions and/or ingredients, methods for counteracting malodors, as well as to the perfumed articles or perfuming compositions comprising as an active ingredient, at least one compound selected from the group consisting of: a compound of Formula (I), a compound of Formula (II), a compound of Formula (III), a compound of Formula (IV), and mixtures thereof.
Claims25
A method,
- wherein the method reduces, prevents, or inhibits a subject's perception of malodor,
- wherein the method comprises contacting the subject with at least one compound selected from the group consisting of:
- (1RS,6RS,11RS)-2,2,9,11-tetramethylspiro[5.5]undec-8-en-1-yl acetate, (+−)-2,2,7,11-tetramethylspiro[5.5]undec-8-en-1-yl-acetate, (+−)-2,3,7,7-tetramethylspiro[4.5]dec-2-en-6-yl acetate, (+−)-2,3,7,7-tetramethylspiro[4.5]dec-6-yl acetate, 1,5,10,10-tetramethylspiro[5.5]undec-3-en-11-yl acetate, 2,3,9,9-tetramethylspiro[4.5]decan-10-yl) acetate, (5,10,10-trimethylspiro[5.5]undec-2-en-11-yl) formate, (3,5,10,10-tetramethylspiro[5.5]undec-2-en-11-yl) acetate, (2,3,9,9-tetramethylspiro[4.5]dec-2-en-10-yl) acetate, (9,9-dimethylspiro[4.5]dec-2-en-10-yl) acetate, 10-methoxy-9,9-dimethylspiro[4.5]dec-2-ene, 4,10,10,11-tetramethylspiro[5.5]undec-2-en-11-ol, 5,10,10,11-tetramethylspiro[5.5]undec-3-en-11-ol, a mixture of 4,10,10,11-tetramethylspiro[5.5]undec-2-en-11-ol and 5,10,10,11-tetramethylspiro[5.5]undec-3-en-11-ol, 2,4,8-trimethylspiro[5.5]undec-3-en-11-ol, 2,9,11-trimethylspiro[5.5]undec-9-en-5-ol, a mixture of 2,4,8-trimethylspiro[5.5]undec-3-en-11-ol and 2,9,11-trimethylspiro[5.5]undec-9-en-5-ol, 3-methyl-5-propan-2-ylspiro[5.5]undec-2-en-11-ol, 11-methylspiro[5.5]undecan-5-ol, 3,10,10-trimethylspiro[5.5]undec-3-en-11-ol, 4,10,10-trimethylspiro[5.5]undec-3-en-11-ol, a mixture of 3,10,10-trimethylspiro[5.5]undec-3-en-11-ol and 4,10,10-trimethylspiro[5.5]undec-3-en-11-ol, [2,2-dimethyl-1-(2,4,6-trimethylcyclohex-3-en-1-yl) propyl] acetate, [2,2-dimethyl-1-(2,4,6-trimethylcyclohexyl) propyl] acetate, (1RS)-2,2-dimethyl-1-[(1SR,2SR)-2-methylcyclohexyl] propyl acetate, 9,9-dimethylspiro[4.5]dec-2-en-10-ol, 2,3,9,9-tetramethylspiro[4.5]decan-10-ol, (2,2,3,3,9,9-hexamethylspiro[4.5]decan-10-yl) acetate, 9-methoxy-8,8-dimethylspiro[4.4] non-2-ene, (8,8-dimethylspiro[4.4] non-2-en-9-yl) acetate, 2,3,8,8-tetramethylspiro[4.4] non-2-en-9-one, 2,3,9,9-tetramethylspiro[4.5] dec-2-en-10-ol, 4-methoxy-3,3-dimethylspiro[4.4]nonane, (4,9,9-trimethylspiro[4.5]dec-2-en-10-yl) acetate, 2,4,9,9-tetramethylspiro[4.5]dec-2-en-10-ol, (2,3,9,9-tetramethylspiro[4.5]dec-2-en-10-yl) formate, (2,4,9,9-tetramethylspiro[4.5]dec-2-en-10-yl) acetate, (+−)-2,3-dimethylspiro[4.5] dec-2-en-6-yl acetate, (4˜ {S},5˜ {R},6˜ {S},11˜ {S})-4,11-dimethylspiro[5.5]undecan-5-ol, 9,9-dimethylspiro[4.5]dec-2-en-10-one, 2,3,9,9-tetramethylspiro[4.5]dec-2-en-10-one, 2,4,9,9-tetramethylspiro[4.5]dec-2-en-10-one, 1,1′,1′,5-tetramethyl-2′-methylidenespiro[6-oxabicyclo[3.1.0]hexane-3,3′-cyclohexane], 4,9,9-trimethylspiro[4.5]dec-2-en-10-one, 2,2-dimethyl-6,6-bis (2-methylprop-2-enyl) cyclohexan-1-one, 2,2-dimethyl-5,5-bis (2-methylprop-2-enyl) cyclopentan-1-one, 2-but-3-en-2-yl-6,6-dimethyl-2-prop-2-enylcyclohexan-1-one, 2,2-bis(2-methyl-2-propen-1-yl) cyclohexanone, a mixture of 2-but-3-en-2-yl-6,6-dimethyl-2-prop-2-enylcyclohexan-1-one and 2,2-bis(2-methyl-2-propen-1-yl) cyclohexanone, 2,2-dimethyl-1-(2-methylcyclohexyl) propan-1-ol, 2,2-dimethyl-1-(3-methylcyclohexyl) propan-1-ol, a mixture of 2,2-dimethyl-1-(2-methylcyclohexyl) propan-1-ol and 2,2-dimethyl-1-(3-methylcyclohexyl) propan-1-ol, 2,2-dimethyl-6,6-bis (2-methylprop-2-enyl) cyclohexan-1-ol, 1-methoxy-2,6-dimethyl-1-prop-2-enylcyclohexane, methyl 1-(3-methylbut-2-enyl) cyclohex-2-ene-1-carboxylate, methyl 1-(3-methylbut-2-enyl) cyclohex-3-ene-1-carboxylate, a mixture of methyl 1-(3-methylbut-2-enyl) cyclohex-2-ene-1-carboxylate and methyl 1-(3-methylbut-2-enyl) cyclohex-3-ene-1-carboxylate, 2,2-dimethyl-5,5-bis (2-methylprop-2-enyl) cyclopentan-1-ol, 1-(2,6-dimethylcyclohex-3-en-1-yl)-2,2-dimethylpropan-1-ol, and mixtures thereof,
- wherein the subject is contacted with the at least one compound in an amount sufficient to reduce, prevent, or inhibit the subject's perception of malodor.
1 more element
A method,
- wherein the method inhibits at least one butyric acid receptor in a subject in need thereof,
- wherein the method comprises contacting the subject with at least one compound selected from the group consisting of:
- (1RS,6RS,11RS)-2,2,9,11-tetramethylspiro[5.5]undec-8-en-1-yl acetate, (+−)-2,2,7,11-tetramethylspiro[5.5]undec-8-en-1-yl-acetate, (+−)-2,3,7,7-tetramethylspiro[4.5]dec-2-en-6-yl acetate, (+−)-2,3,7,7-tetramethylspiro[4.5]dec-6-yl acetate, 1,5,10,10-tetramethylspiro[5.5]undec-3-en-11-yl acetate, 2,3,9,9-tetramethylspiro[4.5]decan-10-yl) acetate, (5,10,10-trimethylspiro[5.5]undec-2-en-11-yl) formate, (3,5,10,10-tetramethylspiro[5.5]undec-2-en-11-yl) acetate, (2,3,9,9-tetramethylspiro[4.5]dec-2-en-10-yl) acetate, (9,9-dimethylspiro[4.5]dec-2-en-10-yl) acetate, 10-methoxy-9,9-dimethylspiro[4.5]dec-2-ene, 4,10,10,11-tetramethylspiro[5.5]undec-2-en-11-ol, 5,10,10,11-tetramethylspiro[5.5]undec-3-en-11-ol, a mixture of 4,10,10,11-tetramethylspiro[5.5]undec-2-en-11-ol and 5,10,10,11-tetramethylspiro[5.5]undec-3-en-11-ol, 2,4,8-trimethylspiro[5.5]undec-3-en-11-ol, 2,9,11-trimethylspiro[5.5]undec-9-en-5-ol, a mixture of 2,4,8-trimethylspiro[5.5]undec-3-en-11-ol and 2,9,11-trimethylspiro[5.5]undec-9-en-5-ol, 3-methyl-5-propan-2-ylspiro[5.5]undec-2-en-11-ol, 11-methylspiro[5.5]undecan-5-ol, 3,10,10-trimethylspiro[5.5]undec-3-en-11-ol, 4,10,10-trimethylspiro[5.5]undec-3-en-11-ol, a mixture of 3,10,10-trimethylspiro[5.5]undec-3-en-11-ol and 4,10,10-trimethylspiro[5.5]undec-3-en-11-ol, [2,2-dimethyl-1-(2,4,6-trimethylcyclohex-3-en-1-yl) propyl] acetate, [2,2-dimethyl-1-(2,4,6-trimethylcyclohexyl) propyl] acetate, (1RS)-2,2-dimethyl-1-[(1SR,2SR)-2-methylcyclohexyl] propyl acetate, 9,9-dimethylspiro[4.5]dec-2-en-10-ol, 2,3,9,9-tetramethylspiro[4.5]decan-10-ol, (2,2,3,3,9,9-hexamethylspiro[4.5]decan-10-yl) acetate, 9-methoxy-8,8-dimethylspiro[4.4] non-2-ene, (8,8-dimethylspiro[4.4] non-2-en-9-yl) acetate, 2,3,8,8-tetramethylspiro[4.4] non-2-en-9-one, 2,3,9,9-tetramethylspiro[4.5] dec-2-en-10-ol, 4-methoxy-3,3-dimethylspiro[4.4]nonane, (4,9,9-trimethylspiro[4.5]dec-2-en-10-yl) acetate, 2,4,9,9-tetramethylspiro[4.5]dec-2-en-10-ol, (2,3,9,9-tetramethylspiro[4.5]dec-2-en-10-yl) formate, (2,4,9,9-tetramethylspiro[4.5]dec-2-en-10-yl) acetate, (+−)-2,3-dimethylspiro[4.5] dec-2-en-6-yl acetate, (4˜ {S},5˜ {R},6˜ {S},11˜ {S})-4,11-dimethylspiro[5.5]undecan-5-ol, 9,9-dimethylspiro[4.5]dec-2-en-10-one, 2,3,9,9-tetramethylspiro[4.5]dec-2-en-10-one, 2,4,9,9-tetramethylspiro[4.5]dec-2-en-10-one, 1,1′,1′,5-tetramethyl-2′-methylidenespiro[6-oxabicyclo[3.1.0]hexane-3,3′-cyclohexane], 4,9,9-trimethylspiro[4.5]dec-2-en-10-one, 2,2-dimethyl-6,6-bis (2-methylprop-2-enyl) cyclohexan-1-one, 2,2-dimethyl-5,5-bis (2-methylprop-2-enyl) cyclopentan-1-one, 2-but-3-en-2-yl-6,6-dimethyl-2-prop-2-enylcyclohexan-1-one, 2,2-bis(2-methyl-2-propen-1-yl) cyclohexanone, a mixture of 2-but-3-en-2-yl-6,6-dimethyl-2-prop-2-enylcyclohexan-1-one and 2,2-bis(2-methyl-2-propen-1-yl) cyclohexanone, 2,2-dimethyl-1-(2-methylcyclohexyl) propan-1-ol, 2,2-dimethyl-1-(3-methylcyclohexyl) propan-1-ol, a mixture of 2,2-dimethyl-1-(2-methylcyclohexyl) propan-1-ol and 2,2-dimethyl-1-(3-methylcyclohexyl) propan-1-ol, 2,2-dimethyl-6,6-bis (2-methylprop-2-enyl) cyclohexan-1-ol, 1-methoxy-2,6-dimethyl-1-prop-2-enylcyclohexane, methyl 1-(3-methylbut-2-enyl) cyclohex-2-ene-1-carboxylate, methyl 1-(3-methylbut-2-enyl) cyclohex-3-ene-1-carboxylate, a mixture of methyl 1-(3-methylbut-2-enyl) cyclohex-2-ene-1-carboxylate and methyl 1-(3-methylbut-2-enyl) cyclohex-3-ene-1-carboxylate, 2,2-dimethyl-5,5-bis (2-methylprop-2-enyl) cyclopentan-1-ol, 1-(2,6-dimethylcyclohex-3-en-1-yl)-2,2-dimethylpropan-1-ol, and mixtures thereof,
- wherein the subject is contacted with the at least one compound in an amount sufficient to inhibit the at least one butyric acid receptor.
1 more element
A compound,
- wherein the compound has the structure:
- in a form of any one of the stereoisomers or as a mixture thereof wherein the index m represents 0 or 1;
- wherein the index n represents 1 or 2;
- wherein the dotted lines represent a single or a double bond;
- wherein R1 represents a hydrogen atom, a methyl group or a R6C(═O) group wherein R6 represents a hydrogen atom or a methyl, ethyl, propyl or isopropyl group;
- wherein R2, R3 and R4 represent, independently from each other, a hydrogen atom or a methyl group;
- wherein each R5 represent, independently from each other, a hydrogen atom or a C1-3 alkyl or alkenyl group;
- and wherein the compound of Formula (I) is an antagonist of a butyric acid olfactory receptor.
5 more elements
A compound,
- wherein the compound has the structure:
- in a form of any one of the stereoisomers or as a mixture thereof
- wherein the index m represents 0 or 1;
- wherein the index n represents 1 or 2;
- wherein the dotted lines represent a single or a double bond;
- wherein R1, and R2 represent, independently from each other, a hydrogen atom or a methyl group;
- wherein each R3 represent, independently from each other, a hydrogen atom or a C1-3 alkyl or alkenyl group;
- and
- wherein the compound of Formula (II) is an antagonist of a butyric acid olfactory receptor.
6 more elements
A compound,
- wherein the compound has the structure:
- in a form of any one of the stereoisomers or as a mixture thereof
- wherein the index m represents 0 or 1;
- wherein R1, and R2 represent, independently from each other, a hydrogen atom or a methyl group;
- wherein each R3 represent, independently from each other, a hydrogen atom or a C14 alkyl or alkenyl group;
- and
- wherein the compound of Formula (III) is an antagonist of a butyric acid olfactory receptor.
4 more elements
A compound,
- wherein the compound has the structure:
- in a form of any one of the stereoisomers or as a mixture thereof
- wherein the index m represents 0 or 1;
- wherein R1 represents a hydrogen atom, a methyl group or a R6C(═O) group wherein R6 represents a hydrogen atom or a methyl, ethyl, propyl or isopropyl group;
- wherein R2, R3 and R4 represent, independently from each other, a hydrogen atom, a methyl group, a C14 alkyl or alkenyl group;
- wherein each R5 represent, independently from each other, a hydrogen atom or a C14 alkyl or alkenyl group;
- and
- wherein the compound of Formula (IV) is an antagonist of a butyric acid olfactory receptor.
5 more elements
A perfuming composition comprising the compound of any one of the preceding claims.
A consumer product comprising the compound of any one of the preceding claims.
A method,
- wherein the method reduces, prevents, or inhibits a subject's perception of malodor,
- wherein the method comprises contacting the subject with at least one compound according to any one of the preceding claims,
- wherein the subject is contacted with the at least one compound in an amount sufficient to reduce, prevent, or inhibit the subject's perception of malodor.
A method,
- wherein the method inhibits at least one butyric acid receptor in a subject in need thereof,
- wherein the method comprises contacting the subject with at least one compound according to any one of the preceding claims,
- wherein the subject is contacted with the at least one compound in an amount sufficient to inhibit the at least one butyric acid receptor.
Dependencies are inferred from the claim text.