Carboxilic Acid Amides Provoking A Cooling Sensation
AssigneeGivaudan SA
InventorsChristophe C. Galopin, Stefan Michael Furrer, Lori W. Tigani, Jay Patrick Slack, Pablo Victor Krawec, Lucienne Cole
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Abstract
The present invention refers to cooling compounds of formula I wherein R1, R2, R3, X, Y, Z, and m have the same meaning as given in the specification. The present invention refers furthermore to a process for their production and to product compositions comprising them.
Claims16
A product selected from the group consisting of topical products, oral care products, nasal care products, toilet articles, ingestible products and chewing gum, comprising a product base and an effective amount of a cooling compound of formula I
- wherein X is (CH2)n—R, wherein R is a group comprising at least one free electron pair and n is 0 or 1;
- m is 0, 1, or 2;
- and
- Y and Z are independently selected from the group consisting of H, OH, C1 to C4 alkyl, and C1 to C4 alkoxy;
- or
- X and Y form together a bivalent radical selected from the group consisting of —O—CH2—O—, —N═CH—O— and —N═CH—S— forming together with the carbon atoms to which they are attached a 5-membered ring;
- and
- Z is selected from the group consisting of H, OH, C1 to C4 alkyl, and C1 to C4 alkoxy;
- R1 is 1H, or C1 to C4 alkyl;
- and
- R2 and R3 together with the carbon atom to which they are attached forms a 3 to 10 membered mono- or bicyclic carboxylic ring optionally substituted by an alkyl residue having up to 4 carbon atoms, and the ring may optionally comprise one or more oxygen atoms;
- with the proviso that R2 and R3 together with the carbon atom to which they are attached is not 2-isopropyl-5-methyl-cyclohexyl;
- or
- R1, R2 and R3 together with the carbon atom to which they are attached forms a 6 to 10 membered tricyclic carboxylic ring, optionally substituted by an alkyl residue having up to 4 carbon atoms, and the ring may optionally comprise one or more oxygen atoms.
A method of providing a cooling effect to the mouth or skin by applying thereto a product comprising a compound of formula I
- wherein X is (CH2)n—R, wherein R is a group comprising at least one free electron pair and n is 0 or 1;
- m is 0, 1 or 2;
- and
- Y and Z are independently selected from the group consisting of H, OH, C1 to C4 alkyl, and C1 to C4 alkoxy;
- or
- X and Y form together a bivalent radical selected from the group consisting of —O—CH2—O—, —N═CH—O— and —N═CH—S— forming together with the carbon atoms to which they are attached a 5-membered ring;
- and
- Z is selected from the group consisting of 14, OH, C1 to C4 alkyl, and C1 to C4 alkoxy;
- R1 is H, or C1 to C4 alkyl;
- and
- R2 and R3 together with the carbon atom to which they are attached forms a 3 to 10 membered mono- or bicyclic carboxylic ring optionally substituted by an alkyl residue having up to 4 carbon atoms, and the ring may optionally comprise one or more oxygen atoms;
- with the proviso that R2 and R3 together with the carbon atom to which they are attached is not 2-isopropyl-5-methyl-cyclohexyl;
- R1, R2 and R3 together with the carbon atom to which they are attached forms a 6 to 10 membered tricyclic carboxylic ring, optionally substituted by an alkyl residue having up to 4 carbon atoms, and the ring may optionally comprise one or more oxygen atoms.
(canceled)
A compound of formula I
- wherein X is (CH2)n—R, wherein R is a group comprising at least one free electron pair and n is 0 or 1;
- m is 0, 1, or 2;
- and
- Y and Z are independently selected from the group consisting of H, OH, C1 to C4 alkyl, and C1 to C4 alkoxy;
- or
- X and Y form together a bivalent radical selected from the group consisting of —O—CH2—O—, —N═CH—O— and —N═CH—S— forming together with the carbon atoms to which they are attached a 5-membered ring;
- and
- Z is selected from the group consisting of H, OH, C1 to C4 alkyl, and C1 to C4 alkoxy;
- R1 is H, or C1 to C4 alkyl;
- and
- R2 and R3 together with the carbon atom to which they are attached forms a 3 to 10 membered mono- or bicyclic carboxylic ring optionally substituted by an alkyl residue having up to 4 carbon atoms, and the ring may optionally comprise one or more oxygen atoms;
- with the proviso that R2 and R3 together with the carbon atom to which they are attached is not 2-isopropyl-5-methyl-cyclohexyl.
Dependencies are inferred from the claim text.