Smoking article

1. An aerosol-generating device comprising:

a smoking article comprising a smokable material, a cooling agent and method, wherein the cooling agent is impregnated into the smokable material, and the smokable material comprises a tobacco component; and

a heat source disposed to heat, but not burn the smokable material in use;

wherein the cooling agent comprises:

a compound or a combination of compounds according to formula (I), racemates, enantiomers and salts thereof:

wherein

X is selected from the group consisting of C(═O)R 3 and OR 4 ;

Y is selected from the group consisting of H, and OR a

R 1 is selected from the group consisting of CH 3 and OH;

R 2 is selected from the group consisting of H and CH 3 ;

or R 1 and R 2 together form at least ═CH 2 or ═O;

R 3 is selected from H; optionally substituted C 1-4 alkyl; COR 5 ; CO 2 R 5 ; and NR 6 R 7 ;

wherein

R 4 is selected from the group consisting of optionally substituted C 1-4 alkyl; COR 5 ; CO 2 R 5 ;

or, where Y is OR a , R 4 may be R b and R a and R b together form an optionally substituted C 2-4 alkylene group; or where R 1 is not CH 3 , R 4 may be H;

R 5 is selected from the group consisting of H; (CH 2 ) t O(CH 2 ) u OH where t and u are independently 1 to 4; C 1-4 alkyl optionally substituted with ═O, alkoxy, OH, CO 2 H, CH 3 , CON(R 8 ) 2 ; and an optionally substituted 3-7-membered aliphatic heterocyclyl;

R 6 and R 7 are independently selected from the group consisting of H; C 1-4 alkyl optionally substituted with OH, CO 2 R 8 , or a 5-7-membered heteroaryl; C 3-6 cycloalkyl; 5-7-membered heteroaryl; and phenyl which is optionally substituted with CH 3 , CN, CH 2 CN, CH 2 CONH 2 , OCH 3 , or OH;

R 8 is selected from H and C 1-4 alkyl;

and/or a compound or combination of compounds according to formula (II), racemates, enantiomers and salts thereof:

wherein

R 1 ′ is selected from the group consisting of CH(R 5 ′) 2 and R a ′;

R 2 ′ is selected the group consisting of from CH(R 5 ′) 2 and R b ′, where R a ′ and R b ′ together with the carbon atom to which they are attached form an optionally substituted aliphatic 3-6-membered ring;

R 3 ′ is selected from the group consisting of H, CH(R 5 ′) 2 , and C 1-4 alkyl;

R 4 ′ is selected from C 1-4 alkyl optionally substituted with OH, CO 2 R 6 ′, or a 5-7-membered heteroaryl; CO 2 R 6 ′; C 3-6 cycloalkyl; 5-7-membered heteroaryl; and phenyl which is optionally substituted with CH 3 , CN, CH 2 CN, CH 2 CONH 2 , OCH 3 , or OH;

R 5 ′ is selected from the group consisting of H and C 1-4 alkyl optionally substituted with OH;

R 6 ′ is selected from the group consisting of H and C 1-4 alkyl.

2. An aerosol-generating device according to claim 1 , wherein the cooling agent comprises a compound or a combination of compounds according to formula (Ia), racemates, enantiomers and salts thereof:

wherein

R 2 ′ is selected from CH(R 5 ′) 2 and R b ′, where R a ′ and R b ′ together with the carbon atom to which they are attached form 2-isopropyl-5-methylcyclohexylene;

R 3 ′ is selected from H and CH(R 5 ′) 2 ; and

R 5 ′ is selected from H and CH 3 .

3. An aerosol-generating device according to claim 1 , wherein the cooling agent has a vapor pressure of less than about 106 Pa at 20° C.

4. An aerosol-generating device according to claim 1 , wherein the menthol is disposed in the smokable material.

5. An aerosol-generating device according to claim 1 , further comprising a filter.

6. An aerosol-generating device according to claim 5 , wherein menthol is disposed in the filter.

7. An aerosol-generating device according to claim 5 , wherein menthol is disposed in the smokable material and in the filter.

8. An aerosol-generating device according to claim 1 , wherein the weight ratio of cooling agent to menthol in the smoking article is from about 1:150 to about 1:1.

9. An aerosol-generating device according to claim 1 , wherein the cooling agent is selected from the group consisting of:

or combinations thereof.

10. An aerosol-generating device according to claim 1 , wherein the cooling agent is selected from the group consisting of:

1 N-ethyl-2-isopropyl-5-methylcyclohexane carboxamide;

2-isopropyl-N-[(ethoxycarbonyl)methyl]-5-methylcyclohexanecarboxamide;

2-isopropyl-N-(4-methoxylphenyl)-5-methylcyclohexanecarboxamide;

2-isopropyl-N,2,3-trimethylbutanamide;

or combinations thereof.

11. A smoking article for use in an aerosol generating device, the smoking article comprising a smokable material, a cooling agent and method, wherein the cooling agent is impregnated into the smokable material, and the smokable material comprises a tobacco component; and wherein the cooling agent is as defined in claim 1 .

12. A smoking article according to claim 11 ;

wherein the smokable material comprises a tobacco component in an amount of from 60 to 90% by weight of the smokable material, a filler in an amount of 0 to 20% by weight of the smokable material, and an aerosol generating agent in an amount of from 10 to 20% by weight of the tobacco composition,

wherein the tobacco composition has a nicotine content of from 0.5 to 2.5% by weight of the tobacco composition; and

wherein the tobacco component comprises paper reconstituted tobacco in an amount of from 70 to 100% by weight of the tobacco component.

13. A method of manufacturing a smoking article for use with an aerosol-generating device, the method comprising:

impregnating a cooling agent into a smokable material comprising a tobacco component, wherein the cooling agent is as defined in claim 1 ;

applying menthol to the tobacco component; and

combining the smokable material with a filter to provide a smoking article.