Smoking article

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)R3 and OR4;
• Y is selected from the group consisting of H, and ORa
• R1 is selected from the group consisting of CH3 and OH;
• R2 is selected from the group consisting of H and CH3;
• or R1 and R2 together form at least ═CH2 or ═O;
• R3 is selected from H;
• optionally substituted C1-4 alkyl;
• COR5;
• CO2R5;
• and NR6R7;
• wherein
• R4 is selected from the group consisting of optionally substituted C1-4 alkyl;
• COR5;
• CO2R5;
• or, where Y is ORa, R4 may be Rb and Ra and Rb together form an optionally substituted C2-4 alkylene group;
• or where R1 is not CH3, R4 may be H;
• R5 is selected from the group consisting of H;
• (CH2)tO(CH2)uOH where t and u are independently 1 to 4;
• C1-4 alkyl optionally substituted with ═O, alkoxy, OH, CO2H, CH3, CON(R8)2;
• and an optionally substituted 3-7-membered aliphatic heterocyclyl;
• R6 and R7 are independently selected from the group consisting of H;
• C1-4 alkyl optionally substituted with OH, CO2R8, or a 5-7-membered heteroaryl;
• C3-6 cycloalkyl;
• 5-7-membered heteroaryl;
• and phenyl which is optionally substituted with CH3, CN, CH2CN, CH2CONH2, OCH3, or OH;
• R8 is selected from H and C1-4 alkyl;
• and/or a compound or combination of compounds according to formula (II), racemates, enantiomers and salts thereof:
• wherein
• R1′ is selected from the group consisting of CH(R5′)2 and Ra′;
• R2′ is selected the group consisting of from CH(R5′)2 and Rb′, where Ra′ and Rb′ together with the carbon atom to which they are attached form an optionally substituted aliphatic 3-6-membered ring;
• R3′ is selected from the group consisting of H, CH(R5′)2, and C1-4 alkyl;
• R4′ is selected from C1-4 alkyl optionally substituted with OH, CO2R6′, or a 5-7-membered heteroaryl;
• CO2R6′;
• C3-6 cycloalkyl;
• 5-7-membered heteroaryl;
• and phenyl which is optionally substituted with CH3, CN, CH2CN, CH2CONH2, OCH3, or OH;
• R5′ is selected from the group consisting of H and C1-4 alkyl optionally substituted with OH;
• R6′ is selected from the group consisting of H and C1-4 alkyl.