Cooling compositions including menthyl esters

Abstract

This description provides cooling compositions that deliver a prolonged physiological cooling sensation to the skin or a mucous membrane. The cooling compositions may be present alone or in product such as a chewing gum or a confection. In some embodiments, the cooling compositions include menthyl glutarate and at least one additional cooling agent, which may be WS-3 or WS-23, and optionally menthol. The cooling compositions may be in a liquid form at room temperature.

1 . A cooling composition consisting essentially of: 
 about 5% to about 60% by weight menthyl glutarate;    about 5% to about 50% by weight of at least one cooling agent selected from the group consisting of N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide and combinations thereof; and    about 15% to about 85% by weight menthol.    
     
     
         2 . The cooling composition of  claim 1 , wherein said menthyl glutarate is selected from the group consisting of monomenthyl monomenthyl 2-methylmaleatementhyl glutarate (FEMA 4006), monomenthyl glutarate ester, dimenthyl glutarate ester, and a menthyl half acid ester derivative.  
     
     
         3 . A chewing gum composition comprising the cooling composition of  claim 1 .  
     
     
         4 . A confectionery composition comprising the cooling composition of  claim 1 .  
     
     
         5 . A cooling composition consisting essentially of: 
 about 5% to about 60% by weight of at least two menthyl esters;    about 5% to about 50% by weight of at least one cooling agent selected from the group consisting of N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide and combinations thereof; and    about 15% to about 85% by weight menthol.    
     
     
         6 . The cooling composition of  claim 5 , wherein said at least two menthyl esters are selected from the group consisting of monomenthyl monomenthyl 2-methylmaleatementhyl glutarate (FEMA 4006), monomenthyl glutarate ester, dimenthyl glutarate ester, a menthyl half acid ester derivative, menthyl acetate, 1-menthyl acetate, d,1-menthyl acetate, homomenthyl acetate, menthyl lactate, 1-menthyl lactate, menthyl succinate, monomenthyl succinate, and combinations thereof.  
     
     
         7 . A chewing gum composition comprising the cooling composition of  claim 5 .  
     
     
         8 . A confectionery composition comprising the cooling composition of  claim 5 .  
     
     
         9 . A cooling composition comprising: 
 about 5% to about 60% by weight menthyl glutarate;    about 5% to about 50% by weight of at least one cooling agent selected from the group consisting of N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide and combinations thereof; and    at least about 75% by weight of the menthyl glutarate and the at least one cooling agent,    wherein said composition is liquid at 25° C.    
     
     
         10 . The cooling composition of  claim 9 , further comprising menthol in amounts of about 15% to about 85% by weight of the composition.  
     
     
         11 . The cooling composition of  claim 9 , wherein said menthyl glutarate is selected from the group consisting monomenthyl 2-methylmaleatementhyl glutarate (FEMA 4006), monomenthyl glutarate ester, dimenthyl glutarate ester, and a menthyl half acid ester derivative.  
     
     
         12 . A chewing gum composition comprising the cooling composition of  claim 9 .  
     
     
         13 . A confectionery composition comprising the cooling composition of  claim 9 .  
     
     
         14 . A cooling composition comprising: 
 about 5% to about 60% by weight of at least two menthyl esters;    about 5% to about 50% by weight of at least one cooling agent selected from the group consisting of N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide and combinations thereof; and    at least about 75% by weight of the at least two menthyl esters and the at least one cooling agent,    wherein said composition is liquid at 25° C.    
     
     
         15 . The cooling composition of  claim 14 , further comprising menthol in amounts of about 15% to about 85% by weight of the composition.  
     
     
         16 . The cooling composition of  claim 14 , wherein said at least two menthyl esters are selected from the group consisting of monomenthyl monomenthyl 2-methylmaleatementhyl glutarate (FEMA 4006), monomenthyl glutarate ester, dimenthyl glutarate ester, a menthyl half acid ester derivative, menthyl acetate, 1-menthyl acetate, d,1-menthyl acetate, homomenthyl acetate, menthyl lactate, 1-menthyl lactate, menthyl succinate, monomenthyl succinate, and combinations thereof.  
     
     
         17 . A chewing gum composition comprising the cooling composition of  claim 14 .  
     
     
         18 . A confectionery composition comprising the cooling composition of  claim 14 .  
     
     
         19 . A cooling composition consisting essentially of: 
 about 5% to about 60% by weight menthyl glutarate;    about 5% to about 50% by weight of at least one cooling agent selected from the group consisting of N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide and combinations thereof; and    about 15% to about 85% by weight menthol,    wherein said composition is liquid at 25° C.    
     
     
         20 . The cooling composition of  claim 19 , wherein said menthyl glutarate is selected from the group consisting of monomenthyl monomenthyl 2-methylmaleatementhyl glutarate (FEMA 4006), monomenthyl glutarate ester, dimenthyl glutarate ester, and a menthyl half acid ester derivative.  
     
     
         21 . A chewing gum composition comprising the cooling composition of  claim 19 .  
     
     
         22 . A confectionery composition comprising the cooling composition of  claim 19 .  
     
     
         23 . A cooling composition consisting essentially of: 
 about 5% to about 60% by weight of at least two menthyl esters;    about 5% to about 50% by weight of at least one cooling agent selected from the group consisting of N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide and combinations thereof; and    about 15% to about 85% by weight menthol,    wherein said composition is liquid at 25° C.    
     
     
         24 . The cooling composition of  claim 23 , wherein said at least two menthyl esters are selected from the group consisting of monomenthyl monomenthyl 2-methylmaleatementhyl glutarate (FEMA 4006), monomenthyl glutarate ester, dimenthyl glutarate ester, a menthyl half acid ester derivative, menthyl acetate, 1-menthyl acetate, d,1-menthyl acetate, homomenthyl acetate, menthyl lactate, 1-menthyl lactate, menthyl succinate, monomenthyl succinate, and combinations thereof.  
     
     
         25 . A chewing gum composition comprising the cooling composition of  claim 23 .  
     
     
         26 . A confectionery composition comprising the cooling composition of  claim 23 .  
     
     
         27 . A cooling composition comprising: 
 menthyl succinate;    a second cooling agent selected from the group consisting of N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide and combinations thereof; and    a third cooling agent selected from the group consisting of 1-isopulegol, p-menthane-3,8-diol and combinations thereof.    
     
     
         28 . The cooling composition of  claim 27 , wherein said menthyl succinate is selected from the group consisting of monomenthyl succinate, dimenthyl succinate and monomenthyl α,α-dimethyl succinate.  
     
     
         29 . A chewing gum composition comprising the cooling composition of  claim 27 .  
     
     
         30 . A confectionery composition comprising the cooling composition of  claim 27 .  
     
     
         31 . A method of preparing a cooling composition which is liquid at 25° C., comprising the steps of: 
 (a) providing menthyl glutarate in a liquid form; and    (b) adding at least one cooling agent selected from the group consisting of N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide and combinations thereof to the menthyl glutarate and dissolving or suspending the at least one cooling agent therein to form the liquid cooling composition,    wherein the menthyl glutarate is present in amounts of about 5% to about 60% by weight of the composition and the at least one cooling agent selected from the group consisting of N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide and combinations thereof is present in amounts of about 5% to about 50% by weight of the composition.    
     
     
         32 . The method of  claim 31 , further comprising the step of adding menthol in amounts of about 15% to about 85% by weight of the cooling composition.  
     
     
         33 . A method of preparing a cooling composition which is liquid at 25° C., comprising the steps of: 
 (a) combining menthyl glutarate and at least one cooling agent selected from the group consisting of N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide and combinations thereof;    (b) heating the menthyl glutarate and the at least one cooling agent to form a liquid composition; and    (c) cooling the composition of the menthyl glutarate and the at least one cooling agent to less than 30° C. while maintaining the composition in a liquid state to form the liquid cooling composition.