Cooling sensation agent composition, sensory stimulation agent composition and use of the same

Abstract

Disclosed is a cooling sensation agent composition or sensory stimulation agent composition which contains at least one of diester compounds of dicarboxylic acid represented by the formula (1) wherein A represents CH 2 or CH═CH, n represents an integer of 0 to 4 when A is CH 2 , or 1 when A is CH═CH, B is an alcohol residue having 10 to 18 carbon atoms and containing a para-menthane skeleton, which may have a substituent, and C is an alcohol residue having 6 to 18 carbon atoms, which may have a substituent as well as a flavor or fragrance composition, a beverage, a food product, a perfume or cosmetic product, a toiletry product, daily utensil products or groceries, a fiber, a fiber product, clothes, clothing or a medicine, wherein the cooling sensation agent composition or the sensory stimulation agent composition is compounded.

1 . A cooling sensation agent composition comprising: at least one diester compound of dicarboxylic acid represented by the formula (1): 
       
         
           
           
               
               
           
         
         wherein, A represents CH 2  or CH═CH, n represents an integer of 0 to 4 when A is CH 2 , or 1 when A is CH═CH, B is an alcohol residue having 10 to 18 carbon atoms and containing a para-menthane skeleton, which may have a substituent, and C is an alcohol residue having 6 to 18 carbon atoms, which may have a substituent. 
       
     
     
         2 . The cooling sensation agent composition according to  claim 1 , wherein C in the formula (1) is an alcohol residue having a para-menthane skeleton, which may have a substituent. 
     
     
         3 . The cooling sensation agent composition according to  claim 2 , wherein B and C in the formula ( 1 ) are not the same residue. 
     
     
         4 . The cooling sensation agent composition according to  claim 1 , wherein the alcohol residue for B or B and C in the formula (1) having a para-menthane skeleton, which may have a substituent, is one selected from alcohol residues of 1-menthol, 1-isopulegol, 3-(1-menthoxy)propane-1,2-diol, 2-(1-menthoxy)ethan-1-ol, 3-(1-menthoxy)propan-1-ol, 2-methyl-3-(1-menthoxy)propane-1,2-diol and para-menthane-3,8-diol. 
     
     
         5 . The cooling sensation agent composition according to  claim 1 , wherein the diester compounds of dicarboxylic acid represented by the formula (1) have ClogP of 3.0 or more and the molecular weight of 250 to 600. 
     
     
         6 . The cooling sensation agent composition according to  claim 1 , which further comprises at least one kind of cooling sensation substances other than the compounds corresponding to the formula (1). 
     
     
         7 . The cooling sensation agent composition according to  claim 6 , wherein the cooling sensation substances other than the compounds corresponding to the formula (1) are menthol, menthone, camphor, pulegol, isopulegol, cineole, mint oil, peppermint oil, spearmint oil, eucalyptus oil, 3-(1-menthoxy)propane-1,2-diol, N-alkyl-p-menthane-3-carboxamide, 2-methyl-3-(1-menthoxy)propane-1,2-diol, p-menthane-3,8-diol, 2-(1-menthoxy)ethan-1-ol, 3-(1-menthoxy)propan-1-ol, 4-(1-menthoxy)butan-1-ol, menthyl 3-hydroxybutanoate, menthyl lactate, menthone glycerin ketal, N-methyl-2,2-isopropylmethyl-3-methylbutane amide and menthyl glyoxylate. 
     
     
         8 . A sensory stimulation agent composition which contains the cooling sensation agent composition according to  claim 1 . 
     
     
         9 . The sensory stimulation agent composition according to  claim 8 , which further comprises at least one kind of warming and pungent substances. 
     
     
         10 . The sensory stimulation agent composition according to  claim 9 , wherein the warming and pungent substances are vanillyl ethyl ether, vanillyl propyl ether, vanillin propylene glycol acetal, ethylvanillin propylene glycol acetal, capsaicin, gingerol, vanillyl butyl ether, 4-(1-menthoxymethyl)-2-(3′-rnethoxy-4′-hydroxy-phenyl)-1,3-dioxolane, pepper oil, pepperoleoresin, gingeroleoresin, nonylic acid vanillylamide, jamboo oleoresin, Zanthoxylum Piperitum Peel Extract, sanshool-I, sanshool-II, sanshoamide, black pepper extract, chavicine, piperine and spilanthol. 
     
     
         11 . A flavor composition, or a fragrance composition, or a beverage, or a food product, or a perfume, or a cosmetic product, or a toiletry product, or a fiber product, or clothing, or a medicine, which comprises the cooling sensation agent composition according to  claim 1 . 
     
     
         12 . A flavor composition, or a fragrance composition, or a beverage, or a food product, or a perfume, or a cosmetic product, or a toiletry product, or a fiber product, or clothing or a medicine, which comprises the sensory stimulation agent composition according to  claim 7 . 
     
     
         13 . A method for providing a long-lasting cooling sensation effect, the method comprising steps of:
 directly applying the fragrance composition, or the perfume or the cosmetic product, or the medicine, or the toiletry product according to  claim 11  onto a skin or a scalp;   applying the flavor composition, or the fragrance composition, or the perfume, or the cosmetic product, or the toiletry product, or the medicine according to  claim 11  a fiber product;   applying the fragrance composition, or the perfume according to  claim 11  to clothing; or   administering the medicine according to  claim 11  to an oral cavity.   
     
     
         14 . A method for providing a long-lasting cooling sensation effect, the method comprising steps of:
 directly applying the fragrance composition, or the perfume, or cosmetic product, or the medicine, or the toiletry product according to  claim 12  onto a skin or a scalp;   applying the flavor composition, or fragrance composition, the perfume or the cosmetic product, the toiletry product, or the medicine according to  claim 12  to a fiber product;   applying the fragrance composition, or the perfume according to  claim 12  to clothing; or   administering the medicine according to  claim 12  to an oral cavity.   
     
     
         15 . The flavor composition or the fragrance composition according to  claim 11 , wherein the content of the cooling sensation agent composition is 0.0001 to 90% by mass to the total mass of the composition. 
     
     
         16 . The flavor composition or the fragrance composition according to  claim 12 , wherein the content of the sensory stimulation agent composition is 0.0001 to 90% by mass to the total mass of the composition. 
     
     
         17 . The beverage, or the food product, or the perfume or the cosmetic product, or the toiletry product, or the fiber product, or the clothing or the medicine according to  claim 11 , wherein the content of the cooling sensation agent composition is 1×10 −7 % to 20% by mass. 
     
     
         18 . The beverage, or the food product, or the perfume or cosmetic product, or the toiletry product, or the fiber product, or the clothing, or the medicine according to  claim 12 , wherein the content of the sensory stimulation agent composition is 1×10 −7 % to 20% by mass. 
     
     
         19 . A cool refreshment processing method of a fiber product or clothing, the method comprising the step of:
 compounding the cooling sensation agent composition according to  claim 1  with the fiber product or the clothing.   
     
     
         20 . A cool refreshment processing method of a fiber product, or clothing, the method comprising the step of:
 compounding the sensory stimulation agent composition according to  claim 7  with the fiber product or the clothing.   
     
     
         21 . A method for producing a flavor composition, or a fragrance composition, or a beverage, or a food product, or a perfume, or a cosmetic product, or a toiletry product, or a fiber product, or clothing or a medicine, the method comprising the step of:
 compounding the flavor composition, or the fragrance composition, or the beverage, or the food product, or the perfume, or the cosmetic product, or the toiletry product, or the fiber product, of the clothing, or the medicine with the cooling sensation agent composition according to  claim 1 .   
     
     
         22 . A method for producing a flavor composition, or fragrance composition, or a beverage, or a food product, or a perfume or a cosmetic product, or a toiletry product, or a fiber product, or clothing, clothes, or a medicine, the method comprising the step of:
 compounding the flavor composition, or the fragrance composition, or the beverage, or the food product, or the perfume, or the cosmetic product, or the toiletry product, or the fiber product, of the clothing, or the medicine with the sensory stimulation agent composition according to  claim 7 .   
     
     
         23 . Diester compounds of dicarboxylic acid represented by the formula (1′): 
       
         
           
           
               
               
           
         
         wherein, A 1  represents CH 2 , n represents an integer of 0 to 4, B 1  is an alcohol residue of an alcohol having 10 to 18 carbon atoms and containing a para-menthane skeleton, which may have a substituent, and C 1  is an alcohol residue of an alcohol having 6 to 18 carbon atoms, which may have a substituent, however when Bi or C 1  is an alcohol residue of menthol, another is not a residue of menthol. 
       
     
     
         24 . The diester compounds of dicarboxylic acid according to 23, wherein C 1  in the formula (1′) is an alcohol residue of an alcohol having a para-menthane skeleton, which may have a substituent. 
     
     
         25 . The diester compounds of dicarboxylic acid according to  claim 23 , wherein B 1  and C 1  in the formula (1′) are not the same residue. 
     
     
         26 . The diester compounds of dicarboxylic acid according to  claim 23 , wherein the alcohol residue for B 1  or B 1  and C 1  in the formula (1′) having a para-menthane skeleton, which may have a substituent, is any one selected from alcohol residues of 1-menthol, 1-isopulegol, 3-(1-menthoxy) propane-1,2-diol, 2-(1-menthoxy)ethan-1-ol, 3-(1-menthoxy) propan-1-ol, 2-methyl-3-(1-menthoxy) propane-1,2-diol and para-menthane-3,8-diol.