Agent for inhibiting odor of pyrazine derivatives

Abstract

Provided is an agent for reducing odors of pyrazine derivatives based on an olfactory receptor antagonism. The agent for reducing odors of pyrazine derivatives includes at least one antagonist of olfactory receptor OR5K1 as an active ingredient.

What is claim is: 
     
         1 . A method of reducing an odor of a pyrazine derivative, wherein the method comprises coexisting an odor of a pyrazine derivative with at least one compound selected from the group consisting of the following compounds:
 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol;   5-methyl-2-(1-methylethyl)-phenol;   3,7-dimethyl-2,6-octadienal;   phenylethyl salicylate;   1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthalenyl)-ethanone;   isolongifolanone;   4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one (α-ionone);   4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one (β-ionone);   vetiverol;   7-acetyl-1,2,3,4,5,6,7,8-octahydro-1,1,6,7-tetramethyl-naphthalene;   α-amylcinnamic aldehyde;   α-methyl-4-(1-methylethyl)-benzenepropanal;   4-methyl-3-decen-5-ol;   1-(2-tert-butylcyclohexyloxy)-2-butanol;   2-methoxy-1-(phenylmethoxy)-4-(1-propenyl)-benzene;   α-methyl-β-(p-tert-butylphenyl)-propionaldehyde;   l(−)-menthol;   ω-6-hexadecenelactone;   2-(2-(4-methyl)-3-cyclohexen-1-yl)-propylcyclopentanone;   formaldehyde cyclododecyl ethyl acetal;   1-(2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulen-5-yl)-ethanone;   β-methyl naphthyl ketone;   cedryl acetate;   (5E)-3-methylcyclopenta-5-decen-1-one;   cinnamaldehyde;   4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone;   α-hexylcinnamic aldehyde;   2-phenylpropionaldehyde;   3,7-dimethyl-6-octenal;   dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan;   4,7,7-trimethyl-spirobicyclo[2.2.1]heptane-2,1-cyclopentan-3-one;   α-isomethyl ionone;   3,7-dimethyl-1-octanol;   cedryl methyl ether;   muscone;   2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol;   2-cyclohexylpropanal;   γ-undecalactone;   cyclopentadecanolide;   1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one;   2,4-dimethyl-3-cyclohexene-1-carboxyaldehyde;   2,4,6-trimethyl-3-cyclohexene-1-carboxyaldehyde;   3,5,6-trimethyl-3-cyclohexene-1-carboxyaldehyde;   6,10-dimethyl-3-oxa-9-undecenal;   dimethyl benzyl carbinyl acetate;   ethyl-(3aα,4α,7α,3aα)-octahydro-4,7-methano-3aH-indene-3a-carboxylate;   2-pentyl-3-methyl-2-cyclopenten-1-one;   phenylhexanol;   1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one;   6-tert-butyl-1,1-dimethylinden-4-yl methyl ketone;   cis-4-isopropylcyclohexylmethanol;   1-allyl-3-methoxy-4-hydroxybenzene;   (E)-3,7-dimethyl-2,6-octadien-1-ol;   4-tert-butyl-2,6-dimethyl-3,5-dinitroacetophenone;   1,4-dioxacycloheptadecane-5,17-dione;   hexyl salicylate; and   α-methyl-3,4-methylenedioxyhydrocinnamic aldehyde.   
     
     
         2 . The method according to  claim 1 , which comprises applying at least one compound to an individual in need of reduction of the odor of the pyrazine derivative, in the presence of the odor of the pyrazine derivative. 
     
     
         3 . The method according to  claim 2 , wherein the at least one compound inhibits responses of an olfactory receptor OR5K1. 
     
     
         4 . The method according to  claim 1 , wherein the pyrazine derivative is a compound represented by the following formula (I): 
       
         
           
           
               
               
           
         
         wherein R 1  represents methyl, ethyl, or acetyl; and R 2 , R 3 , and R 4  each independently represent hydrogen or methyl. 
       
     
     
         5 . The method according to  claim 4 , wherein at least one of R 1  to R 4  represents an alkyl group. 
     
     
         6 . The method according to  claim 4 , wherein the pyrazine derivative is selected from the group consisting of 2,6-dimethylpyrazine, 2,5-dimethylpyrazine, 2,3-dimethylpyrazine, 2,3,5-trimethylpyrazine, 2,3,5,6-tetramethylpyrazine, 2-monomethylpyrazine, 2-monoethylpyrazine, 2-ethyl-6-methylpyrazine, 3-methyl-2-acetylpyrazine, and 3,5-dimethyl-2-acetylpyrazine. 
     
     
         7 . The method according to  claim 1 , wherein the at least one compound is selected from the group consisting of the following compounds:
 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol;   5-methyl-2-(1-methylethyl)-phenol;   3,7-dimethyl-2,6-octadienal;   phenylethyl salicylate;   1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthalenyl)-ethanone;   isolongifolanone;   4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one (α-ionone);   4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one (β-ionone);   vetiverol;   7-acetyl-1,2,3,4,5,6,7,8-octahydro-1,1,6,7-tetramethyl-naphthalene;   α-amylcinnamic aldehyde;   α-methyl-4-(1-methylethyl)-benzenepropanal;   4-methyl-3-decen-5-ol; and   1-(2-tert-butylcyclohexyloxy)-2-butanol.   
     
     
         8 . The method according to  claim 1 , wherein the odor of the pyrazine derivative is an odor generated by reaction of a skin tanning agent with skin. 
     
     
         9 . A method of antagonizing responses of an olfactory receptor OR5K1, wherein the method includes applying, to an olfactory receptor OR5K1, at least one compound selected from the group consisting of the following compounds:
 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol;   5-methyl-2-(1-methylethyl)-phenol;   3,7-dimethyl-2,6-octadienal;   phenylethyl salicylate;   1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthalenyl)-ethanone;   isolongifolanone;   4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one (α-ionone);   4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one (β-ionone);   vetiverol;   7-acetyl-1,2,3,4,5,6,7,8-octahydro-1,1,6,7-tetramethyl-naphthalene;   α-amylcinnamic aldehyde;   α-methyl-4-(1-methylethyl)-benzenepropanal;   4-methyl-3-decen-5-ol;   1-(2-tert-butylcyclohexyloxy)-2-butanol;   2-methoxy-1-(phenylmethoxy)-4-(1-propenyl)-benzene;   α-methyl-β-(p-tert-butylphenyl)-propionaldehyde;   l(−)-menthol;   ω-6-hexadecenelactone;   2-(2-(4-methyl)-3-cyclohexen-1-yl)-propylcyclopentanone;   formaldehyde cyclododecyl ethyl acetal;   1-(2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulen-5-yl)-ethanone;   β-methyl naphthyl ketone;   cedryl acetate;   (5E)-3-methylcyclopenta-5-decen-1-one;   cinnamaldehyde;   4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone;   α-hexylcinnamic aldehyde;   2-phenylpropionaldehyde;   3,7-dimethyl-6-octenal;   dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan;   4,7,7-trimethyl-spirobicyclo[2.2.1]heptane-2,1-cyclopentan-3-one;   α-isomethyl ionone;   3,7-dimethyl-1-octanol;   cedryl methyl ether;   muscone;   2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol;   2-cyclohexylpropanal;   γ-undecalactone;   cyclopentadecanolide;   1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one;   2,4-dimethyl-3-cyclohexene-1-carboxyaldehyde;   2,4,6-trimethyl-3-cyclohexene-1-carboxyaldehyde;   3,5,6-trimethyl-3-cyclohexene-1-carboxyaldehyde;   6,10-dimethyl-3-oxa-9-undecenal;   dimethyl benzyl carbinyl acetate;   ethyl-(3aα,4α,7α,3aα)-octahydro-4,7-methano-3aH-indene-3a-carboxylate;   2-pentyl-3-methyl-2-cyclopenten-1-one;   phenylhexanol;   1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one;   6-tert-butyl-1,1-dimethylinden-4-yl methyl ketone;   cis-4-isopropylcyclohexylmethanol;   1-allyl-3-methoxy-4-hydroxybenzene;   (E)-3,7-dimethyl-2,6-octadien-1-ol;   4-tert-butyl-2,6-dimethyl-3,5-dinitroacetophenone;   1,4-dioxacycloheptadecane-5,17-dione;   hexyl salicylate; and   α-methyl-3,4-methylenedioxyhydrocinnamic aldehyde.