Homovanillic ester, more particularly for achieving an impression of heat and/or spiciness

Abstract

Compounds of formula (I) and novel uses of compounds of formula (I), such as for flavour compositions. New preparations and new methods using compounds of formula (I).

1 . A composition comprising one or more compounds, or physiologically acceptable salts thereof, having a structure represented by formula (I): 
       
         
           
           
               
               
           
         
         wherein 
         (i) R 1  and R 2  represent, independently of each other, a hydrogen atom or an alkyl residue with 1-2 carbon atoms, and
 R 3  and R 4  represent, independently of each other, a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms, a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or a linear or branched alkenyl residue with 2 to 4 carbon atoms or an alkenylphenyl residue or a phenylalkenyl residue; 
 or 
 
         (ii) R 1  and R 3  along with the carbon atoms linking them form a cyclohexyl ring,
 R 2  represents a hydrogen atom or an alkyl residue with 1-2 carbon atoms, 
 R 4  represents a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms, a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or a linear or branched alkenyl residue with 2 to 4 carbon atoms or an alkenylphenyl residue or a phenylalkenyl residue, 
 wherein the compounds of formula (I) are one or several different compounds of formula and/or physiologically acceptable salts thereof, where the phenolic hydroxy group in formula (I) is deprotonated, respectively. 
 
       
     
     
         2 . The composition of  claim 1 , wherein the one or more compounds are:
 a flavouring and/or pungent substance that creates a warm and/or pungent effect, and/or   a flavouring for reducing or masking an unpleasant taste sensation,   
       and/or
 a flavouring for increasing a pleasant taste sensation. 
 
     
     
         3 . The composition of  claim 1 , wherein one, several or all of the compounds of formula (I), independently of each other, have:
 (i) R 1  and R 2  being, independently of each other, a hydrogen atom or methyl group,
 R 3  and R 4  being, independently of each other, a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms or a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or an alkenylphenyl residue or a phenylalkenyl residue; or 
   (ii) Formula (I) corresponds to the following formula (Ia)   
       
         
           
           
               
               
           
         
         
           R 2  being a hydrogen atom, 
           R 4  being 2-propyl. 
         
       
     
     
         4 . The composition of  claim 1 , wherein one, several or all of the one or more compounds of formula (I), independently of each other, have:
 R 1  and R 2  being a hydrogen atom, respectively,   R 3  being a hydrogen atom or a linear or branched alkyl residue with 1 to 4 carbon atoms or a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or an alkenylphenyl residue or a phenylalkenyl residue,   R 4  being a hydrogen atom.   
     
     
         5 . The composition of  claim 1 , wherein one or several or all the compounds of formula (I) is or are selected from the group consisting of:
 2-phenylethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (1)   
       
         
           
           
               
               
           
         
         [(E)-cinnamyl]-2-(4-hydroxy-3-methoxyphenyl) acetate (2) 
       
       
         
           
           
               
               
           
         
         1-ethylbutyl-2-(4-hydroxy-3-methoxyphenyl) acetate (3) 
       
       
         
           
           
               
               
           
         
         3-methylbut-2-enyl-2-(4-hydroxy-3-methoxyphenyl) acetate (4) 
       
       
         
           
           
               
               
           
         
         [(E)-hex-2-enyl]-2-(4-hydroxy-3-methoxyphenyl) acetate (5) 
       
       
         
           
           
               
               
           
         
         [(Z)-hex-3-enyl]-2-(4-hydroxy-3-methoxyphenyl) acetate (6) 
       
       
         
           
           
               
               
           
         
         isopropyl-2-(4-hydroxy-3-methoxy-phenyl) acetate (7) 
       
       
         
           
           
               
               
           
         
         sec-butyl-2-(4-hydroxy-3-methoxyphenyl) acetate (8) 
       
       
         
           
           
               
               
           
         
         isobutyl-2-(4-hydroxy-3-methoxy-phenyl) acetate (9) 
       
       
         
           
           
               
               
           
         
         1,1-dimethylpropyl 2-(4-hydroxy-3-methoxyphenyl) acetate (10) 
       
       
         
           
           
               
               
           
         
         isopentyl-2-(4-hydroxy-3-methoxyphenyl) acetate (11) 
       
       
         
           
           
               
               
           
         
         2-methylbutyl-2-(4-hydroxy-3-methoxyphenyl) acetate (12) 
       
       
         
           
           
               
               
           
         
         1-methylpentyl-2-(4-hydroxy-3-methoxyphenyl) acetate (13) 
       
       
         
           
           
               
               
           
         
         heptyl-2-(4-hydroxy-3-methoxyphenyl) acetate (14) 
       
       
         
           
           
               
               
           
         
         1-methylhexyl-2-(4-hydroxy-3-methoxyphenyl) acetate (15) 
       
       
         
           
           
               
               
           
         
         (2-isopropyl-5-methyl-cyclohexyl)-2-(4-hydroxy-3-methoxyphenyl) acetate (16) 
       
       
         
           
           
               
               
           
         
         ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) 
       
       
         
           
           
               
               
           
         
         propyl-2-(4-hydroxy-3-methoxyphenyl) acetate (18) 
       
       
         
           
           
               
               
           
         
         butyl-2-(4-hydroxy-3-methoxyphenyl) acetate (19) 
       
       
         
           
           
               
               
           
         
         pentyl-2-(4-hydroxy-3-methoxyphenyl) acetate (20) 
       
       
         
           
           
               
               
           
         
         hexyl-2-(4-hydroxy-3-methoxyphenyl) acetate (21) 
       
       
         
           
           
               
               
           
         
         3-phenylpropyl 2-(4-hydroxy-3-methoxyphenyl) acetate (22) 
       
       
         
           
           
               
               
           
         
         4-phenylbutyl 2-(4-hydroxy-3-methoxyphenyl) acetate (23) 
       
       
         
           
           
               
               
           
         
       
     
     
         6 . The composition of  claim 1  formulated in a pharmaceutical preparation, a preparation serving nutrition, oral hygiene, wherein the total quantity of the one or more compound(s) of formula (I), and/or salt(s) thereof in the preparation is sufficient to:
 (a) sensorially create a warming and/or pungent effect on the tongue or in the oral cavity when the preparation is used or consumed, and/or 
 (b) reduce or mask an unpleasant taste sensation, and/or 
 (c) increase a pleasant taste sensation. 
 
     
     
         7 . The composition of  claim 6 , wherein the total amount of the compound(s) of formula (I), and/or salt(s) thereof in the preparation is not sufficient to create a warm or pungent effect on the tongue or in the oral cavity, but is sufficient to mask or reduce an unpleasant taste sensation of an unpleasantly tasting substance or mixture of substances. 
     
     
         8 . A composition comprising one or more compounds in accordance with formula (I), or a physiologically acceptable salt thereof, wherein the phenolic hydroxy group in formula (I) is deprotonated, or a mixture comprising one or several different compounds of formula (I) and/or one or several physiologically acceptable salts thereof, wherein the phenolic hydroxy group in formula (I) is deprotonated, respectively, or a plurality of different compounds of formula (I) and/or physiologically acceptable salts thereof, wherein the phenolic hydroxy group in formula (I) is deprotonated, respectively, 
       
         
           
           
               
               
           
         
         wherein 
         (i) R 1  and R 2  represent, independently of each other, a hydrogen atom or an alkyl residue with 1-2 carbon atoms,
 R 3  and R 4  represent, independently of each other, a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms, a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or a linear or branched alkenyl residue with 2 to 4 carbon atoms or an alkenylphenyl residue or a phenylalkenyl residue, 
 or 
 
         (ii) R 1  and R 3  along with the carbon atoms linking them form a cyclohexyl ring, which optionally is substituted with an additional residue R 5 , wherein R 5  is an alkyl residue with 1-2 carbon atoms,
 R 2  represents a hydrogen atom or an alkyl residue with 1-2 carbon atoms, 
 R 4  represents a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms, a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or a linear or branched alkenyl residue with 2 to 4 carbon atoms or an alkenylphenyl residue or a phenylalkenyl residue, 
 
         wherein
 R 1 , R 2 , R 3  and R 4  do not all represent hydrogen atoms, 
 
         and
 in case R 1 , R 2  and R 4  represent hydrogen, R 3  neither represents a linear alkyl residue with 1, 2, 4 or 5 carbon atoms nor 2-propyl or phenyl, methylphenyl, 
 
         and
 in case R 2 , R 3  and R 4  represent hydrogen, R 1  does not represent a linear alkyl residue with 1 or 2 carbon atoms, 
 R 3  and R 4  do not represent methyl, if R 1  and R 2  represent hydrogen, 
 
         and
 R 1  and R 2  do not represent methyl, if R 3  and R 4  represent hydrogen. 
 
       
     
     
         9 . The composition of  claim 8 , wherein one or several or all of the one or more compounds of formula (I) in the mixture is or are selected from:
 [(E)-cinnamyl]-2-(4-hydroxy-3-methoxyphenyl) acetate (2)   
       
         
           
           
               
               
           
         
         1-ethylbutyl-2-(4-hydroxy-3-methoxyphenyl) acetate (3) 
       
       
         
           
           
               
               
           
         
         3-methylbut-2-enyl-2-(4-hydroxy-3-methoxyphenyl) acetate (4) 
       
       
         
           
           
               
               
           
         
         [(E)-hex-2-enyl]-2-(4-hydroxy-3-methoxyphenyl) acetate (5) 
       
       
         
           
           
               
               
           
         
         [(Z)-hex-3-enyl]-2-(4-hydroxy-3-methoxyphenyl) acetate (6) 
       
       
         
           
           
               
               
           
         
         1,1-dimethylpropyl 2-(4-hydroxy-3-methoxyphenyl) acetate (10) 
       
       
         
           
           
               
               
           
         
         2-methylbutyl-2-(4-hydroxy-3-methoxyphenyl) acetate (12) 
       
       
         
           
           
               
               
           
         
         1-methylpentyl-2-(4-hydroxy-3-methoxyphenyl) acetate (13) 
       
       
         
           
           
               
               
           
         
         1-methylhexyl-2-(4-hydroxy-3-methoxyphenyl) acetate (15) 
       
       
         
           
           
               
               
           
         
         (2-isopropyl-5-methyl-cyclohexyl)-2-(4-hydroxy-3-methoxyphenyl) acetate (16) 
       
       
         
           
           
               
               
           
         
       
       pentyl-2-(4-hydroxy-3-methoxyphenyl) acetate (20) 
       
         
           
           
               
               
           
         
         4-phenylbutyl 2-(4-hydroxy-3-methoxyphenyl) acetate (23) 
       
       
         
           
           
               
               
           
         
       
     
     
         10 . A flavour composition comprising the composition of  claim 1 , wherein
 the total quantity of the compound(s) of formula and/or salt(s) thereof, in the flavour composition is in the range of 100-100,000 mg/kg, based on the total weight of the flavour composition.   
     
     
         11 . The flavour composition of  claim 10 , additionally comprising one or several further flavours, which do not correspond to formula (I) selected from:
 a) warming or pungent substances;   b) substances perceivable as pungent or biting;   c) alkamides described as causing a tingling sensation;   d) substances with physiological cooling effect;   e) substances having astringent effect.   
     
     
         12 . The flavour composition of  claim 10 , additionally comprising one or several substances which do not correspond to formula (I), with an unpleasant, in particular, bitter taste, or an astringent, bitter, dry, dusty, floury, chalky and/or metallic touch, selected from:
 f) xanthin alkaloids, xanthines, caffeine, theobromine, theophylline and methylxanthine, alkaloids, quinine, brucine, strychnine, nicotine, phenolic glycosides, salicin, arbutin, flavonoid glycosides neohespereidin, hesperidin, naringin, quercitrin, rutin, hyperosid, quercetin 3-O-glucoside, myricetin-3-O-glycosides, chalcones or chalcone glycosides, phloridzine, phloridzinxyloside, hydrolyzable tannins, gallic or ellagic acid esters of carbohydrates, pentagalloyl glucose, tannic acids, non-hydrolyzable tannins, flavones, quercetin, taxifolin, myricetin, phenols, salicin, polyphenols, gamma-oryzanol, caffeic acid or esters thereof, chlorogenic acid and isomers, terpenoid bitter and tanning agents, limonoides, limonin or nomilin from citrus fruits, lupolones and humulones from hops, iridoids, secoiridoids, absinthin from wormwood, amarogentin from gentian, metallic salts, potassium, magnesium and calcium salts, potassium chloride, potassium gluconate, potassium carbonate, potassium sulphate, potassium lactate, potassium glutamate, potassium succinate, potassium malate, sodium sulphate, magnesium sulphate, aluminium salts, zinc salts, tin salts, iron (II) salts, iron (III) salts, chromium (II) picolinate), active pharmaceutical ingredients, fluoroquinolone antibiotics, paracetamol, aspirin, beta-lactam antibiotics, ambroxol, propylthiouracil [PROP], guaifenesin, vitamins, vitamin H, vitamins from the B-series, such as vitamin B1, B2, B6, B12, niacin, pantothenic acid, denatonium benzoate, sucralose octaacetate, iron salts, aluminium salts, zinc salts, urea, unsaturated fatty acids, especially unsaturated fatty acids in emulsions, amino acids with a bitter/astringent taste, leucine, isoleucine, valine, tryptophan, proline, histidine, tyrosine, lysine or phenylalanine and peptides or proteins with a bitter/astringent taste, peptides with an amino acid from the group of leucine, isoleucine, valine, tryptophan, proline or phenylalanine at the N- or C-terminus, saponins, soya saponins, isoflavonoids, genistein, daidzein, genistein, daidzin, their glycosides and acylated glycosides;   g) substances with a non-unpleasant primary taste, sweet, salty, spicy, sour and/or smell selected from the group of sweeteners or sugar substitutes, potassium salts, potassium chloride, potassium gluconate, potassium carbonate, potassium sulphate, potassium lactate, potassium glutamate, potassium succinate, potassium malate, aspartame, acesulfame K, neotame, superaspartame, saccharin, sucralose, tagatose, monellin, stevioside, rebaudiosides, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside X, rubusoside, hernandulcin, thaumatin, miculin, glycyrrhizin, glycyrrhetinic acid, balansin A or balansin B, or derivatives thereof, cyclamate or the pharmaceutically acceptable salts of the above-mentioned compounds.   
     
     
         13 . A pharmaceutical preparation, preparation serving nutrition, oral hygiene, comprising the favour composition of  claim 12  wherein,
 the total quantity of the one or more compound(s) in accordance with formula (I), and/or salt(s), thereof in the preparation is in the range of 0.1-1,000 mg/kg, based on the total weight of the preparation. 
 
     
     
         14 . A pharmaceutical preparation, preparation serving nutrition, oral hygiene of  claim 13 , additionally comprising
 one or several usual base materials, auxiliaries and additives in a quantity of 10-80% w/w, based on the total weight of the preparation,   and/or   water in a quantity of 5-80% w/w, based on the total weight of the preparation.   
     
     
         15 . A pharmaceutical preparation, preparation serving nutrition, oral hygiene of  claim 13 , wherein the total quantity of the compound(s) of formula (I), and/or salt(s), thereof in the preparation is sufficient to:
 (a) sensorially create a warming and/or pungent effect on the tongue or in the oral cavity when the preparation is used or consumed,
 and/or 
   (b) reduce or mask an unpleasant taste sensation,
 and/or 
   (c) increase a pleasant taste sensation.   
     
     
         16 . A method for producing a pharmaceutical preparation, a preparation serving nutrition, oral hygiene or pleasure, comprising:
 i) providing
 a mixture that includes the composition of  claim 8 ,
 wherein 
 the total quantity of compound(s) of formula (I) and/or salt(s) thereof is selected such that the total quantity in the preparation to be made is in the range of 0.1-1,000 mg/kg, based on the total weight of the preparation, 
 
   ii) providing of one or several further components of the preparation to be made, and   iii) contacting or mixing the further components provided in step ii) with the component(s) provided in step i) in a sensorially effective quantity.   
     
     
         17 . A method for imparting a warm and/or pungent effect, for reducing or masking an unpleasant taste sensation, and/or for increasing a pleasant taste sensation, the method comprising:
 adding a sufficient amount of one or more compounds of formula (I), or physiologically acceptable salt thereof, to a preparation that comes into contact with an oral cavity, wherein the compounds of formula (I) are represented by the following structure:   
       
         
           
           
               
               
           
         
         
           wherein 
         
         (i) R 1  and R 2  represent, independently of each other, a hydrogen atom or an alkyl residue with 1-2 carbon atoms, and
 R 3  and R 4  represent, independently of each other, a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms, a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or a linear or branched alkenyl residue with 2 to 4 carbon atoms or an alkenylphenyl residue or a phenylalkenyl residue; or 
 
         (ii) R 1  and R 3  along with the carbon atoms linking them form a cyclohexyl ring,
 R 2  represents a hydrogen atom or an alkyl residue with 1-2 carbon atoms, 
 R 4  represents a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms, a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or a linear or branched alkenyl residue with 2 to 4 carbon atoms or an alkenylphenyl residue or a phenylalkenyl residue, 
 wherein the one or more compounds in accordance with formula I being one or several different compounds of formula (I), and/or physiologically acceptable salts thereof, where the phenolic hydroxy group in formula (I) is deprotonated, respectively. 
 
       
     
     
         18 . The method of  claim 17 , wherein one or more of the compounds of formula (I), independently of each other, have R 1  and R 2  being, independently of each other, a hydrogen atom or methyl group, R 3  and R 4  being, independently of each other, a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms or a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or an alkenylphenyl residue or a phenylalkenyl residue. 
     
     
         19 . The method of  claim 17 , wherein one or more of the compounds of formula (I), independently of each other, are represented by the following structure for Formula (Ia) 
       
         
           
           
               
               
           
         
         wherein R 2  is a hydrogen atom and R 4  is 2-propyl. 
       
     
     
         20 . The method of  claim 17 , wherein one or more of the compounds of formula (I), independently of each other, have:
 R 1  and R 2  being a hydrogen atom, respectively,   R 3  being a hydrogen atom or a linear or branched alkyl residue with 1 to 4 carbon atoms or a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or an alkenylphenyl residue or a phenylalkenyl residue,   R 4  being a hydrogen atom.