Aryl-acrylic acid esters

Abstract

The acrylic acid esters of Formula I are useful for the delivery of organoleptic compounds, especially for flavors, fragrances, masking agents and antimicrobial compounds. They can also deliver fluorescent whitening agents.

1. A compound of Formula I 
       
         
           
           
               
               
           
         
       
       wherein
 A is selected from benzene and naphthalene rings; 
 R 1  is a saturated, unsaturated, straight, branched, alicyclic or an aromatic C 10 -C 30  hydrocarbon residue which can contain heteroatoms and can be substituted by an ionic substituent; 
 R 2  in 2- or 3-position is a hydrogen, a straight or branched C 1 -C 6  residue, an optionally substituted aromatic or an optionally substituted heterocyclic residue; 
 R 3  and R 4  are a hydrogen, a straight or branched C 1 -C 6  alkyl, a C 1 -C 6  alkoxy residue, a substituted or condensed heterocyclic residue, —OH, —NO 2 , —NH 2 , —N(C 1 -C 6  alkyl) 2 , —N(hydroxyalkyl) 2 , —NHCO 2 CH 3  or —NH(heterocycle), 
 wherein R 2 , R 3  and R 4  are the same or different; 
 X is an —OH or NHR 6 , wherein R 6  is a hydrogen, a saturated or unsaturated, straight or branched C 1 -C 20  hydrocarbon, or 
 an optionally substituted aromatic or heterocyclic residue; 
 and the acrylic double bond is of the E configuration. 
 
     
     
       2. A compound according to  claim 1  wherein R 1  is a saturated, unsaturated, straight or branched C 10 -C 30  hydrocarbon residue comprising one or more O atoms, N atoms, C(O) groups, alkoxy groups and mixtures thereof. 
     
     
       3. A compound according to  claim 1  wherein R 1  is a saturated, unsaturated, straight or branched C 10 -C 30  hydrocarbon residue substituted by an ionic substituent of Formula NR 5   3   + , wherein R 5  is a residue of a fatty acid or an alkyl group with 1 to 30 carbon atoms. 
     
     
       4. A compound according to  claim 1  wherein R 2  is a heterocyclic residue of Formula 
       
         
           
           
               
               
           
         
       
       
        
       
     
     
       5. A compound according to  claim 1  wherein at least one of R 3  and R 4  is a five membered heterocyclic residue comprising N atoms and/or O atoms. 
     
     
       6. A compound according to  claim 1  wherein at least one of R 3  and/or R 4  is a hydrogen, —N(C 1 -C 6  alkyl) 2 , —NH 2 , or a five membered heterocyclic residue, substituted by C 1 -C 6  aliphatic and/or aromatic substituents. 
     
     
       7. A compound according to  claim 1  wherein R 2  is hydrogen or methyl. 
     
     
       8. A compound according to  claim 1  wherein R 1  is a residue of an olfactory alcohol of Formula R 1 OH. 
     
     
       9. A compound according to  claim 1  wherein R 1  is a residue of the enol form of an olfactory aldehyde of Formula R 1 HO. 
     
     
       10. A compound according to  claim 1  wherein R 1  is a residue of the enol form of an olfactory ketone of Formula R 1 O. 
     
     
       11. A compound according to  claim 1  wherein R 1  is a substituted alkyl, an alkenyl or an arylalkyl residue carrying a 1-alkoxy, 1-aryloxy or 1-arylalkoxy residue. 
     
     
       12. A compound according to  claim 1  wherein a residue of Formula Ia: 
       
         
           
           
               
               
           
         
       
       is a precursor for a fragrant coumarin. 
     
     
       13. A compound according to  claim 1  wherein a residue of Formula Ia 
       
         
           
           
               
               
           
         
       
       is a precursor for a fluorescent whitening coumarin. 
     
     
       14. A compound according to  claim 12  wherein R 1  is a residue of an olfactory alcohol, an aldehyde or ketone and the residue of Formula Ia 
       
         
           
           
               
               
           
         
       
       is a precursor for a fragrant coumarin. 
     
     
       15. A method for preparing compositions products selected from laundry products, tobacco products, cosmetics and toiletries which provide upon activation organoleptic, antimicrobial or fluorescent whitening properties comprising the step of: incorporating into one of these compositions said products a compound of Formula I: 
       
         
           
           
               
               
           
         
       
       wherein
 A is selected from benzene and naphthalene rings; 
 R 1  is selected from: a C 10 -C 30  hydrocarbon residue which may be saturated, unsaturated, straight, branched, alicyclic or an aromatic C 10 -C 30  hydrocarbon residue and which can contain heteroatoms and can be substituted by an ionic substituent, or 
 R 1  is a residue selected from nonyl, 3,5,5-trimethyl-hexanyl, cis-6-nonenyl, 2,6-nonadien-1-yl, 2-phenyl-propyl, 3-phenyl-propyl, 2-(2-methylphenyl)-ethyl, cinnamyl, 2-ethoxy-4-formylphenyl, 4-isopropyl-cyclohexyl, 3,3,5-trimethyl-cyclohexyl, 2-cyclohexyl-propyl, and 2,6-dimethyl-heptan-2-yl; 
 R 2  in the 2- or 3-position is a hydrogen, a straight or branched C 1 -C 6  residue, an optionally substituted aromatic or an optionally substituted heterocyclic residue; 
 R 3  and R 4  are a hydrogen, a straight or branched C 1 -C 6  alkyl, a C 1 -C 6  alkoxy residue, a substituted or condensed heterocyclic residue, —OH, —NO 2 , —NH 2 , —N(C 1 -C 6  alkyl) 2 , —N (hydroxyalkyl) 2 , —NHCO 2 CH 3  or —NH (heterocycle); 
 wherein R 2 , R 3  and R 4  are the same or different; 
 X is an —OH or NHR 6 , wherein R 6  is a hydrogen, a saturated or unsaturated, straight or branched C 1 -C 20  hydrocarbon, or an optionally substituted aromatic or heterocyclic residue; and 
 the acrylic double bond is of the E configuration. 
 
     
     
       16. A method according to  claim 15  wherein the precursors are incorporated into laundry products. 
     
     
       17. A method according to  claim 15  wherein the precursors are incorporated into tobacco products. 
     
     
       18. A method according to  claim 15  wherein the precursors are incorporated into cosmetics and toiletries. 
     
     
       19. A compound of the formula 
       
         
           
           
               
               
           
         
         wherein the acrylic double bond is of the E configuration. 
       
     
     
       20. A method for preparing products selected from laundry products, tobacco products, cosmetics and toiletries which provide upon activation organoleptic, antimicrobial or fluorescent whitening properties comprising the step of:
 incorporating into said products a compound of Formula I:   
       
         
           
           
               
               
           
         
         wherein A is selected from benzene and naphthalene rings; 
         R 1  is selected from a C 10 -C 30  hydrocarbon residue which may be saturated, unsaturated, straight, branched, alicyclic or aromatic and which can contain heteroatoms and can be substituted by an ionic substituent, or 
         R 1  is a residue selected from: nonyl alcohol, 3,5,5-trimethyl-hexanol, cis-6-nonenol, 2,6-nonadien-1-ol, 2-phenyl-propanol, 3-phenyl-propanol, 2-(2-methylphenyl)-ethanol, cinnamic alcohol, ethyl vanillin, 4-isopropyl-cyclohexanol, 3,3,5-trimethyl-cyclohexanol, 2-cyclohexyl-propanol, and 2,6-dimethyl-heptan-2-ol; 
         R 2  in the 2- or 3-position is a hydrogen, a straight or branched C 1 -C 6  residue, an optionally substituted aromatic or an optionally substituted heterocyclic residue; 
         R 3  and R 4  are a hydrogen, a straight or branched C 1 -C 6  alkyl, a C 1 -C 6  alkoxy residue, a substituted or condensed heterocyclic residue —OH —NO 2 , —-NH 2 , —N(C 1 -C 6  alkyl) 2 , —N(hydroxyalkyl) 2 , —NHCO 2 CH 3  or —NH(heterocycle); 
         wherein R 2 , R 3  and R 4  are the same or different; 
         X is an —OH or NHR 6 , wherein R 6  is a hydrogen, a saturated or unsaturated, straight or branched C 1 -C 20  hydrocarbon, or an optionally substituted aromatic or heterocyclic residue; and 
         the acrylic double bond is of the E configuration. 
       
     
     
       21. A method for preparing products selected from laundry products, tobacco products, cosmetics and toiletries which provide upon activation organoleptic, antimicrobial or fluorescent whitening properties comprising the step of:
 incorporating into said products a compound of the formula:   
       
         
           
           
               
               
           
         
         wherein the acrylic double bond is of the E configuration.