USRE49502EActiveUtility

Phenyl based compounds substituted with aldehyde moieties and their use in perfumery

57
Assignee: GIVAUDAN SAPriority: Nov 10, 2014Filed: Oct 9, 2015Granted: Apr 25, 2023
Est. expiryNov 10, 2034(~8.3 yrs left)· nominal 20-yr term from priority
Inventors:Corinne BaumgartnerYue Zou
C11D 3/50C11B 9/0061C07C 47/228C11B 9/0034
57
PatentIndex Score
0
Cited by
50
References
37
Claims

Abstract

A compound represented by the formula 1whereinR1 is H, or when R2 and R3 is H, then R1 is CHR5CHR6CHO, CR5═CR6CHO or C(CH3)CHO, wherein R5, R6 each independently may represent H or methyl;R2 is H, or when R1 and R3 is H, then R2 is CHR5CHR6CHO, CR5═CR6CHO or C(CH3)CHO, wherein R5, R6 each independently may represent H or methyl;R3 is H, or when R1 and R2 is H, then R3 is CHR5CHR6CHO, CR5═CR6CHO or C(CH3)CHO, wherein R5, R6 each independently may represent H or methyl; andR4 is methyl or a branched or linear, saturated or unsaturated, unsubstituted or substituted (optionally with cyclopropyl groups), C2-C7 alkyl or alkenyl residue, preferentially isobutyl, isoamyl.Said compounds are useful as perfume ingredients in personal care and household care products.

Claims

exact text as granted — not AI-modified
The invention claimed is: 
     
       1. A compound according to formula 1 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is H; 
         R 2  is H, or when R 1  and R 3  is H, then R 2  is CHR 5 CHR 6 CHO, CR 5 ═CR 6 CHO or C(CH 3 )CHO, wherein R 5 , R 6  each independently may represent H or methyl; 
         R 3  is H, or when R 1  and R 2  is H, then R 3  is CHR 5 CHR 6 CHO, CR 5 ═CR 6 CHO or C(CH 3 )CHO, wherein R 5 , R 6  each independently may represent H or methyl; 
         and 
         R 4  is a branched or linear, saturated or unsaturated, unsubstituted or substituted residue, or a C 2 -C 7  alkyl or alkenyl residueThe compound, 3-(2-isobutyl-4-methylphenyl)propanal. 
       
     
     
       2. The compound according to  claim 1  which is a perfume ingredient A pro-perfume which releases the compound, 3-(2-isobutyl-4-methylphenyl)propanal. 
     
     
       3. The compound of  claim 2 , which exhibits green odour characteristics. 
     
     
       4. A pro-perfume, which releases the compound represented by the formula 1 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is H; 
         R 2  is H, or when R 1  and R 3  is H, then R 2  is CHR 5 CHR 6 CHO, CR 5 ═CR 6 CHO or C(CH 3 )CHO, wherein R 5 , R 6  each independently may represent H or methyl; 
         R 3  is H, or when R 1  and R 2  is H, then R 3  is CHR 5 CHR 6 CHO, CR 5 ═CR 6 CHO or C(CH 3 )CHO, wherein R 5 , R 6  each independently may represent H or methyl; and 
         R 4  is a branched or linear, saturated or unsaturated, unsubstituted or substituted residue, C 2 -C 7  alkyl or alkenyl residue. 
       
     
     
       5. The pro-perfume of  claim 4 , which is an imine, aminal, hemi-aminal or enamine of the compound according to formula I. 
     
     
       6. The pro-perfume of  claim 4  which is a perfume ingredient. 
     
     
       7. The pro-perfume of  claim 6  which exhibits green odor characteristics. 
     
     
       8. A perfume composition comprising the pro-perfume of  claim 4 . 
     
     
       9. A personal care or household care composition comprising at least a pro-perfume as defined in  claim 4 . 
     
     
       10. A method of imparting muguet odour characteristics to a fine fragrance or consumer product comprising the step of adding thereto a pro-perfume as defined in  claim 4  and, selectively excluding from said fine fragrance or consumer product any aryl-substituted alkanal compounds, which are unsubstituted on the ring at the position ortho to the substituent containing aldehyde functionality, said selective addition or exclusion being based on the susceptibility of said compounds to enzymatically-mediated degradation to their benzoic acid derivatives when incubated with hepatocytes isolated from rats, said compounds being suitable for addition on the basis that they do not degrade to their benzoic acid derivatives, whereas said compounds being excluded on the basis that they do degrade to their benzoic acid derivatives. 
     
     
       11. A perfume composition comprising a compound according to  claim 1 . 
     
     
       12. A perfume composition according to  claim 11  that is substantially free of any aryl-substituted propanal odourants, that are unsubstituted on the aryl ring at a position ortho to the substituent bearing the aldehyde functionality. 
     
     
       13. A perfume composition according to  claim 11  comprising one or more additional fragrance ingredients. 
     
     
       14. A perfume composition according to  claim 13  which comprises 3-(4-isobutyl-2-methylphenyl)propanal. 
     
     
       15. A personal care or household care composition comprising at least a perfume composition according to  claim 11 . 
     
     
       16. A perfume composition according to  claim 11  that is substantially free of LILIAL. 
     
     
       17. A personal care or household care composition comprising at least a compound as defined in  claim 1 . 
     
     
       18. A personal care or household care composition according to  claim 17 , further comprising enzymes. 
     
     
       19. A personal or household care composition according to  claim 17 , which is a textile treatment product. 
     
     
       20. A personal or household care composition according to  claim 17  which is a detergent composition. 
     
     
       21. A method of imparting muguet odour characteristics to a fine fragrance or consumer product comprising the step of adding thereto a compound as defined in the compound of  claim 1  and, selectively excluding from said fine fragrance or consumer product any aryl-substituted alkanal compounds, which are unsubstituted on the ring at the position ortho to the substituent containing aldehyde functionality, said selective addition or exclusion being based on the susceptibility of said compounds to enzymatically-mediated degradation to their benzoic acid derivatives when incubated with hepatocytes isolated from rats, said compounds being suitable for addition on the basis that they do not degrade to their benzoic acid derivatives, whereas said compounds being excluded on the basis that they do degrade to their benzoic acid derivatives. 
     
     
       22. The compound of claim 1, which exhibits green odour characteristics.  
     
     
       23. A perfume composition comprising the compound of claim 1.   
     
     
       24. The perfume composition of claim 23 which is substantially free of any aryl-substituted propanal odourants, that are unsubstituted on the aryl ring at a position ortho to the substituent bearing the aldehyde functionality.  
     
     
       25. A perfume composition according to claim 23 comprising one or more additional fragrance ingredients.  
     
     
       26. A personal care or household care composition comprising the compound of claim 1.   
     
     
       27. A personal care or household care composition comprising a perfume composition of claim 23.   
     
     
       28. A personal care or household care composition of claim 26, further comprising an enzyme.  
     
     
       29. A personal care or household care composition of claim 26, which is a textile treatment product.  
     
     
       30. A personal care or household care composition of claim 26, which is a detergent composition.  
     
     
       31. The perfume composition of claim 25 which comprises 3-(4-isobutyl-2-methylphenyl)propanal.  
     
     
       32. The pro-perfume of claim 2, which is an imine, aminal, hemi-aminal or enamine of 3-(2-isobutyl-4-methylphenyl)propanal.  
     
     
       33. The pro-perfume of claim 32 which releases a compound which exhibits green odor characteristics.  
     
     
       34. A perfume composition comprising the pro-perfume of claim 2.   
     
     
       35. A personal care or household care composition comprising the pro-perfume of claim 2.   
     
     
       36. A method of imparting muguet odour characteristics to a fine fragrance or consumer product comprising the step of adding thereto the pro-perfume of claim 2 and, selectively excluding from said fine fragrance or consumer product any aryl-substituted alkanal compounds, which are unsubstituted on the ring at the position ortho to the substituent containing aldehyde functionality, said selective addition or exclusion being based on the susceptibility of said compounds to enzymatically-mediated degradation to their benzoic acid derivatives when incubated with hepatocytes isolated from rats, said compounds being suitable for addition on the basis that they do not degrade to their benzoic acid derivatives, whereas said compounds being excluded on the basis that they do degrade to their benzoic acid derivatives.  
     
     
       37. A perfume composition according to claim 23 that is substantially free of 3-(4-tert-butylphenyl)-2-methylpropanal.

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