Fragrances with note of lily of the valley

Abstract

A compound of formula (I) is described and use thereof as fragrance, especially as lily-of-the-valley fragrance and/or as an agent for increasing the substantivity and/or the retention of a fragrance preparation and/or as a fixative.

1 . A compound selected from the group consisting of a compound of formula (Ia) 
       
         
           
           
               
               
           
         
       
       and a compound of formula (Ib) 
       
         
           
           
               
               
           
         
       
     
     
         2 . A mixture, comprising a compound of formula (Ia) and a compound of formula (Ib), as defined in  claim 1 . 
     
     
         3 . A mixture according to  claim 2 , wherein
 the mass ratio of the compound of formula (Ia) to the compound of formula (Ib) is in the range from 0.01 to 99.99 and/or   the total proportion of compounds of formulas (Ia) and (Ib) is greater than 0.01 wt.   
     
     
         4 . (canceled) 
     
     
         5 . (canceled) 
     
     
         6 . A fragrance preparation, comprising:
 a compound of formula (I)   
       
         
           
           
               
               
           
         
         and 
         an additional fragrance that is not a compound of formula (I). 
       
     
     
         7 . A fragrance preparation according to  claim 6 , wherein the amount of a compound of formula (Ia) 
       
         
           
           
               
               
           
         
       
       and/or a compound of formula (Ib) 
       
         
           
           
               
               
           
         
       
       is in the range from 0.0001 to 40 wt relative to the total weight of the fragrance preparation. 
     
     
         8 . A fragrance preparation according to  claim 6  comprising an additional fragrance with an odor note of lily of the valley. 
     
     
         9 . A fragrance preparation according to  claim 6 , wherein
 (i) the amount of the compound of formula (Ia) is sufficient to endow the fragrance preparation with an odor note of lily of the valley,
 and/or 
   (ii) an additional fragrance of the fragrance preparation imparts an odor note of lily of the valley, wherein the amount of the compound of formula (Ia) is sufficient, in comparison with a comparative fragrance preparation of otherwise identical composition without the compound of formula (Ia), to modify and/or to intensify the odor note of lily of the valley,
 and/or 
   (iii) the amount of the compound of formula (Ia) is sufficient to endow the fragrance preparation with an impression selected from the group consisting of natural, caring, complex and radiant
 and/or 
   (iv) the amount of the compound of formula (Ia) is sufficient to modify and/or to intensify an impression selected from the group consisting of natural, caring, complex and radiant in comparison with a comparative fragrance preparation of otherwise identical composition without the compound of formula (Ia)
 and/or 
   (v) the amount of the compound of formula (Ib) is sufficient to endow the fragrance preparation with an odor note of lily of the valley,
 and/or 
   (vi) an additional fragrance of the fragrance preparation imparts an odor note of lily of the valley, wherein the amount of the compound of formula (Ib) is sufficient, in comparison with a comparative fragrance preparation of otherwise identical composition without the compound of formula (Ib), to modify and/or to intensify the odor note of lily of the valley.   
     
     
         10 . A perfumed product comprising
 a compound of formula (I) as defined in  claim 1  in a sensorially effective amount.   
     
     
         11 . A perfumed product according to  claim 10 , wherein the amount of a compound of formula (Ia) and/or a compound of formula (Ib) is in the range from 0.0001 to 5 wt %, relative to the total weight of the product. 
     
     
         12 . A perfumed product according to  claim 10 , selected from the group consisting of washing and cleaning products, hygiene products, and care products. 
     
     
         13 . A method for of providing skin, hair, surfaces, or textile fibers with an odor note of lily of the valley comprising applying a fragrance preparation according to  claim 6  to the skin, hair, surfaces, or textile fibers. 
     
     
         14 . A method for producing the compound of formula (I) 
       
         
           
           
               
               
           
         
         comprising an acid-catalyzed reaction of an acetal of formula (II), 
       
       
         
           
           
               
               
           
         
         wherein R is a linear or branched, saturated or unsaturated alkyl group with 1 to 10 carbon atoms. 
       
     
     
         15 . An acetal of formula (II) 
       
         
           
           
               
               
           
         
         wherein R is a linear or branched, saturated or unsaturated alkyl group with 1 to 10 carbon atoms. 
       
     
     
         16 . A method for producing a compound of formula (Ia) or a compound of formula (Ib) as defined in  claim 1 , or a mixture of compounds of formula (Ia) and (Ib), comprising the use
 of d-(+) limonene as educt for producing the compound of formula (Ia),   of 1-(−) limonene as educt for producing the compound of formula (Ib) as, or   of a mixture containing d-(+) limonene and 1-(−) limonene as educt for producing a mixture containing the compound of formula (Ia) and the compound of formula (Ib).   
     
     
         17 . A method for producing a compound of formula (I) as defined in  claim 6  comprising pyrolysis of the spirolactone of formula (VIII) to form the compound of formula (I) 
       
         
           
           
               
               
           
         
       
     
     
         18 . A method for mediating, intensifying and/or modifying an odor note of lily of the valley to a substance comprising bringing the substance into contact with a compound according to  claim 1 .
 a compound of formula (I),   
     
     
         19 . A method for mediating, intensifying and/or modifying an odor note of lily of the valley to a substance comprising bringing the substance into contact with a mixture according to  claim 2 . 
     
     
         20 . A method for mediating, intensifying and/or modifying an odor note of lily of the valley to a substance comprising bringing the substance into contact with a fragrance preparation according to  claim 6 . 
     
     
         21 . A method for mediating, intensifying and/or modifying an odor note of lily of the valley to a substance comprising bringing the substance into contact with a fragrance preparation according to  claim 7 . 
     
     
         22 . A method for increasing the sub stantivity and/or the retention of a fragrance comprising combining the fragrance with a compound of formula (I) as defined in  claim 6 .