Patent Publication Number: US-4929599-A

Title: Perfuming ingredient

Description:
BRIEF SUMMARY OF THE INVENTION 
     The present invention relates to perfumery. It concerns more particularly a method for enhancing, improving or modifying the odor properties of a perfuming composition of perfumed product, which method comprises adding to said composition or product a fragrance effective amount of 2-(2,3,4,5,6,7-hexahydro-1,1,4,4-tetramethyl-2(1H)-indenyl)-ethyl acetate. 
     The invention also provides a perfuming composition containing as a perfuming ingredient 2-(2,3,4,5,6,7-hexahydro-1,1,4,4-tetramethyl-2(1H)-indenyl)-ethyl acetate. 
     A further object of the invention is to provide a perfumed product containing as a perfuming ingredient 2-(2,3,4,5,6,7-hexahydro-1,1,4,4-tetramethyl-2(1H)-indenyl)-ethyl acetate. 
     BACKGROUND OF THE INVENTION 
     The chemical structure of 2-(2,3,4,5,6,7-hexahydro-1,1,4,4-tetramethyl-2(1H)-indenyl)-ethyl acetate has been known for some time. The compound has in fact been described by R. T. Reddy and Y. R. Nayak in Tetrahedron 42, 4533 (1986). However, these authors only concerned themselves with examining the behavior of isolongifolene in the presence of a hydrogen halogenide, and separated the above-mentioned compound as an intermediate product without recognizing its intrinsic odor properties. 
     PREFERRED EMBODIMENTS OF THE INVENTION 
     It has now been discovered that 2-(2,3,4,5,6,7-hexahydro-1,1,4,4-tetramethyl-2(1H)-indenyl)-ethyl acetate possess very useful odor properties and that, as a result, it can be used advantageously as a perfuming ingredient for the preparation of perfume bases, perfuming compositions and perfumed products. 
     The odor properties of this compound are such that it can be used to develop notes of the woody, slightly amber type. This compound is also capable of imparting to the compositions to which it is added a very elegant musky note. These are very fine notes, perfectly convenient for the preparation of alcoholic perfumes or the reconstitution of natural oils, but which can equally be adapted for perfuming products such as shampoos, cosmetic preparations, body deodorants, soaps, powder or liquid detergents, fabric softeners or yet air deodorizers. 
     The bicyclic ester which is the object of the invention can be used alone in the above-mentioned products or, as is generally the case, in admixture with other perfuming ingredients, with solvents, diluting agents or carriers. 
     The proportions in which the compound of the invention can be used to achieve the desired perfuming effect vary within a wide range of values. The man skilled in the art is well aware that such concentrations can vary as a function of the specific fragrance effect desired and depends on the coingredients present in a given composition and on the nature of the products to be perfumed. 
     Thus, in many cases, concentrations of the order of 5-30% by weight, relative to the weight of the composition to which it is added, can be used. These values can of course be lower, for instance of the order of 0.1-0.5, or even 1%, when it is desired to perfume articles such as soaps, detergents or cosmetic preparations. 
     As coingredients, one can use any of the ingredients currently used in perfumery in admixture with the bicyclic ester of the invention, the usual criteria of physico-chemical stability and odor compatibility being respected. 
     As previously mentioned, the chemical structure of 2-(2,3,4,5,6,7-hexahydro-1,1,4,4-tetramethyl-2(1H)-indenyl)-ethyl acetate is disclosed in the scientific literature. This compound can be obtained from isolongifolene by treatment with hydrobromic or hydroiodic acid, followed by esterification. The process for its preparation may be schematically represented as follows [see Tetrahedron 42, 4533 (1986)]: 
    
    
     The invention will be illustrated in greater detail in the following non-restrictive examples. 
     EXAMPLE 1 
     Preparation of a perfumed detergent 
     A base composition consisting of a commercial powder detergent, with a neutral odor, was perfumed with 2-(2,3,4,5,6,7-hexahydro-1,1,4,4-tetramethyl-2(1H)-indenyl)-ethyl acetate, using 0.1 and 0.2% by weight of this compound relative to the weight of the base. As a result, a novel base was obtained possessing an odor character of the woody, balsamic and gently amber-musky type. 
     The thus obtained perfumed base composition was used for the general washing of linen, by means of an automatic washing machine at 60° C. After one cycle of washing and drying, the linen had a persistant and fresh character, and a fine, elegant woody, amber and musky odor. 
     EXAMPLE 2 
     Perfuming composition 
     A perfuming base composition of the &#34;fougere&#34; type was prepared by mixing the following ingredients (parts by weight): 
     
         ______________________________________                                    
Benzyl salicylate       180                                               
Bourbon geranium essential oil                                            
                        180                                               
Linalyl acetate         160                                               
Lemon essential oil     160                                               
Cyclosia (registered trademark) base.sup.(1)                              
                        120                                               
Amyl salicylate         120                                               
10%* Ylang-ylang essential oil                                            
                        100                                               
Sweet orange essential oil                                                
                        90                                                
Lavender oil            90                                                
50%*.sup.(2)            80                                                
10%* Vanillin           80                                                
Anisic aldehyde         75                                                
Tarragon essential oil  60                                                
Heliotropin             60                                                
Linalol                 60                                                
Benzyl acetate          50                                                
Patchouli essential oil 45                                                
Oriental sandalwood essential oil                                         
                        45                                                
50%* Oakmoss absolute   40                                                
Phenylethanol           40                                                
Citronellol             25                                                
Bourbon vetyver essential oil                                             
                        20                                                
Coumarin                10                                                
Methylnaphthylacetone   10                                                
Total                   1900                                              
______________________________________                                    
 *in diethyl phathalate                                                   
 .sup.(1) Firmenich SA: hydroxycitronellal                                
 .sup.(2) Schiff base hydroxycitronellal/methyl anthranilate              
 
    
     The addition of 30 g of 2-(2,3,4,5,6,7-hexahydro-1,1,4,4-tetramethyl-2(1H)-indenyl)-ethyl acetate to 190 g of the base composition thus prepared resulted in a novel composition whose overall odor character was richer, with a musky and ambrette side. The woody note of the base composition was also strengthened, resulting in increased volume. 
     EXAMPLE 3 
     Perfuming composition 
     A perfuming base composition for a masculine line was prepared as follows (parts by weight): 
     
         ______________________________________                                    
p-tert-Butyl-cyclohexyl acetate                                           
                       200                                                
10%* Oakmoss absolute  180                                                
Synthetic bergamot oil 140                                                
alpha-Hexylcinnamic aldehyde                                              
                       80                                                 
Iralia (registered trademark).sup.(1) (4)                                 
                       60                                                 
Hedione (registered trademark).sup.(2) (4)                                
                       20                                                 
Resinoid galbanum      20                                                 
Lavandin absolute      20                                                 
Dihydromyrcenol        20                                                 
Synthetic neroli oil   20                                                 
Synthetic basil oil    20                                                 
10%* Methyl-nonyl aldehyde                                                
                       20                                                 
Resinoid olibanum      20                                                 
20%* Pine absolute     10                                                 
Synthetic angelica root oil                                               
                       10                                                 
Eugenol                10                                                 
50%* Resinoid labdanum 10                                                 
Rosemary essential oil 10                                                 
Cypress essential oil  10                                                 
Mayol (registered trademark).sup.(3) (4)                                  
                       10                                                 
Isoeugenol              5                                                 
50%* Resinoid Benjoin Siam                                                
                        5                                                 
Total                  900                                                
______________________________________                                    
 *in diethyl phthalate                                                    
 .sup.(1) alpha-methylionone                                              
 .sup.(2) methyl dihydrojasmonate                                         
 .sup.(3) p-isopropyl-cyclohexylmethanol                                  
 .sup.(4) origin: Firmenich SA, Geneva                                    
 
    
     The addition of 10 g of 2-(2,3,4,5,6,7-hexahydro-1,1,4,4-tetramethyl-2(1H)-indenyl)-ethyl acetate to 90 g of this woody, aromatic, herbaceous base composition resulted in a novel composition whose odor character was much more elegant and round than that of the said base composition. In particular, the citrus note harmonized better. Furthermore, the new composition had a musk-ambrette odor.