Unsaturated macrocyclic epoxide as perfuming ingredient

Abstract

The present invention relates to a compound of formula (I) in the form of any one of its stereoisomers or a mixture thereof which is useful as perfuming ingredients.

1 . In a perfuming composition or perfuming consumer product, the improvement which comprises including therein a perfuming ingredient of a compound of formula (I) 
       
         
           
           
               
               
           
         
       
       in the form of any one of its stereoisomers or of any mixture thereof and wherein the dotted line represents a carbon-carbon single or double bond. 
     
     
         2 . The improvement according to  claim 1 , wherein the compound (I) is in the form of a composition of matter comprising predominantly the following stereoisomers:
 (1RS,4E,8E,12RS)-13-oxabicyclo[10.1.0]trideca-4,8-diene, also referred to as isomer (A);   (1RS,4E,8E,12SR)-13-oxabicyclo[10.1.0]trideca-4,8-diene, also referred to as isomer (B); and   (1RS,4E,8Z,12RS)-13-oxabicyclo[10.1.0]trideca-4,8-diene, also referred to as isomer (C).   
     
     
         3 . The improvement according to  claim 1 , wherein the compound (I) is in the form of a composition of matter comprising essentially, or even consisting of, the isomers (A), (B) and (C) in the following weight %:
 (A) being comprised between 0% and 5%, preferably between 0% and 3%;   (B) being comprised between 5% and 30%, preferably between 7% and 22%; and   (C) being comprised between 65% and 90%, preferably between 72% and 85%.   
     
     
         4 . The improvement according to  claim 1 , wherein the compound (I) is in the form of a composition of matter comprising essentially, or even consisting of, the isomers (A), (B) and (C) in the following weight%:
 (A) being comprised between 50% and 75%, preferably between 60% and 70%;   (B) being comprised between 0% and 5%, preferably between 0% and 3%; and   (C) being comprised between 20% and 50%, preferably between 27% and 40%.   
     
     
         5 . The improvement according to  claim 1 , wherein the compound (I) is in the form of a composition of matter comprising essentially, or even consisting of, the isomers (A), (B) and (C) in the following weight ratio:
 (A)/(C)/(B)=1/80/19 obtainable from epoxydation of compound (II-a);   (A)/(C)/(B)=63/36/1 obtainable from epoxydation of compound (II-b); or   (A)/((C)+(B))=99/1 obtainable from epoxydation of compound (II-c).   
     
     
         6 . The improvement according to  claim 1 , wherein the compound of formula (I) is obtainable by the process comprising the step of treating cyclododaca-1,5,9-triene in the form of any one of its stereoisomers or of any mixture thereof with an epoxidizing agent and optionally monohydrogenating one double bond. 
     
     
         7 . The improvement according to  claim 1 , wherein the cyclododecatriene is in the form of a mixture of isomer (1Z,4E,8E) and isomer (1E,4E,8E) comprising at least 98% w/w of the isomer (1Z,4E,8E), the rest being the isomer (1E,4E,8E) or cyclododecatriene is in the form of a mixture comprising at least 30% w/w of the isomer (1Z,5E,9E), at most 75 w/w of the isomer (1E,5E,9E) and at most 5% w/w of the isomer (1Z,5Z,9E). 
     
     
         8 . A perfuming composition comprising
 i) at least one compound of formula (I), as defined in  claim 1 ;   ii) at least one ingredient selected from the group consisting of a perfumery carrier and a perfumery base; and   iii) optionally at least one perfumery adjuvant.   
     
     
         9 . A perfuming consumer product comprising at least one compound of formula (I), as defined in  claim 1 . 
     
     
         10 . A perfuming consumer product according to  claim 9 , characterized in that the perfumery consumer product is a perfume, a fabric care product, a body-care product, an air care product or a home care product. 
     
     
         11 . A perfuming consumer product according to  claim 9 , characterized in that the perfumery consumer product is a fine perfume, a cologne, an after-shave lotion, a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, a paper, a bleach, a shampoo, a coloring preparation, a hair spray, a vanishing cream, a deodorant or antiperspirant, a perfumed soap, shower or bath mousse, oil or gel, a hygiene product, an air freshener, a “ready to use” powdered air freshener, a wipe, a dish detergent or hard-surface detergent. 
     
     
         12 . The perfuming composition of  claim 8 , wherein the compound (I) is in the form of a composition of matter comprising essentially, or even consisting of, the isomers (A), (B) and (C) in the following weight%:
 (A) being comprised between 0% and 5%, preferably between 0% and 3%;   (B) being comprised between 5% and 30%, preferably between 7% and 22%; and   (C) being comprised between 65% and 90%, preferably between 72% and 85%.   
     
     
         13 . The perfuming composition of  claim 8 , wherein the compound (I) is in the form of a composition of matter comprising essentially, or even consisting of, the isomers (A), (B) and (C) in the following weight%:
 (A) being comprised between 50% and 75%, preferably between 60% and 70%;   (B) being comprised between 0% and 5%, preferably between 0% and 3%; and   (C) being comprised between 20% and 50%, preferably between 27% and 40%.   
     
     
         14 . The perfuming composition of  claim 8 , wherein the compound (I) is in the form of a composition of matter comprising essentially, or even consisting of, the isomers (A), (B) and (C) in the following weight ratio:
 (A)/(C)/(B)=1/80/19 obtainable from epoxydation of compound (II-a);   (A)/(C)/(B)=63/36/1 obtainable from epoxydation of compound (II-b); or   (A)/((C)+(B))=99/1 obtainable from epoxydation of compound (II-c).   
     
     
         15 . The perfuming consumer product of  claim 9 , wherein the compound (I) is in the form of a composition of matter comprising essentially, or even consisting of, the isomers (A), (B) and (C) in the following weight%:
 (A) being comprised between 0% and 5%, preferably between 0% and 3%;   (B) being comprised between 5% and 30%, preferably between 7% and 22%; and   (C) being comprised between 65% and 90%, preferably between 72% and 85%.   
     
     
         16 . The perfuming consumer product of  claim 9 , wherein the compound (I) is in the form of a composition of matter comprising essentially, or even consisting of, the isomers (A), (B) and (C) in the following weight%:
 (A) being comprised between 50% and 75%, preferably between 60% and 70%;   (B) being comprised between 0% and 5%, preferably between 0% and 3%; and   (C) being comprised between 20% and 50%, preferably between 27% and 40%.   
     
     
         17 . The perfuming consumer product of  claim 9 , wherein the compound (I) is in the form of a composition of matter comprising essentially, or even consisting of, the isomers (A), (B) and (C) in the following weight ratio:
 (A)/(C)/(B)=1/80/19 obtainable from epoxydation of compound (II-a);   (A)/(C)/(B)=63/36/1 obtainable from epoxydation of compound (II-b); or   (A)/((C)+(B))=99/1 obtainable from epoxydation of compound (II-c).