Fragrance compositions containing norbornene derivatives
Embodiments in accordance with the present invention relate generally to a variety of norbornene derivatives exhibiting olfactive properties and are suitable as fragrance ingredients. More specifically, this invention relates to various fragrance compositions containing one or more of a compound of formula (I): Wherein R 1 , R 2 , R 3 and R 4 are as defined herein. The compounds of formula (I) are useful as perfumes, colognes, and in perfume augmenting, modifying, enhancing, and imparting compositions. The compositions of this invention are therefore useful in a variety of products including perfumes, colognes, soaps, detergents, candles, air fresheners, trash bags, tissues, deodorants, lotions, skin care products, hair products, sanitary products, cleaning products, and the like.
1. A fragrance composition comprising:
a) an effective amount of at least one compound of formula (I) in the form of any one of its enantiomers or a mixture thereof:
wherein:
at least one of R 1 , R 2 , R 3 and R 4 is selected from the group consisting of:
substituted or unsubstituted (C 3 -C 8 )cycloalkyl; substituted or unsubstituted (CR 5 R 6 ) a (C 3 -C 8 )cycloalkyl; substituted or unsubstituted phenyl;
a group of formula (A):
—Z—(CO)OR (A); and
a group of formula (D):
—Z—CR 5 ((CO)OR) 2 (D);
wherein:
Z is a bond or a group selected from the group consisting of:
(CR 5 R 6 ) a , (CR 5 R 6 ) a —O—(CR 5 R 6 ) b , (CR 5 R 6 ) a —(CO)O—(CR 5 R 6 ) b , (CR 5 R 6 ) a —O(CO)—(CR 5 R 6 ) b , (CR 5 R 6 ) a —(CO)—(CR 5 R 6 ) b , where a and b are integers which may be the same or different and each independently is 1 to 12;
R 5 and R 6 are the same or different and each independently selected from the group consisting of hydrogen, methyl, ethyl, linear or branched (C 3 -C 6 )alkyl, perfluoro(C 1 -C 12 )alkyl, (C 3 -C 12 )cycloalkyl, (C 6 -C 12 )bicycloalkyl, (C 7 -C 14 )tricycloalkyl, (C 6 -C 10 )aryl, (C 6 -C 10 )aryl(C 1 -C 6 )alkyl, perfluoro(C 6 -C 10 )aryl, perfluoro(C 6 -C 10 )aryl(C 1 -C 3 )alkyl, (C 2 -C 6 )acyl, hydroxymethyl, hydroxyethyl and linear or branched hydroxy(C 3 -C 6 )alkyl;
R is selected from the group consisting of hydrogen, methyl, ethyl, linear or branched (C 3 -C 6 )alkyl, perfluoro(C 1 -C 12 )alkyl, (C 3 -C 12 )cycloalkyl, (C 6 -C 12 )bicycloalkyl, (C 7 -C 14 )tricycloalkyl, (C 6 -C 10 )aryl, (C 6 -C 10 )aryl(C 1 -C 6 )alkyl, perfluoro(C 6 -C 10 )aryl, perfluoro(C 6 -C 10 )aryl(C 1 -C 3 )alkyl, methoxy, ethoxy, linear or branched (C 3 -C 6 )alkoxy, perfluoro(C 1 -C 12 )alkoxy, (C 3 -C 12 )cycloalkoxy, (C 6 -C 12 )bicycloalkoxy, (C 7 -C 14 )tricycloalkoxy, (C 6 -C 10 )aryloxy, (C 6 -C 10 )aryl(C 1 -C 6 )alkoxy, (C 2 -C 4 )alkenyl(C 6 -C 10 )aryl(C 1 -C 6 )alkoxy, perfluoro(C 6 -C 10 )aryloxy, perfluoro(C 6 -C 10 )aryl(C 1 -C 3 )alkoxy, (C 2 -C 6 )acyl, hydroxymethyl, hydroxyethyl and linear or branched hydroxy(C 3 -C 6 )alkyl; and
the remaining R 1 , R 2 , R 3 and R 4 is selected from the group consisting of hydrogen, methyl, ethyl, linear or branched (C 3 -C 6 )alkyl, perfluoro(C 1 -C 12 )alkyl, (C 3 -C 12 )cycloalkyl, (C 6 -C 12 )bicycloalkyl, (C 7 -C 14 )tricycloalkyl, (C 6 -C 10 )aryl, (C 6 -C 10 )aryl(C 1 -C 6 )alkyl, perfluoro(C 6 -C 10 )aryl, perfluoro(C 6 -C 10 )aryl(C 1 -C 3 )alkyl, methoxy, ethoxy, linear or branched (C 3 -C 6 )alkoxy, perfluoro(C 1 -C 12 )alkoxy, (C 3 -C 12 )cycloalkoxy, (C 6 -C 12 )bicycloalkoxy, (C 7 -C 14 )tricycloalkoxy, (C 6 -C 10 )aryloxy, (C 6 -C 10 )aryl(C 1 -C 6 )alkoxy, perfluoro(C 6 -C 10 )aryloxy, perfluoro(C 6 -C 10 )aryl(C 1 -C 3 )alkoxy, (C 2 -C 6 )acyl, hydroxymethyl, hydroxyethyl and linear or branched hydroxy(C 3 -C 6 )alkyl;
with the proviso that when Z is a bond, R is not hydrogen, methyl, ethyl, linear or branched (C 3 -C 6 )alkyl;
b) at least one ingredient selected from the group consisting of a fragrance carrier and a fragrance base; and
c) optionally at least one fragrance adjuvant.
2. The fragrance composition according to claim 1 , wherein said at least one of R 1 , R 2 , R 3 and R 4 is substituted or unsubstituted (C 3 -C 8 )cycloalkyl and the remaining R 1 , R 2 , R 3 and R 4 is selected from the group consisting of hydrogen, methyl, ethyl, linear or branched propyl, linear or branched butyl, CF 3 , cyclohexyl, phenyl, benzyl, phenethyl, C 6 F 5 , methoxy, ethoxy, phenoxy, hydroxymethyl and hydroxyethyl.
3. The fragrance composition according to claim 2 , wherein said compound of formula (I) is
4. The fragrance composition according to claim 1 , wherein said at least one of R 1 , R 2 , R 3 and R 4 is a group of formula (A):
—Z—(CO)OR (A);
wherein:
Z is a bond or a group selected from the group consisting of:
(CH 2 ) a , (CH 2 ) a —O—(CH 2 ) b , where a and b are integers which may be the same or different and each independently is 1 to 4;
R is selected from the group consisting of methyl, ethyl, linear or branched propyl, linear or branched butyl, CF 3 , cyclohexyl, phenyl, benzyl, phenethyl, C 6 F 5 and methyladamantanyl; and
the remaining R 1 , R 2 , R 3 and R 4 is selected from the group consisting of hydrogen, methyl, ethyl, linear or branched propyl, linear or branched butyl, CF 3 , cyclohexyl, phenyl, benzyl, phenethyl, C 6 F 3 , methoxy, ethoxy, phenoxy, hydroxymethyl and hydroxyethyl.
5. The fragrance composition according to claim 4 , wherein said compound of formula (I) is selected from the group consisting of:
6. A fragrance composition comprising:
a) an effective amount of at least one compound of formula (I) in the form of any one of its enantiomers or a mixture thereof:
wherein
at least one of R 1 , R 2 , R 3 and R 4 is a group of formula (B):
—Z—O(CO)R (B);
wherein:
Z is selected from the group consisting of:
(CH 2 ) a , and (CH 2 ) a —O—(CH 2 ) b , where a and b are integers which may be the same or different and each independently is 1 to 4;
R is selected from the group consisting of cyclohexyl, phenyl, benzyl, phenethyl, and —CH═CH—C 6 H 4 —OCH 3 ; and
the remaining R 1 , R 2 , R 3 and R 4 is selected from the group consisting of hydrogen, methyl, ethyl, linear or branched propyl, linear or branched butyl, CF 3 , cyclohexyl, phenyl, benzyl, phenethyl, C 6 F 5 , methoxy, ethoxy, phenoxy, hydroxymethyl and hydroxyethyl,
b) at least one ingredient selected from the group consisting of a fragrance carrier and a fragrance base; and
c) optionally at least one fragrance adjuvant.
7. The fragrance composition according to claim 6 , wherein said compound of formula (I) is:
8. The fragrance composition according to claim 1 , wherein said at least one of R 1 , R 2 , R 3 and R 4 is a group of formula (D):
—Z—CR 5 ((CO)OR) 2 (D);
wherein:
Z is a bond or a group selected from the group consisting of:
(CH 2 ) a , (CH 2 ) a —O—(CH 2 ) b , where a and b are integers which may be the same or different and each independently is 1 to 4;
R 5 is selected from the group consisting of hydrogen, methyl and ethyl;
R is selected from the group consisting of methyl, ethyl, linear or branched propyl, linear or branched butyl, cyclohexyl, phenyl, benzyl and phenethyl; and
the remaining R 1 , R 2 , R 3 and R 4 is selected from the group consisting of hydrogen, methyl, ethyl, linear or branched propyl, linear or branched butyl, CF 3 , cyclohexyl, phenyl, benzyl, phenethyl, C 6 F 5 , methoxy, ethoxy, phenoxy, hydroxymethyl and hydroxyethyl.
9. The fragrance composition according to claim 8 , wherein said compound of formula (I) is selected from the group consisting of:
10. A fragrance composition comprising:
a) an effective amount of at least one compound of formula (I) in the form of any one of its enantiomers or a mixture thereof:
wherein
at least one of R 1 , R 2 , R 3 and R 4 is a group of formula (E):
—Z—OR (E);
wherein:
Z is (CR 5 R 6 ) a where a is 1 to 4 and each R 5 and R 6 is independently selected from the group consisting of methyl and ethyl;
R is selected from the group consisting of hydrogen, methyl, ethyl, linear or branched propyl, linear or branched butyl, cyclohexyl, phenyl, benzyl and phenethyl; and
the remaining R 1 , R 2 , R 3 and R 4 is selected from the group consisting of hydrogen, methyl, ethyl, linear or branched propyl, linear or branched butyl, CF 3 , cyclohexyl, phenyl, benzyl, phenethyl, C 6 F 5 , methoxy, ethoxy, phenoxy, hydroxymethyl and hydroxyethyl;
b) at least one ingredient selected from the group consisting of a fragrance carrier and a fragrance base; and
c) optionally at least one fragrance adjuvant.
11. The fragrance composition according to claim 10 , wherein said compound of formula (I) is selected from the group consisting of:
12. 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.
13. A perfuming consumer product comprising: i) at least one compound of formula (I), as defined in claim 1 ; and ii) a perfumery consumer base.
14. A perfuming consumer product according to claim 13 , wherein said perfumery consumer base is a perfume, a fabric care product, a body-care product, an air care product or a home care product.
15. A perfuming consumer product according to claim 13 , wherein said perfumery consumer base 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.
16. A method to confer, enhance, improve or modify the odor properties of a perfuming composition or of a perfumed article, which method comprises adding to said composition or article an effective amount of at least one compound of formula (I) in the form of any one of its enantiomers or a mixture thereof:
wherein:
at least one of R 1 , R 2 , R 3 and R 4 is selected from the group consisting of:
substituted or unsubstituted (C 3 -C 8 )cycloalkyl; substituted or unsubstituted (CR 5 R 6 ) a (C 3 -C 8 )cycloalkyl; substituted or unsubstituted phenyl;
a group of formula (A):
—Z—(CO)OR (A); and
a group of formula (D):
—Z—CR 5 ((CO)OR) 2 (D);
wherein:
Z is a bond or a group selected from the group consisting of:
(CR 5 R 6 ) a , (CR 5 R 6 ) a —O—(CR 5 R 6 ) b , (CR 5 R 6 ) a —(CO)O—(CR 5 R 6 ) b , (CR 5 R 6 ) a —O(CO)—(CR 5 R 6 ) b , (CR 5 R 6 ) a —(CO)—(CR 5 R 6 ) b , where a and b are integers which may be the same or different and each independently is 1 to 12;
R 5 and R 6 are the same or different and each independently selected from the group consisting of hydrogen, methyl, ethyl, linear or branched (C 3 -C 6 )alkyl, perfluoro(C 1 -C 12 )alkyl, (C 3 -C 12 )cycloalkyl, (C 6 -C 12 )bicycloalkyl, (C 7 -C 14 )tricycloalkyl, (C 6 -C 10 )aryl, (C 6 -C 10 )aryl(C 1 -C 6 )alkyl, perfluoro(C 6 -C 10 )aryl, perfluoro(C 6 -C 10 )aryl(C 1 -C 3 )alkyl, (C 2 -C 6 )acyl, hydroxymethyl, hydroxyethyl and linear or branched hydroxy(C 3 -C 6 )alkyl;
R is selected from the group consisting of hydrogen, methyl, ethyl, linear or branched (C 3 -C 6 )alkyl, perfluoro(C 1 -C 12 )alkyl, (C 3 -C 12 )cycloalkyl, (C 6 -C 12 )bicycloalkyl, (C 7 -C 14 )tricycloalkyl, (C 6 -C 10 )aryl, (C 6 -C 10 )aryl(C 1 -C 6 )alkyl, perfluoro(C 6 -C 10 )aryl, perfluoro(C 6 -C 10 )aryl(C 1 -C 3 )alkyl, methoxy, ethoxy, linear or branched (C 3 -C 6 )alkoxy, perfluoro(C 1 -C 12 )alkoxy, (C 3 -C 12 )cycloalkoxy, (C 6 -C 12 )bicycloalkoxy, (C 7 -C 14 )tricycloalkoxy, (C 6 -C 10 )aryloxy, (C 6 -C 10 )aryl(C 1 -C 6 )alkoxy, (C 2 -C 4 )alkenyl(C 6 -C 10 )aryl(C 1 -C 6 )alkoxy, perfluoro(C 6 -C 10 )aryloxy, perfluoro(C 6 -C 10 )aryl(C 1 -C 3 )alkoxy, (C 2 -C 6 )acyl, hydroxymethyl, hydroxyethyl and linear or branched hydroxy(C 3 -C 6 )alkyl; and
the remaining R 1 , R 2 , R 3 and R 4 is selected from the group consisting of hydrogen, methyl, ethyl, linear or branched (C 3 -C 6 )alkyl, perfluoro(C 1 -C 12 )alkyl, (C 3 -C 12 )cycloalkyl, (C 6 -C 12 )bicycloalkyl, (C 7 -C 14 )tricycloalkyl, (C 6 -C 10 )aryl, (C 6 -C 10 )aryl(C 1 -C 6 )alkyl, perfluoro(C 6 -C 10 )aryl, perfluoro(C 6 -C 10 )aryl(C 1 -C 3 )alkyl, methoxy, ethoxy, linear or branched (C 3 -C 6 )alkoxy, perfluoro(C 1 -C 12 )alkoxy, (C 3 -C 12 )cycloalkoxy, (C 6 -C 12 )bicycloalkoxy, (C 7 -C 14 )tricycloalkoxy, (C 6 -C 10 )aryloxy, (C 6 -C 10 )aryl(C 1 -C 6 )alkoxy, perfluoro(C 6 -C 10 )aryloxy, perfluoro(C 6 -C 10 )aryl(C 1 -C 3 )alkoxy, (C 2 -C 6 )acyl, hydroxymethyl, hydroxyethyl and linear or branched hydroxy(C 3 -C 6 )alkyl.
17. The method according to claim 16 , wherein said compound of formula (I) is selected from the group consisting of:
18. The method according to claim 16 , wherein said compound of formula (I) is selected from the group consisting of:
19. A perfuming composition comprising i) at least one compound of formula (I), as defined in claim 6 ; 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.
20. A perfuming composition comprising i) at least one compound of formula (I), as defined in claim 10 ; 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.