Oxathiane and oxathiolane derivatives as perfuming agents

Claim 2

A perfume composition comprising a small but odoriferously effective amount of (A) a compound of formula (I): ##STR13## in which: (a) n stands for 1 and m represents zero or 1, and each of symbols R 1 to R 8 represents a hydrogen atom or a saturated or unsaturated, linear or branched alkyl radical containing from 1 to 11 carbon atoms, or (b) n stands for 1 and m represents zero or 1, each of symbols R 1 , R 2 , R 3 and R 4 have the above-described meaning, R 5 and R 7 each represents hydrogen and R 6 together with R 8 and the carbon atoms carrying them, in positions 5 and 6 respectively, form a lower alkyl substituted or unsubstituted cyclopentane or cyclohexane ring, or (c) n stands for 1 and m represents zero or 1, each of symbols R 1 , R 3 , R 5 , R 6 and R 7 represents hydrogen, R 2 represents a lower alkyl radical or a hydrogen atom, R 4 represents a para-lower alkyl or lower alkoxy substituted or unsubstituted phenyl or a lower alkyl substituted or unsubstituted cyclohexenyl radical, and R 8 stands for a lower alkyl, or (d) n stands for 1 and m represents zero or 1, each of symbols R 1 , R 3 , R 5 , R 6 and R 7 represents hydrogen, R 2 represents a para-lower alkyl or lower alkoxy substituted phenyl or a lower alkyl substituted or unsubstituted cyclohexenyl radical, R 4 represents a lower alkyl radical or a hydrogen atom, and R 8 stands for a lower alkyl or a hydrogen; and (B) another oderiferous compound or a perfume base.

Claim 3

A composition according to claim 1, in which said compound of formula (I) is in the form of one of its epimers or enantiomers.

Claim 4

A composition according to claim 1, in which said compound of formula (I) is in the form of a mixture of its epimers or enantiomers.

Claim 5

Method for improving or enhancing the odoriferous properties of perfumes which comprises adding thereto a small but odoriferously effective amount of at least one compound of formula (I): ##STR14## in which: (a) n stands for 1 and m represents zero or 1, and each of symbols R 1 to R 8 represents a hydrogen atom or a saturated or unsaturated, linear or branched alkyl radical containing from 1 to 11 carbon atoms, or (b) n stands for 1 and m represents zero or 1, each of symbols R 1 , R 2 , R 3 and R 4 have the above-described meaning, R 5 and R 7 each represents hydrogen and R 6 together with R 8 and the carbon atoms carrying them, in positions 5 and 6 respectively, form a lower alkyl substituted or unsubstituted cyclopentane or cyclohexane ring, or (c) n stands for 1 and m represents zero or 1, each of symbols R 1 , R 3 , R 5 , R 6 and R 7 represents hydrogen, R 2 represents a lower alkyl radical or a hydrogen atom, R 4 represents a para-lower alkyl or lower alkoxy substituted or unsubstituted phenyl or a lower alkyl substituted or unsubstituted cyclohexenyl radical, and R 8 stands for a lower alkyl, or (d) n stands for 1 and m represents zero or 1, each of symbols R 1 , R 3 , R 5 , R 6 and R 7 represents hydrogen, R 2 a para-lower alkyl or lower alkoxy substituted or unsubstituted phenyl or a lower alkyl substituted or unsubstituted cyclohexenyl radical, R 4 represents a lower alkyl radical or a hydrogen atom, and R 8 stands for a lower alkyl or a hydrogen atom.

Claim 6

Method for improving or enhancing the odoriferous properties of perfumes which comprises adding thereto a small but odoriferously effective amount of at least one compound of formula (I): ##STR14## in which: (a) n stands for 1 and m represents zero or 1, and each of symbols R 1 to R 8 represents a hydrogen atom or a saturated or unsaturated, linear or branched alkyl radical containing from 1 to 11 carbon atoms, or (b) n stands for 1 and m represents zero or 1, each of symbols R 1 , R 2 , R 3 and R 4 have the above-described meaning, R 5 and R 7 each represents hydrogen and R 6 together with R 8 and the carbon atoms carrying them, in positions 5 and 6 respectively, form a lower alkyl substituted or unsubstituted cyclopentane or cyclohexane ring, or (c) n stands for 1 and m represents zero or 1, each of symbols R 1 , R 3 , R 5 , R 6 and R 7 represents hydrogen, R 2 represents a lower alkyl radical or a hydrogen atom, R 4 represents a para-lower alkyl or lower alkoxy substituted or unsubstituted phenyl or a lower alkyl substituted or unsubstituted cyclohexenyl radical, and R 8 stands for a lower alkyl, or (d) n stands for 1 and m represents zero or 1, each of symbols R 1 , R 3 , R 5 , R 6 and R 7 represents hydrogen, R 2 a para-lower alkyl or lower alkoxy substituted or unsubstituted phenyl or a lower alkyl substituted or unsubstituted cyclohexenyl radical, R 4 represents a lower alkyl radical or a hydrogen atom, and R 8 stands for a lower alkyl or a hydrogen atom.

Claim 7

The method of claim 4 wherein the compound of formula II is 2-methyl-4-propyl-1,3-oxathiane.

Claim 8

The method of claim 4 wherein the compound of formula II is 2-methyl-4-propyl-1,3-oxathiane-3-oxide.

Claim 9

The method of claim 4 wherein the compound of formula II is 4-(2,2,6-Trimethyl-cyclohex-5-en-1-yl)-6-methyl-1,3-oxathiane.

Claim 10

The method of claim 4 wherein the compound of formula II is 5-butyl-2-oxa-4-thiabicyclo[4.3.0]nonane.

Claim 11

The method of claim 4 wherein the compound of formula II is 2,6-dimethyl-4-(2,2,6-trimethyl-cyclohex-5-en-1-yl)-1,3-oxathiane.

Claim 12

A perfume composition comprising an odiferously effective amount of of formula (II): ##STR15## wherein each of the symbols R 1 to R 8 represents a hydrogen atom or a saturated or unsaturated, linear or branched alkyl radical, and each of the indexes m and n means 0 or 1; and (B) another odoriferous compound or a perfume base.

Claim 13

A perfume composition comprising an odiferously effective amount of of formula (II): ##STR15## wherein each of the symbols R 1 to R 8 represents a hydrogen atom or a saturated or unsaturated, linear or branched alkyl radical, and each of the indexes m and n means 0 or 1; and (B) another odoriferous compound or a perfume base.

Claim 14

A perfume composition of claim 10 wherein the compound of formula (II) is 2-methyl-4-propyl-1,3-oxathiane.

Claim 17

A method according to claim 12 wherein the compound of formula (II) is 2-methyl-4-propyl-1,3-oxathiane.

Claim 18

Substantially pure 2-methyl-4-propyl-1,3-oxathiane.

Claim 19

Substantially pure 2-methyl-4-propyl-1,3-oxathiane.

Claim 20

4-Propyl-1,3-oxathiane.

Claim 21

4-Propyl-1,3-oxathiane.

Claim 22

2,2-Dimethyl-4-propyl-1,3-oxathiane.

Claim 23

2,2-Dimethyl-4-propyl-1,3-oxathiane.

Claim 24

2-Ethyl-4-propyl-1,3-oxathiane.

Claim 25

2-Ethyl-4-propyl-1,3-oxathiane.

Claim 26

4-(2,2,6-Trimethyl-cyclohex-5-en-1-yl)-6-methyl-1,3-oxathiane.

Claim 27

4-(2,2,6-Trimethyl-cyclohex-5-en-1-yl)-6-methyl-1,3-oxathiane.

Claim 28

5-Butyl-2-oxa-4-thiabicyclo[4.3.0]nonane.

Claim 29

5-Butyl-2-oxa-4-thiabicyclo[4.3.0]nonane.

Claim 30

2,2,-diethyl-4-n-propyl-1,3-oxathiane.

Claim 31

2,2,-diethyl-4-n-propyl-1,3-oxathiane.

Claim 32

2,4-dimethyl-1,3-oxathiolane.

Claim 33

2,4-dimethyl-1,3-oxathiolane.

Claim 34

Substantially pure 2-methyl-4-propyl-1,3-oxathiane-3-oxide.

Claim 35

Substantially pure 2-methyl-4-propyl-1,3-oxathiane-3-oxide.

Claim 36

A compound selected from the group consisting of: 4,4,6-trimethyl-1,3-oxathiane, 2,4,4,6-tetramethyl-1,3-oxathiane, 2-ethyl-4,4,6-trimethyl-1,3-oxathiane, 2-propyl-4,4,6-trimethyl-1,3-oxathiane, 4-propyl-1,3-oxathiane, 2-methyl-4-propyl-1,3-oxathiane, 2,2-dimethyl-4-propyl-1,3-oxathiane, 2-methyl-2-ethyl-4-propyl-1,3-oxathiane, 2-methyl-2,4-dipropyl-1,3-oxathiane, 2-ethyl-4-propyl-1,3-oxathiane, 2-ter-butyl-4-propyl-1,3-oxathiane, 2-pentyl-4-propyl-1,3-oxathiane, 2-(pent-1-enyl)-4-propyl-1,3-oxathiane, 2-methyl-2-hexyl-4-propyl-1,3-oxathiane, 2-octyl-4-propyl-1,3-oxathiane, 2-undecyl-4-propyl-1,3-oxathiane, 2-methyl-4-heptyl-1,3-oxathiane, 2,2-dimethyl-4-heptyl-1,3-oxathiane, 2-ethyl-4-heptyl-1,3-oxathiane, 2-pentyl-4-heptyl-1,3-oxathiane, 5-butyl-2-oxa-4-thiabicyclo[4.3.0]nonane, 3-methyl-5-butyl-2-oxa-4-thiabicyclo[4.3.0]nonane, 5,5,9-trimethyl-2-oxa-4-thiabicyclo[4.4.0]decane, 2,5,5,9-tetramethyl-2-oxa-4-thiabicyclo[4.4.0]decane, 5,5,9-trimethyl-3-ethyl-2-oxa-4-thiabicyclo[4.4.0]decane, 5,5,9-trimethyl-3-propyl-2-oxa-4-thiabicyclo[4.4.0]decane, 3,5,5,9-tetramethyl-3-propyl-2-oxa-4-thiabicyclo[4.4.0]decane, 2-methyl-4-propyl-1,3-oxathiane-3-oxide, 2-methyl-1,3-oxathiane-3-oxide, 2,2-dimethyl-1,3-oxathiane-3-oxide, 4-propyl-1,3-oxathiane-3-oxide, 2-pentyl-4-propyl-1,3-oxathiane-3-oxide, 2-methyl-6-propyl-1,3-oxathiane, 2,4,4,6-tetramethyl-2-propyl-1,3-oxathiane,

Claim 37

A compound selected from the group consisting of: 4,4,6-trimethyl-1,3-oxathiane, 2,4,4,6-tetramethyl-1,3-oxathiane, 2-ethyl-4,4,6-trimethyl-1,3-oxathiane, 2-propyl-4,4,6-trimethyl-1,3-oxathiane, 4-propyl-1,3-oxathiane, 2-methyl-4-propyl-1,3-oxathiane, 2,2-dimethyl-4-propyl-1,3-oxathiane, 2-methyl-2-ethyl-4-propyl-1,3-oxathiane, 2-methyl-2,4-dipropyl-1,3-oxathiane, 2-ethyl-4-propyl-1,3-oxathiane, 2-ter-butyl-4-propyl-1,3-oxathiane, 2-pentyl-4-propyl-1,3-oxathiane, 2-(pent-1-enyl)-4-propyl-1,3-oxathiane, 2-methyl-2-hexyl-4-propyl-1,3-oxathiane, 2-octyl-4-propyl-1,3-oxathiane, 2-undecyl-4-propyl-1,3-oxathiane, 2-methyl-4-heptyl-1,3-oxathiane, 2,2-dimethyl-4-heptyl-1,3-oxathiane, 2-ethyl-4-heptyl-1,3-oxathiane, 2-pentyl-4-heptyl-1,3-oxathiane, 5-butyl-2-oxa-4-thiabicyclo[4.3.0]nonane, 3-methyl-5-butyl-2-oxa-4-thiabicyclo[4.3.0]nonane, 5,5,9-trimethyl-2-oxa-4-thiabicyclo[4.4.0]decane, 2,5,5,9-tetramethyl-2-oxa-4-thiabicyclo[4.4.0]decane, 5,5,9-trimethyl-3-ethyl-2-oxa-4-thiabicyclo[4.4.0]decane, 5,5,9-trimethyl-3-propyl-2-oxa-4-thiabicyclo[4.4.0]decane, 3,5,5,9-tetramethyl-3-propyl-2-oxa-4-thiabicyclo[4.4.0]decane, 2-methyl-4-propyl-1,3-oxathiane-3-oxide, 2-methyl-1,3-oxathiane-3-oxide, 2,2-dimethyl-1,3-oxathiane-3-oxide, 4-propyl-1,3-oxathiane-3-oxide, 2-pentyl-4-propyl-1,3-oxathiane-3-oxide, 2-methyl-6-propyl-1,3-oxathiane, 2,4,4,6-tetramethyl-2-propyl-1,3-oxathiane,