TERPENOL ETHERS
The present disclosure is directed to novel ether derivatives of terpenes, particularly derivatives of terpene alcohols, and methods of making them, compositions comprising them, and methods for using them.
1 . A compound of the general formula (I):
in free or salt form, wherein A is selected from the group consisting of 2,4-dimethyloctan-2-yl, 2,6-dimethyl-octan-1-yl, 2,6-dimethyloctan-2-yl, 3,7-dimethyloctan-1-yl, and 3,7-dimethyloctan-3-yl;
and wherein B is —(CH 2 ) x CH═CH(CH 2 ) y CH 3 , wherein x is an integer from 4 to 19, and y is an integer from 1 to 8, or B is —(CH 2 ) x CH 3 , wherein x is an integer selected from 4, 5, 6, 7, 8, 12, 13, 14, 15, 16, 17, 18, 19, and 20, or B is selected from the group consisting of 2,4-dimethyloctan-2-yl, 2,6-dimethyl-octan-1-yl, and 2,6-dimethyloctan-2-yl.
2 . (canceled)
3 . (canceled)
4 . (canceled)
5 . (canceled)
6 . The compound of claim 1 , wherein A is selected from the group consisting is selected from 2,4-dimethyloctan-2-yl, 2,6-dimethyl-octan-1-yl, 2,6-dimethyloctan-2-yl, 3,7-dimethyloctan-1-yl, and 3,7-dimethyloctan-3-yl.
7 . (canceled)
8 . (canceled)
9 . The compound of claim 1 , wherein B is —(CH 2 ) x CH═CH(CH 2 ) y CH 3 , wherein x is an integer from 4 to 19 (e.g., 3, 4, 5, 8 or 12), and y is an integer from 1 to 8 (e.g., 1, 2, 3, 4, 5, 7, or 8).
10 . The compound of claim 1 , wherein B is —(CH 2 ) x CH 3 , wherein x is an integer selected from 4, 5, 6, 7, 8, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, and 27.
11 . The compound of claim 1 , wherein the compound is selected from the group consisting of:
wherein x is an integer selected from 4, 5, 6, 7, 11, 13, 15 and 17.
12 . (canceled)
13 . The compound of claim 1 , wherein the compound is selected from the group consisting of:
14 . (canceled)
15 . (canceled)
16 . (canceled)
17 . (canceled)
18 . The compound of claim 1 , wherein B is selected from the group consisting of 2,4-dimethyloctan-2-yl, 2,6-dimethyl-octan-1-yl, and 2,6-dimethyloctan-2-yl
19 . The compound of claim 1 , wherein group B is selected from 2,4-dimethyloctan-2-yl, 2,6-dimethyl-octan-1-yl, and 2,6-dimethyloctan-2-yl, and wherein group A is selected from 2,4-dimethyloctan-2-yl, 2,6-dimethyl-octan-1-yl, 2,6-dimethyloctan-2-yl, 3,7-dimethyloctan-1-yl, and 3,7-dimethyloctan-3-yl.
20 . The compound of claim 1 , wherein group A is selected from 2,4-dimethyloctan-2-yl, 2,6-dimethyl-octan-1-yl, 2,6-dimethyloctan-2-yl, 3,7-dimethyloctan-1-yl, and 3,7-dimethyloctan-3-yl, and wherein group B is CH 3 (CH 2 ) 15 —, or cis —CH 3 (CH 2 ) 7 CH═CH(CH 2 ) 8 —.
21 . A method of making the compound of claim 1 , wherein the method comprises the step of reacting a compound of the Formula A, with a compound of Formula B, or an activated halide or sulfonate thereof, in a condensation reaction to form the compound of Formula I:
wherein substituents A and B, are as defined in claim 1 .
22 . A method of making the compound of claim 1 , comprising the step of reacting a compound of the Formula E, with a compound of Formula B in an electrophilic alkene addition reaction to form the compound of Formula I, provided that the compound of Formula E is formable by the dehydration of a compound of Formula A:
wherein substituents A and B, are as defined in claim 1 , and wherein the structure of Formula E is contingent on the structure of Formula A, such that elimination of the OH group and an H atom from adjacent carbon atoms will result in the compound of Formula E.
23 . A composition comprising a compound according to claim 1 , optionally in admixture with one or more pharmaceutically acceptable, cosmetically acceptable, or industrially acceptable excipients or carriers, for example, solvents, oils, surfactants, emollients, diluents, glidants, abrasives, humectants, polymers, plasticizer, catalyst, antioxidant, coloring agent, flavoring agent, fragrance agent, antiperspirant agent, antibacterial agent, antifungal agent, hydrocarbon, stabilizer, or viscosity controlling agent.
24 . A compound according to claim 1 , wherein the compound is:
25 . A compound according to claim 1 , wherein the compound is selected from the group consisting of:
wherein x is an integer selected from 4, 5, 6, 7, 11, 13, 15 and 17.