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 terpene alcohol ether compound of the general formula (I):
in free or salt form, wherein A is the core of a terpene alcohol or derivative thereof, and wherein B is either:
(i) the saturated or unsaturated hydrocarbon chain, or derivative thereof, of a natural or unnatural fatty alcohol; or
(ii) the core of a terpene alcohol or derivative thereof, either the same or different than substituent A.
2 . The compound of claim 1 , wherein A is the core of a terpene alcohol, or derivative thereof, wherein said terpene is a monoterpene, sesquiterpene, diterpene, sesterterpene, or triterpene.
3 . The compound of claim 1 , wherein A is the core of a terpene alcohol, or derivative thereof, wherein said terpene alcohol is selected from citronellol, isocitronellol, geraniol, nerol, menthol, myrcenol, linalool, thymol, a-terpineol, b-terpineol, g-terpineol, borneol, farnesol, nerolidol, and carotol.
4 . The compound of claim 3 , wherein said terpene alcohol is selected from citronellol, myrcenol, linalool, and farnesol.
5 . The compound of claim 1 , wherein said terpene alcohol, or derivative thereof, is fully saturated (e.g., said terpene alcohol is a fully saturated monoterpene derivative, e.g., an isodecyl moiety).
6 . The compound of claim 1 , wherein A is selected from the group consisting of:
7 . The compound of claim 1 , wherein B is the saturated or unsaturated hydrocarbon chain, or derivative thereof, of a C4 to C28 fatty alcohol (i.e., group B has a C4 to C28 hydrocarbon chain).
8 . The compound of claim 1 , wherein B is an unsaturated hydrocarbon chain, e.g., monounsaturated, diunsaturated or triunsaturated.
9 . The compound of claim 8 , 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 a saturated hydrocarbon chain, e.g., B is —(CH 2 ) x CH 3 , wherein x is an integer from 4 to 27 (e.g., 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, or 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, 8, 9, 11, 13, 15 and 17.
12 . The compound of claim 1 , wherein group A is an isodecyl group, e.g., 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 optionally wherein group B is CH 3 (CH 2 ) 15 —, CH 3 (CH 2 ) 11 —, or cis- CH 3 (CH 2 ) 7 CH═CH(CH 2 ) 8 —.
13 . The compound of claim 1 , wherein the compound is selected from the group consisting of:
14 . The compound of claim 1 , wherein B is the core of a terpene alcohol, or derivative thereof, wherein said terpene is a monoterpene, sesquiterpene, diterpene, sesterterpene, or triterpene.
15 . The compound of claim 1 , wherein B is the core of a terpene alcohol, or derivative thereof, wherein said terpene alcohol is selected from citronellol, isocitronellol, geraniol, nerol, menthol, myrcenol, linalool, thymol, a-terpineol, b-terpineol, g-terpineol, borneol, farnesol, nerolidol, and carotol.
16 . The compound of claim 15 , wherein said terpene alcohol is selected from citronellol, myrcenol, linalool, and farnesol.
17 . The compound of claim 14 , wherein said terpene alcohol, or derivative thereof, is fully saturated (e.g., said terpene alcohol is a fully saturated monoterpene derivative, e.g., an isodecyl moiety).
18 . The compound of claim 1 , wherein B is selected from the group consisting of:
19 . The compound of claim 1 , wherein group B is an isodecyl group, e.g., selected from 2,4-dimethyloctan-2-yl, 2,6-dimethyl-octan-1-yl, 2,6-dimethyloctan-2-yl, 3,7-dimethyloctan-l-yl, and 3,7-dimethyloctan-3-yl, optionally wherein group A and group B are each independently an isodecyl group, e.g., A and B are each independently 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 the compound is selected from the group consisting of:
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.