Silicon-based cannabidiol derivatives and compositions thereof
Silicon-based cannabidiol derivatives and methods for their synthesis are provided, in which the derivatives contain a cannabidiol molecule and at least one silicon-based group containing Si—O—Si bonds. The derivatives are useful in cosmetic and topical compositions, have potential beneficial topical properties, and enhance solubility and compatibility in cosmetic formulations containing the silicon-based materials. Silicone elastomers infused with compositions containing the silicon-based cannabidiol derivatives and trisiloxanes are also provided.
1. A silicon-based cannabidiol derivative comprising at least one silicon-based functional group containing Si—O—Si bonds which is bound to a cannabidiol molecule having formula (I):
2. The silicon-based cannabidiol derivative according to claim 1 , wherein the at least one silicon-based functional group is bound to the cannabidiol molecule by a phenolic oxygen atom in the benzenediol ring.
3. The silicon-based cannabidiol derivative according to claim 1 , wherein the derivative comprises one silicon-based functional group bound to the cannabidiol molecule by the isopropenyl group.
4. The silicon-based cannabidiol derivative according to claim 1 , wherein the derivative comprises one silicon-based functional group bound to the cannabidiol molecule by the isopropenyl group and at least one silicon-based functional group bound to the cannabidiol molecule by a phenolic oxygen atom in the benzenediol ring.
5. The silicon-based cannabidiol derivative according to claim 1 , wherein the at least one silicon-based functional group is a siloxanyl group or trialkoxysilane-containing group.
6. The silicon-based cannabidiol derivative according to claim 1 , wherein the at least one silicon-based functional group contains at least two silicon atoms.
7. The silicon-based cannabidiol derivative according to claim 1 , having formula (A), (B), (C), (D), (E), or (F), wherein R 1 , R 2 , and R 3 are independently SiMe(OSiMe 3 ) 2 or SiMe 2 (OSiMe 2 ) 4 CH 2 CH 2 CH 2 CH 3
8. The silicon-based cannabidiol derivative according to claim 1 , having formula (II):
9. The silicon-based cannabidiol derivative according to claim 1 , having formula (III):
10. The silicon-based cannabidiol derivative according to claim 1 , having formula (IV):
11. The silicon-based cannabidiol derivative according to claim 1 , having formula (V):
12. A cosmetic or topical composition comprising a base formulation and at least one silicon-based cannabidiol derivative, wherein the at least one silicon-based cannabidiol derivative comprises at least one silicon-based functional group containing Si—O—Si bonds which is bound to a cannabidiol molecule having formula (I):
13. The cosmetic or topical composition according to claim 12 , wherein the at least one silicon-based functional group is bound to the cannabidiol molecule by a phenolic oxygen atom in the benzenediol ring.
14. The cosmetic or topical composition according to claim 12 , wherein the derivative comprises one silicon-based functional group bound to the cannabidiol molecule by the isopropenyl group.
15. The cosmetic or topical composition according to claim 12 , wherein the derivative comprises one silicon-based functional group bound to the cannabidiol molecule by the isopropenyl group and at least one silicon-based functional group bound to the cannabidiol molecule by a phenolic oxygen atom in the benzenediol ring.
16. The cosmetic or topical composition according to claim 12 , wherein the at least one silicon-based functional group is a siloxanyl group or trialkoxysilane-containing group.
17. The cosmetic or topical composition according to claim 12 , wherein the at least one silicon-based functional group contains at least two silicon atoms.
18. A method for making the silicon-based cannabidiol derivative according to claim 1 , comprising hydrosilylating the isopropenyl group of cannabidiol to form the silicon-based cannabidiol derivative.
19. A method for making the silicon-based cannabidiol derivative according to claim 1 , comprising reacting cannabidiol with an allylic halide in a solvent to form an allyloxycannabidiol intermediate, and reacting the allyloxycannabidiol intermediate with a silane compound and a catalyst to form the silicon-based cannabidiol derivative.
20. A method for making the silicon-based cannabidiol derivative according to claim 1 , comprising forming a silylated alkyl ether on a cannabidiol molecule by reacting a chlorine-containing siloxane compound with a hydroxyl group in the presence of a base acceptor.
21. A method for making the silicon-based cannabidiol derivative according to claim 1 , comprising forming a silylated alkyl ether on a cannabidiol molecule by dehydrogenative coupling of a hydride-containing siloxane.
22. A method for making the silicon-based cannabidiol derivative according to claim 1 , comprising forming a silylated alkyl ether on a cannabidiol molecule by forming an intermediate alkali metal alkoxide followed by reaction with a silicon-hydride or silicon-chlorine containing compound.
23. A composition comprising the silicon-based cannabidiol derivative according to claim 1 and at least one phytochemical extracted from hemp oil.
24. A composition comprising the silicon-based cannabidiol derivative according to claim 1 and a siloxane, wherein the composition spreads to a thin film which forms cannabidiol upon reaction with moisture.
25. A silicone elastomer or fluid infused with the composition according to claim 24 .