CANNABIS SPECIES AS INDUSTRIAL CHEMICAL FEEDSTOCKS
The present disclosure is directed to novel derivatives of naturally occurring cannabinoids, methods of making them, compositions comprising them, and methods for using them.
1 . A compound which is a hydrogenated derivative of a cannabinoid.
2 . The compound of claim 1 , wherein the cannabinoid is selected from cannabigerol, cannabichromene, cannabidiol, cannabinol, cannabigerolic acid, cannabichromenic acid, cannabidiolic acid, cannabinolic acid, tetrahydrocannabinol, and tetrahydrocannabinolic acid.
3 . The compound of claim 1 , wherein the cannabinoid is selected from cannabigerol, cannabidiol, cannabinol, cannabigerolic acid, cannabidiolic acid, and tetrahydrocannabinol.
4 . The compound of claim 1 , wherein the compound has a structure selected from the following:
wherein:
each R is independently selected from H, OH, OC 1-21 alkyl, and —OC(O)—C 1-21 alkyl, or any R is absent;
R 1 , R 2 , and R 3 , are each independently selected from H, C 1-21 alkyl, —C(O)—C 1-21 alkyl, C 2-21 alkenyl, —C(O)—C 2-21 alkenyl, C 3-7 cycloalkyl, —C(O)—C 3-7 cycloalkyl, C 1-6 haloalkyl, —C(O)—C 1-6 haloalkyl, (CH 2 CH 2 O)nCH 2 CH 2 OH, (CH 2 CH(CH 3 )O)nCH 2 CH(CH 3 )OH, C 1-21 alkyl-OH, C 1-21 alkyl-C(O)—OC 1-6 alkyl, C(O)—C 1-21 alkyl-C(O)—OC 1-6 alkyl, C 1-21 alkyl-COOH, —C(O)—C 1-21 alkyl-COOH, —P(O)(OC 1-21 alkyl)(OC 1-21 alkyl), —SO 2 OC 1-21 alkyl, —SO 2 C 1-21 alkyl, C 1-21 alkyl-P(O)(OC 1-6 alkyl)(OC 1-6 alkyl), —C(O)—C 1-21 alkyl-P(O)(OC 1-6 alkyl)(OC 1-6 alkyl), C 1-21 alkyl-P(O)(OH)(OC 1-6 alkyl), —C(O)—C 1-21 alkyl-P(O)(OH)(OC 1-6 alkyl), C 1-21 alkyl-P(O)(OH) 2 , —C(O)—C 1-21 alkyl-P(O)(OH) 2 , C 1-21 alkyl-SO 2 OC 1-6 alkyl), —C(O)—C 1-21 alkyl-SO 2 OC 1-6 alkyl, C 1-21 alkyl-SO 3 H, and —C(O)—C 1-21 alkyl-SO 3 H; or any of R 1 , R 2 , or R 3 , is absent; and wherein each n is independently an integer selected from 0 to 20;
R 4 is independently selected from H, OH, C 1-21 alkyl, OC 1-21 alkyl, C 2-21 alkenyl, —OC 2-21 alkenyl, C 3-7 cycloalkyl, OC 3-7 cycloalkyl, C 1-6 haloalkyl, OC 1-6 haloalkyl, O(CH 2 CH 2 O)nCH 2 CH 2 OH, O(CH 2 CH(CH 3 )O)nCH 2 CH(CH 3 )OH, C 1-21 alkyl-OH, —C(O)—C 1-21 alkyl-OH, C 1-21 alkyl-C(O)—OC 1-6 alkyl, OC 1-21 alkyl-C(O)—OC 1-6 alkyl, C 1-21 alkyl-COOH, OC 1-21 alkyl-COOH, —C 1-21 alkyl-P(O)(OC 1-6 alkyl)(OC 1-6 alkyl), —OC 1-21 alkyl-P(O)(OC 1-6 alkyl)(OC 1-6 alkyl), C 1-21 alkyl-P(O)(OH)(OC 1-6 alkyl), —OC 1-21 alkyl-P(O)(OH)(OC 1-6 alkyl), C 1-21 alkyl-P(O)(OH) 2 , —OC 1-21 alkyl-P(O)(OH) 2 , C 1-21 alkyl-SO 2 OC 1-6 alkyl), —OC 1-21 alkyl-SO 2 OC 1-6 alkyl, C 1-21 alkyl-SO 3 H, and —OC 1-21 alkyl-SO 3 H; or R 4 is absent; and wherein each n is independently an integer selected from 0 to 20;
wherein each “ ” is either a single bond or a double bond, and wherein each “ ” is either a single bond or is absent;
provided that the bonds “ ” and “ ” are selected such that all carbon atoms and oxygen atoms to which these bonds are attached have a total of four attached bonds inclusive of single and double bonds (e.g., if R 1 , R 2 , or R 3 is absent, then the bond attached to the respective oxygen atom is a double bond).
5 . The compound of claim 4 , wherein the compound has a structure selected from:
wherein each R is independently H or OH, and R 1 , R 2 , R 3 and R 4 are each as defined in claim 4 .
6 . The compound of claim 4 , wherein the compound has a structure selected from:
wherein R 1 , R 2 , R 3 and R 4 are each as defined in claim 4 .
7 . The compound of claim 4 , wherein the compound has a structure selected from:
wherein R 1 , R 2 , R 3 and R 4 are each as defined in claim 4 .
8 . The compound of claim 4 , wherein the compound has a structure selected from:
wherein R 1 , R 2 , R 3 and R 4 are each as defined in claim 4 .
9 . The compound of claim 4 , wherein the compound has a structure selected from:
wherein R 3 and R 4 are each as defined in claim 4 .
10 . The compound of claim 4 , wherein the compound has a structure selected from:
wherein R 3 and R 4 are each as defined in claim 4 .
11 . The compound according to claim 4 ,
wherein each group R is H; and wherein:
(a) R 1 , R 2 , and R 4 are each H and R 3 is absent, or
(b) R 1 and R 2 are each H, and R 4 is OH, and R 3 is absent, or
(c) R 1 , R 2 , R 3 and R 4 are each H.
12 . The compound according to claim 4 , wherein the group:
is selected from one of the following:
13 . The compound of claim 4 , wherein the compound has a structure selected from:
14 . The compound of claim 4 , wherein the compound has a structure selected from:
15 . The compound of claim 4 , wherein the compound has a structure selected from:
16 . The compound of claim 4 , wherein the compound has a structure selected from:
17 . The compound of claim 4 , wherein the compound has a structure selected from:
18 . A method of making a compound according to claim 1 , comprising the step of reducing a cannabinoid (e.g., by catalytic hydrogenation) to provide a hydrogenated (e.g., partially or fully hydrogenated) cannabinoid, and optionally further derivatizing the initial hydrogenation product to form additional compounds, e.g., esters, ethers, acids, alcohols, aldehydes, ketones, and other derivatives.
19 . An emollient, solubilizer, anti-frizz agent, lubricant, carrier, conditioner, surfactant, adjuvant, dispersant, emulsifier, fuel, paraffin, candle, or precursor of a polymer, film-former, resin, or composite, comprising or consisting of a compound according to claim 1 .
20 . 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.