Methods for converting thc-rich cannabinoid mixtures into cbn-rich cannabinoid mixtures
AssigneeCanopy Growth Corporation
InventorsChristopher ADAIR, Mahmood AZIZPOOR FARD, Ben GEILING, Mohammadmehdi HAGHDOOST MANJILI
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Abstract
Disclosed herein is a method of converting a THC-rich cannabinoid mixture that comprises at least about 20% THC into a CBN-rich cannabinoid mixture that comprises at least about 2.0% CBN. The method comprises contacting the cannabinoid mixture with a benzoquinone reagent under reaction conditions comprising: (i) a reaction temperature that is within a target reaction-temperature range; and (ii) a reaction time that is within a target reaction-time range, such that at least a portion of the of the THC in the THC-rich cannabinoid mixture is converted into CBN.
Claims26
A method of converting a tetrahydrocannabinol (THC)-rich cannabinoid mixture that comprises at least about 20 wt. % THC into a cannabinol (CBN)-rich cannabinoid mixture that comprises at least about 2.0 wt. % CBN, the method comprising contacting the cannabinoid mixture with a benzoquinone reagent.
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A method of converting tetrahydrocannabinol (THC) into cannabinol (CBN), the method comprising:
- contacting the THC with a benzoquinone reagent that is a compound as defined in formula (I):
- where X1, X2, X3 and X4 are as defined as in any one of 1 to 133:
- X1
- X2
- X3
- X4
- 1
- H
- H
- H
- H
- 2
- C6H5
- H
- H
- H
- 3
- CH3
- H
- H
- H
- 4
- C(CH3)3
- H
- H
- H
- 5
- OCH3
- H
- H
- H
- 6
- N(CH3)2
- H
- H
- H
- 7
- NH2
- H
- H
- H
- 8
- CH2CH3
- H
- H
- H
- 9
- OH
- H
- H
- H
- 10
- OCH2CH3
- H
- H
- H
- 11
- F
- H
- H
- H
- 12
- CI
- H
- H
- H
- 13
- Br
- H
- H
- H
- 14
- SH
- H
- H
- H
- 15
- SiH3
- H
- H
- H
- 16
- CHO
- H
- H
- H
- 17
- COOCH3
- H
- H
- H
- 18
- CF3
- H
- H
- H
- 19
- CN
- H
- H
- H
- 20
- COOH
- H
- H
- H
- 21
- SO3
- H
- H
- H
- 22
- NO2
- H
- H
- H
- 23
- COCH3
- H
- H
- H
- 24
- C6H5
- C6H5
- H
- H
- 25
- CH3
- CH3
- H
- H
- 26
- C(CH3)3
- C(CH3)3
- H
- H
- 27
- OCH3
- OCH3
- H
- H
- 28
- N(CH3)2
- N(CH3)2
- H
- H
- 29
- NH2
- NH2
- H
- H
- 30
- CH2CH3
- CH2CH3
- H
- H
- 31
- OH
- OH
- H
- H
- 32
- OCH2CH3
- OCH2CH3
- H
- H
- 33
- F
- F
- H
- H
- 34
- CI
- CI
- H
- H
- 35
- Br
- Br
- H
- H
- 36
- SH
- SH
- H
- H
- 37
- SiH3
- SiH3
- H
- H
- 38
- CHO
- CHO
- H
- H
- 39
- COOCH3
- COOCH3
- H
- H
- 40
- CF3
- CF3
- H
- H
- 41
- CN
- CN
- H
- H
- 42
- COOH
- COOH
- H
- H
- 43
- SO3
- SO3
- H
- H
- 44
- NO2
- NO2
- H
- H
- 45
- COCH3
- COCH3
- H
- H
- 46
- C6H5
- H
- C6H5
- H
- 47
- CH3
- H
- CH3
- H
- 48
- C(CH3)3
- H
- C(CH3)3
- H
- 49
- OCH3
- H
- OCH3
- H
- 50
- N(CH3)2
- H
- N(CH3)2
- H
- 51
- NH2
- H
- NH2
- H
- 52
- CH2CH3
- H
- CH2CH3
- H
- 53
- OH
- H
- OH
- H
- 54
- OCH2CH3
- H
- OCH2CH3
- H
- 55
- F
- H
- F
- H
- 56
- CI
- H
- CI
- H
- 57
- Br
- H
- Br
- H
- 58
- SH
- H
- SH
- H
- 59
- SiH3
- H
- SiH3
- H
- 60
- CHO
- H
- CHO
- H
- 61
- COOCH3
- H
- COOCH3
- H
- 62
- CF3
- H
- CF3
- H
- 63
- CN
- H
- CN
- H
- 64
- COOH
- H
- COOH
- H
- 65
- SO3
- H
- SO3
- H
- 66
- NO2
- H
- NO2
- H
- 67
- COCH3
- H
- COCH3
- H
- 68
- C6H5
- H
- H
- C6H5
- 69
- CH3
- H
- H
- CH3
- 70
- C(CH3)3
- H
- H
- C(CH3)3
- 71
- OCH3
- H
- H
- OCH3
- 72
- N(CH3)2
- H
- H
- N(CH3)2
- 73
- NH2
- H
- H
- NH2
- 74
- CH2CH3
- H
- H
- CH2CH3
- 75
- OH
- H
- H
- OH
- 76
- OCH2CH3
- H
- H
- OCH2CH3
- 77
- F
- H
- H
- F
- 78
- CI
- H
- H
- CI
- 79
- Br
- H
- H
- Br
- 80
- SH
- H
- H
- SH
- 81
- SiH3
- H
- H
- SiH3
- 82
- CHO
- H
- H
- CHO
- 83
- COOCH3
- H
- H
- COOCH3
- 84
- CF3
- H
- H
- CF3
- 85
- CN
- H
- H
- CN
- 86
- COOH
- H
- H
- COOH
- 87
- SO3
- H
- H
- SO3
- 88
- NO2
- H
- H
- NO2
- 89
- COCH3
- H
- H
- COCH3
- 90
- C6H5
- C6H5
- C6H5
- H
- 91
- CH3
- CH3
- CH3
- H
- 92
- C(CH3)3
- C(CH3)3
- C(CH3)3
- H
- 93
- OCH3
- OCH3
- OCH3
- H
- 94
- N(CH3)2
- N(CH3)2
- N(CH3)2
- H
- 95
- NH2
- NH2
- NH2
- H
- 96
- CH2CH3
- CH2CH3
- CH2CH3
- H
- 97
- OH
- OH
- OH
- H
- 98
- OCH2CH3
- OCH2CH3
- OCH2CH3
- H
- 99
- F
- F
- F
- H
- 100
- CI
- CI
- CI
- H
- 101
- Br
- Br
- Br
- H
- 102
- SH
- SH
- SH
- H
- 103
- SiH3
- SiH3
- SiH3
- H
- 104
- CHO
- CHO
- CHO
- H
- 105
- COOCH3
- COOCH3
- COOCH3
- H
- 106
- CF3
- CF3
- CF3
- H
- 107
- CN
- CN
- CN
- H
- 108
- COOH
- COOH
- COOH
- H
- 109
- SO3
- SO3
- SO3
- H
- 110
- NO2
- NO2
- NO2
- H
- 111
- COCH3
- COCH3
- COCH3
- H
- 112
- C6H3
- C6H3
- C6H3
- C6H3
- 113
- CH3
- CH3
- CH3
- CH3
- 114
- C(CH3)3
- C(CH3)3
- C(CH3)3
- C(CH3)3
- 115
- OCH3
- OCH3
- OCH3
- OCH3
- 116
- N(CH3)2
- N(CH3)2
- N(CH3)2
- N(CH3)2
- 117
- NH2
- NH2
- NH2
- NH2
- 118
- CH2CH3
- CH2CH3
- CH2CH3
- CH2CH3
- 119
- OH
- OH
- OH
- OH
- 120
- OCH2CH3
- OCH2CH3
- OCH2CH3
- OCH2CH3
- 121
- F
- F
- F
- F
- 122
- Br
- Br
- Br
- Br
- 123
- SH
- SH
- SH
- SH
- 124
- SiH3
- SiH3
- SiH3
- SiH3
- 125
- CHO
- CHO
- CHO
- CHO
- 126
- COOCH3
- COOCH3
- COOCH3
- COOCH3
- 127
- CF3
- CF3
- CF3
- CF3
- 128
- CN
- CN
- CN
- CN
- 129
- COOH
- COOH
- COOH
- COOH
- 130
- SO3
- SO3
- SO3
- SO3
- 131
- NO2
- NO2
- NO2
- NO2
- 132
- COCH3
- COCH3
- COCH3
- COCH3
- 133
- CN
- CN
- CI
- CI
A method of converting tetrahydrocannabinol (THC) into cannabinol (CBN), the method comprising:
- contacting the THC with a benzoquinone reagent that is a compound as defined in formula (II):
- wherein X1, X2, X3, and X4 are each independently:
- H;
- a halide;
- a C<12-hydrocarbyl;
- a C<12-heteroaryl;
- a C<12-heteroaralkyl;
- a C<12-heteroaralkenyl;
- hydroxyl;
- a C<12-alkoxy;
- a C<12-amino;
- a C<12-acyl;
- a C<12-amide;
- a C<12-ester;
- a C<12-ketone;
- or a substituted analog thereof.
Dependencies are inferred from the claim text.