Dimethylformamide → 3Alpha,7Alpha,12Alpha-trihydroxy-5Beta-cholestan-26-oic acid

HRID 1055491Notes

Reaction equation

HRID 1055491 reaction equation
CN(C=O)C.[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[C:16]([C:17]([OH:19])=[O:18])=[C:15]([OH:20])[C:14]([CH2:21]/[CH:22]=[C:23](/[CH2:25][CH2:26][CH:27]=[C:28]([CH3:30])[CH3:29])\[CH3:24])=[C:13]([OH:31])[CH:12]=1.[CH3:32][C@@H:33]([C@@H:42]1[C@@:46]2([CH3:63])[C@@H:47]([OH:62])[CH2:48][C@@H:49]3[C@@:54]4([CH3:60])[CH2:55][CH2:56][C@@H:57]([OH:59])[CH2:58][C@H:53]4[CH2:52][C@@H:51]([OH:61])[C@H:50]3[C@@H:45]2[CH2:44][CH2:43]1)[CH2:34][CH2:35][CH2:36][CH:37]([C:39]([OH:41])=[O:40])[CH3:38]>CS(C)=O.CC(O)C>[CH3:32][C@@H:33]([C@@H:42]1[C@@:46]2([CH3:63])[C@@H:47]([OH:62])[CH2:48][C@@H:49]3[C@@:54]4([CH3:60])[CH2:55][CH2:56][C@@H:57]([OH:59])[CH2:58][C@H:53]4[CH2:52][C@@H:51]([OH:61])[C@H:50]3[C@@H:45]2[CH2:44][CH2:43]1)[CH2:34][CH2:35][CH2:36][CH:37]([C:39]([OH:41])=[O:40])[CH3:38].[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[C:16]([C:17]([OH:19])=[O:18])=[C:15]([O-:20])[C:14]2[CH:21]=[CH:22][C:23]([CH2:25][CH2:26][CH:27]=[C:28]([CH3:30])[CH3:29])([CH3:24])[O:31][C:13]=2[CH:12]=1

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 1223123Alpha,7Alpha,12Alpha-trihydroxy-5Beta-cholestan-26-oic acidHCID 6449999Cannabigerolic Acid

Product 2

HCID 1223123Alpha,7Alpha,12Alpha-trihydroxy-5Beta-cholestan-26-oic acidHCID 54740355Cannabichromenate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 3776IsopropanolSolvent

Procedure

Table 6 below shows that DMSO, DMF, IPA and cyclodextrin facilitated solubilization of cannabinoids. Cyclodextrin solubilized up to 20-25 g/L of CBGA for conversion. Enzymatic rate was enhanced when 20% DMSO (v/v) was added to the reaction mixture and THCA synthase produced both THCA and CBCA in the reaction (Table 7).

Sources & evidence

ORD record
ord-acf522adba094ecc8137c9cf4756d3d2
Source dataset
uspto-grants-2016_07
Patent number
US09394510B2

Reaction notes

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